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New 3pi-2spiro ladder-type phenylene materials: synthesis, physicochemical properties and applications in OLEDs.

New routes to ladder-type phenylene materials 1 and 2 are described. The oligomers 1 and 2, which possess a "3pi-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.