TW200906764A - Charge transport materials for luminescent applications - Google Patents
Charge transport materials for luminescent applications Download PDFInfo
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- TW200906764A TW200906764A TW097120371A TW97120371A TW200906764A TW 200906764 A TW200906764 A TW 200906764A TW 097120371 A TW097120371 A TW 097120371A TW 97120371 A TW97120371 A TW 97120371A TW 200906764 A TW200906764 A TW 200906764A
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Classifications
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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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
-
- 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
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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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
-
- 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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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US94139207P | 2007-06-01 | 2007-06-01 |
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| EP (2) | EP2487219A1 (enExample) |
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| WO (1) | WO2008150822A2 (enExample) |
Cited By (1)
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| TWI615192B (zh) * | 2014-10-31 | 2018-02-21 | 機光科技股份有限公司 | 用於有機光電材料之純化方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100857024B1 (ko) * | 2007-04-13 | 2008-09-05 | (주)그라쎌 | 고성능의 전기 발광 화합물 및 이를 채용하는 유기발광소자 |
| US9153790B2 (en) | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| CN103124711A (zh) * | 2010-08-11 | 2013-05-29 | E·I·内穆尔杜邦公司 | 电活性化合物和组合物以及用该组合物制成的电子装置 |
| JP6359256B2 (ja) * | 2013-09-25 | 2018-07-18 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子、および電子機器 |
| WO2015089028A1 (en) * | 2013-12-11 | 2015-06-18 | E. I. Du Pont De Nemours And Company | Photoactive compositions for electronic applications |
| KR102641909B1 (ko) * | 2018-12-10 | 2024-02-27 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
| KR102679685B1 (ko) * | 2019-03-05 | 2024-06-27 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
| CN114853556B (zh) * | 2022-06-14 | 2023-08-29 | 绍兴文理学院 | 一种5H-二苯并[a,d]环庚烯骨架的新合成方法 |
Family Cites Families (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0650955B1 (en) | 1993-11-01 | 1998-08-19 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
| JP3816969B2 (ja) * | 1994-04-26 | 2006-08-30 | Ｔｄｋ株式会社 | 有機ｅｌ素子 |
| DE69511755T2 (de) * | 1994-04-26 | 2000-01-13 | Tdk Corp | Phenylanthracenderivat und organisches EL-Element |
| JP3586906B2 (ja) | 1994-12-14 | 2004-11-10 | 凸版印刷株式会社 | 透明導電膜の製造方法 |
| 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 |
| US5929194A (en) | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
| JP2000512795A (ja) | 1996-06-12 | 2000-09-26 | ザ トラスティーズ オブ プリンストン ユニバーシテイ | 導電層のプラズマ処理 |
| US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
| US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
| JP3835917B2 (ja) | 1998-02-04 | 2006-10-18 | 三井化学株式会社 | 有機電界発光素子 |
| JPH11338172A (ja) | 1998-05-27 | 1999-12-10 | Chisso Corp | ナフタレン誘導体、及びそれを用いた有機電界発光素子 |
| JP2000068073A (ja) | 1998-08-27 | 2000-03-03 | Futaba Corp | 有機エレクトロルミネッセンス素子及びその製造方法 |
| JP4006862B2 (ja) | 1998-12-22 | 2007-11-14 | コニカミノルタホールディングス株式会社 | 新規アミノ化合物とその製造方法、及び用途 |
