WO2002080163A1 - Optischer datenträger enthaltend in der informationsschicht eine cyclisierbare verbindung - Google Patents
Optischer datenträger enthaltend in der informationsschicht eine cyclisierbare verbindung Download PDFInfo
- Publication number
- WO2002080163A1 WO2002080163A1 PCT/EP2002/003070 EP0203070W WO02080163A1 WO 2002080163 A1 WO2002080163 A1 WO 2002080163A1 EP 0203070 W EP0203070 W EP 0203070W WO 02080163 A1 WO02080163 A1 WO 02080163A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- alkoxycarbonyl
- hydrogen
- aryl
- bromine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 230000003287 optical effect Effects 0.000 title claims abstract description 38
- 239000010410 layer Substances 0.000 claims abstract description 50
- 239000011241 protective layer Substances 0.000 claims abstract description 16
- 239000000758 substrate Substances 0.000 claims abstract description 14
- 239000012790 adhesive layer Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 89
- 239000001257 hydrogen Substances 0.000 claims description 89
- 150000002431 hydrogen Chemical class 0.000 claims description 78
- -1 hetaryl radical Chemical class 0.000 claims description 76
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 46
- 229910052794 bromium Inorganic materials 0.000 claims description 46
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 43
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 39
- 229910052801 chlorine Inorganic materials 0.000 claims description 39
- 239000000460 chlorine Substances 0.000 claims description 39
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 238000010521 absorption reaction Methods 0.000 claims description 20
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 239000000975 dye Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- JONIMGVUGJVFQD-UHFFFAOYSA-N (4-methylphenyl)sulfonylformonitrile Chemical compound CC1=CC=C(S(=O)(=O)C#N)C=C1 JONIMGVUGJVFQD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 229910052779 Neodymium Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 3
- VHVGFEDTMPYCSX-UHFFFAOYSA-N [1-[[2,2-dimethyl-3-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]propoxy]methyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCC(C)(C)COCN1C=CC(=C[NH+]=O)C=C1 VHVGFEDTMPYCSX-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical compound BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims 66
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000007363 ring formation reaction Methods 0.000 description 23
- 239000010408 film Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000002310 reflectometry Methods 0.000 description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 6
- 238000013500 data storage Methods 0.000 description 6
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000411 transmission spectrum Methods 0.000 description 3
- 0 CC(C(*)=C(*)*)=C1NC(*)Cc2c(*)c(C)c(C)c(*)c12 Chemical compound CC(C(*)=C(*)*)=C1NC(*)Cc2c(*)c(C)c(C)c(*)c12 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- YLIPVATXZMFSCL-UHFFFAOYSA-N 3-ethenylchromen-2-one Chemical compound C1=CC=C2OC(=O)C(C=C)=CC2=C1 YLIPVATXZMFSCL-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- VASUQTGZAPZKFK-UHFFFAOYSA-N 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline Chemical compound C1CN=C(C)C2=C1C=C(OC)C(OC)=C2 VASUQTGZAPZKFK-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- ABRWESLGGMHKEA-UHFFFAOYSA-N n-tert-butylaniline Chemical compound CC(C)(C)NC1=CC=CC=C1 ABRWESLGGMHKEA-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
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- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
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- C09B23/10—The polymethine chain containing an even number of >CH- groups
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- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
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- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
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- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
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- G11B7/004—Recording, reproducing or erasing methods; Read, write or erase circuits therefor
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- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
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- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers
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- 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
- G11B7/007—Arrangement of the information on the record carrier, e.g. form of tracks, actual track shape, e.g. wobbled, or cross-section, e.g. v-shaped; Sequential information structures, e.g. sectoring or header formats within a track
Definitions
- the invention relates to a write-once optical data carrier, which in the
- Information layer contains a cyclizable, light-absorbing compound, as well as a process for the production of the optical data carriers, their use and still new cyclizable light-absorbing compounds.
- the write-once optical data carriers using special light-absorbing substances or mixtures thereof are particularly suitable for use with high-density writable optical data storage devices that work with blue laser diodes, in particular GaN or SHG laser diodes (360 - 460 nm) and / or for use with DVD-R or CD-R discs that work with red (635 - 660 nm) or infrared (780 - 830 nm) laser diodes, as well as the application of the above-mentioned dyes to a polymer substrate, in particular polycarbonate, by spin coating or vapor deposition.
- blue laser diodes in particular GaN or SHG laser diodes (360 - 460 nm) and / or for use with DVD-R or CD-R discs that work with red (635 - 660 nm) or infrared (780 - 830 nm) laser diodes, as well as the application of the above-mentioned dyes to a polymer substrate,
- the next generation of optical data storage media - the DVD - is currently being launched on the market.
