2,7-Bis(diarylamino)-9,9-dimethylfluorenes as Hole-Transport Materials for Organic Light-Emitting Diodes

Advanced Functional Materials

Volumn 13, Issue 12, 2003, Pages 967-973

  Hreha, Richard D ^a   George, Candace P ^a   Haldi, Andreas ^b   Domercq, Benoit ^b,d   Malagoli, Massimo ^a   Barlow, Stephen ^a,c   Brédas, Jean Luc ^a,c   Kippelen, Bernard ^b,d   Marder, Seth R ^a,b,c  

^a University of Arizona   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

^c GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^d GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; ELECTRON TRANSITIONS; FLUORESCENCE; IONIZATION; LIGHT EMITTING DIODES; OXIDATION; PALLADIUM; POLYMER BLENDS; POLYSTYRENES; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY;

FLUORENE; HOLE-TRANSPORT;

AROMATIC COMPOUNDS;

EID: 0346907277     PISSN: 1616301X     EISSN: None     Source Type: Journal    
DOI: 10.1002/adfm.200304464     Document Type: Article

References (46)

1. D. M. Pai, B. E. Springett, Rev. Mod. Phys. 1993, 65, 163.
2. P. M. Borsenberger, D. S. Weiss, Organic Photoreceptors for Xerography, Marcel Dekker, New York 1998.
3. C. W. Tang, S. A. Van Slyke, Appl. Phys. Lett. 1987, 51, 913.
4. J. Shi, C. W. Tang, Appl. Phys. Lett. 1997, 70, 1665.
5. Y. Shirota, K. Okumoto, H. Inada, Synth. Met. 2000, 111-112, 387.
6. J. Kido, M. Kimura, K. Nagai, Science 1995, 267, 1332.
7. M. Strukelj, R. H. Jordan, A. Dodabalapur, J. Am. Chem. Soc. 1996, 124, 1213.
8. A. W. Grice, D. D. C. Bradley, M. T. Bernius, M. Inbasekaran, W. W. Wu, E. P. Woo, Appl. Phys. Lett. 1998, 73, 629.
9. D. F. O'Brien, P. Burrows, S. R. Forrest, B. E. Koene, D. Loy, M. E. Thompson, Adv. Mater. 1998, 10, 1108.
10. E. Bellmann, S. E. Shaheen, R. H. Grubbs, S. R. Marder, B. Kippelen, N. Peyghambarian, Chem. Mater. 1999, 11, 399.
11. C. F. Qiu, L. D. Wang, H. Y. Chen, M. Wong, H. S. Kwok, Appl. Phys. Lett. 2001, 79, 2276.
12. J. Thompson, R. I. Blyth, M. Mazzeo, M. Anni, G. Gigli, R. Cingolaniers, Appl. Phys. Lett. 2001, 79, 560.
13. B. Domercq, R. D. Hreha, Y.-D. Zhang, N. Larribeau, J. N. Haddock, C. Schnitz, S. R. Marder, B. Kippelen, Chem. Mater. 2003, 15, 1491.
14. D. E. Loy, B. E. Koene, M. E. Thompson, Adv. Funct. Mater. 2002, 12, 245.
15. K.-T. Wong, Z.-J. Wang, Y.-Y. Chien, C.-L. Wang, Org. Lett. 2001, 3, 2285.
16. 9,9-Dimethylfluoren-2-yl groups have also been used to replace the aryl end groups of TPD-like molecules, and this strategy has also been found to raise glass-transition temperatures: values of 131 and 165 °C were found for 2,7-bis[N-(9-dimethylfluoren-2-yl)-N-phenylamino]-9,9-dimethylfluorene and 4′,4′-bis[di(9-dimethylfluoren-2-yl)ammo]biphenyl, respectively [18]. K. Okumoto, Y. Shirota, Chem. Lett. 2000, 1034.
