Chromophore fluorination enhances crystallization and stability of soluble anthradithiophene semiconductors

被引:291
作者
Subramanian, Sankar [1 ]
Park, Sung Kyu [2 ]
Parkin, Sean R. [1 ]
Podzorov, Vitaly [3 ]
Jackson, Thomas N. [2 ]
Anthony, John E. [1 ]
机构
[1] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA
[2] Penn State Univ, Dept Elect Engn, University Pk, PA 16802 USA
[3] Rutgers State Univ, Dept Phys & Astron, Piscataway, NJ 08854 USA
关键词
D O I
10.1021/ja073235k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report dramatic improvements in the stability and crystallinity arising from partial fluorination of soluble anthradithiophene derivatives. These fluorinated materials still behave as p-type semiconductors but with dramatic increases in thermal and photostability compared to the non-fluorinated derivatives. The triethylsilyl-substituted material forms highly crystalline films even from spincast solutions, leading to devices with maximum hole mobility greater than 1.0 cm(2)N s. In contrast, the triisopropylsilyl derivative forms large, high-quality crystals that could serve as the substrate for transistor fabrication. For this compound, mobility as high as 0.1 cm(2)N S Was measured on the freestanding crystal.
引用
收藏
页码:2706 / +
页数:3
相关论文
共 23 条
[1]  
[Anonymous], 2007, J CHEM PHYS
[2]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[3]   Phenyl-perfluorophenyl stacking interactions: Topochemical[2+2] photodimerization and photopolymerization of olefinic compounds [J].
Coates, GW ;
Dunn, AR ;
Henling, LM ;
Ziller, JW ;
Lobkovsky, EB ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3641-3649
[4]   Highly soluble [1]benzothieno[3,2-b]benzothiophene (BTBT) derivatives for high-performance, solution-processed organic field-effect transistors [J].
Ebata, Hideaki ;
Izawa, Takafumi ;
Miyazaki, Eigo ;
Takimiya, Kazuo ;
Ikeda, Masaaki ;
Kuwabara, Hirokazu ;
Yui, Tatsuto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :15732-+
[5]   n-type building blocks for organic electronics: A homologous family of fluorocarbon-substituted thiophene oligomers with high carrier mobility [J].
Facchetti, A ;
Mushrush, M ;
Katz, HE ;
Marks, TJ .
ADVANCED MATERIALS, 2003, 15 (01) :33-+
[6]   Activation of hydrogen- and halogen-bonding interactions in tetrathiafulvalene-based crystalline molecular conductors [J].
Fourmigué, M ;
Batail, P .
CHEMICAL REVIEWS, 2004, 104 (11) :5379-5418
[7]   Pentacene TFT with improved linear region characteristics using chemically modified source and drain electrodes [J].
Gundlach, DJ ;
Jia, LL ;
Jackson, TN .
IEEE ELECTRON DEVICE LETTERS, 2001, 22 (12) :571-573
[8]  
GUNDLACH DJ, IN PRESS NAT MAT
[9]   High-mobility polymer gate dielectric pentacene thin film transistors [J].
Klauk, H ;
Halik, M ;
Zschieschang, U ;
Schmid, G ;
Radlik, W ;
Weber, W .
JOURNAL OF APPLIED PHYSICS, 2002, 92 (09) :5259-5263
[10]   Characterization of the molecular parameters determining charge transport in anthradithiophene [J].
Kwon, O ;
Coropceanu, V ;
Gruhn, NE ;
Durivage, JC ;
Laquindanum, JG ;
Katz, HE ;
Cornil, J ;
Brédas, JL .
JOURNAL OF CHEMICAL PHYSICS, 2004, 120 (17) :8186-8194