JP2009501259A - 光−電気装置の導電性ポリマー組成物 - Google Patents
光−電気装置の導電性ポリマー組成物 Download PDFInfo
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- JP2009501259A JP2009501259A JP2008520961A JP2008520961A JP2009501259A JP 2009501259 A JP2009501259 A JP 2009501259A JP 2008520961 A JP2008520961 A JP 2008520961A JP 2008520961 A JP2008520961 A JP 2008520961A JP 2009501259 A JP2009501259 A JP 2009501259A
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
-
- 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
-
- 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
-
- 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
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; 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
- H10K85/10—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
-
- 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
-
- 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]
- H10K50/17—Carrier injection layers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0514476.1A GB0514476D0 (en) | 2005-07-14 | 2005-07-14 | Conductive polymer compositions in opto-electrical devices |
| PCT/GB2006/002643 WO2007007117A1 (en) | 2005-07-14 | 2006-07-14 | Conductive polymer compositions in opto-electrical devices |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009501259A true JP2009501259A (ja) | 2009-01-15 |
| JP2009501259A5 JP2009501259A5 (enExample) | 2011-06-16 |
Family
ID=34897215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008520961A Pending JP2009501259A (ja) | 2005-07-14 | 2006-07-14 | 光−電気装置の導電性ポリマー組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8308987B2 (enExample) |
| JP (1) | JP2009501259A (enExample) |
| KR (1) | KR101296040B1 (enExample) |
| CN (1) | CN101223236B (enExample) |
| DE (1) | DE112006001828B4 (enExample) |
| GB (2) | GB0514476D0 (enExample) |
| WO (1) | WO2007007117A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007327058A (ja) * | 2006-06-07 | 2007-12-20 | Samsung Sdi Co Ltd | 導電性高分子組成物およびこれを採用した電子素子 |
| JP2008211135A (ja) * | 2007-02-28 | 2008-09-11 | Sumitomo Chemical Co Ltd | 有機発光素子およびその製造方法 |
| JP2009239279A (ja) * | 2008-03-07 | 2009-10-15 | Sumitomo Chemical Co Ltd | 積層構造体 |
| JP2012216821A (ja) * | 2011-03-28 | 2012-11-08 | Sumitomo Chemical Co Ltd | 電子デバイス、高分子化合物 |
| JP2013243280A (ja) * | 2012-05-22 | 2013-12-05 | Hitachi Chemical Co Ltd | 有機エレクトロニクス材料、インク組成物、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、及び光電変換素子 |
| WO2015159932A1 (ja) * | 2014-04-18 | 2015-10-22 | 住友化学株式会社 | 発光素子およびそれに用いる高分子化合物 |
| KR20160029684A (ko) * | 2014-09-05 | 2016-03-15 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 도전성 중합체 복합체 및 기판 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2143768A1 (en) * | 2008-07-11 | 2010-01-13 | Acreo AB | Waterbased casting or printing composition |
| DE102009014856A1 (de) * | 2009-03-30 | 2010-10-07 | H.C. Starck Clevios Gmbh | Polymerbeschichtungen mit verbesserter UV- und Temperaturstabilität |
| WO2011017341A2 (en) * | 2009-08-03 | 2011-02-10 | The Johns Hopkins University | Ladder-type oligo-p-phenylene-containing copolymers with high open-circuit voltages and ambient photovoltaic activity |
| KR101305869B1 (ko) * | 2011-10-12 | 2013-09-09 | 포항공과대학교 산학협력단 | 단순화된 유기 발광 소자 및 이의 제조 방법 |
| US10020089B2 (en) * | 2014-09-05 | 2018-07-10 | Shin-Etsu Chemical Co., Ltd. | Conductive polymer composite and substrate |
| CN113185532A (zh) * | 2017-11-27 | 2021-07-30 | 北京夏禾科技有限公司 | 含噻吩三芳胺化合物 |
