WO2004086390A1 - Optischer datenträger mit polymerem netzwerk in der informationsschicht - Google Patents
Optischer datenträger mit polymerem netzwerk in der informationsschicht Download PDFInfo
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- WO2004086390A1 WO2004086390A1 PCT/EP2004/002585 EP2004002585W WO2004086390A1 WO 2004086390 A1 WO2004086390 A1 WO 2004086390A1 EP 2004002585 W EP2004002585 W EP 2004002585W WO 2004086390 A1 WO2004086390 A1 WO 2004086390A1
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- 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
- G11B7/245—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 a polymeric component
Definitions
- the invention relates to optical data storage media with a polymeric network based on organic dyes in the information layer, process for its production, its use and layered polymeric networks, its production and use.
- DE-A-10115227 already describes writable optical data carriers which contain light-absorbing compounds with at least two chromophoric centers in their information layer.
- Appropriate homopolymers, copolymers or graft polymers and dendrimers are suitable as such.
- the polymeric dyes from DE-A-10115227 are too deformable. Furthermore, it is not possible to use these polymeric dyes, as well as other dyes, to build up several information layers by means of several successive spin coat cycles, since the dye of the layer applied first would dissolve again when using, for example, identical solvents during spin coating of the subsequent layer , This causes uneven layer thicknesses and a particularly undesirable mixing of the dyes of the different layers if the individual layers are to be made up of different dyes.
- Films made from organic dyes or polymer dyes generally have mechanical surface hardness and scratch resistance that are often not sufficient to do without a protective lacquer layer. For this reason, information layers based on organic dyes or polymer dyes are not or only to a limited extent suitable for optical data storage devices which use the principle of "first surface recording / reading".
- the information is written or read directly to or directly under the surface of the data carrier.
- the distance between the surface of the lens or the aperture opening for the read / write head and the data carrier surface is less than the light wavelength used in the vacuum (near-field optics). This can lead to frequent mechanical contact of the read / write head with the data carrier surface during operation. Information layers with low mechanical surface hardness and low scratch resistance are damaged and unusable.
- the invention therefore relates to optical data storage media with at least one information layer which contains a polymer network with covalently bound light-absorbable compounds.
- the data carriers according to the invention preferably have an information layer with a high mechanical surface hardness and a high scratch resistance and are therefore particularly suitable for "first surface recording / reading".
- the polymer network is preferably layered as an information layer or as part of the information layer on the data carrier.
- the information layer is preferably understood as a layer that can be written on and readable with light. Blue, red or infrared light, in particular laser light, is regarded as the preferred light.
- the wavelength ranges 380-450 .mu.m, in particular 390-420 nm for blue light, 630-680 nm, in particular 635-660 nm for red light and 750-830 nm, in particular 770-800 nm for infrared light are particularly preferred.
- One or more information layers can be applied to the optical data carrier.
- formats such as CD-R, DVD-R and BD-R, however, there is preferably one information layer per page on the data carrier.
- Femfield optics are preferably used to write and read the information layers on CD-R, DVD-R and BD-R.
- a near-field optical system is preferably implemented by z.
- each information layer on the optical disk is in use
- far field optics for writing and reading preferably 1 to nm
- ⁇ is the laser light wavelength in vacuum
- NA is the numerical aperture of the objective
- each information layer on the optical disk is in use
- near-field optics for writing and reading preferably 1 to ⁇ - - nm, in particular 10 to
- ⁇ is given in nm.
- the thickness of the information layer on the optical data carrier can therefore be determined since the surface of the carrier substrate of the information layer generally contains a pregroove in the form of a groove-shaped structure.
- the dyes, which form the later information layer after hardening, are applied by spin coating, therefore, not all areas of the data carrier surface will have the same thickness of the information layer.
- the polymer network preferably has an absorption maximum in the range from 340 to 820 nm.
- the polymeric network is based on at least one monomer which contains at least one light-absorbing group.
- Preferred monomers are those which have an absorption maximum ⁇ ma _ in the range from 340 to 410 nm or an absorption maximum ⁇ ma ⁇ in the range from 400 to 650 nm or an absorption maximum ⁇ ma r f in the range from 630 to 820 nm, the wavelength ⁇ m, where the extinction in the long-wave flank of the absorption maximum of wavelength ⁇ m ai, ⁇ m a ⁇ or ⁇ max3 or the extinction in the short-wave flank of the absorption maximum of wavelength ⁇ ma ⁇ or ⁇ max3 half of the extinction value at ⁇ ma _ ⁇ , ⁇ max2 or X ⁇ , and the wavelength ⁇ / ⁇ 0 , at which the extinction in the long-wave flank of the absorption maximum of the wavelength ⁇ ma _ ⁇ , ⁇ ⁇ , a _ 2 or ⁇ ma _ .
- the extinction in the short-wave flank of the absorption maximum of wavelength ⁇ max2 or ⁇ maö is one tenth of the extinction value at ⁇ max i, ⁇ max2 or ⁇ max3 , preferably not more than 80 nm apart.
- the light-absorbing groups of the monomers should preferably be thermally changeable.
- the thermal change preferably takes place at a temperature ⁇ 600 ° C., particularly preferably at a temperature ⁇ 400 ° C., very particularly preferably at a temperature ⁇ 300 ° C., in particular ⁇ 200 ° C.
- Such a change can be, for example, a decomposition or chemical change in the chromophoric center of the monomer.
- the absorption maximum ⁇ maxl of the monomer is in the range 340 to 410 nm, preferably 345 to 400 nm, in particular 350 to 380 nm, particularly preferably 360 to 370 nm, the wavelength X at which the absorbance in the long-wave Flank of the absorption maximum of the wavelength ⁇ max ⁇ is half the extinction value at ⁇ max ⁇ , and the wavelength ⁇ 10 , at which the extinction in the long-wave flank of the absorption maximum of the wavelength ⁇ maxl is one tenth of the extinction value at ⁇ maxl than 50 nm apart.
- a wavelength up to a wavelength of 500 nm, particularly preferably 550 nm, very particularly preferably 600 nm does not have a longer-wave maximum ⁇ max2 .
- ⁇ / _ and Xmo are preferably not more than 40 nm apart, more preferably not more than 30 nm apart, very particularly preferably not more than 10 nm apart.
- the absorption maximum ⁇ ma __ of the monomer is in the range 420 to 550 nm, preferably 410 to 510 nm, in particular 420 to 510 nm, particularly preferably 430 to 500 nm, the wavelength ⁇ 1Q at which the Absorbance in the short-wave flank of the absorption maximum of the wavelength ⁇ max2 is half the extinction value at ⁇ max2 , and the wavelength X o, at which the extinction in the short-wave flank of the absorption maximum of the wavelength ⁇ ma ⁇ is one tenth of the extinction value at ⁇ ma _ 2 should not be more than 50 nm apart.
- Such a light-absorbing compound preferably has no shorter-wave maximum ⁇ maxi up to a wavelength of 350 nm, particularly preferably 320 nm, very particularly preferably 290 nm.
- ⁇ 2 and ⁇ 1 10 are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.
- the absorption maximum ⁇ raax2 of the monomer is in the range 500 to 650 nm, preferably 530 to 630 nm, in particular 550 to 620 nm, particularly preferably 580 to 610 nm, the wavelength X ⁇ 2 at which the extinction in the long-wave flank of the absorption maximum of wavelength ⁇ max2 is half the extinction value at ⁇ ma ⁇ _, and the wavelength Xmo, at which the extinction in the long-wave flank of the absorption maximum of wavelength ⁇ max2 is one-tenth of the extinction value at ⁇ max a must not be more than 50 nm apart.
- points such a connection does not have a longer-wavelength maximum ⁇ max3 up to a wavelength of 750 nm, particularly preferably 800 nm, very particularly preferably 850 nm.
- These monomers X ⁇ 2 and Xmo, as defined above, are preferably not more than 40 nm apart, more preferably not more than 30 nm apart, very particularly preferably not more than 10 nm apart.
- the absorption maximum ⁇ max3 of the monomer is in the range 630 to 800 nm, preferably 650 to 770 nm, in particular 670 to 750 nm, particularly preferably 680 to 720 nm, the wavelength ⁇ 1/2 at which the Absorbance in the short-wave flank of the absorption maximum of wavelength ⁇ maX3 at half the absorbance value is, and the wavelength ⁇ / ⁇ 0 , at which the extinction in the short-wave flank of the absorption maximum of wavelength ⁇ maö is one-tenth of the extinction value at ⁇ max3 , must not be more than 50 nm apart.
- Such a connection preferably does not have a shorter-wave maximum ⁇ max2 up to a wavelength of 600 nm, particularly preferably 550 nm, very particularly preferably 500 nm.
