Dithiazole-fused naphthalene diimides toward new n-type semiconductors

被引:48
作者
Chen, Xin [1 ]
Guo, Yunlong [1 ]
Tan, Luxi [1 ]
Yang, Ge [1 ]
Li, Yonghai [1 ]
Zhang, Guanxin [1 ]
Liu, Zitong [1 ]
Xu, Wei [1 ]
Zhang, Deqing [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Organ Solids Lab, Beijing 100190, Peoples R China
关键词
FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; SINGLE-CRYSTALLINE TRANSISTORS; HIGH-PERFORMANCE; ORGANIC SEMICONDUCTOR; ANISOTROPIC TRANSPORT; CORE; ELECTRON; DESIGN; DERIVATIVES;
D O I
10.1039/c2tc00308b
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
A simple synthetic approach to dithiazole-fused naphthalene diimides 1 and 2 from 2,6-dibromoNDI (2BrNDI) was described. Note that the synthesis did not involve any metallic catalysts. Based on their cyclic voltammograms, the LUMO energies of 1 and 2 were estimated to be -3.99 eV and -3.98 eV, respectively, being lower than that of unsubstituted NDI. Thin films of 1 and 2 show n-type semiconducting behaviors. OFETs of 1 exhibit electron mobility up to 0.15 cm(2) V-1 s(-1) with high on/off ratio (under ambient conditions) after annealing.
引用
收藏
页码:1087 / 1092
页数:6
相关论文
共 50 条
[1]   n-Type Organic Semiconductors in Organic Electronics [J].
Anthony, John E. ;
Facchetti, Antonio ;
Heeney, Martin ;
Marder, Seth R. ;
Zhan, Xiaowei .
ADVANCED MATERIALS, 2010, 22 (34) :3876-3892
[2]   Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications [J].
Beaujuge, Pierre M. ;
Frechet, Jean M. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) :20009-20029
[3]   Current Trends in Shrinking the Channel Length of Organic Transistors Down to the Nanoscale [J].
Cao, Yang ;
Steigerwald, Michael L. ;
Nuckolls, Colin ;
Guo, Xuefeng .
ADVANCED MATERIALS, 2010, 22 (01) :20-32
[4]   High-Performance Photoresponsive Organic Nanotransistors with Single-Layer Graphenes as Two-Dimensional Electrodes [J].
Cao, Yang ;
Liu, Song ;
Shen, Qian ;
Yan, Kai ;
Li, Pingjian ;
Xu, Jun ;
Yu, Dapeng ;
Steigerwald, Michael L. ;
Nuckolls, Colin ;
Liu, Zhongfan ;
Guo, Xuefeng .
ADVANCED FUNCTIONAL MATERIALS, 2009, 19 (17) :2743-2748
[5]   Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transistors [J].
Chen, Zhihua ;
Zheng, Yan ;
Yan, He ;
Facchetti, Antonio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) :8-+
[6]   General observation of n-type field-effect behaviour in organic semiconductors [J].
Chua, LL ;
Zaumseil, J ;
Chang, JF ;
Ou, ECW ;
Ho, PKH ;
Sirringhaus, H ;
Friend, RH .
NATURE, 2005, 434 (7030) :194-199
[7]   Incorporation of fused tetrathiafulvalene units in a DPP-terthiophene copolymer for air stable solution processable organic field effect transistors [J].
Cortizo-Lacalle, Diego ;
Arumugam, Sasikumar ;
Elmasly, Saadeldin E. T. ;
Kanibolotsky, Alexander L. ;
Findlay, Neil J. ;
Inigo, Anto Regis ;
Skabara, Peter J. .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (22) :11310-11315
[8]   Dithieno-naphthalimide based copolymers for air-stable field effect transistors: synthesis, characterization and device performance [J].
Dai, Gaole ;
Chang, Jingjing ;
Wu, Jishan ;
Chi, Chunyan .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (39) :21201-21209
[9]   Systematic Investigation of Benzodithiophene- and Diketopyrrolopyrrole-Based Low-Bandgap Polymers Designed for Single Junction and Tandem Polymer Solar Cells [J].
Dou, Letian ;
Gao, Jing ;
Richard, Eric ;
You, Jingbi ;
Chen, Chun-Chao ;
Cha, Kitty C. ;
He, Youjun ;
Li, Gang ;
Yang, Yang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) :10071-10079
[10]  
Feng XL, 2009, NAT MATER, V8, P421, DOI [10.1038/NMAT2427, 10.1038/nmat2427]