- the storage density can be increased by using shorter-wave laser radiation (635 to 660 nm) and a higher numerical aperture NA.
- the recordable format in this case is the DVD-R.
- the writable information layer made of light-absorbing organic substances must have a morphology which is as amorphous as possible in order to keep the noise signal as small as possible when writing or reading.
- the substances are applied by spin coating from a solution, by vapor deposition and / or sublimation, subsequent crystallization of the light-absorbing substances with metallic or dielectric layers in vacuum is prevented.
- the amorphous layer of light-absorbing substances should preferably have a high heat resistance, since otherwise further layers of organic or inorganic material, which are applied to the by sputtering or vapor deposition light-absorbing information layer are applied, form diffuse interfaces by diffusion and thus adversely affect the reflectivity.
- a light-absorbing substance with too low heat resistance at the interface to a polymeric carrier can diffuse in the latter and in turn adversely affect the reflectivity.
- An excessively high vapor pressure of a light-absorbing substance can sublimate the above-mentioned sputtering or vapor deposition of further layers in a high vacuum and thus reduce the desired layer thickness. This in turn leads to a negative influence on the reflectivity.
- the object of the invention is therefore to provide suitable compounds which meet the high requirements (such as light stability, favorable signal-to-noise ratio, damage-free application to the substrate material, etc.) for use in the information layer in a write-once optical data carrier, in particular for high-density recordable optical media Meet data storage formats in a laser wavelength range from 360 to 460 nm.
- the invention therefore relates to an optical data carrier, comprising a preferably transparent substrate, possibly already coated with a protective layer, on the surface of which an information layer which can be written on with light, optionally a protective layer, optionally an adhesive layer and finally a cover layer which is coated with blue light are applied , preferably laser light, particularly preferably light with 360-460 nm, in particular 380-440 nm, very particularly preferably at 395-415 nm can be written and read, the information layer containing a light-absorbing compound and optionally a binder, characterized in that the light absorbing compound has a chemical arrangement that cyclizes thermally to 5, 6 or 7 rings when written.
- the light-absorbing compound should preferably be caused to shift the local absorption maximum in the range of 350-470 nm by the thermal cyclization of the chemical arrangement.
- the shift is more than 25 nm ( ⁇ max), particularly preferably more than 35 nm, very particularly preferably more than 45 nm.
- the shift is preferably hypsochromic.
- the thermal change is preferably carried out at a temperature ⁇ 600 ° C., particularly preferably at a temperature ⁇ 400 ° C., very particularly preferably at a temperature ⁇ 300 ° C., in particular ⁇ 200 ° C.
- the thermal cyclization is likewise preferably carried out only at a temperature of> 100 ° C., in particular> 140 ° C., preferably at> 180 ° C.
- the cyclization temperature T C y C is determined, for example, by means of differential thermal analysis DTA. In the preferred exothermic cyclization, it corresponds to the maximum of the rearrangement signal.
- the heating rate for DTA measurements is, for example, 10 ° C per minute.
- the full width at half maximum of the rearrangement signal under these conditions is preferably less than 10 ° C., particularly preferably less than 7 ° C., very particularly preferably less than 5 ° C.
- Half-width in the sense of the invention is the width of the signal that the signal has halfway up from the base point to the maximum.
- a compound which has a chemical arrangement which can thermally cyclize to 5-, 6- or 7-rings is preferably used as the light-absorbing compound.
- a compound which corresponds to the formula (I) or (II) is particularly preferably used as the light-absorbing compound.