- This monomer Xm and Xmo are preferably not more than 40 nm apart, particularly preferably not more than 30 nm, very particularly preferably not more than 20 nm apart.
- the absorption maximum ⁇ max3 of the monomer is in the range from 650 to 810 nm, preferably 660 to 790 nm, in particular 670 to 760 nm, particularly preferably 680 to 740 nm, the wavelength ⁇ 1/2 at which the extinction in the long-wave flank of the absorption maximum of wavelength ⁇ max3 is half the extinction value at A TM ⁇ , and the wavelength Xmo, at which the extinction in the long-wave flank of the absorption maximum of wavelength ⁇ max3 is one tenth of the extinction value at ⁇ max3 , are preferably no more than 50 nm apart.
- These monomers Xm and Xmo, as defined above, are preferably not more than 40 nm apart, more preferably not more than 30 nm apart, very particularly preferably not more than 0 nm apart.
- the monomers preferably have a molar extinction coefficient ⁇ > 10,000 1 / mol cm, preferably> 15,000 1 / mol cm, particularly preferably> 20,000 1 / mol cm, very particularly preferably> 25,000 l / mol cm, in particular> 30,000 l / mol cm, preferably> 40,000 l / mol cm.
- ⁇ value which is a parameter typical of a solution, the same physical properties also apply to the polymer network.
- Possible polymer networks are those which are produced by polymerization, polycondensation or by polyaddition reactions
- Polymeric networks are preferably those based on
- Polyfunctional here means bearing several groups, which are available as reactive centers for the corresponding reaction, i.e. polymerization, polycondensation or polyaddition. Accordingly, such a group is now present in monofunctional monomers.
- these are preferably C-C double bonds which are capable of polymerization and special heterocyclic structures such as ethers, thioethers, esters and acetals, in particular free-radical and cationically polymerizable C-C double bonds or oxirane rings.
- components other than A) and B) can also be used to produce the polymeric networks.
- more than 90% by weight, preferably more than 95% by weight, in particular more than 98% by weight, of the reactants are those of components A) and optionally B).
- A) preferably bifunctional or higher functional monomers are used.
- Component A) is preferred for the polyaddition or polycondensation
- AI at least one bifunctional
- A2) at least one tri- or higher functional monomer is used.
- Monomers are of course also understood to mean functional prepolymers which can be used for the polymerization in the sense of the application.
- Preferred polyfunctional monomers of component A) are those of the formula (II)
- F stands for a chromophoric center, where all f chromophoric centers can be different;
- K stands for a polymerizable group, where all k polymerizable groups can be different
- B stands for a bivalent bridge, whereby all b bridges can be different
- k is the integer that stands for values from 2 to 1000
- b, f stand for the integers, which can independently take values from 1 to 1000.
- a mixture of component A) and B) is preferred for the polymerization, with up to 90% by weight of the mixture of A) and B) corresponding to component B).
- B 1 and B 2 represent the bivalent bridges
- n an integer from 1 to 8
- n an integer 3 or 4.
- Polymeric monomers are also particularly preferred, in particular those which correspond to formulas VII to VIII:
- P - stands for a repeating unit of the polymeric backbone, with particular preference being given to those whose backbone has resulted from the polymerization from groups K,
- p (0) stands for the average degree of polymerization customary for the polymers, which can assume the values from 3 to 1000. These values are very particularly preferably from 3 to 100,
- K 1 represents a polymerizable group which cannot be the same as the polymerizable group K
- Chromophore-containing copolymers with the polymerizable groups in the side chains are also particularly preferred.
- P 1 and P 2 - stand for the same or different repeating units of the polymer backbone, with particular preference being given to those which form the backbone of the polymer from the same or different groups K,
- B 4 and B 5 have the same meaning as B 1 and B 2
- p (l) and p (2) are the corresponding degrees of polymerization, which in total correspond to an average degree of polymerization p (0) customary for the polymers, which can assume the values between 3 and 1000.
- Particularly preferred monomers for the production of the information layers are those of the formulas (III) to (XI)
- B 1 , B 2 . B 4 . B 5 stands for -Q'-T ⁇ Q 2 -,
- Q 1 to Q 4 each independently represent a direct bond or -O-, -S-,
- T 1 is a direct bond or is - (CH 2 ) P - or o-, m- or p-phenylene, the chain - (CH 2 ) P - by -O-, -NR 1 - or -OSiR 5 2 O- can be interrupted or for a 1,2-, 1,3- or 1,4-cyclohexane ring in all possible isomer
- the cyclohexane ring can carry up to 3 methyl substituents
- q, r, s and t independently represent an integer from 0 to 12,
- u represents an integer from 2 to 4,
- R 2 to R 4 and R 6 independently of one another are hydrogen, Ci-C ⁇ -alkyl, C 3 -C ⁇ 0 cycloalkyl, C 2 - C 12 alkenyl, C 6 -C ⁇ 0 aryl,
- R 5 represents methyl or ethyl
- K and K 1 independently of one another represent a polymerizable group.
- Acryloyloxy-, methacryloyloxy, 2-chloro- and 2-bromoacryloyloxy, o-, m- and p-styryl-, acryloylamide- and methacryloylamide-, N-alkyl-acryloylamide- and N-alkyl-meth-acryloylamide, vinyl are preferred -oxy and vinyloxycarbonyl, oxiranyl-, 2- and 3-oxetanyl-, 2 and 3-tetrahydrofuranyl, vinylphosphonyl- and vinylsulfonyl, 2-, 3-, 4-vinylpyridinium and N-vinyl imidazolium groups.
- Acryloyloxy, methacryloyloxy, vinyloxy and oxiranyl groups are particularly preferred.
- Preferred functionalized polymers and copolymers of the formula (VII) - (XI) are those whose polymer chain is based on the same or different structural elements P, P 1 and P 2 and
- P, P 1 and P 2 independently of one another for a structural element of a polyacrylate, methacrylate, acrylamide, methacrylamide, siloxane, oxirane, ether, amide, urethane, urea, ester, carbonate , Styrene or maleic acid derivative.
- Polyacrylates, methacrylates, vinyl ethers and esters and poly (- ⁇ -oxiranes) are preferred. Also preferred are copolymers containing acrylate or methacrylate and acrylamide units. Polyacrylates and methacrylates are particularly preferred. In these cases, P, P 1 and P 2 are independently
- R represents hydrogen or methyl
- the chromophoric centers of the monomers with light-absorbing groups can, for example, be residues of the following structure types (see, for example, G. Ebner and D. Schulz, Textile Dyeing and Dyes, Springer-Verlag, Berlin Heidelberg, 1989; H. Zollinger, Color Chemistry, VCH Verlagsge- Seilschaft mbH Weinheim, 1991):
- Azo dyes anthraquinone dyes, indigoid dyes, polymethine dyes, aryl carbonium dyes, nitro dyes, perylenes, coumarins, formazans, optionally bridged (hetero) -cinnamic acid derivatives, (hetero) stilbenes, methines, cyanines, hemicyanines, neutromethines (null) methanes (methocyanines) , Hydrazones, azine dyes, triphendioxazines, pyronines, acridines, rhodamines, indamines, indophenols, di- or triphenylmethanes, aryl and hetaryl azo dyes, quinoid dyes, phthalocyanines, naphthocyanines, subphthalocyanines, porphyrins, tetraazaporphyrins and metal complexes.
- Preferred light-absorbing compounds with an absorption maximum ⁇ max ⁇ in the range 340 to 410 nm are, for example, those of the following formulas.
- Corresponding optical data storage devices with these polymeric networks based on corresponding monomers with light-absorbing groups based on compounds in the information layer can be read and written with blue or red light, in particular laser light:
- Ar and Ar independently of one another are C 6 -C 1 -aryl or the residue of a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals,
- Y and Y independently of one another represent N or C-R or ⁇ l01 __.
