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Synthesis 2002(9): 1268-1276
DOI: 10.1055/s-2002-32531
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Characterization of Some Heterocyclic Analogues of
N,N′-Perarylated Phenylene-1,4-diamines and Benzidines as a New Class of Hole Transport Materials

Joerg Schumann*a, Andreas Kanitz*a, Horst Hartmannb
a SIEMENS AG Erlangen, Paul-Gossen-Str., 91050 Erlangen, Germany
b University of Applied Sciences, Geusaer Str., 06217 Merseburg, Germany
Fax: +49(3461)462192; e-Mail: Horst.Hartmann@cui.fh-merseburg.de;
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Publication History

Received 5 March 2002
Publication Date:
28 June 2002 (online)

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Abstract

Starting from N,N-diarylsubstituted thioureas 20 and thioacetamides 21 a series of heterocyclic analogous of N,N′-perarylated phenylene-1,4-diamines and benzidines was obtained. These compounds represent, as studied by DSC measurements, a new class of hole transporting materials with high thermal stability and high tendency to form stable amorphous states. Moreover, some of the new compounds are, as measured by cyclic voltammetry, easily reversibly oxidized indicating the formation of persistent radical ions. Such compounds, which are, in general, completely substituted by aryl groups at their heterocyclic moieties, have been successfully used as hole-transport materials in OLEDs.

Key words

heterocyclization - hole transport materials - N-perarylated 2-aminothiophenes - N-perarylated 2-aminothiazoles

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Kanitz, A.; Schumann, J.; Scheffel, M.; Rajoelson, S.; Rogler, W.; Hartmann, H.; Rohde, D. Chem. Lett. 2002, in press.