Rapid combinatorial synthesis and chromatography based screening of phosphorescent iridium complexes for solution processing

Advanced Functional Materials

Volumn 22, Issue 16, 2012, Pages 3406-3413

  Hohenleutner, Andreas ^a   Schmidbauer, Susanna ^a   Vasold, Rudolf ^a   Joosten, Dominik ^b   Stoessel, Philipp ^b   Buchholz, Herwig ^b   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b MERCK KGAA   (Germany)

Author keywords

combinatorial synthesis; iridium complexes; organic light emitting diodes; phosphorescence; photodegradation; screening

Indexed keywords

CHROMATOGRAPHIC METHODS; COMBINATORIAL SYNTHESIS; IRIDIUM COMPLEX; IRRADIATION-INDUCED DEGRADATION; ORGANIC DYE; PHOTOPHYSICAL PROPERTIES; PHOTOVOLTAICS; RAPID SCREENING; RAPID SYNTHESIS; SOLUTION PROCESSABLE; SOLUTION-PROCESSING; SPECTROSCOPIC CHARACTERIZATION;

CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; DEGRADATION; IRIDIUM; LIGHT EMISSION; METAL COMPLEXES; ORGANIC LIGHT EMITTING DIODES (OLED); PHOSPHORESCENCE; PHOTODEGRADATION; SCREENING; SYNTHESIS (CHEMICAL);

IRIDIUM COMPOUNDS;

EID: 84865106463     PISSN: 1616301X     EISSN: 16163028     Source Type: Journal    
DOI: 10.1002/adfm.201200397     Document Type: Article

References (55)