- ⁇ l02 can stand for a direct bond
- R and R independently of one another represent hydrogen, Ci- ⁇ -alkyl, cyano, carboxylic acid, -C 16 -C alkoxycarbonyl, C I -C 6 alkanoyl or Ar 102 or R 101 stands for a bridge to Ar 101 ,
- R and R independently of one another are cyano, nitro, carboxylic acid, Ci-Ci ⁇ -alkoxycarbonyl, aminocarbonyl or -Ci 6 alkanoyl or R 102 is hydrogen, halogen, C 1 -C 16 -alkyl or a radical of the formula
- R 103 is Ar 102 , CH 2 -COOalkyl or P (0) (0-C 1 -C 12 -alkyl) 2 or CC 16 -alkyl or R 102 ; R 103 together with the carbon atom connecting them represent a five- or six-membered carbocyclic or aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which may be benzylated or naphthanellated and / or substituted by nonionic radicals, or R 103 is a bridge to Ar 101 or forms ring A 101 , which may contain a heteroatom and / or may be substituted by nonionic radicals,
- R 100 represents hydrogen, C, -C 16 alkyl, C 7 -C 16 aralkyl or R 101 or
- NR 100 R 100 represents pyrrolidino, piperidino or morpholino or
- R 100 and R 104 together represent a -CH 2 -CH 2 - or -CH 2 -CH 2 -CH 2 - bridge,
- X 101 , X 102 , X 103 , X 104 , X 106 , X 109 and X 110 independently of one another represent O, S, or NR 100 or X 102 , X 104 or X 106 additionally represent CH or CR 100 R 100 ,
- a 101 , B 101 , C 101 , F 101 , G 101 and H 101 independently of one another represent a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals,
- X 105 and X 108 independently of one another represent N,
- E 102 stands for a direct bond
- -CH CH-
- Ar 103 and Ar 104 independently of one another represent 2-hydroxyphenyl radicals which can be benzanellated and / or substituted by hydroxy, C 1 -C 6 alkoxy or C6-C 10 aryloxy,
- R 108 for C r -C 6 alkyl, CHO, CN, CO-C 1 -C 8 alkyl, CO-C 6 -C ⁇ 0 aryl or CH C (CO-
- R 109 represents hydroxy or cis alkoxy
- R 112 represents hydrogen, C 6 -C 6 -alkyl or cyano
- R 113 is hydrogen, cyano, CC alkoxycarbonyl, C 6 -C 0 aryl, thien-2-yl, pyrid-2- or -4-yl, pyrazol-1-yl or 1,2,4-triazol-l - or -4-yl, which can be benzylated or naphthanellated and / or substituted by nonionic radicals,
- R 114 is hydrogen, C Ci 6 alkoxy, l, 2,3-triazol-2-yl, which may be substituted by nonionic radicals, C ⁇ -C ⁇ 6 alkanoylamino, C ⁇ -C 8 alkanesulphonylamino, or C 6 - CIO Arylsulfonylamino,
- Ar 105 and Ar 106 independently of one another are C 6 -C 1 -aryl or the residue of a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which is fused with benzene or naphthane and / or by nonionic radicals and / or by sulfo can be substituted,
- a, b and c independently of one another represent an integer from 0 to 2
- X 107 stands for N or rO-R 100 On " ,
- E 103 represents N, CH, C-CH 3 or C-CN
- R 115 and R 116 independently of one another represent hydrogen or -CC 16 alkyl
- R 117 and R 118 independently of one another are hydrogen, C 1 -C alkyl, cyano or C r 6 alkoxycarbonyl
- R 119 for hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or in each case 2 radicals R 119 one
- Thiophene ring represent a divalent radical of the formula -0-CH 2 -CH 2 -O-,
- Y 103 and Y 104 independently of one another represent O or N-CN
- R 120 to R 123 independently of one another for hydrogen, C 6 -C alkyl, C 6 alkoxy, cyano, Ci-Ci ⁇ -alkoxycarbonyl, halogen, Ar 101 , Ar 102 or
- R 125 and R 126 independently of one another are hydrogen, C 6 alkyl, CrC 6 alkoxy, cyano, C 6 alkoxycarbonyl, hydroxy, carboxylic acid or C 6 aryloxy,
- e, f and g independently represent an integer from 1 to 4, where if e, f or g> 1, the radicals can be different,
- X 111 represents N or C-Ar 102 .
- R 127 represents hydrogen, CC 16 alkyl or C 6 -C ⁇ 0 aryl
- R and R independently of one another are hydrogen, -Ci ö alkyl, C 6 -C ⁇ 0 aryl or C 7 -C ⁇ 5 - aralkyl or
- NR R stands for morpholino, piperidino or pyrrolidino
- R 130 represents CC 16 alkyl, C 7 -C 15 aralkyl or Ar 1 ,
- R 131 and R 132 independently of one another for hydrogen, -CC 6 alkyl, C 6 -C alkoxy, cyano, -C 16 alkoxycarbonyl, halogen or C 6 -C 10 aryl or together for a bridge of the formula -CO -N (R 130 ) -CO-, and
- Nonionic radicals are preferably -CC 4 alkyl, -C 4 -alkoxy. Halogen, cyano, nitro, QC 4 - alkoxycarbonyl, - alkylthio, C ⁇ -C 4 alkanoylamino, benzoylamino, mono- or D1 -C 4 - ylamino Al.
- Alkyl, alkoxy, aryl and heterocyclic radicals can optionally carry further radicals such as alkyl, halogen, nitro, cyano, CO-NH 2 , alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, the alkyl and alkoxy radicals can be straight-chain or branched, the Alkyl radicals can be partially or perhalogenated, the alkyl and alkoxy radicals can be ethoxylated or propoxy-hardened or silylated, adjacent alkyl and / or alkoxy radicals on aryl or heterocyclic radicals can together form a three- or four-membered bridge and the heterocyclic radicals can be fused to benzene and / or be quaternized.
- further radicals such as alkyl, halogen, nitro, cyano, CO-NH 2 , alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, the alkyl and
- Light-absorbing compounds of the formulas (CI) to (CXXI), (CHIa) and (CCCIX) are particularly preferred,
- Ar 101 and Ar 102 independently of one another for phenyl, naphthyl, benzthiazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, thiazol-2-yl, thiazolin-2-yl, pyrrolin-2-yl, isothiazol- 3-yl, imidazol-2-yl, l, 3,4-thiadiazol-2-yl, l, 3,4-triazol-2-yl, 2- or 4-pyridyl, 2- or 4-quinolyl, pyrrole- 2- or -3-yl, thiophene-2- or -3-yl, furan-2- or -3-yl,
- Y 101 and Y 102 independently of one another represent N or CR 101 or
- R 101 and R 104 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, cyano, carboxylic acid, methoxycarbonyl, ethoxycarbonyl, acetyl, propionyl or Ar 102 or Ar 101 and R 101 together represent a ring of the formula
- R 105 independently of one another are cyano, carboxylic acid, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, methoxyethoxycarbonyl, acetyl, propionyl or butanoyl or R 102 is hydrogen, or a radical of the formula
- R 103 stands for Ar 102 or R 105 stands for Ar 101 or R 102 ; R 103 or R 104 ; R 105 together with the connecting carbon atom for a ring of the formulas
- R 100 represents hydrogen, methyl, ethyl, propyl, butyl or benzyl or
- NR 100 R 100 stands for pyrrolidino, moprholino or piperidino or
- R 100 and R 104 together represent a -CH 2 -CH 2 bridge or
- R 100 in formula (CVII) or (CXIII) represent a -CH 2 -CH 2 - or -CH 2 -CH 2 -CH 2 bridge,
- a 101 , B 101 and G 101 independently of one another for benzothiazol-2-ylidene, benzoxazol-2-ylidene, benzimidazol-2-ylidene, thiazol-2-ylidene, thiazolin-2-ylidene, pyrrolin-2-ylidene, isothiazol-3 -ylidene, imidazol-2-ylidene, l, 3,4-thiadiazol-2-ylidene, l, 3,4-triazol-2-ylidene, pyridin-2- or 4-ylidene, quinolin-2- or 4-ylidene , Pyrrole-2- or -3-ylidene, thiophene-2- or -3-ylidene, furan-2- or -3-ylidene, indole-2- or -3-ylidene, benzothiophene-2-ylidene, benzofuran-2 -ylidene or 3,3-
- C 101 and F 101 independently of one another for benzthiazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, thiazol-2-yl, thiazolin-2-yl, pyrrolin-2-yl, isothiazol-3-yl, Imidazol-2-yl, l, 3,4-thiadiazol-2-yl, l, 3,4-triazol-2-yl, 2- or 4-pyridyl, 2- or 4-quinolyl, pyrrol-2- or - 3-yl, thiophene-2- or -3-yl, furan-2- or -3-yl, indole-2- or
- X 101 , X 102 , X 103 , X 104 , X 106 , X 109 and X 110 independently of one another represent O, S or NR 100 and X 102 , X 104 or X 106 additionally represent CH or CR 100 R 100 ,
- X 105 and X 108 independently of one another represent N,
- X 107 stands for N or N'-R 100 An "
- Ar 103 and Ar 104 independently of one another represent 2-hydroxyphenyl radicals which can be substituted by hydroxy, methoxy, ethoxy, propoxy, butoxy or phenoxy,
- R 108 represents methyl, ethyl, propyl, butyl, CHO, CN, acetyl, propionyl or benzoyl,
- R 109 represents hydroxy, methoxy, ethoxy, propoxy or butoxy
- R 112 represents hydrogen or methyl
- R 113 for hydrogen, cyano, methoxycarbonyl, ethoxycarbonyl, phenyl, thien-2-yl,
- R 114 for hydrogen, methoxy, ethoxy, propoxy, butoxy, l, 2,3-triazol-2-yl, which by
- Methyl and or phenyl may be substituted, acetylamino, methanesulfonylamino or benzenesulfonylamino is,
- Ar 105 and Ar 106 independently of one another for phenyl, benzthiazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, thiazol-2-yl, thiazolin-2-yl, pyrrolin-2-yl, isothiazol-3- yl, imidazol-2-yl, l, 3,4-triazol-2-yl, 2- or 4-pyridyl, 2- or 4-quinolyl, thiophene
- a, b and c independently of one another represent an integer from 0 to 1,
- E 103 represents N or C-CN
- R 115 and R 116 independently of one another represent hydrogen, methyl or ethyl
- R 117 and R 118 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, cyano, methoxycarbonyl or ethoxycarbonyl
- R 119 represents hydrogen, methyl, methoxy, ethoxy or in each case 2 radicals R 119 of a thiophene ring represent a bivalent radical of the formula -0-CH 2 CH 2 -0-,
- Y 103 and Y "104 independently of one another represent O or N-CN
- R to R independently of one another are hydrogen, methyl, ethyl, propyl, butyl, methoxy,
- R 124 for methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, cyano
- R 12S and R 126 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, cyano, methoxycarbonyl, ethoxycarbonyl or hydroxy, at least one of the radicals R 126 being in ring position 1 or 3 and methoxy Means ethoxy, propoxy or butoxy,
- e, f and g independently of one another represent an integer from 1 to 2, where if e, f or g> 1, the radicals can be different,
- X 111 represents N or C-Ar 102 .
