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(12) United States Patent (10) Patent No.: US 8.247,086 B2 Inoue Et Al

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(12) United States Patent (10) Patent No.: US 8.247,086 B2 Inoue Et Al USOO8247086B2 (12) United States Patent (10) Patent No.: US 8.247,086 B2 Inoue et al. (45) Date of Patent: Aug. 21, 2012 (54) ORGANOMETALLIC COMPLEX AND 2009 OO15143 A1 1/2009 Inoue et al. LIGHT-EMITTING ELEMENT, 2009, O174324 A1 7, 2009 Nii et al. LIGHT-EMITTING DEVICE AND 2009, O184634 A1 7/2009 Kamatani et al. ELECTRONIC DEVICE USING THE SAME FOREIGN PATENT DOCUMENTS CN 1478.372 A 2, 2004 (75) Inventors: Hideko Inoue, Kanagawa (JP); Satoshi CN 1678617 A 10/2005 Seo, Kanagawa (JP); Nobuharu EP 1 191 612 3, 2002 EP 1 191 614 A2 3, 2002 Ohsawa, Kanagawa (JP) EP 1348711 A1 10, 2003 EP 1349 435 A1 10, 2003 (73) Assignee: Semiconductor Energy Laboratory EP 1722 602 A1 11, 2006 Co., Ltd. (JP) EP 1722 605 A1 11, 2006 EP 1881 050 A2 1, 2008 EP 1889 891 A2 2, 2008 (*) Notice: Subject to any disclaimer, the term of this JP 48-8788 A 2, 1973 patent is extended or adjusted under 35 JP 2002-105055 A 4/2002 U.S.C. 154(b) by 1183 days. JP 2002-175884. A 6, 2002 JP 2003-081988 3, 2003 JP 2005-251639 9, 2005 (21) Appl. No.: 11/607,649 JP 2005-314414 11, 2005 WO WO O2/45466 A1 6, 2002 (22) Filed: Dec. 1, 2006 WO WO 2004/O3783.6 A1 5, 2004 WO WO 2004f108857 A1 12/2004 (65) Prior Publication Data (Continued) US 2007/O129545A1 Jun. 7, 2007 OTHER PUBLICATIONS Zhang, Guo-Lin etal, Gaodeng Xuexiao Huaxue Xuebao (2004), vol. (30) Foreign Application Priority Data 25, No. 3, pp. 397-400 (with English abstract), Chemical Journal of Chinese Universities. International Search Report (Application No. PCT/JP2006/323882), Dec. 5, 2005 (JP). 2005-350807 dated Jan. 16, 2007. Written Opinion (Application No. PCT/JP2006/323882), dated Jan. (51) Int. Cl. 16, 2007. HOIL 5/54 (2006.01) Tsutsui, T. et al., “High Quantum Efficiency in Organic Light-Emit C09K II/06 (2006.01) ting Devices with Iridium-Complex as a Triplet Emissive Center.” Japanese Journal of Applied Physics, vol. 38, No. 12B, Dec. 15, 1999, (52) U.S. CI. 428/690; 428/917:313/504; 257/E51,044: pp. L1502-L1504. 544,225 (58) Field of Classification Search ........................ None (Continued) See application file for complete search history. Primary Examiner — Marie R. Yamnitzky (74) Attorney, Agent, or Firm — Husch Blackwell LLP (56) References Cited (57) ABSTRACT U.S. PATENT DOCUMENTS An organometallic complex having a structure represented by 5,484.922 A * 1/1996 Moore et al. ...................... 546,7 the general formula (G1) is synthesized and applied to a 6,780,528 B2 8/2004 Tsuboyama et al. light-emitting element. 6.821,646 B2 11/2004 Tsuboyama et al. 6,953,628 B2 10/2005 Kamatani et al. 7,094.477 B2 8/2006 Kamatani et al. (G1) 7,147,935 B2 12/2006 Kamatani et al. 7,220.495 B2 5/2007 Tsuboyama et al. 7,527,879 B2 5/2009 Kamatani et al. 7,544.426 B2 6/2009 Kamatani et al. 7,569,692 B2 8, 2009 Nii et al. 7,589,203 B2 9, 2009 Stössel et al. 7,687,155 B2 3/2010 Kamatani et al. 7,709,100 B2 5/2010 Kwong et al. 7,883,785 B2 2/2011 Stossel et al. 7,960,038 B2 6/2011 Ohsawa et al. 2001/00 19782 A1* 9/2001 Igarashi et al. ............... 