JP3984167B2 - 高純度のトリス−オルト−金属置換有機イリジウム化合物の製造方法 - Google Patents
高純度のトリス−オルト−金属置換有機イリジウム化合物の製造方法 Download PDFInfo
- Publication number
- JP3984167B2 JP3984167B2 JP2002561478A JP2002561478A JP3984167B2 JP 3984167 B2 JP3984167 B2 JP 3984167B2 JP 2002561478 A JP2002561478 A JP 2002561478A JP 2002561478 A JP2002561478 A JP 2002561478A JP 3984167 B2 JP3984167 B2 JP 3984167B2
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- JP
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- Prior art keywords
- iridium
- compound
- iii
- formula
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 238000004519 manufacturing process Methods 0.000 title claims 3
- 150000002504 iridium compounds Chemical class 0.000 title description 4
- 229910052751 metal Inorganic materials 0.000 title description 3
- 239000002184 metal Substances 0.000 title description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 53
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- KMGCVGZFTMILPV-UHFFFAOYSA-N iridium(3+);pentane-2,4-dione Chemical compound [Ir+3].CC(=O)CC(C)=O KMGCVGZFTMILPV-UHFFFAOYSA-N 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 9
- -1 organometallic lithium compound Chemical class 0.000 claims description 7
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- LRENBVDGVUKRKC-UHFFFAOYSA-K pyridine;trichloroiridium Chemical compound Cl[Ir](Cl)Cl.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 LRENBVDGVUKRKC-UHFFFAOYSA-K 0.000 claims description 3
- DQTGWOXKKWGIOT-UHFFFAOYSA-K thiolane;trichloroiridium Chemical compound Cl[Ir](Cl)Cl.C1CCSC1.C1CCSC1.C1CCSC1 DQTGWOXKKWGIOT-UHFFFAOYSA-K 0.000 claims description 3
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 description 17
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 238000011097 chromatography purification Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PAHNEUIHKIUNGX-UHFFFAOYSA-N 2-(3,4-difluorophenyl)pyridine Chemical compound C1=C(F)C(F)=CC=C1C1=CC=CC=N1 PAHNEUIHKIUNGX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- IAKAEIGQEHNAJA-UHFFFAOYSA-L [Ag+2].FC(F)F.[O-]S([O-])(=O)=O Chemical compound [Ag+2].FC(F)F.[O-]S([O-])(=O)=O IAKAEIGQEHNAJA-UHFFFAOYSA-L 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- PSLMOSLVUSXMDQ-UHFFFAOYSA-N iridium;pentane-2,4-dione Chemical compound [Ir].CC(=O)CC(C)=O PSLMOSLVUSXMDQ-UHFFFAOYSA-N 0.000 description 2
- 238000005649 metathesis reaction Methods 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 2
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- VJNYTMGAKLYZRS-AATRIKPKSA-N (e)-n,n,n',n'-tetramethylethene-1,2-diamine Chemical compound CN(C)\C=C\N(C)C VJNYTMGAKLYZRS-AATRIKPKSA-N 0.000 description 1
- QTQFZJSITZOKTM-UHFFFAOYSA-N CC1(C2)[O]=C(C)C=C(C)[O]2N1C Chemical compound CC1(C2)[O]=C(C)C=C(C)[O]2N1C QTQFZJSITZOKTM-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UXHPTIKOQGMSPS-UHFFFAOYSA-K Cl[Ir](Cl)(Cl)[S]1CCCC1 Chemical compound Cl[Ir](Cl)(Cl)[S]1CCCC1 UXHPTIKOQGMSPS-UHFFFAOYSA-K 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10104426A DE10104426A1 (de) | 2001-02-01 | 2001-02-01 | Verfahren zur Herstellung von hochreinen, tris-ortho-metallierten Organo-Iridium-Verbindungen |
| PCT/EP2002/000920 WO2002060910A1 (de) | 2001-02-01 | 2002-01-30 | Verfahren zur herstellung von hochreinen, tris-ortho-metallierten organo-iridium-verbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004526700A JP2004526700A (ja) | 2004-09-02 |
