EP1488418A1 - Colorants squarylium servant de composes photo-absorbants dans la couche d'informations de supports de donnees optiques - Google Patents

Colorants squarylium servant de composes photo-absorbants dans la couche d'informations de supports de donnees optiques

Info

Publication number
EP1488418A1
EP1488418A1 EP03744371A EP03744371A EP1488418A1 EP 1488418 A1 EP1488418 A1 EP 1488418A1 EP 03744371 A EP03744371 A EP 03744371A EP 03744371 A EP03744371 A EP 03744371A EP 1488418 A1 EP1488418 A1 EP 1488418A1
Authority
EP
European Patent Office
Prior art keywords
light
formula
optionally substituted
optionally
trifluoromethylbenzyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03744371A
Other languages
German (de)
English (en)
Inventor
Horst Berneth
Friedrich-Karl Bruder
Wilfried Haese
Karin HASSENRÜCK
Serguei Kostromine
Peter Landenberger
Thomas Sommermann
Josef-Walter Stawitz
Rainer Hagen
Rafael Oser
Christa Maria KRÜGER
Timo Meyer-Friedrichsen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanxess Deutschland GmbH
Original Assignee
Bayer Chemicals AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE10245581A external-priority patent/DE10245581A1/de
Application filed by Bayer Chemicals AG filed Critical Bayer Chemicals AG
Publication of EP1488418A1 publication Critical patent/EP1488418A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/007—Squaraine 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
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with 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
    • 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
    • G11B7/248—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 porphines; azaporphines, e.g. phthalocyanines
    • 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
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/254—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers
    • G11B7/2542—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers consisting essentially of organic resins
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/258—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers
    • G11B7/259—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers based on silver

