[en] We present a joint experimental and theoretical study of the structural and charge-transport properties of a liquid-crystalline a,?-disubstituted oligothiophene derivative for application in organic field-effect transistors. The structural properties of the crystalline and smectic phases are investigated by atomic force microscopy, X-ray reflectometry, and X-ray diffraction. To complement these data, molecular mechanics calculations together with the simulation of X-ray diffraction spectra were performed to determine the relative positions of the molecules in the unit cell. The electrical characteristics of field-effect transistors based on the oligothiophene derivative were measured and compared in the crystalline and smectic phases. Although the silanation of the SiO2 gate dielectric promoted a marked improvement in the charge-carrier mobilities in the crystalline phase, the expected suppression of grain boundaries in the liquid-crystalline phase was not unambiguously evidenced. The experimental results we e further complemented by a detailed theoretical analysis of the electronic couplings governing the charge-transport properties on the molecular scale.
Disciplines :
Chemistry Physics
Author, co-author :
Lemaur, Vincent ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
Bouzakraoui, Said
Olivier, Yoann ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
Brocorens, Patrick ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
Burhin, C.
El Beghdadi, J.
Martin-Hoyas, A.
Jonas, A.M.
Serban, D.A.
Vlad, A.
Boucher, N.
Leroy, J.
Sferrazza, Michèle
Melinte, S.
Sergeev, S.
Geerts, Yves
Lazzaroni, Roberto ; Université de Mons > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Cornil, Jérôme ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
Kagan, C. R.; Andry, P. Thin-Film Transistors; Marcel Dekker: New York, 2003.
Katz, H. E.; Lovinger, A. J.; Laquindanum, J. G. Chem. Mater. 1998, 10, 457.
Fichou, D., Ed. Handbook of Oligo- and Polythiophenes; Wiley- VCH: Weinheim, Germany, 1999.
Halik, M.; Klauk, H.; Zschieschang, U.; Schmid, G.; Ponomarnko, S.; Kirchmeyer, S.; Weber, W. Adv. Mater. 2003, 15, 917.
Tanase, C.; Meijer, E. J.; Blom, P. W. M.; de Leeuw, D. M. Phys. Rev. Lett. 2003, 91, 216601.
Verlaak, S.; Heremans, P. Phys. Rev. B 2007, 75, 115127.
Adam, D.; Schumacher, P.; Simmerer, J.; Haussling, L.; Siemensmeyer, K.; Etzbach, K. H.; Haarer, D. Nature 1994, 371, 141.
Bushby, R. J.; Lozman, O. R. Curr. Opin. Colloid Interface Sci. 2002, 7, 343.
Debije, M. G.; Piris, J.; de Haas, M. P.; Warman, J. M.; Tomovic, Z.; Simpson, C. D.; Watson, M. D.; Mullen, K. J. Am. Chem. Soc. 2004, 126, 4645.
Bunk, O.; Nielsen, M. M.; Solling, T. I.; van de Craats, A. M.; Stutzmann, N. J. Am. Chem. Soc. 2003, 125, 2252.
Lemaur, V.; da Silva Filho, D. A.; Coropceanu, V.; Lehmann, M.; Geerts, Y.; Piris, J.; Debije, M. G.; van de Craats, A. M.; Senthilkumar, K.; Siebbeles, L. D. A.; Warman, J. M.; Brédas, J. L.; Cornil, J. J. Am. Chem. Soc. 2004, 126, 3271.
Funahashi, M.; Hanna, J.-I. Adv. Mater. 2005, 17, 594.
Funahashi, M.; Hanna, J.-I. Appl. Phys. Lett. 2000, 76, 2574.
Veres, J.; Ogier, S.; Lloyd, G.; de Leeuw, D. M. Chem. Mater. 2004, 16, 4543.
Gundlach, D. J.; Shelby Kuo, C.-C.; Sheraw, C. D.; Nichols, J. A.; Jackson, T. N. Proc. SPIE 2001, 54, 4466.
Salleo, A.; Chabinyc, M. L.; Yang, M. S.; Street, R. A. Appl. Phys. Lett. 2002, 81, 4383.
Cho, N. S.; Cho, S.; Elbing, M.; Lee, J. K.; Yang, R.; Seo, J. H.; Lee, K.; Bazan, G. C.; Heeger, A. J. Chem. Mater. 2008, 20, 6291.
Leroy, J.; Levin, J.; Sergeyev, S.; Geerts, Y. Chem. Lett. 2006, 35, 166.
Brocorens, P.; Van Vooren, A.; Chabinyc, M. L.; Toney, M. F.;Shkunov, M.; Heeney, M.; McCulloch, I.; Cornil, J.; Lazzaroni, R. Adv. Mater. 2009, 21, 1193.