| CN116322111A (zh) * | 2021-12-21 | 2023-06-23 | Tcl科技集团股份有限公司 | 组合物、组合物的制备方法、发光器件及显示装置 |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539507A (en) * | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| US5150006A (en) * | 1991-08-01 | 1992-09-22 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (II) |
| JP3490727B2 (ja) * | 1991-11-28 | 2004-01-26 | 三洋電機株式会社 | 電界発光素子 |
| EP0700917B1 (en) * | 1994-09-12 | 2002-05-08 | Motorola, Inc. | Light emitting devices comprising organometallic complexes |
| DE4436773A1 (de) | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
| DE69533731T2 (de) | 1994-12-28 | 2005-10-27 | Cambridge Display Technology Ltd. | Polymere für optische Vorrichtungen |
| WO1997005184A1 (en) | 1995-07-28 | 1997-02-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
| ATE247372T1 (de) | 1996-09-04 | 2003-08-15 | Cambridge Display Tech Ltd | Lichtemittierende organische vorrichtungen mit verbesserter kathode |
| JP3899566B2 (ja) * | 1996-11-25 | 2007-03-28 | セイコーエプソン株式会社 | 有機ｅｌ表示装置の製造方法 |
| US6452218B1 (en) | 1997-06-10 | 2002-09-17 | Uniax Corporation | Ultra-thin alkaline earth metals as stable electron-injecting electrodes for polymer light emitting diodes |
| GB9805476D0 (en) * | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
| KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
| GB2335884A (en) | 1998-04-02 | 1999-10-06 | Cambridge Display Tech Ltd | Flexible substrates for electronic or optoelectronic devices |
| EP1155096B1 (en) * | 1999-02-04 | 2005-03-09 | Dow Global Technologies Inc. | Fluorene copolymers and devices made therefrom |
| GB9903251D0 (en) | 1999-02-12 | 1999-04-07 | Cambridge Display Tech Ltd | Opto-electric devices |
| DE60035970T2 (de) | 1999-03-05 | 2008-05-15 | Cambridge Display Technology Ltd. | Polymerherstellung |
| GB2348316A (en) | 1999-03-26 | 2000-09-27 | Cambridge Display Tech Ltd | Organic opto-electronic device |
| WO2001019142A1 (en) | 1999-09-03 | 2001-03-15 | Uniax Corporation | Encapsulation of organic electronic devices |
| US6413645B1 (en) | 2000-04-20 | 2002-07-02 | Battelle Memorial Institute | Ultrabarrier substrates |
| GB0004541D0 (en) | 2000-02-25 | 2000-04-19 | Cambridge Display Tech Ltd | Luminescent polymer |
| US6939624B2 (en) * | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
| ATE358170T1 (de) * | 2000-10-03 | 2007-04-15 | Cambridge Display Tech Ltd | Lichtemittierende polymermischungen und daraus hergestellte lichtemittierende anordnungen |
| GB0024155D0 (en) * | 2000-10-03 | 2000-11-15 | Cambridge Display Tech Ltd | Electroluminescent polymers |
| IL154960A0 (en) | 2000-10-10 | 2003-10-31 | Du Pont | Polymers having attached luminescent metal complexes and devices made with sych polymers |
| KR100825183B1 (ko) | 2000-11-30 | 2008-04-24 | 캐논 가부시끼가이샤 | 발광 소자 및 표시 장치 |
| KR100533556B1 (ko) | 2000-11-30 | 2005-12-06 | 캐논 가부시끼가이샤 | 발광 소자 및 표시 장치 |
| US6489615B2 (en) * | 2000-12-15 | 2002-12-03 | Northrop Grumman Corporation | Ultra sensitive silicon sensor |
| US6693295B2 (en) | 2000-12-25 | 2004-02-17 | Fuji Photo Film Co., Ltd. | Indole derivative, material for light-emitting device and light-emitting device using the same |
| US7592074B2 (en) | 2001-02-20 | 2009-09-22 | Isis Innovation Limited | Metal-containing dendrimers |
| DE10109027A1 (de) | 2001-02-24 | 2002-09-05 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
| SG92833A1 (en) | 2001-03-27 | 2002-11-19 | Sumitomo Chemical Co | Polymeric light emitting substance and polymer light emitting device using the same |
| KR20030087056A (ko) | 2001-04-05 | 2003-11-12 | 상꾜 가부시키가이샤 | 벤즈아미딘 유도체 |
| KR20030024690A (ko) | 2001-04-17 | 2003-03-26 | 코닌클리케 필립스 일렉트로닉스 엔.브이. | 저 황산염 및 고 금속 이온 함량을 갖는 전도성 투명중합체 층을 포함하는 ｌｅｄ |
