EP1556445A2 - Complexes metalliques utilises comme composes photoabsorbants dans la couche d'information de supports de donnees optiques - Google Patents

Complexes metalliques utilises comme composes photoabsorbants dans la couche d'information de supports de donnees optiques

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Publication number
EP1556445A2
EP1556445A2 EP03766171A EP03766171A EP1556445A2 EP 1556445 A2 EP1556445 A2 EP 1556445A2 EP 03766171 A EP03766171 A EP 03766171A EP 03766171 A EP03766171 A EP 03766171A EP 1556445 A2 EP1556445 A2 EP 1556445A2
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EP
European Patent Office
Prior art keywords
optionally substituted
formula
alkyl
methyl
independently
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.)
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Application number
EP03766171A
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German (de)
English (en)
Inventor
Horst Berneth
Friedrich-Karl Bruder
Rainer Hagen
Karin HASSENRÜCK
Serguei Kostromine
Christa Maria KRÜGER
Timo Meyer-Friedrichsen
Rafael Oser
Josef-Walter Stawitz
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Lanxess Deutschland GmbH
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Lanxess Deutschland GmbH
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Publication date
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Publication of EP1556445A2 publication Critical patent/EP1556445A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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

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 metal complexes, a process for their production, the azo compounds functioning as ligands of the metal complexes and their production, the coupling components on which the azo compounds are based and their production, and optical data memories which contain the metal complexes in their information layer.
  • the write-once optical data carriers using special light-absorbing substances or their mixtures are particularly suitable for use in high-density writable optical data storage devices that work with blue laser diodes, in particular GaN or SHG laser diodes (360 - 460 ⁇ m) and / or for use with DVD-R or CD-R discs that work with red (635 - 660 nm) or infrared (780 - 830 nm) laser diodes.
  • the 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 the DVD-R.
  • the patent literature describes dye-based writable optical data memories which are equally suitable for CD-R and DVD-R systems (JP-A 11 043 481 and JP-A 10 181 206).
  • JP-A 11 043 481 and JP-A 10 181 206 For a high reflectivity and a high modulation level of the readout signal, as well as for a sufficient sensitivity when writing, use is made of the fact that the IR wavelength 780 nm of the CD-R lies at the foot of the long-wave flank of the absorption peak of the dye.
  • the red wavelength 635 nm or 650 nm of the DVD-R lies at the foot of the short-wave flank of the absorption peak of the dye.
  • the writable information layer made of light-absorbing organic substances must have a morphology which is as amorphous as possible in order to keep the noise signal as small as possible when writing or reading.
  • the substances are applied by spin coating from a solution, by vapor deposition and / or sublimation, subsequent crystallization of the light-absorbing substances with metallic or dielectric layers in vacuum is prevented.
  • the amorphous layer of light-absorbing substances should preferably have a high heat resistance, since otherwise further layers of organic or inorganic material, which are applied to the light-absorbing information layer by sputtering or vapor deposition, are diffuse by diffusion
  • An excessively high vapor pressure of a light-absorbing substance can sublimate the above-mentioned sputtering or vapor deposition of further layers in a high vacuum and thus reduce the desired layer thickness. This in turn leads to a negative influence on the reflectivity.
  • the object of the invention is accordingly to provide suitable compounds which meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the information layer in a write-once optical data carrier, in particular for high-density writable optical media Meet data storage formats in a laser wavelength range from 340 to 680 nm.
  • the invention therefore relates to metal complexes which have at least one ligand of the formula I.
  • R 1 is hydrogen, optionally substituted Ci-C ö alkyl or optionally substituted C 7 -C 12 aralkyl,
  • R 2 represents optionally substituted C] -C 6 -alkyl
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • R 3 represents optionally substituted Ci-Cö-alkyl
  • n and n independently of one another represent 1, 2 or 3,
  • R 51 for optionally substituted Cg-Cio-aryl especially phenyl, an optionally substituted 5- or 6-membered heterocyclic radical, in particular pyridyl, Ci-C ö alkylthio, C -C ⁇ o-Aralk lthio 5 optionally substituted in particular phenylthio, C Ce-alkylsulfonyl, C 7 -C ⁇ o-aralkylsulfonyl or optionally substituted Cg-Cio-arylsulfonyl, in particular phenylsulfonyl,
  • R 52 represents optionally substituted C 1 -C 6 -alkyl, in particular C 1 -C 6 -
  • R 53 and R 54 independently of one another represent optionally substituted Ci-C ⁇ -alkyl, optionally substituted C 7 -C 10 aralkyl or optionally substituted Ce-Cio-aryl or
  • NR 53 R 54 stands for PyrroHdino, Piperidino, Morpholino, Piperazino or N-Ci to C 6 - alkyl-piperidino,
  • R 55 represents hydrogen, methyl or methoxy or
  • R 53 ; R 55 together represent a - (CH 2 ) 2 -, - (CH 2 ) 3 - or - (CH 2 ) 2 -O bridge,
  • R represents optionally substituted Ci-Cg-alkyl, in particular -C 6 - alkyl or perfluoro-Ci-C ö alkyl;
  • R 103 , R 104 , R 1 and R 107 independently of one another represent optionally substituted C 1 -C 6 -alkyl, optionally substituted C 1 -C 10 aralkyl or optionally substituted C 6 -C 6 aryl or
  • NR 103 R 104 and NR 106 R 107 independently of one another for PyrroHdino, Piperidino,
  • R 105 represents hydrogen, methyl or methoxy or R ⁇ ⁇ 3 .
