JP5684250B2 - 有機層のインクジェット印刷または他の用途向けの液体組成物 - Google Patents
有機層のインクジェット印刷または他の用途向けの液体組成物 Download PDFInfo
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- JP5684250B2 JP5684250B2 JP2012516132A JP2012516132A JP5684250B2 JP 5684250 B2 JP5684250 B2 JP 5684250B2 JP 2012516132 A JP2012516132 A JP 2012516132A JP 2012516132 A JP2012516132 A JP 2012516132A JP 5684250 B2 JP5684250 B2 JP 5684250B2
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- 238000000151 deposition Methods 0.000 claims description 6
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- MNALUTYMBUBKNX-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OC)=CC=C21 MNALUTYMBUBKNX-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006838 isophorone group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical class FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Chemical group C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical compound C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical compound N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052710 silicon Chemical group 0.000 description 1
- 239000010703 silicon Chemical group 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical group C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
-
- 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
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
-
- 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
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- 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
- H10K85/10—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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
-
- 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
- H10K71/311—Purifying organic semiconductor materials
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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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
本出願は、2009年6月17日出願の米国仮特許出願第61/187,862号明細書に対する優先権の利益を主張するものである。
Claims (21)
- 有機電子デバイス用の有機層の形成方法において:
− 溶媒調製物中に混合された小分子有機半導体材料を含む液体組成物を得るステップであって、前記溶媒調製物が溶媒と前記溶媒よりも高い沸点を有する0.1wt%以下の不純物とを含み、前記溶媒が1atm(101.3kPa)で200℃以上の沸点を有しているステップと;
− 前記液体組成物を表面上に被着させるステップと;
を含み、前記溶媒が、1−テトラロン、2−テトラロン、2−(フェニルエポキシ)テトラロン、及び6−(メトキシ)テトラロンからなる群から選択される方法。 - 前記溶媒調製物が精製済み溶媒調製物であり、前記液体組成物を提供するステップが、
− 前記溶媒と前記溶媒よりも高い沸点を有する0.1wt%超の不純物とを含む粗製溶媒調製物を得るステップと;
− 前記溶媒よりも高い沸点を有する前記不純物の少なくとも一部分を除去することによって前記粗製溶媒調製物を精製して、前記精製済み溶媒調製物を得るステップと;
− 前記溶媒調製物と前記小分子有機半導体材料を混合するステップと、
を含む、請求項1に記載の方法。 - 前記粗製溶媒調製物を精製するステップが、前記粗製溶媒調製物を蒸留するステップを含む、請求項2に記載の方法。
- 前記溶媒が1atm(101.3kPa)で250℃以上の沸点を有する、請求項1に記載の方法。
- 前記溶媒が1−テトラロンである、請求項1に記載の方法。
- 前記有機半導体材料の濃度が0.01〜2wt%の範囲内にある、請求項1に記載の方法。
- 前記有機半導体材料が遷移金属の有機金属錯体である、請求項1に記載の方法。
- アノード、カソードおよび前記アノードと前記カソードの間に配置された有機層を有する有機発光デバイスの製造方法において、前記有機層が請求項1に記載の方法によって形成される、方法。
- 前記被着ステップがインクジェット印刷により実施される、請求項8に記載の方法。
- − 1atm(101.3kPa)で200℃以上の沸点を有する、1−テトラロン、2−テトラロン、2−(フェニルエポキシ)テトラロン、及び6−(メトキシ)テトラロンからなる群から選択される溶媒と;
− 0.01〜10wt%の範囲内の濃度で前記溶媒中に混合された小分子有機半導体材料と;
を含み、前記溶媒に比べて高い沸点を有する0.1wt%以下の不純物を有している液体組成物。 - 前記有機半導体材料の濃度が0.01〜2wt%の範囲内にある、請求項10に記載の液体組成物。
- 前記有機半導体材料がリン光発光性化合物である、請求項10に記載の液体組成物。
- 前記リン光発光性化合物が遷移金属の有機金属錯体である、請求項12に記載の液体組成物。
- 前記液体組成物が前記リン光化合物のためのホスト化合物をさらに含む、請求項12に記載の液体組成物。
