WO2006007983A1 - Melanges de complexes metalliques azoiques utilises comme composes absorbant la lumiere dans la couche de donnees de supports de donnees otiques - Google Patents

Melanges de complexes metalliques azoiques utilises comme composes absorbant la lumiere dans la couche de donnees de supports de donnees otiques Download PDF

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Publication number
WO2006007983A1
WO2006007983A1 PCT/EP2005/007352 EP2005007352W WO2006007983A1 WO 2006007983 A1 WO2006007983 A1 WO 2006007983A1 EP 2005007352 W EP2005007352 W EP 2005007352W WO 2006007983 A1 WO2006007983 A1 WO 2006007983A1
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formula
methyl
light
hydrogen
optical data
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PCT/EP2005/007352
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German (de)
English (en)
Inventor
Horst Berneth
Karin HASSENRÜCK
Timo Meyer-Friedrichsen
Josef-Walter Stawitz
Ulrich Feldhues
Friedrich-Karl Bruder
Rafael Oser
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Lanxess Deutschland Gmbh
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Publication of WO2006007983A1 publication Critical patent/WO2006007983A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/2467—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
    • G11B7/246—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
    • G11B2007/24612—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 two or more dyes in one layer
    • 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
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
    • G11B7/2472—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes cyanine
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
    • G11B7/2475—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes merocyanine
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
    • G11B7/2478—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes oxonol
    • 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
    • G11B7/2495—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 anions

Definitions

  • the invention relates to mixtures of azo metal complexes, specific azo metal complexes, a process for their preparation, the azo compounds which function as ligands of the metal complexes and their preparation, which are based on the azo compounds
  • the write-once optical data carriers using special light-absorbing substances or mixtures thereof are particularly suitable for use in high-density recordable optical data storage devices which operate with blue laser diodes, in particular GaN or SHG laser diodes (360-460 nm) and / or for the For use with DVD-R or CD-R discs that use red (635 - 660 nm) or infrared (780 - 830 nm) laser diodes
  • the recordable compact disc (CD-R, 780 nm) has recently undergone enormous volume growth and represents the technically established system.
  • the writable information layer of light-absorbing organic substances must have as amorphous a morphology as possible in order to keep the noise signal as small as possible during writing or reading.
  • the amorphous layer of light-absorbing substances should preferably have a high heat resistance, otherwise other layers of organic or inorganic material, which are applied by sputtering or vapor deposition on the light-absorbing information layer via diffusion form blurred boundary surfaces and thus affect the reflectivity unfavorable.
  • a light-absorbing substance with too low heat resistance at the interface to a polymer carrier can diffuse in these and in turn affect the reflectivity unfavorable.
  • Too high a vapor pressure of a light-absorbing substance can sublime in 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.
  • JP 11-310 728 describes an optical recording medium containing certain nonionic azo metal complexes in its information layer. These azo metal complexes contain azo dyes that must contain at least 2 fluorine atoms.
  • Azo dyes further contain a grouping of the formula -NH-SO 2 -Y, wherein Y is an alkyl or aryl radical.
  • the optical data memory is suitable for a write and read laser wavelength of 630-660 nm.
  • the object of the invention is therefore 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 recordable optical data storage formats in a Laserwellen ⁇ length range from 340 to 680 nm meet.
  • mixtures of azo metal complexes can fulfill the abovementioned requirement profile particularly well.
  • the invention therefore relates to mixtures containing at least two different
  • ⁇ i is S or NH
  • X 1 and X 1 independently of one another are CH or N,
  • heterocycle containing X 1 can be substituted by nonionic radicals
  • R 0 is NR 2 R 2 ' , R 8 or K + An
  • R 2 and R 2 ' are independently of each other optionally substituted by hydroxy, cyano or fluorine-substituted Ci-C ⁇ - alkyl and
  • R 2 can additionally be hydrogen
  • R 3 and R 4 are independently of each other optionally substituted by hydroxy, cyano, chlorine, acetoxy or -COOR 7 substituted Ci-C 4 alkyl or
  • NR 3 R 4 represents optionally substituted pyrrolidino, piperidino, morpholino,
  • R, R and R? 4; .uR6 independently of one another are together a - (CH 2 ⁇ - or - (CH 2 ) 3 bridge,
  • R 8 is optionally substituted by chlorine, C 1 -C 4 -alkoxy, in particular methoxy,
  • K + is an optionally substituted by chlorine, C ⁇ -C ⁇ alkoxy, in particular
  • R 11 is C 1 -C 4 -alkyl, in particular methyl, ethyl or benzyl, and
  • R 7 is Ci-C4-alkyl, in particular methyl or ethyl.
