New n-type organic semiconductors: Synthesis, single crystal structures, cyclic voltammetry, photophysics, electron transport, and electroluminescence of a series of diphenylanthrazolines

被引:267
作者
Tonzola, CJ
Alam, MM
Kaminsky, W
Jenekhe, SA [1 ]
机构
[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA
[2] Univ Washington, Dept Chem Engn, Seattle, WA 98195 USA
关键词
D O I
10.1021/ja036314e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis, properties, and electroluminescent device applications of a series of five new diphenylanthrazoline molecules la-le are reported. Compounds 1b, 1c, and 1d crystallized in the monoclinic system with the space groups P2(1)/c, C2/c, and P2(1)/c, respectively, revealing highly planar molecules. Diphenylanthrazolines la-le have a formal reduction potential in the range -1.39 to -1.58 V (versus SCE) and estimated electron affinities (LUMO levels) of 2.90-3.10 eV. Compounds la-le emit blue light with fluorescence quantum yields of 58-76% in dilute solution, whereas they emit yellow-green light as thin films. The diphenylanthrazoline molecules as the emissive layers in light-emitting diodes gave yellow light with a maximum brightness of 133 cd/m(2) and an external quantum efficiency of up to 0.07% in ambient air. Bilayer light-emitting diodes using compounds la-le as the electron-transport layer and poly(2-methoxy-5-(2'-ethyl-hexyloxy)-1,4-phenylene vinylene) as the emissive layer had a maximum external efficiency of 3.1% and 2.0 lm/W and a brightness of up to 965 cd/m(2) in ambient air. These results represent enhancements of up to 50 times in external quantum efficiency and 17 times in brightness when using 1a-1e as the electron-transport materials in polymer light-emitting diodes. These results demonstrate that the new diphenylanthrazolines are promising n-type semiconductors for organic electronics.
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页码:13548 / 13558
页数:11
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