1. a) K. K.-W. Lo, C.-K. Chung, T. K.-M. Lee, L.-H. Lui, K. H.-K. Tsang, N. Zhu, Inorg. Chem. 2003, 42, 6886
2. b) K. K.-W. Lo, D. C.-M. Ng, C.-K. Chung, Organometallics 2001, 20, 4999
3. c) K. K.-W. Lo, K. Y. Zhang, S.-K. Leung, M.-C. Tang, Angew. Chem. Int. Ed. 2008, 47, 2213.
4. a) C. S. K. Mak, D. Pentlehner, M. Stich, O. S. Wolfbeis, W. K. Chan, H. Yersin, Chem. Mater. 2009, 21, 2173
5. b) Y. You, S. Y. Park, Adv. Mater. 2008, 20, 3820.
6. a) W. Zhao, F. N. Castellano, J. Phys. Chem. A 2006, 110, 11440
7. b) T. N. Singh-Rachford, F. N. Castellano, Coord. Chem. Rev. 2010, 254, 2560.
8. E. Baranoff, J.-H. Yum, M. Graetzel, M. K. Nazeeruddin, J. Organomet. Chem. 2009, 694, 2661.
9. a) B. F. DiSalle, S. Bernhard, J. Am. Chem. Soc. 2011, 133, 11819
10. b) J. I. Goldsmith, W. R. Hudson, M. S. Lowry, T. H. Anderson, S. Bernhard, J. Am. Chem. Soc. 2005, 127, 7502
11. c) N. Sutin, C. Creutz, E. Fujita, Comments Inorg. Chem. 1997, 19, 67
12. d) Y.-J. Yuan, Z.-T. Yu, X.-Y. Chen, J.-Y. Zhang, Z.-G. Zou, Chem. -Eur. J. 2011, 17, 12891.
13. a) K. Zeitler, Angew. Chem., Int. Ed. 2009, 48, 9785
14. b) H.-W. Shih, M. N. Vander Wal, R. L. Grange, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 13600
15. c) A. G. Condie, J. C. González-Gõmez, C. R. J. Stephenson, J. Am. Chem. Soc. 2010, 132, 1464.
16. M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151.
17. a) T. Hofbeck, H. Yersin, Inorganic Chemistry 2010, 49, 9290
18. b) H. Yersin, A. F. Rausch, R. Czerwieniec, T. Hofbeck, T. Fischer, Coord. Chem. Rev. 2011, 255, 2622.
19. a) Y. You, S. Y. Park, Dalton Trans. 2009, 1267
20. b) Y. Chi, P.-T. Chou, Chem. Soc. Rev. 2010, 39, 638
21. c) P. T. Chou, Y. Chi, Chem. -Eur. J. 2007, 13, 380.
22. a) E. Baranoff, S. Fantacci, F. De Angelis, X. Zhang, R. Scopelliti, M. Grätzel, M. K. Nazeeruddin, Inorg. Chem. 2010, 50, 451
23. b) F. De Angelis, S. Fantacci, N. Evans, C. Klein, S. M. Zakeeruddin, J.-E. Moser, K. Kalyanasundaram, H. J. Bolink, M. Grätzel, M. K. Nazeeruddin, Inorg. Chem. 2007, 46, 5989
24. c) C. L. Ho, W. Y. Wong, Z. Q. Gao, C. H. Chen, K. W. Cheah, B. Yao, Z. Y. Xie, Q. Wang, D. G. Ma, L. X. Wang, X. M. Yu, H. S. Kwok, Z. Y. Lin, Adv. Funct. Mater. 2008, 18, 319
25. d) J. Li, P. I. Djurovich, B. D. Alleyne, M. Yousufuddin, N. N. Ho, J. C. Thomas, J. C. Peters, R. Bau, M. E. Thompson, Inorg. Chem. 2005, 44, 1713
26. e) M. S. Lowry, W. R. Hudson, R. A. Pascal, S. Bernhard, J. Am. Chem. Soc. 2004, 126, 14129.
27. E. M. Gordon, R. W. Barrett, W. J. Dower, S. P. A. Fodor, M. A. Gallop, J. Med. Chem. 1994, 37, 1385.
28. C. Gennari, U. Piarulli, Chem. Rev. 2003, 103, 3071.
29. N.-M. Hsu, W.-R. Li, Angew. Chem., Int. Ed. 2006, 45, 4138.
30. E. Baranoff, I. Jung, R. Scopelliti, E. Solari, M. Grätzel, M. K. Nazeeruddin, Dalton Trans. 2011, 40, 6860.
31. a) C. E. Kibbey, Lab. Rob. Autom. 1997, 9, 309
32. b) L. Zeng, L. Burton, K. Yung, B. Shushan, D. B. Kassel, J. Chromatogr., A 1998, 794, 3
33. c) H. N. Weller, Mol. Diversity 1998, 4, 47.
34. a) C. Adachi, M. A. Baldo, S. R. Forrest, M. E. Thompson, Appl. Phys. Lett. 2000, 77, 904
35. b) Y. Kawamura, K. Goushi, J. Brooks, J. J. Brown, H. Sasabe, C. Adachi, Appl. Phys. Lett. 2005, 86, 071104.
36. D. Tanaka, H. Sasabe, Y.-J. Li, S.-J. Su, T. Takeda, J. Kido, Jpn. J. Appl. Phys. 2007, 46, L10.
37. a) N. Cumpstey, R. N. Bera, P. L. Burn, I. D. W. Samuel, Macromolecules 2005, 38, 9564
38. b) Y. You, C.-G. An, J.-J. Kim, S. Y. Park, J. Org. Chem. 2007, 72, 6241
39. c) Y. You, C.-G. An, D.-S. Lee, J.-J. Kim, S. Y. Park, J. Mater. Chem. 2006, 16, 4706.
40. P. Stoessel, H. Spreitzer, H. Becker, Rhodium and Iridium Complexes, WO02068435A1, Covion Organic Semiconductors, 2002.
41. a) P. Stoessel, I. Bach, H. Spreitzer, Rhodium and Iridium Complexes, WO200402 6886A2, Covion Organic Semiconductors, 2004
42. b) P. Stoessel, H. Spreitzer, H. Becker, Rhodium and Iridium Complexes WO02081488A1, Covion Organic Semiconductors, 2002
43. c) R. M. Anemian, B. Schroeder, A. H. Parham, C. d. Nonancourt, Metal Complexes, WO2011141120A1, Merck Patent GmbH, 2011.
44. K. Ono, M. Joho, K. Saito, M. Tomura, Y. Matsushita, S. Naka, H. Okada, H. Onnagawa, Eur. J. Inorg. Chem. 2006, 2006, 3676.
45. Y. You, K. S. Kim, T. K. Ahn, D. Kim, S. Y. Park, J. Phys. Chem. C 2007, 111, 4052.
46. a) N. C. Giebink, B. W. D'Andrade, M. S. Weaver, J. J. Brown, S. R. Forrest, J. Appl. Phys. 2009, 105, 124514
47. b) N. C. Giebink, B. W. D'Andrade, M. S. Weaver, P. B. Mackenzie, J. J. Brown, M. E. Thompson, S. R. Forrest, J. Appl. Phys. 2008, 103, 044509
48. c) R. Seifert, S. Scholz, B. Lussem, K. Leo, Appl. Phys. Lett. 2010, 97, 013308.
49. a) T. Sajoto, P. I. Djurovich, A. B. Tamayo, J. Oxgaard, W. A. Goddard, M. E. Thompson, J. Am. Chem. Soc. 2009, 131, 9813
50. b) I. R. d. Moraes, S. Scholz, B. Lüssem, K. Leo, Org. Electron. 2011, 12, 341.
51. W. Sotoyama, T. Satoh, M. Kinoshita, M. Tobise, K. Kawato, T. Ise, H. Takizawa, S. Yamashita, Fujifilm Research and Development 2010, No. 055, 24.
52. a) R. Gao, D. G. Ho, B. Hernandez, M. Selke, D. Murphy, P. I. Djurovich, M. E. Thompson, J. Am. Chem. Soc. 2002, 124, 14828
53. b) S.-y. Takizawa, R. Aboshi, S. Murata, Photochem. Photobiol. Sci. 2011, 10, 895
54. c) P. I. Djurovich, D. Murphy, M. E. Thompson, B. Hernandez, R. Gao, P. L. Hunt, M. Selke, Dalton Trans. 2007, 3763.
55. P. Stoessel, H. Spreitzer, H. Becker, Method for the Production of Highly Pure, Tris-ortho Metalated Organo-Iridium Compounds, WO02060910A1, 2002.