EP0910930A1 - Elektrolumineszierende anordnungen unter verwendung von blendsystemen - Google Patents
Elektrolumineszierende anordnungen unter verwendung von blendsystemenInfo
- Publication number
- EP0910930A1 EP0910930A1 EP97933643A EP97933643A EP0910930A1 EP 0910930 A1 EP0910930 A1 EP 0910930A1 EP 97933643 A EP97933643 A EP 97933643A EP 97933643 A EP97933643 A EP 97933643A EP 0910930 A1 EP0910930 A1 EP 0910930A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- electroluminescent
- hole
- zone
- transporting
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 12
- 229940126062 Compound A Drugs 0.000 claims abstract description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims abstract description 4
- -1 aromatic tertiary amino compound Chemical class 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 9
- 239000004020 conductor Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical class 0.000 claims description 4
- 230000003595 spectral effect Effects 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 150000004880 oxines Chemical class 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 229960003540 oxyquinoline Drugs 0.000 claims description 2
- 239000013034 phenoxy resin Substances 0.000 claims description 2
- 229920006287 phenoxy resin Polymers 0.000 claims description 2
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical class OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 claims description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- 150000002910 rare earth metals Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims 3
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical compound NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 claims 1
- HJSRGOVAIOPERP-UHFFFAOYSA-N 5-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=CC2=N1 HJSRGOVAIOPERP-UHFFFAOYSA-N 0.000 claims 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims 1
- 239000004713 Cyclic olefin copolymer Substances 0.000 claims 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- XAIDAKZDWHHFGM-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al].C1=CN=C2C(O)=CC=CC2=C1 XAIDAKZDWHHFGM-UHFFFAOYSA-N 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- 229920005596 polymer binder Polymers 0.000 claims 1
- 239000002491 polymer binding agent Substances 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 239000002356 single layer Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 238000001429 visible spectrum Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000010345 tape casting Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- JOHWZFAFYMBKLF-UHFFFAOYSA-N 2,6,9,10-tetra(propan-2-yloxy)anthracene Chemical compound C1=C(OC(C)C)C=CC2=C(OC(C)C)C3=CC(OC(C)C)=CC=C3C(OC(C)C)=C21 JOHWZFAFYMBKLF-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
- H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- An electroluminescent (EL) arrangement is characterized in that it emits light under the application of an electrical voltage under current flow.
- LEDs light emitting diodes
- the emission of light is caused by the fact that positive charges ("holes”, holes) and negative charges (“electrons", electrons) recombine while emitting light
- Polymers such as poly- (p-phenylene) and poly- (p-phenylenevinylne (PPV)) are also described as electroluminescent polymers G Leising et al, Adv Mater 4 (1992) No. 1, Fnend et al, J Che Soc, Chem Commun 32 (1992),
- EP-A 0 294 061 presents an optical modulator based on polyacetylene
- the organic EL arrangements usually contain one or more layers of organic charge transport compounds.
- the basic structure in the order of the layers is as follows
- Layers 3 to 7 represent the electroluminescent element
- an EL arrangement consists of two electrodes, between which there is an organic layer that includes all functions - including that of the emission of light - such systems are described in 7 B in the application WO 90/13148 on the basis of poly (p-phenylene vinyl)
- Multi-layer systems can be built up by vapor deposition processes, in which the layers are applied successively from the gas phase, or by casting processes. Casting processes are preferred due to the higher process speed chains. However, the batching process can already be applied
- the object of the present invention is to provide electroluminescent arrangements with high luminance, the mixture to be applied being pourable It has been found that electroluminescent arrangements which contain the below-mentioned blend system meet these requirements.
