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New 3π‐2Spiro Ladder‐Type Phenylene Materials: Synthesis,Physicochemical Properties and Applications in OLEDs
Authors:Nicolas Cocherel  Cyril Poriel Dr  Joëlle Rault‐Berthelot Dr  Frédéric Barrière Dr  Nathalie Audebrand Dr  Alexandra?M?Z Slawin Prof?Dr  Laurence Vignau Dr
Institution:1. Université de Rennes 1, UMR CNRS 6226 “Sciences Chimiques de Rennes”, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France), Fax: (+33)?223‐236732;2. School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST (UK);3. Université de Bordeaux, IMS/UMR CNRS 5218‐site, ENSCPB, 16 Avenue Pey‐Berland, 33607 Pessac Cedex (France)
Abstract:New routes to ladder‐type phenylene materials 1 and 2 are described. The oligomers 1 and 2 , which possess a “3π‐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‐emitting 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.
Keywords:ladder pentaphenylenes  luminescence  organic light‐emitting diodes  semiconductors  spiro compounds
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