CN102648186B - 发光芳基-杂芳基化合物 - Google Patents
发光芳基-杂芳基化合物 Download PDFInfo
- Publication number
- CN102648186B CN102648186B CN201080035757.4A CN201080035757A CN102648186B CN 102648186 B CN102648186 B CN 102648186B CN 201080035757 A CN201080035757 A CN 201080035757A CN 102648186 B CN102648186 B CN 102648186B
- Authority
- CN
- China
- Prior art keywords
- compound
- alkyl
- optionally substituted
- mixture
- phenyl
- 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.)
- Expired - Fee Related
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- 0 CC1=Nc2c(*)c(*)c(*)c(*)c2*1 Chemical compound CC1=Nc2c(*)c(*)c(*)c(*)c2*1 0.000 description 2
- FJVOIXBMWCFFEL-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)ccc2Oc(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)nc2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)ccc2Oc(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)nc2c1cccc2 FJVOIXBMWCFFEL-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01J—MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY
- G01J1/00—Photometry, e.g. photographic exposure meter
- G01J1/42—Photometry, e.g. photographic exposure meter using electric radiation detectors
-
- 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
- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- H05B47/00—Circuit arrangements for operating light sources in general, i.e. where the type of light source is not relevant
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Electroluminescent Light Sources (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Photovoltaic Devices (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22147209P | 2009-06-29 | 2009-06-29 | |
| US61/221,472 | 2009-06-29 | ||
| PCT/US2010/040467 WO2011008560A1 (en) | 2009-06-29 | 2010-06-29 | Emissive aryl-heteroaryl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102648186A CN102648186A (zh) | 2012-08-22 |
| CN102648186B true CN102648186B (zh) | 2015-12-16 |
Family
ID=43027682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080035757.4A Expired - Fee Related CN102648186B (zh) | 2009-06-29 | 2010-06-29 | 发光芳基-杂芳基化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20100326526A1 (enExample) |
| EP (1) | EP2448925B1 (enExample) |
| JP (1) | JP5681179B2 (enExample) |
| KR (1) | KR20120060817A (enExample) |
| CN (1) | CN102648186B (enExample) |
| TW (1) | TWI480267B (enExample) |
| WO (1) | WO2011008560A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8323805B2 (en) | 2009-06-04 | 2012-12-04 | Nitto Denko Corporation | Emissive aryl-heteroaryl acetylenes |
| US20100326526A1 (en) | 2009-06-29 | 2010-12-30 | Nitto Denko Corporation | Emissive aryl-heteroaryl compounds |
| JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
| WO2012009283A1 (en) * | 2010-07-13 | 2012-01-19 | Nitto Denko Corporation | Phototherapy methods and devices comprising emissive aryl-heteroaryl compounds |
| US8426040B2 (en) | 2010-12-22 | 2013-04-23 | Nitto Denko Corporation | Compounds for use in light-emitting devices |
| KR20140020873A (ko) | 2011-01-27 | 2014-02-19 | 닛토덴코 가부시키가이샤 | 임의 치환된 테르페닐 및 쿠아테르페닐 화합물을 포함한 광선요법 디바이스 및 방법 |
| EP2681970B1 (en) * | 2011-03-03 | 2018-01-17 | Nitto Denko Corporation | Porous films for use in light-emitting devices |
| US8933243B2 (en) | 2011-06-22 | 2015-01-13 | Nitto Denko Corporation | Polyphenylene host compounds |
| US9051274B2 (en) * | 2011-06-24 | 2015-06-09 | Semiconductor Energy Laboratory Co., Ltd. | Triarylamine compound, light-emitting element, light-emitting device, electronic device, and lighting device |
| US8820923B2 (en) | 2011-08-05 | 2014-09-02 | Nitto Denko Corporation | Optical element for correcting color blindness |
| US9853220B2 (en) | 2011-09-12 | 2017-12-26 | Nitto Denko Corporation | Efficient organic light-emitting diodes and fabrication of the same |
| US8952364B2 (en) | 2011-11-10 | 2015-02-10 | Nitto Denko Corporation | Light-emitting devices comprising nanostructures |
| WO2013155483A1 (en) * | 2012-04-13 | 2013-10-17 | Nitto Denko Corporation | Phototherapy devices and methods comprising optionally substitutted quinquiesphenyl compounds |
| US20150228907A1 (en) * | 2012-08-31 | 2015-08-13 | Nitto Denko Corporation | Porous Films for Use in Light-Emitting Devices |
| US9379336B2 (en) | 2012-08-31 | 2016-06-28 | Nitto Denko Corporation | Compounds for use in light emitting devices |
| US9966538B2 (en) * | 2012-11-07 | 2018-05-08 | Lms Co., Ltd. | Compound, light-emitting element and electronic device comprising same |