428,690 2002fOO63516 A1 5/2002 Tsuboyama et al. 2002/O121638 A1 9, 2002 Grushin et al. 2003/0059646 A1 3f2003 Kamatani et al. ............. 428,690 In the formula, R' represents either an alkyl group having 1 to 2005/0O25996 A1 2/2005 Tsuboyama et al. 4 carbonatoms, an alkoxy group having 1 to 4 carbon atoms, 2005/0221123 A1 10, 2005 Inoue et al. 2006, O127696 A1 6, 2006 Stossel et al. or an alkoxycarbonyl group having 1 to 5 carbon atoms; R 2006/0177694 A1 8/2006 Kamatani et al. and Reach show either hydrogen or an alkyl group 1 to 4 2006/0228583 A1 10, 2006 Kamatani et al. carbon atoms; Arrepresents an arylene group having 6 to 25 2007/O154733 A1 7/2007 Fukuoka et al. carbon atoms; M is a center metal selected from Group 9 2007/0170843 A1 7/2007 Kawamura et al. 2007/0212570 A1 9/2007 Kamatani et al. element and Group 10 element. 2007/0216294 A1 9/2007 Kamatani et al. 35 Claims, 18 Drawing Sheets US 8.247,086 B2 Page 2 FOREIGN PATENT DOCUMENTS Covalently Attached PT II Based Antenna Units.” Chemistry—A European Journal, vol. 9, No. 21, 2003, pp. 5283-5291. WO WO 2005/086540 A1 9, 2005 Usyatinsky, A. Ya., et al. “Microwave-Assisted Synthesis of Substi WO WO 2005,115061 12/2005 tuted Imidazoles on a Solid Support Under Solvent-Free OTHER PUBLICATIONS Conditions.”Tetrahedron Letters, vol. 41, No. 26, 2000, pp. 5031 SO34. O'Brien, D.F. et al., “Improved Energy Transfer in Kidwai, M. et al. “Microwave Assisted Synthesis of Novel 1,2,4- Electrophosphorescent Devices.” Applied Physics Letters, vol. 74, Triazines in Dry Media.” Synthetic Communications, vol. 31, No. No. 3, Jan. 18, 1999, pp. 442-444. 11, 2001, pp. 1639-1645. Baldo, M.A. et al., “High-Efficiency Fluorescent Organic Light Konno, H. et al. "Selective One-Pot Synthesis of Facial Tris-Ortho Emitting Devices. Using a Phosphorescent Sensitizer.” Nature, vol. Metalated Iridium(III) Complexes. Using Microwave Irradiation.” 403, Feb. 17, 2000, pp. 750-753. Chemistry Letters, vol. 32, No. 3, 2003, pp. 252-253. Tsutsui, T. “Mechanism of Organic EL Element and Luminous Effi European Search Report reapplication No. EP 07005200.6, dated ciency.” Textbook of the 3rd Seminar at Division of Organic Molecu Jul. 23, 2007. Office Action re U.S. Appl. No. 11/092,816, dated May 20, 2010. lar Electronics and Bioelectronics, 1993, pp. 31-37, Division of European Search Report reapplication No. EP 067157024, dated Molecular Electronics and Bioelectronics, The Japan Society of Jul. 23, 2010. Applied Physics. Declaration of Satoshi Seo, filed in U.S. Appl. No. 1 1/092,816, dated Thompson, M.E. et al., “Phosphorescent Materials and Devices.” Sep. 21, 2010. Proceedings of the 10th International Workshop on Inorganic and Office Action re Chinese application No. CN 200680045339.7, dated Organic Electroluminescence (EL'00), Dec. 4, 2000, pp. 35-38. Feb. 24, 2011 (with English translation). Duan, J.