WO2015097232A1 - N-doped semiconducting material comprising phosphine oxide matrix and metal dopant - Google Patents
N-doped semiconducting material comprising phosphine oxide matrix and metal dopant Download PDFInfo
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- WO2015097232A1 WO2015097232A1 PCT/EP2014/079191 EP2014079191W WO2015097232A1 WO 2015097232 A1 WO2015097232 A1 WO 2015097232A1 EP 2014079191 W EP2014079191 W EP 2014079191W WO 2015097232 A1 WO2015097232 A1 WO 2015097232A1
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- Prior art keywords
- semiconducting material
- electronic device
- doped semiconducting
- electrically doped
- electron
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Classifications
-
- 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
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5329—Polyphosphine oxides or thioxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/64—Acridine or hydrogenated acridine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65525—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a seven-(or more) membered ring
- C07F9/65527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a seven-(or more) membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- 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
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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- Spectroscopy & Molecular Physics (AREA)
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- Optics & Photonics (AREA)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016542211A JP6832704B2 (en) | 2013-12-23 | 2014-12-23 | N-doped semiconductor material containing phosphine oxide base material and metal dopant |
KR1020167020171A KR102339316B1 (en) | 2013-12-23 | 2014-12-23 | N-doped semiconducting material comprising phosphine oxide matrix and metal dopant |
US15/107,456 US20160322568A1 (en) | 2013-12-23 | 2014-12-23 | N-Doped Semiconducting Material Comprising Phosphine Oxide Matrix and Metal Dopant |
EP14819023.4A EP3087621B1 (en) | 2013-12-23 | 2014-12-23 | N-doped semiconducting material comprising phosphine oxide matrix and metal dopant |
CN201480070560.2A CN106062986B (en) | 2013-12-23 | 2014-12-23 | Include the semi-conducting material of the n- of phosphine oxide matrix and metal dopant doping |
US17/185,901 US20210202842A1 (en) | 2013-12-23 | 2021-02-25 | N-Doped Semiconducting Material Comprising Phosphine Oxide Matrix and Metal Dopant |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13199413.9 | 2013-12-23 | ||
EP13199413 | 2013-12-23 | ||
EP14171326.3A EP2887416B1 (en) | 2013-12-23 | 2014-06-05 | N-doped semiconducting material comprising phosphine oxide matrix and metal dopant |
EP14171326.3 | 2014-06-05 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/107,456 A-371-Of-International US20160322568A1 (en) | 2013-12-23 | 2014-12-23 | N-Doped Semiconducting Material Comprising Phosphine Oxide Matrix and Metal Dopant |
US17/185,901 Division US20210202842A1 (en) | 2013-12-23 | 2021-02-25 | N-Doped Semiconducting Material Comprising Phosphine Oxide Matrix and Metal Dopant |
Publications (1)
Publication Number | Publication Date |
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WO2015097232A1 true WO2015097232A1 (en) | 2015-07-02 |
Family
ID=49955145
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2014/079191 WO2015097232A1 (en) | 2013-12-23 | 2014-12-23 | N-doped semiconducting material comprising phosphine oxide matrix and metal dopant |
Country Status (8)
Country | Link |
---|---|
US (2) | US20160322568A1 (en) |
EP (2) | EP2887416B1 (en) |
JP (2) | JP6832704B2 (en) |
KR (1) | KR102339316B1 (en) |
CN (1) | CN106062986B (en) |
ES (1) | ES2673573T3 (en) |
HK (1) | HK1212095A1 (en) |
WO (1) | WO2015097232A1 (en) |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6013384A (en) * | 1997-01-27 | 2000-01-11 | Junji Kido | Organic electroluminescent devices |
