Bimetallic Cyclometalated Iridium(III) Diastereomers with Non-Innocent Bridging Ligands for High-Efficiency Phosphorescent OLEDs†
Dr. Yonghao Zheng
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Andrei S. Batsanov
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Mark A. Fox
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Hameed A. Al-Attar
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorKhalid Abdullah
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Vygintas Jankus
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorCorresponding Author
Prof. Martin R. Bryce
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Department of Chemistry, Durham University, Durham DH1 3LE (UK)Search for more papers by this authorProf. Andrew P. Monkman
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Yonghao Zheng
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Andrei S. Batsanov
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Mark A. Fox
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Hameed A. Al-Attar
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorKhalid Abdullah
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorDr. Vygintas Jankus
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorCorresponding Author
Prof. Martin R. Bryce
Department of Chemistry, Durham University, Durham DH1 3LE (UK)
Department of Chemistry, Durham University, Durham DH1 3LE (UK)Search for more papers by this authorProf. Andrew P. Monkman
Department of Physics, Durham University, Durham DH1 3LE (UK)
Search for more papers by this authorWe thank the EPSRC for funding and Dr. E. Pohl for access to the Bruker MicroStar rotating anode.
Abstract
Two phosphorescent dinuclear iridium(III) diastereomers (ΛΔ/ΔΛ) and (ΛΛ/ΔΔ) are readily separated by making use of their different solubilities in hot hexane. The bridging diarylhydrazide ligand plays an important role in the electrochemistry and photophysics of the complexes. Organic light-emitting devices (OLEDs) that use these complexes as the green-emissive dopants in solution-processable single-active-layer architectures feature electroluminescence efficiencies that are remarkably high for dinuclear metal complexes, achieving maximum values of 37 cd A−1, 14 lm W−1, and 11 % external quantum efficiency.
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References
- 1
- 1a Organic Light-Emitting Devices (Eds.: ), Wiley-VCH, Weinheim, 2006;
- 1b Highly Efficient OLEDs with Phosphorescent Materials (Ed.: ), Wiley-VCH, Weinheim, 2008, chap. 8;
- 1cS. Y. Lee, T. Yasuda, Y. S. Yang, Q. Zhang, C. Adachi, Angew. Chem. Int. Ed. 2014, 53, 6402–6406; Angew. Chem. 2014, 126, 6520–6524.
- 2For a review, see:
- 2aK. T. Kamtekar, A. P. Monkman, M. R. Bryce, Adv. Mater. 2010, 22, 572–582; for an example, see:
- 2bW.-X. Ni, M. Li, J. Zheng, S.-Z. Zhan, Y.-M. Qiu, S. W. Ng, D. Li, Angew. Chem. Int. Ed. 2013, 52, 13472–13476; Angew. Chem. 2013, 125, 13714–13718.
- 3M. A. Baldo, D. F. O’Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151–154.
- 4Y. Kawamura, K. Goushi, J. Brooks, J. J. Brown, H. Sasabe, C. Adachi, Appl. Phys. Lett. 2005, 86, 071104.
- 5X.-C. Hang, T. Fleetham, E. Turner, J. Brooks, J. Li, Angew. Chem. Int. Ed. 2013, 52, 6753–6756; Angew. Chem. 2013, 125, 6885–6888.
- 6S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H.-E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304–4312.
- 7For a review, see: E. Holder, B. M. W. Langeveld, U. S. Schubert, Adv. Mater. 2005, 17, 1109–1121.
- 8For a review, see: L. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong, J. Kido, Adv. Mater. 2011, 23, 926–952.
- 9N. Tian, D. Lenkeit, S. Pelz, D. Kourkoulos, D. Hertel, K. Meerholz, E. Holder, Dalton Trans. 2011, 40, 11629–11635.
- 10D. Xia, B. Wang, B. Chen, S. Wang, B. Zhang, J. Ding, L. Wang, X. Jing, F. Wang, Angew. Chem. Int. Ed. 2014, 53, 1048–1052; Angew. Chem. 2014, 126, 1066–1070.
- 11G. A. Carlson, P. I. Djurovich, R. J. Watts, Inorg. Chem. 1993, 32, 4483–4484.
- 12A. Tsuboyama, T. Takiguchi, S. Okada, M. Osawa, M. Hoshino, K. Ueno, Dalton Trans. 2004, 1115–1116.
- 13E. A. Plummer, J. W. Hofstraat, L. De Cola, Dalton Trans. 2003, 2080–2084.
