CN101427381B - 含有带甲硅烷基乙炔基基团的并苯-噻吩共聚物的电子器件 - Google Patents
含有带甲硅烷基乙炔基基团的并苯-噻吩共聚物的电子器件 Download PDFInfo
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- CN101427381B CN101427381B CN2007800142797A CN200780014279A CN101427381B CN 101427381 B CN101427381 B CN 101427381B CN 2007800142797 A CN2007800142797 A CN 2007800142797A CN 200780014279 A CN200780014279 A CN 200780014279A CN 101427381 B CN101427381 B CN 101427381B
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- silylethynyl
- diyl
- copolymer
- bis
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- -1 silylethynyl groups Chemical group 0.000 title claims abstract description 134
- 229920001577 copolymer Polymers 0.000 title claims abstract description 110
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000004065 semiconductor Substances 0.000 claims description 88
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 239000011248 coating agent Substances 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 18
- 229920003026 Acene Polymers 0.000 claims description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 15
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
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- 125000001424 substituent group Chemical group 0.000 claims description 3
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- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 169
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- 125000004432 carbon atom Chemical group C* 0.000 description 61
- 229910052757 nitrogen Inorganic materials 0.000 description 58
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- LOIBXBUXWRVJCF-UHFFFAOYSA-N 4-(4-aminophenyl)-3-phenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 LOIBXBUXWRVJCF-UHFFFAOYSA-N 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 7
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- 239000003989 dielectric material Substances 0.000 description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 7
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- 150000002431 hydrogen Chemical class 0.000 description 7
- 230000027756 respiratory electron transport chain Effects 0.000 description 7
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 6
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- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 6
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 4
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Images
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- 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
- C08G61/123—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 derived from five-membered heterocyclic compounds
- C08G61/126—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 derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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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
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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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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- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
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- 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
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- 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]
- H10K50/14—Carrier transporting layers
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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
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
-
- 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
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- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
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- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Thin Film Transistor (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
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| US11/379,662 | 2006-04-21 | ||
| US11/379,662 US7495251B2 (en) | 2006-04-21 | 2006-04-21 | Electronic devices containing acene-thiophene copolymers with silylethynyl groups |
| PCT/US2007/066622 WO2007124286A1 (en) | 2006-04-21 | 2007-04-13 | Electronic devices containing acene-thiophene copolymers with silylethynyl groups |