  • the metal complexes are in a preferred embodiment as 1: 1 or 1: 2 metal alkazo complexes.
  • Preferred metal complexes are those which are characterized in that they have the formula (Ia)
  • M stands for a metal
  • M stands for a metal. Also preferred are those metal complexes which are characterized in that they have the formula (Cla)
  • M stands for a metal
  • Preferred metals are divalent metals, transition metals or rare earths, in particular Mg, Ca, Sr, Ba, Cu, Ni, Co, Fe, Zn, Pd, Pt, Ru, Th, Os, Sm.
  • the metals Pb, Fe, Zn, Cu, Ni and Co. are preferred. Ni and Zn are particularly preferred.
  • alkyl or aralkyl radicals Possible substituents of the alkyl or aralkyl radicals are halogen, in particular CI or F, nitro, cyano, CO-NH 2 , alkoxy, trialkylsilyl or trialkylsiloxy.
  • 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
  • Preferred optionally substituted C 1 -C 6 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, n-hexyl, perfluorinated methyl, perfluorinated ethyl, 3,3,3-trifluoromethyl, perfluorobutyl, cyanoethyl, methoxyethyl.
  • Examples of preferred aralkyl include benzyl, phenethyl or phenylpropyl.
  • R 1 represents methyl, ethyl, propyl, butyl, cyanoethyl, methoxyethyl or benzyl,
  • R 2 represents methyl, ethyl, propyl, butyl, difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • X represents O, CH 2 or a direct bond
  • m and n independently of one another represent 1 or 2
  • M stands for Pd, Fe, Zn, Cu, Ni or Co.
  • R 1 represents methyl or ethyl, in particular methyl
  • R 2 represents methyl or trifluoromethyl, in particular trifluoromethyl
  • X represents CH 2 or a direct bond
  • M stands for Zn, Cu, Ni or Co.
  • the metal complexes of the formula I, in particular Ia, which correspond to the formulas TU and JV are regarded as particularly outstanding.
  • metal complexes with ligands of the formula LI in particular metal complexes of the formula LIa, are particularly preferred,
  • R 51 represents phenyl, pyridyl, methylthio, ethylthio, propylthio, benzylthio, methylsulfonyl, benzylsulfonyl or phenylsulfonyl,
  • R 52 represents methyl, ethyl, propyl, butyl, difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifluoroethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • R 53 and R 54 independently of one another represent methyl, ethyl, propyl, butyl, cyanoethyl, chloroethyl, methoxyethyl, benzyl, phenethyl or phenyl or NR 53 R 54 stands for PyrroHdino, Piperidino or Morpholino,
  • R 55 represents hydrogen
  • M represents Pd, Fe, Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • Metal complexes with ligands of the formula (LI) are very particularly preferred, in particular metal complexes of the formula (LIa),
  • R 51 represents phenyl
  • R, 52 represents methyl or trifluoromethyl, preferably trifluoromethyl
  • R and R independently of one another represent methyl, ethyl, cyanoethyl or benzyl or
  • NR 53 R 54 stands for PyrroHdino or Piperidino
  • R 55 represents hydrogen
  • M represents Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • R> 5 J 3 J represents methyl or ethyl
  • R, 54 represents methyl, ethyl or cyanoethyl or
  • NR J R- stands for PyrroHdino or Piperidino.
  • R 106 and R 107 independently of one another represent methyl, ethyl, propyl, butyl, cyanoethyl, chloroethyl, methoxyethyl, benzyl, phenethyl or phenyl or
  • NR 106 R 107 stands for PyrroHdino, Piperidino or Morpholino,
  • R 102 represents methyl, ethyl, propyl, butyl, difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifluoroethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • R 103 and R 104 independently of one another are methyl, ethyl, propyl, butyl, cyanoethyl,
  • NR 103 R 104 stands for PyrroHdino, Piperidino or Morpholino,
  • R 105 represents hydrogen
  • M represents Pd, Fe, Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • Metal complexes with ligands of the formula CI in particular metal complexes of the formula (Cla), are very particularly preferred,
  • NR 106 R 107 represents dimethylamino, diethylamino, dipropyla ino, N-cyanoethyl-N-methylamino, N-cyanoethyl-N-ethylamino, N, N-dicyanethylamino, PyrroHdino or piperidino,
  • R, 102 represents methyl or trifluoromethyl, preferably trifluoromethyl
  • R 103 and R 104 independently of one another represent methyl, ethyl, cyanoethyl or benzyl or
  • NR 103 R 104 stands for PyrroHdino or Piperidino
  • R 105 represents hydrogen
  • M represents Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • R 103 stands for dimethylamino, diisopropylamino or pyrrohdino, R 103 represents methyl or ethyl,
  • R 104 represents methyl, ethyl or cyanoethyl or
  • NR 103 R 104 stands for PyrroHdino or Piperidino.
