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EP1709039A1 - Complexes metalliques utilises comme composes absorbant la lumiere dans la couche d'informations de supports de donnees optiques - Google Patents

Complexes metalliques utilises comme composes absorbant la lumiere dans la couche d'informations de supports de donnees optiques

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Publication number
EP1709039A1
EP1709039A1 EP05700952A EP05700952A EP1709039A1 EP 1709039 A1 EP1709039 A1 EP 1709039A1 EP 05700952 A EP05700952 A EP 05700952A EP 05700952 A EP05700952 A EP 05700952A EP 1709039 A1 EP1709039 A1 EP 1709039A1
Authority
EP
European Patent Office
Prior art keywords
methyl
substituted
cyano
methoxy
ylidene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05700952A
Other languages
German (de)
English (en)
Inventor
Horst Berneth
Karin HASSENRÜCK
Christa-Maria KRÜGER
Josef-Walter Stawitz
Timo Meyer-Friedrichsen
Friedrich-Karl Bruder
Rafael Oser
Serguei Kostromine
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanxess Deutschland GmbH
Original Assignee
Lanxess Deutschland GmbH
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Filing date
Publication date
Application filed by Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Publication of EP1709039A1 publication Critical patent/EP1709039A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • G11B7/242—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
    • 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
    • G11B7/2498—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 as cations
    • 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
    • G11B7/253—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
    • G11B7/2534—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 polycarbonates [PC]

Definitions

  • Metal complexes as light-absorbing compounds in the information layer of optical data carriers are Metal complexes as light-absorbing compounds in the information layer of optical data carriers
  • the invention relates to optical data storage devices containing metal complexes in their information layer, a process for their production, the metal complexes contained, their production and the ligands on which the metal complexes are based and processes for their production.
  • the write-once optical data carriers using special light-absorbing substances or mixtures thereof are particularly suitable for use in high-density writable optical data memories that work with blue laser diodes, in particular GaN or SHG laser diodes (360 - 460 nm).
  • the next generation of optical data storage media - the DVD - is currently being launched on the market.
  • the storage density can be increased by using shorter-wave laser radiation (635 to 660 nm) and a higher numerical aperture NA.
  • the recordable format in this case is DVD-R (DVD-R, DVD + R).
  • the patent literature describes dye-based writable optical data memories which are equally suitable for CD-R and DVD-R systems (JP-A 11 043 481 and JP-A 10 181 206).
  • JP-A 11 043 481 and JP-A 10 181 206 For a high reflectivity and a high modulation level of the readout signal, as well as for a sufficient sensitivity when writing, use is made of the fact that the IR wavelength 780 nm of the CD-R lies at the foot of the long-wave flank of the absorption peak of the dye, the red one Wavelength 635 nm or 650 nm of the DVD-R lies at the foot of the short-wave flank of the absorption peak of the dye.
  • Dyes for the blue laser are also known from WO-A 03/063151.
  • 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 a 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 insufficient heat resistance at the interface to a polymer carrier can diffuse into the latter and in turn adversely affect the reflectivity.
  • An excessively high vapor pressure of a light-absorbing substance can sublimate the above-mentioned sputtering or vapor deposition of further layers in a high vacuum and thus reduce the desired layer thickness. This in turn leads to a negative influence on the reflectivity.
  • the object of the invention is therefore to provide data carriers equipped with suitable connections which meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the formation layer in a write-once optical data carrier for fulfill high-density writable optical data storage formats in a laser wavelength range from 360 to 460 nm.
  • the numerical aperture NA of the objective lens is preferably greater than or equal to 0.60, particularly preferably greater than or equal to 0.70, very particularly preferably greater than or equal to 0.80.
  • optical data carriers with light-absorbing compounds from the group of special metal complexes can meet the above-mentioned requirement profile particularly well.
  • the invention therefore relates to optical data carriers containing a preferably transparent substrate, optionally already coated with one or more reflection layers and / or protective layers, on the surface of which an information layer which can be written on by light - optionally one or more reflection layers and optionally a protective layer or another substrate or one Cover layer are applied, which can be written and read with blue light, preferably with a wavelength in the range of 360-460 nm, in particular 390 to 420 nm, very particularly preferably from 400 to 410 nm, preferably laser light, the information layer being a contains light-absorbing compound and optionally a binder, characterized in that at least one metal complex is used as the light-absorbing compound, which has at least one ligand of formula (I)
  • A represents an optionally substituted and / or benzyl- or naphthane-fused five- or six-membered aromatic or quasi-aromatic or partially hydrogenated heterocyclic radical
  • n 0 or 1
  • Y 1 represents N or CR 1 ,
  • Y 2 stands for N or CR ", stands for N or CR 3 ,
  • X represents O, S or NR 5 ,
  • R 5 is hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl, acyl, aryl or a hetero ⁇ cychschen residue provides, R ⁇ is R independently of one another are hydrogen, halogen, alkyl, alkoxy, mono- or dialkylamino, aralkyl, aryl, hetaryl, arylazo, hetarylazo, cyano or alkoxycarbonyl,
  • R 2 ; R 3 and R; R 5 can each independently form an optionally substituted bridge and
  • R 2 ; R 5 can form an optionally substituted bridge if n is 0.
  • N is preferably 0. Likewise, n is preferably 1.
  • R 1 to R 4 have the meaning given above.
  • X is preferably NR 5 , where R 5 has the meaning given above.
  • -CR 2 -N ⁇ -R 5 or -CR 4 -N ° -R 5 stands for a ring of the formula (X)
  • B represents an optionally substituted and / or benzyl or naphthane-fused five- or six-membered aromatic or quasi-aromatic or partially hydrogenated heterocyclic radical.
  • the metal complexes are in the form of 1: 1, 1: 2 or 1 ⁇ metal complexes.
  • Preferred metal complexes are those which are characterized in that they have the formula (Ia)
  • M stands for a metal
  • Preferred metal complexes are those which are characterized in that they have the formula (Ib)
  • M stands for a metal
  • Preferred metals of the metal complexes used according to the invention are:
  • Preferred metals in formulas (la) and (Ib) are divalent metals, transition metals or rare earths, in particular Mg, Ca, Sr, Ba, Cu, Ni, Co, Fe, Zn, Pd, Pt, Ru, Th, Os or sm in question.
  • the metals Pd, Fe, Zn, Cu, Ni and Co. are preferred.
  • Ni is particularly preferred.
  • M stands for a metal
  • Preferred metals in the formula (Ic) are trivalent metals, transition metals or rare earths, in particular B, Al, Ga, In, V, Co, Cr, Fe, Y, La, Ce, Pr, Nd, Sm, Eu, Gd or Tb in question.
  • B, Al and Co. are preferred.
  • Co. is particularly preferred.
  • A is preferably 2-pyridyl, 2-quinolyl, 2-pyrimidyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,3-thiazol-2-yl, 1,3-thiazolin 2-yl, l, 3-thiazol-4-yl, benzothiazol-2-yl, l, 2-thiazol-3-yl, benzoisothiazol-3-yl, l, 3-oxazol-2-yl, l, 3-oxazolin-2-yl, benzoxazol-2-yl, 1,2-oxazol-3-yl, imidazol-2-yl,
  • Imidazolin-2-yl benzimidazol-2-yl, imidazol-4-yl, pyrazol-5-yl, pyrrolin-2-yl, pyrrol-2-yl, 1,3,4- Triazol-2-yl, 3H-indolin-2-yl, tetrahydroisoindol-l-yl, isoindol-l-yl, benz (cd) indol-2-yl, 1,3,4-thiadiazol-2-yl, l, 2,4-thiadiazol-5-yl, l, 2,4-thiadiazol-3-yl or l, 3,4-oxadiazol-2-yl, which may optionally be substituted.