-P. et al., “New Iridium Complexes as Highly Efficient Zhang. G-L et al. “Synthesis and Luminescence Property of a New Orange-Red Emitters in Organic Light-Emitting Diodes.” Advanced Yellow Phosphorescent Iridium(III) Pyrazine Complex.” Chemical Materials, vol. 15, No. 3, Feb. 5, 2003, pp. 224-228. Journal of Chinese Universities, vol. 25, No. 3, Mar. 1, 2004, pp. Zhang, G.-L. et al. “Synthesis and Phosphorescence Property of a 397-400 (with full English translation). New Pyrazine Iridium(III) Complex.” Acta Phys.-Chim. Sin., vol. 19. Yersin, H. etal, “Triplet Emitters for Organic Light-Emitting Diodes: No. 10, 2003, pp. 889-891 (with English translation). Basic Properties.” Highly Efficient OLEDs with Phosphorescent Steel, P.J. et al., “Cyclometallated Compounds v. Double Cyclopal Materials, Wiley-VCH Verlag GmbH & Co. KGaA, 2008, pp. 1-18. ladation of Diphenyl Pyrazines and Related Ligands,” Journal of Office Action re Chinese application No. CN 2007 10087859.0, dated Organometallic Chemistry, vol. 395, No. 3, 1990, pp. 359-373. Mar. 2, 2011 (with English translation). Slater, J.W. et al., “Cyclometallated Nitrogen Heterocycles,” Journal Office Action re European application No. EP067157024, dated Jun. of Organometallic Chemistry, vol. 688, Aug. 29, 2003, pp. 112-120. 24, 2011. International Search Reportre Application No. PCT/JP2006/305474, Inoue, H. et al. Basic Chemistry Course Photochemistry I (Maruzen Dated Apr. 11, 2006. Co., Ltd.), pp. 106-110, "A Reaction of Singlet Oxygen with an Written Opinion re Application No. PCT/JP2006/305474, Dated Apr. Unsaturated Organic Molecule, 6.1.4, Quencher and 11, 2006. Photosensitizer”, Sep. 30, 1999. Shavaleev, N.M. et al., “Sensitized Near-Infrared Emission from Complexes of YB III, NDIII, and ER III by Energy-Transfer from * cited by examiner U.S. Patent Aug. 21, 2012 Sheet 1 of 18 US 8,247,086 B2 FIG. 1 1 O2 115 Z 114 113 K 112 N 111 N 101 U.S. Patent Aug. 21, 2012 Sheet 2 of 18 FIG. 2 2O2 $52 ZZZZZZZZZ 217 216 215 213 N 212 N 211 20 FIG. 3 27.7///////////////23. la S-321ZZZZZZZZZZZZZZZZZZ2 uaisit Nhula U.S. Patent Aug. 21, 2012 Sheet 4 of 18 US 8.247,086 B2 LIGHT EMISSION 18 15 12 14 LN put 16c N'-46NmA Z M Z ZZ 2. (f girza Air -R %2% 16b 1 3 1 6 a t s h MW r É Z. SNNNNNSL LIGHT LIGHT FIG. 4B EMISSION EMI SS ON 18 12 14 In 1 5 A/ pUIII N III IIIf NiaNSNNNNNSNSNSNSSw Ti A1 S. 2% 27 Za 2ZZZZZ %2 % 2 2 s a r % 1 6 2 H ZANZ).al-allww. h is t 2 - --Paper-Aas7/7 22.22L-NN Sylsu -P-P-- - - - FIG. 4C 18 15 12 14 SSSSS IIISSSS SNpuID Sy 16C N - - - - - (W SNSSSSNS 1. 4% 4% 22 7 SIY- - - - 2 4% 2 5 % 16b 13 6a 2 s Al Hrr RNS SSNSF. - - - - - - - - - - - - - - - 11 10 LIGHT EMISSION U.S. Patent Aug. 21, 2012 Sheet 5 of 18 US 8,247,086 B2 533 3 S. S. S Š U.S. Patent Aug. 21, 2012 Sheet 6 of 18 US 8.247,086 B2 FIG. 6A 3. C s c al 2 d cya > (/) Z H 2.
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