JP6249700B2 - 有機層をインクジェット印刷するためのアリールオキシアルキルカルボキシレート溶媒組成物 - Google Patents
有機層をインクジェット印刷するためのアリールオキシアルキルカルボキシレート溶媒組成物 Download PDFInfo
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- JP6249700B2 JP6249700B2 JP2013195075A JP2013195075A JP6249700B2 JP 6249700 B2 JP6249700 B2 JP 6249700B2 JP 2013195075 A JP2013195075 A JP 2013195075A JP 2013195075 A JP2013195075 A JP 2013195075A JP 6249700 B2 JP6249700 B2 JP 6249700B2
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- 239000002904 solvent Substances 0.000 title claims description 64
- 239000000203 mixture Substances 0.000 title claims description 46
- 239000012044 organic layer Substances 0.000 title claims description 27
- 238000007641 inkjet printing Methods 0.000 title description 16
- 239000007788 liquid Substances 0.000 claims description 39
- 239000010410 layer Substances 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000009835 boiling Methods 0.000 claims description 20
- 239000004065 semiconductor Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical group CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 7
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- 230000008018 melting Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims 2
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- BZCKRPHEZOHHBK-UHFFFAOYSA-N methyl 2-phenoxyacetate Chemical compound COC(=O)COC1=CC=CC=C1 BZCKRPHEZOHHBK-UHFFFAOYSA-N 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 150000003384 small molecules Chemical class 0.000 description 6
- 238000010129 solution processing Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
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- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 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
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring 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
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000008096 xylene Substances 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
- H10K71/15—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
- H10K50/00—Organic light-emitting devices
-
- 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
-
- 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
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
-
- 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
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
Claims (20)
- 0.01質量%〜10質量%の濃度の低分子有機半導体材料と、
25℃以下の融点を有する溶媒であって、前記溶媒の化合物が、
(式中、R1は、C 1 アルキルまたはC 3−6 アルキルであり、R2は、C1−6アルキルであり、R3は、C1−6アルキル及びアリールから独立して選択される1以上の任意の置換基である)
によって表される溶媒とを含むことを特徴とする液体組成物。 - 溶媒が、1atmで260℃以下の沸点を有する請求項1に記載の液体組成物。
- 溶媒が、1atmで150℃〜260℃の沸点を有する請求項2に記載の液体組成物。
- 溶媒の化合物が、166〜400の分子量を有する請求項1に記載の液体組成物。
- 低分子有機半導体材料が、リン光発光化合物である請求項1に記載の液体組成物。
- 低分子ホスト化合物を更に含む請求項5に記載の液体組成物。
- 有機半導体材料が、電荷輸送材料である請求項1に記載の液体組成物。
- 液体組成物が、23℃で5cPs〜15cPsの粘度を有する請求項1に記載の液体組成物。
- 溶媒が、23℃で5cPs〜15cPsの粘度を有する請求項1に記載の液体組成物。
- 溶媒が、フェノキシ酢酸メチルである請求項1に記載の液体組成物。
- 有機半導体材料が、3,000以下の分子量を有する請求項1に記載の液体組成物。
- 溶媒ブレンドを形成するために別の溶媒を更に含む請求項1に記載の液体組成物。
- 別の溶媒が、3−フェノキシトルエンである請求項12に記載の液体組成物。
- 溶媒が、1atmで150℃〜260℃の沸点、23℃で5cPs〜15cPsの粘度、及び166〜400の分子量を有する請求項1に記載の液体組成物。
- 有機電子デバイス用の有機層を形成する方法であって、
請求項1に記載の液体組成物を表面に付着させる工程と、
前記液体組成物を乾燥させて、前記表面上に有機層を形成する工程とを含むことを特徴とする方法。 - 有機電子デバイスが、有機発光デバイスであり、有機層が、発光層である請求項15に記載の方法。
- 表面が、電子デバイスの別の有機層又は電極の表面である請求項16に記載の方法。
- アノードと、
カソードと、
前記アノードと前記カソードとの間に存在する有機層であって、請求項15に記載の方法によって作製される前記有機層とを含むことを特徴とする有機電子デバイス。 - 有機層が、発光層である請求項18に記載のデバイス。
- 低分子有機半導体材料が、リン光発光化合物である請求項19に記載のデバイス。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/644,480 | 2012-10-04 | ||
US13/644,480 US9252363B2 (en) | 2012-10-04 | 2012-10-04 | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014075344A JP2014075344A (ja) | 2014-04-24 |
JP6249700B2 true JP6249700B2 (ja) | 2017-12-20 |