Van Bolhuis, F.; Wynberg, H.; Havinga, E. E.; Meijer, E. W.; Staring, E. G. Synth. Met. 1989, 30, 381.
Fichou, D. J. Mater. Chem. 2000, 10, 571.
Sun, H. J. Phys. Chem. B 1998, 102, 7338.
MS Modeling, v4.0.0.0. Accelrys Software Inc: San Diego, CA, 2005.
Ewald, P. P. Ann. Phys. 1921, 64, 253.
Cerius2. Accelrys: San Diego, CA, 1997.
Coropceanu, V.; Cornil, J.; da Silva Filho, D. A.; Olivier, Y.; Silbey, R.; Brédas, J. L. Chem. Rev. 2007, 107, 926.
Van Vooren, A.; Kim, J. S.; Cornil, J. ChemPhysChem 2008, 9, 1.
Ridley, J.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111.
Brédas, J. L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971.
Brédas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804.
Newton, M. Chem. Rev. 1991, 91, 767.
Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Hutchinson, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13480.
Collings P. J.; Hird, M. Introduction to Liquid Crystals: Chemistry and Physics; Taylor & Francis: London, 2004.
Dierking, I. Texture of Liquid Crystals; Wiley-VCH: Weinheim, Germany, 2003.
Gray, G. W.; Goodby, J. W. G. Smectic Liquid Crystals; Leonard Hill: Philadelphia, PA, 1984.
Bridou, F.; Pardo, B. J. Phys. III 1994, 4, 1523.
Bollinne, C.; Stone, V. W.; Carlier, V.; Jonas, A. Macromolecules 1999, 32, 4719.
Moret, M.; Campione, M.; Borghesi, A.; Miozzo, L.; Sassella, A.; Trabattoni, S.; Lotz, B.; Thierry, A. J. Mater. Chem. 2005, 15, 2444.
Rhayem, J.; Valenza, M.; Rigaud, D.; Szydlo, N.; Lebrun, H. J. Appl. Phys. 1998, 83, 3660.
Akimichi, H.; Wargai, K.; Hotta, S.; Kano, H.; Sakaki, H. Appl. Phys. Lett. 1991, 58, 1500.
Sirringhaus, H. Adv. Mater. 2005, 17, 2411.
Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99.
Nagamatsu, S.; Kaneto, K.; Azumi, R.; Matsumoto, M.; Yoshida, Y.; Yase, K. J. Phys. Chem. B 2005, 109, 9374.
Muck, T.; Fritz, J.; Wagner, V. Appl. Phys. Lett. 2005, 86, 232101.
Bourguiga, R.; Horowitz, G.; Garnier, F.; Hajlaoui, R.; Jemai, S.; Bouchriha, H. J. Appl. Phys. 2002, 19, 117.
Baldo, M. A.; Deutsch, M.; Burrows, P. E.; Gossenberger, H.; Gerstenberg, M.; Ban, V.; Forrest, S. R. Adv. Mater. 1998, 10, 1505.
Forrest, S. R. Chem. Rev. 1997, 97, 1793.
Wilkinson, F. S., Norwood, R. F., McLellan, J. M., Lawson, L. R., Patrick, D. L.
Serban, D. A.; Kilchytska, V.; Vlad, A.; Martin-Hoyas, A.; Nysten, B.; Jonas, A. M.; Geerts, Y. H.; Lazzaroni, R.; Bayot, V.; Flandre, D.; Melinte, S. Appl. Phys. Lett. 2008, 92, 143503.
Horowitz, G.; Hajlaoui, R.; Fichou, D.; El Kassmi, A. J. Appl. Phys. 1999, 85, 3202.
Muck, T.; Wagner, V.; Baas, U.; Leufgen, M.; Geurts, J.; Molenkamp, L. W. Synth. Met. 2004, 146, 317.
van Breemen, A. J. J. M.; Herwig, P. T.; Chlon, C. H. T.; Sweelssen, J.; Schoo, H. F. M.; Setayesh, S.; Hardeman, W. M.; Martin, C. A.; de Leeuw, D. M.; Valeton, J. J. P.; Bastiaansen, C. W. M.; Broer, D. J.; Popa-Merticaru, A. R.; Meskers, S. C. J. J. Am. Chem. Soc. 2006, 128, 2336.
Murphy, A. R.; Chang, P. C.; VanDyke, P.; Liu, J.; Fréchet, J. M. J.; Subramanian, V.; DeLongchamp, D. M.; Sambasivan, S.; Fischer, D. A.; Lin, E. Chem. Mater. 2005, 17, 6033.