JP2006073581A (en) * | 2004-08-31 | 2006-03-16 | Toray Ind Inc | Light emitting device and material therefor |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5093698A (en) | 1991-02-12 | 1992-03-03 | Kabushiki Kaisha Toshiba | Organic electroluminescent device |
JP3865406B2 (en) * | 1995-07-28 | 2007-01-10 | 住友化学株式会社 | 2,7-Aryl-9-substituted fluorene and 9-substituted fluorene oligomers and polymers |
US6107452A (en) * | 1998-10-09 | 2000-08-22 | International Business Machines Corporation | Thermally and/or photochemically crosslinked electroactive polymers in the manufacture of opto-electronic devices |
JP4876333B2 (en) | 2000-06-08 | 2012-02-15 | 東レ株式会社 | Light emitting element |
DE10058578C2 (en) | 2000-11-20 | 2002-11-28 | Univ Dresden Tech | Light-emitting component with organic layers |
DE10116876B4 (en) | 2001-04-04 | 2004-09-23 | Infineon Technologies Ag | Process for doping electrically conductive organic compounds, organic field effect transistor and process for its production |
US6936961B2 (en) * | 2003-05-13 | 2005-08-30 | Eastman Kodak Company | Cascaded organic electroluminescent device having connecting units with N-type and P-type organic layers |
US20070001151A1 (en) * | 2005-01-12 | 2007-01-04 | Sapochak Linda S | Organic materials with tunable electric and electroluminescent properties |
DE102004010954A1 (en) | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Use of a metal complex as an n-dopant for an organic semiconductive matrix material, organic semiconductor material and electronic component |
US7507694B2 (en) | 2004-03-12 | 2009-03-24 | Halliburton Energy Services, Inc. | Surfactant-free emulsions and methods of use thereof |
JP2008509565A (en) | 2004-08-13 | 2008-03-27 | ノヴァレッド・アクチエンゲゼルシャフト | Laminate for luminescent component |
EP1648042B1 (en) | 2004-10-07 | 2007-05-02 | Novaled AG | A method for doping a semiconductor material with cesium |
US20080233410A1 (en) * | 2005-11-17 | 2008-09-25 | Idemitsu Kosan Co., Ltd. | Transition metal complex compound |
EP1939320B1 (en) | 2005-12-07 | 2013-08-21 | Novaled AG | Method of vapour deposition |
DE602006001930D1 (en) | 2005-12-23 | 2008-09-04 | Novaled Ag | of organic layers |
EP1804308B1 (en) | 2005-12-23 | 2012-04-04 | Novaled AG | An organic light emitting device with a plurality of organic electroluminescent units stacked upon each other |
EP1837927A1 (en) | 2006-03-22 | 2007-09-26 | Novaled AG | Use of heterocyclic radicals for doping of organic semiconductors |
US7830081B2 (en) * | 2006-03-22 | 2010-11-09 | General Electric Company | Optoelectronic devices with multilayered structures |
DE102007012794B3 (en) | 2007-03-16 | 2008-06-19 | Novaled Ag | New pyrido(3,2-h)quinazoline compounds useful to prepare doped organic semi-conductor, which is useful in an organic light-emitting diode, preferably organic solar cells, and modules for an electronic circuits, preferably displays |
JP5081010B2 (en) * | 2007-03-26 | 2012-11-21 | 富士フイルム株式会社 | Organic electroluminescence device |
US20080241518A1 (en) * | 2007-03-26 | 2008-10-02 | Tasuku Satou | Organic electroluminescence element |
JP2008244012A (en) * | 2007-03-26 | 2008-10-09 | Fujifilm Corp | Organic electroluminescent element |
JP5230218B2 (en) * | 2007-03-26 | 2013-07-10 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
JP2009076508A (en) | 2007-09-18 | 2009-04-09 | Fujifilm Corp | Organic electroluminescent element |
KR101003267B1 (en) * | 2008-01-18 | 2010-12-21 | 주식회사 엘지화학 | Organic Light Emitting Device and Method for Manufacturing the Same |
DE102008011185A1 (en) | 2008-02-27 | 2009-09-03 | Osram Opto Semiconductors Gmbh | Process for producing a doped organic semiconducting layer |
US8603642B2 (en) | 2009-05-13 | 2013-12-10 | Global Oled Technology Llc | Internal connector for organic electronic devices |