  • A is particularly preferably 2-pyridyl, 2-quinolyl, 1,3-thiazol-2-yl, 1,3-thiazolin-2-yl, benzothiazol-2-yl, 1,3-oxazol-2-yl, benzoxazole -2-yl, imidazol-2-yl, benzimidazol-2-yl, pyrazol-5-yl, pyrrolin-2-yl, pyrrol-2-yl, l, 3,4-triazol-2-yl, 3H-indoline -2-yl, tetrahydroisoindol-l-yl, isoindol-l-yl, benz (cd) indol-2-yl, l, 3,4-thiadiazol-2-yl, l, 2,4-thiadiazol-5-yl or 1,3,4-oxadiazol-2-yl, which may optionally be substituted.
  • Substituents from the series of the branched C 3 -C 8 alkoxy radicals are particularly preferred, for example -O-CH 2 -CH (CH 3 ) 2 , -O-CH [CH (CH 3 ) 2 ] 2 , -OC (CH 3 ) 3 , -O-CH 2 -CH (C 2 H 5 ) (C 4 H 9 ), -O-CH 2 -C (CH 3 ) 2 -C 2 H 5 , the branched or ring-closed C2-C 3 - Alkylaminomethyl radicals, for example -CH 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -CH 2 NH-CH 2 -CH (C 2 H 5 ) (C 4 H 9 ), -CH 2 NH-CH [CH ( CH 3 ) 2 ] 2 , a radical of the formula
  • the optionally branched C 2 -C 5 alkoxycarbonyl radicals for example -COOCHjCTL j , -COO-CH (CH 3 ) 2 , -COO-CH [CH (CH 3 ) 2 ] 2
  • the optionally branched or ring-closed C2-Cg-alkylaminosulfonyl radicals for example -SO 2 N (CH 2 CH (CH3)) 2 , -S0 2 NHCH 2 CH (CH 3 ) 2 , -SO 2 NHC (CH 3 ) 2 CH 2 CH 3 , -SO 2 NHC (CH 3 ) 3 ,
  • R 6 represents hydrogen, Cx-C ⁇ alkyl or C 6 -C ⁇ 0 aryl and
  • R 7 represents hydrogen, Ci-C ⁇ -alkyl, C 6 -C 10 aryl or a heterocyclic radical.
  • the radical X preferably represents NR 5 , where R 5 has the meaning given above.
  • 2-pyridyl which contains up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, tert-butoxy, 2,4-dimethyl-3-pentoxy, di-isobutylaminosulfonyl, tert pentylaminosulfonyl, bis (hydroxyethyl) aminosulfonyl, morpholinosulfonyl, methoxyethoxypropylaminosulfonyl, nitro or cyano may be substituted, 2-Quinolyl, which consists of up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, tert-butoxy, 2,4-dimethyl-3-pentoxy, di-isobutylaminosulfonyl, tert.
  • pentylaminosulfonyl bis (hydroxyethyl) aminosulfonyl, morpholinosulfonyl, methoxyethoxypropylaminosulfonyl, nitro or cyano may be substituted,
  • Benzthiazol-2-yl which consists of up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, tert-butoxy, 2,4-dimethyl-3-pentoxy, methoxycarbonyl, di-isobutylamino -sulfonyl, tert-pentylaminosulfonyl, bis- (hydroxyethyl) aminosulfonyl, morpholinosulfonyl, methoxyethoxypropylaminosulfonyl, nitro or cyano may be substituted,
  • Benzoxazol-2-yl which consists of up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, tert-butoxy, 2,4-dimethyl-3-pentoxy, methoxycarbonyl, di-isobutylamino sulfonyl, tert-pentylaminosulfonyl, bis- (hydroxyethyl) aminosulfonyl, morpholinosulfonyl, methoxyethoxypropylaminosulfonyl, nitro or cyano may be substituted,
  • Benzimidazol-2-yl which consists of up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, tert-butoxy, 2,4-dimethyl-3-pentoxy, methoxycarbonyl, di-isobutylamino -sulfonyl, tert-pentylaminosulfonyl, bis- (hydroxyethyl) aminosulfonyl, Mo holinosulfonyl, methoxyethoxypropylaminosulfonyl, nitro or cyano may be substituted,
  • Pyrrol-2-yl which can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, methoxycarbonyl, nitro or cyano and / or the in
  • Position 34 carries a - ⁇ CTLJr or - (CH 2 ) bridge and / or that in position 5 by hnino, Dicyanomethylene, methoxycarbonyl-cyano-methylene, ethoxycarbonyl-cyano-methylene or a radical of the formula (XU)
  • X is NR 5 and Y 1 to Y 3 , R 4 , n and R 5 have the meaning given above, but are independent thereof, and can be substituted,
  • 3-HTndolin-2-yl which bears two methyl groups or an oxo group in position 3 and can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, methoxycarbonyl, nitro or cyano,
  • Isoindol-1-yl which can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, methoxycarbonyl, nitro or cyano and / or which is in position 3 by imino, dicyanomethylene, methoxycarbonyl-cyano- methylene, ethoxycarbonyl-cyano-methylene or a radical of the formula (XU)
  • X is NR 5 and Y 1 to Y 3 , R 4 , n and R 5 have the meaning given above but are independent of it, can be substituted or
  • B as the basic structure on which the formula X is based preferably has the same meaning as A, the meanings A and B being independent of one another.
  • B is particularly preferably not substituted by a radical of the formula (XI) or (XII).
  • a and B independently of one another for 2-pyridyl, which can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, nitro or cyano,
  • 2-quinolyl which can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, nitro or cyano, l, 3-thiazol-2-yl, by up to two identical or different radicals can be substituted from the series chlorine, fluorine, methoxy, phenyl or cyano,
  • Benzthiazol-2-yl which consists of up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, 2,4-dimethyl-3-pentoxy, diisobutylaminosulfonyl, methoxycarbonyl, nitro or Cyano may be substituted
  • Benzoxazol-2-yl which consists of up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, 2,4-dimethyl-3-pentoxy, diisobutylaminosulfonyl, methoxycarbonyl, nitro or Cyano may be substituted
  • 3-H-indolin-2-yl which bears two methyl groups or an oxo group in position 3 and can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, methoxycarbonyl, nitro or cyano .
