JP2004533509A - 電気活性フルオレン共重合体およびかかるポリマーで製造されたデバイス - Google Patents
電気活性フルオレン共重合体およびかかるポリマーで製造されたデバイス Download PDFInfo
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- JP2004533509A JP2004533509A JP2002587489A JP2002587489A JP2004533509A JP 2004533509 A JP2004533509 A JP 2004533509A JP 2002587489 A JP2002587489 A JP 2002587489A JP 2002587489 A JP2002587489 A JP 2002587489A JP 2004533509 A JP2004533509 A JP 2004533509A
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- 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
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- 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
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- 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
- H10K85/151—Copolymers
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2973—Particular cross section
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
- Y10T428/2995—Silane, siloxane or silicone coating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28831401P | 2001-05-03 | 2001-05-03 | |
| PCT/US2002/014094 WO2002090415A1 (en) | 2001-05-03 | 2002-05-03 | Electroactive fluorene copolymers and devices made with such polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004533509A true JP2004533509A (ja) | 2004-11-04 |
| JP2004533509A5 JP2004533509A5 (enExample) | 2005-12-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002587489A Pending JP2004533509A (ja) | 2001-05-03 | 2002-05-03 | 電気活性フルオレン共重合体およびかかるポリマーで製造されたデバイス |
Country Status (8)
| Country | Link |
|---|---|
| US (6) | US7074885B2 (enExample) |
| EP (1) | EP1397409A4 (enExample) |
| JP (1) | JP2004533509A (enExample) |
| KR (1) | KR20030092119A (enExample) |
| CN (1) | CN1524100A (enExample) |
| CA (1) | CA2442097A1 (enExample) |
| IL (2) | IL157931A0 (enExample) |
| WO (1) | WO2002090415A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005038634A (ja) * | 2003-07-16 | 2005-02-10 | Matsushita Electric Ind Co Ltd | 電流注入型発光素子 |
| WO2007148814A1 (ja) * | 2006-06-20 | 2007-12-27 | Sumitomo Chemical Company, Limited | 縮合環含有高分子電解質およびその用途 |
| JP2008027903A (ja) * | 2006-06-20 | 2008-02-07 | Sumitomo Chemical Co Ltd | 縮合環含有高分子電解質およびその用途 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG100772A1 (en) * | 2000-12-06 | 2003-12-26 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light-emiting device using the same |
| US20030044680A1 (en) * | 2001-08-24 | 2003-03-06 | Im&T Research, Inc. | Polymer materials for use in an electrode |
| US7138483B2 (en) | 2003-02-12 | 2006-11-21 | E.I. Du Pont De Nemours And Company | Monomers, conjugated polymers and electronic devices using such polymers |
| EP1486551B1 (en) * | 2003-06-13 | 2016-03-16 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting element and light emitting device |
| TW201235442A (en) * | 2003-12-12 | 2012-09-01 | Sumitomo Chemical Co | Polymer and light-emitting element using said polymer |
| US7473577B2 (en) * | 2006-08-11 | 2009-01-06 | International Business Machines Corporation | Integrated chip carrier with compliant interconnect |
| US20080151844A1 (en) * | 2006-12-20 | 2008-06-26 | Manish Tiwari | Wireless access point authentication system and method |
| KR101646770B1 (ko) * | 2008-03-31 | 2016-08-08 | 카운슬 오브 사이언티픽 앤드 인더스트리얼 리서치 | 신규의 공여체-수용체 플루오렌 스캐폴드, 이의 제조방법 및 용도 |
| KR101156630B1 (ko) | 2009-02-27 | 2012-06-15 | 경상대학교산학협력단 | 디알콕시치환체를 갖는 나프탈렌 교대 공중합체와 이를 이용한 유기전자소자 |
| KR101581991B1 (ko) * | 2009-04-24 | 2015-12-31 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전기 전도성 중합체 조성물 및 그로부터 제조된 필름 |