- zone is also to be equated with layer
- the present invention relates to electroluminescent arrangements comprising a substrate, an anode, an electroluminescent element and a cathode, wherein at least one of the two electrodes is transparent in the visible spectral range and can contain the electroluminescent element in order
- a hole-injecting zone, hole-transporting zone, electroluminescent zone, electron-transporting zone and / or an electron-injecting zone characterized in that the hole-injecting and / or hole-transporting zone is an optionally substituted T ⁇ s-l, 3,5- (aminophenyl) benzene compound A or a mixture thereof and the electroluminescent element is optionally a further functionalized compound from the group of the hole-transporting materials, a luminescent material B and optionally
- the hole-injecting and hole-transporting zone can contain, in addition to component A, one or more further hole-transporting compounds, at least one zone being present, individual zones being omitted and the existing zone (s) being able to take on several tasks
- a zone can perform several tasks, that is to say that a zone can contain, for example, hole-injecting, hole-transporting, electroluminescent, electron-injecting and / or electron-transporting substances
- the electroluminescent element may further contain one or more transparent polymeric binders C.
- the optionally substituted 1 ⁇ s- l, 3,5- (aminophenyl) benzene compound A represents an aromatic tertiary amino compound of the general formula (I)
- R represents hydrogen, optionally substituted alkyl or halogen
- R 1 and R 4 independently of one another represent optionally substituted C, -C 10 alkyl, alkoxycarbonyl-substituted C, -C 10 alkyl, or optionally substituted aryl, aralkyl or cycloalkyl
- R 'and R 4 independently of one another preferably represent C ] -C 6 -alkyl, in particular methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, C ] -C 4 -alkoxcarbonyl -C ] -C f) alkyl, such as methoxy, ethoxy, Pi opoxy, butoxycarbonyl-C
- R 1 and R 4 are particularly preferably independently of one another unsubstituted phenyl or naphthyl or in each case one to three times by methyl, ethyl, n- or isopropyl. Methoxy, ethoxy, n- and / or iso-propoxy substituted phenyl or naphthyl
- R ⁇ is preferably hydrogen, C j -C ⁇ alkyl, such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, or chlorine
- T ⁇ s-nitrophenyl compound can be converted into the T ⁇ s-aminophenyl compound, for example by generally known catalytic hydrogenation, for example in the presence of Ranev nickel (Houben-Weyl 4 / IC, 14 -102, Ullmann (4) ü, 135- 148)
- Ranev nickel Houben-Weyl 4 / IC, 14 -102, Ullmann (4) ü, 135- 1478
- the amino compound is reacted in a generally known manner with substituted halogenobenzenes
- hole conductors for example in the form of a mixture with component A, can optionally be used to build up the electroluminescent element.
- it can be one or more compounds of the formula (I), which also comprises mixtures of isomeres on the other hand also with mixtures of hole-transporting compounds
- the compounds can be used in any ratio between 0 and 100% by weight (based on mixture A)). In a preferred embodiment, 1 to 99% by weight and 99 to 1% by weight , particularly preferably 5 to 95% by weight and 95 to 5% by weight used. In a further preferred embodiment, 30 to 70% by weight or 70 to 30% by weight are used
- Anthracene compounds for example 2,6,9, 10-tetraisopropoxyanthracene, oxadiazole compounds, for example 2,5-B ⁇ s (4-dimethylamino-nophenyl) -1, 3,4-oxadiazole, t ⁇ phenylamine compounds, for example BN, N '-D ⁇ phenyl-N, N'-d ⁇ (3-methylphenyl) - l, l' -b ⁇ phenyl-4,4'-d ⁇ - amine, aromatic tertiary amines, for example N-phenylcarbazole, N-isopropyl-carbazo!
- T ⁇ phenylamine compounds and / or aromatic tertiary amines are preferred, the compounds mentioned by way of example being particularly preferred Materials which have hole-conducting properties and can be used as mixing partners for component A are, for example
- the binder C) stands for polymers and / or copolymers such as polycarbonates, polyester carbonates, copolymers of styrene such as SAN or styrene acrylates, polysulfones, polymers based on monomers containing vinyl groups such as poly (meth) acrylates, polyvinylpyrrolidone, polyvinylcarbazole, vinyl acetate and vinyl alcohol polymers and copolymers, polyolefms, cychsche Olelfincopolvmere, phenoxy resins, etc. Mixtures of different polymers can also be used.