- X 1 represents NR 1 , O or S
- X 2 represents CR 2 or N
- X 3 represents CR 3 or N
- X 4 represents CR 4 or N
- X 3 is CR D or N, where in the row X ⁇ 2 - no two nitrogen atoms are adjacent X5 v D - v X3 J - v X
- n, m independently of one another represent 0 or 1
- R 1 is hydrogen, Ci to C 6 alkyl, Ci to C 6 alkenyl, Ci to C 6 alkynyl, C 4 to C 7 cycloalkyl, C 7 to Cis aralkyl, Ci to C 6 -alkoxycarbonyl, aryl or
- Hetaryl where the hetaryl radical can contain up to 3 heteroatoms and the aryl or hetaryl radical can be substituted by up to 3 nonionic radicals,
- R 2 represents hydrogen, bromine, Ci to C 6 alkyl, Ci to C 6 alkenyl, Ci to C 6 alkynyl, C 6 to C 10 aryl, C 7 to s-araryl, hetaryl, Ci to C 6 alkoxy, mono- or di-Cr to C 6 alkylamino, N-Ci to C 6 alkyl-NC 6 to C 10 arylamino or with R 1 together part of a five- or sixth is a membered aromatic or partially hydrogenated ring which may contain 1 to 4 heteroatoms or carbonyl groups and / or benzene or naphthane fused and / or may be substituted by nonionic, preferably electron donor,
- R 3 for hydrogen, Cj to C 6 alkyl, Ci to C 6 alkenyl, C 6 to C 10 aryl, C 7 to C 15 araryl, hetaryl, Ci to C 6 alkoxycarbonyl, formyl , Cyano, nitro, halogen or together with R 2 is part of a five- or six-membered aromatic or partially hydrogenated ring which may contain 1 to 4 heteroatoms or carbonyl groups and / or benzylated or naphthanellated and / or their rings by nonionic radicals can be substituted
- R 4 for hydrogen, amino, bromine, Ci to C 6 alkyl, Cr to C 6 alkenyl, Ci to
- Alkyl-NC 6 - to Qo-arylamino or together with R 3 is part of a five- or is a 6-membered aromatic or partially hydrogenated ring which may contain 1 to 4 heteroatoms or carbonyl groups and / or benzylated or naphthanellated and / or substituted by nonionic, preferably electron donor,
- Residues can be substituted,
- R 6 represents hydrogen, bromine, chlorine, methoxy or ethoxy
- R 7 represents hydrogen, bromine, chlorine or methoxy if R 6 represents methoxy or represents ethoxy if R 6 represents ethoxy,
- R 8 represents bromine, chlorine, iodine, cyano, tosylate, trifiate, Ci to C 6 alkanoyloxy, C to C 6 alkylthio or represents methoxy if R 7 represents methoxy or represents ethoxy if R 7 represents ethoxy,
- R 9 , R 10 and R n independently of one another for Ci to C 6 alkoxy, chlorine, bromine, iodine, Ci to C 6 alkanoyloxy, Ci to C 6 alkylthio, C 6 to o-aryloxy, C 6 - are to Cio-arylcarbonylamino or one of these radicals together with R 5 is part of a five- or six-membered aromatic or partially hydrogenated ring which
- R 12 is hydrogen, Ci to C 6 alkyl, d to C 6 alkenyl, Q to C 6 alkynyl, C 4 to C 7 cycloalkyl, C 7 to C 15 aralkyl, Ci to C 6 alkoxycarbonyl, aryl or Hetaryl, where the hetaryl radical can contain up to 3 heteroatoms and the aryl or hetaryl radical can be substituted by up to 3 nonionic radicals,
- R 13 5 R 14 , R 17 , R 18 , R 21 and R 22 independently of one another represent hydrogen, CC 3 alkyl, fluorine, chlorine or bromine,
- R 16 and R 20 independently of one another for hydrogen, d- to C 6 - alkyl, Ci to C 6 -
- R 24 stands for O, S or NR 35 ,
- R 26 , R 29 , R 32 and R 35 independently of one another are hydrogen, Ci to C 6 alkyl, Ci to C 6 alkenyl, C to C 6 alkynyl, C 4 to C 7 cycloalkyl, C 7 - to cis
- Aralkyl, Ci- to C 6 alkoxycarbonyl are, aryl or hetaryl, wherein the hetaryl radical can contain up to 3 hetero atoms, and the aryl or
- Hetarylrest can be substituted by up to 3 nonionic residues and R 27 , R 28 , R 30 , R 31 , R 33 and R 34 independently of one another for hydrogen, C r to C 6 alkyl, Ci to C 6 alkenyl, C 4 to C 7 cycloalkyl, C 7 to Cis-aralkyl, aryl or hetaryl, where the hetaryl radical can contain up to 3 heteroatoms and the aryl or hetaryl radical can be substituted by up to 3 nonionic radicals.
- X 1 , X 2 , X 3 , X 4 , X 5 , X 7 , X 8 , X 9 , n and m have the meaning given above.
- R 6 , R 7 and R 12 have the meaning given above.
- nonionic radicals are Ci to C alkyl, Ci to C 6 alkoxy, halogen, cyano, nitro, d to C alkoxycarbonyl, Ci to C alkylthio, Ci to C 4 Alkanoylamino, benzoylamino, mono- or di-d to C -alkylamino, Ci- to C 6 -alkanoyloxy, l- (l, 2,3) triazole and 2- (l, 2,3) triazole in question.
- Electron donor residues are, for example, Ci to C 4 alkoxy, C 6 to Cio aryloxy, mono- or di-d to C 6 alkylamino, Nd to C 6 alkyl-NC 6 to do-arylamino.
- hetaryl examples include pyrrole, thiophene, furan, oxazole, isoxazole, imidazole, pyrazole, thiazole, isothiazole, pyridine, pyrimidine, pyridazine, pyrazine, 1,2,3-triazole, 1, 2,4-triazole and their benzene-fused representatives Question.