  • mixtures according to the invention comprising at least one azo metal complex which carries at least one ligand of the formula (I) in which
  • ⁇ l is NH and at least one different azometallic complex, which carries at least one ligand of the formula (T), wherein ⁇ l is S and the remaining radicals have the above meanings.
  • mixtures comprising at least one azo metal complex which comprises at least one ligand of the formula (IIa)
  • the X ⁇ -containing heterocycle of the formula (IHb) is unsubstituted or substituted by chlorine, bromine, nitro, cyano, methyl, ethyl, phenyl, -SR 7 or -SO 2 R 7 .
  • mixtures comprising at least one azo metal complex which has at least one ligand of the formula (XI), (XII) and / or (XHI)
  • R 0 is NR 2 R 2 , R 8 or a radical of the formula
  • R 1 is methyl or benzyl
  • R 2 and R 2 ' are independently methyl, ethyl or 2,2,2-trifluoroethyl and
  • R 2 can additionally be hydrogen
  • R 3 and R 4 are independently methyl, ethyl or
  • NR 3 R 4 represents pyrrolidino, piperidino, morpholino, piperazino or N-methylpiperazino,
  • R 5 and R 6 are hydrogen or
  • R 3 , R 5 and R 4 , R 6 independently of one another are together a - (CK 2 ) I or - (CH 2 V bridge,
  • R 7 is methyl or ethyl
  • R 8 is 2-thienyl, pyridine-N-oxide-3-yl, 2-, 3- or 4-pyridyl,
  • R 9 is hydrogen, methyl, trifluoromethyl, chlorine or bromine
  • R ! 10 is trifluoromethyl
  • R 11 is methyl, ethyl or benzyl
  • R 12 is hydrogen, cyano or nitro
  • the azo metal complexes are present as 1: 1 or 1: 2 metal: azo complexes, more preferably as 1: 2 metal: azo complexes.
  • Azometallkomplexe containing two identical or different, in particular two identical ligands of the formula (I). If it concerns two different ligands, then also the statistical mixtures of the complexes obtainable from ligands and metal are meant.
  • M stands for a metal
  • Divalent transition metals in particular Cu, Ni, Co, Zn, Pd, are suitable as preferred metals for the azo metal complexes.
  • the metals Cu, Ni and Co. are preferred.
  • Ni is particularly preferred.
  • metals for the Azometallkomplexe come trivalent transition metals, in particular Co, Cr in question. Preferred is Co.
  • R 0 is NR 2 R 2 ' , R 8 or a radical of the formula
  • R 1 is methyl
  • R 2 is methyl or 2,2,2-trifluoroethyl
  • R r is hydrogen or methyl
  • R 3 and R 4 are ethyl and R 5 and R 6 are hydrogen or
  • R 3 , R 5 is a -CH 2 -CH 2 -bridge and R 4 is methyl or ethyl and R 6 is hydrogen or
  • R 6 represents a -CH 2 -CH 2 -CH 2 -bridge
  • R 8 is 2-thienyl, 2- or 3-pyridyl
  • R 9 is hydrogen, methyl or bromine
  • R 1 is methyl
  • R 2 and R 2 ' are methyl
  • R 3 and R 4 are ethyl and R 5 and R 6 are hydrogen or
  • R 3 ; R 5 and R 4 ; R 6 represents a -CH 2 -CH r CH 2 bridge and
  • R 9 is methyl or bromine.
