Phenylquinoxaline Polymers and Low Molar Mass Glasses as Electron-Transport Materials in Organic Light-Emitting Diodes

We present a new synthetic approach to both phenylquinoxaline polymers and low molar mass glasses. A palladium-catalyzed coupling of arylalkynes and bromobenzenes and subsequent oxidation of the triple bonds lead to the corresponding benziles. Reaction with diaminobenzidine yields poly(phenylquinoxa...

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Bibliographic Details
Published in:Macromolecules 1998-09, Vol.31 (19), p.6434-6443
Main Authors: Jandke, Markus, Strohriegl, Peter, Berleb, Stefan, Werner, Ekkehard, Brütting, Wolfgang
Format: Article
Language:English
Subjects:
Applied sciences
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Polymers with particular properties
Preparation, kinetics, thermodynamics, mechanism and catalysts
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Summary:We present a new synthetic approach to both phenylquinoxaline polymers and low molar mass glasses. A palladium-catalyzed coupling of arylalkynes and bromobenzenes and subsequent oxidation of the triple bonds lead to the corresponding benziles. Reaction with diaminobenzidine yields poly(phenylquinoxalines) (PPQs), whereas the reaction with 1,2-diaminobenzenes leads to low molar mass bis(phenylquinoxalines) (BPQs) and tris(phenylquinoxalines) (TPQs). Both PPQs and TPQs carry tert-butyl or CF3− substituents and are fully soluble in chlorinated hydrocarbons. The starburst TPQs are able to form stable, low molar mass glasses. Cyclic voltammetry reveals that the TPQs have low-lying lowest unoccupied molecular orbitals levels at about −3.6 eV and are attractive as electron-transport materials in organic light-emitting diodes (LEDs). Two-layer LEDs with poly(phenylenevinylene) were fabricated that show a maximum brightness of 450 cd/m2.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma9806054