CN102668156B (en) * | 2009-08-18 | 2016-01-13 | 大电株式会社 | Organic electroluminescent device and novel alcohol solubility phosphorescent light-emitting materials |
EP2395571B1 (en) | 2010-06-10 | 2013-12-04 | Novaled AG | Organic electronic device comprising an organic semiconducting material |
WO2012008281A1 (en) * | 2010-07-13 | 2012-01-19 | 東レ株式会社 | Light emitting element |
KR20120020901A (en) * | 2010-08-31 | 2012-03-08 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
EP2452946B1 (en) | 2010-11-16 | 2014-05-07 | Novaled AG | Pyridylphosphinoxides for organic electronic device and organic electronic device |
JP5611086B2 (en) * | 2011-03-10 | 2014-10-22 | パナソニック株式会社 | Deposition boat and film formation method using the same |
CN102229623B (en) * | 2011-05-10 | 2013-12-25 | 南京邮电大学 | Spirofluorene xanthene phosphine oxide electro-phosphorescent main materials and synthesis and application methods thereof |
US9972784B2 (en) | 2011-06-13 | 2018-05-15 | Lg Chem, Ltd. | Compounds and organic electronic device using same |
CN103765623B (en) * | 2011-08-22 | 2016-06-01 | 默克专利有限公司 | Organic electroluminescence device |
CN104247070B (en) | 2011-11-30 | 2017-04-12 | 诺瓦尔德股份有限公司 | Display |
TWI558711B (en) * | 2011-11-30 | 2016-11-21 | 諾瓦發光二極體有限公司 | Organic electronic device |
US20150034927A1 (en) * | 2012-02-10 | 2015-02-05 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element, and organic electroluminescent element using same |
EP2860782B1 (en) * | 2013-10-09 | 2019-04-17 | Novaled GmbH | Semiconducting material comprising a phosphine oxide matrix and metal salt |
EP2887412B1 (en) * | 2013-12-23 | 2016-07-27 | Novaled GmbH | Semiconducting material |
EP3079179A1 (en) * | 2015-04-08 | 2016-10-12 | Novaled GmbH | Semiconducting material comprising a phosphine oxide matrix and metal salt |
-
2014
- 2014-06-05 ES ES14171326.3T patent/ES2673573T3/en active Active
- 2014-06-05 EP EP14171326.3A patent/EP2887416B1/en active Active
- 2014-12-23 US US15/107,456 patent/US20160322568A1/en not_active Abandoned
- 2014-12-23 CN CN201480070560.2A patent/CN106062986B/en active Active
- 2014-12-23 WO PCT/EP2014/079191 patent/WO2015097232A1/en active Application Filing
- 2014-12-23 KR KR1020167020171A patent/KR102339316B1/en active IP Right Grant
- 2014-12-23 JP JP2016542211A patent/JP6832704B2/en active Active
- 2014-12-23 EP EP14819023.4A patent/EP3087621B1/en active Active
-
2015
- 2015-12-23 HK HK15112637.7A patent/HK1212095A1/en unknown
-
2019
- 2019-10-25 JP JP2019194259A patent/JP2020025121A/en active Pending
-
2021
- 2021-02-25 US US17/185,901 patent/US20210202842A1/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6013384A (en) * | 1997-01-27 | 2000-01-11 | Junji Kido | Organic electroluminescent devices |
JP2006073581A (en) * | 2004-08-31 | 2006-03-16 | Toray Ind Inc | Light emitting device and material therefor |
Non-Patent Citations (1)
Title |
---|
LINDA S. SAPOCHAK ET AL: "<title>Design strategies for achieving high triplet energy electron transporting host materials for blue electrophosphorescence</title>", PROCEEDINGS OF SPIE, vol. 6333, 31 August 2006 (2006-08-31), pages 63330F, XP055186526, ISSN: 0277-786X, DOI: 10.1117/12.684126 * |
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Also Published As
Publication number | Publication date |
---|---|
EP3087621A1 (en) | 2016-11-02 |
EP3087621B1 (en) | 2019-04-17 |
EP2887416A1 (en) | 2015-06-24 |
US20160322568A1 (en) | 2016-11-03 |
CN106062986A (en) | 2016-10-26 |
ES2673573T3 (en) | 2018-06-22 |
CN106062986B (en) | 2018-09-14 |
JP2017502518A (en) | 2017-01-19 |
US20210202842A1 (en) | 2021-07-01 |
HK1212095A1 (en) | 2016-06-03 |
JP6832704B2 (en) | 2021-02-24 |
EP2887416B1 (en) | 2018-02-21 |
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JP2020025121A (en) | 2020-02-13 |
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