- 14A. Santoro, A. M. Prokhorov, V. N. Kozhevnikov, A. C. Whitwood, B. Donnio, J. A. G. Williams, D. W. Bruce, J. Am. Chem. Soc. 2011, 133, 5248–5251.
- 15V. Chandrasekhar, S. M. W. Rahaman, T. Hajra, D. Das, T. Ghatak, S. Rafiq, P. Sen, J. K. Bera, Chem. Commun. 2011, 47, 10836–10838.
- 16E. S. Andreiadis, D. Imbert, J. Pécaut, A. Calborean, I. Ciofini, C. Adamo, R. Demadrille, M. Mazzanti, Inorg. Chem. 2011, 50, 8197–8206.
- 17E. Baranoff, E. Orselli, L. Allouche, D. Di Censo, R. Scopelliti, M. Grätzel, M. D. Nazeeruddin, Chem. Commun. 2011, 47, 2799–2801.
- 18V. Chandrasekhar, T. Hajra, J. K. Bera, S. M. W. Rahaman, N. Satumitra, O. Elbjeirami, M. A. Omary, Inorg. Chem. 2012, 51, 1319–1329.
- 19V. Chandrasekhar, B. Mahanti, P. Bandipalli, K. Bhanuprakash, Inorg. Chem. 2012, 51, 10536–10547.
- 20V. L. Whittle, J. A. G. Williams, Inorg. Chem. 2008, 47, 6596–6607.
- 21A. Auffrant, A. Barbieri, F. Barigelletti, J. Lacour, P. Mobian, J.-P. Collin, J.-P. Sauvage, B. Ventura, Inorg. Chem. 2007, 46, 6911–6919.
- 22M. Graf, R. Czerwieniec, K. Sünkel, Z. Anorg. Allg. Chem. 2013, 639, 1090–1094.
- 23L. Donato, C. E. McCusker, F. N. Castellano, E. Zysman-Colman, Inorg. Chem. 2013, 52, 8495–8504.
- 24A. M’hamedi, A. S. Batsanov, M. A. Fox, M. R. Bryce, K. Abdullah, H. A. Al-Attar, A. P. Monkman, J. Mater. Chem. 2012, 22, 13529–13540.
- 25P.-H. Lanoë, C. M. Tong, R. W. Harrington, M. R. Probert, W. Clegg, J. A. G. Williams, V. N. Kozhevnikov, Chem. Commun. 2014, 50, 6831–6834.
- 26S. Bettington, M. Tavasli, M. R. Bryce, A. S. Batsanov, A. L. Thompson, H. A. Al Attar, F. B. Dias, A. P. Monkman, J. Mater. Chem. 2006, 16, 1046–1052.
- 27X. Li, D. Zhang, W. Li, B. Chu, L. Han, T. Li, Z. Su, J. Zhu, Y. Chen, Z. Hu, P. Lei, Z. Zhang, Opt. Mater. 2009, 31, 1173–1176.
- 28K. A. King, P. J. Spellane, R. J. Watts, J. Am. Chem. Soc. 1985, 107, 1431–1432.
- 29V. W.-W. Yam, K. M.-C. Wong, Chem. Commun. 2011, 47, 11579–11592.
- 30
- 30aC. Schaffner-Hamann, A. von Zelewsky, A. Barbieri, F. Barigelletti, G. Muller, J. P. Riehl, A. Neels, J. Am. Chem. Soc. 2004, 126, 9339–9348;
- 30bC. Hamann, A. von Zelewsky, A. Neels, H. Stoeckli-Evans, Dalton Trans. 2004, 402–406;
- 30cF. J. Coughlin, M. S. Westrol, K. D. Oyler, N. Byrne, C. Kraml, E. Zysman-Colman, M. S. Lowry, S. Bernhard, Inorg. Chem. 2008, 47, 2039–2048;
- 30dE. Marchi, R. Sinisi, G. Bergamini, M. Tragni, M. Monari, M. Bandini, P. Ceroni, Chem. Eur. J. 2012, 18, 8765–8773.
- 31CCDC 995196 (complex 3), 995198 (complex 4), and 995197 (complex 5) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 32A. M. Soliman, D. Fortin, P. D. Harvey, E. Zysman-Colman, Dalton Trans. 2012, 41, 9382–9393.
- 33H. A. Al-Attar, G. C. Griffiths, T. N. Moore, M. Tavasli, M. A. Fox, M. R. Bryce, A. P. Monkman, Adv. Funct. Mater. 2011, 21, 2376–2382.
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