- R 127 represents hydrogen, methyl, ethyl, propyl, butyl or phenyl
- R 128 and R 129 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, phenyl or benzyl or
- NR 128 R 129 represents morpholino, piperidino or pyrrolidino
- R 130 represents methyl, ethyl, propyl, butyl, methoxyethyl, ethoxyethyl, methoxypropyl, benzyl, phenethyl or Ar 1 ,
- R 131 and R 132 independently of one another for hydrogen, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, methoxycarbonyl, ethoxycarbonyl, chlorine or bromine or together for a bridge of the formula -CO-N (R 130 ) -CO - stand, M 3 " 00 stands for 2 H atoms, Al, Si, Ge, Zn, Mg or Ti IV , where M 300 in the case of Al, Si,
- Ge or Ti w also carries one or two further substituents or ligands R 313 and / or R 314 which are arranged axially relative to the phthalocyanine plane,
- R 306 to R 309 independently of one another represent methyl, ethyl, propyl, butyl, methoxy or chlorine,
- wbis z independently of one another represent an integer from 0 to 4,
- R 306 to R 309 , M 300 and w to z may additionally have the meaning defined below,
- the light-absorbing groups of the monomers used to produce the polymeric networks and thus also the light-absorbing groups of the polymeric network itself are derived from light-absorbing compounds.
- Preferred light absorbing compounds with an absorption maximum in the range from 400 to 650 nm are, for example, those of the following formulas:
- Corresponding optical data storage media with polymer networks based on corresponding monomers which contain light-absorbing groups which are derived from these compounds in the information layer can be used with Read and write blue or red light, especially blue or red laser light.
- Ar 201 , Ar 202 , Ar 204 Ar 205 and Ar 206 independently of one another are C 6 -C 1 -aryl or the residue of a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which is benzylated or naphthanellated and / or by nonionic Radicals or sulfo can be substituted,
- Ar: 03 represents the bifunctional radical of a C 6 -C ⁇ 0 aromatics or the bifunctional radical of a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals or sulfo, where two such bifunctional radicals can be connected via a bifunctional bridge, r201 stands for N or CR 201 ,
- R 201 represents hydrogen, C 1 -C 6 -alkyl, cyano, carboxylic acid, C C 6 -alkoxycarbonyl, - Ci ⁇ -alkanoyl or Ar 202 or a bridge to Ar 201 or R 200 ,
- R 202 and R 203 independently of one another represent cyano, carboxylic acid, Ci-Cig-alkoxycarbonyl, aminocarbonyl or CC 16 -alkanoyl or R 202 represents hydrogen, halogen or a radical of the formula
- R 203 is Ar 202 , CH 2 -COOalkyl or P (0) (0-CC 12 -alkyl) 2 or CC 16 -alkyl or R 202 ; R 203 together with the carbon atom connecting them represent a five- or six-membered carbocyclic or aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals,
- o 1 or 2
- R 204 stands for hydrogen, C r C 16 alkyl or C 7 -C 6 aralkyl or for a bridge to Ar 201 or Ar 202 or E 201 or Ar 205 or E 207 or
- NR 204 R 204 represents pyrrolidino, piperidino or morpholino
- X 201 , X 202 , X 204 and X 206 independently of one another represent O, S or NR 200 and X 202 , X 204 and X 206 additionally represent CH or CR 200 R 200 ,
- a 201 , B 201 , C 201 and J 201 independently of one another represent a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals,
- R 200 represents hydrogen, -CC 6 -alkyl or C 7 -C 6 -aralkyl or forms a ring to E 202 , E 203 , E 205 or E 206 ,
- R 206 represents hydrogen, cyano or CC 4 -alkyl-SO 2 -,
- R 207 for hydrogen. Cyano, Q-Gt alkoxycarbonyl or Ar 201 ,
- R represents NR R, piperidino, morpholino or pyrrolidino
- R 213 , R 218 , R 219 , R 222 and R 223 independently of one another are hydrogen, C 6 -C alkyl, C 7 -C 16 aralkyl or C 6 -C 0 aryl,
- X 207 represents O, S, NR 222 or C (CH 3 ) 2 ,
- Y 202 and Y 204 independently of one another stand for OR 222 , SR 222 or NR 222 R 223 ,
- Y 203 and Y 205 independently of one another represent O, S or N " V 22 R 223 An " ,
- R 209 and R 210 independently of one another for hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, oo oi /. * o _
- h and i independently of one another represent an integer from 0 to 3,
- R 211 represents hydrogen, C r C 4 alkyl or Ar 201 ,
- Y 210 and Y 211 independently of one another represent O, S or N-CN,
- X 208 and X 209 independently of one another represent O, S or NR 213 ,
- R 212 represents hydrogen, halogen, C 6 -C alkyl, C 7 -C 6 aralkyl or C 6 -C 0 aryl,
- D 201 , E 201 , G 201 and H 201 independently of one another represent a five- or six-membered aromatic or quasi-aromatic carbocyclic or an aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthane fused and / or substituted by nonionic radicals or sulfo .
- Y 206 and Y 207 independently of one another represent -O-, -NR 224 -, -CO-O-, -CO-NR 224 -, -S0 2 -0- or - S0 2 -NR 224 -,
- Y 208 , Y 209 and Y 210 independently of one another represent N or CH
- Y 21 represents O or -NR 224 .
- R 224 for hydrogen, -CC 6 -alkyl, cyano, C 1 -C 6 -alkoxycarbonyl, -C- 6 -alkanoyl,
- M 200 and M 201 independently of one another represent an at least divalent metal ion which can also carry further substituents and / or ligands, and M 201 can additionally represent two hydrogen atoms,
- F 201 represents a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which may contain further heteroatoms and / or may be benzylated or naphthanellated and / or may be substituted by nonionic radicals or sulfo,
- R 220 and R 221 independently of one another for hydrogen, -CC 6 -alkyl, CC 16 -alkoxy, cyano, C Ci 6 -alkoxycarbonyl, halogen, C 6 - cio-aryl, NR 222 R 223 or together for a bivalent radical formula
- X 210 represents N, CH, Ci-C ⁇ -alkyl, C-Ar 201 , C-Cl or CN (CC 6 -alkyl) 2 ,
- Nonionic radicals are preferably CC 4 -alkyl, C 4 alkoxy, halogen, cyano, nitro, -C 4 - alkoxycarbonyl, C ⁇ -C 4 alkylthio, C ⁇ -C 4 alkanoylamino, benzoylamino, mono- or di-C C 4 - alkylamino.