- Hetaryl in the sense of the invention are also piperidine, pyrrolidine, morpholine, piperazine and chroman.
- Alkyl, alkoxy, aryl and heterocyclic radicals can optionally further radicals such as alkyl, halogen, nitro, cyano, CO-NH 2 , alkoxy, trialkylsilyl,
- 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 methoxylated, ethoxylated or propoxylated 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 benzannellated and / or quaternized.
- the light-absorbing compounds of the formula I used are those which correspond to the formula (III) (the group capable of cyclization is highlighted in bold).
- R > 45 represents hydrogen, bromine, chlorine, Ci to C alkyl, Cj to C 4 alkoxy, cyano, Ci to C alkoxycarbonyl, mono- or di Cj to C 4 alkylamino,
- R 46 , R 47 , R 48 and R 49 independently of one another for hydrogen, methyl, ethyl, Ci to C 6 - alkoxy, fluorine, chlorine, bromine, cyano, nitro, Ci to C -alkoxycarbonyl, mono- or di- d to C alkylamino,
- R 50 represents hydrogen, methyl, cyano, C 1 -C 6 -alkoxycarbonyl, formyl, bromine, chlorine,
- R > 51 for hydrogen, methyl, bromine, amino, N-methylamino, dimethylamino,
- R, 52 stands for cyano, C] - to d-alkoxycarbonyl, C 6 - to do-aryloxycarbonyl, Cj- to C 6 -alkanoyloxycarbonyl and
- X 6 represents cyano, Ci to C 6 alkoxycarbonyl, C 6 to C 10 aryloxycarbonyl, Ci to C 6 alkanoyloxycarbonyl or -CH 2 -O-SO 2 - ⁇ - C 6 H -CH 3 .
- the dyes of the formula (III) are very particularly preferred Wonn
- R 45 represents hydrogen, methyl, ethyl, isopropyl
- R 46 , R 49 represents hydrogen
- R 47 , R 48 independently of one another represent hydrogen, Ci to C 6 alkoxy, mono- or di-Ci to C 4 alkylamino,
- R 50 is hydrogen, methyl, cyano, Ci to C ö alkoxycarbonyl,
- R 51 represents hydrogen, methyl, amino, N-methylamino, dimethylamino, methoxy, ethoxy,
- X 6 for cyano Ci to C 6 alkoxycarbonyl, C 6 to Cio aryloxycarbonyl, Ci to C 6 alkanoyloxycarbonyl, -CH 2 -O-SO 2 - . pC 6 H -CH 3 .
- the light-absorbing compounds of the formula (III) are particularly preferred,
- R 45 , R 46 , R 49 represents hydrogen
- R 47 , R 48 independently of one another represent hydrogen, C 1 -C 3 -alkoxy, mono- or di-C 1 to d-alkylamino,
- R> 50 ⁇ R51 stands for hydrogen
- R 52 is cyano
- Ci to C stands 6 and alkanoyloxycarbonyl
- X 6 represents cyano, Ci to C 6 alkoxycarbonyl, C 6 to do aryloxycarbonyl.
- ⁇ 6a represents c-NH, CO or CH 2 .
- the light-absorbing compounds of the formula I used are those which correspond to the formula (IV)
- R 66 represents hydrogen, bromine, chlorine, d to C alkyl, Ci to C 6 alkoxy, cyano, d to C alkoxycarbonyl, mono- or di-d to C 4 alkylamino,
- R, R, R and R independently of one another are hydrogen, methyl, ethyl, isopropyl, d- to C 6 -alkoxy, fluorine, chlorine, bromine, cyano, nitro, d- to C 4 -alkoxycarbonyl, mono- or di Ci bis C 4 alkylamino, d- to C 4 -
- R can additionally stand for l, 2,3-triazol-2-yl, which can also be benzene-fused or naphthane-fused at the 4,5-position,
- R 72 represents O, NH, N-Ci to NC 3 alkyl
- R 73 represents O, Nd to NC 6 alkyl, NC 6 to C 10 aryl,
- Hetaryl stands, where the hetaryl residue can contain up to 3 heteroatoms and the aryl or hetaryl radical can be substituted by up to 3 nonionic radicals.