- the polymeric binders C) have molecular weights of 10,000 to 2,000,000 g / mol, are soluble and film-forming and are in the visible spectral range transparent They are described, for example, in Encyclopedia of Polymer Science and Engineering, 2 n Ed at A Wiley-Intersciencepublication They are usually used in an amount of up to 95, preferably up to 80, by weight, based on the total weight of A) and B), used
- Component B) represents a compound of the general formula (II)
- n is a number from 1 to 3 and is / independently in both forms stands for atoms that complete a nucleus that consists of at least 2 condensed rings
- the metal can be a mono-, di- or trivalent metal, for example lithium, sodium, potassium, magnesium, calcium, boron or aluminum
- Z completes a heterocytic part of the molecule which consists of at least two condensed rings, one of which is an azole or azine ring, it being possible for further additional ahphatic or aromatic rings to be attached to the two rings which are close together
- Suitable examples of component B) are the oxine complexes (8-hydroxyquinoline complexes) of Al ⁇ 1 , Mg 2 ', In "", Ga ⁇ Zn 2 ⁇ Be 2 1 , Li', Ca 2 'Na * or Alum ⁇ n ⁇ umt ⁇ s (5-methyloxin) R and Gall ⁇ umt ⁇ s (5-chIoro-ch ⁇ nol ⁇ n) Complexes with rare earth metals can also be used
- One or more compounds of component B) can be used
- the compounds or the oxine complexes according to component B are general are known and can be produced by known processes (see, for example, US Pat. No. 4,769,292)
- the electroluminescent arrangements according to the invention are characterized in that they have a light-emitting layer which contains a mixture of components A) and B) in optionally a transparent binder C).
- the weight ratio of A) and B) to one another is variably adjustable.
- the proportion by weight of the sum of the proportions by weight of A) and B) in the polymeric binder is in the range from 0.2 to 98% by weight, preferably from 2 to 95% by weight, particularly preferably from 10 to 90% by weight, very particularly preferably 10 to
- the weight ratio AB of components A and B is between 0.05 and 20, preferably 0.2 and 10 and particularly preferably between 0.3 and 8, in particular 0.3 to 7.
- Components A) and B) can either consist of one component or a mixture of components of any composition
- components A), B) and optionally C) are dissolved in a suitable solvent and applied to a suitable base by pouring, knife coating or spin coating.
- a suitable solvent for example, glass or a plastic material which is transparent
- the electrode is provided as a plastic material, for example a film made of polycarbonate
- Polyesters such as polyethylene terephthalate or polyethylene naphthalate, polysulfone or polyimide can be used
- Metalloxides e.g. indium tin oxide (ITO), tin oxide (NESA), zinc oxide, doped tin oxide, doped zinc oxide, etc,
- the metal oxide and semi-transparent metal film electrodes are made by Techniques such as vapor deposition, sputtering, plating, etc., applied in a thin layer.
- the conductive polymer films are applied from the solution using techniques such as spin coating casting, knife coating, etc.
- the thickness of the transparent electrode is 3 nm to approximately several ⁇ m, preferably 10 nm to 500 nm
- the electroluminescent layer is applied directly to the transparent electrode or to a charge-transporting layer which may be present as a thin film.