  • Isoindol-1-yl which can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, methoxycarbonyl, nitro or cyano and / or which is in position 3 by imino, dicyanomethylene, methoxycarbonyl-cyano- methylene, ethoxycarbonyl-cyano-methylene may be substituted, or 1,2,4-triazol-2-yl, which may be substituted by methyl or phenyl,
  • Quinolin-2-ylidene which can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, nitro or cyano, l, 3-thiazol-2-ylidene, which can be substituted by up to two identical or various residues from the series chlorine, fluorine, methoxy, phenyl or cyano can be substituted,
  • Benzthiazol-2-ylidene which is composed of up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, 2,4-dimethyl-3-pentoxy, di-isobutylaminosulfonyl, methoxycarbonyl, Nitro or cyano can be substituted,
  • Benzimidazol-2-ylidene which is formed by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, ethoxy, isobutoxy, 2,4-dimethyl-3-pentoxy, diisobutylaminosulfonyl, methoxycarbonyl, nitro or Cyano may be substituted, l, 3,4-thiadiazol-2-ylidene by chlorine, bromine, methoxy, phenoxy, methanesulfonyl, methylthio, ethylthio, dimethylamino, diethylamino, di- (iso) propylamino, N-methyl-N Cyanoethylamino, N, N-biscyanetyllylamino, N-methyl-N-hydroxyethylamino, N-methyl-N-benzylamino, N-methyl-N-phenylamino, anilino, pyrrolidino, piperidino
  • Isoindol-1-ylidene which can be substituted by up to two identical or different radicals from the series chlorine, fluorine, methyl, methoxy, methoxycarbonyl, nitro or cyano and / or which is in position 3 by imino, dicyanomethylene, methoxycarbonyl-cyano- methylene, ethoxycarbonyl-cyano-methylene can be substituted, or 1,2,4-triazol-2-ylidene which can be substituted by methyl or phenyl,
  • R 1 to R 4 independently of one another represent hydrogen, chlorine, methyl, benzyl, pyridylmethyl, phenyl, cyano, methoxycarbonyl or ethoxycarbonyl and
  • R 2 additionally represents methoxy, ethoxy, dimethylamino, diethylamino, pyrrolidino or piperidino, or
  • R 5 is methyl, ethyl, phenyl-, 2-, 3- or 4-pyridyl-, 2-, optionally substituted by up to two identical or different radicals from the series methyl, methoxy, chlorine, nitro, cyano, methylsulfonyl, methoxycarbonyl, ethoxycarbonyl , 3- or 4-quinolyl-, thiazol-2-yl-, benzthiazol-2-yl-, benzoxazol-2-yl-, imidazol-2-yl-, benzimidazol-2-yl-, l, 3,4- triazole-2- yl radicals, formyl, acetyl, trifluoroacetyl, acryloyl, methacryloyl, benzoyl, methylbenzoyl, chlorobenzoyl, methanesulfonyl, trifluoromethanesulfonyl, perfluorobutanesulfonyl
  • R 6 represents hydrogen, phenyl, cyano, methoxycarbonyl or ethoxycarbonyl
  • R 7 represents hydrogen, methyl, ethyl, phenyl, tolyl, chlorophenyl, anisyl, 2-pyridyl, thiazol-2-yl or benzthiazol-2-yl,
  • R 1 represents hydrogen, benzyl, phenyl, cyano methoxycarbonyl or ethoxycarbonyl
  • A represents a 2-pyridyl, l, 3-thiazol-2-yl, benzothiazol-2-yl or benzoxazol-2-yl radical which is represented by -0-CH 2 -CH (CH 3 ) 2 , -O-CH [CH (CH 3 ) 2 ] 2 , -OC (CH 3 ) 3 , -O-CH 2 -CH (C 2 H5) (C 4 H 9 ), -O-CH 2 -C (CH 3 ) 2 -C 2 H 5 , -SO 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -COOCH 2 CH 3 , -S0 2 NHCH 2 CH (CH 3 ) 2 , -SO 2 NHC (CH 3 ) 2 CH 2 CH 3 , -SO 2 NHC (CH 3 ) 3 , -CH 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -SO 2 NH- (CH 2 CH 2 CH 2 0-) 2
  • B represents a pyridin-2-ylidene, 1,3-thiazol-2-ylidene, benzothiazol-2-ylidene or benzoxazolidene-2-yl radical which is replaced by hydrogen, -O-CH 2 -CH (CH 3 ) 2 , -O-CH [CH (CH 3 ) 2 ] 2 , -OC (CH 3 ) 3 , -O-CH 2 -CH (C 2 H 5 ) (C 4 H 9 ), -O -CH 2 -C (CH 3 ) 2 -C 2 H 5 , -SO 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -COOCH 2 CH 3 , -SO 2 NHCH 2 CH (CH 3 ) 2 , -SO 2 NHC (CH 3 ) 2 CH 2 CH 3 , -SO 2 NHC (CH 3 ) 3 , -CH 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -S0
  • rings A and B are very particularly preferably identical.
  • R 1 represents hydrogen, benzyl, phenyl, cyano, methoxycarbonyl or ethoxycarbonyl
  • A represents a 2-pyridyl, 2-quinolyl or 3,3-dimethylindolin-2-yl radical which can be substituted by methyl, methoxy, chlorine or methoxycarbonyl,
  • B for a pyridin-2-ylidene, 1,3-thiazol-2-ylidene or benzothiazol-2-ylidene residue which can be substituted by chlorine, methyl, methoxy, cyano or methoxycarbonyl, 1,3,4- Thiadiazol-2-ylidene radical, which may be substituted by methylthio, dimethylamino, diethylamino, diisopropylamino, pyrrolidino or morpholino, or 1,3,4-triazol-2-ylidene radical.
  • R 1 represents hydrogen or cyano
  • A represents a 2-pyridyl, 2-quinolyl or 3,3-dimethylindolin-2-yl radical
  • B is a 1,3-thiazol-2-ylidene or benzothiazol-2-ylidene radical, 1,3-thiadiazol-2-ylidene radical which may be substituted by dimethylamino, diethylamino, diisopropylamino, pyrrolidino or morpholino , or l, 3,4-triazol-2-ylidene radical.
  • R 1 represents hydrogen, phenyl or cyano
  • R 2 represents hydrogen or
  • R 5 is phenyl, tolyl, chorphenyl, nitrophenyl, 2-, 3- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, trifluoroacetyl, methanesulfonyl, trifluoromethanesulfonyl, benzenesulfonyl, cyanobenzenesulfonyl, N, N-dimethylsulfamyl , Pyridine-2-, 3- or 4-sulfonyl,
  • A represents a 2-pyridyl, 2-quinolyl or 3,3-dimethylindolin-2-yl radical which can be substituted by methyl, methoxy, chlorine or methoxycarbonyl.
  • R 1 represents hydrogen
  • R 5 represents phenyl, tolyl, chorphenyl, nitrophenyl, 2-, 3- or 4-pyridyl, thiazol-2-yl or benzthiazol-2-yl,
  • A represents a 2-pyridyl, 2-quinolyl or 3,3-dimethylindolin-2-yl radical which can be substituted by methyl, methoxy, chlorine or methoxycarbonyl.
  • A represents a 2-pyridyl, 2-quinolyl or 3,3-dimethylindolin-2-yl radical which can be substituted by methyl, methoxy, chlorine or methoxycarbonyl.
  • R 1 represents hydrogen, benzyl, phenyl, cyano, methoxycarbonyl or ethoxycarbonyl
  • a 'for 3,4-tetramethylene-pyrrol-2-yl-5-ylidene, a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene residue, which is represented by methyl, methoxy, nitro or cyano can be substituted
  • B ' represents a 2-pyridyl, 2-quinolyl, 1,3-thiazol-2yl, benzthiazol-2-yl, benzoxazol-2-yl or 3,3-dimethylindolin-2-yl radical, which can be substituted by methyl, methoxy, chlorine, cyano or methoxycarbonyl,
  • R 1 represents hydrogen or cyano
  • a ' represents a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene radical which may be substituted by methyl or methoxy,
  • B ' represents a 2-pyridyl, l, 3-thiazol-2yl, benzthiazol-2-yl, benzoxazol-2-yl or 3,3-dimethylindolin-2-yl radical, which is represented by methyl, methoxy , Cyano or methoxycarbonyl may be substituted
  • B represents a pyridin-2-ylidene, 1,3-thiazol-2ylidene, benzothiazol-2-ylidene, benzoxazol-2-ylidene or 3,3-dimethylindolin-2-ylidene radical which is represented by methyl, Methoxy, cyano or methoxycarbonyl can be substituted
  • B represents a pyridin-2-ylidene, 1,3-thiazol-2ylidene, benzothiazol-2-ylidene, benzoxazol-2-ylidene or 3,3-dimethylindolin-2-ylidene radical which is represented by methyl
  • a 'for 3,4-tetramethylene-pyrrol-2-yl-5-ylidene, a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene residue, which is represented by methyl, methoxy, nitro or cyano can be substituted
  • B 'for a 2-pyridyl, 2-pyrimidyl, l, 3-thiazol-2yl, benzthiazol-2-yl, benzoxazol-2-yl radical which is substituted by methyl, methoxy, chlorine, cyano or methoxycarbonyl can be l, 3,4-triazol-2-yl or a l, 3,4-thiadiazol-2-yl radical which can be substituted by dimethylamino, diethylamino, diisopropylamino, pyrrolidino or morpholino,
  • B for a pyridin-2-ylidene, pyrimidin-2-ylidene, l, 3-thiazol-2ylidene, benzothiazol-2-ylidene, benzoxazol-2-ylidene residue which is characterized by methyl, methoxy, chlorine, cyano or may be substituted by methoxycarbonyl, l, 3,4-triazol-2-ylidene or a 1,3,4-thiadiazol-2-ylidene radical which may be substituted by dimethylamino, diethylamino, diisopropylamino, pyrrolidino or morpholino.