Family
ID=50432033
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013195075A Active JP6249700B2 (ja) | 2012-10-04 | 2013-09-20 | 有機層をインクジェット印刷するためのアリールオキシアルキルカルボキシレート溶媒組成物 |
Country Status (3)
Country | Link |
---|---|
US (1) | US9252363B2 (ja) |
JP (1) | JP6249700B2 (ja) |
KR (1) | KR102092973B1 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101666781B1 (ko) * | 2013-06-28 | 2016-10-17 | 엘지디스플레이 주식회사 | 유기 발광 소자 |
JP6331462B2 (ja) * | 2014-02-25 | 2018-05-30 | 日立化成株式会社 | 有機エレクトロニクス素子の製造方法 |
EP3235891B1 (en) * | 2015-02-03 | 2020-12-23 | Sumitomo Chemical Company, Ltd. | Composition and light-emitting element using same |
EP3581633B1 (en) | 2015-06-12 | 2021-01-27 | Merck Patent GmbH | Esters containing non-aromatic cycles as solvents for oled formulations |
KR102643183B1 (ko) * | 2015-07-15 | 2024-03-04 | 메르크 파텐트 게엠베하 | 유기 반도전성 화합물들을 포함하는 조성물 |
CN108137971B (zh) * | 2015-11-12 | 2021-07-06 | 广州华睿光电材料有限公司 | 用于印刷电子的组合物及其在电子器件中的应用 |
CN108291103B (zh) | 2015-11-12 | 2021-12-07 | 广州华睿光电材料有限公司 | 印刷组合物、包含其的电子器件及功能材料薄膜的制备方法 |
JP6733156B2 (ja) * | 2015-11-27 | 2020-07-29 | 東ソー株式会社 | 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ |
US11171294B2 (en) | 2015-12-15 | 2021-11-09 | Merck Patent Gmbh | Esters containing aromatic groups as solvents for organic electronic formulations |
EP3428989B1 (en) * | 2016-03-10 | 2021-04-21 | Sumitomo Chemical Company Limited | Light-emitting element |
KR102005867B1 (ko) * | 2016-06-17 | 2019-07-31 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
US11248138B2 (en) | 2016-11-23 | 2022-02-15 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing ink formulations, preparation methods and uses thereof |
US11201299B2 (en) * | 2017-05-04 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10930864B2 (en) * | 2017-05-10 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
Family Cites Families (172)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
EP0650955B1 (en) | 1993-11-01 | 1998-08-19 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
JP4081149B2 (ja) * | 1996-01-12 | 2008-04-23 | 山本化成株式会社 | フタロシアニン化合物を用いる湿式太陽電池 |
US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6402986B1 (en) * | 1999-07-16 | 2002-06-11 | The Trustees Of Boston University | Compositions and methods for luminescence lifetime comparison |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
US6565994B2 (en) | 2000-02-10 | 2003-05-20 | Fuji Photo Film Co., Ltd. | Light emitting device material comprising iridium complex and light emitting device using same material |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
JP5241053B2 (ja) | 2000-08-11 | 2013-07-17 | ザ、トラスティーズ オブ プリンストン ユニバーシティ | 有機金属化合物及び放射移行有機電気燐光体 |
US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
EP1407501B1 (en) | 2001-06-20 | 2009-05-20 | Showa Denko K.K. | Light emitting material and organic light-emitting device |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
US7431968B1 (en) | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising 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 |
US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
JP3919583B2 (ja) | 2002-04-12 | 2007-05-30 | キヤノン株式会社 | 有機発光素子 |
US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
DE10238903A1 (de) | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
KR100686268B1 (ko) | 2002-08-27 | 2007-02-28 | 후지필름 가부시키가이샤 | 유기금속 착체, 유기 el 소자 및 유기 el 디스플레이 |
US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
EP2759585B1 (en) | 2002-11-26 | 2018-08-15 | Konica Minolta Business Technologies, Inc. | Organic electroluminescent element, and display and illuminator |
JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
US7338722B2 (en) | 2003-03-24 | 2008-03-04 | The University Of Southern California | Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir |
