Dibenzothiophene/oxide and quinoxaline/pyrazine derivatives serving as electron-transport materials

Tai Hsiang Huang*, Wha Tzong Whang, Jiun Yi Shen, Yuh Sheng Wen, Jiann T. Lin, Tung Huei Ke, Li Yin Chen, Chung Chih Wu

*Corresponding author for this work

Research output: Contribution to journalArticle

61 Scopus citations

Abstract

A series of 2,8-disubstituted dibenzothiophene and 2,8-disubstituted dibenzothiophene-S,S-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)-5//-5A6- 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°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.

Original languageEnglish
Pages (from-to)1449-1456
Number of pages8
JournalAdvanced Functional Materials
Volume16
Issue number11
DOIs
StatePublished - 21 Jul 2006

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