Source: http://www.google.com/patents/US7947383?dq=6,332,126
Timestamp: 2017-12-18 09:22:05
Document Index: 330888067

Matched Legal Cases: ['§119', 'Application No. 2004', 'Application No. 2005', 'Application No. 2005', 'Application No. 2004', 'Application No. 2005', 'Application No. 2007']

Patent US7947383 - Organic electroluminescent device - Google Patents
An organic electroluminescent device having a pair of electrodes and at least one organic layer including a light-emitting layer interposed between the pair of electrodes, in which the organic layer contains at least one compound represented by formula (I): wherein Z1 and Z2 each independently represent...http://www.google.com/patents/US7947383?utm_source=gb-gplus-sharePatent US7947383 - Organic electroluminescent device
Publication number US7947383 B2
Application number US 11/663,164
PCT number PCT/JP2005/017660
Also published as EP1808052A1, EP1808052B1, EP1808052B2, US20080001530, WO2006033440A1
Publication number 11663164, 663164, PCT/2005/17660, PCT/JP/2005/017660, PCT/JP/2005/17660, PCT/JP/5/017660, PCT/JP/5/17660, PCT/JP2005/017660, PCT/JP2005/17660, PCT/JP2005017660, PCT/JP200517660, PCT/JP5/017660, PCT/JP5/17660, PCT/JP5017660, PCT/JP517660, US 7947383 B2, US 7947383B2, US-B2-7947383, US7947383 B2, US7947383B2
Inventors Toshihiro Ise, Seiji Ichijima, Takeshi Murakami, Satoshi Sano
Patent Citations (56), Non-Patent Citations (9), Referenced by (24), Classifications (24), Legal Events (3)
US 7947383 B2
11. The organic electroluminescent device according to claim 2, wherein at least one of the compound represented by formula (II) and at least one host material are contained in the light-emitting layer.
The glass transition point of the host material is preferably 100° C. or more and 500° C. or less, more preferably 110° C. or more and 300° C. or less, and still more preferably 120° C. or more and 250° C. or less.
The external quantum efficiency of the light-emitting device of the present invention is preferably 5% or more, more preferably 10% or more, and still more preferably 15%, or more. As the value of the external quantum efficiency, the maximum value of the external quantum efficiency when the device is driven at 25° C. or the value of the external quantum efficiency at a luminance close to 300 to 2000 cd/m2 when the device is driven at 25° C. can be used.
EXAMPLES Synthetic Examples Synthesis of the Exemplified Compound 4
Under a nitrogen flow, 390 mg of the ligand 4 and 239 mg of platinous chloride were suspended in 5 mL of benzonitrile, and the mixture was raised up to 200° C. and heated for 3 hours. The reaction mixture was cooled to a room temperature, and hexane was then added to the mixture, to obtain precipitates. These precipitates were collected by filtration and then purified by using a silica gel column (eluent: chloroforin), to obtain 320 mg of the exemplified compound 4 (yield: 57%).
The ligand 182 was synthesized using SM as a starting material by a known organic synthetic method. Under a nitrogen atmosphere, 300 mg of the ligand 182 and 210 mg of platinous chloride were suspended in 6 mL of benzonitrile, and the mixture was heated to 150° C. and stirred at the temperature for 6 hours. After the reaction was finished, hexane was added to the reaction mixture, and the precipitated solid was heated in a mixed solvent of chloroform and methanol. The solid precipitated by cooling was collected by filtration, to obtain 200 mg of the exemplified compound 182 (yield: 44%).
The ligand 5 was synthesized using SM as a starting material by a known organic synthetic method. Under a nitrogen atmosphere, 350 mg of the ligand 5 and 210 mg of platinous chloride were suspended in 4 mL of benzonitrile, and the mixture was heated to 120° C. and stirred at the temperature for 6.5 hours. After the reaction was finished, hexane was added to the reaction mixture, and the precipitated solid was heated in a mixed solvent of chloroform and methanol. The solid precipitated by cooling was collected by filtration, to obtain 430 mg of the exemplified compound 5 (yield: 86%).
The ligand 6 was synthesized using SM as a starting material by a known organic synthetic method. Under a nitrogen atmosphere, 64 mg of the ligand 6 and 39 mg of platinous chloride were suspended in 3 mL of benzonitrile, and the mixture was stirred at 120° C. for 3 hours and then further stirred at 150° C. for 2.5 hours. After the reaction was finished, hexane was added to the reaction mixture, and the precipitated solid was purified by using a silica gel chromatography (eluent: chloroform/methanol=10/1), to obtain 48 mg of the exemplified compound 6 (yield: 52%).