US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
US7345301B2 (en) | 2003-04-15 | 2008-03-18 | Merck Patent Gmbh | Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures |
US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
US7740955B2 (en) | 2003-04-23 | 2010-06-22 | Konica Minolta Holdings, Inc. | Organic electroluminescent device and display |
WO2004107822A1 (ja) | 2003-05-29 | 2004-12-09 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子 |
EP2924094B1 (en) | 2003-06-02 | 2017-04-05 | UDC Ireland Limited | Organic electroluminescent devices and metal complex compounds |
TW200504175A (en) | 2003-06-09 | 2005-02-01 | Hitachi Chemical Co Ltd | Metal coordination compound, polymer composition and organic electroluminescence element using the same |
JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
JP2005093428A (ja) * | 2003-08-14 | 2005-04-07 | Mitsubishi Chemicals Corp | 有機電界発光素子用組成物及び有機電界発光素子 |
US7504049B2 (en) | 2003-08-25 | 2009-03-17 | Semiconductor Energy Laboratory Co., Ltd. | Electrode device for organic device, electronic device having electrode device for organic device, and method of forming electrode device for organic device |
HU0302888D0 (en) | 2003-09-09 | 2003-11-28 | Pribenszky Csaba Dr | In creasing of efficacity of stable storage by freezing of embryos in preimplantation stage with pretreatment by pressure |
US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
US7442797B2 (en) | 2003-11-04 | 2008-10-28 | Takasago International Corporation | Platinum complex and light emitting device |
JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
WO2005089024A1 (ja) | 2004-03-11 | 2005-09-22 | Mitsubishi Chemical Corporation | 電荷輸送膜用組成物及びイオン化合物、それを用いた電荷輸送膜及び有機電界発光素子、並びに、有機電界発光素子の製造方法及び電荷輸送膜の製造方法 |
TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
US7655323B2 (en) | 2004-05-18 | 2010-02-02 | The University Of Southern California | OLEDs utilizing macrocyclic ligand systems |
US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
WO2005123873A1 (ja) | 2004-06-17 | 2005-12-29 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
CA2568667A1 (en) | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
JP4858169B2 (ja) | 2004-07-23 | 2012-01-18 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
US20060182993A1 (en) * | 2004-08-10 | 2006-08-17 | Mitsubishi Chemical Corporation | Compositions for organic electroluminescent device and organic electroluminescent device |
DE102004057072A1 (de) | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
WO2006067074A1 (en) | 2004-12-23 | 2006-06-29 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with nucleophilic carbene ligands |
US7230107B1 (en) | 2004-12-29 | 2007-06-12 | E. I. Du Pont De Nemours And Company | Metal quinoline complexes |
EP1859656B1 (en) | 2004-12-30 | 2013-07-17 | E.I. Du Pont De Nemours And Company | Organometallic complexes |
WO2006082742A1 (ja) | 2005-02-04 | 2006-08-10 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
KR100803125B1 (ko) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
WO2006098120A1 (ja) | 2005-03-16 | 2006-09-21 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子 |
DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
GB2439030B (en) | 2005-04-18 | 2011-03-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, display and illuminating device |
US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
EP2277978B1 (en) | 2005-05-31 | 2016-03-30 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
CN101193875B (zh) | 2005-06-07 | 2011-05-11 | 新日铁化学株式会社 | 有机金属络合物和使用了其的有机电致发光元件 |
WO2007002683A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