- R 66 represents hydrogen, Ci to C 4 alkyl, Ci to C 6 alkoxy, cyano, mono- or di- Ci to C alkylamino,
- R 67 represents hydrogen, d- to C 6 alkyl, C 6 - to C 10 -aryl, hetaryl, Ci to C 6 - alkoxycarbonyl, formyl, cyano, nitro, halogen,
- R 68 , R 71 stand for hydrogen
- R 68 , R 69 can additionally form a butadiene bridge
- R 69 and R 70 independently of one another represent hydrogen, methyl, Ci to C 2 alkoxy, chlorine, Ci to C 2 alkoxycarbonyl, mono- or di Ci to C 4 alkylamino, d- to C -alkanoyloxy,
- R 70 can additionally represent l 5 2,3-triazol-2-yl, which can also be benzene-fused or naphthane-fused at the 4,5-position,
- R 72 represents O or NH
- R 73 stands for O
- R 66 , R 67 , R 68 and R 71 represent hydrogen
- R 69 and R 70 independently of one another are hydrogen, methyl, Ci to C 2 alkoxy,
- R 72 represents O or NH
- X> -6 D is cyano, Ci to C 6 alkoxycarbonyl, C 6 - to Cio-aryloxycarbonyl and is
- R> 7 "5 represents hydrogen, d- to C 6 -alkyl, C 5 - to C 6 -cycloalkyl, C 7 - to -CC 5 aralkyl, Ci to C 6 - alkoxycarbonyl, aryl.
- R 68 - R 73 and R 75 have the meaning given above and
- the thermally cyclizable dye used is one of the formula (V)
- X 1 represents NR 1 , O or S
- R is hydrogen, Ci to C 6 alkyl, Ci to C 6 alkenyl, Ci to C 6 alkynyl, C to C 7 cycloalkyl, C 7 to C 5 aralkyl, Ci to C 6 Alkoxycarbonyl, aryl or hetaryl, where the hetaryl radical can contain up to 3 heteroatoms and the aryl or hetaryl radical can be substituted by up to 3 nonionic radicals,
- R 85 , R 86 , R 87 , R 88 independently of one another are hydrogen, methyl, ethyl, isopropyl, Ci to C 6 alkoxy, fluorine, chlorine, bromine, cyano, nitro, Ci to C 4 alkoxycarbonyl, Mono- or Di Ci to C 4 alkylamino, Ci to C alkanoyloxy or 2 adjacent radicals form a butadiene bridge, R 87 can additionally stand for l, 2,3-triazol-2-yl, which can also be benzene-fused or naphthane-fused at the 4,5-position,
- R > 8 a 9 y represents O, NH, N-Ci to NC 3 alkyl
- R > 9 y 0 ⁇ is O, N-Ci to C 6 alkyl or NC 6 to C 10 aryl
- R 95 represents hydrogen, Ci to C 6 alkyl, Ci to C 6 alkenyl, C 4 to C 7 cycloalkyl,
- R 98 represents hydrogen, bromine, chlorine, methoxy or ethoxy
- R 99 stands for hydrogen, bromine, chlorine or for methoxy if R 98 stands for methoxy or stands for ethoxy if R 98 stands for ethoxy,
- R 100 represents leaving groups such as bromine, chlorine, iodine, cyano, tosylate, triflate, Ci to C 6 alkanoyloxy, Ci to C 6 alkylthio or represents methoxy if R 99 represents methoxy or represents ethoxy if R 99 represents ethoxy, R 101 , R 102 and R 103 for d- to C 6 -alkoxy, chlorine, bromine, iodine, d- to C 6 -alkanoyloxy 5 Cj- to C 6 -alkylthio, C 6 - to Cio-aryloxy, C 6 - to Cio-arylcarbonylamino and
- R 104 for hydrogen, Ci to C 6 alkyl, d to C 6 alkenyl, d to C 6 alkynyl, C 4 to C 7 cycloalkyl, C to C 5 aralkyl, Ci to C 6 -alkoxycarbonyl, aryl or hetaryl, where the hetaryl radical can contain up to 3 heteroatoms and the aryl or hetaryl radical can be substituted by up to 3 nonionic radicals.
- X 1 represents NR 1 , O or S
- R 1 represents hydrogen, Ci to C 6 alkyl, C 5 to C 6 cycloalkyl, C r to C 6 alkoxycarbonyl, aryl,
- R 85 and R 88 independently represent hydrogen or
- R 85 and R 86 can additionally form a butadiene bridge or
- R 86 and R 87 independently of one another are hydrogen, methyl, ethyl, isopropyl, d- 25 to C 6 -alkoxy, chlorine, bromine, cyano, nitro, d- to C 4 -alkoxycarbonyl,
- Ci Mono- or Di Ci to C 4 alkylamino, Ci to C alkanoyloxy, or
- R 87 can additionally stand for l, 2,3-triazol-2-yl, which can also be benzene-fused or naphthane-fused at the 4,5-position,
- R, 8 ⁇ 9 y represents O or NH
- R 90 stands for O
- R 93 stands for O
- R 98 and R 99 represent hydrogen
- R 100 for leaving groups such as bromine, chlorine, iodine, cyano, tosylate, triflate, Ci bis
- R 101 and R 102 independently of one another for Cj to C 6 alkoxy, chlorine, bromine, iodine, Ci to C 6 alkanoyloxy, Ci to C 6 alkylthio, C 6 to Cio aryloxy, C 6 to do- Arylcarbonylamino stand.