The ligand 7 was synthesized using SM as a starting material by a known organic synthetic method. Under a nitrogen flow, 390 mg of the ligand 7 and 293 mg of platinous chloride were suspended in 5 mL of benzonitrile, and the mixture was raised up to 200° C. and heated for 3 hours. The reaction mixture was cooled to a room temperature, and hexane was then added to the mixture, to obtain precipitates. These precipitates were collected by filtration and then purified by using a silica gel column (eluent: chloroform), to obtain 488 mg of the exemplified compound 7 (yield: 81%).
The ligand 213 was synthesized by a known organic synthetic method. Under a nitrogen flow, 45 mg of the ligand 213 and 66 mg of platinous chloride were suspended in 5 mL of benzonitrile, and the mixture was raised up to 200° C. and heated for 3 hours. The reaction mixture was cooled to a room temperature, and hexane was then added to the mixture, to obtain precipitates. These precipitates were collected by filtration and then purified by using a silica gel column (eluent: chloroform), to obtain 35 mg of the exemplified compound 213 (yield: 53%).
Organic EL Device Comparative Example 1
A cleaned ITO substrate was placed in a vacuum deposition apparatus, and NPD was vacuum-deposited thereon in a thickness of 50 nm. Further, CBP and Ir(ppy)3 were vacuum-deposited thereon in a thickness of 40 nm with a mass ratio of 10:1, and Balq was vacuum-deposited thereon in a thickness of 10 nm, and, further, Alq was vacuum-deposited thereon in a thickness of 30 nm. On the thus-obtained organic thin film, a patterned mask (light-emitting area: 4 mm×5 mm) was provided. After vacuum-depositing lithium fluoride in a thickness of 3 nm, aluminum was vacuum-deposited thereon in a thickness of 60 nm, to prepare an organic EL device of the comparative example 1. When a direct current constant voltage was applied to the thus-obtained organic EL device, green color emission having an emission maximum wavelength λmax of 514 nm was observed, and the external quantum efficiency of the organic EL device was 6.4%.
Light-emitting device Luminance half time
Comparative example 1 85 hours
This invention 1 470 hours
This invention 2 510 hours
This invention 3 534 hours
This invention 4 463 hours
This invention 5 391 hours
This invention 6 580 hours
This non-provisional application claims priority under 35 U.S.C. §119 (a) on Patent Application No. 2004-275915 filed in Japan on Sep. 22, 2004, Patent Application No. 2005-41939 filed in Japan on Feb. 18, 2005, and Patent Application No. 2005-162376 filed in Japan on Jun. 2, 2005, each of which is entirely herein incorporated by reference.
US7566505 * Mar 31, 2005 Jul 28, 2009 Fujifilm Corporation Organic electroluminescent element
US7579093 * Sep 16, 2005 Aug 25, 2009 Fujifilm Corporation Organic electroluminescent device
US20020008233 Jul 25, 2001 Jan 24, 2002 Forrest Stephen R. Intersystem crossing agents for efficient utilization of excitions in organic light emitting devices
US20020013306 Jan 24, 1997 Jan 31, 2002 Gordon Lowe Terpyridine-platinum(ii) complexes
US20020068190 Sep 24, 2001 Jun 6, 2002 Akira Tsuboyama Luminescence device and metal coordination compound therefor
US20030203236 Apr 30, 2003 Oct 30, 2003 Thompson Mark E. OLEDs doped with phosphorescent compounds
US20030205707 May 1, 2002 Nov 6, 2003 Che Chi-Ming Electroluminescent materials
US20060073359 Sep 26, 2005 Apr 6, 2006 Fuji Photo Film Co., Ltd. Light-emitting device
US20060182992 Jun 1, 2004 Aug 17, 2006 Kazumi Nii Organic electroluminescent devices and metal complex compounds
US20060264625 Apr 4, 2004 Nov 23, 2006 Yuji Nakayama Platinum complex
US20060286406 Apr 25, 2006 Dec 21, 2006 Fuji Photo Film Co., Ltd. Organic electroluminescent device
US20070082284 Oct 21, 2004 Apr 12, 2007 Merck Patent Gmbh Metal complexes with bipodal ligands