| JP2012527518A (ja) * | 2009-05-18 | 2012-11-08 | ザ、リージェンツ、オブ、ザ、ユニバーシティ、オブ、カリフォルニア | リチウムイオン電池電極用の導電性ポリマーバインダ |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2527618A1 (fr) * | 1982-05-25 | 1983-12-02 | Thomson Csf | Polymeres contenant des heterocycles et des noyaux aromatiques et materiaux organiques conducteurs formes a partir de ces polymeres |
| FR2603288B1 (fr) | 1986-09-03 | 1988-12-09 | France Etat | Polyfluorenes 9,9'-disubstitues, leur procede de preparation et leurs applications en electro-optique et electrochimie |
| US5668118A (en) * | 1992-07-24 | 1997-09-16 | Cavalier Pharmaceuticals | Method of synthesis of 2-O-desulfated Heparin and use thereof for inhibition of elastase and Cathepspin G |
| DE4331401A1 (de) * | 1993-09-15 | 1995-03-16 | Hoechst Ag | Verwendung von Polymeren mit isolierten Chromophoren als Elektrolumineszenzmaterialen |
| DE4436773A1 (de) * | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
| TW334474B (en) * | 1995-02-01 | 1998-06-21 | Sumitomo Kagaku Kk | Method for making a polymeric fluorescent substrate and organic electrolumninescent element |
| CN1229415C (zh) * | 1995-07-28 | 2005-11-30 | 陶氏环球技术公司 | 2,7－芳基－9－取代的芴和9－取代的芴的低聚物和聚合物 |
| US5708130A (en) * | 1995-07-28 | 1998-01-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
| EP0848739A1 (de) * | 1995-09-04 | 1998-06-24 | Hoechst Research & Technology Deutschland GmbH & Co. KG | Polymere mit triarylamin-einheiten als elektrolumineszenzmaterialien |
| US5763636A (en) * | 1995-10-12 | 1998-06-09 | Hoechst Aktiengesellschaft | Polymers containing spiro atoms and methods of using the same as electroluminescence materials |
| WO1997033323A1 (en) * | 1996-03-04 | 1997-09-12 | Uniax Corporation | Polyfluorenes as materials for photoluminescence and electroluminescence |
| KR0176331B1 (ko) | 1996-05-16 | 1999-04-01 | 박원훈 | 전계 발광 소자용 플로렌계 교대 공중합체 및 이를 발광재료로 사용한 전계 발광 소자 |
| DE19642149A1 (de) * | 1996-10-12 | 1998-04-23 | Telefunken Microelectron | System zur Datenübertragung |
| KR0176336B1 (ko) | 1996-12-31 | 1999-04-01 | 박원훈 | 아세틸렌기를 함유한 플로렌계 교대 공중합체 및 이를 이용한 전계발광소자 |
| WO1998033836A1 (en) | 1997-01-30 | 1998-08-06 | Jsr Corporation | Process for producing phenylene-containing polymer and film-forming material |
| US6309763B1 (en) * | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
| US5998045A (en) * | 1997-07-03 | 1999-12-07 | International Business Machines Corporation | Polymeric light-emitting device |
| US5777070A (en) * | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
| KR100245841B1 (ko) * | 1997-12-29 | 2000-03-02 | 박호군 | 다중 발광단을 함유한 플로렌계 복합 교대 공중합체 및 이를 이용한 전계 발광소자 |
| KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
| WO1999054943A1 (en) | 1998-04-21 | 1999-10-28 | The Dow Chemical Company | Organic electroluminescent devices with improved stability in air |
| DE19846766A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
| DE19846768A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere enthaltend 2,7-Fluorenyleinheiten mit verbesserten Eigenschaften |
| US6204515B1 (en) * | 1999-01-15 | 2001-03-20 | The Dow Chemical Company | Semiconducting polymer field effect transistor |
| EP1155096B1 (en) | 1999-02-04 | 2005-03-09 | Dow Global Technologies Inc. | Fluorene copolymers and devices made therefrom |
| ATE370176T1 (de) | 1999-03-05 | 2007-09-15 | Cambridge Display Tech Ltd | Polymerherstellung |