- Alkyl, alkoxy, aryl and heterocyclic radicals can optionally further radicals such as alkyl, halogen, nitro, cyano, COOH, CO-NH 2; Alkoxy, trialkylsilyl, trialkylsiloxy, phenyl or SO 3 H, the alkyl and alkoxy radicals can be straight-chain or branched, the alkyl radicals can be partially or perhalogenated, the alkyl and alkoxy radicals can be ethoxylated or propoxy-hardened or silylated, adjacent alkyl and / or alkoxy radicals on aryl or heterocyclic radicals can jointly form a three- or four-membered bridge and the heterocyclic radicals can be fused to benzine and / or quaternized.
- radicals such as alkyl, halogen, nitro, cyano, COOH, CO-NH 2; Alkoxy, trialkylsilyl, trialkylsiloxy, phenyl or SO
- Light-absorbing compounds of the formulas (Cd) to (CCXXVI) and (CCIVa) are particularly preferred,
- Ar 201 , Ar 202 , Ar 204 , Ar 205 and Ar 206 independently of one another for phenyl, naphthyl, benzthiazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, thiazol-2- or -5-yl, thiazoline -2-yl, pyrrolin-2-yl, isothiazol-3-yl, imidazol-2-yl, l, 3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2- or 4-pyridyl, 2- or 4-quinolyl, pyrrol-2- or -3-yl, thiophene-2- or -3-yl, furan-2- or -3-yl, ihdol-2- or -3-yl , Benzothiophene-2-yl, benzofuran-2-yl or 3,3-dimethylindolen-2-yl, which are
- 7-210 represents Cl, OH, NHR z ⁇ or R 2'0O0,
- Y ⁇ 201 stands for N or CR z ⁇ ,
- R 201 represents hydrogen, methyl, ethyl, propyl, butyl, cyano, carboxylic acid, methoxycarbonyl, ethoxycarbonyl, acetyl, propionyl or Ar 202 ,
- R 202 and R 203 independently of one another for cyano, carboxylic acid, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, methoxyethoxycarbonyl, acetyl,
- Propionyl or butanoyl or R 202 represents hydrogen or a radical of the formula
- R 203 represents Ar 202 or R 202 ; R 203 together with the connecting carbon atom for a ring of the formulas
- R 204 represents hydrogen, methyl, ethyl, propyl, butyl, benzyl or
- Ar 201 -NR 204 or Ar 205 -NR 204 stands for a pyrrole, indole or carbazole ring attached via N, which is formed by methyl, ethyl, methoxy, ethoxy, propoxy, chlorine, bromine, iodine, cyano, nitro or methoxycarbonyl can be substituted or
- NR 204 R 204 represents pyrrolidino, piperidino or morpholino
- benzthiazol-2-ylidene benzoxazol-2-ylidene, benzimidazol-2-ylidene, thiazol-2-ylidene, thiazol-5-ylidene, thiazolin-2-ylidene, pyrrolin-2-ylidene, isothiazol-3- ylidene, imidazol-2-ylidene, l, 3,4-thiadiazol-2-ylidene, l, 3,4-triazol-2-ylidene, pyridin-2- or 4-ylidene, quinolin-2- or 4-ylidene, Indol-3-yl or 3,3-dimethylindolen-2-ylidene, which are represented by methyl, ethyl, propyl, butyl, methoxy,
- X 201 , X 202 , X 204 and X 206 independently of one another represent O, S or NR 200 and X 202 , X 204 and X 206 additionally stand for CR 200 R 200 ,
- X 203 and X 205 independently of one another represent N, and
- R 200 represents hydrogen, methyl, ethyl, propyl, butyl or benzyl
- R 200 represents methyl, ethyl, propyl, butyl or benzyl
- R 201 ' represents hydrogen, methyl or cyano or two radicals R 201' represents a -CH 2 -
- R 206 represents cyano or methyl-SO 2 -
- R 207 represents hydrogen, cyano, CC 4 alkoxycarbonyl or Ar 201 ,
- R 208 represents NR 222 R 223 , piperidino, morpholino or pyrrolidino, R 213 , R 218 , R 219 , R 222 and R 223 independently of one another represent hydrogen methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, phenethyl, phenylpropyl or phenyl, which are represented by methyl, ethyl, propyl, butyl, methoxy , Ethoxy, propoxy, butoxy, chlorine, bromine, iodine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, acetylamino, propionylamino, butanoylamino, benzoylamino, COOH or S0 3 H can be substituted,
- X 207 represents O, S or NR 222 ,
- Y 202 and Y 204 independently of one another represent NR 222 R 223 ,
- Y 203 and Y 205 independently of one another represent O or IT ⁇ R 223 An " ,
- a and b independently of one another represent an integer from 0 to 3,
- R 211 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl or phenyl, which can be substituted by 1 to 3 radicals from the group hydroxyl, methyl, methoxy, chlorine, bromine, COOH, methoxycarbonyl, ethoxycarbonyl or SO 3 H .
- Y 210 and Y 211 independently of one another represent O or N-CN
- X 208 and X 209 independently of one another represent O or NR 213 ,
- R 212 represents hydrogen or chlorine
- R 214 and R 215 independently of one another for hydrogen, methyl, ethyl, propyl, butyl, methoxy,
- d and e independently of one another represent an integer from 1 to 3,
- D 201 and E 201 independently of one another represent phenyl, naphthyl, pyrrole, indole, pyridine, quinoline, pyrazole or pyrimidine, which are represented by methyl, ethyl, propyl, butyl, methoxy, Ethoxy, propoxy, butoxy, chlorine, bromine, cyano, nitro, hydroxy, NR 222 R 223 , acetylamino, propionylamino or benzoylamino can be substituted,
- Y 206 and Y 207 independently of one another represent -O-, -NR 224 -, -CO-O- or-CO-NR 224 -,
- Y 210 represents N or CH
- R 224 represents hydrogen, methyl, formyl, acetyl, propionyl, methylsulfonyl or ethylsulfonyl,
- M 200 stands for Cu, Fe, Co, Ni, Mn or Zn,
- M 201 for 2 H atoms Cu 11 , Co 11 , Co m , Ni ⁇ , Zn, Mg, Cr, AI, Ca, Ba, In, Be, Cd, Pb, Ru, Be, Pd 11 , PtF, AI , Fe 11 , Fe ffl , Mn 11 , V, Ge, Sn, Ti or Si, with M 201 in the case of Co ra , Fe ⁇ , Fe, Al, In, Ge, Ti, Y N and Si still one or two more
- Y ZU6 stands for -O-
- R 20 represents hydrogen, methyl, ethyl, propyl, butyl, benzyl or
- Ar 201 -NR 204 or Ar 205 -NR 204 stands for a pyrrole, indole or carbazole ring attached via N, which is formed by methyl, ethyl, methoxy, ethoxy, propoxy, chlorine, bromine, iodine, cyano, nitro or methoxycarbonyl can be substituted
- R 220 and R 221 independently of one another for hydrogen, methoxy, ethoxy, propoxy, butoxy, cyano, methoxycarbonyl, chlorine, bromine, phenyl, dimethylamino, diethylamino, dipropylamino, dibutylamino, anilino or together for a bivalent radical of the formula
- X • 210 stands for N or CH
- ⁇ -212 stands for NR O N-Ar zul or CR 20 u 2 z ⁇ R.2 z 0 ⁇ 3 j resort,
- Y ⁇ 213 stands for NH-R z ⁇ ⁇ NH-Ar "20 u 1 l or CR 2 z 0 ⁇ 2 z ⁇ R2 z 0 ⁇ 3 An " ,
- the light-absorbing groups used to produce the polymeric networks and thus also the light-absorbing groups of the polymeric network itself are derived from light-absorbing compounds.
- Preferred light-absorbing compounds with an absorption maximum ⁇ max3 in the range 630 to 820 nm are those of the following formulas:
- Corresponding optical data memories with polymer networks based on corresponding monomers, which contain light-absorbing groups which are derived from these compounds, in the information layer can be read and written with red or infrared light, in particular red or infrared laser light.
