Solution Processable Fluorenyl Hexa-peri-hexabenzocoronenes in Organic Field-Effect Transistors and Solar Cells

• Published in: Advanced functional materials 2010-03, Vol.20 (6), p.927-938
• Main Authors: Wong, Wallace W. H., Singh, T. Birendra, Vak, Doojin, Pisula, Wojciech, Yan, Chao, Feng, Xinliang, Williams, Evan L., Chan, Khai Leok, Mao, Qinghui, Jones, David J., Ma, Chang-Qi, Müllen, Klaus, Bäuerle, Peter, Holmes, Andrew B.
• Format: Article
• Language: English
• Subjects: Contact; Devices; hexabenzocoronene; Nanostructure; organic field-effect transistors; Organizations; Photovoltaic cells; Polymer blends; self-assembly; Solar cells; Transistors
• ISSN: 1616-301X; 1616-3028; 1616-3028
• DOI: 10.1002/adfm.200901827

The organization of organic semiconductor molecules in the active layer of organic electronic devices has important consequences to overall device performance. This is due to the fact that molecular organization directly affects charge carrier mobility of the material. Organic field‐effect transistor (OFET) performance is driven by high charge carrier mobility while bulk heterojunction (BHJ) solar cells require balanced hole and electron transport. By investigating the properties and device performance of three structural variations of the fluorenyl hexa‐peri‐hexabenzocoronene (FHBC) material, the importance of molecular organization to device performance was highlighted. It is clear from 1H NMR and 2D wide‐angle X‐ray scattering (2D WAXS) experiments that the sterically demanding 9,9‐dioctylfluorene groups are preventing π–π intermolecular contact in the hexakis‐substituted FHBC 4. For bis‐substituted FHBC compounds 5 and 6, π–π intermolecular contact was observed in solution and hexagonal columnar ordering was observed in solid state. Furthermore, in atomic force microscopy (AFM) experiments, nanoscale phase separation was observed in thin films of FHBC and [6,6]‐phenyl‐C61‐butyric acid methyl ester (PC61BM) blends. The differences in molecular and bulk structural features were found to correlate with OFET and BHJ solar cell performance. Poor OFET and BHJ solar cells devices were obtained for FHBC compound 4 while compounds 5 and 6 gave excellent devices. In particular, the field‐effect mobility of FHBC 6, deposited by spin‐casting, reached 2.8 × 10−3 cm2 V−1 s and a power conversion efficiency of 1.5% was recorded for the BHJ solar cell containing FHBC 6 and PC61BM. The performance of organic electronic devices depends heavily on the charge transport property of the organic semiconductor material employed. Fluorenyl hexa‐peri‐hexabenzocoronene (FHBC) materials have the ability to self‐organize into columnar structures which can enhance charge transport. A field‐effect mobility of 2.8 × 10−3 cm2 V−1 s−1 was obtained for the organic field‐effect transistor device and a power conversion efficiency of 1.5% was recorded for the bulk heterojunction solar cell.