| US6363083B1 (en) * | 1999-03-12 | 2002-03-26 | Otis Elevator Company | Bilevel node identifiers in control area network (CAN) protocol |
| AU3524800A (en) | 1999-03-12 | 2000-09-28 | B.F. Goodrich Company, The | Polycyclic polymers containing pendant cyclic anhydride groups |
| US6312811B1 (en) | 1999-07-08 | 2001-11-06 | Essilor International Compagnie Generale D'optique | Photochromic naphtho [2,1-b]pyran compounds containing bithienyl or terthienyl substituents, process for their manufacture, and photochromic materials and articles obtained |
| GB9917356D0 (en) | 1999-07-24 | 1999-09-22 | Univ Cambridge Tech | Aromatic monomers and polymers for optoelectronic devices |
| AU1540001A (en) * | 1999-12-09 | 2001-06-18 | Cambridge Display Technology Limited | Fluorene-perylene copolymers and uses thereof |
| WO2001077203A2 (en) | 2000-04-11 | 2001-10-18 | Dupont Displays, Inc. | Soluble poly(aryl-oxadiazole) conjugated polymers |
| EP1149827B1 (en) | 2000-04-26 | 2003-12-10 | Sony International (Europe) GmbH | End-capped polyfluorenes, films and devices based thereon |
| JP2004532291A (ja) | 2001-02-21 | 2004-10-21 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ポリマー |
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2002
- 2002-05-02 US US10/137,898 patent/US7074885B2/en not_active Expired - Fee Related
- 2002-05-03 IL IL15793102A patent/IL157931A0/xx unknown
- 2002-05-03 WO PCT/US2002/014094 patent/WO2002090415A1/en not_active Ceased
- 2002-05-03 EP EP02731655A patent/EP1397409A4/en not_active Withdrawn
- 2002-05-03 JP JP2002587489A patent/JP2004533509A/ja active Pending
- 2002-05-03 CA CA002442097A patent/CA2442097A1/en not_active Abandoned
- 2002-05-03 IL IL15826502A patent/IL158265A0/xx unknown
- 2002-05-03 KR KR10-2003-7014230A patent/KR20030092119A/ko not_active Withdrawn
- 2002-05-03 CN CNA028093356A patent/CN1524100A/zh active Pending
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2004
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- 2004-03-25 US US10/809,142 patent/US7220820B2/en not_active Expired - Lifetime
- 2004-03-25 US US10/809,169 patent/US7211643B2/en not_active Expired - Lifetime
- 2004-03-25 US US10/809,737 patent/US7230070B2/en not_active Expired - Fee Related
- 2004-09-14 US US10/940,566 patent/US7183366B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005038634A (ja) * | 2003-07-16 | 2005-02-10 | Matsushita Electric Ind Co Ltd | 電流注入型発光素子 |
| WO2007148814A1 (ja) * | 2006-06-20 | 2007-12-27 | Sumitomo Chemical Company, Limited | 縮合環含有高分子電解質およびその用途 |
| JP2008027903A (ja) * | 2006-06-20 | 2008-02-07 | Sumitomo Chemical Co Ltd | 縮合環含有高分子電解質およびその用途 |
| GB2453082A (en) * | 2006-06-20 | 2009-03-25 | Sumitomo Chemical Co | Fused ring-containing polymer electrolyte and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050049388A1 (en) | 2005-03-03 |
| KR20030092119A (ko) | 2003-12-03 |
| US20030027934A1 (en) | 2003-02-06 |
| US7220820B2 (en) | 2007-05-22 |
| IL157931A0 (en) | 2004-03-28 |
| US7183366B2 (en) | 2007-02-27 |
| US7214763B2 (en) | 2007-05-08 |
| US20040181021A1 (en) | 2004-09-16 |
| US7230070B2 (en) | 2007-06-12 |
| US7074885B2 (en) | 2006-07-11 |
| US20040181019A1 (en) | 2004-09-16 |
| EP1397409A4 (en) | 2005-03-16 |
| US20040186267A1 (en) | 2004-09-23 |
| WO2002090415A1 (en) | 2002-11-14 |
| US20040181020A1 (en) | 2004-09-16 |
| CA2442097A1 (en) | 2002-11-14 |
| EP1397409A1 (en) | 2004-03-17 |
| US7211643B2 (en) | 2007-05-01 |
| IL158265A0 (en) | 2004-05-12 |
| CN1524100A (zh) | 2004-08-25 |
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