- Ar 301 and Ar 302 independently of one another are C 6 -C 1 -aryl or the residue of a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals or sulfo,
- Ar 303 for the bifunctional radical of a C 6 -C ⁇ 0 aromatics or the bifunctional radical of a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated hetero- is a cyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals or sulfo, it being possible for two such bifunctional radicals to be connected via a bifunctional bridge,
- E 301 stands for N, C-Ar 302 or rO-Ar 302 An " ,
- R 302 and R 303 independently of one another are cyano, carboxylic acid, -CC 6 alkoxycarbonyl, aminocarbonyl or -CC 16 alkanoyl or R 303 is Ar 302 or R 302 ; R 303 together with the carbon atom connecting them represent a five- or six-membered carbocyclic or aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic or ionic radicals,
- E 303 to E 309 independently of one another represent CR 310 or N, the radicals R 310 being two
- Elements E 303 to E 309 together can form a 2- to 4-membered bridge, which
- E 305 -E 306 and / or E 307 -E 308 can represent a direct bond
- X 301 , X 302 , X 304 and X 306 independently of one another represent O, S or NR 300 and X 302 , X 304 and X 306 additionally represent CR 300 R 300 ,
- a 301 , B 301 and C 301 independently of one another represent a five- or six-membered aromatic, quasi-aromatic or partially hydrogenated heterocyclic ring which can be benzylated or naphthanellated and / or substituted by nonionic radicals,
- X 303 and X 305 independently of one another stand for N or (X 303 ) + -R 300 stands for O + or S + and / or ⁇ 3os_ R 3oo g jj . Is 0 or s;
- R 300 represents hydrogen, -CC 6 alkyl or C 7 -C 16 aralkyl or forms a ring to E 302 , E 303 or E 307 ,
- Y 301 stands for N or CR 301 ,
- R 301 represents hydrogen, CC 16 - alkyl, cyano, carboxylic acid, Q-Ci ⁇ - alkoxycarbonyl, C ⁇ -C 16 - alkanoyl or Ar 302 or a bridge to R 302 or Ar 303 ,
- v 1 or 2
- X 307 represents O, S or NR 311 ,
- R 311 and R 312 independently of one another represent hydrogen, -CC 16 alkyl, C 7 -C 6 aralkyl or C 6 -C ar_,
- Y 302 stands for NR 311 R 312 .
- Y 303 stands for CR 302 R 303 ,
- h and i independently of one another represent an integer from 0 to 3,
- w to z independently of one another represent an integer from 0 to 4, where w, x, y or z> 1 R, R, R or R can have different meanings,
- R 313 and R 314 are independently C ⁇ -C 16 alkoxy, C 6 -C ⁇ 0 aryloxy, hydroxy, halogen, cyano, thiocyanato, C j -C 12 -Alkylisonitrilo, Cg-Cig-ary !, C j -C 16 -alkyl, Cj-C ⁇ -alkyl- CO-O-, C r C 12 -alkyl-SO 2 -O-, C 6 -C ⁇ 0 -aryl-CO-O-, C6-C 1 o-aryl- S0 2 -0, tri- C r C 12 alkylsiloxy or NR 311 R 312 ,
- phthalocyanines of the formula (CCCIX) also mean the corresponding mono- to tetraza derivatives and their quaternary salts.
- Nonionic radicals are for example C alkyl, C 1 -C 4 alkoxy, halogen, cyano, nitro, CC 4 alkoxycarbonyl, C ⁇ -C 4 alkylthio, C ⁇ -C alkanoylamino, benzoylamino, mono- or di-C C 4 alkylamino.
- Alkyl, alkoxy, aryl and heterocyclic radicals can optionally carry further radicals such as alkyl, halogen, nitro, cyano, COOH, CO-NH 2 , alkoxy, trialkylsilyl, trialkylsiloxy, phenyl or S0 3 H, which can be alkyl and alkoxy radicals straight-chain or branched, the alkyl radicals can be partially or perhalogenated, the alkyl and alkoxy radicals can be ethoxylated or propoxy-hardened or silylated, adjacent alkyl and / or alkoxy radicals on aryl or heterocyclic radicals can together form a three- or four-membered bridge and that heterocyclic residues can be benzannelated and / or quaternized.
- further radicals such as alkyl, halogen, nitro, cyano, COOH, CO-NH 2 , alkoxy, trialkylsilyl, trialkylsiloxy, phen
- Light-absorbing compounds of the formulas (CCCI) to (CCCIX) are particularly preferred,
- Ar and Ar independently of one another for phenyl, naphthyl, benzthiazol-2-yl, benzoxazol-2-yl,
- Ar 303 represents phenylene, naphthylene, thiazole-2,5-diyl, thiophene-2,5-diyl or furan-2,5-diyl, which is represented by methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, hydroxy,
- Acetylamino, propionylamino, butanoylamino or benzoylamino can be substituted
- E 301 stands for N, C-Ar 302 or N " -Ar 302 An " ,
- R 302 and R 303 independently of one another represent cyano, carboxylic acid, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, methoxyethoxycarbonyl, acetyl, propionyl or butanoyl or R 303 represents Ar 302 or R 302 ; R 303 together with the connecting carbon atom for a ring of the formulas
- E 309 independently of one another represent CR 310 or N, two adjacent elements E 303 to E 309 for a bivalent grouping of the formulas
- R 310 for hydrogen, methyl, ethyl, cyano, chlorine, phenyl or a radical of the formula
- Beingnzo mustan-2-ylidene, l, 3-dithiol-2-ylidene, benzo-l, 3-dithiol -2-ylidene,
- Propyl, butyl, methoxy, ethoxy, propoxy, butoxy, chlorine, bromine, iodine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, acetylamino, propionylamino, butanoylamino or benzoylamino can be substituted,
- X 301 , X 302 , X 304 and X 306 independently of one another represent O, S or NR 300 and X 302 , X 304 and X 306 additionally represent CR 300 R 300 ,
- X 303 and X 305 independently of one another stand for N or (X 303 ) + -R 300 stands for 0 + or S + and / or X 305 -R 300 stands for O or S, and
- R 300 represents hydrogen, methyl, ethyl, propyl, butyl or benzyl
- R 300 represents methyl, ethyl, propyl, butyl or benzyl
- 7302 represents a bivalent radical of formula
- the six-membered ring can be substituted and / or benzanellated by methyl, ethyl, methoxy, ethoxy, propoxy, butoxy, acetamino, propionylamino or methylsulfonylamino,
- Y 301 stands for N or CR 301 ,
- R 301 represents hydrogen, methyl, ethyl, cyano, carboxylic acid, methoxycarbonyl, ethoxycarbonyl, acetyl or propionyl,
- v 1 or 2
- X 307 represents O, S or NR 311 ,
- R 311 and R 312 independently of one another represent hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, phenyl, which can be substituted by one or more of the radicals methoxy, ethoxy, propoxy, chlorine, bromine, dimethylamino or diethylamino .
- Y 302 stands for NR 311 R 312
- Y 303 stands for CR 302 R 303
- R 306 to R 309 independently of one another for methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, phenoxy, chlorine, bromine, -S0 3 H or
- w to z independently of one another represent an integer from 0 to 4, where w, x, y or z> 1
- R 306 , R 307 , R 308 or R 309 can have different meanings
- the monomers used to prepare the polymeric networks according to the invention have at least one functional group K-B of the formula (M1)
- pl stands for a number from 1 to 6, in particular stands for 2 or 3,
- p2 means 0 or 1
- p3 denotes 0 or 1
- R 150 for , OH or NH 2 , and at least one light absorbing group.
- Particularly suitable light-absorbing groups are those which, together with the functional group or groups, form a monomer with physical properties, such as absorption maxims, as described at the beginning.
- the light-absorbing groups of compounds are particularly preferably derived from the class of the merocyanine dyes and azo dyes.
- the monomers can be prepared by methods known to those skilled in the art.
- Monomers such as those of type P (M2) are suitable for polyadditions.
- Polyisocyanates are to be mentioned as preferred addition partners.
- Aromatic or aliphatic polyisocyanates are particularly preferred.
- Suitable polyisocyanates are known per se. These are aliphatic, aromatic and heterocyclic polyisocyanates, as described, for example, by W. Sirfken in Justus Liebigs Annalen der Chemie, 562, pages 75 to 136; for example ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1.12-dodecame ethylene diisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3- and -1,4-diisocyanate, and any mixtures of these isomers; l-isocyanato-3.3.5-trimethyl-5-isocyanatomethyl-cyclohexane, (DE-A 1 202 785; US-A 3 401 190) 2,4- and 2,6-hexahydrotoluenediisocyanate, hexahydro-1,3- and / or 1,
- polyisocyanates such as those obtained from diisocyanates of the aliphatic and aromatic series by biuretization, allophanatization and trimerization can be used.
- Dimerization, but also by urethanization with short-chain polyols with an OH functionality> 2 can be obtained. Accordingly, such polyisocyanates in addition to NCO groups also have biuret, allophanate, triazinetrione, uretdione and urethane structural elements. It is also possible to use asymmetrical trimerizates.
- the polyisocyanates can also be used as mixtures.
- Corresponding products from the aliphatic series are preferably used; allophanates, biurets, trimerizates and mixtures of trimerizates with uretdiones based on hexamethylene diisocyanate are particularly preferred.
- Particularly preferred monomers are those of the formulas below (Samples 1 to 42).