  • R 0 is 3-pyridyl
  • R 1 is methyl
  • R 2 and R 2 ' are methyl
  • R 3 and R 4 are ethyl and R 5 and R 6 are hydrogen or
  • R 3 ; R 5 and R 4 ; R 6 represents a -CH 2 -CH 2 -CH 2 -bridge and
  • R 9 is methyl or bromine.
  • R 0 is a radical of the formula
  • R 1 is methyl
  • R 2 and R 2 ' are methyl
  • R 3 and R 4 are ethyl and R 5 and R 6 are hydrogen or
  • R 6 represents a -CH 2 -CH 2 -CH 2 -bridge
  • R 9 is methyl or bromine
  • Preferred mixtures of azo metal complexes are those which contain nickel complexes of the formula (Ia) with the following ligands:
  • R 0 is one of the following formulas:
  • nickel complexes of the formula (Ia) which have two identical leaflets of the formula (I), which both correspond to the same of the abovementioned formulas (XIa) to (XVIh) and which also carry the same radical R 0 .
  • nickel complexes of the formula (Ia) which have two different ligands of the formula (I) 5 but which both correspond to the same ones of the abovementioned formulas (XIa) to (XVIh), where R 0 for one of the ligands
  • T stands and for the other ligand R 0 for
  • the latter are usually mixtures of metal complexes with
  • Suitable anions An "are all monovalent anions or one equivalent of a polyvalent anion or an equivalent of an oligomeric or polymeric anion in question. Preferably, there is are colorless anions. Suitable anions are for example chloride,
  • Toluoyl substituted benzoate the anion of naphthalene or benzenedicarboxylic acid, Diphenyletherdisulfonat, mono-, di- or trinitrophenolate, tetraphenylborate, cyanotriphenylborate, tetra-Cr to C 2 o-alkoxyborate, tetraphenoxyborate, 7,8- or 7,9-dicarba-nido -undecaborate (l-) or (2-) which are optionally substituted on the B and / or C atoms by one or two C 1 to C 10 alkyl or phenyl groups,
  • An "all monovalent anions or one equivalent of a polyvalent anion of a dye can be used.
  • the anionic dye to an absorption spectrum similar to the cationic azo metal salt.
  • Suitable examples are anionic azo dyes, anthraquinone dyes, methine dyes, porphyrins, phthalocyanines, subphthalocyanines, cyanines, merocyanines, rhodamines, metal complexes and oxonols.
  • Suitable rhodamines as anions are " For example, from DE-A 101 36 064 known.
  • Suitable cyanines as anions are known, for example, from US 2002/0022104.
  • Suitable metal complexes as anions are known, for example, from WO 03/098618.
  • Suitable oxonols as anions are known, for example, from EP-A 1 253 148.
  • Suitable rhodamine dyes are, for.
  • those of the formula (C) are, for.
  • R and R independently of one another represent hydrogen, methyl or ethyl
  • R 102 and R 104 independently of one another represent a sulfo or carboxy-substituted phenyl, naphthyl, benzthiazolyl or benzoxazolyl radical which may be substituted by chlorine, hydroxyl, methyl, methoxy or methylthio,
  • R 105 , R 106 , R 108 and R 109 are independently hydrogen, methyl or methoxy or R 101 ;
  • R 109 independently of one another are - (CH 2 ) 2 -, - (CH 2 ) 3 -, -C (CH 2 ) 2 -CH 2 -CH (CH 3 ) - or -O (CH 2 ) 2 - and
  • R 107 is hydrogen or sulfo.
  • Suitable oxonol dyes are, for. B. those of the formula (CI)
  • the rings B and C represent a five- or six-membered, carbocyclic or heterocyclic ring.
  • the ring B together with the two carbon atoms and the
  • R 111 and R 112 independently of one another represent hydrogen or methyl
  • R 113 is methyl or trifluoromethyl
  • R 114 is cyano, methoxycarbonyl or ethoxycarbonyl
  • R 115 is phenyl, chlorophenyl or tolyl
  • R 116 and R 117 independently represent hydrogen, methyl, ethyl, propyl or together represent a - (CH 2 ) ⁇ 5 - (CH 2 ) S-, - (CH 2 ) 6 bridge.