  • the metal complexes according to the invention are sold in particular as powders or granules or as a solution 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.
  • Granules can be produced, for example, by spray drying.
  • the granules are particularly characterized by their low dust level.
  • the concentrated solutions are also preferred. They are at least 2% by weight, preferably at least 5% by weight, of those according to the invention
  • Metal complexes in particular those of the formulas Ia, III, IV (Cla), (LIa), LEI or CIII.
  • 2,2,3,3-tetafluoropropanol, propanol, butanol, pentanol, diacetone alcohol, dibutyl ether, heptanone or mixtures thereof are preferably used as solvents.
  • 2,2,3,3-Tetrafluoropropanol is particularly preferred.
  • 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 an azo compound of the formula (Ib)
  • R 1 represents hydrogen, optionally substituted C 1 -C 6 -alkyl or optionally substituted C -C 12 -aralkyl
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • R 3 represents optionally substituted Ci-Cg-alkyl
  • n and n independently of one another represent 1, 2 or 3,
  • Two or more different azo compounds of the formula Ib can also be used in this process according to the invention.
  • a statistical mixture of metal complexes is then obtained, consisting of those complexes which contain two identical ligands of the formula I and those complexes which contain two different ligands of the formula I.
  • 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 an azo compound of the formula (Llb)
  • Two or more different azo compounds of the formula (Llb) can also be used in this process according to the invention.
  • a statistical mixture of metal complexes is then obtained, consisting of those complexes which contain two identical ligands of the formula (LI) and those complexes which contain two different ligands of the formula (LI). These mixtures are also the subject of the invention.
  • 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 an azo compound of the formula (Clb)
  • Two or more different azo compounds of the formula Clb can also be used in this process according to the invention.
  • a statistical mixture of metal complexes is then obtained, consisting of those complexes which contain two identical ligands of the formula CI and those complexes which contain two different ligands of the formula CI. These mixtures are also the subject of the invention.
  • the production of metal complexes and the metal complexes themselves are also meant quite analogously if a mixture of azo compounds of the formulas Ib, Llb and / or Clb is used in their production.
  • reaction according to the invention is usually carried out in a solvent or
  • Solvent mixture optionally 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 either precipitate directly and can be isolated by filtration or they are, for example, added by water, possibly with partial or complete preceding
  • Metal salts include, for example, the 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, trifluoro- or methanesulfonate to understand the corresponding metals.
  • Metal salts also include complexes with ligands other than those of
  • formulas (Ia), (LIa) or (Cla), in particular complexes of acetyl acetone and acetyl acetic acid esters are: nickel acetate, cobalt acetate, copper acetate, nickel chloride, nickel sulfate, cobalt chloride, copper chloride, copper sulfate, nickel hydroxide, nickel oxide, nickel acetyl acetonate, cobalt hydroxide, basic copper carbonate, barium chloride, iron sulfate,
  • alkali acetates such as. B. sodium acetate
  • Potassium acetate alkali hydrogen carbonates, carbonates or hydroxides such as sodium hydrogen carbonate, potassium carbonate, lithium mum hydroxide, sodium hydroxide, or amines such as ammonia, dimethylamine, triethylamine, diethanolamine.
  • amines such as ammonia, dimethylamine, triethylamine, diethanolamine.
  • Such basic substances are particularly advantageous when metal salts of strong acids such as 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.
  • the invention therefore also relates to azo compounds of the formula (Ib)
  • R 1 represents hydrogen, optionally substituted C ö alkyl or optionally substituted C 7 -C 12 aralkyl
  • R 2 represents optionally substituted Ci-Ce alkyl
  • X represents O, JH, NR 3 , CH 2 or a direct bond
  • R 3 for optionally substituted C 1 -C 6 -alkyl! stands and m and n independently of one another represent 1, 2 or 3.
  • R 1 represents methyl, ethyl, propyl, butyl, cyanoethyl, methoxyethyl or benzyl,
  • R 2 represents methyl, ethyl, propyl, butyl, difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • X represents O, CH 2 or a direct bond
  • n and n independently of one another represent 1 or 2, in particular
  • R 1 represents methyl or ethyl, in particular methyl
  • R 2 represents methyl or trifluoromethyl, in particular trifluoromethyl
  • X represents CH 2 or a direct bond
  • the invention therefore also relates to azo compounds of the formula (Llb)
  • R 51 -R 55 have the meaning given above.
  • R, 51 represents phenyl, pyridyl, methylthio, ethylthio, propyltliio, benzylthio, methylsulfonyl, benzylsulfonyl or phenylsulfonyl
  • R 52 for methyl, ethyl, propyl, butyl, difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifluoroethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl, preferably difluoromethyl, 3,3-difluoroethyl, 3,3,3- Trifluoroethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • R 53 and R 54 independently of one another represent methyl, ethyl, propyl, butyl, cyanoethyl, chloroethyl, methoxyethyl, benzyl, phenethyl or phenyl or
  • NR 53 R 54 stands for PyrroHdino, Piperidino or Morpholino
  • R 55 represents hydrogen
  • propyl or butyl radicals can also be branched.