  • a ' represents a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene radical which may be substituted by methyl or methoxy,
  • a 'for 3,4-tetramethylene-pyrrol-2-yl-5-ylidene, a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene residue, which is represented by methyl, methoxy, nitro or cyano can be substituted
  • R 1 represents hydrogen
  • R 2 represents methoxy, ethoxy, dimethylamino, diethylamino, pyrrolidino or piperidino or
  • a ' represents a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene radical which may be substituted by methyl or methoxy,
  • R 1 represents hydrogen
  • R 2 represents dimethylamino, diethylamino, pyrrolidino or piperidino or
  • R 1 represents hydrogen or cyano
  • R 2 represents methoxy, ethoxy, dimethylamino, diethylamino, pyrrolidino or piperidino,
  • a ' represents a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene radical which may be substituted by methyl or methoxy,
  • R 1 represents hydrogen or cyano
  • R 2 represents dimethylamino, diethylamino, pyrrolidino or piperidino
  • B represents a pyridin-2-ylidene, 1,3-thiazole ⁇ 2ylidene, benzothiazol-2-ylidene, benzoxazol-2-ylidene or 3,3-dimethylindolin-2-ylidene residue which is represented by methyl, Methoxy, cyano or methoxycarbonyl can be substituted.
  • a 'for 3, 4-tetramethylene-pyrrol-2-yl-5-ylidene, a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene residue, which is represented by methyl, methoxy, nitro or cyano can be substituted
  • R 1 represents hydrogen or cyano
  • R 2 represents methoxy, ethoxy, dimethylamino, diethylamino, pyrrolidino or piperidino,
  • a ' represents a pyrrol-2-yl-5-ylidene or isoindol-1-yl-3-ylidene radical which may be substituted by methyl or methoxy,
  • R 1 represents hydrogen or cyano
  • R 2 represents dimethylamino, diethylamino, pyrrolidino or piperidino
  • B for a pyridin-2-ylidene, pyrimidin-2-ylidene, 1,3-thiazol-2ylidene, benzothiazol-2-ylidene, benzoxazol-2-ylidene residue which may be substituted by methyl, methoxy or cyano may be l, 3,4-triazol-2-ylidene or a l, 3,4-thiadiazol-2-ylidene radical, which may be substituted by dimethylamino or diisopropylamino.
  • alkyl, alkenyl or aralkyl radicals in the context of this application are preferably halogen, in particular Cl or F, mono- or dialkylamino radicals, pyrrolidino, morpholino, piperidino, nitro, cyano, CO-NH2, alkoxy, trialkylsilyl or Trialkylsiloxy in question.
  • the alkyl radicals can be straight-chain or branched and they can be partially or perhalogenated. Examples of substituted alkyl radicals are trifluoromethyl, chloroethyl, cyanoethyl, methoxyethyl. Examples of branched alkyl radicals are isopropyl, tert-butyl, 2-butyl or neopentyl.
  • Preferred optionally substituted C1-C12-alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, n-hexyl, 2-ethyl-hexyl, 2 , 4-dimethyl-3-pentyl, 2,2-dimethyl-butyl, trifluoromethyl, perfluorinated ethyl, 2,2-difluoroethyl, 3,3,3-trifluoroethyl, perfluorobutyl, cyanoethyl, methoxyethyl, chloroethyl, bis-isobutylamino, bis- tert-pentylamino, morpholino.
  • Ci-Cg-alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, h-hexyl,, cyanoethyl, methoxyethyl or chloroethyl.
  • These alkyl residues are also contained in the preferred optionally substituted C 1 -C 2 -alkoxy residues.
  • preferred aralkyl is preferably, for example, benzyl, phenethyl or phenylpropyl.
  • Allyl or 2-buten-1-yl is an example of a preferred alkenyl.
  • Preferred heterocyclic radicals or hetaryl radicals are pyridyl, thiazolyl, benzthiazolyl.
  • acyl groups are preferably formyl, C 2 -C 6 alkanoyl, C 3 -C 6 alkenoyl, C 6 -C 10 aroyl, CC ö -alkylsulfonyl, C 6 -arylsulfonyl -C ⁇ 0, C C ⁇ -alkoxycarbonyl, mono- or to understand C 1 -C 6 alkylamino carbonyl, mono- or di C 1 -C 6 alkylamino sulfonyl or a heterocyclic radical attached via a CO or S0 2 group, which in turn can be optionally substituted.
  • Examples are formyl, acetyl, trifluoroacetyl, acryloyl, methacryloyl, benzoyl, methylbenzoyl, chlorobenzoyl, methanesulfonyl, trifluoromethanesulfonyl, perfluorobutanesulfonyl, benzene sulfonyl, toluenesulfonyl, chlorobenzenesulfonyl, methoxycarbonyl, ethoxycarbonyl, dimethyl- carbamoyl, dimethylsulfamoyl, pyridin-2-, 3- or 4-carbonyl, pyridine-2-, 3- or 4-sulfonyl, benzothiazole-2-sulfonyl, pyrimidine-2-sulfonyl, -S0 2 N (CH2CH (CH 3 ) 2) 2J -COOCH 2 CH 3 , -S0 2 NHCH 2 CH
  • the particularly preferred metal complexes of the formula (Ia) with ligands of the formulas (IA) to (IJ) and (IQ) to (IN) each have 2 ligands as they have a tautomeric form of the formulas (ILA) to (JT-K) and (JT-Q) to (Tf-V) can be removed. It is assumed that they are in the form of the formulas (I A) to (JT-K) and (JT-Q) to (Ü-V):
  • the particularly preferred metal complexes of the formula (Ib) with ligands of the formulas (IK) to (IP) and (IW) to (I-ZA) each have 1 ligand of the formulas (ULK) to (IH- P) and (TH-W) to (HI-ZA) can be removed. It is assumed that they are in the form of the formulas (IH-K) to (IH-P) and (TH-W) to (HI-ZA):
  • All monovalent anions or an equivalent of a polyvalent anion or an equivalent of an oligomeric or polymeric anion are suitable as anions An " . They are preferably colorless anions. Suitable anions are, for example, chloride, bromide, iodide, nitrate, tetrafluoroborate, perchlorate, Hexafluorosilicate, hexafluorophosphate, methosulfate, ethosulfate, C cio-alkanesulfonate, C r C ⁇ o-perfluoroalkanesulfonate, optionally substituted by chlorine, hydroxy, C ⁇ -C - alkoxy Cio-alkanoate, optionally by nitro, cyano, hydroxy, C ⁇ -C 25 - Alkyl, perfluoro-C 4 alkyl, C 1 -C alkoxycarbonyl or chlorine substituted benzene or naphthalene or biphenyl sulfonate
  • the anionic dye An " preferably has an absorption spectrum similar to that of the cationic metal complex salt. Suitable examples are anionic azo dyes, anthraquinone dyes, porphyrins, phthalocyanines, subphthalocyanines, cyanines, merocyanines, rhodamines, metal complexes, oxonols and derivatives of flavonic acid.