- the absorption spectra are preferably measured in solution.
- the invention further relates to a method for producing the optical data carrier, characterized in that containing a solution
- the invention also relates to the solution which is preferably used for the production of the optical data memory, hereinafter also called the composition, of the monomer on which the polymer network is based, optionally polymerization initiates, optionally further additives and at least one organic solvent.
- the preferred solvents are, for example, those solvents or solvent mixtures which, on the one hand, have sufficient solvent power and, on the other hand, have a minimal influence on the substrate for coating the monomers or their mixtures with additives and / or binders.
- Suitable solvents that have little influence on the substrate are, for example, alcohols, ethers, hydrocarbons, halogenated hydrocarbons, cellosolves, ketones.
- solvents examples include methanol, ethanol, propanol, 2,2,3,3-tetrafluoropropanol, butanol, diacetone alcohol, benzyl alcohol, tetrachloroethane, dichloromethane, diethyl ether, dipropyl ether, dibutyl ether, methyl tert-butyl ether, methyl cellosolve, ethyl cellosolve, l -Methyl-2-propanol, methyl ethyl ketone, 4-hydroxy-4-methyl-2-pentanone, hexane, cyclohexane, ethylcyclohexane, octane, benzene, toluene, xylene.
- Preferred solvents are hydrocarbons and alcohols because they have the least influence on the substrate.
- Possible polymerization initiators are, for example, free-radical initiators driven by heating, such as azodiisobuturonitrile or benzoyl peroxide. Preferred temperatures for activating these initiators are 30 to 130 ° C, preferably 40 to 70 ° C.
- Preferred photochemical initiators are for example 2,2-dimethoxy-l, 2-diphenyl-ethan-1-one; 2-methyl-l [4- (methylthio) phenyl] -2-morpholinopropan-l-one; 2-benzyl-2-di- methylamino-1 - (4-morpholinophenyl) .butanone-1; 1-hydroxy-cyclohexyl-phenyl-ketone; 2-hydroxy-2-methyl-lphenyl-propan-1-one or titanocene dichloride.
- the invention further relates to a method for producing the optical data memory according to the invention, characterized in that at least one polymer layer containing a crosslinked polymer based on the monomers on which the polymer network is based, in particular of
- the invention further relates to polymer layers composed of at least one crosslinked polymer based on
- crosslinked polymers used for the polymer layers according to the invention correspond to the preferred polymeric networks defined above.
- the polymer layers preferably have a thickness of 10 to 1000 nm.
- the invention further relates to a process for the preparation of the polymer layers according to the invention, characterized in that the monomers on which the polymer network is based, in particular the solution according to the invention, are applied to a suitable releasable carrier, the polymerization is initiated and the solvent preferably used during or is removed after the polymerization and the steps of applying the solution, polymerizing and, if appropriate, removing the solvent are repeated, if appropriate several times, the second and each further layer being applied to the last layer in each case and then the removable support being removed again.
- Such polymer layers can then be used for the production of optical data carriers.
- 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 invention further relates to a write-once optical data carrier comprising a preferably transparent substrate, on the surface of which at least one information layer which can be written with light, optionally a reflection layer and / or optionally a protective layer, is applied, which is coated with blue, red or infrared light, preferably laser light, can be described and read, the information layer containing a polymeric network with covalently bound chromophoric centers.
- the structure of the optical data carrier can be:
- Information layer which can be written on by light, optionally a reflection layer and optionally an adhesive layer and another preferably transparent substrate are applied.
- Reflection layer at least one information layer which can be written on with light, optionally an adhesive layer and a transparent cover layer are applied.
- the optical data storage device can carry further layers such as metal layers, dielectric layers and protective layers.
- metal layers metal layers, dielectric layers and protective layers.
- Metals can depending on the laser wavelength, gold, silver, aluminum and others.
- Dielectric layers are, for example, silicon dioxide and silicon nitride. Metal layers and dielectric layers are preferably distinguished by the fact that they are applied by sputtering or vapor deposition and have thicknesses in the range from 1 nm to 150 nm, preferably from 1 nm to 100 nm.
- Protective layers are, for example, dielectric layers, photocurable lacquers, (pressure-sensitive) adhesive layers and protective films.
- Pressure-sensitive adhesive layers mainly consist of acrylic adhesives.
- 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 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 cover layer (6) are applied.
- a transparent substrate (1) on the surface of which a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
- a transparent substrate (1) on the surface of which there is optionally a protective layer (2), at least one information layer (3) which can be written on with light, preferably laser light, optionally a protective layer (4), optionally an adhesive layer (5), and a transparent cover layer (6) are applied.
- a preferably transparent substrate (1) on the surface of which at least one information layer (3) which can be written on with light, preferably laser light, optionally an adhesive layer (5) and a transparent cover layer (6) are applied.
- the optical data carrier has, for example, the following layer structure (cf. FIG. 2): a preferably transparent substrate (11), an information layer (12), optionally one 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), an information layer (22), optionally a reflection layer (23), a protective layer (24).
- the optical data carrier has, for example, the following layer structure (cf. FIG. 4): a preferably transparent substrate (31), optionally a reflection layer (32), an information layer (33), a protective layer (34).
- the invention further relates to optical data carriers according to the invention described with blue, red or infrared light, in particular laser light.
- the invention also relates to the optical data storage media according to the invention after they have been described once with blue, red or infrared light, in particular laser light.
- the invention relates to the use of light-absorbing compounds which are integrated in a polymer network and which have at least one absorption maximum in the range from 340 to 820 nm in the information layer of optical data carriers which have been written once.
- the preferred ranges for the light-absorbing connections, for the information layers produced therefrom, and for the optical data carriers also apply to the use according to the invention.
- the information layer can also contain initiators, stabilizers, thinners and sensitizers and further constituents, and also non-covalently bound light-absorbing compounds or residues of monomers which did not take part in the crosslinking reaction.
- the substrates for the manufacture of the optical data storage media can be made of optically transparent plastics which, if necessary, have undergone a surface treatment. It is preferably plastics such as polycarbonates or polyacrylates, and also polycycloolefins or polyolefins.
- the light-absorbing compound can also be used in low concentration to protect the polymer substrate and stabilize it.
- the reflection layer can be made from any metal or metal alloy that is usually used for writable optical data carriers. Suitable metals or metal Alloys can be vapor-deposited and sputtered and contain, for example, gold, silver, copper, aluminum and their alloys with one another or with other metals.
- the protective varnish over the reflective layer can consist of UV-curing resins.
- An intermediate layer that protects the reflection layer from oxidation can also be present.
- suitable initiators preferably photoinitiators
- the crosslinking of the monomers can also take place after one of the various subsequent steps in the construction of the optical data carrier instead
- the monomers are preferably cured by optionally mixing the monomers to be added with suitable catalysts and or additives, applying them to the substrate, preferably by spin coating and polyaddition at a temperature of 10 to 130 ° C.
- the coating of the substrate with the monomers to be polymerized, optionally in combination with initiators, additives and / or solvents, is preferably carried out by spin coating.
- the monomers are preferably dissolved with or without initiators and additives in a suitable solvent or solvent mixture, so that the monomers make up 100 or less, for example 10 to 2 parts by weight to 100 parts by weight of solvent.
- Solvents or solvent mixtures for coating the curable monomers of the polymer network or their mixtures with initiators, additives and / or auxiliaries are selected on the one hand according to their solvency for the light-absorbing compound and the other additives and on the other hand according to a minimal influence on the substrate.
- Suitable solvents that have a minor influence on the substrate are, for example, alcohols, ethers, hydrocarbons, halogenated hydrocarbons, cellosolves, ketones.
- solvents examples include methanol, ethanol, propanol, 2,2,3,3-tetrafluoropropanol, butanol, diacetone alcohol, benzyl alcohol, tetrachloroethane, dichloromethane, diethyl ether, di-propyl ether, dibutyl ether, methyl tert-buryl ether, methyl cellosolve, ethyl cellosolve, l -Methyl-2-propanol, methyl ethyl ketone, 4-hydroxy-4-methyl-2-pentanone, hexane, cyclohexane, ethylcyclohexane, done, benzene, toluene, xylene.
- Preferred solvents are hydrocarbons and alcohols because they have the least influence on the substrate.
- Suitable additives for the recordable information layer are stabilizers, thinners and sensitizers.
- the coating which is preferably produced by spin coating, is then cured.
- a preferred method for curing the information layers is chain polymerization (very particularly preferred is radical polymerization) of the curable monomers, under the action of polymerization initiators, preferably under the action of the radical-delivering polymerization initiators, such as e.g. Azodiisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), dimethyl 2,2'-azobis-isibutyrate, 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2.2 'Azobis (2-methylbutyronitrile) or benzoyl peroxide, at elevated temperatures, usually at 30 to 130 ° C, preferably at 40 to 70 ° C.