  • R 51 represents phenyl
  • R 52 represents methyl or trifluoromethyl, preferably trifluoromethyl
  • R 53 and R 54 independently of one another represent methyl, ethyl, cyanoethyl or benzyl or
  • NR 53 R 54 stands for PyrroHdino or Piperidino
  • R 55 represents hydrogen
  • Azo compounds of the formula (LV) are very particularly preferred.
  • R, 5 M 3 represents methyl or ethyl
  • R, 54 represents methyl, ethyl or cyanoethyl or
  • NR .53r R> 54 stands for PyrroHdino or Piperidino.
  • Azo compounds of the formula (Clb) are known in some cases, e.g. from US-A 5,208,325.
  • the invention therefore also relates to azo compounds of the formula (Clb)
  • R 102 represents perfluoro-Ce-alkyl, R 103 , R 104 , R 106 and R 107 independently of one another for optionally substituted Ci-C ⁇ - alkyl, optionally substituted C 7 -C ⁇ o-aralkyl or optionally substituted C ö -Cio-Ar! stand or
  • NR 103 R 104 and NR 106 R 107 independently of one another for PyrroHdino, Piperidino,
  • R 105 represents hydrogen, methyl or methoxy or
  • R 103 ; R 105 together represent a - (CH 2 ) 2 -, - (CH 2 ) 3 - or - (CH 2 ) 2 -O bridge.
  • R 102 represents difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifmorethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • R 106 and R 107 independently of one another represent methyl, ethyl, propyl, butyl, cyanoethyl, chloroethyl, methoxyethyl, benzyl, phenethyl or phenyl or
  • NR 106 R 107 stands for PyrroHdino, Piperidino or Morpholino,
  • R 103 and R 104 independently of one another represent methyl, ethyl, propyl, butyl, cyanoethyl, chloroethyl, methoxyethyl, benzyl, phenethyl or phenyl or
  • NR 103 R 104 stands for PyrroHdino, Piperidino or Morpholino,
  • R 105 represents hydrogen
  • Azo compounds of the formula (Clb) are particularly preferred, worm
  • NR 106 R 107 for dimethylamino, diethylamino, dipropylamino, N-cyanoethyl-N-methylamino, N-cyanoethyl-N-ethylamino, N, N-dicyanethylamino, Pyrro ⁇
  • R 103 and R 104 independently of one another represent methyl, ethyl, cyanoethyl or benzyl or
  • R 105 represents hydrogen
  • propyl or butyl radicals can also be branched.
  • NR, 106 ⁇ R> 107 represents dimethylamino, diisopropylamino or PyrroHdino, R 103 represents methyl or ethyl,
  • R 104 represents methyl, ethyl or cyanoethyl or
  • NR 103 R 104 stands for PyrroHdino or Piperidino.
  • the invention also relates to a process for preparing the azo compounds of the formula (Tb) according to the invention, which is characterized in that an aminoimidazole of the formula (VH)
  • R 1 for hydrogen, optionally substituted or optionally substituted stands,
  • R 2 represents optionally substituted C 6 -C 6 alkyl
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • R 3 represents optionally substituted C 1 -C 6 -alkyl
  • n each independently represent 1, 2 or 3
  • Another object of the invention is a process for the preparation of the azo compounds of the formula Ib according to the invention, characterized in that an aminoimidazole of the formula (IX)
  • R 2 represents optionally substituted C 1 -C 6 -alkyl
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • R 3 represents optionally substituted Ci-Cg-alkyl
  • nj each independently represent 1, 2 or 3, couples,
  • R 1 represents hydrogen, optionally substituted C r C6 alkyl or optionally substituted C7-C12 aralkyl and
  • Y represents a leaving group
  • R -Y stands for example for an alkyl or aralkyl chloride, bromide, iodide, methanesulfonate, trifluoromethanesulfonate, benzenesulfonate, tolulsulfonate or a sulfuric acid alkyl or aralkyl ester.
  • Examples are methyl iodide, benzyl bromide, dimethyl sulfate, toluenesulfonic acid ethyl ester.
  • the basic substances listed above are suitable as basic substances.