  • M stands for Pd, Fe, Zn, Cu, Ni or Co and
  • the other radicals have the meanings which are particularly preferred and very particularly preferred above under the formulas (IA) to (IC), (IG), (IH), (IJ), (IK), (IQ), (IR) and (IU) own, with each formula being particularly preferred in itself.
  • Metal complexes of the formula (Ib), in particular of the formulas (ffl-), (LTJ-L), (HI-O), (IH-W) and (H-X), are also very particularly preferred,
  • M represents Pd, Fe, Zn, Cu, Ni or Co
  • metal complexes of the formulas (H-A) to (H-K) and (H-Q) to (H-V) are:
  • metal complexes of the formulas (HI-K) to (IH-P) and (IH-W) to (HI-ZA) are:
  • 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., but at least greater than 200 ° C.
  • Such a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
  • those metal complexes are preferred as light-absorbing compounds whose absorption maximum ⁇ m M ⁇ is in the range from 340 to 410 nm , where the wavelength ⁇ 2 , at which the extinction in the short-wave flank of the absorption maximum of wavelength ⁇ max i is half the extinction value at ⁇ maxl , and the wavelength ⁇ / ⁇ o, at which the absorbance in the short-wave flank of the absorption maximum of the wavelength ⁇ max i is one tenth of the absorbance value at ⁇ max i, preferably not more than 50 nm apart.
  • Such a metal complex preferably does not have a longer-wave maximum X ⁇ n a up to a wavelength of 500 nm, particularly preferably up to 550 nm, very particularly preferably up to 600 nm.
  • the metal complexes ⁇ m and ⁇ yio, 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.
  • metal complexes are preferred as light-absorbing compounds whose absorption maximum ⁇ ma ⁇ is in the range 420 to 550 nm, the Wavelength ⁇ / 2 , at which the extinction in the short-wave flank of the absorption maximum of wavelength m ⁇ is half the extinction value at ⁇ max2 , and the wavelength ⁇ y ⁇ 0 , at which the extinction in the short-wave flank of the absorption maximum of wavelength ⁇ max2 is one tenth of the extinction value at ⁇ ma ⁇ , preferably not more than 80 nm apart.
  • Such a metal complex preferably does not have a shorter-wave maximum ⁇ maxx up to a wavelength of 350 nm, particularly preferably up to 320 nm, very particularly preferably up to 290 nm.
  • Metal complexes with an absorption maximum ⁇ m ⁇ of 430 to 550 nm, in particular 440 to 530 nm, very particularly preferably 450 to 520 nm are preferred.
  • the metal complexes ⁇ / 2 and ⁇ W are preferably not more than 70 nm apart, more preferably not more than 50 nm apart, very particularly preferably not more than 40 nm apart.
  • the metal complexes preferably have a molar extinction coefficient ⁇ > 30,000 l / mol cm, preferably> 50,000 l / mol cm, particularly preferably> 70,000 l / mol cm, very particularly preferably> 100,000 l / mol cm ,
  • the absorption spectra are measured, for example, in solution.
  • Suitable metal complexes with the preferred spectral properties are, in particular, those which have a low solvatochromism (dioxane / DMF or methylene chloride / methanol).
  • , ie the positive difference of the absorption wavelengths in the solvents dimethylformamide and dioxane, or their solvatochromism ⁇ MM
  • the optical data carrier according to the invention which is written and read with the light of a blue laser, is preferred.
  • the laser wavelength is preferably in the range from 360 to 460 nm, particularly preferably in the range from 390 to 420 nm, very particularly preferably in the range from 400 to 410 nm.
  • the laser optics preferably have a numerical aperture NA> 0.6, particularly preferably> 0 , 7, very particularly preferably> 0.8.
  • the optical data carrier is preferably written and read at the same wavelength.
  • the metal complexes used according to the invention guarantee a sufficiently high reflectivity (preferably> 10%, in particular> 20%) 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 of 360 up to 460 nm.
  • the contrast between written and unwritten points on the data carrier is realized by the change in reflectivity of the amplitude as well as the phase of the incident light by the optical properties of the information layer that have changed after thermal degradation.
  • the k value (imaginary part of the complex refractive index) of the formation layer, consisting of the metal complexes used according to the invention is preferably in the range from 0.01 to 0.40, preferably in the range from 0.01 to 0.30, particularly preferably in the range from 0.01 to 0.20.
  • the n-value (real part of the complex refractive index) of the information layer, consisting of the metal complexes used according to the invention is preferably in the range from 0.9 to L3 or 1.7 to 2.8, preferably in the range from 0.9 to 1.2 or 1.8 to 2.8, particularly preferably in the range from 0.9 to 1.1 or 1.9 to 2.8.
  • the metal complexes according to the invention are preferably applied to the optical data carrier by spin coating or vacuum evaporation, in particular spin coating. Spin coating is carried out from solution or dispersion.
  • the metal complexes according to the invention can be mixed with one another or with other dyes with similar spectral properties.
  • the information layer can contain additives such as binders, wetting agents, stabilizers, thinners and sensitizers and further constituents.
  • the solutions of the metal complexes listed above are preferably used for spin coating.
  • the information layer preferably consists of at least 70%, preferably at least 85%, particularly preferably at least 95%, very particularly preferably 100% of a metal complex according to the invention.
  • the optical data storage device can carry further layers such as metal layers, dielectric layers, protective layers and cover layers.
  • Metals and dielectric layers serve among other things to adjust the reflectivity and the heat balance. Depending on the laser wavelength, metals can be gold, silver, aluminum, etc. his.
  • Dielectric layers are, for example, silicon dioxide and silicon nitride.
  • Protective layers or cover layers are, for example photocurable lacquers, (pressure-sensitive) adhesive layers and protective films.
  • Silicon dioxide and silicon nitride are applied, for example, by so-called reactive sputtering.
  • the layer thicknesses are, for example, in the range from 1 nm to 40 nm.
  • the metal layers are applied, for example, by sputtering.
  • the layer thicknesses are, for example, in the range from 10 to 180 nm.
  • Pressure-sensitive adhesive layers mainly consist of acrylic adhesives. Nitto Denko DA-8320 or DA-8310, disclosed in patent JP-A 11-273147, for example, can be used for this purpose.
  • Protective films are preferably made of translucent material, preferably plastic films. Suitable materials are, for example, polycarbonate, copolycarbonates, PMMA and cyclic polyolefins.
  • the thickness is, for example, 5 to 200 ⁇ m, preferably 10 to 180 ⁇ m, particularly preferably 20 to 150 ⁇ m, very particularly preferably 50 to 120 ⁇ m.
  • Photocurable lacquers are, for example, UV-curable lacquers. These are, for example, acrylates and methacrylates, such as those from P.K.T. Oldring (Ed.), Chemistry & Technology of UV & EB Formulations for Coatings, Inks & Paints, Vol. 2, 1991, SITA Technology, London, pp. 31-235 are known.