US20070103060 Oct 27, 2004 May 10, 2007 Takasago International Corporation Platinum complex and light emitting device
US20080001530 Sep 20, 2005 Jan 3, 2008 Toshihiro Ise Organic Electroluminescent Device
US20080036373 Aug 8, 2007 Feb 14, 2008 Takasago International Corporation Platinum complex and light-emitting device
US20090128008 Mar 16, 2006 May 21, 2009 Fujifilm Corporation Platinum complex compound and organic electroluminescent device
EP0969532A2 Jun 21, 1999 Jan 5, 2000 Bayer Aktiengesellschaft Electroluminescent devices using metal complexes of azomethine
JP4110173B2 Title not available
JP2000048960A Title not available
JP2000503982A Title not available
JP2001338768A Title not available
JP2002175884A Title not available
JP2002363552A Title not available
JP2003123976A Title not available
JP2003123981A Title not available
JP2004331508A Title not available
JP2005220136A Title not available
JP2005310733A Title not available
JP2006093542A Title not available
JP2006120811A Title not available
JP2006190718A Title not available
JP2006256999A Title not available
JP2006261623A Title not available
JP2006332620A Title not available
JP2007019462A Title not available
JP2007073845A Title not available
JP2007519614A Title not available
JP2008037848A Title not available
JP2008103535A Title not available
JP2008524848A Title not available
KR20060115371A Title not available
WO2004039914A1 Oct 24, 2003 May 13, 2004 Takasago International Corporation Luminescents
WO2005042444A2 Oct 27, 2004 May 12, 2005 Takasago Perfumery Co Ltd Platinum complex and luminescent element
1 Chem. Eur. J. 9(6), pp. 1263-1272 (2003).
2 Fritsky et al., Angewandte Chemie, International Edition, vol. 39, No. 18, p. 3255-3258 (2000).
3 Japanese Office Action and Translation issued in corresponding Japanese Application No. 2004-279153, (dated Nov. 11, 2009).
4 Japanese Office Action and Translation issued on Nov. 17, 2009 in corresponding Japanese Patent Application No. 2005-162376.
5 Korean Office Action and Translation issued on Jan. 19, 2011 in corresponding Korean Patent Application No. 2007-7006569.
6 Nature 395, pp. 151-154, Baldo et al. (1998).
7 Newkome et al., Organometallics, vol. 7, No. 12, p. 2537-2542 (1988).
8 Office Action dated Jun. 8, 2010 in corresponding JP 2010-008589 application with English translation.
9 Yip J H K et al., Inorganic Chemistry, American Chemical Society, vol. 39, 2000, pp. 3537-3543 XP002324504.
US8946417 * Apr 6, 2010 Feb 3, 2015 Arizona Board Of Regents Acting For And On Behalf Of Arizona State University Synthesis of four coordinated platinum complexes and their applications in light emitting devices thereof
US9193747 * Jan 6, 2010 Nov 24, 2015 Udc Ireland Limited Organic electroluminescent device
US9818959 Jul 27, 2015 Nov 14, 2017 Arizona Board of Regents on behlaf of Arizona State University Metal-assisted delayed fluorescent emitters containing tridentate ligands
US20100171111 * Jan 6, 2010 Jul 8, 2010 Fujifilm Corporation Organic electroluminescent device
US20120095232 * Apr 6, 2010 Apr 19, 2012 Jian Li Synthesis of four coordinated platinum complexes and their applications in light emitting devices thereof
U.S. Classification 428/690, 257/E51.044, 313/504, 428/917, 313/506
Cooperative Classification H05B33/14, H01L51/5016, H01L51/0087, H01L51/0081, H01L51/0078, H01L51/0071, H01L51/006, C09K2211/185, C09K2211/1092, C09K2211/1059, C09K2211/1044, C09K2211/1029, C09K11/06, Y10S428/917
European Classification C09K11/06, H05B33/14, H01L51/00M12F6
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ISE, TOSHIHIRO;ICHIJIMA, SEIJI;MURAKAMI, TAKESHI;AND OTHERS;REEL/FRAME:019118/0142;SIGNING DATES FROM 20070215 TO 20070217
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ISE, TOSHIHIRO;ICHIJIMA, SEIJI;MURAKAMI, TAKESHI;AND OTHERS;SIGNING DATES FROM 20070215 TO 20070217;REEL/FRAME:019118/0142