17. Y. Hashimoto, M. Hamagaki, T. Sakakibara, Jpn. J. Appl. Phys. 2001, 40, 4720.
18. K. Okumoto, Y. Shirota, Mater. Sci. Eng. 2001, B85, 135.
19. R. D. Hreha, A. Haldi, B. Domercq, M. Malagoli, S. Barlow, J.-L. Brédas, B. Kippelen, S. R. Marder, unpublished.
20. K. D. Belfield, K. J. Schafer, W. Mourad, B. A. Reinhardt, J. Org. Chem. 2000, 4475.
21. M. Malagoli, J.-L. Brédas, Chem. Phys. Lett. 2000, 327, 13.
22. M. Watanabe, T. Yamamoto, S. Nishiyama, Y. Koie, Japanese Patent JP 11 322 679, 1999.
23. D. Baranano, G. Mann, J. F. Hartwig, Curr. Org. Chem. 1997, 1, 287.
24. B. H. Yang, S. L. Buchwald, J. Organomet. Chem. 1999, 576, 125.
25. R. D. Hreha, Y.-D. Zhang, B. Domercq, N. Larribeau, J. N. Haddock, B. Kippelen, S. R. Marder, Synthesis 2002, 1201.
26. G. Hallas, J. D. Hepworth, D. R. Waring, J. Chem. Soc. B 1970, 975.
27. N. Kikuchi, A. Maruyama, Japanese Patent JP 09281728, 1997.
28. K. Suzuki, T. Kaeamaru, K. Nakata, N. Kikuchi, K. Nakamura, Japanese Patent JP 10069108, 1998.
29. S. Thayumanavan, S. Barlow, S. R. Marder, Chem. Mater. 1997, 9, 3231.
30. K. Naito, A. Miura, J. Phys. Chem. 1993, 97, 6240.
31. J. D. Anderson, E. M. McDonald, P. A. Lee, M. L. Anderson, E. L. Ritchie, H. K. Hall, T. Hopkins, E. A. Nash, J. Wang, A. Padias, S. Thayumanavan, S. Barlow, S. R. Marder, G. Jabbour, S. Shaheen, B. Kippelen, N. Peyghambarian, R. M. Wightaan, N. R. Armstrong, J. Am. Chem. Soc. 1998, 120, 9646.
32. W. Holzer, A. Penzkofer, H.-H. Horhold, Synth. Met. 2000, 113, 281.
33. H. Bässler, Phys. Status Solidi B 1993, 175, 15.
34. P. M. Borsenberger, E. H. Magin, M. van der Auweraer, F. C. de Schryver, Phys. Status Solidi A 1993, 140, 9.
35. H. Bässler, Mol. Cryst. Liq. Cryst. 1994, 252, 11.
36. J.-L. Maldonado, M. Bishop, C. Fuentes-Hernandez, P. Caron, B. Domercq, Y.-D. Zhang, S. Barlow, S. Thayumanavan, M. Malagoli, J.-L. Brédas, S. R. Marder, B. Kippelen, Chem. Mater. 2003, 15, 994.
37. M. Era, N. Kakiyama, M. Noto, S. H. Lee, T. Tsutsui, Mol. Cryst. Liq. Cryst. 2001, 371, 191.
38. B. Hartenstein, H. Bässler, S. Heun, P. Borsenberger, M. Van der Auweraer, F. C. De Schryver, Chem. Phys., 1995, 191, 321.
39. S. Heun, H. Bässler, P. Borsenberger, Chem. Phys. 1995, 200, 265.
40. M. B. Robin, P. Day, Adv. Inorg. Chem. Radiochem. 1967, 10, 247.
41. + belong and, therefore, whether our calculated reorganization energies are likely to be correct.
42. + belong and, therefore, whether our calculated reorganization energies are likely to be correct.
43. + belong and, therefore, whether our calculated reorganization energies are likely to be correct.
44. R. A. Marcus, Discuss. Faraday Soc. 1960, 29, 21.
45. S. Barlow, Inorg. Chem. 2001, 40, 7047.
46. S. R. Meech, D. Phillips, J. Photochem. 1983, 23, 193.