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Dibenzothiophene/Oxide and Quinoxaline/Pyrazine Derivatives Serving as Electron‐Transport Materials
Author(s) -
Huang T.H.,
Whang W.T.,
Shen J. Y.,
Wen Y.S.,
Lin J. T.,
Ke T.H.,
Chen L.Y.,
Wu C.C.
Publication year - 2006
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.200500823
Subject(s) - pyrazine , quinoxaline , materials science , dibenzothiophene , sonogashira coupling , single crystal , thiophene , crystallography , organic chemistry , palladium , catalysis , chemistry , sulfur , metallurgy
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 H ‐5λ 6 ‐dibenzo[ b , d ]thiophene‐5,5‐dione indicates a triclinic crystal structure with space group P 1 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 .