  • Another object of the invention is a process for the preparation of the azo compounds of the formula Llb according to the invention, characterized in that a 5-amino-l, 2,4-thiadiazole of the formula (LVII)
  • R 51 represents optionally substituted Cg-Cio-aryl, especially phenyl, an optionally substituted 5- or 6-membered heterocyclic radical, in particular pyridyl optionally substituted - C ö alkylthio, optionally substituted C 7 -C 1 o-aralkylthio or optionally substituted Cö-Cio-arylthio or phenylthio,
  • R .52 represents optionally substituted C 1 -C 6 -alkyl
  • R 53 and R 54 independently of one another represent optionally substituted CrC 6 -alkyl, optionally substituted CrC.o-aralkyl or optionally substituted Cg-do-aryl or
  • NR 53 R 54 stands for PyrroHdino, Piperidino, Morpholino, Piperazino or N-C ⁇ -C 6 alkyl piperidino, R 55 represents hydrogen, methyl or methoxy or
  • R 53 ; R 55 together represent a - (CH 2 ) 2 -, - (CH 2 ) 3 - or - (CH 2 ) 2 -O bridge,
  • Another object of the invention is a process for the preparation of the azo compounds of the formula Clb according to the invention, characterized in that a 2-amino-1, 3, 4-thiadiazole of the formula (CVII)
  • R 106 and R 107 independently of one another represent optionally substituted dC 6 -alkyl, optionally substituted C -C -oalkyl or optionally substituted C 6 -CiQ-aryl or
  • NR 106 R 107 stands for PyrroHdino, Piperidino, Morpholino, Piperazino or N-C ⁇ -C 6 alkyl piperidino,
  • R, 102 represents optionally substituted C 1 -C 6 -alkyl
  • R 103 and R 104 independently of one another represent optionally substituted CrC 6 alkyl, optionally substituted C 7 -Cio aralkyl or optionally substituted C o -Cio aryl or
  • NR 103 R 104 stands for PyrroHdino, Piperidino, Morpholino, Piperazino or N-Ci-C ⁇ -alkylpiperidino,
  • R 105 represents hydrogen, methyl or methoxy or
  • R, 1 1 0 W 3 ;. ⁇ R. 1 ⁇ 0 ⁇ 5 D together represent a - (CH 2 ) 2 -, - (CH 2 ) 3 - or - (CH 2 ) 2 -O bridge,
  • the 5-amino-1,2,4-thiadiazoles of the formulas LVII to be used in the inventive methods are, for. B. from Chem. Ber. 1954, 87, 68; Chem. Ber. 1956, 89, 1956, 2742; DE-OS 2 811 258 known or can be prepared in an analogous manner.
  • the invention further relates to the coupling component of the formula (VIII)
  • R 2 represents optionally substituted Ci-C ⁇ -alkyl
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • R 3 for optionally substituted Ci-Cg-alky! stands and
  • n and m each independently represent 1, 2 or 3.
  • the invention also relates to a process for the preparation of coupling components of the formula VIII, which is characterized in that
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • Y stands for a leaving group
  • n and m each independently represent 1, 2 or 3
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • n and m each independently represent 1, 2 or 3
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • n and m each independently represent 1, 2 or 3
  • R 2 represents optionally substituted Ci-Cg-alkyl
  • the coupling component of the formula (VHI) is thus obtained in free form, as an HC1 salt or as an R 2 SO 2 OH salt.
  • Alkylation agents of the formula (XI) are, for example, 1,4-dibromobutane, 1,5-di-bromopentane, 2,2'-dichlorodiethyl ether, 1,4-bis (benzenesulfonyloxy) butane.
  • Compounds of the formula (XII) are known, for example, from Chem. Pharm. Bull., 1998, 46, 951. But you can also analog Bull. Chem. Soc. Jpn., 1991, 64, AI.
  • 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.
  • the optical data carrier is preferably written and read with blue laser light, in particular with a wavelength in the range of 360-460 nm.
  • the optical data carrier is also preferably written to and read with red laser light, in particular with a wavelength in the range from 600-700 nm.
  • the invention further relates to the use of metal complexes with azohands as a light-absorbing compound in the information layer of write-once optical data carriers, the optical data carrier being able to be written and read with blue laser light, in particular with a wavelength in the range of 360-460 nm.
  • the invention further relates to an optical data carrier, comprising a preferably transparent substrate, optionally already coated with one or more reflective layers, on the surface of which an information layer which can be written on with light, optionally one or more reflection layers and optionally a protective layer or a further substrate or a cover - Layer applied are those with blue, 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, or red light, preferably with a wavelength in the range of 600-700 nm , preferably from 620 to 680 nm, very particularly preferably from 630 to 660 nm, preferably laser light, can be written and read, the information layer containing a light-absorbing compound and optionally a binder, characterized in that at least one metal complex according to the invention is used as the light-absorbing compound becomes.
  • the light-absorbing compound should preferably be thermally changeable.
  • the thermal change preferably takes place at a temperature ⁇ 600 ° C., particularly preferably at a temperature ⁇ 400 ° C., very particularly preferably at a temperature ⁇ 300 ° C., in particular ⁇ 200 ° C.
  • Such a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
  • the preferred embodiment of the light-absorbing compounds in the optical data memory according to the invention correspond to the preferred embodiment of the metal complex according to the invention.
  • the light-absorbing compounds used are those of the formula (Ia)
  • R 1 represents methyl, ethyl, propyl, butyl, cyanoethyl, methoxyethyl or benzyl,
  • R 2 represents methyl, ethyl, propyl, butyl, difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • X represents O, CH 2 or a direct bond
  • n and n independently of one another represent 1 or 2 and
  • M stands for Pd, Fe, Zn, Cu, Ni or Co.
  • the light-absorbing compound used is that of the formula (Ia)
  • R 1 represents methyl or ethyl, preferably methyl
  • R ⁇ 2 represents methyl or trifluoromethyl, preferably trifluoromethyl
  • X represents CH 2 or a direct bond
  • M stands for Zn, Cu, Ni or Co.