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| EP1883950B1 (en) * | 2005-05-21 | 2012-07-25 | Merck Patent GmbH | Oligomeric polyacene and semiconductor formulation |
| US20070246689A1 (en) * | 2006-04-11 | 2007-10-25 | Jiaxin Ge | Transparent thin polythiophene films having improved conduction through use of nanomaterials |
| US7666968B2 (en) * | 2006-04-21 | 2010-02-23 | 3M Innovative Properties Company | Acene-thiophene copolymers with silethynly groups |
| KR101314931B1 (ko) * | 2006-10-30 | 2013-10-04 | 삼성전자주식회사 | 유기 고분자 반도체, 이의 제조방법 및 이를 이용한 양극성 유기 박막 트랜지스터 |
| US20080142793A1 (en) * | 2006-11-10 | 2008-06-19 | Tang Ming L | Organic Semiconductors |
| US9520563B2 (en) * | 2007-11-21 | 2016-12-13 | The Board Of Trustees Of The Leland Stanford Junior University | Patterning of organic semiconductor materials |
| JP2011508967A (ja) * | 2007-12-17 | 2011-03-17 | スリーエム イノベイティブ プロパティズ カンパニー | アントラセンを主成分とする溶液加工性有機半導体 |
| JP5658145B2 (ja) * | 2008-05-30 | 2015-01-21 | スリーエム イノベイティブ プロパティズ カンパニー | シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法 |
| EP2304821B1 (en) * | 2008-06-11 | 2012-06-27 | 3M Innovative Properties Company | Mixed solvent systems for deposition of organic semiconductors |
| EP2318420A1 (en) * | 2008-06-19 | 2011-05-11 | 3M Innovative Properties Company | Solution processable organic semiconductors |
| US8154013B2 (en) | 2008-11-19 | 2012-04-10 | Xerox Corporation | Organic thin-film transistors |
| JP2011082396A (ja) * | 2009-10-08 | 2011-04-21 | Panasonic Electric Works Co Ltd | タンデム型有機太陽電池 |
| US8513466B2 (en) * | 2009-11-30 | 2013-08-20 | University Of New Hampshire | Class of soluble, photooxidatively resistant acene derivatives |
| US8822731B2 (en) * | 2009-11-30 | 2014-09-02 | University Of New Hampshire | Soluble, persistent nonacene derivatives |
| WO2011068968A2 (en) * | 2009-12-02 | 2011-06-09 | University Of South Florida | Transparent contacts organic solar panel by spray |
| US8980677B2 (en) | 2009-12-02 | 2015-03-17 | University Of South Florida | Transparent contacts organic solar panel by spray |
| JP5682571B2 (ja) * | 2009-12-14 | 2015-03-11 | コニカミノルタ株式会社 | 有機光電変換素子 |
| KR101626363B1 (ko) * | 2009-12-16 | 2016-06-02 | 엘지디스플레이 주식회사 | 안트라세닐계 교호 공중합체, 그 제조 방법 및 이를 이용한 유기 박막 트랜지스터 |
| EP2517274B1 (en) * | 2009-12-23 | 2017-05-24 | Merck Patent GmbH | Compositions comprising polymeric binders |
| SG190738A1 (en) * | 2010-12-06 | 2013-07-31 | Merck Patent Gmbh | Non-linear acene derivatives and their use as organic semiconductors |
| US8398234B2 (en) | 2011-05-03 | 2013-03-19 | Kimberly-Clark Worldwide, Inc. | Electro-thermal antifog optical devices |
| JP2013119589A (ja) * | 2011-12-07 | 2013-06-17 | Sumitomo Chemical Co Ltd | 高分子化合物及び電子素子 |
| WO2014145609A1 (en) | 2013-03-15 | 2014-09-18 | University Of South Florida | Mask-stack-shift method to fabricate organic solar array by spray |
| JP6514005B2 (ja) * | 2014-04-08 | 2019-05-15 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及びインク組成物 |
| US10675362B2 (en) * | 2016-08-02 | 2020-06-09 | Trustees Of Tufts College | Photoluminescent nanoparticles and their uses in detection or quantification of singlet oxygen |
| JP7306313B2 (ja) * | 2020-04-21 | 2023-07-11 | 信越化学工業株式会社 | (ポリ)チオフェン-(ポリ)シロキサンブロックコポリマー及びその製造方法 |
| JP7638722B2 (ja) * | 2021-02-18 | 2025-03-04 | テイカ株式会社 | 導電性高分子分散液、導電性高分子膜および電解コンデンサ |
| CN115558412B (zh) * | 2022-10-12 | 2023-06-09 | 深圳市华之美科技有限公司 | 一种聚酰亚胺复合材料及其制备方法和应用 |
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- 2007-04-13 WO PCT/US2007/066622 patent/WO2007124286A1/en not_active Ceased
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- 2007-04-13 AT AT07760639T patent/ATE459104T1/de not_active IP Right Cessation
- 2007-04-13 EP EP07760639A patent/EP2011157B1/en not_active Not-in-force
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2009534853A (ja) | 2009-09-24 |
| WO2007124286A1 (en) | 2007-11-01 |
| EP2011157B1 (en) | 2010-02-24 |
| CN101427381A (zh) | 2009-05-06 |
| EP2011157A1 (en) | 2009-01-07 |
| EP2011157A4 (en) | 2009-05-06 |
| ATE459104T1 (de) | 2010-03-15 |
| JP5237264B2 (ja) | 2013-07-17 |
| DE602007004969D1 (de) | 2010-04-08 |
| US7495251B2 (en) | 2009-02-24 |
| US20070249087A1 (en) | 2007-10-25 |
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