  • the thickness is, for example, 5 to 200 ⁇ m, preferably 10 to 180 ⁇ m, particularly preferably 20 to 150 ⁇ m, very particularly preferably 50 to 120 ⁇ m.
  • the optical data carrier preferably contains at least one substrate.
  • the substrate material is preferably transparent. Its thickness is at least 0.3 mm, preferably at least 0.6 mm and very particularly preferably at least 1.1 mm.
  • Suitable substrate materials are preferably transparent thermoplastics or thermosets. Suitable thermoplastics are, for example, polycarbonate, copolycarbonates, PMMA and cyclic polyolefins.
  • the optical data carrier according to the invention has, for example, the following layer structure (cf. FIG. 1): a preferably transparent substrate (1), optionally a reflection layer (7), optionally a protective layer or dielectric layer (2), an information layer (3), optionally one Protective layer or dielectric layer (4), optionally an adhesive layer (5), a cover layer (6).
  • the arrows shown in Fig. 1 and Fig. 2 represent the path of the incident light.
  • the structure of the optical data carrier can preferably include: a preferably transparent substrate (1), on the surface of which at least one information layer (3) which can be written on with light and which can be written on with light, preferably laser light, optionally a protective layer or dielectric 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 reflection layer (7), at least one information layer (3) which can be written on with light and which can be written on with light, preferably laser light, optionally a protective layer or dielectric layer (4), optionally one Adhesive layer (5), and a transparent cover layer (6) are applied.
  • a preferably transparent substrate (1) on the surface of which a protective layer or dielectric layer (2), at least one information layer (3) which can be rubbed with light, preferably laser light, optionally an adhesive layer (5), and a transparent cover layer (6) are applied are.
  • a preferably transparent substrate (1) on the surface of which a protective layer or dielectric layer (2), a reflection layer (7), at least one information layer (3) which can be written on with light, preferably laser light, optionally a protective layer or dielectric 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 there is optionally a protective layer or dielectric layer (2), at least one information layer (3) that can be written on with light, preferably laser light, optionally a protective layer or dielectric 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 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 can have, for example, the following layer structure (cf. FIG. 2): a preferably transparent substrate (11), an information layer (12) that can be written on with light, preferably laser light, optionally a reflection layer (13), optionally one Adhesive layer (14), another preferably transparent substrate (15).
  • the optical data carrier preferably contains an information layer (3) or (12).
  • the optical data carrier likewise preferably contains a reflection layer (7) or (13).
  • the optical data carrier likewise preferably contains a transparent cover layer (6).
  • the optical data carrier likewise preferably contains a substrate (1) or (11) or (15) made of polycarbonate or copolycarbonate.
  • the substrate (1) likewise preferably has a thickness of 0.3 to 1.5 mm, preferably 0.5 to 1.2 mm, in particular 1.1 mm.
  • the substrate (11) and (15) likewise preferably has a thickness of 0.3 to 1.5 mm, preferably 0.5 to 1.2 mm, in particular 0.6 mm.
  • the structure of the optical data carrier is particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a reflection layer (7), an information layer (3) which can be written and read with light, preferably laser light, a protective layer or dielectric layer (4), an adhesive layer (5), and a transparent cover layer (6) are also applied.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a reflection layer (7), an information layer (3) that can be written and read with light, preferably laser light, a protective layer or dielectric layer (4), and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a reflection layer (7), an information layer (3) which can be written and read with light, preferably laser light, and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a reflection layer (7), a protective layer or dielectric layer (2), an information layer (3) which can be written and read with light, preferably laser light, a protective layer or dielectric layer (4), a Adhesive layer (5), and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a reflection layer (7), a protective layer or dielectric layer (2), an information layer (3) which can be written and read with light, preferably laser light, a protective layer or dielectric layer (4), and a transparent cover layer (6) is applied.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a reflection layer (7), a protective layer or dielectric layer (2), an information layer (3) which can be written and read with light, preferably laser light, and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is also particularly preferred as follows: a transparent substrate (1), on the surface of which a protective layer or dielectric layer (2), an information layer (3) which can be written and read with light, preferably laser light, a protective layer or dielectric layer (4), an adhesive layer (5), and a transparent cover layer (6) is applied.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a protective layer or dielectric layer (2), an information layer (3) which can be written and read with light, preferably laser light, a protective layer or dielectric layer (4), and a transparent cover layer (6) are upset.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate (1) on the surface of which a protective layer or dielectric layer (2), an information layer (3) which can be written and read with light, preferably laser light, and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is also particularly preferred as follows:
  • a transparent substrate 11
  • an information layer (12) which can be written and read with light, preferably laser light
  • a reflection layer 13
  • an adhesive layer 14
  • a further transparent substrate 15
  • the invention also relates to optical data carriers which contain two information layers.
  • they can be constructed as follows: - a cover layer (6), optionally an adhesive layer (5), optionally a protective layer or dielectric layer (4), an information layer (3), optionally a protective layer or dielectric layer (2), optionally a reflection - Layer (7), a transparent substrate (1), optionally a reflection layer (7), optionally a protective layer or dielectric layer (2), an information layer (3), optionally a protective layer or dielectric layer (4), optionally one Adhesive layer (5), a cover layer (6).
  • optical data carriers with two information layers can also contain all of the preferred layer structures listed above in an analogous manner.
  • the invention further relates to optical data carriers according to the invention described with blue light, in particular laser light.
  • the invention further relates to a method for producing the optical data carrier according to the invention, which is characterized in that a preferably transparent substrate, optionally already coated with a reflection layer, with at least one metal complex as the light-absorbing compound and having at least one ligand of the formula (I), optionally coated in combination with suitable binders and additives and optionally solvents and optionally provided with a reflection layer, further intermediate layers and optionally a protective layer or a further substrate or a covering layer.
  • the invention further relates to metal complexes which have at least one ligand of the formula (I), in which the rest of the formula
  • Metal complexes which contain at least one ligand of the formula (I-A), (IB), (ID) to (IL), (IN) to (IR), (T) to (IX), (LZ) and.
  • I-ZA is particularly preferred
  • a 'and B has at least one substituent from the series of the branched C 3 -C 8 alkoxy radicals, for example -0 -CH 2 -CH (CH 3 ) 2 , -0-CH [CH (CH 3 ) 2 ] 2 , -0-C (CH 3 ) 3 , -0-CH2-CH (C 2 H 5 ) (C 4 H 9 ), -0-CH 2 -C (CH 3 ) 2 -C 2 H 5 , of the branched or ring-closed C 2 -C 8 alkylamomethylene residues, for example CH 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -
  • the optionally branched C 2 -C 5 alkoxycarbonyl radicals for example -COOCH 2 CH 3 , -COO-CH (CH 3 ) 2 , -COO-CH [CH (CH 3 ) 2 ] 2
  • the optionally branched or ring-closed C 2 - C 8 alkylaminosulfonyl radicals for example -S0 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -S0 2 NHCH 2 CH (CH 3 ) 2 , -S0 2 NHC (CH 3 ) 2 CH 2 CH 3 , -S0 2 NHC (CH 3 ) 3 , -S0 2 NH- (CH 2 CH 2 CH 2 0-) 2 CH 3 ,
  • the optionally branched C 2 -C 5 alkoxycarbonyl radicals for example -COOCH2CH3, -COO-CH (CH 3 ) 2 , -COO-CH [CH (CH 3 ) 2 ] 2
  • the optionally branched or ring-closed C 2 -C 8 -Alkylaminosulfonylreste for example -S0 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -S0 2 NHCH 2 CH (CH 3 ) 2 , -S0 2 NHC (CH 3 ) 2 CH 2 CH 3 , -S0 2 NHC (CH 3 ) 3 , -S0 2 NH- (CH 2 CH 2 CH 2 0-) 2 CH 3 ,
  • Metal complexes of the formulas (HD) to (HK), (HQ), (Tf-R), (HT) to (HV), (HI-L), (HI-N) to (IH-P) are very particularly preferred.