- radical-delivering polymerization initiators such as e.g. Azodiisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), dimethyl 2,2'-azobis-isibutyrate, 2,2'-azobis (4-
- the polymerization can also be carried out using a mixture of two or more thermal and photoinitiators.
- the information layer can no longer be removed with the abovementioned solvents.
- the curing to the polymeric network does not necessarily have to be complete. It is also possible to achieve, for example, shorter curing times, degrees of curing of only 30% or more. A degree of curing of at least 30% is preferred, which corresponds to a content of non-crosslinked functional groups of at most 70%. A degree of curing of more than 35%, in particular more than 40%, is preferred.
- Optical data storage media which also contain the corresponding monomers in addition to the polymer network in their information layer are therefore preferred.
- the recordable information layer is then preferably metallized at reduced pressure by sputtering or vapor deposition (reflection layer) and possibly subsequently provided with a protective lacquer (protective layer) or another substrate or a covering layer.
- a protective lacquer protective layer
- Multi-layer arrangements with partially transparent reflection layers are also possible.
Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/549,100 US20070042295A1 (en) | 2003-03-25 | 2004-03-12 | Optical data carrier comprising a polymeric network in the information layer |
EP04719936A EP1611574A1 (de) | 2003-03-25 | 2004-03-12 | Optischer datenträger mit polymerem netzwerk in der informationsschicht |
JP2006500060A JP2006521220A (ja) | 2003-03-25 | 2004-03-12 | 情報層中にポリマー網目を含有する光学データ媒体 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10313173.6 | 2003-03-25 | ||
DE10313173A DE10313173A1 (de) | 2003-03-25 | 2003-03-25 | Optischer Datenträger mit polymerem Netzwerk in der Informationsschicht |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004086390A1 true WO2004086390A1 (de) | 2004-10-07 |
Family
ID=32946116
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/002585 WO2004086390A1 (de) | 2003-03-25 | 2004-03-12 | Optischer datenträger mit polymerem netzwerk in der informationsschicht |
Country Status (7)
Country | Link |
---|---|
US (1) | US20070042295A1 (de) |
EP (1) | EP1611574A1 (de) |
JP (1) | JP2006521220A (de) |
CN (1) | CN1764962A (de) |
DE (1) | DE10313173A1 (de) |
TW (1) | TW200504737A (de) |
WO (1) | WO2004086390A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006133846A2 (de) | 2005-06-17 | 2006-12-21 | Bayer Materialscience Ag | Optischer datenspeicher, dessen herstellung und verwendung |
US7718242B2 (en) * | 2006-01-10 | 2010-05-18 | Industrial Technology Research Institute | Organic dyes for recording layer and high density optical recording medium using the same |
US7758943B2 (en) * | 2006-01-10 | 2010-07-20 | Industrial Technology Research Institute | Organic dye for recording layer and high density optical recording medium using the same |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5333734B2 (ja) * | 2008-02-28 | 2013-11-06 | Jsr株式会社 | 感放射線性樹脂組成物および液晶表示素子用スペーサー |
FR2967900B1 (fr) * | 2010-11-25 | 2024-01-05 | Oreal | Composition contenant un filtre dibenzoylmethane et un filtre uv merocyanine hydrophile ou hydrosoluble ; procede de photostabilisation du filtre dibenzoylmethane |
JP6154898B2 (ja) * | 2013-05-27 | 2017-06-28 | 富士フイルム株式会社 | 光情報記録媒体 |
WO2015103587A2 (en) * | 2014-01-06 | 2015-07-09 | The University Of North Carolina At Chapel Hill | Improved environment sensing cyanine and merocyanine dyes |
KR20170131339A (ko) * | 2015-03-27 | 2017-11-29 | 가부시키가이샤 아데카 | 메로시아닌 화합물 |
KR102507765B1 (ko) * | 2016-09-05 | 2023-03-08 | 가부시키가이샤 아데카 | 폴리메틴 화합물 |
KR20200067832A (ko) * | 2017-10-13 | 2020-06-12 | 스미또모 가가꾸 가부시키가이샤 | 수지 및 점착제 조성물 |
JP2019199436A (ja) * | 2018-05-16 | 2019-11-21 | 東洋インキScホールディングス株式会社 | モルホリン環含有(メタ)アクリレート化合物およびそれを用いた重合性組成物 |
JPWO2020218297A1 (de) * | 2019-04-26 | 2020-10-29 | ||
JP7258155B2 (ja) * | 2019-08-15 | 2023-04-14 | 富士フイルム株式会社 | 重合性組成物、化合物、重合体、樹脂組成物、紫外線遮蔽膜及び積層体 |
JPWO2021172179A1 (de) * | 2020-02-28 | 2021-09-02 | ||
WO2024044214A1 (en) * | 2022-08-22 | 2024-02-29 | University Of Connecticut | Hemicyanine push-pull dyes based on chromene electron donors |
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US3808305A (en) * | 1971-07-27 | 1974-04-30 | H Gregor | Crosslinked,interpolymer fixed-charge membranes |
US4666819A (en) * | 1985-03-11 | 1987-05-19 | Minnesota Mining And Manufacturing Company | Optical information storage based on polymeric dyes |
DE3801546A1 (de) * | 1987-01-20 | 1988-07-28 | Hitachi Maxell | Optisches informationsaufzeichnungsmedium und verfahren zu seiner herstellung |
US5173381A (en) * | 1991-08-05 | 1992-12-22 | Queen's University | Azo polymers for reversible optical storage |
DE19620588A1 (de) * | 1996-05-22 | 1997-11-27 | Bayer Ag | Schnell fotoadressierbare Substrate, ein Verfahren zum Beschreiben dieser Substrate und ihre Verwendung |
-
2003
- 2003-03-25 DE DE10313173A patent/DE10313173A1/de not_active Withdrawn
-
2004
- 2004-03-12 US US10/549,100 patent/US20070042295A1/en not_active Abandoned
- 2004-03-12 WO PCT/EP2004/002585 patent/WO2004086390A1/de not_active Application Discontinuation
- 2004-03-12 CN CNA2004800082190A patent/CN1764962A/zh active Pending
- 2004-03-12 JP JP2006500060A patent/JP2006521220A/ja not_active Withdrawn
- 2004-03-12 EP EP04719936A patent/EP1611574A1/de not_active Withdrawn
- 2004-03-24 TW TW093107857A patent/TW200504737A/zh unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US3808305A (en) * | 1971-07-27 | 1974-04-30 | H Gregor | Crosslinked,interpolymer fixed-charge membranes |
US4666819A (en) * | 1985-03-11 | 1987-05-19 | Minnesota Mining And Manufacturing Company | Optical information storage based on polymeric dyes |
DE3801546A1 (de) * | 1987-01-20 | 1988-07-28 | Hitachi Maxell | Optisches informationsaufzeichnungsmedium und verfahren zu seiner herstellung |
US5173381A (en) * | 1991-08-05 | 1992-12-22 | Queen's University | Azo polymers for reversible optical storage |
DE19620588A1 (de) * | 1996-05-22 | 1997-11-27 | Bayer Ag | Schnell fotoadressierbare Substrate, ein Verfahren zum Beschreiben dieser Substrate und ihre Verwendung |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006133846A2 (de) | 2005-06-17 | 2006-12-21 | Bayer Materialscience Ag | Optischer datenspeicher, dessen herstellung und verwendung |
TWI402831B (zh) * | 2005-06-17 | 2013-07-21 | Bayer Materialscience Ag | 光學資料儲存媒體及其製造與用途 |
KR101296525B1 (ko) * | 2005-06-17 | 2013-08-13 | 바이엘 머티리얼사이언스 아게 | 광 데이터 메모리, 이의 제조 및 이의 용도 |
US7718242B2 (en) * | 2006-01-10 | 2010-05-18 | Industrial Technology Research Institute | Organic dyes for recording layer and high density optical recording medium using the same |
US7758943B2 (en) * | 2006-01-10 | 2010-07-20 | Industrial Technology Research Institute | Organic dye for recording layer and high density optical recording medium using the same |
Also Published As
Publication number | Publication date |
---|---|
JP2006521220A (ja) | 2006-09-21 |
EP1611574A1 (de) | 2006-01-04 |
US20070042295A1 (en) | 2007-02-22 |
TW200504737A (en) | 2005-02-01 |
DE10313173A1 (de) | 2004-10-07 |
CN1764962A (zh) | 2006-04-26 |
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