| KR100702763B1 (ko) | 1999-02-15 | 2007-04-03 | 이데미쓰 고산 가부시키가이샤 | 유기 전자 발광 소자 및 그의 제조 방법 |
| US6008399A (en) | 1999-03-11 | 1999-12-28 | Mobil Oil Corporation | Process for preparing organic carbonates |
| WO2000070655A2 (en) | 1999-05-13 | 2000-11-23 | The Trustees Of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
| JP4220624B2 (ja) | 1999-07-30 | 2009-02-04 | 三井化学株式会社 | アミン化合物 |
| EP1933395B2 (en) | 1999-12-01 | 2019-08-07 | The Trustees of Princeton University | Complexes of form L2IrX |
| JP4220644B2 (ja) | 2000-02-14 | 2009-02-04 | 三井化学株式会社 | アミン化合物および該化合物を含有する有機電界発光素子 |
| WO2001072673A1 (en) * | 2000-03-29 | 2001-10-04 | Idemitsu Kosan Co., Ltd. | Anthracene derivatives and organic electroluminescent devices made by using the same |
| US6670645B2 (en) | 2000-06-30 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| KR20080041754A (ko) * | 2000-11-24 | 2008-05-13 | 도레이 가부시끼가이샤 | 발광 소자 재료 및 이를 이용한 발광 소자 |
| GB0028867D0 (en) | 2000-11-28 | 2001-01-10 | Avecia Ltd | Field effect translators,methods for the manufacture thereof and materials therefor |
| GB0031634D0 (en) | 2000-12-23 | 2001-02-07 | Johnson Matthey Plc | Organic materials |
| US6875523B2 (en) | 2001-07-05 | 2005-04-05 | E. I. Du Pont De Nemours And Company | Photoactive lanthanide complexes with phosphine oxides, phosphine oxide-sulfides, pyridine N-oxides, and phosphine oxide-pyridine N-oxides, and devices made with such complexes |
| GB0116644D0 (en) | 2001-07-09 | 2001-08-29 | Elam T Ltd | Electroluminescent materials and devices |
| JP4066619B2 (ja) | 2001-07-13 | 2008-03-26 | 三菱化学株式会社 | ビナフチル系化合物及びその製造方法並びに有機電界発光素子 |
| IL158865A0 (en) | 2001-07-18 | 2004-05-12 | Du Pont | Luminescent lanthanide complexes with imine ligands and devices made with such complexes |
| TW588105B (en) | 2001-07-19 | 2004-05-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light-emitting device using the same |
| US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| EP2306788A1 (en) | 2001-12-26 | 2011-04-06 | E. I. du Pont de Nemours and Company | Iridium compounds and devices made therewith |
| JP2003238501A (ja) | 2002-02-18 | 2003-08-27 | Idemitsu Kosan Co Ltd | 芳香族オリゴアミン誘導体およびそれを含有する有機エレクトロルミネッセンス素子 |
| JP2003282274A (ja) | 2002-03-25 | 2003-10-03 | Dainippon Printing Co Ltd | Ｅｌ電極の製造方法 |
| US7241512B2 (en) | 2002-04-19 | 2007-07-10 | 3M Innovative Properties Company | Electroluminescent materials and methods of manufacture and use |
| JP3988539B2 (ja) | 2002-06-04 | 2007-10-10 | 三菱化学株式会社 | 有機電界発光素子 |
| US20040004433A1 (en) | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
| KR101208396B1 (ko) | 2002-07-19 | 2012-12-05 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 및 유기 발광 매체 |
| US6963005B2 (en) | 2002-08-15 | 2005-11-08 | E. I. Du Pont De Nemours And Company | Compounds comprising phosphorus-containing metal complexes |
| US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
| JP2004107292A (ja) | 2002-09-20 | 2004-04-08 | Tosoh Corp | 新規ビナフタレン誘導体並びにその製造方法 |
| CN1681869B (zh) | 2002-09-24 | 2010-05-26 | E.I.内穆尔杜邦公司 | 用于电子器件用聚合物酸胶体制成的可水分散的聚苯胺 |
| EP1546237B2 (en) | 2002-09-24 | 2019-04-24 | E. I. du Pont de Nemours and Company | Water dispersible polythiophenes made with polymeric acid colloids |
| GB0226010D0 (en) | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
| US6872475B2 (en) | 2002-12-03 | 2005-03-29 | Canon Kabushiki Kaisha | Binaphthalene derivatives for organic electro-luminescent devices |