- R 1 represents hydrogen, Ci to C 6 alkyl, C 5 to C 6 cycloalkyl, Ci to C 6 alkoxycarbonyl, aryl,
- X 1 represents NR 1 ,
- R 8S , R 88 represent hydrogen, R 86 , R 87 independently of one another represent hydrogen, methyl, Ci to C 4 alkoxy, chlorine, Ci to C 4 alkoxycarbonyl, Ci to C dialkylamino, Ci to C alkanoyloxy,
- R & 9 stands for O or NH
- R 91 represents hydrogen or Ci to C 4 alkoxycarbonyl
- R 101 represents Ci to C 6 alkoxy, Ci to C 6 alkanoyloxy, Ci to C 6 alkylthio, C 6 to Cio aryloxy.
- R 1 , R 85 - R 91 and X 1 have the meanings given above and
- the light-absorbing compounds of the formula (I) used are those with the formula (VI)
- X 1 represents NR 1 ,
- R 1 for hydrogen, Ci to C 6 alkyl, Ci to C 6 alkenyl, Ci to C 6 alkynyl, C to C cycloalkyl, C 7 to ds-aralkyl, Ci to C 6 Alkoxycarbonyl, aryl or
- Hetaryl where the hetaryl radical can contain up to 3 heteroatoms and the aryl or hetaryl radical can be substituted by up to 3 nonionic radicals,
- R 111 for hydrogen, methyl, bromine, amino, N-methylamino, dimethylamino,
- Ring A stands for a 5-9 membered partially unsaturated, aromatic or quasi-aromatic ring which can contain 1-4 heteroatoms or carbonyl groups and / or benzene or naphthane fused and / or substituted by nonionic radicals and X 6 represents cyano, d- to C 6 -alkoxycarbonyl, C 6 - to C 10 -aryloxycarbonyl or Cr to Cö-alkanoyloxycarbonyl.
- X 1 represents NR 1 ,
- R 1 is Ci to C 6 alkyl, d to C 6 alkenyl, d to C 6 alkynyl, C 4 to C 7 cycloalkyl, C 7 to C 1 aralkyl, aryl or hetaryl, the hetaryl radical can contain up to 3 heteroatoms and the aryl or hetaryl radical can contain up to
- R 111 represents hydrogen, methyl, bromine, methoxy, ethoxy,
- Ring A represents a 5-7-membered, partially unsaturated, aromatic or quasi-aromatic ring which can contain 1-4 heteroatoms or carbonyl groups and / or benzene- or naphthannellated and / or can be substituted by nonionic radicals and
- X 6 represents cyano, C ⁇ - to C 6 -alkoxycarbonyl, C 6 - to Cio-aryloxycarbonyl.
- X 1 represents NR 1 ,
- R 1 is C to C 6 alkyl, C r to C 6 alkenyl, C 5 to C 7 cycloalkyl, C 7 to C 5 aralkyl, aryl or hetaryl, the hetaryl radical having up to 3 heteroatoms may contain and the aryl or hetaryl radical may be substituted by up to 3 nonionic radicals,
- R u ' represents hydrogen
- R 112 represents cyano, Ci to C 6 alkoxycarbonyl or C 6 to Cio aryloxycarbonyl,
- Ring A stands for a 5-6-membered, partially unsaturated, aromatic or quasi-aromatic ring which may contain 1-4 heteroatoms or carbonyl groups and / or benzene or naphthane fused and / or substituted by nonionic radicals and
- X 6 represents cyano, Ci to C ö alkoxycarbonyl, C 6 to Cio-aryloxycarbonyl.
- mixtures of the compounds of the formula (I) can also be used to optimize the physical properties of the information layer.
- a write-once optical data carrier according to the invention which is written and read with the light of a blue laser, preference is given to those light-absorbing compounds whose absorption maximum ⁇ max is in the range from 350 to 470 nm and which are above the cyclization temperature T cyc in a ring-closed form have converted.
- Light- absorbing compounds with a cyclization temperature T cyc of at least 100 ° C. are preferred, particularly preferably greater than or equal to 140 ° C., in particular greater than or equal to 180 ° C.
- Preferred dyes are those in which the shift in the absorption maximum ⁇ max induced by the thermal cyclization is 25 nm or more, preferably> 35 nm, in particular> 45 nm. If there is a preferably hypsochromic shift, ⁇ max is negative. Absorption maximum in the sense of the invention is the local one
- the light-absorbing compounds preferably have a molar extinction coefficient ⁇ > 20,000 1 / mol cm, preferably
- the absorption spectra are measured, for example, in solution.