| US9112159B2 (en) | 2012-12-10 | 2015-08-18 | Nitto Denko Corporation | Bipolar hosts for light emitting devices |
| TWI607077B (zh) * | 2012-12-10 | 2017-12-01 | 日東電工股份有限公司 | 有機發光主體材料 |
| US9614162B2 (en) | 2012-12-17 | 2017-04-04 | Nitto Denko Corporation | Light-emitting devices comprising emissive layer |
| JP6236813B2 (ja) * | 2013-03-14 | 2017-11-29 | 株式会社リコー | 溶液、有機半導体材料、有機半導体膜、電子デバイス及び電子機器 |
| US10510914B2 (en) | 2013-03-21 | 2019-12-17 | Board Of Trustees Of Michigan State University | Transparent energy-harvesting devices |
| US10510961B1 (en) | 2013-08-01 | 2019-12-17 | Nitto Denko Corporation | Organic light emitting host materials |
| CN104650042A (zh) * | 2014-07-04 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | 含二元咪唑类衍生物的制备方法 |
| JP6506330B2 (ja) * | 2017-03-02 | 2019-04-24 | 国立大学法人京都大学 | アリールアミン類の製造方法 |
| US12247126B2 (en) | 2018-05-09 | 2025-03-11 | Board Of Trustees Of Michigan State University | Near-infrared harvesting transparent luminescent solar concentrators with engineered stokes shift |
| CN108924972B (zh) * | 2018-08-03 | 2021-04-06 | 高红彦 | 一种电热膜及其制备方法 |
| WO2020068670A1 (en) | 2018-09-24 | 2020-04-02 | Board Of Trustees Of Michigan State University | Transparent luminescent solar concentrator |
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|---|---|---|---|---|
| EP0499222A1 (en) * | 1991-02-13 | 1992-08-19 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device, display apparatus and display method |
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| TWI394746B (zh) * | 2007-11-16 | 2013-05-01 | Academia Sinica | 有機電激發光裝置及其材料 |
| JP5572806B2 (ja) | 2007-12-25 | 2014-08-20 | 国立大学法人名古屋大学 | オリゴフェニレン骨格を含む有機材料及びそれを用いた発光素子 |
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| JP5479759B2 (ja) * | 2008-09-05 | 2014-04-23 | 株式会社半導体エネルギー研究所 | ベンゾオキサゾール誘導体、発光素子用材料、発光素子、発光装置及び電子機器 |
| US8323805B2 (en) * | 2009-06-04 | 2012-12-04 | Nitto Denko Corporation | Emissive aryl-heteroaryl acetylenes |
| US8420235B2 (en) * | 2009-06-04 | 2013-04-16 | Nitto Denko Corporation | Emissive diaryl acetylenes |
| US20100326526A1 (en) | 2009-06-29 | 2010-12-30 | Nitto Denko Corporation | Emissive aryl-heteroaryl compounds |
| JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
-
2010
- 2010-06-29 US US12/825,953 patent/US20100326526A1/en not_active Abandoned
- 2010-06-29 JP JP2012518585A patent/JP5681179B2/ja not_active Expired - Fee Related
- 2010-06-29 CN CN201080035757.4A patent/CN102648186B/zh not_active Expired - Fee Related
- 2010-06-29 TW TW099121238A patent/TWI480267B/zh not_active IP Right Cessation
- 2010-06-29 WO PCT/US2010/040467 patent/WO2011008560A1/en not_active Ceased
- 2010-06-29 KR KR1020127002423A patent/KR20120060817A/ko not_active Withdrawn
- 2010-06-29 EP EP10728568.6A patent/EP2448925B1/en not_active Not-in-force
-
2013
- 2013-06-24 US US13/925,625 patent/US8927121B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0499222A1 (en) * | 1991-02-13 | 1992-08-19 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device, display apparatus and display method |
Non-Patent Citations (4)
| Title |
|---|
| Solution-Processible Bipolar Triphenylamine-Benzimidazole Derivatives for Highly Efficient Single-Layer Organic Light-Emitting Diodes;Ziyi Ge,等;《Chem.Mater.》;20080311;第20卷(第7期);第2532-2537页 * |
| Spin-coated highly efficient phosphorescent organic light-emitting diodes based on bipolar triphenylamine-benzimidazole derivatives;Ziyi Ge,等;《ADVANCED FUNCTIONAL MATERIALS》;20080222;第18卷(第4期);第584-590页 * |
| Synthesis and properties of highly fluorescent liquid crystals containing benzoxazole moiety;SEHOON KIM;《MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY. SECTION A. MOLECULAR CRYSTALS AND LIQUID CRYSTALS》;19991231;第307卷;第405-408页 * |
| Synthesis of poly(benzothiazole)s by direct polycondensation of dicarboxylic acids with 2,5-diamino-1,4-benzenedithiol dihydrochloride using phosphorus pentoxide/methanesulfonic acid as condensing agent and solvent;Mutsuru UEDA,等;《POLYMER JOURNAL》;19861231;第18卷(第2期);第117-122页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2448925B1 (en) | 2017-12-06 |
| US20100326526A1 (en) | 2010-12-30 |
| US8927121B2 (en) | 2015-01-06 |
| CN102648186A (zh) | 2012-08-22 |
| KR20120060817A (ko) | 2012-06-12 |
| EP2448925A1 (en) | 2012-05-09 |
| US20130284907A1 (en) | 2013-10-31 |
| JP5681179B2 (ja) | 2015-03-04 |
| WO2011008560A1 (en) | 2011-01-20 |
| TW201114747A (en) | 2011-05-01 |
| JP2012532135A (ja) | 2012-12-13 |
| TWI480267B (zh) | 2015-04-11 |
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