Chem. Mater., 20 (2), 540–552, 2008. 10.1021/cm702217u
Web Release Date: December 22, 2007

Copyright © 2008 American Chemical Society

Electrochemical Deposition of Bis(N,N′-diphenylaminoaryl) Substituted Ferrocenes, and Their Application as a Hole-Injection Layer on Polymeric Light-Emitting Diodes

Chao Cheng Chiang,† Hong-Chun Chen,† Chin-sheng Lee,† Man-kit Leung,*†‡ Kun-Rung Lin,‡ and Kuo-Huang Hsieh‡

Department of Chemistry and Institute of Polymer Science and Engineering, National Taiwan University, 1 Roosevelt Road, Section 4, Taipei 106, Taiwan, ROC

Received August 7, 2007

Revised Manuscript Received October 30, 2007

Abstract:

The synthesis, spectro-electrochemical study, and electrochemical polymerization of bis(diphenylamino) substituted ferrocenes (Fcs), including the family of the 1,3,4-oxadiazole (OXD) bridged 1,1′-[p-(Ph2N)(C6H4)nOXD]2Fc and the vinylene bridged ferrocene 1,1′-[p-(Ph2N)(C6H4)-(E)-CHCH]2Fc, have been carried out. The ferrocene compounds underwent three stepwise one-electron oxidations to form the (3+) radical cations that further electrochemically polymerized on a Pt or an indium tin oxide (ITO) electrode surface. The polymeric layers showed extremely good hole-injection properties. The polymeric light emitting devices (PLEDs) of ITO/ED-1,1′-[Ph2N(C6H4)3OXD]2Fc/PVK:Ir(PPy)3:PBD/Mg-Ag showed a turn-on voltage (at 100 cd/m2) of 11 V, with a maximum brightness of 27 700 cd/m2. The turn-on voltage was 1.5 V lower than that of the poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate) based PLED and 2 V lower than the corresponding electrochemically deposited poly(4-(N,N-diphenylamino)styrene) based PLED.

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