| JP2002324679A (ja) | 2001-04-26 | 2002-11-08 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子 |
| KR100424090B1 (ko) * | 2001-06-25 | 2004-03-22 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자용 정공 수송층, 그 정공 수송층을사용한유기 전계 발광 소자 및 그 소자의 제조 방법 |
| JP4574936B2 (ja) | 2001-08-31 | 2010-11-04 | 日本放送協会 | 燐光発光性化合物及び燐光発光性組成物 |
| EP1426399A4 (en) | 2001-09-04 | 2005-07-13 | Canon Kk | HIGHLY MOLECULAR COMPOUNDS AND ORGANIC LUMINESCENT DEVICES |
| AU2003275203A1 (en) | 2002-09-24 | 2004-04-19 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| GB0329364D0 (en) * | 2003-12-19 | 2004-01-21 | Cambridge Display Tech Ltd | Optical device |
| US20050175861A1 (en) * | 2004-02-10 | 2005-08-11 | H.C. Starck Gmbh | Polythiophene compositions for improving organic light-emitting diodes |
| DE102004006583A1 (de) | 2004-02-10 | 2005-09-01 | H.C. Starck Gmbh | Polythiophenformulierungen zur Verbesserung von organischen Leuchtdioden |
| DE112005002495B4 (de) * | 2004-10-11 | 2016-11-17 | Cambridge Display Technology Ltd. | Polares halbleitendes Lochtransportmaterial |
-
2005
- 2005-07-14 GB GBGB0514476.1A patent/GB0514476D0/en not_active Ceased
-
2006
- 2006-07-14 GB GB0800204A patent/GB2442165B/en not_active Expired - Fee Related
- 2006-07-14 KR KR1020087000757A patent/KR101296040B1/ko not_active Expired - Fee Related
- 2006-07-14 DE DE112006001828T patent/DE112006001828B4/de not_active Expired - Fee Related
- 2006-07-14 US US11/995,576 patent/US8308987B2/en not_active Expired - Fee Related
- 2006-07-14 WO PCT/GB2006/002643 patent/WO2007007117A1/en not_active Ceased
- 2006-07-14 CN CN2006800255841A patent/CN101223236B/zh not_active Expired - Fee Related
- 2006-07-14 JP JP2008520961A patent/JP2009501259A/ja active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007327058A (ja) * | 2006-06-07 | 2007-12-20 | Samsung Sdi Co Ltd | 導電性高分子組成物およびこれを採用した電子素子 |
| JP2008211135A (ja) * | 2007-02-28 | 2008-09-11 | Sumitomo Chemical Co Ltd | 有機発光素子およびその製造方法 |
| JP2009239279A (ja) * | 2008-03-07 | 2009-10-15 | Sumitomo Chemical Co Ltd | 積層構造体 |
| US8951646B2 (en) | 2008-03-07 | 2015-02-10 | Sumitomo Chemical Company, Limited | Layered structure comprising a layer containing a conjugated polymer compound |
| JP2012216821A (ja) * | 2011-03-28 | 2012-11-08 | Sumitomo Chemical Co Ltd | 電子デバイス、高分子化合物 |
| US9306169B2 (en) | 2011-03-28 | 2016-04-05 | Sumitomo Chemical Company, Limited | Electronic device, polymer compound, organic compound, and method of producing polymer compound |
| JP2013243280A (ja) * | 2012-05-22 | 2013-12-05 | Hitachi Chemical Co Ltd | 有機エレクトロニクス材料、インク組成物、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、及び光電変換素子 |
| WO2015159932A1 (ja) * | 2014-04-18 | 2015-10-22 | 住友化学株式会社 | 発光素子およびそれに用いる高分子化合物 |
| KR20160029684A (ko) * | 2014-09-05 | 2016-03-15 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 도전성 중합체 복합체 및 기판 |
| JP2016056346A (ja) * | 2014-09-05 | 2016-04-21 | 信越化学工業株式会社 | 導電性ポリマー複合体及び基板 |
| KR101997952B1 (ko) | 2014-09-05 | 2019-07-08 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 도전성 중합체 복합체 및 기판 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2442165A (en) | 2008-03-26 |
| GB0514476D0 (en) | 2005-08-17 |
| US20080265756A1 (en) | 2008-10-30 |
| GB2442165B (en) | 2011-06-08 |
| DE112006001828B4 (de) | 2013-08-01 |
| US8308987B2 (en) | 2012-11-13 |
| CN101223236A (zh) | 2008-07-16 |
| WO2007007117A1 (en) | 2007-01-18 |
| GB0800204D0 (en) | 2008-02-20 |
| KR20080031272A (ko) | 2008-04-08 |
| DE112006001828T5 (de) | 2008-05-15 |
| KR101296040B1 (ko) | 2013-08-12 |
| CN101223236B (zh) | 2012-11-28 |
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