- the thickness of the film is 10 to 500 nm, preferably 20 to 400 nm, particularly preferably 50 to 250 nm
- Another charge-transporting layer can be applied to the electroluminescent layer
- EP-A 532 798 A compilation of suitable charge-transporting intermediate layers, which can be hole- and / or electron-conducting materials, which may be present as a blend in polymeric or low molecular weight form, is listed in EP-A 532 798. Specially substituted polythiophenes are particularly suitable Which have hole-transposing properties are described, for example, in EP-A 686 662
- the content of low-molecular hole conductor in a polymeric binder can be varied in the range from 2 to 97% by weight, the content is preferably 5 to 95% by weight, particularly preferably 10 to 90% by weight, in particular 10 to 85
- the hole-injecting or hole-conducting zones can be deposited using various methods
- Film-guiding hole conductors can also be used in pure form (100% ⁇ g). If appropriate, the hole-injecting or hole-conducting zone can also contain portions of an electroluminescent substance
- Blends that consist exclusively of low molecular weight compounds can be evaporated, soluble and film-forming blends, which in addition to low molecular weight compounds can also contain a bond C) (not necessarily), can be deposited from a solution, for example by means of spin-coating casting, knife coating It is also possible to apply emitting and / or electron-conducting substances in a separate layer to the hole-conducting layer with component A. An emitting substance can also be added to the layer containing compound A ("dopant") and an electron-conducting substance can also be applied Electroluminescent substance can also be added to the electron-injecting or electron-conducting layer
- the content of low-molecular electron conductors in the polymeric binder can be varied in the range from 2 to 95% by weight, the content is preferably 5 to 90% by weight, particularly preferably 10 to 85% by weight.
- Film-forming electron conductors can also be used in pure form (100% ) are used
- the counterelectrode consists of a conductive substance that can be transparent.
- metals eg Al, Au, Ag, Mg, In, etc or alloys and oxides thereof are suitable, which can be applied by techniques such as sputtering, platinum plating
- the arrangement according to the invention is by two electrical leads (z
- the arrangements When a direct voltage is applied in the range from 0.1 to 100 volts, the arrangements emit light of the wavelength from 200 to 2000 nm. They show photoluminescence in the range from 200 to 2000 nm
- Electroluminescent arrangement based on a blend system
- a 1% solution consists of 1 part by weight A, 1 part by weight B and 4 Weight points C in dichloroethane is distributed with a commercial spin coater at a speed of 400 / min on a ITO coated glass plate (Baltracon 255 from Balzers)
- the layer thickness is 100 nm
- the arrangement After contacting and application of an electric field, the arrangement shows visually recognizable electroluminescence in the green spectral range from approximately 7 V.
- the brightness is 355 cd / m 2 at a current of 19 mA / cm 2 and a voltage of 16 V
- Electroluminescent arrangement based on a blend system, consisting of
- Example I Layer production and contacting are carried out as in Example I.
- the brightness is at an applied voltage of 16 V and a current of
- Example 4 Layer production and contacting are carried out as in Example 1.
- the brightness is 20 V with an applied voltage and a current of 18 7 mA / cm 2 3 10 cd / m 2
- Example 4
- Electroluminescent arrangement based on a blend system, consisting of
- Example 1 Layer production and contacting are carried out as in Example 1.
- the brightness is 1 5 V with an applied voltage and a current of
- the layer thickness is approx. 60 nm
- a MgAg alloy in a ratio of 10 1 is applied as the counter electrode by thermal code position.
- the system emits green light.
- the diode emits green light
- a 1.5% solution of A) in chloroform is distributed with a commercially available spin coater at a speed of 1000 rpm onto an ITO-coated glass plate (Baltracon 255 from Balzers).
