WO2007006417A2 - Phthalocyaninsulfonamides axialement substitues utilises comme composes absorbant la lumiere dans la couche d'informations de supports de donnees optiques - Google Patents

Phthalocyaninsulfonamides axialement substitues utilises comme composes absorbant la lumiere dans la couche d'informations de supports de donnees optiques Download PDF

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Publication number
WO2007006417A2
WO2007006417A2 PCT/EP2006/006183 EP2006006183W WO2007006417A2 WO 2007006417 A2 WO2007006417 A2 WO 2007006417A2 EP 2006006183 W EP2006006183 W EP 2006006183W WO 2007006417 A2 WO2007006417 A2 WO 2007006417A2
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WO
WIPO (PCT)
Prior art keywords
cation
light
layer
optical data
formula
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Application number
PCT/EP2006/006183
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German (de)
English (en)
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WO2007006417A3 (fr
Inventor
Horst Berneth
Karin HASSENRÜCK
Timo Meyer-Friedrichsen
Ulrich Feldhues
Josef-Walter Stawitz
Friedrich-Karl Bruder
Rafael Oser
Original Assignee
Lanxess Deutschland Gmbh
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Application filed by Lanxess Deutschland Gmbh filed Critical Lanxess Deutschland Gmbh
Publication of WO2007006417A2 publication Critical patent/WO2007006417A2/fr
Publication of WO2007006417A3 publication Critical patent/WO2007006417A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26—Amide radicals
    • 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