  • Suitable metal complex dyes are, for. Eg those of the formula (CII)
  • Y and Y are independently -O- or -COO-
  • M • 101 represents a divalent or trivalent metal
  • the rings H stand for a benzene ring or for a five- or six-membered, carbocyclic or heterocyclic ring which can be benzanellated and / or substituted by nonionic radicals, COOH or SO 3 H.
  • the rings H together with the two carbon atoms and Y 102 are a radical of the formulas
  • R and R independently of one another represent hydrogen or methyl
  • R ] 113 is methyl or trifluoromethyl
  • R 115 is phenyl, chlorophenyl or tolyl.
  • M is preferably Ni, Co, Cr, Fe, Cu.
  • Suitable cyanine dyes are, for. B. those of the formula (CHI)
  • R 131 and R 132 are independently of one another - (CH 2 VCOO “ , - (CH 2 ) n -SO 3 " or - (CH 2 ) n -O-SO 3 " ,
  • R 133 and R 134 independently of one another represent hydrogen, a nonionic radical, -COO " or -SO 3 " ,
  • the benzene rings D and E can be independently benzannelated and
  • n is an integer from 2 to 5.
  • Suitable merocyanine dyes are, for.
  • those of the formula (CIV) are, for.
  • R 135 is methyl, ethyl, benzyl, - ⁇ CH 2 ) n -COO " , - (CH 2 VSO 3 ' or - (CH 2 VO-SO 3 -,
  • R 136 is hydrogen, a nonionic radical, -COO ' or -SO 3 -,
  • the benzene ring F can be benzanelated
  • R 121 and R 122 independently of one another represent hydrogen, methyl or - (CH 2 VCOO-, - (CH 2 VSO 3 ' or - (CH 2 VO-SO 3 - stand,
  • R 123 is methyl or trifluoromethyl
  • R 124 is cyano, methoxycarbonyl or ethoxycarbonyl
  • R 125 is phenyl, chlorophenyl or tolyl
  • R 129 and R 130 independently of one another represent hydrogen, methyl, ethyl, propyl or together represent a - (CH 2 V, - (CH 2 ) S -, - (CH 2 VBrücke stand and
  • n is an integer from 2 to 5, wherein at least one of R 135 , R 121 and R 122 is - (CH 2 VCOO " , - (CH 2 ) H -SO 3 - or - (CH 2 ) H -O-SO 3 " , preferably Kr- (CH 2 VSO 3 " stands.
  • merocyanine dyes are, for. B. those of formula (CV)
  • R 1 is hydrogen, methyl, ethyl, propyl or phenyl
  • R 127 is hydrogen, methyl, ethyl, propyl, butyl, - (CH 2 VCOO " , - (CH 2 VSO 3 - or - (CH 2 VO-SO 3 ") ,
  • R 128 is hydrogen, methyl, ethyl, propyl, butyl or phenyl,
  • R 121 and R 122 independently of one another represent hydrogen, methyl or - (CH 2 ) 1 -COO " , - (CH 2 VSO 3 " or - (CH 2 VO-SO 3 ”) ,
  • R 123 is methyl or trifluoromethyl
  • R 124 is cyano, methoxycarbonyl or ethoxycarbonyl
  • R 125 is phenyl, chlorophenyl or tolyl
  • R 129 and R 130 independently of one another represent hydrogen, methyl, ethyl, propyl or together represent a - (CH 2 V, - (CH 2 V, - (CH 2 ) 6 - bridge and
  • n is an integer from 3 to 5
  • R 127 , R 121 and R 122 is - (CH 2 VCOO " , - (CH 2 VSO 3 " or - (CH 2 VO-SO 3 " , preferably UOr- (CH 2 VSO 3 " .