Definitions

  • the invention relates to squarylium dyes, a process for their preparation, the components on which the squarylium dyes are based and their production, and optical data memories which contain the squarylium dyes in their information layer.
  • the write-once optical data carriers using special light-absorbing substances or their mixtures are particularly suitable for use with DVD-R discs that work with red (635 - 660 nm) laser diodes, and the application of the above-mentioned dyes to a polymer substrate, especially polycarbonate, by spin coating.
  • the recordable format in this case is the DVD-R.
  • the storage density that can be achieved depends on the focus of the laser spot in the information level.
  • the spot size scales with the laser wavelength ⁇ / NA.
  • NA is the numerical aperture of the objective lens used.
  • the aim should be to use the smallest possible wavelength ⁇ . 390 nm are currently possible on the basis of semiconductor laser diodes.
  • 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. For this purpose, it is particularly preferred that when the substances are applied by spin coating from a solution, by vapor deposition and / or
  • 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, can form blurred interfaces via diffusion and thus adversely affect the reflectivity.
  • a light-absorbing substance with too low heat resistance at the interface to a polymer carrier can diffuse in it and in turn adversely affect the reflectivity.
  • An excessively high vapor pressure of a light-absorbing substance can sublimate the above-mentioned sputtering or vapor deposition of further layers in a high vacuum and thus reduce the desired layer thickness. This in turn leads to a negative influence on the reflectivity.
  • the object of the invention is accordingly to provide suitable connections which meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the information layer in a write-once optical data carrier for writable optical data storage media.
  • the invention therefore relates to squarylium compounds of the general formula I
  • R represents a heterocyclic five-membered ring, in particular an optionally substituted pyrrole, with the exception of amino-substituted furan rings.
  • R 1 represents hydrogen, optionally substituted alkyl or optionally substituted aralkyl
  • R 2 represents optionally substituted alkyl, optionally substituted aryl, alkoxycarbonyl or optionally substituted alkylcarbonyl
  • R 1 represents hydrogen, optionally substituted alkyl or optionally substituted aralkyl
  • R 2 represents optionally substituted alkyl, optionally substituted aryl, alkoxycarbonyl or optionally substituted alkylcarbonyl
  • R 3 and R 4 independently of one another represent hydrogen, optionally substituted alkyl, optionally substituted aryl, alkoxycarbonyl or optionally substituted alkylcarbonyl.
  • Formula la represents one of the possible mesomeric formulas.
  • alkyl is preferably understood to mean C 1 -C 6 -alkyl
  • aryl is preferably C 1 -C 6 -aryl
  • aralkyl is preferably C 7 -C 6
  • alkoxy is preferably CJ-C ⁇ - alkoxy.
  • Halogen in particular F, hydroxy, nitro, cyano, carboxyl, alkoxy, trialkylsilyl or, come as possible substituents of the alkyl, aryl or aralkyl radicals
  • alkyl radicals can be straight-chain, cyclic or branched. They can be partially or perhalogenated. Examples of substituted alkyl radicals are trifluoromethyl. Chloroethyl, cyanoethyl, methoxyethyl. Examples of cyclic
  • Alkyl radicals are cyclohexylmethyl and cyclopropylmethyl.
  • Examples of branched alkyl radicals are isopropyl, tert-butyl, 2-butyl, neopentyl. Examples of possible
  • Aryl radicals are phenyl, 4-methoxyphenyl, 4-cyanophenyl, 3,5-bis (trifluoromethyl) phenyl, 4-trifluoromethylphenyl and 4-ethyl ⁇ henyl.
  • Examples of aralkyl radicals are benzyl, phenethyl, phenylpropyl, 4-methoxybenzyl, 4-cyanobenzyl, 3,5-
  • alkylcarbonyl examples include acetyl, trifluoroacetyl, propanoyl, butanoyl,
  • Pentanoyl and hexanoyl are Pentanoyl and hexanoyl.
  • Preferred optionally substituted alkyl radicals are methyl, ethyl, n-propyl, n-pentyl, isobutyl, isopropyl, perfluorinated methyl and ethyl.
  • Examples of preferred optionally substituted aralkyl include 4-trifluoromethylbenzyl, 2-trifluoromethylbenzyl, 3,5-bistrifluoromethylbenzyl and 4-fluoro-2-trifluoromethylbenzyl.
  • the preferred alkoxycarboxyl radical is ethoxycarbonyl.
  • R 1 is hydrogen, methyl, ethyl, propyl, butyl, cyclohexylmethyl, benzyl, 4-methoxybenzyl, 4-trifluoromethylbenzyl, 3-trifluoromethylbenzyl, 2-trifluoromethylbenzyl, 3,5-bis (trifluoromethyl) benzyl or 4-fluoro-2 -trifluoromethyl-benzyl,
  • R 2 represents methyl, ethyl, propyl or phenyl
  • R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, phenyl, acetyl or ethoxycarbonyl.
  • R 1 represents 4-trifluoromethylbenzyl or 3,5-bis (trifluoromethyl) benzyl, in particular 2-trifluoromethylbenzyl,
  • R 2 represents methyl, ethyl or phenyl, in particular methyl
  • R 3 represents hydrogen, ethyl, acetyl or ethoxycarbonyl, in particular ethyl, and
  • R 4 represents methyl, ethyl or phenyl, especially methyl or ethyl.
  • the invention further relates to a process for the preparation of the squarylium compounds according to the invention, which is characterized in that 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid) with at least one compound of the formula III
  • R 5 represents hydrogen, alkoxycarbonyl, in particular t-butoxycarbonyl or ethoxycarbonyl or carboxyl, and
  • R and R 1 to R 4 have the meanings given above.
  • the process according to the invention is preferably carried out in alcohol, in particular in ethanol.
  • Preferred reaction temperatures are greater than 70 ° C, especially 75-85 ° C.
  • the process according to the invention is also preferably carried out in aqueous acetic acid.
  • the mixing ratio of acetic acid / water is, for example, 3: 1 to 1: 3, preferably 2: 1 to 1: 2, particularly preferably 1: 1.
  • Preferred reaction temperatures are from room temperature to the boiling point of the medium. It is also preferred to use a catalytic amount
  • the product generally falls as a pure solid from the reaction solution and is preferably washed with ether after the separation.
