Easily synthesized naphthalene tetracarboxylic diimide semiconductors with high electron mobility in air

被引:114
作者
See, Kvin C. [1 ]
Landis, Chad [1 ]
Sarjeant, Amy [2 ]
Katz, Howard E. [1 ,2 ]
机构
[1] Johns Hopkins Univ, Dept Mat Sci & Engn, Baltimore, MD 21218 USA
[2] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
关键词
D O I
10.1021/cm7032614
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
New N,N'-substituted 1,4,5,8-naphthalene tetracarboxylic diimides (NTCDIs) were synthesized in one step reactions, resulting in excellent electron mobilities in air as measured in organic field effect transistors (OFETs). Two perfluoroalkyl-benzyl N,N' substituents were used, differing in the length of the perfluoroalkyl moieties on the benzyl portion of the molecule. Single crystals of the short chain compound 2 were successfully grown by horizontal vapor deposition, and crystal structures were obtained and analyzed. Devices from both compounds were fabricated on untreated and silane treated Si/SiO2 substrates. The longer chain compound 1 gives the largest field effect mobility, reaching 0.57 cm(2)/(V s) in air. This is competitive with the best air stable n-channel materials to date. In contrast to previously studied high mobility materials, 1 achieved mobilities near 0.4 cm(2)/(V s) without the use of dielectric substrate treatments. Additionally, 1 displays exemplary ordering regardless of surface treatment, as determined from X-ray diffraction, while 2 displays significant improvement in mobility and film structure when deposited on surface treated substrates.
引用
收藏
页码:3609 / 3616
页数:8
相关论文
共 53 条
[1]  
Als-Nielsen J., 2001, ELEMENTS MODERN XRAY
[2]   n-Type organic field-effect transistors with very high electron mobility based on thiazole oligomers with trifluoromethylphenyl groups [J].
Ando, S ;
Murakami, R ;
Nishida, J ;
Tada, H ;
Inoue, Y ;
Tokito, S ;
Yamashita, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :14996-14997
[3]   High electron mobility in ladder polymer field-effect transistors [J].
Babel, A ;
Jenekhe, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13656-13657
[4]   New air-stable n-channel organic thin film transistors [J].
Bao, ZA ;
Lovinger, AJ ;
Brown, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) :207-208
[5]   Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters [J].
Briseno, Alejandro L. ;
Mannsfeld, Stefan C. B. ;
Reese, Colin ;
Hancock, Jessica M. ;
Xiong, Yujie ;
Jenekhe, Samson A. ;
Bao, Zhenan ;
Xia, Younan .
NANO LETTERS, 2007, 7 (09) :2847-2853
[6]   N- and P-channel transport behavior in thin film transistors based on tricyanovinyl-capped oligothiophenes [J].
Cai, Xiuyu ;
Burand, Michael W. ;
Newman, Christopher R. ;
da Silva Filho, Demetrio A. ;
Pappenfus, Ted M. ;
Bader, Mamoun M. ;
Bredas, Jean-Luc ;
Mann, Kent R. ;
Frisbie, C. Daniel .
JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (30) :14590-14597
[7]   Air stable n-channel organic semiconductors for thin film transistors based on fluorinated derivatives of perylene diimides [J].
Chen, H. Z. ;
Ling, M. M. ;
Mo, X. ;
Shi, M. M. ;
Wang, M. ;
Bao, Z. .
CHEMISTRY OF MATERIALS, 2007, 19 (04) :816-824
[8]   A novel organic n-type material: fluorinated perylene diimide [J].
Chen, HZ ;
Shi, MM ;
Aernouts, T ;
Wang, M ;
Borghs, G ;
Heremans, P .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2005, 87 (1-4) :521-527
[9]   Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices [J].
deLeeuw, DM ;
Simenon, MMJ ;
Brown, AR ;
Einerhand, REF .
SYNTHETIC METALS, 1997, 87 (01) :53-59
[10]   SUBSTITUENT EFFECTS IN PORPHYRAZINES AND PHTHALOCYANINES [J].
GHOSH, A ;
GASSMAN, PG ;
ALMLOF, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :1932-1940