  • anionic methine dyes are, for. B. those of the formula (CVI)
  • X 141 stands for O or S
  • X 142 is CR 150 or N
  • R 143 is hydrogen, C 1 - to C 6 -alkyl, halogen, hydroxy or C 6 - to C O -aryl,
  • R 141 and R 142 independently of one another represent hydrogen, C r to C 6 -alkyl, C 5 - to C 7 -
  • Cycloalkyl C 6 - to C 10 -aryl or C 7 - to cis-aralkyl or
  • NR 141 R 142 represents pyrrolidino, morpholino, piperazino or piperidino
  • R 150 is hydrogen, cyano, C 1 - to C 6 -alkyl, halogen or C 6 - to C O -aryl
  • Y 10S is furN or CR 1 ⁇
  • R 15S is hydrogen or cyano
  • X 104 is CR 151 or N
  • R 146 is hydrogen, C 1 - to C 6 -alkyl, halogen, hydroxy or C 6 - to C 10 -aryl or
  • R 143 and R 146 form an -O- or -C (CH 3 ) 2 bridge
  • R 144 and R 145 independently represent hydrogen, C 1 - to C 6 -AIk ⁇ l, C 5 - to C 7 - cycloalkyl, C 6 - to Cio-aryl or C 7 - to C 15 aralkyl, or are
  • NR 144 R 145 represents pyrrolidino, morpholino, piperazino or piperidino,
  • R 151 is hydrogen, cyano, C 1 - to C 6 -alkyl, halogen or C 6 - to C 10 -aryl ⁇
  • X 105 is nitrogen or ⁇ io5_ R i47 mr s;
  • X 106 is O, S, NR 159 , CR 160 or CR 160 R 161 ,
  • Y 109 stands for N or CR 158 ,
  • R 147 and R 159 independently represents d- to C 6 alkyl, C 3 - to C 6 -alkenyl, C 5 - to C 7 -
  • Cycloalkyl or C 7 - to C are 6 aralkyl
  • R 160 and R 11 independently of one another represent hydrogen or methyl
  • S together with X 105 , X 106 and the C atom bonded between them represents a five- or six-membered aromatic or quasi-aromatic or partially hydrogenated heterocyclic ring containing 1 to 4 heteroatoms and / or benzo or naphthanellated and / or nonionic Radicals can be substituted,
  • R 154 and R 155 independently represent hydrogen, C 1 - or to Cio-aryl or a heterocyclic radical - to C 16 alkyl, C 4 - to C 7 - cycloalkyl, C 7 - to C 6 aralkyl, C 6
  • NR 154 R 155 is a five- or six-membered, N-connected saturated ring which may additionally contain an N or O and / or may be substituted by nonionic radicals,
  • R 156 and R 156 ' independently of one another are hydrogen, C r to C 16 -alkyl, C 1 - to C 16 -alkoxy or halogen, or
  • R 156 ; R 154 and / or R 156 ' ; R 155 forms a two- or three-membered bridge which may contain an O or N and / or may be substituted by nonionic radicals,
  • R 157 represents hydrogen, C 1 - to C 16 -alkyl, C 1 - to C 16 -alkoxy, halogen, cyano, C 1 - to C 4 -alkoxycarbonyl, O-CO-R 162 , NR 163 -CO-R 162 , 0-SO 2 -R 162 or NR 163 -SO 2 -R 162 ,
  • R 162 is hydrogen, C 1 - to C 16 -alkyl, C 4 - to C 7 -cycloalkyl, C 7 - to C 16 -aralkyl, C 1 - to C 16 -alkoxy, mono- or BiS-C 1 - to C 16 -alkylamino, C 6 - to C 10 -aryl, C 6 - to
  • R 163 is hydrogen or C 1 - to C 4 -alkyl, in which
  • R 141 , R 142 ; R 144 , R 145 , R 147 , R 154 and R 155 for -CCH 2 ) n -COCr, - (CH 2 ) H -SO 3 " or - (CH 2 VO-SO 3 " , preferably for - (CH 2 ) n -SO 3 " and stand for
  • n is an integer from 2 to 5.
  • Nonionic radicals are, for example, halogen, alkyl, alkenyl, aralkyl, aryl, alkoxy,
  • Particularly preferred mixtures of azo metal complexes are those which comprise a nickel complex of the formula (Ia) having two identical ligands of the formulas (XIa) to (XId) and one nickel complexes of the formula (Ia) having two ligands of the formulas (XtVa) to
  • azo metal complexes are those which comprise a nickel complex of the formula (Ia) having two identical ligands of the formers (XIa) to (XId) and a nickel complexes of the formula (Ia) having two identical ligands of the formers (XVa) to (XVI ) contain.