- the layer is 120 nm
- Al is applied as the counter electrode by thermal evaporation
- electroluminescence After contacting and application of an electrical voltage, electroluminescence can be detected from 8 V with a Si photodiode. At a voltage of 20 V a current of 25 mA / cm 2 flows and the luminance is 2 cd / m 2. The color of the electroluminescence is blue
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE19627070 | 1996-07-05 | ||
DE19627070A DE19627070A1 (de) | 1996-07-05 | 1996-07-05 | Elektrolumineszierende Anordnungen unter Verwendung von Blendsystemen |
PCT/EP1997/003439 WO1998002018A1 (de) | 1996-07-05 | 1997-07-01 | Elektrolumineszierende anordnungen unter verwendung von blendsystemen |
Publications (1)
Publication Number | Publication Date |
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EP0910930A1 true EP0910930A1 (de) | 1999-04-28 |
Family
ID=7798998
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97933643A Withdrawn EP0910930A1 (de) | 1996-07-05 | 1997-07-01 | Elektrolumineszierende anordnungen unter verwendung von blendsystemen |
Country Status (7)
Country | Link |
---|---|
US (1) | US6541128B2 (ko) |
EP (1) | EP0910930A1 (ko) |
JP (1) | JP2000514591A (ko) |
KR (1) | KR20000022457A (ko) |
AU (1) | AU3692497A (ko) |
DE (1) | DE19627070A1 (ko) |
WO (1) | WO1998002018A1 (ko) |
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GB9712483D0 (en) | 1997-06-17 | 1997-08-20 | Kathirgamanathan Poopathy | Fabrication of light emitting devices from chelates of transition metals, lanthanides and actinides |
DE19803889A1 (de) | 1998-01-31 | 1999-08-05 | Bosch Gmbh Robert | Elektrolumineszierende Anordnung unter Verwendung von dotierten Blendsystemen |
GB9826406D0 (en) * | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Quinolates |
GB9805476D0 (en) * | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
DE19812259A1 (de) * | 1998-03-20 | 1999-10-21 | Bayer Ag | EL-Anordnung auf Basis von tert.-Aminen, in Alkohol löslichen Alq3-Derivaten bzw. Mischungen und polymeren Bindern |
DE19812258A1 (de) * | 1998-03-20 | 1999-09-23 | Bayer Ag | Elektrolumineszierende Anordnungen unter Verwendung von Blendsystemen |
DE19825737A1 (de) * | 1998-06-09 | 1999-12-16 | Bayer Ag | Elektrolumineszierende Anordnungen mit N-Alkyl-2,2'-imino-bis-(8-hydroxychinolin)-Metallkomplexen |
DE19829948A1 (de) * | 1998-07-04 | 2000-01-05 | Bayer Ag | Elektrolumineszierende Anordnung unter Verwendung von Azomethin-Metallkomplexen |
US6316130B1 (en) | 1998-07-04 | 2001-11-13 | Bayer Aktiengesellschaft | Electroluminescent assemblies using azomethine-metal complexes |
DE19829947A1 (de) | 1998-07-04 | 2000-01-05 | Bayer Ag | Elektrolumineszierende Anordnungen mit Bor-Chelaten |
DE19839946A1 (de) * | 1998-09-02 | 2000-03-09 | Bayer Ag | Elektrolumineszierende Anordnungen mit mehrkernigen Metallkomplexen |
DE19839947A1 (de) * | 1998-09-02 | 2000-03-09 | Bayer Ag | Elektrolumineszierende Anordnungen mit Thiophencarboxylat-Metallkomplexen |
DE19839948A1 (de) * | 1998-09-02 | 2000-03-09 | Bayer Ag | Elektrolumineszierende Anordnungen mit Metallkomplexen mit angeknüpften Fluoreszenzfarbstoffen |
GB9823761D0 (en) | 1998-11-02 | 1998-12-23 | South Bank Univ Entpr Ltd | Novel electroluminescent materials |
GB9826405D0 (en) | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Method for forming films or layers |
GB9826407D0 (en) | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Novel electroluminescent materials |
GB9901971D0 (en) | 1999-02-01 | 1999-03-17 | South Bank Univ Entpr Ltd | Electroluminescent material |
GB0109755D0 (en) | 2001-04-20 | 2001-06-13 | Elam T Ltd | Devices incorporating mixed metal organic complexes |
TWI303533B (en) | 2001-06-15 | 2008-11-21 | Oled T Ltd | Electroluminescent devices |
GB0116644D0 (en) | 2001-07-09 | 2001-08-29 | Elam T Ltd | Electroluminescent materials and devices |
WO2003014256A1 (en) | 2001-08-04 | 2003-02-20 | Elam-T Limited | Electroluminescent device |