  • (IH-W), (HI-X), (HI-Z) and (HI-ZA) as specified above as examples.
  • the metal complexes according to the invention are marketed in particular as powders or granules or as a solution, the latter preferably with a solids content of at least 2% by weight.
  • the granulate form is preferred, in particular granules with an average particle size of 50 ⁇ m to 10 mm, in particular 100 to 800 ⁇ m.
  • Such granules can be produced, for example, by spray drying.
  • the granules are particularly characterized by their low dust level.
  • the metal complexes according to the invention are notable for good solubility. They are readily soluble in non-fluorinated alcohols. Such alcohols are, for example, those having 3 to 6 carbon atoms, preferably propanol, butanol, pentanol, hexanol, diacetone alcohol or also mixtures of these alcohols, such as, for example, propanol / diacetone alcohol, butanol / diacetone alcohol, Butanol / hexanol.
  • Preferred mixing ratios for the listed mixtures are, for example, 80:20 to 99: 1, preferably 90:10 to 98: 2.
  • the solution particularly preferably consists of more than 95% by weight, in particular more than 98% by weight, of components a) and b).
  • the invention further relates to a process for the preparation of the metal complexes according to the invention, which is characterized in that a metal salt with a ligand compound of the formula (Id)
  • A represents an optionally substituted and / or benzyl or naphthane-fused five- or six-membered aromatic or quasi-aromatic or partially hydrogenated heterocyclic radical
  • n 0 or 1
  • Y 1 represents N or CR 1
  • Y 2 represents N or CR 2 ,
  • Y 3 represents N or CR 3 .
  • X represents O, S or NR 5 ,
  • R 5 represents hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl, acyl, aryl or a heterocyclic radical
  • R 1 to R 4 independently of one another represent hydrogen, halogen, alkyl, alkoxy, mono- or dialkylamino, aralkyl, aryl, hetaryl, arylazo, hetarylazo, cyano or alkoxycarbonyl,
  • R *; R 2 can form an optionally substituted and / or optionally containing heteroatoms triatomic bridge or an optionally substituted fouratoms bridge which contains no or at least 2 heteroatoms,
  • R; R 3 and R 4 ; R 5 can each independently form a bridge and
  • R 2 ; R 5 can form a bridge if n stands for 0,
  • Two or more different ligand compounds of the formula (Id) can also be used in this process according to the invention.
  • a statistical mixture of metal complexes which contain two identical ligands of the formula (I) and those complexes which contain two different ligands of the formula (I) is then obtained. These mixtures are also the subject of the invention.
  • the reaction according to the invention is generally carried out in a solvent or solvent mixture, if appropriate in the presence of basic substances, at room temperature to the boiling point of the solvent, for example at 20-100 ° C., preferably at 20-50 ° C.
  • the metal complexes usually either precipitate directly and can be isolated by filtration or they are precipitated, for example, by adding water, possibly with partial or complete removal of the solvent beforehand, and isolated by filtration. It is also possible to carry out the reaction directly in the solvent to give the concentrated solutions mentioned above.
  • Metal salts include, for example, chlorides, bromides, sulfates, hydrogen sulfates, phosphates, hydrogen phosphates, dihydrogen phosphates, hydroxides, oxides, carbonates, hydrogen carbonates, salts of carboxylic acids such as formates, acetates, propionates, benzoates, salts of sulfonic acids such as methanesulfonates, trifluoromethanesulfonates or to understand benzenesulfonates of the corresponding metals.
  • Metal salts are also to be understood as meaning complexes with ligands other than those of the formulas (Ia), in particular complexes of acetylacetone and acetoacetic acid esters.
  • suitable metal salts are: nickel acetate, cobalt acetate, copper acetate, nickel chloride, nickel sulfate, cobalt chloride, copper chloride, copper sulfate, nickel hydroxide, nickel oxide, nickel acetylacetonate, cobalt hydroxide, basic copper carbonate, barium chloride, iron sulfate, palladium acetate, palladium chloride and their variants containing water of crystallization.
  • the acetates of the metals are preferred.
  • the metals of the underlying metal salts are preferably divalent.
  • Alkali acetates such as e.g. Sodium acetate, potassium acetate, alkali hydrogen carbonates, carbonates or hydroxides such as e.g. Sodium hydrogen carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, or amines such as e.g. Ammonia, dimethylamine, triethylamine, diethanolamine.
  • metal salts of strong acids such as e.g. the metal chlorides or sulfates are used.
  • Suitable solvents are water, alcohols such as e.g. Methanol, ethanol, propanol, butanol, 2,2,3,3-tetrafluoropropanol, ethers such as dibutyl ether, dioxane or tetrahydrofuran, aprotic solvents such as e.g. Dimethylformamide, N-methylpyrrolidone, acetonitrile, nitromethane, dimethyl sulfoxide. Methanol, ethanol and 2,2,3,3-tetrafluoropropanol are preferred.
  • alcohols such as e.g. Methanol, ethanol, propanol, butanol, 2,2,3,3-tetrafluoropropanol
  • ethers such as dibutyl ether, dioxane or tetrahydrofuran
  • aprotic solvents such as e.g. Dimethylformamide, N-methylpyrrolidone, acetonitrile,
  • the vinylogenic amidines and amides, hereinafter called ligand compounds, of the formula (Id) required for the preparation of the metal complexes according to the invention are also the subject of this invention.
  • the invention further relates to the use of the metal complexes according to the invention as light-absorbing compounds in the information layer of write-once optical data carriers which can be written and read with blue light with a wavelength in the range from 360-460 nm, in particular laser light.
  • the invention also relates to ligand compounds of the formula (Id)
  • A represents an optionally substituted and / or benzyl or naphthane-fused five- or six-membered aromatic or quasi-aromatic or partially hydrogenated heterocyclic radical
  • n 0 or 1
  • Y 1 represents N or CR 1 ,
  • Y 2 represents N or CR 2 ,
  • Y 3 represents N or CR 3 .
  • X represents O, S or NR 5 ,
  • R 5 represents hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl, acyl, aryl or a heterocyclic radical
  • R 1 to R 4 independently of one another represent hydrogen, halogen, alkyl, alkoxy, mono- or dialkylamino, aralkyl, aryl, hetaryl, arylazo, hetarylazo, cyano or alkoxycarbonyl,
  • R X ; R 2 can form an optionally substituted and / or optionally containing triatomic bridge or an optionally substituted four-atom bridge which contains no or at least 2 heteroatoms,
  • R 2 ; R 3 and R 4 ; R 5 can each independently form a bridge and
  • R 2 ; R 5 can form a bridge when n is 0 and in which the rest of the formula
  • Preferred ligand compounds correspond to the protonated form of at least one of the formulas (IA), (IB), (ID) to (IL), (IN) to (IR), (LT) to (IX), (LZ) and (I-ZA ) or a tautomeric form thereof, wherein in formula (IA) and (IB) at least one of the rings A and B at least one substituent from the series of branched C 3 -C 8 alkoxy radicals, for example -0-CH 2 -CH (CH 3 ) 2 , -0-CH [CH (CH 3 ) 2 ] 2 , -0-C (CH 3 ) 3 , -0-CH 2 -CH (C 2 H 5 ) (C 4 H 9 ),
  • the optionally branched C 2 -C 5 alkoxycarbonyl radicals for example -COOCH2CH3, -COO-CH (CH 3 ) 2 , -COO-CH [CH (CH 3 ) 2 ] 25
  • the optionally branched or ring-closed C 2 -C 8 alkylaminosulfonyl radicals for example, -S0 2 N (CH 2 CH (CH 3 ) 2 ) 2 , -S0 2 NHCH 2 CH (CH 3 ) 2 , -S0 2 NHC (CH 3 ) 2 CH 2 CH 3 , -S0 2 NHC (CH 3 ) 3 , -S0 2 NH- (CH 2 CH 2 CH 2 0-) 2 CH 3 ,
  • Ligand compounds of the formula (Id) can be prepared analogously to J. Org. Chem. 2002, 67, 5753, Khim. Geterotsycl. Soedin. 2 (1966) 506, Pharm. Chem. J. (Engl. Transl.) 7 (1973) 199, Z. Electrochem. 64 1960) 720, Gazz. Chim. Ital. 124 (1994) 301 or according to CR Hebd. Seance Acad. Be. 240 (1955) 983, J. Chem. Soc. Perkin Trans. H, 19842111.
