New 3 pi-2Spiro Ladder-Type Phenylene Materials: Synthesis, Physicochemical Properties and Applications in OLEDs

Nicolas Cocherel, Cyril Poriel, Joelle Rault-Berthelot, Frederic Barriere, Nathalie Audebrand, Alexandra M. Z. Slawin, Laurence Vignau

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)

Abstract

New routes to ladder-type phenylene materials I and 2 are described. The oligomers I and 2, which possess a "3 pi-2spiro" architecture, have been synthesized by using extended diketone derivatives 3 and 10 as key intermediates. The physicochemical properties of the new blue-light emitter 2 were studied in detail and compared with those of the less-extended 1. Owing to the recent development Of fluorenone derivatives and their corresponding more conjugated analogues as potential electron-transport materials in organic light-emilting diodes (OLEDs) and as n-type materials for photovoltaic applications, we also report herein the thermal, optical and electrochemical behavior of the key intermediates, diketones 3 and 10. Finally, the application of dispiro 2 as a new light-emitting material in OLEDs is reported.

Original languageEnglish
Pages (from-to)11328-11342
Number of pages15
JournalChemistry - A European Journal
Volume14
Issue number36
DOIs
Publication statusPublished - 2008

Keywords

  • ladder pentaphenylenes
  • luminescence
  • organic light-emitting diodes
  • semiconductors
  • spiro compounds
  • LIGHT-EMITTING-DIODES
  • SPIRO-TYPE MOLECULES
  • OPTICAL-PROPERTIES
  • BUILDING-BLOCKS
  • PHOTOPHYSICAL PROPERTIES
  • CONJUGATED OLIGOMERS
  • COMMON INTERMEDIATE
  • TRANSPORT MATERIALS
  • BLUE EMISSION
  • POLYMERS

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