WO2007004380A1 (ja) | 2005-07-01 | 2007-01-11 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US7462406B2 (en) | 2005-11-15 | 2008-12-09 | Eastman Kodak Company | OLED devices with dinuclear copper compounds |
JPWO2007063796A1 (ja) | 2005-12-01 | 2009-05-07 | 新日鐵化学株式会社 | 有機電界発光素子 |
JP4593631B2 (ja) | 2005-12-01 | 2010-12-08 | 新日鐵化学株式会社 | 有機電界発光素子用化合物及び有機電界発光素子 |
US8142909B2 (en) | 2006-02-10 | 2012-03-27 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
KR20180117719A (ko) | 2006-02-10 | 2018-10-29 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-f]페난트리딘 및 디이미다조[1,2-a:1',2'-c]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
WO2007125714A1 (ja) | 2006-04-26 | 2007-11-08 | Idemitsu Kosan Co., Ltd. | 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
US8076839B2 (en) | 2006-05-11 | 2011-12-13 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US8563145B2 (en) | 2006-06-02 | 2013-10-22 | Idemitsu Kosan Co., Ltd. | Material containing two or three dibenzofuran groups, dibenzothiophene groups, or a combination thereof, which is operable for organic electroluminescence elements, and organic electroluminescence elements using the material |
EP2055701A1 (en) | 2006-08-23 | 2009-05-06 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivatives and organic electroluminescent devices made by using the same |
JP5099013B2 (ja) | 2006-10-13 | 2012-12-12 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US20080102223A1 (en) | 2006-11-01 | 2008-05-01 | Sigurd Wagner | Hybrid layers for use in coatings on electronic devices or other articles |
US7968146B2 (en) | 2006-11-01 | 2011-06-28 | The Trustees Of Princeton University | Hybrid layers for use in coatings on electronic devices or other articles |
EP2080762B1 (en) | 2006-11-09 | 2016-09-14 | Nippon Steel & Sumikin Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
KR20120135325A (ko) | 2006-11-24 | 2012-12-12 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그것을 이용한 유기 전기발광 소자 |
US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
EP2437326A3 (en) | 2006-12-13 | 2013-11-13 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device and lighting device |
US20080268517A1 (en) * | 2007-02-08 | 2008-10-30 | The California Institute Of Technology | Stable, functional chimeric cytochrome p450 holoenzymes |
KR101904627B1 (ko) | 2007-03-08 | 2018-10-04 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
WO2008132085A1 (de) | 2007-04-26 | 2008-11-06 | Basf Se | Silane enthaltend phenothiazin-s-oxid oder phenothiazin-s,s-dioxid-gruppen und deren verwendung in oleds |
WO2009000673A2 (en) | 2007-06-22 | 2008-12-31 | Basf Se | Light emitting cu(i) complexes |
KR101577465B1 (ko) | 2007-07-05 | 2015-12-14 | 바스프 에스이 | 카르벤 전이 금속 착체 이미터, 및 디실릴카르바졸, 디실릴디벤조푸란, 디실릴디벤조티오펜, 디실릴디벤조포스폴, 디실릴디벤조티오펜 s-옥사이드 및 디실릴디벤조티오펜 s,s-디옥사이드로부터 선택된 1종 이상의 화합물을 포함하는 유기 발광 다이오드 |
US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
WO2009008311A1 (ja) | 2007-07-07 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | クリセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
TW200909560A (en) | 2007-07-07 | 2009-03-01 | Idemitsu Kosan Co | Organic electroluminescence device and material for organic electroluminescence devcie |
TW200909558A (en) | 2007-07-07 | 2009-03-01 | Idemitsu Kosan Co | Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
JP5619418B2 (ja) | 2007-07-10 | 2014-11-05 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
KR20100065302A (ko) | 2007-07-27 | 2010-06-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무기 나노입자를 포함하는 전기 전도성 중합체의 수성 분산물 |
KR101630883B1 (ko) | 2007-08-08 | 2016-06-15 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
KR101741778B1 (ko) | 2007-10-17 | 2017-05-31 | 유디씨 아일랜드 리미티드 | 가교된 카르벤 리간드를 포함하는 전이 금속 착물 및 이의 용도 |
US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
KR101353635B1 (ko) | 2007-11-15 | 2014-01-20 | 이데미쓰 고산 가부시키가이샤 | 벤조크리센 유도체 및 이것을 사용한 유기 전계 발광 소자 |
