Synthesis and characterization of mixed oligoheterocycles based on end-capped oligothiophenes suited for LED applications

Peter Baeuerle; Ullrich Mitschke; E. Mena-Osteritz; M. Sokolowski; David C. Mueller; Markus S. Gross; Klaus Meerholz

doi:10.1117/12.332636

16 December 1998 Synthesis and characterization of mixed oligoheterocycles based on end-capped oligothiophenes suited for LED applications

Peter Baeuerle, Ullrich Mitschke, E. Mena-Osteritz, M. Sokolowski, David C. Mueller, Markus S. Gross, Klaus Meerholz

Author Affiliations +

Proceedings Volume 3476, Organic Light-Emitting Materials and Devices II; (1998) https://doi.org/10.1117/12.332636
Event: SPIE's International Symposium on Optical Science, Engineering, and Instrumentation, 1998, San Diego, CA, United States

Abstract

Homologous series of mixed oligoheterocycles based on end- capped oligothiophenes ECnT 1 were synthesized by introduction of electronegative heteroatoms like oxygen and nitrogen into the conjugated (pi) -system. This led to novel structures 2-11 in which thiophene units of the parent compounds are substituted by other heterocycles with more pronounced acceptor character. Other moieties like phenylsubstituted thiophenes, benzo(c)thiophene, and spiro- bithiophenes have also been implemented resulting in oligothiophenes 12-16. The characterization of the optical and electrochemical properties clearly reveals the influence of the heteroatoms on the electronic properties. Thus e.g., due to the electron withdrawing character of the central heterocycle oxidation of the oligomer is rendered more difficult while reduction is facilitated. In some cases, a hypsochromic shift of the longest wavelength absorption and emission is observed and additionally a significant enhancement of the fluorescence quantum yield in solution and in the solid state. The HOMO/LUMO energy differences determined from the optical measurement correspond qualitatively well with the values obtained from electrochemical data. First experiments on single layer organic light emitting diodes show that these mixed oliogoheterocycles can be used as emitting materials.

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Peter Baeuerle, Ullrich Mitschke, E. Mena-Osteritz, M. Sokolowski, David C. Mueller, Markus S. Gross, and Klaus Meerholz "Synthesis and characterization of mixed oligoheterocycles based on end-capped oligothiophenes suited for LED applications", Proc. SPIE 3476, Organic Light-Emitting Materials and Devices II, (16 December 1998); https://doi.org/10.1117/12.332636

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