  • the light-absorbable compounds used are those of the formula III or TV
  • the light-absorbing compounds used are those of the formula (LIa),
  • R 51 for optionally substituted C -Ci Q -Ar l in particular phenyl, an optionally substituted 5- or 6-membered heterocyclic radical, in particular pyridyl, optionally substituted Ci-C ö alkylthio, optionally substituted C 7 -Cio aralkylthio, optionally substituted Cg-Cio-arylthio, in particular phenylthio, Ci-C 6 -alkyl sulfonyl, C -C 10 aralkylsulfonyl or optionally substituted especially phenylsulfonyl,
  • R represents optionally substituted C j -CG-alkyl, in particular C ⁇ -C 6 - alkyl, or perfluoro-C r C 6 - alkyl,
  • R 53 and R 54 independently of one another represent optionally substituted Ci-C 6 alkyl, optionally substituted C 7 -Cio aralkyl or optionally substituted C 6 -C ⁇ o aryl or
  • NR 53 R 54 stands for PyrroHdino, Piperidino, Morpholino, Piperazino or N-Ci to C 6 - alkyl-piperidino, R 55 represents hydrogen, methyl or methoxy or
  • R 53 ; R 55 together represent a - (CH) 2 -, - (CH 2 ) 3 - or - (CH 2 ) 2 -O bridge, and
  • M is a metal
  • the light-absorbing compounds used are those of the formula (LIa)
  • R 51 represents phenyl
  • R 52 represents methyl or trifluoromethyl, preferably trifluoromethyl
  • R 53 and R 54 independently of one another represent methyl, ethyl, cyanoethyl or benzyl or
  • NR 53 R 54 stands for PyrroHdino or Piperidino
  • R 55 represents hydrogen
  • M represents Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • the light-absorbing compounds used are those of the formula (LIa)
  • R 5 J 1 i represents phenyl
  • R> 52 represents methyl or trifluoromethyl, preferably trifluoromethyl
  • R 53 and R 54 independently of one another represent methyl, ethyl, cyanoethyl or benzyl or
  • NR, 53r R, 54 stands for PyrroHdino or Piperidino
  • R 55 represents hydrogen
  • M represents Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • the light-absorbing compounds used are those of the formula (LIII)
  • R, 53 represents methyl or ethyl
  • R 54 represents methyl, ethyl or cyanoethyl or NR 53 R 54 stands for PyrroHdino or Piperidino.
  • the light-absorbing compounds used are those of the formula (Cla)
  • R 102 6 alkyl is optionally substituted C ⁇ -C, in particular C I -C ⁇ - alkyl or perfluoro-Ci-C 6 alkyl,
  • R 103, R 104, R 106 and R 107 independently represent optionally substituted C ⁇ -C 6 -A-lkyl, optionally substituted C 7 -C each other 0 - aralkyl or optionally substituted C 6 -C 10 aryl, or
  • NR 103 R 104 and NR 106 R 107 independently of one another represent PyrroHdino, Piperidino, Morpholino, Piperazino or N-Ci - to C 6 -alkyl-piperidino,
  • R 105 represents hydrogen, methyl or methoxy or
  • R i05 together represent a - (CH 2 ) 2 -, - (CH 2 ) 3 - or - (CH 2 ) 2 -O bridge, and
  • M stands for a metal
  • the light-absorbing compounds used are those of the formula (Cla)
  • R 106 and R 107 independently of one another are methyl, ethyl, propyl, butyl, cyanoethyl,
  • Chloroethyl, methoxyethyl, benzyl, phenethyl or phenyl or NR 106 R 107 stands for PyrroHdino, Piperidino or Morpholino,
  • R 102 represents methyl, ethyl, propyl, butyl, difluoromethyl, 3,3-difluoroethyl, 3,3,3-trifluoroethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or perfluorobutyl,
  • R 103 and R 104 independently of one another represent methyl, ethyl, propyl, butyl, cyanoethyl, chloroethyl, methoxyethyl, benzyl, phenethyl or phenyl or
  • NR 103 R 104 stands for PyrroHdino, Piperidino or Morpholino,
  • R 105 represents hydrogen
  • M represents Pd, Fe, Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • the light-absorbing compounds used are those of the formula (CIa), in which
  • NR 106 R 107 represents dimethylamino, diethylamino, dipropylamino, N-cyanoethyl-N-methylamino, N-cyanoethyl-N-ethylamino, N, N-dicyanethylamino, PyrroHdino or piperidino,
  • R represents methyl or trifluoromethyl, preferably trifluoromethyl
  • R 103 and R 104 independently of one another represent methyl, ethyl, cyanoethyl or benzyl or
  • R 105 represents hydrogen and
  • M represents Zn, Cu, Ni or Co
  • propyl or butyl radicals can also be branched.
  • the light-absorbing compounds used are those of the formula (CiJX)
  • NR, 106- Rr> 107 represents dimethylamino, diisopropylamino or pyrro-hdino,
  • R, 1 ⁇ 0 ⁇ 3 j represents methyl or ethyl
  • R, 1 ⁇ 0 w 4 represents methyl, ethyl or cyanoethyl or
  • NR R stands for PyrroHdino or Piperidino.