  • particularly preferred mixtures of azo metal complexes are those which comprise a nickel complex of the formula (Ia) having two identical ligands of the formula (XIa) to (XId) and a nickel complex of the formula (Ia) having two identical ligands of the formulas (XVIa) to (XVHi).
  • Very particularly preferred mixtures of azo metal complexes are those which contain a nickel complex of the formula (Ia) having two identical ligands of the formula (XIa) and a nickel complexes of the formula (Ia) having two identical ligands of the formula (XTVa).
  • very particularly preferred mixtures of azo metal complexes are those which comprise a nickel complex of the formula (Ia) having two identical ligands of the formula (XIa) and a nickel complex of the formula (Ia) having two identical ligands of the formers (XVa),
  • R 0 in these particularly and very particularly preferred mixtures of azo metal complexes is preferably one of the following formers:
  • C 1 -C 5 -alkyl radicals are preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, which may be substituted by the radicals added above can.
  • substituted alkyl radicals are: perfluorinated
  • the particularly preferred azo metal complexes of the formula (Ia) each have 2 ligands, as can be taken from the formers (XI) to (XVT). It is assumed that they are in the form of the formulas (Ha) to (Hf):
  • the mixtures according to the invention may contain, in addition to the mixture of at least two azo metal complexes, further org. contain light-absorbing compounds ent.
  • the mixtures according to the invention consist of more than 95% by weight, in particular more than 98% by weight, of the mixture of the at least two azo metal complexes.
  • the azo metal complexes may contain solvents in the crystal.
  • the crystal does not contain more than two molecules of solvent per molecule of azometallic complex, more preferably not more than one molecule of solvent.
  • solvents may be water, alcohols such as methanol, ethanol, propanol, diacetone alcohol or 2,2,3,3-Tetrafluorpropa ⁇ ol, ketones such as acetone or butanone, dipolar solvents such as acetonitrile, N-methylpyrrolidone or dimethylformamide or mixtures thereof.
  • the mixtures according to the invention come in particular as powder or granules or as a solution having a solids content of at least 2 wt .-% in the trade. Preference is given to the granulate form, in particular granules having an average particle size of 50 ⁇ m to
  • Such granules can be prepared, for example, by spray drying.
  • the granules are characterized in particular by their dust poverty.
  • the mixtures according to the invention are distinguished by good solubility. They are readily soluble in non-fluorinated and fluorinated alcohols. Preference is given to fluorinated alcohols. Such alcohols are, for example, those having 3 to 9 C atoms, preferably propanol, butanol, pentanol, hexanol, diacetone alcohol, 2,2,3,3-tetrafluoropropanol, octafluoropentanol or else mixtures of these alcohols, such as e.g. Propanol / diacetone alcohol, butanol / diacetone alcohol, butanol / hexanol, butanol / nonanol. Preferred mixing ratios for the listed mixtures are, for example
  • the preferred solvent is 2,2,3,3-tetrafluoropropanol, propanol, butanol,
  • the solutions according to the invention preferably contain only the mixtures according to the invention consisting of more than 95% by weight, in particular more than 98% by weight, of the two azo metal complexes 1 and 2.
  • the invention further relates to the use of the mixtures according to the invention of at least two azo metal complexes as light-absorbing compounds in the information layer of write-once optical data carriers.
  • the optical data carrier is preferably written and read with red laser light, in particular with a wavelength in the range of 600-700 nm, particularly preferably in the range of 625-660 nm.
  • the invention further relates to an optical data carrier, comprising a preferably transparent, optionally already coated with one or more reflective layers substrate on the surface of a writable light information layer, optionally one or more reflective layers and optionally a protective layer or another substrate or a cover layer are applied, which with red light, preferably with a wavelength in the range of 600-700 nm, preferably from 620 to 680 nm, most preferably from 625 to 660 nm, preferably
  • Laser light can be written and read, wherein the information layer contains a licht ⁇ absorbing compound and optionally a binder, characterized in that the mixture according to the invention is used as the light-absorbing compound.