| JP2004526700A5 JP2004526700A5 (https=) | 2005-12-22 |
| JP3984167B2 true JP3984167B2 (ja) | 2007-10-03 |
Family
ID=7672422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002561478A Expired - Fee Related JP3984167B2 (ja) | 2001-02-01 | 2002-01-30 | 高純度のトリス−オルト−金属置換有機イリジウム化合物の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7084273B2 (https=) |
| EP (1) | EP1366054B1 (https=) |
| JP (1) | JP3984167B2 (https=) |
| KR (1) | KR100934147B1 (https=) |
| CN (2) | CN100528885C (https=) |
| DE (2) | DE10104426A1 (https=) |
| WO (1) | WO2002060910A1 (https=) |
Families Citing this family (128)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10104426A1 (de) * | 2001-02-01 | 2002-08-08 | Covion Organic Semiconductors | Verfahren zur Herstellung von hochreinen, tris-ortho-metallierten Organo-Iridium-Verbindungen |
| JP3969132B2 (ja) * | 2002-03-12 | 2007-09-05 | 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及びそれを用いた表示装置 |
| DE10238903A1 (de) * | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
| DE10249926A1 (de) * | 2002-10-26 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
| DE10314102A1 (de) * | 2003-03-27 | 2004-10-14 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung von hochreinen Organo-Iridium-Verbindungen |
| EP1717291A3 (de) | 2003-04-15 | 2007-03-21 | Merck Patent GmbH | Mischungen von organischen, zur Emission befähigten Halbleitern und Maxtrixmaterialien, deren Verwendung und diese Mischungen enthaltende Elektronikbauteile |
| DE10320103A1 (de) * | 2003-05-05 | 2004-12-02 | Basf Ag | Verfahren zur Herstellung von Phenylpyridin-Metallkomplexen und Verwendung solcher Komplexe in OLEDs |
| GB0311234D0 (en) | 2003-05-16 | 2003-06-18 | Isis Innovation | Organic phosphorescent material and organic optoelectronic device |
| US7569692B2 (en) | 2003-06-02 | 2009-08-04 | Fujifilm Corporation | Organic electroluminescent devices and metal complex compounds |
| DE10325820A1 (de) | 2003-06-07 | 2004-12-23 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung von hochreinen, tris- und bis-ortho-metallierten Organometall-Verbindungen |
| US8592614B2 (en) | 2003-07-07 | 2013-11-26 | Merck Patent Gmbh | Mixtures of organic emissive semiconductors and matrix materials, their use and electronic components comprising said materials |
| GB0321781D0 (en) | 2003-09-17 | 2003-10-15 | Toppan Printing Company Ltd | Electroluminescent device |
| DE10345572A1 (de) | 2003-09-29 | 2005-05-19 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
| DE10350606A1 (de) * | 2003-10-30 | 2005-06-09 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung heteroleptischer, ortho-metallierter Organometall-Verbindungen |
| DE10357315A1 (de) * | 2003-12-05 | 2005-07-07 | Covion Organic Semiconductors Gmbh | Organisches Elektrolumineszenzelement |
| US6870054B1 (en) * | 2003-12-05 | 2005-03-22 | Eastman Kodak Company | Synthesis for organometallic cyclometallated transition metal complexes |
| US7825249B2 (en) * | 2004-05-19 | 2010-11-02 | Merck Patent Gmbh | Metal complexes |
| US7005522B2 (en) * | 2004-06-29 | 2006-02-28 | Eastman Kodak Company | Synthesis of organometallic cyclometallated transition metal complexes |
| DE102004034517A1 (de) | 2004-07-16 | 2006-02-16 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