  • pyrrole compounds of the formula (purple) which are preferably used to prepare the squarylium compounds according to the invention are also the subject of these
  • the invention therefore also relates to pyrroles of the formula (purple)
  • R 1 represents optionally substituted C 1 -C 4 -alkyl or optionally substituted aralkyl
  • R 2 represents optionally substituted alkyl, optionally substituted aryl, alkoxycarbonyl, carbonyl or optionally substituted alkylcarbonyl,
  • R 3 and R 4 are independently hydrogen, optionally substituted
  • Alkyl optionally substituted aryl, alkoxycarbonyl, carbonyl or optionally substituted alkoxycarbonyl and
  • R 5 represents hydrogen, alkoxycarbonyl or carboxyl.
  • R 2 represents methyl, ethyl, propyl or phenyl
  • R 3 and R 4 independently of one another are hydrogen, methyl, ethyl, propyl, butyl, phenyl, acetyl or ethoxycarbonyl, and
  • R 5 represents hydrogen, t-butoxycarbonyl or carboxyl.
  • the invention also relates to a process for the preparation of the pyrrole compounds of the formula purple according to the invention, which is characterized in that a pyrrole compound of the formula (II)
  • R 2 to R 4 have the meaning given above for the pyrroles of the formula lilac and
  • R 5 represents hydrogen, Ajkoxycarbonyl, especially t-butoxycarbonyl, ethoxycarbonyl or carboxyl
  • R 1 has the meaning given for the pyrroles of the formula purple according to the invention
  • X stands for CI, Br or I
  • KOH is particularly suitable as a suitable base. It is preferred to carry out the reaction in a suitable solvent, for example in dimethyl sulfoxide (DMSO), dimethylformamide (DMF) or a mixture thereof. The reaction is preferably carried out at a temperature of 20-100 ° C, particularly preferably 50-90 ° C, in particular 65-80 ° C.
  • R 5 in formula II equal to ethoxycarbonyl, the ester group is converted into the corresponding alkali salt
  • Saponified pyrrole carboxylic acid This can be precipitated from aqueous solution by acidification and filtered off.
  • the product can be obtained in sufficient purity without complex crystallization or similar cleaning steps.
  • the invention further relates to the use of the squarylium dyes 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 red laser light, in particular with a wavelength in the range of 600-680 nm.
  • the invention further relates to the use of squarylium compounds as a light-absorbing compound in the one-time writable information layer optical data carriers, wherein the optical data carrier can be written and read with red laser light, in particular with a wavelength in the range of 600-680 nm.
  • the invention further relates to an optical data carrier containing a preferably transparent substrate, on the surface of which an information layer which can be written on with light, optionally one or more reflection layers and a further substrate or a protective layer are applied, which is covered with red light, preferably with a wavelength in the range 600-680 nm, preferably laser light, can be described and read, the information layer containing a light-absorbing compound and optionally a binder, characterized in that at least one squarylium dye according to the invention is used as the light-absorbing compound.
  • 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.
  • a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
  • the light-absorbing compound can only be changed thermally above 100 ° C.
  • the preferred embodiments of the light-absorbing compounds in the optical data memory according to the invention correspond to the preferred embodiments of the squarylium dye according to the invention.
  • the light-absorbing compounds used are those of the formula (Ia) wherein
  • R 1 represents hydrogen, methyl, ethyl, propyl, butyl, cyclohexylmethyl, benzyl, 4-methoxybenzyl, 4-trifluoromethylbenzyl, 3-trifluoromethylbenzyl or 3,5-bis (trifluoromethyl) benzyl,
  • R 2 , R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, phenyl, acetyl or ethoxycarbonyl.
  • the light-absorbing compound used is that of the formula (Ia)
  • R 2 and R 4 independently of one another represent methyl, ethyl or phenyl, in particular methyl or ethyl, and
  • R 3 represents hydrogen, ethyl, acetyl or ethoxycarbonyl, in particular ethyl.
  • those light-absorbing compounds are preferred whose absorption maximum ⁇ max is in the range
  • Such a light-absorbing compound preferably has up to to a wavelength of 750 nm, particularly preferably 800 nm, very particularly preferably 850 nm, no longer-wave maximum ⁇ max3 .
  • Light-absorbing compounds with an absorption maximum ⁇ max of 510 to 620 nm are preferred.
  • Light-absorbing compounds with an absorption maximum ⁇ max of 530 to 610 nm are particularly preferred.
  • Light-absorbing compounds with an absorption maximum ⁇ max of 550 to 600 nm are very particularly preferred.
  • These light-absorbing compounds ⁇ / 2 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 preferably have a molar extinction coefficient ⁇ > 60,000 1 / mol cm, preferably> 80,000 1 / mol cm, particularly preferably> 100,000 1 / mol cm, very particularly preferably> 120,000 1 / mol cm.
  • One method To determine such a dipole moment change ⁇ for example in F. Würthner et al., Angew. Chem. 1997, 109, 2933 and in the literature cited therein.
  • Low solvatochromism dioxane / DMF is also a suitable selection criterion.
  • the absorption spectra are preferably measured in solution.
  • the light-absorbing compounds used according to the invention preferably enable a reflectivity of> 10% of the optical data carrier in the blank state and a sufficiently high absorption for the thermal degradation of the information layer in the case of selective illumination with focused light if the light wavelength is in the range from 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 squarylium dyes according to the invention are preferably applied to the optical data carrier by 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
  • the optical data memory according to the invention can carry further layers such as metal layers, dielectric layers and protective layers.
  • Metals and dielectric layers serve u. a. to adjust the optical data memory