  • an optical data carrier containing a preferably transparent substrate, on the surface of which a light-writable information layer, one or more reflection layers and a protective layer or another substrate or a cover layer are applied, which is coated with red light, preferably with a wavelength in the Range of 600-700 nm, preferably from 620 to 680 nm, most preferably from 625 to 660 nm, preferably laser light, can be described and read, the
  • Information layer contains a light-absorbing compound and optionally a binder, characterized in that as a light-absorbing compound erfindungs ⁇ proper mixture is used.
  • the light-absorbing compound should preferably be thermally changeable.
  • the thermal change takes place at a temperature ⁇ 600 ° C, more preferably at a temperature ⁇ 400 ° C, most preferably at a temperature ⁇ 300 ° C, in particular> 200 ° C.
  • Such a change may be, for example, a decomposition or chemical change of the chromophore 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 embodiments of the mixture of azo metal complexes according to the invention.
  • it is a mixture containing a complex 1 of the formula (Ia) with a ligand of Formulas (XI) to (XHI), more particularly of the formulas (XIa) to (XId), and as Complex 2 one of the formula (Ia) with a ligand of the formulas (XTV) to (XVT), especially of the formulas (XIVa ) to (XTVd), (XVa) to (XVl) and (XVIa) to (XVIh).
  • the Info ⁇ nations slaughter contains as light-absorbing compound only a mixture according to the invention consisting of more than 95 wt .-%, in particular more than 98 wt .-% of the two Azometallkomplexen 1 and 2.
  • the light-absorbing compounds used according to the invention guarantee a sufficiently high reflectivity (preferably> 10%, in particular> 20%, very particularly> 40%) of the optical data carrier in the unrecorded state and a sufficiently high absorption for thermal degradation of the information layer at point-specific
  • the contrast between written and unwritten locations 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 the thermal degradation.
  • the light-absorbing compounds used according to the invention guarantee a high light resistance of the unwritten optical data carrier as well as the information inscribed on the data carrier against daylight, sunlight or under increased artificial irradiation for imitation of daylight.
  • the light-absorbing compounds used according to the invention guarantee a high level of
  • the light-absorbing compounds preferably used according to the invention are stable enough so that the disk produced with them fulfills the required climatic test.
  • the mixtures of azometaU complexes according to the invention are preferably applied to the optical data carrier by spin coats. As a rule, they are used alone. However, it is also possible for such mixtures according to the invention to be mixed with one another or else with other dyes having similar spectral properties.
  • the information layer may contain, in addition to the light-absorbing compound, additives such as binders, wetting agents, stabilizers, thinners and sensitizers, as well as other ingredients. Preferably, the information layer does not contain such additives.
  • additives such as binders, wetting agents, stabilizers, thinners and sensitizers, as well as other ingredients.
  • the information layer does not contain such additives.
  • To the Spin coats are preferably used the solutions according to the invention listed above.
  • the optical data storage device can carry, in addition to the information layer, further layers such as metal layers, dielectric layers and protective layers.
  • Metals and dielectric layers serve u. a. for adjusting the reflectivity and the
  • Metals may, depending on laser wavelength, gold, silver, aluminum, alloys of these metals u. a. be.
  • 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 consist mainly of acrylic adhesives. Nitto Denko DA-
  • 8320 or DA-8310 disclosed in JP-A 11-273147, can be used for this purpose.
  • Protective films are preferably made of translucent material, preferably plastic films. Suitable materials include polycarbonate, copolycarbonates, PMMA and cyclic polyolefins. The thickness is, for example, 5 to 200 .mu.m, preferably 10 to 180 .mu.m, more preferably 20 to 150 .mu.m, most preferably 50 to 120 .mu.m.
  • Photo-curable lacquers are, for example, UV-curable lacquers. These are, for example, acrylates and methacrylates, as described, for example, in P.K. Oldring (Ed.), Chemistry & Technology of UV & EB Formulations for Coatings, Inks & Paints, Vol.
