Green and Yellow Electroluminescent Dipolar Carbazole Derivatives:  Features and Benefits of Electron-Withdrawing Segments

New multiply substituted carbazole derivatives containing fluorene or phenylene conjugated oxadiazole segments and quinoxaline units were obtained by palladium-catalyzed C−N coupling reactions. They are amorphous with the glass transition temperature (T g) in the range 104−176 °C. The emission color...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of materials 2002-09, Vol.14 (9), p.3852-3859
Main Authors: Thomas, K. R. Justin, Lin, Jiann T, Tao, Yu-Tai, Chuen, Chang-Hao
Format: Article
Language:English
Subjects:
Applied sciences
Electronics
Exact sciences and technology
Optoelectronic devices
Semiconductor electronics. Microelectronics. Optoelectronics. Solid state devices
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:New multiply substituted carbazole derivatives containing fluorene or phenylene conjugated oxadiazole segments and quinoxaline units were obtained by palladium-catalyzed C−N coupling reactions. They are amorphous with the glass transition temperature (T g) in the range 104−176 °C. The emission color of the materials varies from blue to yellow and is dependent on the nature of the electron-withdrawing segments and solvents. Two reversible one-electron oxidations were observed for these molecules in cyclic voltammograms, which originate from the peripheral 3,6-diarylamino units in the 3,6,9-trisubstituted derivatives and diarylamine and carbazole segments in the 3,9-disubstituted compounds. Reductions originating from quinoxaline segments were also located for the molecules incorporating quinoxaline moieties. The double-layer organic light-emitting diodes fabricated using these compounds as hole-transporting/emitting layers and TPBI or Alq3 as an electron-transporting layer emit bluish green to yellow colors. The recombination zone is restricted in the HTL layer for the quinoxaline-containing molecules irrespective of the electron-transporting layer used and emission occurs from them. However, for the oxadiazole derivatives emission in the Alq3-based devices is either red-shifted or resembles that of Alq3. Cyclic voltammetric and spectroscopic data support more pronounced electron affinity for the quinoxaline-incorporated carbazole derivatives than for the oxadiazole-tethered carbazole materials.
ISSN:0897-4756
1520-5002
DOI:10.1021/cm0202512