  • those light-absorbing compounds are preferred whose absorption maximum ⁇ max2 is in the range 420 to 550 nm, the wavelength ⁇ / 2 at which the absorbance in the short wavy flank of the absorption maximum of the wavelength ⁇ ma ⁇ 2 is half the extinction value at ⁇ max2 , and the wavelength ⁇ / ⁇ o at which the extinction in the short-wave flank of the absorption maximum of the wavelength ⁇ m a ⁇ 2 eu ⁇ is tenths of the extinction value at ⁇ rnaX2 are not more than 80 nm apart.
  • Such a light-absorbing compound preferably has no shorter-wave maximum ⁇ max up to a wavelength of 350 nm, particularly preferably up to 320 nm, very particularly preferably up to 290 nm. on.
  • Light- absorbing compounds with an absorption maximum ⁇ maX2 of 430 to 550 nm, in particular 440 to 530 nm, are particularly preferred
  • the light-absorbing compounds are preferably ⁇ / 2 and ⁇ . / io, as defined above, not more than 70 nm, particularly preferably not more than 50 nm, very particularly preferably not more than 40 nm apart.
  • a light-absorbing compound whose absorption maximum ⁇ m a consult2 is in the range from 500 to 650 nm, the wavelength ⁇ / 2 at which the extinction in the long-wave flank of the absorption maximum of the wavelength ⁇ maX2 is half the extinction value at ⁇ max2 , and the wavelength ⁇ / ⁇ 0 , at which the extinction in the long-wave flank of the absorption maximum of the wavelength ⁇ m -j ü is one-tenth of the extinction value at ⁇ rnaX2 , preferably not more than 60 nm apart.
  • Such a light-absorbing compound preferably has no longer-wavelength maximum ⁇ max3 up to a wavelength of 750 nm, particularly preferably 800 nm, very particularly preferably 850 nm.
  • Light- absorbing compounds with an absorption maximum ⁇ maX2 of 510 to 620 nm are preferred.
  • Light- absorbing compounds with an absorption maximum ⁇ max2 of 530 to 610 nm are particularly preferred.
  • Light- absorbing compounds with an absorption maximum ⁇ max2 of 550 to 600 nm are very particularly preferred.
  • These light-absorbing compounds ⁇ and ⁇ mo, as defined above, are preferably not more than 50 nm apart, more preferably not more than 40 nm apart, very particularly preferably not more than 30 nm apart.
  • the light-absorbing compounds show at the absorption maximum / u -. preferably 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 light-absorbing compounds with the required spectral properties are, in particular, those which have low solvatochromism (dioxane / DMF or methylene chloride / methanol).
  • Metal complexes are preferred whose solvatochromism ⁇ oD - - ⁇ Dio ⁇ an
  • the once writable optical data carrier according to the invention is preferred and is written and read with the light of a red or blue, in particular red, laser.
  • a red or blue, in particular red, laser is preferred.
  • Other metal complexes are known for example, e.g. B. from US-Bl 6,225,023.
  • the light-absorbing compounds used according to the invention guarantee a sufficiently high reflectivity (> 10%) of the optical data carrier in the blank state and a sufficiently high absorption for thermal
  • Degradation of the information layer with purical lighting with focused light if the light wavelength is in the range of 360 to 460 nm and 600 to 680 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 which have changed after thermal degradation.
  • the metal complexes according to the invention are preferably applied to the optical data carrier by spm-coating or vacuum evaporation, in particular spin-coating. They 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 optical data storage device can carry further layers such as metal layers, dielectric layers and protective layers.
  • Metals and dielectric layers serve u. a. to adjust the reflectivity and the heat balance. Depending on the laser wavelength, metals can be gold, silver, aluminum and the like. a. his.
  • Dielectric layers are, for example, silicon dioxide and silicon nitride.
  • Protective layers are, for example, photocurable lacquers, (pressure-sensitive) adhesive layers and protective films.
  • 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.
  • the optical data carrier according to the invention has, for example, the following layer structure (cf. FIG. 1): a transparent substrate (1), optionally a protective layer (2), an information layer (3), optionally a protective layer (4), optionally an adhesive layer (5) , a cover layer (6).
  • a transparent substrate (1) optionally a protective layer (2)
  • an information layer (3) optionally a protective layer (4)
  • optionally an adhesive layer (5) optionally an adhesive layer (5)
  • cover layer (6) optionally an adhesive layer (5)
  • cover layer (6) for example, the following layer structure (cf. FIG. 1): a transparent substrate (1), optionally a protective layer (2), an information layer (3), optionally a protective layer (4), optionally an adhesive layer (5) , a cover layer (6).
  • the structure of the optical data carrier can preferably:
  • a 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 (4), optionally an adhesive layer (5), and a transparent one Cover layer (6) are applied.
  • a transparent substrate (1) on the surface of which a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • a preferably transparent substrate (1) on the surface of which there is optionally a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a trans Parente cover layer (6) are applied.
  • the optical data carrier has, for example, the following layer structure (cf. FIG. 2): a preferably transparent substrate (11), an information layer (12), optionally a reflection layer (13), optionally an adhesive layer (14), another preferably transparent substrate (15).