  • the thickness is, for example, 5 to 200 .mu.m, preferably 10 to 180 .mu.m, more preferably 20 to 150 .mu.m, most preferably 50 to 120 .mu.m.
  • the optical data carrier preferably contains at least one substrate.
  • the substrate material is preferably transparent.
  • the thickness is preferably 0.3 mm, or more preferably at least 0.6 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 has, for example, the following layer structure (see Fig. 1): a preferably transparent substrate (11), an information layer (12), optionally one
  • the optical data carrier preferably contains an information layer (12).
  • the optical data carrier contains a reflection layer (13).
  • the optical data carrier contains a second substrate (15).
  • the optical data carrier contains a substrate (11) or (15) of polycarbonate or copolycarbonate.
  • the substrate (11) and (15) 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 as follows:
  • a transparent substrate 11
  • an information layer (12) which can be written on and read with light, preferably laser light
  • a reflection layer 13
  • an adhesive layer 14
  • a further transparent substrate 15
  • optical data carriers which contain two layers of information. They can be structured, for example, as follows:
  • a preferably transparent substrate 11
  • an information layer (12), optionally a reflection layer (13), optionally an adhesive layer (14), optionally a protective or dielectric layer, optionally an adhesive layer (14), optionally a reflection layer (13), an information layer (12), another preferably transparent substrate (15).
  • a preferably transparent substrate 11
  • an information layer (12), optionally a reflection layer (13), optionally an adhesive layer (14), optionally a protective or dielectric layer, an information layer (12), optionally a reflection layer (13) , another preferably transparent substrate (15).
  • these optical data carriers with two information frames contain at least one reflection layer and at least one adhesive layer.
  • the invention further relates to red light, preferably with light of wavelength 600-700 nm, in particular 620-660 nm, preferably 625 to 660 nm, in particular laser light described optical data carrier according to the invention.
  • Lithium perchlorate was interspersed. After stirring for 30 minutes, it was slowly added to 100 ml Water discharged. After aspirating, washing with 10 ml of water and drying at 50 0 C in vacuo gave 4.8 of a purple powder of mp. 309 0 C (dec.).
  • Solubility > 2% in TFP (2,2,3,3-tetrafluoropropanol) glassy film.
  • Dye mixture prepared in 2,2,3,3-tetrafluoropropanol consisted of three parts by mass of the azo metal complex of the formula (IIIa) of Example 1 and two parts by mass of the azo metal complex of the formula (LIVa) of Example 4. This solution was applied by spin coating on a pregrooved polycarbonate substrate.
  • the pregrooved polycarbonate substrate was made by injection molding as a disk.
  • the disk with the dye layer as information carrier was vapor-deposited with 100 nm of silver. Subsequently, a second disk was glued to the silver layer of the first with UV-curable acrylic paint. The thus-finished disc was burned by a commercial burner Plextor PX-708US at 4 times speed.
  • the written data on the disk was analyzed by a reference drive (Datarius CS4). The modulation of the 14T pit was 66% and the bottom jitter was 6.91%.
  • Limits 1 to 5 were varied.
  • the discs can be written with at least 4x (4x) to at least 8x (8x) write speed.

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

Abstract

L'invention concerne des mélanges contenant au moins deux complexes métalliques azoïques différents contenant, à leur tour, des ligands de la formule (I) où les substituants ont la définition donnée dans la revendication 1.
PCT/EP2005/007352 2004-07-19 2005-07-07 Melanges de complexes metalliques azoiques utilises comme composes absorbant la lumiere dans la couche de donnees de supports de donnees otiques WO2006007983A1 (fr)

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DE102004034866A DE102004034866A1 (de) 2004-07-19 2004-07-19 Mischungen von Azometallkomplexen als lichtabsorbierende Verbindungen in der Informationsschicht von optischen Datenträgern
DE102004034866.9 2004-07-19

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EP1925642A1 (fr) * 2006-11-27 2008-05-28 Clariant International Ltd. Colorants azoïques à base de 3-hydroxy-cyclohex-2-énone et leurs utilisations avec des colorants complexes métallo-azo-anioniques

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