Carbazole Compounds as Host Materials for Triplet Emitters in Organic Light-Emitting Diodes:  Tuning the HOMO Level without Influencing the Triplet Energy in Small Molecules

• Published in: Journal of the American Chemical Society 2004-05, Vol.126 (19), p.6035-6042
• Main Authors: Brunner, Klemens, van Dijken, Addy, Börner, Herbert, Bastiaansen, Jolanda J. A. M, Kiggen, Nicole M. M, Langeveld, Bea M. W
• Format: Article
• Language: English
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja049883a

A series of novel carbazole compounds was synthesized and tested for their suitability as host for triplet emitters in an organic-light emitting diode (OLED). In these compounds, a carbazole unit is either connected to other carbazole units to form carbazole dimers and trimers or to fluorene and oxadiazole derivatives to form mixed compounds. The HOMO level of carbazole compounds can be tuned by substitution at the 3, 6, and/or 9 positions. Making oligomers by connecting carbazole molecules via their 3 (3‘) positions shifts the HOMO level to higher energy, while replacing alkyl groups at the 9 (9‘) positions by aryl groups shifts the HOMO level to lower energy. Furthermore, it has been found that the triplet energy of these compounds is determined by the presence of poly(p-phenyl) chains in the molecular structure. By identifying the longest poly(p-phenyl) chain, one can predict whether a compound will be a suitable host for a high-energy triplet emitter. An overview of HOMO levels, singlet and triplet levels, and exchange energies is given for all carbazole compounds synthesized. Finally, OLEDs employing two selected carbazole compounds as host and fac-tris(2-phenylpyridine)-iridium (Ir(ppy)3) as guest were constructed and characterized electrically.