Core-Fluorinated Naphthalene Diimides: Synthesis, Characterization, and Application in n-Type Organic Field-Effect Transistors

被引:55
作者
yuan, Zhongyi [1 ]
Ma, Yingjie [1 ]
Gessner, Thomas [2 ]
Li, Mengmeng [1 ]
Chen, Long [1 ]
Eustachi, Michael [2 ]
Weitz, R. Thomas [2 ,3 ]
Li, Chen [1 ]
Muellen, Klaus [1 ]
机构
[1] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany
[2] BASF SE, D-67056 Ludwigshafen, Germany
[3] Ludwig Maximilians Univ Munchen, Dept Phys, Amalienstr 54, D-80799 Munich, Germany
关键词
THIN-FILM TRANSISTORS; HIGH-PERFORMANCE; SEMICONDUCTORS; CHANNEL; MOBILITY; PERYLENE; POLYMER; ELECTRONICS;
D O I
10.1021/acs.orglett.5b03489
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of difluoro- and tetrafluoro-substituted naphthalene diimides (NDIs) were synthesized by halogen exchange reactions of corresponding bromo-NDIs with CsF in dioxane. Two strong electron acceptor molecules 6 and 8 with low-lying LUMO energy levels of -4.27 and -4.54 eV were obtained, starting from tetrafluoro-NDI. Organic field-effect transistors (OFETs) based on these fluorinated NDIs were fabricated by vapor deposition, exhibiting n-channel field-effect character under ambient conditions with the highest mobility of 0.1 cm(2) V-1 s(-1).
引用
收藏
页码:456 / 459
页数:4
相关论文
共 31 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]   Charge transport in organic semiconductors [J].
Coropceanu, Veaceslav ;
Cornil, Jerome ;
da Silva Filho, Demetrio A. ;
Olivier, Yoann ;
Silbey, Robert ;
Bredas, Jean-Luc .
CHEMICAL REVIEWS, 2007, 107 (04) :926-952
[3]   Substituted Heterocyclic Naphthalene Diimides with Unexpected Acidity. Synthesis, Properties, and Reactivity [J].
Doria, Filippo ;
di Antonio, Marco ;
Benotti, Michele ;
Verga, Daniela ;
Freccero, Mauro .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8616-8625
[4]   Synthesis and Properties of Naphthobisbenzothiophene Diimides [J].
Gao, Jing ;
Li, Yan ;
Wang, Zhaohui .
ORGANIC LETTERS, 2013, 15 (06) :1366-1369
[5]   First synthesis of 2,3,6,7-tetrabromonaphthalene diimide [J].
Gao, Xike ;
Qiu, Wenfeng ;
Yang, Xiaodi ;
Liu, Yunqi ;
Wang, Ying ;
Zhang, Hengjun ;
Qi, Ting ;
Liu, Ying ;
Lu, Kun ;
Du, Chunyan ;
Shuai, Zhigang ;
Yu, Gui ;
Zhu, Daoben .
ORGANIC LETTERS, 2007, 9 (20) :3917-3920
[6]   Core-Expanded Naphthalene Diimides Fused with 2-(1,3-Dithiol-2-Ylidene)Malonitrile Groups for High-Performance, Ambient-Stable, Solution-Processed n-Channel Organic Thin Film Transistors [J].
Gao, Xike ;
Di, Chong-an ;
Hu, Yunbin ;
Yang, Xiaodi ;
Fan, Hongyu ;
Zhang, Feng ;
Liu, Yunqi ;
Li, Hongxiang ;
Zhu, Daoben .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3697-+
[7]   Naphthalene Diimide-Based Polymer Semiconductors: Synthesis, Structure-Property Correlations, and n-Channel and Ambipolar Field-Effect Transistors [J].
Guo, Xugang ;
Kim, Felix Sunjoo ;
Seger, Mark J. ;
Jenekhe, Samson A. ;
Watson, Mark D. .
CHEMISTRY OF MATERIALS, 2012, 24 (08) :1434-1442
[8]   Air-Stable n-Channel Organic Single Crystal Field-Effect Transistors Based on Microribbons of Core-Chlorinated Naphthalene Diimide [J].
He, Tao ;
Stolte, Matthias ;
Wuerthner, Frank .
ADVANCED MATERIALS, 2013, 25 (48) :6951-6955
[9]  
Heywang G., 1988, German Patent, Patent No. [DE 3703131A1, 3703131]
[10]   A facile synthesis of 2,3,6,7-tetrabromonaphthalene diimides toward new π-extended naphthalene diimides [J].
Hu, Yunbin ;
Wang, Zhongli ;
Yang, Xiaodi ;
Zhao, Zheng ;
Han, Wenjie ;
Yuan, Wei ;
Li, Hongxiang ;
Gao, Xike ;
Zhu, Daoben .
TETRAHEDRON LETTERS, 2013, 54 (18) :2271-2273