Definitions

  • the write-once optical data carriers using special light-absorbing substances or mixtures thereof are particularly suitable for use in high-density writable optical data storage, which work with blue laser diodes, in particular GaN or SHG laser diodes (360-460 nm).
  • optical data storage formats using blue laser diodes (base GaN, JP 08191171 or Second Harmony Generation SHG JP 09050629) (360 nm to 460 nm) with high laser power. Recordable optical data storage will therefore also be used in this generation.
  • the achievable storage density depends on the focusing of the laser spot in the information plane.
  • the spot size scales with the laser wavelength ⁇ / NA.
  • NA is the numerical aperture of the objective lens used.
  • the use of the smallest possible wavelength ⁇ is desirable. 390 nm are currently possible based on semiconductor laser diodes.
  • the write-once format is preferably HD-DVD-R and BD-R.
  • the wavelength lies at the foot of the long-wavelength edge of the absorption peak of the dye for a high reflectivity and a high modulation depth of the read-out signal, as well as for sufficient sensitivity during writing.
  • the writable information layer of light-absorbing organic substances should have as amorphous 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 interfaces and thus 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.
  • optical data carriers with light-absorbing compounds from the group of special axially substituted phthalocyanine sulfonamides can meet the above-mentioned requirement profile particularly well.
  • the invention relates to optical data carriers containing a preferably transparent, optionally already coated with one or more reflective layers and / or protective 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 can be described and read with blue light of a wavelength in the range of 360- 460 nm, in particular 390 to 420 nm, most preferably from 400 to 410 nm, preferably laser light, wherein the information layer is a light-absorbing compound and optionally a binder contains characterized in that at least one axially substituted phthalocyanine sulfonamide of the formula I is used as the light-absorbing compound,
  • R 1 and R 2 independently of one another are hydrogen, alkyl, cycloalkyl, alkenyl, aralkyl, aryl or hetaryl or R 1 and R 2 together with the N atom to which they are attached are hydrogenated, partially hydrogenated, quasi-aromatic or aromatic Form a ring, preferably form a 5- to 7-membered ring which optionally contains further heteroatoms, in particular from the group N, O and / or S,
  • R 3 is hydrogen, alkyl, cycloalkyl, alkenyl, aralkyl, aryl or hetaryl,
  • Tetrabutylammonium cation Tetrabutylammonium cation, tetrapropylammonium cation, tetraethylammonium cation, tetramethylammonium cation.
  • alkyl optionally substituted Ci- Ci 6 alkyl, in particular Ci-Ci 2 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, iso-butyl, tert Butyl, n-pentyl, n-hexyl, 2-ethylhexyl, 2,4-dimethyl-3-pentyl, 2,2-dimethylbutyl, trifluoromethyl, perfluorinated ethyl, 2,2-trifluoroethyl, 3,3 mean 3-trifluoroethyl, perfluorobutyl, cyanoethyl, methoxyethyl, Methoxyethoxypropyl, chloroethyl.
  • alkenyl for example, AHyI or 2-buten-1-yl is suitable.
  • Preferred heterocyclic radicals or hetaryl radicals are pyridyl, thiazolyl or benzthiazolyl.
  • n + n is a number from 2.8 to 4, preferably 3.3 to 4,
  • embodiment Ia hereinafter referred to as embodiment Ia.
  • radical M in the formula I to Ia is
  • R.3 is a radical of the formula
  • M is Al, Ga, In, Si, Ge, Sn and A, Kat, R 1 and R 2 have the meanings given above, wherein the multiple occurring radicals each have independent meanings, hereinafter referred to as Embodiment II.
  • A stands for oxygen
  • M stands for Al or Si
  • R ⁇ is hydrogen, hydroxy, halogen, alkyl, cycloalkyl, alkoxy, mono- or dialkylamino, aralkyl, aryl, hetaryl, arylazo, hetarylazo, cyano, nitro or alkoxycarbonyl and
  • A stands for oxygen
  • M stands for Al or Si
  • R 1 to R 2 represent methyl, ethyl, propyl, i-propyl, butyl, i-butyl, t-butyl, methoxyethoxypropyl,
  • R 5 is hydrogen, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl,
  • Embodiment IV has the meaning given above, hereinafter referred to as Embodiment IV.
  • Another object of the invention are phthalocyanine sulfonamides of the formula I in the embodiment II as such, preferably those of the embodiment III, in particular of the embodiment IV.
  • the invention further relates to a process for the preparation of the axially substituted phthalocyanine sulfonamides according to the invention, which is characterized in that a phthalocyanine is sulfochlorinated, then reacted with an amine of the formula HNR R and then with a phenol or thiophenol of the formula
  • the sulfonation of the process according to the invention is generally carried out in chlorosulfonic acid optionally with the addition of thionyl chloride, at 5O-16O ° C, preferably at 100-150 0 C.
  • the sulfochloride is isolated and optionally with the amine Water and reacted with addition of alkali at 20-80 0 C.
  • the invention further relates to solutions containing
  • Preferred solutions are at least 1 percent by weight, preferably at least 2 percent by weight, more preferably at least 5 percent by weight, of the phthalocyanine sulfonamides according to the invention.
  • the solvent used is preferably 2,2,3,3-tetrafluoropropanol, octafluoropropanol, propanol, butanol, pentanol, hexanol, diacetone alcohol, dibutyl ether, heptanone or mixtures thereof.
