Title: Dibenzothiophene/oxide and quinoxaline/pyrazine derivatives serving as electron-transport materials
Authors: Huang, Tai-Hsiang
Whang, Wha-Tzong
Shen, Jiun Yi
Wen, Yuh-Sheng
Lin, Jiann T.
Ke, Tung-Huei
Chen, Li-Yin
Wu, Chung-Chih
Department of Materials Science and Engineering
Issue Date: 21-Jul-2006
Abstract: A series of 2,8-disubstituted dibenzothiophene and 2,8-disubstituted dibenzothiophene-SS-dioxide derivatives containing quinoxaline and pyrazine moieties are synthesized via three key steps: i) palladium-catalyzed Sonogashira coupling reaction to form dialkynes; ii) conversion of the dialkynes to diones; and iii) condensation of the diones with diamines. Single-crystal characterization of 2,8-di(6,7-dimethyl-3-phenyl-2-quinoxalinyl)-5H-5 lambda(6)-dibenzo[b,d]thiophene-5,5-dione indicates a triclinic crystal structure with space group P1 and a non-coplanar structure. These new materials are amorphous, with glass-transition temperatures ranging from 132 to 194 degrees C. The compounds (Cpd) exhibit high electron mobilities and serve as effective electron-transport materials for organic light-emitting devices. Double-layer devices are fabricated with the structure indium tin oxide (ITO)/Qn/Cpd/LiF/Al, where yellow-emitting 2,3-bis[4-(N-phenyl-9-ethyl-3-carbazolylamino)phenyl]quinoxaline (Qn) serves as the emitting layer. An external quantum efficiency of 1.41 %, a power efficiency of 4.94 lm W-1, and a current efficiency of 1.62 cd A(-1) are achieved at a current density of 100 mA cm(-2).
URI: http://dx.doi.org/10.1002/adfm.200500823
ISSN: 1616-301X
DOI: 10.1002/adfm.200500823
Volume: 16
Issue: 11
Begin Page: 1449
End Page: 1456
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