- the light-absorbing compounds described, in particular of the formula (I), guarantee a sufficiently high reflectivity (> 10%) of the optical data carrier in the blank state and a sufficiently high absorption for the thermal Degradation of the information layer in the case of selective lighting with focused light if the light wavelength is in the range from 360 to 460 nm.
- the contrast between written and unwritten points on the data carrier is realized by the change in reflectivity of the amplitude as well as the phase of the incident light by the optical properties of the information layer which have changed after thermal degradation.
- the light-absorbing compounds are preferably applied to the optical data carrier by spin coating. They can be mixed with one another or with other dyes with similar spectral properties.
- the information layer can contain additives such as binders, wetting agents, stabilizers, thinners and sensitizers and other constituents.
- the optical data storage device can carry further layers such as metal layers, dielectric layers and protective layers.
- Metal and dielectric layers and / or the protective layer serve among other things. to adjust the reflectivity and the heat balance.
- metals can be gold, silver, aluminum, etc. his.
- Dielectric layers are, for example, silicon dioxide and silicon nitride.
- Protective layers are, for example, photocurable lacquers, (pressure-sensitive) adhesive layers and protective films.
- Pressure-sensitive adhesive layers mainly consist of acrylic adhesives.
- the optical data carrier has, for example, the following layer structure (cf. FIG. 4): 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:
- a preferably transparent substrate (1) on the surface of which at least one information layer (3) which can be written on with light and which can be written on with light, preferably laser light, optionally one
- 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 invention further relates to optical data carriers according to the invention described with blue light, in particular laser light.
- the absorption band disappears almost completely in the 450 nm range and leads to a change in the absorption properties, which can be used in the wavelength range from 400 to 500 nm for optical storage and reproduction of data, e.g. a laser beam with a suitable pulse duration and pulse energy heats the dye layer above 133 ° C.
- each absorption also produces a dispersion of the refractive index above that
- Wavelength This leads to low (short-wave flank) or higher (long-wave flank) refractive indices than 1.4-1.6, which is the usual range for colorless organic materials, especially on the flanks of the absorption bands.
- the refractive index of the dye at the beginning of the temperature cycle is 1.17 and at 515 nm it is 2.17 nm.
- the decolorized dye has a refractive index in the range from 1.4 to 1.6 in the visible spectrum , This change in the refractive index can also be used for optical storage and reproduction of data, e.g.
- a laser beam with a suitable pulse duration and pulse energy heats the dye layer above 133 ° C.
- Changes in the refractive index and / or the absorption change the reflection and / or transmission properties of thin films on a transparent substrate (glass or polymer) and can therefore be changed by a laser beam which is scanned over markings written with a pulsed and focused laser beam the reflected and / or transmitted amount of light are transformed.
- the relevant film thicknesses are preferably in the range from 10 nm to 2000 nm.
- Figure 2 and Figure 3 show an example of the change in transmission of the sample described above at 405 nm during the temperature cycle.
- Figure 2 shows the Transmission curve shown over the temperature and Figure 3 over time.
- the laser wavelength is preferably in the range from 360 nm to 600 nm, particularly preferably in the range from 380 nm to 550 nm.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02706771A EP1377970A1 (de) | 2001-03-28 | 2002-03-20 | Optischer datenträger enthaltend in der informationsschicht eine cyclisierbare verbindung |
JP2002578496A JP2004525801A (ja) | 2001-03-28 | 2002-03-20 | 情報層中に環化可能な化合物を含有する光学データ記録媒体 |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10115227.2 | 2001-03-28 | ||
DE10115227A DE10115227A1 (de) | 2001-03-28 | 2001-03-28 | Optischer Datenträger enthaltend in der Informationsschicht eine lichtabsorbierende Verbindung mit mehreren chromophoren Zentren |
DE10117464.0 | 2001-04-06 | ||