  • Particularly preferred is 2,2,3,3-tetrafluoropropanol.
  • octafluoropropanol Particular preference is given to 2,2,3,3-tetrafluoropropanol / diacetone alcohol in a mixing ratio of 90:10 to 98: 2.
  • the information is written by thermal modification of the light-absorbing compound.
  • the thermal change is carried out at a temperature ⁇ 600 ° C, more preferably at a temperature ⁇ 400 ° C, most preferably at a temperature ⁇ 300 ° C, but at least greater than 200 ° C.
  • Such a change may be, for example, a decomposition or chemical change of the chromophore center of the light-absorbing compound.
  • This change can be a decomposition.
  • This change may be a cleavage of substituent moieties.
  • This thermal decomposition may be accompanied by blistering and / or deformation of the adjacent layers (e.g., reflective layer, protective layer, dielectric layer) and / or deformation of the substrate.
  • the invention further relates to a method for describing the optical data storage according to the invention, which is characterized in that the data carrier with blue light having a wavelength in the range of 360- 460 nm, in particular 390 to 420 nm, very particularly preferably from 400 to 410 nm, preferably laser light , is described.
  • the preferably used laser optics preferably has a numerical aperture NA> 0.6, particularly preferably> 0.65. Most preferably, a numerical aperture NA> 0.7. Also very particularly preferred is a numerical aperture NA > 0.8.
  • the choice of the numerical aperture depends on the structure of the data carrier, in particular on the thickness of the irradiated substrate or the irradiated cover layer (see below). The thinner the irradiated layer, the larger NA can be.
  • Describing and reading the optical data carrier preferably takes place at the same wavelength.
  • the k value (imaginary part of the complex refractive index) of the information layer is preferably in the range of 0.01 to 0.40, preferably in the range of 0.01 to 0.30, particularly preferably in the range of 0.01 to 0.20.
  • the invention further relates to the use of the phthalocyanine sulfonamides according to the invention as light-absorbing compounds in the information layer of write-once optical data carriers, which can be described and read with blue light, with a wavelength in the range of 360-460 nm, in particular laser light.
  • the Phthalocyaninsulfonamide used according to the invention have a sufficiently high reflectivity (preferably> 10%, in particular> 20%) of the optical disk in the unwritten state and a sufficiently high absorption for thermal degradation of the information layer at point illumination with focused light when the wavelength of light in the field from 360 to 460 nm.
  • 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 phthalocyanine sulfonamides of the formula I are preferably applied to the optical data carrier from solution, preferably by spin coating.
  • the spin-coating is preferably carried out from solution or dispersion.
  • the phthalocyanines of formula I can be mixed with each other or with other dyes having similar spectral properties.
  • Information layer may contain, in addition to the phthalocyanines, additives such as binders,
  • wetting agents, stabilizers, thinners and sensitizers and other ingredients are preferably used.
  • Silicon dioxide and silicon nitride are applied, for example, by so-called reactive sputtering.
  • the layer thicknesses are for example in the range of 1 nm to 40 nm.
  • the metal layers are applied by sputtering, for example.
  • the layer thicknesses are for example in the range of 10 to 180 nm.
  • the structure of the optical data carrier can be:
  • a preferably transparent substrate (1) on whose surface at least one information layer (3) writable with light, which can be described with light, preferably laser light, optionally a protective layer or dielectric layer (4), optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • a preferably transparent substrate (1) on the surface of which a reflection layer (7), at least one information layer (3) writable with light, which can be described with light, preferably laser light, optionally a protective layer or dielectric layer (4), optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • a preferably transparent substrate (1) on whose surface a protective layer or dielectric layer (2), a reflection layer (7), at least one light, preferably laser light writable information layer (3), optionally a protective layer or dielectric layer (4) , optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
  • a preferably transparent substrate (1) on whose surface optionally a protective layer or dielectric layer (2), at least one light, preferably laser light writable information layer (3), optionally a protective layer or dielectric layer (4), optionally an adhesive layer ( 5), and a transparent cover layer (6) are applied.
  • protective layers or dielectric layers can also be provided between substrate (11) and information layer (12) and / or between information layer (12) and reflection layer (13) and / or between reflection layer (13) and adhesive layer (14). 16).
  • such a protective layer or dielectric layer (16) is located between substrate (11) and information layer (12).
  • the optical data carrier preferably contains an information layer (3) or (12).
  • the optical data carrier contains a reflection layer (7) or (13).
