Thermoluminescence and a new organic light-emitting diode (OLED) based on triplet-triplet fluorescence of the trimethylenemethane (TMM) biradical

Journal of the American Chemical Society

Volumn 129, Issue 29, 2007, Pages 9032-9036

  Namai, Hayato ^a   Ikeda, Hiroshi ^b   Hoshi, Yosuke ^c   Kato, Nobuyuki ^a   Morishita, Yoshii ^c   Mizuno, Kazuhiko ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c High Performance Materials Department   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOINDUCED ELECTRON-TRANSFER (PET); RADICAL CATIONS; REACTION SYSTEMS; TRIMETHYLENEMETHANE;

ELECTRIC EXCITATION; ELECTROLUMINESCENCE; ELECTRON TRANSITIONS; FLUORESCENCE; ORGANIC LIGHT EMITTING DIODES (OLED); THERMOLUMINESCENCE;

PARAFFINS;

HYDROCARBON; METHANE; ORGANIC COMPOUND; RADICAL; TRIMETHYLENEMETHANE; UNCLASSIFIED DRUG;

ARTICLE; ELECTRON TRANSPORT; ISOMERIZATION; LIGHT EMITTING DIODE; LUMINESCENCE; THERMOLUMINESCENCE;

FLUORESCENCE; FLUORESCENT DYES; FREE RADICALS; GAMMA RAYS; INDICATORS AND REAGENTS; LUMINESCENCE; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 34547493637     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070946+     Document Type: Article

References (40)

1. Marcus, R. A. Ann. Rev. Phys. Chem. 1964, 15, 155-196.
2. Schuster, G. B. Acc. Chem. Res. 1979, 12, 366-373.
3. Electrogenerated Chemiluminescence; Bard, A. J., Ed.; Marcel Dekker: New York, 2004.
4. (a) Organic Light-emitting Device, A Survey; Shinar, J., Ed.; Springer-Verlag: New York, 2004.
5. (b) Shinar, J.; Savvateev, V. In Organic Light-emitting Device, A Survey; Shinar, J., Ed.; Springer-Verlag: New York, 2004; pp 1-42.
6. Organic Light-emitting Diodes. Principles, Characteristics, and Processes; Kalinowski, J., Ed.; Marcel Dekker: New York, 2005.
7. Organic Light Emitting-Devices: Synthesis, Properties and Applications; Mullen, K., Scherf, U., Eds.; Wiley-VCH: Weinheim, 2006.
8. For a recent report on singlet and triplet emission from OLEDs or polymers, see: (a) Sun, Y.; Giebink, N. C.; Kanno, H.; Ma, B.; Thompson, M. E.; Forrest, S. R. Nature 2006, 440, 908-912.
9. (b) Mak, G S. K.; Evans, N. R.; Watkins, S. E.; Williams, C. K.; Holmes, A. B.; Boothby, C. E.; Koehler, A.; Friend, R. H. Proceedings of SPIE-The International Society for Optical Engineering 2004, 5519 (Organic Light-Emitting Materials and Devices VIII), 24-34.
10. (a) Roth, H. D. J. Phys. Chem. A. 2003, 107, 3432-3437.
11. (b) Roth, H. D. Pure Appl. Chem. 2005, 77, 1075-1085.
12. (c) Roth, H. D. J. Photochem. Photobiol. C. 2001, 2, 93-116.
13. (a) Ikeda, H.; Minegishi, T.; Abe, H.; Konno, A.; Goodman, J. L.; Miyashi, T. J. Am. Chem. Soc. 1998, 120, 87-95.
14. (b) Ikeda, H.; Minegishi, T.; Miyashi, T. J. Chem. Soc., Chem. Commun. 1994, 297-298.
15. (c) Miyashi, T.; Ikeda, H.; Takahashi, Y. Acc. Chem. Res. 1999, 32, 815-824.
16. (a) Ikeda, H.; Akiyama, K.; Takahashi, Y.; Nakamura, T.; Ishizaki, S.; Shiratori, Y.; Ohaku, H.; Goodman, J. L.; Houmam, A.; Wayner, D. D. M.; Tero-Kubota, S.; Miyashi, T. J. Am. Chem. Soc. 2003, 125, 9147-9157.
17. (b) Ikeda, H.; Nakamura, T.; Miyashi, T.; Goodman, J. L.; Akiyama, K.; Tero-Kubota, S.; Houmam, A.; Wayner, D. D. M. J. Am. Chem. Soc. 1998, 120, 5832-5833.
18. (c) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080.
19. (d) Miyashi, T.; Ikeda, H.; Takahashi, Y.; Akiyama, K. In Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI: London, 1999; Vol. 6, p 1-39.
20. Deniau, C.; Dérouléde, A.; Kieffer, F.; Rigaut, J. J. Lumin. 1971, 3, 325-350.
21. Brocklehurst, B.; Russell, R. D. Trans. Faraday. Soc. 1969, 65, 2159-2167.
22. Ikeda, H.; Namai, H.; Kato, N.; Ikeda, T. Tetrahedron Lett. 2006, 47, 1857-1860.
23. Ikeda, H.; Namai, H.; Kato, N.; Ikeda, T. Tetrahedron Lett. 2006, 47, 1501-1504.
24. Turro, N. J.; Mirbach, M. J.; Harrit, N.; Berson, J. A.; Platz, M. S. J. Am. Chem. Soc. 1978, 100, 7653-7658.
25. Ikeda, H.; Namai, H.; Taki, H.; Miyashi, T. J. Org. Chem. 2005, 70, 3806-3813.
26. •• and the corresponding bis(4-methoxyphenyl) derivative. See ref 10a.
27. Karki, S. B.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Zona, T. A. J. Am. Chem. Soc. 1997, 119, 431-432.
28. bull;• is fluorescence based on its lifetime. See ref 15.
29. (a) Bromberg, A.; Meisel, D. J. Phys. Chem. 1985, 89, 2507-2513.
30. (b) Bromberg, A.; Schmidt, K. H.; Meisel, D. J. Am. Chem. Soc. 1985, 107, 83-91.
31. This EL band may be assigned to an exciplex of PVK and 1b. Further studies on this band are now in progress and will be published elsewhere.
32. ox) reported by Wayner for structurally related organic radicals. See refs 23-25 and the Supporting Information.
33. Wayner, D. D. M.; McPhee, D. J.; Griller, D. J. Am. Chem. Soc. 1988, 110, 132-137.
34. Sim, B. A.; Milne, P. H.; Griller, D.; Wayner, D. D. M. J. Am. Chem. Soc. 1990, 112, 6635-6638.
35. Workentin, M. S.; Wayner, D. D. M. Res. Chem. Intermed. 1993, 19, 777-785.
36. •• toward molecular oxygen or some reactant. For reactions of TMM biradicals, see ref 27.
37. (a) Little, R. D. Chem. Rev. 1996, 96, 93-114.
38. (b) Allan, A. K.; Carroll, G. L.; Little, R. D. Eur. J. Org. Chem. 1998, 1-12.
39. Although an OLED with the dimethoxy derivative of 1a showed a similar performance, their luminescence intensity and current efficiency were slightly lower than those of 1b. A similar attempt using 1a gave unfruitful results. Nothing was attempted for 1c. Further studies are now in progress and will be published elsewhere.
40. Cosimbescu, L.; Hatwar, T. K. U.S. Pat. Appl. Publ. (2005), 25 pp.