9,10-Ter-anthrylene-ethynylene: a new molecular architecture for solution processed anthracene-based thin film transistors

Antonio Dell'Aquila; Francesco Marinelli; Junie Tey; Peisi Keg; Yeng-Ming Lam; Oleksiy L. Kapitanchuk; Piero Mastrorilli; Cosimo F. Nobile; Pinalysa Cosma; Alexandr Marchenko; Denis Fichou; Subodh G. Mhaisalkar; Gian Paolo Suranna; Luisa Torsi

doi:10.1039/B714865H

9,10-Ter-anthrylene-ethynylene: a new molecular architecture for solution processed anthracene-based thin film transistors

Antonio Dell'Aquila,^a Francesco Marinelli,^b Junie Tey,^c Peisi Keg,^c Yeng-Ming Lam,^c Oleksiy L. Kapitanchuk,†^c Piero Mastrorilli,^a Cosimo F. Nobile,^a Pinalysa Cosma,^b Alexandr Marchenko,^d Denis Fichou,^d Subodh G. Mhaisalkar,^c Gian Paolo Suranna*^a and Luisa Torsi*^b

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^a Department of Water Engineering and of Chemistry, Polytechnic of Bari, Campus Universitario, via Orabona 4- Bari, Italy
E-mail: surannag@poliba.it
Fax: +39 080 5963611
Tel: +39 080 5963603

^b Department of Chemistry, University of Bari, Campus Universitario, via Orabona 4- Bari, Italy

^c School of Materials Science and Engineering, Nanyang Technological University, Singapore

^d CEA-Saclay, Organic Nanostructures and Semiconductors Lab CNRS-CEA-UPMC, Bât. 461, SPCSI, Gif-sur-Yvette, France

Abstract

This study deals with the properties of a new molecular architecture for organic thin film transistors obtained by introducing 10-decylanthr-9-yl-ethynyl moieties at the anthracene 9,10 positions. The resulting structure, formally a ter-anthrylene-ethynylene (D3ANT), is stable and endowed with sufficient solubility to guarantee the formation of good quality films. The molecule was characterised by ¹H NMR, mass spectrometry, IR, UV–vis and photoluminescence both in solution and in the solid state. Cyclic voltammetry measurements, combined with solution UV–vis, permitted the evaluation of HOMO and LUMO energy levels. A series of D3ANT-based OTFT devices were built both in bottom and top contact configurations by a spin coating technique. Top contact OTFT devices exhibited the best semiconducting characteristics, showing an average mobility of 1.2 × 10⁻² cm² V⁻¹ s⁻¹ with on–off ratios higher then 10⁴, while the highest mobility obtained was 0.055 cm² V⁻¹ s⁻¹. AFM thin-film characterization showed evidence of a granular structure. High-resolution STM images of D3ANT monolayers adsorbed on Au(111) and HOPG reveal highly-ordered self-organized domains with molecules lying flat on the substrates, but, remarkably, no reflections were recorded by out-of plane GIXRD of spin coated films on SiO₂.

Journal of Materials Chemistry

9,10-Ter-anthrylene-ethynylene: a new molecular architecture for solution processed anthracene-based thin film transistors

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