  • metals can be gold, silver, aluminum and others.
  • Dielectric layers are, for example, silicon dioxide or 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. 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 substrate (15) is preferably replaced by a layer sequence (13),
  • the structure of the optical data carrier can be:
  • Photocurable lacquers are particularly preferred as separating layers.
  • arrows shown in Fig. 1, Fig. 2 and Fig. 3 represent the path of the irradiated
  • the invention further relates to red light, in particular red laser light, particularly preferably to the optical data carrier according to the invention described with a wavelength at 600-680 nm.
  • the invention also relates to a write-once optical data carrier which contains at least one phthalocyanine dye in the information layer as a light-absorbing compound, and to a process for its production.
  • the object of the invention is accordingly to provide suitable connections which meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the information layer in a write-once optical data carrier, in particular for high density fulfill writable optical data storage formats in a laser wavelength range from 360 to 460 nm.
  • Phthalocyanines show an intensive absorption in the 360 - 460 nm wave range that is important for the laser, the so-called B or Soret band.
  • the present invention therefore relates to an optical data carrier, comprising a preferably transparent substrate, possibly already coated with one or more reflection 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 Cover layer are applied, which with blue light, preferably laser light, particularly preferably light with a wavelength of 360-460 nm, in particular 380-420 nm, very particularly preferably at 390-410 nm, or with infrared light, preferably laser light, particularly preferably light with a Wavelength of 760-830 nm, can be described and read, the information layer containing a light-absorbing compound and optionally a binder, characterized in that at least one phthalocyanine of the formula (I) is used as the light-absorbing compound det
  • Pc stands for an unsubstituted phthalocyanine
  • X and X are independently bromine or iodine and X can additionally represent chlorine.
  • Phthalocyanines of the formula (Ia), (Ib), (Ic), (Id), (Le), (If), (Ig) and (Da) are preferred.
  • the phthalocyanines used according to the invention are, for example, from J.N.
  • Me Sn
  • X and X are halogen, for example chlorine.
  • a suitable reducing agent is, for example, sodium tetrahydroborate
  • the light absorbing compounds are thermally changeable.
  • the thermal change preferably takes place at a temperature of ⁇ 600 ° C.
  • Such a change can be, for example, a decomposition or chemical change in the chromophoric center of the light-absorbing compound.
  • the light-absorbing substances described guarantee a sufficiently high reflectivity of the optical data carrier in the blank state as well as a sufficiently high absorption for the thermal degradation of the information layer in the case of selective illumination with focused blue light, in particular laser light, preferably with a light wavelength in the range from 360 to 460 nm.
  • the contrast between the described 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.
  • optical data carrier can preferably be written and read with laser light with a wavelength of 360-460 nm.
  • the optical data carrier can also be written and read with infrared light, in particular laser light with a wavelength of 760-830 nm, in which case the groove distance and geometry are preferably adapted to the wavelength and numerical aperture.
  • the invention further relates to the use of the phthalocyanines of the formula (I) as light-absorbing compounds in the information layer of optical storage media.
  • the invention also relates to the use of the phthalocyanines of the formula (I) for the production of optical storage media.
  • the phthalocyanines are preferably used in the information layer as light-absorbing compounds.
  • the phthalocyanines particularly preferred in these uses have a content of more than 90% by weight, in particular more than 95% by weight, particularly preferably more than 98% by weight, based on the phthalocyanine of the formula
  • the invention further relates to a particulate solid preparation of a phthalocyanine of the formula (I), characterized in that the particles have an average particle size of 0.5 ⁇ m to 10 mm.
  • finely divided powder In a preferred embodiment of the particulate solid preparations, those are preferred which have an average particle size of 0.5 to 20 ⁇ m, in particular 1 to 10 ⁇ m - hereinafter referred to as finely divided powder. Such finely divided powders can be produced, for example, by grinding.
  • particulate solid preparations with an average particle size of 50 to 300 ⁇ m - hereinafter referred to as fine crystalline form.
  • Further preferred particulate solid preparations are those with an average particle size of 50 ⁇ m to 10 mm, preferably 100 ⁇ m to 800 ⁇ m, which as
  • Such moldings can have the shape of drops, raspberries, scales or sticks, for example - hereinafter referred to as granules.
  • the particle size of the finely crystalline form can be set, for example, by means of the synthesis parameters.
  • rapid heating for example in the range from 30 to 60 min, of the mixture of the components (phthalonitrile or aminoimino-isoindole and the corresponding metal halide in the corresponding solvent) to the reaction temperature, for example from 160 to 220 ° C.
  • the metal halide is only added to the reaction mixture (phthalodinitrile or aminoimino-isoindole in the appropriate solvent) at reaction temperature, for example at 160 to 190 ° C.
  • a coarse particle shape is preferably formed by, for example, slow heating, for example in the range from 65 to 250 min, of the mixture of the components to the reaction temperature, for example 160 to 220 ° C.
  • the particulate solid preparations according to the invention preferably contain
  • the solid preparations according to the invention are preferably low-dust, free-flowing and are notable for good storage stability.
