JP2006290891A - シリル置換シクロメタル化遷移金属錯体およびこれを用いた有機電界発光素子 - Google Patents
シリル置換シクロメタル化遷移金属錯体およびこれを用いた有機電界発光素子 Download PDFInfo
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- JP2006290891A JP2006290891A JP2006110282A JP2006110282A JP2006290891A JP 2006290891 A JP2006290891 A JP 2006290891A JP 2006110282 A JP2006110282 A JP 2006110282A JP 2006110282 A JP2006110282 A JP 2006110282A JP 2006290891 A JP2006290891 A JP 2006290891A
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- silyl
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- 229910052723 transition metal Inorganic materials 0.000 title claims abstract description 44
- 150000003624 transition metals Chemical class 0.000 title claims abstract description 44
- 239000000126 substance Substances 0.000 claims abstract description 30
- 239000003446 ligand Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 239000013522 chelant Substances 0.000 claims abstract description 4
- 125000000129 anionic group Chemical group 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 238000010657 cyclometalation reaction Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 238000005401 electroluminescence Methods 0.000 description 27
- 239000010408 film Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 fused rings Chemical group 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
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- LKAPTZKZHMOIRE-KVTDHHQDSA-N (2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbaldehyde Chemical compound OC[C@H]1O[C@H](C=O)[C@@H](O)[C@@H]1O LKAPTZKZHMOIRE-KVTDHHQDSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- JFGRRFVBMSRJDM-UHFFFAOYSA-N 2,6-difluoro-3-(4-trimethylsilylpyridin-2-yl)benzonitrile Chemical compound FC1=C(C=CC(=C1C#N)F)C1=NC=CC(=C1)[Si](C)(C)C JFGRRFVBMSRJDM-UHFFFAOYSA-N 0.000 description 2
- NSXJIVKTJYDWTO-UHFFFAOYSA-N 2,6-difluoro-3-pyridin-2-ylbenzonitrile Chemical compound FC1=C(C#N)C(F)=CC=C1C1=CC=CC=N1 NSXJIVKTJYDWTO-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- IWXXOLRNBUYLQZ-UHFFFAOYSA-N Cc(cccc1)c1NCc1ccccc1NC Chemical compound Cc(cccc1)c1NCc1ccccc1NC IWXXOLRNBUYLQZ-UHFFFAOYSA-N 0.000 description 1
- JFATYZVHWKUWSP-WDZFZDKYSA-N Cc1cc(-c2ccccc2)ccc1NC/C=C\NC Chemical compound Cc1cc(-c2ccccc2)ccc1NC/C=C\NC JFATYZVHWKUWSP-WDZFZDKYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SVPGUDRYMNIGFO-UHFFFAOYSA-N phenyl quinoline-2-carboxylate Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)OC1=CC=CC=C1 SVPGUDRYMNIGFO-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000327 poly(triphenylamine) polymer Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 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
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G43/00—Control devices, e.g. for safety, warning or fault-correcting
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04Q—SELECTING
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/30—Coordination compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G2207/00—Indexing codes relating to constructional details, configuration and additional features of a handling device, e.g. Conveyors
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H—ELECTRICITY
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- H04Q—SELECTING
- H04Q2209/00—Arrangements in telecontrol or telemetry systems
- H04Q2209/40—Arrangements in telecontrol or telemetry systems using a wireless architecture
- H04Q2209/47—Arrangements in telecontrol or telemetry systems using a wireless architecture using RFID associated with sensors
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- H10K2101/10—Triplet emission
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- 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
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- Crystallography & Structural Chemistry (AREA)
- High Energy & Nuclear Physics (AREA)
- Optics & Photonics (AREA)
- Computer Networks & Wireless Communication (AREA)
- Electroluminescent Light Sources (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims (9)
- 前記MがRu、Rh、Os、Ir、Pt、またはAuであることを特徴とする、請求項1ないし3のいずれか1項に記載のシリル置換シクロメタル化遷移金属錯体。
- 前記MがIrであることを特徴とする、請求項4に記載のシリル置換シクロメタル化遷移金属錯体。
- 一対の電極の間に有機膜を含む有機電界発光素子において、
前記有機膜が、請求項1ないし6のいずれか1項に記載のシリル置換シクロメタル化遷移金属錯体を含むことを特徴とする、有機電界発光素子。 - 前記有機膜が高分子ホスト、高分子ホストと低分子ホストとの混合物、低分子ホスト、および非発光高分子マトリックスからなる群より選択される少なくとも一つをさらに含むことを特徴とする、請求項7に記載の有機電界発光素子。
- 前記有機膜が緑色発光物質または赤色発光物質をさらに含むことを特徴とする、請求項7または8に記載の有機電界発光素子。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2005-0030288 | 2005-04-12 | ||
KR1020050030288A KR101223717B1 (ko) | 2005-04-12 | 2005-04-12 | 실릴 치환된 시클로메탈화 전이금속 착물 및 이를 이용한 유기 전계 발광 소자 |
Publications (2)
Publication Number | Publication Date |
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JP2006290891A true JP2006290891A (ja) | 2006-10-26 |
JP5165854B2 JP5165854B2 (ja) | 2013-03-21 |
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JP2006110282A Active JP5165854B2 (ja) | 2005-04-12 | 2006-04-12 | シリル置換シクロメタル化遷移金属錯体およびこれを用いた有機電界発光素子 |
Country Status (4)
Country | Link |
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US (1) | US7776458B2 (ja) |
JP (1) | JP5165854B2 (ja) |
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JP2009152572A (ja) * | 2007-11-27 | 2009-07-09 | Fujifilm Corp | 有機電界発光素子 |
WO2011158544A1 (ja) * | 2010-06-17 | 2011-12-22 | 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 |
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JP5846119B2 (ja) * | 2010-06-17 | 2016-01-20 | 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材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
WO2013038804A1 (ja) | 2011-09-12 | 2013-03-21 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
WO2013038929A1 (ja) | 2011-09-12 | 2013-03-21 | 新日鉄住金化学株式会社 | 含ケイ素四員環構造を有する有機電界発光素子用材料及び有機電界発光素子 |
WO2013038843A1 (ja) | 2011-09-12 | 2013-03-21 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
WO2013088934A1 (ja) | 2011-12-12 | 2013-06-20 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及びそれを用いた有機電界発光素子 |
WO2013137001A1 (ja) | 2012-03-12 | 2013-09-19 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
WO2014002629A1 (ja) | 2012-06-28 | 2014-01-03 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及び有機電界発光素子 |
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DE112016006231T5 (de) | 2016-01-14 | 2018-10-18 | National Institute Of Advanced Industrial Science And Technology | Verfahren zum Herstellen eines cyclometallierten Iridiumkomplexes |
US10533027B2 (en) | 2016-01-14 | 2020-01-14 | Tanaka Kikinzoku Kogyo K.K. | Method for producing cyclometalated iridium complex |
JP2021191744A (ja) * | 2020-05-19 | 2021-12-16 | 北京夏禾科技有限公司 | 有機発光材料 |
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US20060228582A1 (en) | 2006-10-12 |
KR20060108127A (ko) | 2006-10-17 |
CN1847248B (zh) | 2011-03-23 |
US7776458B2 (en) | 2010-08-17 |
KR101223717B1 (ko) | 2013-01-18 |
JP5165854B2 (ja) | 2013-03-21 |
CN1847248A (zh) | 2006-10-18 |
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