KR100474891B1 (ko) * | 2001-12-20 | 2005-03-08 | 엘지전자 주식회사 | 유기 el 디스플레이 소자 |
US7347957B2 (en) * | 2003-07-10 | 2008-03-25 | Sipix Imaging, Inc. | Methods and compositions for improved electrophoretic display performance |
US8547628B2 (en) | 2002-07-17 | 2013-10-01 | Sipix Imaging, Inc. | Methods and compositions for improved electrophoretic display performance |
US20060255322A1 (en) * | 2002-07-17 | 2006-11-16 | Wu Zarng-Arh G | Methods and compositions for improved electrophoretic display performance |
US8440324B2 (en) * | 2005-12-27 | 2013-05-14 | E I Du Pont De Nemours And Company | Compositions comprising novel copolymers and electronic devices made with such compositions |
EP2412699A1 (en) * | 2005-12-28 | 2012-02-01 | E.I. Du Pont De Nemours And Company | Compositions comprising novel compounds and electronic devices made with such compositions |
JP5298460B2 (ja) * | 2006-06-08 | 2013-09-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
WO2009079004A1 (en) * | 2007-12-18 | 2009-06-25 | Lumimove, Inc., Dba Crosslink | Flexible electroluminescent devices and systems |
EP2376593A4 (en) * | 2008-12-12 | 2013-03-06 | Du Pont | PHOTO-ACTIVE COMPOSITION AND ELECTRONIC DEVICE USING THE COMPOSITION |
US8937300B2 (en) | 2009-10-19 | 2015-01-20 | E I Du Pont De Nemours And Company | Triarylamine compounds for use in organic light-emitting diodes |
EP2491003A4 (en) | 2009-10-19 | 2015-06-03 | Du Pont | TRIARYLAMINE COMPOUNDS FOR ELECTRONIC APPLICATIONS |
US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
WO2016060959A1 (en) | 2014-10-17 | 2016-04-21 | E Ink California, Llc | Composition and process for sealing microcells |
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US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
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GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
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JP3069139B2 (ja) | 1990-03-16 | 2000-07-24 | 旭化成工業株式会社 | 分散型電界発光素子 |
GB9018698D0 (en) | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
US5408109A (en) | 1991-02-27 | 1995-04-18 | The Regents Of The University Of California | Visible light emitting diodes fabricated from soluble semiconducting polymers |
JPH0790256A (ja) | 1993-09-22 | 1995-04-04 | Pioneer Electron Corp | 有機エレクトロルミネッセンス素子 |
DE19507413A1 (de) | 1994-05-06 | 1995-11-09 | Bayer Ag | Leitfähige Beschichtungen |
ATE228545T1 (de) | 1994-05-06 | 2002-12-15 | Bayer Ag | Leitfähige beschichtungen |
US5554450A (en) | 1995-03-08 | 1996-09-10 | Eastman Kodak Company | Organic electroluminescent devices with high thermal stability |
EP0766498B1 (en) * | 1995-09-29 | 2001-01-24 | Eastman Kodak Company | Organic electroluminescent devices with high operational stability |
DE19812259A1 (de) * | 1998-03-20 | 1999-10-21 | Bayer Ag | EL-Anordnung auf Basis von tert.-Aminen, in Alkohol löslichen Alq3-Derivaten bzw. Mischungen und polymeren Bindern |
-
1996
- 1996-07-05 DE DE19627070A patent/DE19627070A1/de not_active Withdrawn
-
1997
- 1997-07-01 JP JP10504732A patent/JP2000514591A/ja active Pending
- 1997-07-01 AU AU36924/97A patent/AU3692497A/en not_active Abandoned
- 1997-07-01 EP EP97933643A patent/EP0910930A1/de not_active Withdrawn
- 1997-07-01 KR KR1019980710893A patent/KR20000022457A/ko not_active Application Discontinuation
- 1997-07-01 WO PCT/EP1997/003439 patent/WO1998002018A1/de not_active Application Discontinuation
- 1997-07-01 US US09/214,316 patent/US6541128B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
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See references of WO9802018A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU3692497A (en) | 1998-02-02 |
US6541128B2 (en) | 2003-04-01 |
WO1998002018A1 (de) | 1998-01-15 |
KR20000022457A (ko) | 2000-04-25 |
DE19627070A1 (de) | 1998-01-08 |
US20020136921A1 (en) | 2002-09-26 |
JP2000514591A (ja) | 2000-10-31 |
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