  • the granules can be produced in various ways, e.g. by spray drying granulation, fluidized bed spray granulation, fluidized bed build-up granulation or powder-fluidized bed agglomeration.
  • Granulation by spray drying is preferred, with both rotary disks and single-substance or two-substance nozzles being suitable as the spray element.
  • the inlet and outlet temperatures for spray drying depend on the desired residual moisture, safety measures and economic considerations.
  • the inlet temperature is preferably 120-200 ° C, in particular 140-180 ° C, and the outlet temperature preferably 40-80 ° C.
  • the procedure is generally such that the colorant filter cake is mixed intensively, if appropriate, with auxiliaries and additives in a stirred kettle.
  • the crystals of the suspension are preferably comminuted in a mill, for example a bead mill, so that a finely divided, sprayable suspension is obtained.
  • the dye suspension is an aqueous suspension.
  • the granulation takes place during spray drying.
  • the invention further relates to solid moldings such as tablets, rods, etc. containing a phthalocyanine of the formula (I), preferably in an amount of more than 90% by weight, in particular more than 95% by weight, preferably more than 98% by weight. %, based on the molded body.
  • a phthalocyanine of the formula (I) preferably in an amount of more than 90% by weight, in particular more than 95% by weight, preferably more than 98% by weight. %, based on the molded body.
  • Other ingredients of the solid moldings can be binders.
  • the sums of phthalocyanine of the formula (I) and binder preferably add up to more than 95% by weight, preferably more than
  • Such moldings can be produced, for example, by pressing the phthalocyanine of the formula (I), if appropriate in the presence of binders, at a pressure of 5 to 50 bar, preferably 10 to 20 bar.
  • the invention also relates to dispersions, preferably aqueous dispersions, containing a metal complex of the formula (I), preferably in an amount of 10 to 90% by weight, based on the dispersion.
  • suitable dispersants are: polymeric dispersants based on acrylate, urethanes or long-chain polyoxyethylene compounds.
  • Suitable products are, for example: Solsperse 32000 or Solsperse 38000 from Avecia.
  • the invention further relates to a method for coating substrates with the phthalocyanines of the formula (I). It is preferably done by spin coating,
  • the starting material for such coatings by sputtering or vacuum vapor deposition are all of the above-mentioned forms of the phthalocyanines of the formula (I), ie. H. finely divided powders, fine crystalline forms or granules, particulate solid preparations, solid moldings and dispersions.
  • the latter serve, in particular, to apply the phthalocyanines in finely divided form to a surface from which they can then be applied to the substrate by sputtering or vacuum evaporation.
  • degrees of purity of the phthalocyanines greater than 50%, particularly preferably greater than 85% and very particularly preferably greater than 90%, in particular greater than 95% or greater than 98% are preferred.
  • the phthalocyanines 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 other constituents.
  • the invention further relates to an apparatus for evaporating light-absorbing compounds onto a substrate for producing optical storage media, which is characterized in that the dye is evaporated by heating at low background pressure and deposited on the substrate
  • the background pressure is below 10 Pa, preferably below 10 * Pa, more preferably below 10 "4 Pa.
  • the heating of the dye is preferably effected by resistive heating or by microwave absorption.
  • the invention relates in particular to an optical data carrier as described above, the light-absorbing compound of the formula (I), optionally together with the additives mentioned, forming an information layer, which is optically amorphous.
  • Amo h is understood to mean that no crystallites can be observed by light microscopy and that no X-rays can be used to observe Bragg reflections but only an amorphous halo.
  • 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, alloys, etc. his.
  • Dielectric layers are, for example, silicon dioxide and silicon nitride.
  • Protective layers are, for example photocurable,
  • the adhesive layers can be pressure sensitive.
  • Pressure-sensitive adhesive layers mainly consist of acrylic adhesives.
  • Denko DA-8320 or DA-8310 disclosed in patent JP-A 11-273147, can be used for this purpose, for example.
  • the optical data carrier 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).
  • the structure of the optical data carrier can preferably:
  • a preferably transparent substrate (1) on the surface of which at least one information layer (3) which can be written on with light and which can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a transparent pension cover layer (6) are applied.
  • a preferably 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 transparent substrate (1) on the surface of which there is optionally a protective layer (2), at least one information layer (3) that can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a transparent pension cover layer (6) are applied.
  • a transparent substrate (1) on the surface of which at least one information layer (3), optionally an adhesive layer (5), which can be written on with light, preferably laser light, and a transparent 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 optical data carrier has, for example, the following layer structure (cf. FIG. 3): a preferably transparent substrate (21), a formation layer (22), optionally a reflection layer (23), a protective layer (24).
  • the structure of the optical data carrier can be:
  • the invention further relates to optical data carriers according to the invention described with blue light, in particular laser light, particularly preferably laser light with a wavelength of 360-460 nm.
  • Suitable squarylium dyes are listed in the table. These are obtained by analogous production of the components or squarylium dyes.
  • the dye dibromo-germanium-phthalocyanine (GeBr Pc) was in a high vacuum
  • the disc was irradiated with this pulse sequence until it had turned around once.