| JP2004224766A (ja) * | 2003-01-27 | 2004-08-12 | Idemitsu Kosan Co Ltd | ビスアントラセン誘導体、それを含む発光性塗膜形成用材料及び有機エレクトロルミネッセンス素子 |
| JP4343850B2 (ja) | 2003-02-20 | 2009-10-14 | 富士フイルム株式会社 | 有機ｅｌ素子及びその製造方法 |
| JP3848306B2 (ja) | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | アントリル誘導基置換化合物およびそれを使用した有機発光素子 |
| US6953705B2 (en) | 2003-07-22 | 2005-10-11 | E. I. Du Pont De Nemours And Company | Process for removing an organic layer during fabrication of an organic electronic device |
| JP3915757B2 (ja) | 2003-08-14 | 2007-05-16 | ソニーケミカル＆インフォメーションデバイス株式会社 | エレクトロルミネスセンスポリマー、有機ｅｌ素子及びディスプレイ装置 |
| JP2005063892A (ja) | 2003-08-19 | 2005-03-10 | Seiko Epson Corp | 有機エレクトロルミネッセンス装置、及び有機エレクトロルミネッセンスｅｌ装置の製造方法、並びに電子機器 |
| GB0321781D0 (en) | 2003-09-17 | 2003-10-15 | Toppan Printing Company Ltd | Electroluminescent device |
| WO2005049546A1 (en) | 2003-11-14 | 2005-06-02 | Sumitomo Chemical Company, Limited | Halogenated bisdiarylaminopolycylic aromatic compounds and polymers thereof |
| US7956350B2 (en) | 2003-11-17 | 2011-06-07 | Sumitomo Chemical Company, Limited | Crosslinkable substituted fluorene compounds |
| TW201219350A (en) | 2003-11-17 | 2012-05-16 | Sumitomo Chemical Co | Crosslinkable arylamine compounds |
| KR20050073233A (ko) | 2004-01-09 | 2005-07-13 | 삼성코닝 주식회사 | 인듐 주석 산화물 박막 제조방법 |
| US7365230B2 (en) | 2004-02-20 | 2008-04-29 | E.I. Du Pont De Nemours And Company | Cross-linkable polymers and electronic devices made with such polymers |
| JP2005243300A (ja) | 2004-02-24 | 2005-09-08 | Sanyo Electric Co Ltd | 有機エレクトロルミネッセント素子及びその製造方法 |
| US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| DE102004020299A1 (de) | 2004-04-26 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere, deren Darstellung und Verwendung |
| US7023013B2 (en) | 2004-06-16 | 2006-04-04 | Eastman Kodak Company | Array of light-emitting OLED microcavity pixels |
| JP2006013222A (ja) | 2004-06-28 | 2006-01-12 | Fuji Photo Film Co Ltd | 有機電界発光素子、およびその製造方法 |
| EP1624500B1 (de) | 2004-08-05 | 2016-03-16 | Novaled GmbH | Spiro-Bifluoren Verbindungen als organisches Halbleiter-Matrixmaterial |
| US7540978B2 (en) | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
| TW200639193A (en) | 2004-12-18 | 2006-11-16 | Merck Patent Gmbh | Electroluminescent polymers and their use |
| US20070181874A1 (en) | 2004-12-30 | 2007-08-09 | Shiva Prakash | Charge transport layers and organic electron devices comprising same |
| KR20070101319A (ko) * | 2005-02-10 | 2007-10-16 | 이데미쓰 고산 가부시키가이샤 | 비스안트라센 유도체 및 그것을 이용한 유기 전기발광 소자 |
| JP4832017B2 (ja) | 2005-04-25 | 2011-12-07 | ケミプロ化成株式会社 | ビナフチル誘導体、それよりなるホスト材料、ホール輸送材料およびそれを用いた有機ｅｌ素子 |
| US20090039775A1 (en) | 2005-09-12 | 2009-02-12 | Idemitsu Kosan Co., Ltd. | Conductive laminate and organic el device |
| JP5009516B2 (ja) | 2005-09-14 | 2012-08-22 | 出光興産株式会社 | 芳香族化合物の製造方法及びその方法で得られた芳香族化合物 |
| EP1937616B1 (en) | 2005-10-21 | 2014-12-17 | LG Chem, Ltd. | New binaphthalene derivatives, preparation method thereof and organic electronic device using the same |
| JP5162891B2 (ja) | 2005-12-08 | 2013-03-13 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、電荷輸送材料組成物および有機電界発光素子 |
| DE102005058557A1 (de) * | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
| 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 |
| US8957407B2 (en) * | 2006-01-27 | 2015-02-17 | Lg Chem, Ltd. | Anthracene derivatives, preparation method thereof and organic light emitting diode using the same |