US8759819B2 (en) | 2007-11-22 | 2014-06-24 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
CN101874316B (zh) | 2007-11-22 | 2012-09-05 | 出光兴产株式会社 | 有机el元件以及含有机el材料的溶液 |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
US8471248B2 (en) | 2008-02-12 | 2013-06-25 | Basf Se | Electroluminiscent metal complexes with dibenzo[f,h] quinoxalines |
JP5258339B2 (ja) | 2008-03-24 | 2013-08-07 | 株式会社トクヤマ | シリコン製造プロセス |
KR101563763B1 (ko) | 2008-05-07 | 2015-10-27 | 더 트러스티즈 오브 프린스턴 유니버시티 | 전자 장치들 또는 다른 물품들 위의 코팅들에 사용하기 위한 혼성 층들 |
US8057919B2 (en) | 2008-06-05 | 2011-11-15 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
US8049411B2 (en) | 2008-06-05 | 2011-11-01 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
US8318323B2 (en) | 2008-06-05 | 2012-11-27 | Idemitsu Kosan Co., Ltd. | Polycyclic compounds and organic electroluminescence device employing the same |
CN102131891B (zh) | 2008-06-30 | 2014-01-29 | 通用显示公司 | 具有含硫基团的空穴传输材料 |
WO2010027583A1 (en) | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
US9034483B2 (en) | 2008-09-16 | 2015-05-19 | Universal Display Corporation | Phosphorescent materials |
KR101762964B1 (ko) | 2008-10-27 | 2017-07-28 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하 주입 및 수송 층 |
KR100901888B1 (ko) | 2008-11-13 | 2009-06-09 | (주)그라쎌 | 신규한 전기발광용 유기금속 화합물 및 이를 발광재료로 채용하고 있는 전기발광소자 |
JP5707665B2 (ja) | 2008-12-03 | 2015-04-30 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置 |
US8815415B2 (en) | 2008-12-12 | 2014-08-26 | Universal Display Corporation | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
EP2393819B9 (de) | 2009-01-07 | 2017-12-27 | UDC Ireland Limited | Silyl- und heteroatom-substituierte verbindungen ausgewählt aus carbazolen, dibenzofuranen, dibenzothiophenen und dibenzophospholen und ihre anwendung in der organischen elektronik |
US9067947B2 (en) | 2009-01-16 | 2015-06-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
DE102009007038A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
US8174000B2 (en) * | 2009-02-11 | 2012-05-08 | Universal Display Corporation | Liquid compositions for inkjet printing of organic layers or other uses |
JP2010219508A (ja) * | 2009-02-18 | 2010-09-30 | Mitsubishi Chemicals Corp | 有機電界発光素子用組成物、有機薄膜、有機電界発光素子、有機el表示装置および有機el照明 |
KR101511072B1 (ko) | 2009-03-20 | 2015-04-10 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자 |
US8722205B2 (en) | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
US8709615B2 (en) | 2011-07-28 | 2014-04-29 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
EP3667750A1 (en) * | 2009-06-17 | 2020-06-17 | Universal Display Corporation | Liquid compositions for inkjet printing of organic layers or other uses |
DE102009049587A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
KR101837095B1 (ko) | 2009-10-28 | 2018-03-09 | 바스프 에스이 | 이종 리간드 카르벤 착체 및 유기 전자장치에서의 이의 용도 |
KR101927676B1 (ko) | 2009-12-18 | 2018-12-10 | 닛산 가가쿠 가부시키가이샤 | 3,4-디알콕시티오펜 공중합체, 및 그의 제조 방법 및 소자 |
US9087622B2 (en) | 2009-12-22 | 2015-07-21 | Universal Display Corporation | Nitrile solvent composistions for inkjet printing of organic layers |
JP4617393B1 (ja) | 2010-01-15 | 2011-01-26 | 富士フイルム株式会社 | 有機電界発光素子 |
US9156870B2 (en) | 2010-02-25 | 2015-10-13 | Universal Display Corporation | Phosphorescent emitters |
JP2011256129A (ja) * | 2010-06-08 | 2011-12-22 | Mitsubishi Chemicals Corp | 有機金属錯体材料、有機電界発光素子用組成物、有機電界発光素子、有機el表示装置及び有機el照明 |
US9193745B2 (en) | 2011-11-15 | 2015-11-24 | Universal Display Corporation | Heteroleptic iridium complex |
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KR20140044263A (ko) | 2014-04-14 |
KR102092973B1 (ko) | 2020-03-25 |
US9252363B2 (en) | 2016-02-02 |
JP2014075344A (ja) | 2014-04-24 |
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