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

Starting from N,N-diarylsubstituted thioureas 20 and thioacetamides 21 a series of heterocyclic analogous of N,N-per-arylated 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 st...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 9; pp. 1268 - 1276
Main Authors Schumann, J, Kanitz, A, Hartmann, H
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
hole transport materials
heterocyclization
N-perarylated 2-aminothiazoles
N-perarylated 2-aminothiophenes
DERIVATIVES
TRIARYLAMINES
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Summary:Starting from N,N-diarylsubstituted thioureas 20 and thioacetamides 21 a series of heterocyclic analogous of N,N-per-arylated 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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2002-32531