| JP2007220772A (ja) | 2006-02-15 | 2007-08-30 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス用高分子化合物及びその製造方法 |
| KR100765728B1 (ko) | 2006-03-31 | 2007-10-11 | 성균관대학교산학협력단 | 산소 플라즈마 및 열처리를 이용한 ｉｔｏ 표면처리방법 및이 방법에 의해 제조된 ｏｌｅｄ 소자 |
| EP2003107A1 (en) * | 2006-04-03 | 2008-12-17 | Idemitsu Kosan Co., Ltd. | Bisanthracene derivative and organic electroluminescent device using the same |
| EP2044636A1 (en) | 2006-07-25 | 2009-04-08 | Merck Patent GmbH | Polymer blends and their use in organic light emitting devices |
| US8242223B2 (en) | 2006-08-24 | 2012-08-14 | E I Du Pont De Nemours And Company | Hole transport polymers |
| US20080097076A1 (en) | 2006-08-24 | 2008-04-24 | Radu Nora S | Hole transport polymers |
| US8372525B2 (en) | 2006-11-13 | 2013-02-12 | E I Du Pont De Nemours And Company | Organic electronic device |
| US9012037B2 (en) | 2007-06-01 | 2015-04-21 | Ei Du Pont De Nemours And Company | Hole transport materials |
| US8063399B2 (en) | 2007-11-19 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Electroactive materials |
| US8343381B1 (en) | 2008-05-16 | 2013-01-01 | E I Du Pont De Nemours And Company | Hole transport composition |
| JP2012510540A (ja) | 2008-12-01 | 2012-05-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電気活性材料 |
| JP2012510705A (ja) | 2008-12-01 | 2012-05-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機電子デバイス用のアノード |
| US9099653B2 (en) | 2008-12-01 | 2015-08-04 | E I Du Pont De Nemours And Company | Electroactive materials |
| JP2012511086A (ja) | 2008-12-04 | 2012-05-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電気活性材料 |
-
2008
- 2008-05-29 EP EP12166882A patent/EP2487219A1/en not_active Withdrawn
- 2008-05-29 WO PCT/US2008/065016 patent/WO2008150822A2/en not_active Ceased
- 2008-05-29 JP JP2010510475A patent/JP5453249B2/ja not_active Expired - Fee Related
- 2008-05-29 KR KR1020097027391A patent/KR101644193B1/ko not_active Expired - Fee Related
- 2008-05-29 EP EP08756397A patent/EP2176374A2/en not_active Withdrawn
- 2008-05-29 CN CN2012100444357A patent/CN102617266A/zh active Pending
- 2008-05-29 KR KR1020147035855A patent/KR101589864B1/ko not_active Expired - Fee Related
- 2008-05-29 CN CN2008800171262A patent/CN101689467B/zh not_active Expired - Fee Related
- 2008-05-29 CN CN2012100444198A patent/CN102603459A/zh active Pending
- 2008-05-30 US US12/129,785 patent/US8241762B2/en active Active
- 2008-05-30 TW TW097120371A patent/TW200906764A/zh unknown
-
2012
- 2012-07-12 US US13/547,899 patent/US8460802B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI615192B (zh) * | 2014-10-31 | 2018-02-21 | 機光科技股份有限公司 | 用於有機光電材料之純化方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080297040A1 (en) | 2008-12-04 |
| CN102617266A (zh) | 2012-08-01 |
| WO2008150822A3 (en) | 2009-02-05 |
| KR20100017960A (ko) | 2010-02-16 |
| US20120277498A1 (en) | 2012-11-01 |
| CN101689467B (zh) | 2012-10-03 |
| CN101689467A (zh) | 2010-03-31 |
| JP2010529030A (ja) | 2010-08-26 |
| KR20150016582A (ko) | 2015-02-12 |
| WO2008150822A2 (en) | 2008-12-11 |
| KR101589864B1 (ko) | 2016-01-29 |
| EP2487219A1 (en) | 2012-08-15 |
| CN102603459A (zh) | 2012-07-25 |
| US8241762B2 (en) | 2012-08-14 |
| KR101644193B1 (ko) | 2016-07-29 |
| EP2176374A2 (en) | 2010-04-21 |
| US8460802B2 (en) | 2013-06-11 |
| JP5453249B2 (ja) | 2014-03-26 |
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