| TW200624435A (en) * | 2004-08-12 | 2006-07-16 | Merck Patent Gmbh | Process for preparing iridium(Ⅲ) ketoketonates |
| DE102005032332A1 (de) * | 2005-07-08 | 2007-01-11 | Merck Patent Gmbh | Metallkomplexe |
| DE102005039064A1 (de) | 2005-08-18 | 2007-03-01 | Merck Patent Gmbh | Metallkomplexe |
| CN101263151B (zh) | 2005-09-12 | 2011-09-07 | 新日铁化学株式会社 | 相同配体的邻位金属化铱配合物的制造方法 |
| DE102005057963A1 (de) * | 2005-12-05 | 2007-06-06 | Merck Patent Gmbh | Verfahren zur Herstellung ortho-metallierter Metallverbindungen |
| ATE550342T1 (de) | 2006-04-05 | 2012-04-15 | Basf Se | Heteroleptische übergangsmetall-carben-komplexe und deren verwendung in organischen leuchtdioden (oleds) |
| JP4485487B2 (ja) * | 2006-05-11 | 2010-06-23 | シャープ株式会社 | 電力増幅器 |
| WO2008031743A1 (en) | 2006-09-14 | 2008-03-20 | Ciba Holding Inc. | Heterocyclic bridged biphenyls and their use in oleds |
| US8519130B2 (en) * | 2006-12-08 | 2013-08-27 | Universal Display Corporation | Method for synthesis of iriduim (III) complexes with sterically demanding ligands |
| CN101657518A (zh) * | 2007-03-08 | 2010-02-24 | 通用显示公司 | 磷光材料 |
| US9130177B2 (en) | 2011-01-13 | 2015-09-08 | Universal Display Corporation | 5-substituted 2 phenylquinoline complexes materials for light emitting diode |
| JP5484690B2 (ja) | 2007-05-18 | 2014-05-07 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
| JP5804703B2 (ja) | 2007-07-05 | 2015-11-04 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ジシリルカルバゾール、ジシリルジベンゾフラン、ジシリルジベンゾチオフェン、ジシリルジベンゾホスホール、ジシリルジベンゾチオフェンｓ−オキシドおよびジシリルジベンゾチオフェンｓ，ｓ−ジオキシドから選択される少なくとも１つのジシリル化合物を含む有機発光ダイオード |
| US8384068B2 (en) | 2007-10-02 | 2013-02-26 | Basf Se | Use of acridine derivatives as matrix materials and/or electron blockers in OLEDs |
| WO2009073245A1 (en) * | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
| DE102008015526B4 (de) | 2008-03-25 | 2021-11-11 | Merck Patent Gmbh | Metallkomplexe |
| DE102008027005A1 (de) | 2008-06-05 | 2009-12-10 | Merck Patent Gmbh | Organische elektronische Vorrichtung enthaltend Metallkomplexe |
| CN102099942B (zh) | 2008-06-20 | 2013-05-15 | 巴斯夫欧洲公司 | 环状磷腈化合物及其在有机发光二极管中的用途 |
| EP2340579B1 (de) | 2008-10-07 | 2018-09-12 | Osram Oled Gmbh | Mit kondensierten ringsystemen substituierte silole und deren verwendung in der organischen elektronik |
| DE102009007038A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
| EP2401254B1 (de) | 2009-02-26 | 2013-06-19 | Novaled AG | Chinonverbindungen als dotierstoff in der organischen elektronik |
| JP5382887B2 (ja) | 2009-08-27 | 2014-01-08 | 独立行政法人産業技術総合研究所 | イリジウム錯体ならびに該化合物からなる発光材料 |
| JP6219443B2 (ja) * | 2009-08-31 | 2017-10-25 | ユー・ディー・シー アイルランド リミテッド | 金属錯体化合物の製造方法及び有機電界発光素子 |
| JP4551480B1 (ja) | 2009-08-31 | 2010-09-29 | 富士フイルム株式会社 | 有機電界発光素子 |
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| EP1366054B1 (de) | 2005-04-06 |
| WO2002060910A1 (de) | 2002-08-08 |
| JP2004526700A (ja) | 2004-09-02 |
| US7423151B2 (en) | 2008-09-09 |
| KR100934147B1 (ko) | 2009-12-29 |
| CN1781926A (zh) | 2006-06-07 |
| KR20030077599A (ko) | 2003-10-01 |
| CN100362004C (zh) | 2008-01-16 |
| US7084273B2 (en) | 2006-08-01 |
| DE10104426A1 (de) | 2002-08-08 |
| DE50202715D1 (de) | 2005-05-12 |
| CN100528885C (zh) | 2009-08-19 |
| US20060252936A1 (en) | 2006-11-09 |
| US20040077862A1 (en) | 2004-04-22 |
| EP1366054A1 (de) | 2003-12-03 |
| CN1527835A (zh) | 2004-09-08 |
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