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New 3π‐2Spiro Ladder‐Type Phenylene Materials: Synthesis, Physicochemical Properties and Applications in OLEDs
Author(s) -
Cocherel Nicolas,
Poriel Cyril,
RaultBerthelot Joëlle,
Barrière Frédéric,
Audebrand Nathalie,
Slawin Alexandra M. Z.,
Vignau Laurence
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801428
Subject(s) - oled , fluorenone , materials science , phenylene , electrochemistry , diode , optoelectronics , chemistry , nanotechnology , polymer , fluorene , layer (electronics) , composite material , electrode
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.