  • all combinations of the above disclosed general ranges and the preferred ranges and the preferred range apply to each other as revealed ago ⁇ preferred ranges.
  • UV (CH 2 C1 2 ): ⁇ ⁇ 359, 376 nm.
  • UV (CH 2 C1 2 ): 365, 376 nm.
  • the corresponding cobalt complex could be prepared in an analogous manner.
  • UV (CH 2 C1 2 ): ⁇ ⁇ 363, 378 nm.
  • UV (CH 2 C1 2 ): ⁇ ⁇ 455 nm.
  • Example 3a 2.49 gl, l-bis- (methylthio) -2-cyano-3-phenyl-l-propen-3-one and 1.25 g of o-aminothiophenol were stirred in 60 ml of ethanol for 6 hours under a nitrogen atmosphere , After cooling, the product was filtered off with suction, washed with a little ethanol and dried at 50 ° C. in vacuo. 2.4 g (86% of theory) of a colorless powder of the formula were obtained
  • UV (CH 2 C1 2 ): ⁇ ,,,, « 362 nm.
  • UV (CH 2 C1 2 ): ⁇ 453, 501 nm.
  • a 3% by weight solution of the dye from Example 1 in 2,2,3,3-tetrafluoropropanol was prepared at room temperature. This solution was applied to a pregrooved polycarbonate substrate using spin coating.
  • the pregrooved polycarbonate substrate was produced by injection molding as a disc with a diameter of 12 cm and a thickness of 0.6 mm, and the track pitch of the groove structure was 740 nm.
  • the disc with the dye layer as information carrier was sputtered with 100 nm of silver.
  • a UV-curable acrylic varnish was then applied by spin coating and a second identical polycarbonate substrate was applied. By further spinning, the acrylic varnish is homogeneously distributed over the disk surfaces and then cured using a UV lamp.
  • the write power was applied as an oscillating pulse sequence (see FIG. 3), the disk being alternately irradiated with the above-mentioned write power P w ⁇ 7e and the read power P rea d «1.9 mW.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Indole Compounds (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

L'invention concerne des supports de données optiques qui contiennent un substrat de préférence transparent, éventuellement déjà recouvert d'au moins une couche réfléchissante, sur la surface duquel sont appliqués une couche d'informations sur laquelle des données peuvent être écrites au moyen d'un rayon lumineux, éventuellement au moins une couche réfléchissante et, éventuellement, une couche protectrice ou un autre substrat, ou une couche de couverture, sur lesquels on peut écrire des données et à partir desquels on peut lire des données, cela à l'aide d'une lumière bleue, de préférence d'une lumière d'une longueur d'onde comprise dans la plage 360-460 nm, en particulier 390-420 nm, mieux encore de 400 à 410 nm, et de préférence au moyen d'une lumière laser. Dans ce support de données optiques, la couche d'informations comporte un composé absorbant la lumière et, éventuellement un liant. Ce support de données optiques se caractérise en ce que le composé absorbant la lumière qu'il contient est constitué d'au moins un complexe métallique qui comporte au moins un ligand correspondant à la formule (I), dans laquelle: (A) représente un reste hétérocyclique éventuellement substitué et/ou à annélation du benzène ou du naphtane, à 5 ou 6 éléments, aromatiques ou quasi-aromatiques ou partiellement hydrogénés; n représente 0 u 1; Y<1> représente N ou C-R<1>; Y<2 >représente N ou C-R<2>; Y<3 >représente N ou C-R<3>; X représente O, S ou N-R<5>; R<5 >représente hydrogène, alkyle, alcényle, aralkyle, cycloalkyle, acyle, aryle, ou un reste hétérocyclique; R<1> à R<4> représentent indépendamment l'un de l'autre, hydrogène, halogène, alkyle, alcoxy, monoalkylamino ou dialkylamino, aralkyle, aryle, hétaryle, arylazo, hétarylazo, cyano ou alcoxycarbonyle; R<1>; R<2>, R<2>; R<3> et R<4>; R<5> pouvant former, indépendamment les uns des autres, respectivement un pont et R<2>; R<5> pouvant également former un pont, cela quand n représente 0.
EP05700952A 2004-01-20 2005-01-15 Complexes metalliques utilises comme composes absorbant la lumiere dans la couche d'informations de supports de donnees optiques Withdrawn EP1709039A1 (fr)

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DE102004002758A DE102004002758A1 (de) 2004-01-20 2004-01-20 Metallkomplexe als lichtabsorbierende Verbindungen in der Informationsschicht von optischen Datenträgern
PCT/EP2005/000362 WO2005068459A1 (fr) 2004-01-20 2005-01-15 Complexes metalliques utilises comme composes absorbant la lumiere dans la couche d'informations de supports de donnees optiques

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JP4961789B2 (ja) * 2006-03-22 2012-06-27 三菱化学株式会社 光学記録媒体及びその記録層形成用色素
US20090252013A1 (en) * 2006-08-08 2009-10-08 Mitsubishi Chemical Corporation Hydrazide chelate complex compound, optical recording medium using the compound and recording method thereof
CA2786425C (fr) 2010-01-19 2016-12-20 Sumitomo Seika Chemicals Co., Ltd. Composition pour element resorbable aux rayons ultraviolets, et element resorbable aux rayons ultraviolets comprenant celle-ci
JP2014101394A (ja) * 2011-03-11 2014-06-05 Sumitomo Seika Chem Co Ltd 紫外線吸収部材用組成物およびこれを用いた紫外線吸収部材
CN103044491B (zh) * 2012-12-23 2015-05-13 延安常泰药业有限责任公司 甲醇与二氧化碳合成碳酸二甲酯的方法
CN104744351B (zh) * 2014-09-30 2017-06-06 三峡大学 一种小分子抑制剂及在抑制鸟氨酸脱羧酶(odc)上的应用
CN104725407B (zh) * 2015-03-09 2016-08-17 天津师范大学 一维链状手性Zn(Ⅱ)荧光配合物及其水热合成方法与荧光探针应用
CN104744498B (zh) * 2015-03-09 2016-06-22 天津师范大学 具有一维链状结构的偶氮三唑-Zn(Ⅱ)配合物及其合成方法与应用
JPWO2024043147A1 (fr) * 2022-08-25 2024-02-29

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TW200538454A (en) 2005-12-01
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WO2005068459A1 (fr) 2005-07-28
JP2007535421A (ja) 2007-12-06

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