- 前記ホスト化合物がカルバゾール含有化合物である、請求項14に記載の液体組成物。
- 前記溶媒が1atm(101.3kPa)で250℃以上の沸点を有する、請求項10に記載の液体組成物。
- 前記溶媒が1−テトラロンである、請求項10に記載の液体組成物。
- 請求項1〜9のいずれか一項に記載された有機層の形成方法を用いて有機層を形成させるステップを含む、有機電子デバイスの製造方法。
- 請求項18に記載の製造方法を用いて製造された有機電子デバイス。
- 請求項10〜17のいずれか一項に記載の液体組成物を表面上に被着させて有機層を形成させるステップを含む、有機電子デバイスの製造方法。
- 請求項20に記載の製造方法を用いて製造された有機電子デバイス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US18786209P | 2009-06-17 | 2009-06-17 | |
US61/187,862 | 2009-06-17 | ||
PCT/US2010/037920 WO2010147818A1 (en) | 2009-06-17 | 2010-06-09 | Liquid compositions for inkjet printing of organic layers or other uses |
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JP2012531012A JP2012531012A (ja) | 2012-12-06 |
JP5684250B2 true JP5684250B2 (ja) | 2015-03-11 |
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JP2012516132A Active JP5684250B2 (ja) | 2009-06-17 | 2010-06-09 | 有機層のインクジェット印刷または他の用途向けの液体組成物 |
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US (2) | US8187916B2 (ja) |
EP (2) | EP2962338B1 (ja) |
JP (1) | JP5684250B2 (ja) |
KR (1) | KR101618395B1 (ja) |
CN (2) | CN102460759B (ja) |
TW (1) | TWI535801B (ja) |
WO (1) | WO2010147818A1 (ja) |
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EP2688117A1 (en) | 2012-07-20 | 2014-01-22 | Solvay Sa | Process for forming a layer of an organic electronic device |
DE102012018583B4 (de) | 2012-09-20 | 2018-10-31 | Heidelberger Druckmaschinen Ag | Verfahren zum Drucken einer funktionalen Schicht für elektronische Bauteile |
EP2713414A1 (en) * | 2012-10-01 | 2014-04-02 | Solvay SA | Process for the manufacture of a multilayer structure |
US9252363B2 (en) * | 2012-10-04 | 2016-02-02 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
JP6287036B2 (ja) * | 2013-10-16 | 2018-03-07 | セイコーエプソン株式会社 | インクの評価方法、機能素子の製造方法、有機el素子の製造方法 |
WO2015084256A1 (en) * | 2013-12-02 | 2015-06-11 | Nanyang Technological University | Hole transporting molecules and their use in solar cells |
JP6551238B2 (ja) | 2014-02-14 | 2019-07-31 | 日立化成株式会社 | ポリマー又はオリゴマー、正孔輸送材料組成物、及び、これらを用いた有機エレクトロニクス素子 |
WO2015194429A1 (ja) * | 2014-06-17 | 2015-12-23 | 株式会社ダイセル | 有機el素子製造用溶剤 |
WO2016148170A1 (ja) | 2015-03-17 | 2016-09-22 | 富士フイルム株式会社 | 有機半導体組成物、及び、有機半導体素子の製造方法 |
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JP7051684B2 (ja) * | 2015-12-15 | 2022-04-11 | メルク パテント ゲーエムベーハー | 有機電子調合物のための溶媒として芳香族基を含むエステル |
CN105679935B (zh) * | 2016-01-22 | 2018-04-13 | 华南理工大学 | 一种有机材料的溶液成膜方法及设备 |
JP6936980B2 (ja) * | 2016-12-31 | 2021-09-22 | 株式会社Flosfia | 発光層の製造方法 |
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CN107104185A (zh) | 2017-08-29 |
US20100323464A1 (en) | 2010-12-23 |
CN102460759B (zh) | 2016-12-07 |
EP3667750A1 (en) | 2020-06-17 |
US8373162B2 (en) | 2013-02-12 |
US8187916B2 (en) | 2012-05-29 |
CN102460759A (zh) | 2012-05-16 |
TW201107435A (en) | 2011-03-01 |
EP2962338A1 (en) | 2016-01-06 |
US20120270349A1 (en) | 2012-10-25 |
KR20120037409A (ko) | 2012-04-19 |
KR101618395B1 (ko) | 2016-05-04 |
JP2012531012A (ja) | 2012-12-06 |
EP2962338B1 (en) | 2020-02-05 |
TWI535801B (zh) | 2016-06-01 |
CN107104185B (zh) | 2019-08-30 |
WO2010147818A1 (en) | 2010-12-23 |
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