  • the invention further relates to optical data carriers according to the invention described with blue or red light, in particular laser light, in particular red laser light.
  • the coupling component from b) was produced as follows:
  • Suitable metal complexes are also compiled in the following examples and in Table 1. These are obtained by analogous production of the coupling components, azo dyes or metal complexes.
  • Suitable metal complexes are also summarized in the following examples and in Table 2. These are obtained by analogous production of the coupling components, azo dyes or metal complexes.
  • Suitable metal complexes are also summarized in the following examples and in Table 3. These are obtained by analogous production of the coupling components, azo dyes or metal complexes.
  • Example 52
  • a 3% by weight solution of the metal complex from Example 29 in 2,2,3,3-tetrafluoropropanol was prepared at room temperature. This solution was created using
  • the pregrooved polycarbonate substrate was produced as a disk using injection molding.
  • the dimensions of the disc and the groove structure corresponded to those which are usually used for DVD-R.
  • the disk with the dye layer as the information carrier was sputtered with 100 nm silver.
  • a UV-curable acrylic lacquer was then applied by spin coating and cured using a UV lamp.
  • Ratio C / N 49 dB measured.
  • the write power was applied as an oscillating pulse sequence (see Figure 1), whereby the disk was alternately irradiated with the above-mentioned write power P wr u e and the read power P reac t «0.5 mW.
  • the 11T long writing pulse was followed by an 11T long break. The disc was irradiated with this oscillating pulse sequence until it had turned around once. After that, the marking created in this way with the Read power P read and the above-mentioned signal-to-noise ratio C / N measured.
  • R is hydrogen, optionally substituted Ci-C ö alkyl or optionally substituted C 7 -C 12 aralkyl,
  • X represents O, NH, NR 3 , CH 2 or a direct bond
  • R 3 represents optionally substituted CI-C ⁇ - alkyl
  • n and n independently of one another represent 1, 2 or 3,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

L'invention concerne de nouveaux complexes métalliques pour support de données optique. Un tel support de données est constitué d'un substrat, de préférence transparent, éventuellement déjà recouvert d'au moins une couche réflectrice, qui comporte sur sa surface une couche d'information sur laquelle les informations peuvent être écrites à l'aide d'une lumière, éventuellement au moins une couche réflectrice et éventuellement une couche protectrice ou bien un autre substrat ou une autre couche de recouvrement sur lequel ou sur laquelle des informations peuvent être écrites et lues à l'aide d'une lumière bleue ou rouge, de préférence une lumière laser. La couche d'information contient un composé photoabsorbant et éventuellement un liant, et elle se caractérise en ce que l'on utilise, comme composé photoabsorbant, au moins un des complexes métalliques susmentionnés.
EP03766171A 2002-07-26 2003-07-15 Complexes metalliques utilises comme composes photoabsorbants dans la couche d'information de supports de donnees optiques Withdrawn EP1556445A2 (fr)

Applications Claiming Priority (3)

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DE10234288 2002-07-26
DE10234288A DE10234288A1 (de) 2002-07-26 2002-07-26 Metallkomplexe als lichtabsorbierende Verbindungen in der Informationsschicht von optischen Datenträgern
PCT/EP2003/007641 WO2004013234A2 (fr) 2002-07-26 2003-07-15 Complexes metalliques utilises comme composes photoabsorbants dans la couche d'information de supports de donnees optiques

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EP1556445A2 true EP1556445A2 (fr) 2005-07-27

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EP (1) EP1556445A2 (fr)
JP (1) JP2005533912A (fr)
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DE (1) DE10234288A1 (fr)
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JP4327668B2 (ja) * 2004-06-25 2009-09-09 太陽誘電株式会社 光情報記録媒体
US8173335B2 (en) 2006-07-14 2012-05-08 The Trustees Of The University Of Pennsylvania Beam ablation lithography

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CH576509A5 (en) * 1972-02-23 1976-06-15 Ciba Geigy Ag Monoazo dispersion dyes - from 3-alkyl-, aryl-or dialkylamino-sulphonylamino aniline derivs as coupling components
JP2604166B2 (ja) * 1987-07-31 1997-04-30 日清製油株式会社 潤滑油
DE19524134A1 (de) * 1995-07-03 1997-01-09 Bayer Ag Verfahren zum Reduzieren der Toxizität von Restflotten und neue kationische Farbstoffe
JP3680428B2 (ja) * 1996-07-17 2005-08-10 三菱化学株式会社 金属キレート化合物および該金属キレート化合物を用いた光学記録媒体
EP0844243B1 (fr) * 1996-11-20 2004-08-25 Mitsubishi Chemical Corporation Dérivés sulfonamide et procédé de préparation, chelates métalliques préparés des dérivés sulfonamide et support d'enregistrement optique préparé a partir de ces chelates métalliques

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US20060141395A1 (en) 2006-06-29
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AU2003246699A1 (en) 2004-02-23
WO2004013234A3 (fr) 2004-05-27
TW200413475A (en) 2004-08-01
DE10234288A1 (de) 2004-02-05
CN1685014A (zh) 2005-10-19

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