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

Abstract

L'invention concerne de nouveaux composés de squarylium conçus pour des supports de données optiques. Un substrat de préférence transparent comprenant à sa surface une couche d'informations inscriptible au moyen d'une lumière, éventuellement une ou plusieurs couches de réflexion et un autre substrat ou une couche de protection sont appliqués sur lesdits supports de données optiques qui sont inscriptibles et lisibles au moyen d'une lumière rouge, de préférence d'une lumière laser. La couche d'informations contient un composé photo-absorbant et éventuellement un liant. L'invention est caractérisée en ce qu'au moins le composé de squarylium est utilisé en tant que composé photo-absorbant.
EP03744371A 2002-03-19 2003-03-18 Colorants squarylium servant de composes photo-absorbants dans la couche d'informations de supports de donnees optiques Withdrawn EP1488418A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10212199 2002-03-19
DE10212199 2002-03-19
DE10245581A DE10245581A1 (de) 2002-03-19 2002-09-27 Squaryliumfarbstoffe als lichtabsorbierende Verbindung in der Informationsschicht von optischen Datenträgern
DE10245581 2002-09-27
PCT/EP2003/002789 WO2003079339A1 (fr) 2002-03-19 2003-03-18 Colorants squarylium servant de composes photo-absorbants dans la couche d'informations de supports de donnees optiques

Publications (1)

Publication Number Publication Date
EP1488418A1 true EP1488418A1 (fr) 2004-12-22

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EP03744371A Withdrawn EP1488418A1 (fr) 2002-03-19 2003-03-18 Colorants squarylium servant de composes photo-absorbants dans la couche d'informations de supports de donnees optiques

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Country Link
US (1) US20050142489A1 (fr)
EP (1) EP1488418A1 (fr)
JP (1) JP2005520835A (fr)
CN (1) CN1643587A (fr)
AU (1) AU2003226651A1 (fr)
WO (1) WO2003079339A1 (fr)

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JP2008501548A (ja) * 2004-06-03 2008-01-24 クラリアント・インターナシヨナル・リミテツド 光学データ記録用光学層におけるスクアリン酸色素の使用
JP5286726B2 (ja) * 2007-09-25 2013-09-11 富士ゼロックス株式会社 黒色色材及びトナー
US7667047B2 (en) * 2008-03-26 2010-02-23 Fuji Xerox Co., Ltd. Colorant
US9353092B2 (en) 2013-06-27 2016-05-31 University Of Notre Dame Du Lac Synthesis and use of croconaine compounds
JP6506529B2 (ja) * 2014-10-20 2019-04-24 株式会社日本触媒 オキソカーボン系化合物を含む樹脂組成物及びこれからなる成形体
JP6638948B2 (ja) * 2014-10-20 2020-02-05 国立大学法人愛媛大学 新規オキソカーボン系化合物
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AU2003226651A1 (en) 2003-09-29
US20050142489A1 (en) 2005-06-30
CN1643587A (zh) 2005-07-20
WO2003079339A1 (fr) 2003-09-25
JP2005520835A (ja) 2005-07-14

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