Verfahren zur Schwermetall-freien Herstellung von N,N'-persubstituierten 5,5'-Diamino-2,2'bithiophenen und 2,2'-Diamino-5,5'-bithiazolen sowie deren Verwendung

Research output: Intellectual Property › Patent application/Patent

Contributors

  • TUD Dresden University of Technology

Abstract

Method for preparing 5,5'-diamino-2,2'-bisthiophene or -bisthiazole derivatives (X), or their salt-like oxidation products. Method for preparing 5,5'-diamino-2,2'-bisthiophene or -bisthiazole derivatives (X), of formulae (1) or (2), or their salt-like oxidation products comprises conventional preparation of the corresponding 2-unsubstituted heterocycle then reacting this with an oxidizing agent free of heavy metals, in a solvent at 0-100[deg]C, preferably room temperature. [Image] R1> and R2>alkyl (e.g. Me, Et or substituted propyl), aryl (e.g. phenyl, naphthyl, anthryl, phenanthryl or pyrenyl), or, optionally substituted once, a heteroaromatic group (e.g. (benzo)thienyl, (benzo)thiazolyl, pyridyl, quinolyl or quinazolinyl), or together with the N atom form a heterocyclic fragment, e.g. phenothiazinyl, phenoxazinyl or phenodiazinyl; and R3> and R4>hydrogen, alkyl or aryl (e.g. as above) or a heteroaromatic group (e.g. as above), all optionally substituted once.

Translated title of the contribution
Preparation of diamino-2,2'-bis-thiophene or -thiazole compounds, useful in organic light-emitting diodes or field-effect transistors, by coupling the 2-unsubstituted heterocycle with oxidizing agent

Details

Method for preparing 5,5'-diamino-2,2'-bisthiophene or -bisthiazole derivatives (X), or their salt-like oxidation products. Method for preparing 5,5'-diamino-2,2'-bisthiophene or -bisthiazole derivatives (X), of formulae (1) or (2), or their salt-like oxidation products comprises conventional preparation of the corresponding 2-unsubstituted heterocycle then reacting this with an oxidizing agent free of heavy metals, in a solvent at 0-100[deg]C, preferably room temperature. [Image] R1> and R2>alkyl (e.g. Me, Et or substituted propyl), aryl (e.g. phenyl, naphthyl, anthryl, phenanthryl or pyrenyl), or, optionally substituted once, a heteroaromatic group (e.g. (benzo)thienyl, (benzo)thiazolyl, pyridyl, quinolyl or quinazolinyl), or together with the N atom form a heterocyclic fragment, e.g. phenothiazinyl, phenoxazinyl or phenodiazinyl; and R3> and R4>hydrogen, alkyl or aryl (e.g. as above) or a heteroaromatic group (e.g. as above), all optionally substituted once.

Original languageGerman
IPC (International Patent Classification)H01L 51/ 50 A N
Patent numberDE10343757
Country/TerritoryGermany
Priority date15 Sept 2003
Priority numberDE20031043757
Publication statusPublished - 21 Apr 2005
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