DE10117464A DE10117464A1 (de) | 2001-04-06 | 2001-04-06 | Optischer Datenträger enthaltend in der Informationsschicht einen Merocyaninfarbstoff als lichtabsorbierende Verbindung |
DE2002100484 DE10200484A1 (de) | 2002-01-09 | 2002-01-09 | Optischer Datenträger enthaltend in der Imformationsschicht eine cyclisierbare Verbindung |
DE10200484.6 | 2002-01-09 |
Publications (1)
Publication Number | Publication Date |
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WO2002080163A1 true WO2002080163A1 (de) | 2002-10-10 |
Family
ID=27214367
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2002/003070 WO2002080163A1 (de) | 2001-03-28 | 2002-03-20 | Optischer datenträger enthaltend in der informationsschicht eine cyclisierbare verbindung |
Country Status (6)
Country | Link |
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US (1) | US20020197561A1 (de) |
EP (1) | EP1377970A1 (de) |
JP (1) | JP2004525801A (de) |
CN (1) | CN1513173A (de) |
TW (1) | TWI246686B (de) |
WO (1) | WO2002080163A1 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2003168243A (ja) * | 2001-11-30 | 2003-06-13 | Fuji Photo Film Co Ltd | 光情報記録媒体 |
TW200504741A (en) * | 2003-06-27 | 2005-02-01 | Ciba Sc Holding Ag | Optical recording materials having high storage density |
AU2005249031A1 (en) * | 2004-06-03 | 2005-12-15 | Clariant Finance (Bvi) Limited | Use of squaric acid dyes in optical layers for optical data recording |
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EP0347027A2 (de) * | 1988-04-21 | 1989-12-20 | Smith Kline & French Laboratories Limited | Phenylpyridon-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
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US5508143A (en) * | 1992-09-28 | 1996-04-16 | Pioneer Electronic Corporation | Optical recording medium |
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US4045229A (en) * | 1974-09-17 | 1977-08-30 | Eastman Kodak Company | Novel UV absorbing compounds and photographic elements containing UV absorbing compounds |
JPS5856239A (ja) * | 1981-09-28 | 1983-04-02 | Tdk Corp | 光記録媒体 |
US5252757A (en) * | 1987-06-05 | 1993-10-12 | Suddeutsche Zucker-Aktiengsellschaft | Dicyanoazulenyl and dicyanovinyl substituted furan |
JP2564638B2 (ja) * | 1988-12-30 | 1996-12-18 | 太陽誘電株式会社 | コンパクトディスクの製造方法 |
DE59207620D1 (de) * | 1991-10-30 | 1997-01-16 | Ciba Geigy Ag | NIR-Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
JPH10302310A (ja) * | 1997-04-25 | 1998-11-13 | Sony Corp | 光学記録媒体及び光学ディスク装置 |
TW561115B (en) * | 1999-09-08 | 2003-11-11 | Fuji Photo Film Co Ltd | Optical information recording medium |
JP2002269821A (ja) * | 2001-03-06 | 2002-09-20 | Fuji Photo Film Co Ltd | 光情報記録媒体 |
-
2002
- 2002-03-20 WO PCT/EP2002/003070 patent/WO2002080163A1/de not_active Application Discontinuation
- 2002-03-20 JP JP2002578496A patent/JP2004525801A/ja active Pending
- 2002-03-20 CN CNA028108892A patent/CN1513173A/zh active Pending
- 2002-03-20 EP EP02706771A patent/EP1377970A1/de not_active Withdrawn
- 2002-03-20 TW TW091105374A patent/TWI246686B/zh not_active IP Right Cessation
- 2002-03-20 US US10/102,582 patent/US20020197561A1/en not_active Abandoned
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DE1098125B (de) * | 1958-06-19 | 1961-01-26 | Geigy Ag J R | Verfahren zur Herstellung von fluoreszierenden Verbindungen |
CH544326A (de) * | 1969-03-24 | 1973-11-15 | Agfa Gevaert Nv | Elektrofotografisches Verfahren |
GB1471961A (en) * | 1973-04-11 | 1977-04-27 | Ciba Geigy Ag | Azo dyestuffs and process for their manufacture |
DD107033A1 (de) * | 1973-06-29 | 1974-07-12 | ||
DE2406220A1 (de) * | 1974-02-09 | 1975-08-28 | Basf Ag | Farbstoffe der benzopyranreihe |
US4837063A (en) * | 1986-07-16 | 1989-06-06 | Mitsubishi Chemical Industries Limited | Optical recording material |
EP0293651A2 (de) * | 1987-06-05 | 1988-12-07 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Dicyanvinylsubstituierte Furanderivate, Verfahren zu ihrer Herstellung und deren Verwendung |
EP0347027A2 (de) * | 1988-04-21 | 1989-12-20 | Smith Kline & French Laboratories Limited | Phenylpyridon-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
DE4329351A1 (de) * | 1992-08-31 | 1994-03-03 | Pioneer Electronic Corp | Verfahren zur Aufzeichnung, Wiedergabe und Löschung von Informationen auf und von einem optischen Aufzeichnungsmedium |
US5508143A (en) * | 1992-09-28 | 1996-04-16 | Pioneer Electronic Corporation | Optical recording medium |
Also Published As
Publication number | Publication date |
---|---|
CN1513173A (zh) | 2004-07-14 |
JP2004525801A (ja) | 2004-08-26 |
US20020197561A1 (en) | 2002-12-26 |
TWI246686B (en) | 2006-01-01 |
EP1377970A1 (de) | 2004-01-07 |
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