  • the optical data carrier contains a substrate (1) or (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 (1) having on its surface a reflection layer (7), an information layer (3) which can be written on and read with light, preferably laser light, a protective layer or dielectric layer (4), an adhesive layer (5), and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is as follows: a transparent substrate (1) on the surface of which a reflection layer (7), an information layer (3) describable and readable by light, preferably laser light, a protective layer or dielectric layer (4), and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is as follows:
  • the structure of the optical data carrier is as follows:
  • a transparent substrate (1) having on its surface a reflection layer (7), a protective layer or dielectric layer (2), an information layer (3) which can be written on and read with light, preferably laser light, a protective layer or dielectric layer (4)
  • Adhesive layer (5), and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is as follows:
  • the structure of the optical data carrier is as follows:
  • the structure of the optical data carrier is as follows:
  • a transparent substrate (1) having on its surface a protective layer or dielectric layer (2), an information layer (3) to be written on and read by light, preferably laser light, a protective layer or dielectric layer (4), an adhesive layer (5), and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is as follows:
  • a transparent substrate (1) on the surface of which a protective layer or dielectric layer (2), an information layer (3) which can be written on and read with light, preferably laser light, is generated Protective layer or dielectric layer (4), and a transparent cover layer (6) are applied.
  • the structure of the optical data carrier is as follows:
  • a transparent substrate (1) on the surface of which a protective layer or dielectric layer (2), an information layer (3) which can be written on and read with light, preferably laser light, and a transparent cover layer (6) are applied.
  • 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
  • another transparent substrate 15
  • a transparent substrate 11
  • a protective layer or dielectric layer 16
  • an information layer (12) which can be written on and read with light, preferably laser light
  • a reflection layer 13
  • an adhesive layer 14
  • another transparent substrate 15
  • the structure of the optical data carrier is as follows:
  • a transparent substrate 11
  • a protective layer or dielectric layer 16
  • an information layer (12) which can be written on and read with light, preferably laser light a protective layer or dielectric layer (16)
  • a reflective layer 13
  • an adhesive layer 14
  • another transparent substrate 15
  • 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 protective layer or dielectric layer (16)
  • a reflection layer 13
  • an adhesive layer 14
  • a further transparent substrate (15)
  • optical data carriers which contain two information layers. They can be structured, for example, as follows:
  • optionally a protective layer or dielectric layer (4) an information layer (3), optionally a protective layer or dielectric layer (2), optionally a reflective layer (7), a transparent substrate (1), optionally a reflective layer (7), optionally a protective layer or dielectric layer (2), an information layer (3), optionally a protective layer or dielectric Layer (4), optionally an adhesive layer (5), a cover layer (6).
  • optical data carriers with two information layers can also contain all the preferred layer structures listed above in an analogous manner.
  • Optical data carriers with more than two information layers can be constructed in an analogous manner.
  • the invention further relates to optical media according to the invention described with blue light, in particular laser light, preferably the wavelength described above.
  • the invention further relates to a process for the preparation of the optical data carrier according to the invention, which comprises using a preferably transparent, optionally coated with a reflective layer substrate with at least one Phthalocyaninsulfonamid the formula as a light-absorbing compound, optionally in combination with suitable binders and additives and optionally coated with solvents and optionally with a reflective layer, further intermediate layers and optionally provides a protective layer or another substrate or a cover layer.
  • a 1.5% strength by weight solution of the dye from Example 10 in 2,2,3,3-tetrafluoropropanol was prepared. 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 sputtered with 100 nm of silver.
  • a UV-curable acrylic paint was applied by spin coating and glued before curing with a UV lamp, a dummy disk.
  • the light reflected by the reflection layer of the disc was coupled out of the beam path by means of the above-mentioned polarization-sensitive beam splitter and focused on an quadrature detector by an astigmatic lens.
  • a linear velocity V 6.5 ms
  • the disk was irradiated with this oscillating pulse sequence until it had once turned around itself. Thereafter, the mark thus generated was read out with the reading power P rea d, and the above-mentioned signal-to-noise ratio C / N was measured.
  • optical parameters of this dye of the prior art are thus significantly worse than those of the other erfindungsgenä on examples.

