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http://dx.doi.org/10.5012/bkcs.2005.26.10.1569

Synthesis of 5,6-Dihydro[1,10]phenanthroline Derivatives and Their Properties as Hole-Blocking Layer Materials for Phosphorescent Organic Light-Emitting Diodes  

Lee, Hyo-Won (Department of Chemistry, Chungbuk National University)
An, Jung-Gi (Department of Chemistry, Chungbuk National University)
Yoon, Hee-Kyoon (Department of Chemistry, Chungbuk National University)
Jang, Hyo-Sook (Department of Chemistry, School of Molecular Science-BK21 and Center for Molecular Design and Synthesis, KAIST)
Kim, Nam-Gwang (Department of Chemistry, School of Molecular Science-BK21 and Center for Molecular Design and Synthesis, KAIST)
Do, Young-Kyu (Department of Chemistry, School of Molecular Science-BK21 and Center for Molecular Design and Synthesis, KAIST)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.10, 2005 , pp. 1569-1574 More about this Journal
Abstract
To develop new hole-blocking materials for phosphorescent organic light-emitting diodes (PhOLEDs), 5,6-dihydro-2,9-diisopropyl-4,7-diphenyl[1,10]phenanthroline (1) and 5,6-dihydro-2,9-diisopropyl-4-(4-methoxyphenyl)-7-phenyl[1,10]phenanthroline (2) were synthesized. While the absorption spectrum of 1 is very similar to that of 2, the photoluminescence spectrum of 1 has the feature of the narrower and blue-shifted blueviolet emission at the peak of 356 nm compared to that of 2. The HOMO and LUMO energy levels of 1 and 2 were estimated from the measurement of cyclic voltammetry, and 1 has the appropriate levels for a holeblocking layer (HBL). The use of 1 as a HBL in a green PhOLED led to good efficiency of 23.6 cd/A at 4.4 mA/$cm^2$.
Keywords
BCP derivatives; 5,6-Dihydro-2,9-diisopropyl-4,7-diaryl[1,10]phenanthroline; Hole-blocking materials; Phosphorescent organic light-emitting diode;
Citations & Related Records
Times Cited By KSCI : 4  (Citation Analysis)
Times Cited By Web Of Science : 6  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
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1 Sibley, S.; Thompson, M. E.; Burrows, P. E.; Forrest, S. R. In Optoelectronic Properties of Inorganic Compounds; Roundhill, D. M.; Fackler, J. P. Jr., Eds.; Plenum Press: New York, 1999; pp 29-54
2 You, B.; Kim, H. J.; Park, N. G.; Kim. Y. S. Bull. Korean Chem. Soc. 2001, 22, 1005
3 Kim, J. H.; Lee, H. Bull. Korean Chem. Soc. 2004, 25, 652   DOI   ScienceOn
4 Cheon, J.-W.; Lee, C.-W.; Geum, N.; Gong, M.-S. Bull. Korean Chem. Soc. 2004, 25, 1202   DOI   ScienceOn
5 Kang, J.-G.; Kim, T.-J.; Park, C.; Woo, L. S.; Kim, J. T. Bull. Korean Chem. Soc. 2004, 25, 704   DOI   ScienceOn
6 Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395, 151   DOI   ScienceOn
7 Baldo, M. A.; O'Brien, D. F.; Thompson, M. E.; Forrest, S. R. Phys. Rev. B 1999, 60, 14422   DOI
8 Adachi, C.; Kwong, R. C.; Djurovich, P.; Adamovich, V.; Baldo, M. A.; Thompson, M. E.; Forrest, S. R. Appl. Phys. Lett. 2001, 79, 2082   DOI   ScienceOn
9 Thummel, R. P.; Lefolulon, F.; Cantu, D.; Mahadevan, R. J. Org. Chem. 1984, 49, 2208   DOI
10 Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991   DOI
11 Joshi, H. S.; Jamshidi, R.; Tor, Y. Angew. Chem. Int. Ed. 1999, 38, 2722
12 Ko, S. W.; Jung, B.-J.; Cho, N. S.; Shim, H.-K. Bull. Korean Chem. Soc. 2002, 23, 1235   DOI   ScienceOn
13 Chen, Z.-K.; Huang, W.; Wang, L.-H.; Kang, E.-T.; Chen, B. J.; Lee, C. S.; Lee, S. T. Macromolecules 2000, 33, 9015   DOI   ScienceOn
14 de Leeuw, D. M.; Simenon, M. M. J.; Brown, A. R.; Einerhand, R. E. F. Synth. Met. 1997, 87, 53   DOI   ScienceOn
15 Kinoshita, M.; Kita, H.; Shirota, Y. Adv. Func. Mater. 2002, 12, 780   DOI   ScienceOn
16 Adamovich, V. I.; Cordero, S. R.; Djurovich, P. I.; Tamayo, A.; Thompson, M. E.; D'Andrade, B. W.; Forrest, S. R. Org. Elec. 2003, 4, 77   DOI   ScienceOn
17 Ika, M.; Tokito, S.; Sakamoto, Y.; Suzuki, T.; Taga, Y. Appl. Phys. Lett. 2001, 79, 156   DOI   ScienceOn
18 Wang, Y.; Herron, N.; Grushin, V. V.; LeCloux, D.; Petrov, V. Appl. Phys. Lett. 2001, 79, 449   DOI   ScienceOn
19 Okumoto, K.; Shirota, Y. Chem. Mater. 2003, 15, 699   DOI   ScienceOn
20 Bredas, J. L.; Sibley, R.; Boudreaux, D. S.; Chance, R. R. J. Am. Chem. Soc. 1983, 105, 6555   DOI   ScienceOn
21 Baldo, M. A.; Lamansky, S.; Burrows, P. E.; Thompson, M. E.; Forrest, S. R. Appl. Phys. Lett. 1999, 75, 4   DOI   ScienceOn
22 Ono, K.; Yanase, T.; Ohkita, M.; Saito, K.; Matsushita, Y.; Naka, S.; Okada, H.; Onnagawa, H. Chem. Lett. 2004, 33, 276   DOI   ScienceOn
23 Mitschke, U.; Bauerle, P. J. Mater. Chem. 2000, 10, 1471   DOI   ScienceOn