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

Abstract

L'invention concerne des supports de données optiques comprenant un substrat, de préférence, transparent, éventuellement déjà revêtu d'au moins une couche réflectrice et/ou couche de protection. Une couche d'informations inscriptible à la lumière, éventuellement au moins une couche réflectrice et éventuellement une couche protectrice ou un autre substrat ou une couche de recouvrement sont appliquées sur la surface du substrat susmentionné. Ce substrat peut être écrit ou lu par une lumière bleue d'une longueur d'onde de la plage 360-460 nm, notamment 390 à 420 nm, idéalement de 400 à 410 nm, de préférence la lumière laser. La couche d'informations contient un composé absorbant la lumière et éventuellement un liant. L'invention est caractérisée en ce que l'on utilise comme composé absorbant la lumière au moins un phthalocyaninsulfonamide axialement substitué de la formule (I) où M représente un atome de métal trivalent ou tétravalent ; R1 et R2 représentent indépendamment hydrogène, alkyle, cycloalkyle, alcényle, aralkyle, aryle ou hétaryle ou R1 et R2 forment avec l'atome N auquel ils sont liés, un cycle quasi aromatique ou aromatique hydrogéné, partiellement hydrogéné, de préférence un cycle à 5 à 7 chaînons contenant éventuellement d'autres hétéroatomes, notamment issus du groupe N, O et/ou S ; R3 représente hydrogène, alkyle, cycloalkyle, alcényle, aralkyle, aryle ou hétaryle ; R4 représente hydroxy, halogène, alkyle, cycloalkyle, alcoxy, monoamino ou dialkylamino, aralkyle, aryle, hétaryle, arylazo, hétarylazo, cyano, nitro ou alcoxycarbonyle ; A représente un oxygène ou soufre et m vaut un nombre de 1 à 4, n vaut un nombre de 0 à 3, m+n valent un nombre de 1 à 4 et, x vaut 1 pour un atome métallique trivalent, vaut 2 pour un atome métallique tétravalent et y vaut un nombre de 0 à 4 et Kat représente un hydrogène, cation de lithium, cation de sodium, cation de potassium, cation d'ammonium, cation de tétrabutylammonium, cation de tétrapropylammonium, cation de tétraéthylammonium, action de tétraméthylammonium.
PCT/EP2006/006183 2005-07-08 2006-06-27 Phthalocyaninsulfonamides axialement substitues utilises comme composes absorbant la lumiere dans la couche d'informations de supports de donnees optiques WO2007006417A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510031974 DE102005031974A1 (de) 2005-07-08 2005-07-08 Axial substituierte Phthalocyaninsulfonamide als lichtabsorbierende Verbindungen in der Informationsschicht von optischen Datenträgern
DE102005031974.2 2005-07-08

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WO2007006417A2 true WO2007006417A2 (fr) 2007-01-18
WO2007006417A3 WO2007006417A3 (fr) 2007-04-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016517398A (ja) * 2013-03-11 2016-06-16 サウジ ベイシック インダストリーズ コーポレイション Ｉｉｉ族金属のアリールオキシ−フタロシアニン

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105051049A (zh) 2013-03-11 2015-11-11 沙特基础工业公司 用在太阳能电池中的第iv族金属的芳氧基酞菁

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0371888A (ja) * 1989-08-11 1991-03-27 Toyobo Co Ltd 光学記録媒体
DE10148106A1 (de) * 2001-09-28 2003-04-17 Bayer Ag Optische Datenspeicher enthaltend ein axial substituiertes Co-Phthalocyanin in der mit Licht beschreibbaren Informationsschicht
US20030113665A1 (en) * 2001-03-28 2003-06-19 Horst Berneth Optical data medium containing, in the information layer, a dye as a light-absorbing compound
WO2005000972A2 (fr) * 2003-06-27 2005-01-06 Ciba Specialty Chemicals Holding Inc. Materiels d'enregistrement optique presentant une forte densite de stockage

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0371888A (ja) * 1989-08-11 1991-03-27 Toyobo Co Ltd 光学記録媒体
US20030113665A1 (en) * 2001-03-28 2003-06-19 Horst Berneth Optical data medium containing, in the information layer, a dye as a light-absorbing compound
DE10148106A1 (de) * 2001-09-28 2003-04-17 Bayer Ag Optische Datenspeicher enthaltend ein axial substituiertes Co-Phthalocyanin in der mit Licht beschreibbaren Informationsschicht
WO2005000972A2 (fr) * 2003-06-27 2005-01-06 Ciba Specialty Chemicals Holding Inc. Materiels d'enregistrement optique presentant une forte densite de stockage

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016517398A (ja) * 2013-03-11 2016-06-16 サウジ ベイシック インダストリーズ コーポレイション Ｉｉｉ族金属のアリールオキシ−フタロシアニン

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