Air-stable n-channel organic semiconductors based on perylene diimide derivatives without strong electron withdrawing groups

被引:213
作者
Ling, Mang-Mang
Erk, Peter
Gomez, Marcos
Koenemann, Martin
Locklin, Jason
Bao, Zhenan
机构
[1] Stanford Univ, Dept Chem Engn, Stanford, CA 94305 USA
[2] BASF Future Business, D-67056 Ludwigshafen, Germany
[3] BASF AG, D-67056 Ludwigshafen, Germany
关键词
D O I
10.1002/adma.200601705
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two n-channel organic semiconductors based on perylene diimide derivatives without strong electron-withdrawing groups were presented that showed high mobilities and were air-stable. Both compounds, tetrachloroperylene tetracarboxyldiimide (TC-PTCDI) and N,N'-bis(2-phenylethyl)perylene-3,4:9:10- bis-(dicarboximide) (BPE-PTCDI), were used as pigments in paints and as photoconductors. A highly doped n-type Si wafer, with a thermally grown dry oxide layer as the gate dielectric, was used as the substrate. The electrical characteristics of top-contact organic thin-film transistor (OTFT) devices were measured in ambient laboratory conditions by using a Keithley 4200-SCS semiconductor parameter analyzer. Air-stability measurements of TC-PTCDI and BPE-PTCDI TFTs were carried out by monitoring the charge-carrier mobilities and on/off ratios as a function of time. These TFTs were potentially useful air-stable n-type semiconductors for thin-film transistors in CMOS circuits and photovoltaic devices.
引用
收藏
页码:1123 / 1127
页数:5
相关论文
共 26 条
[1]   Organic field-effect transistors with high mobility based on copper phthalocyanine [J].
Bao, Z ;
Lovinger, AJ ;
Dodabalapur, A .
APPLIED PHYSICS LETTERS, 1996, 69 (20) :3066-3068
[2]   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
[3]   Charge-transfer and energy-transfer processes in π-conjugated oligomers and polymers:: A molecular picture [J].
Brédas, JL ;
Beljonne, D ;
Coropceanu, V ;
Cornil, J .
CHEMICAL REVIEWS, 2004, 104 (11) :4971-5003
[4]   Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors:: Studies on structural, electrochemical and charge transport properties [J].
Chen, ZJ ;
Debije, MG ;
Debaerdemaeker, T ;
Osswald, P ;
Würthner, F .
CHEMPHYSCHEM, 2004, 5 (01) :137-140
[5]   Variable temperature film and contact resistance measurements on operating n-channel organic thin film transistors [J].
Chesterfield, RJ ;
McKeen, JC ;
Newman, CR ;
Frisbie, CD ;
Ewbank, PC ;
Mann, KR ;
Miller, LL .
JOURNAL OF APPLIED PHYSICS, 2004, 95 (11) :6396-6405
[6]   Organic thin film transistors based on N-alkyl perylene diimides:: Charge transport kinetics as a function of gate voltage and temperature [J].
Chesterfield, RJ ;
McKeen, JC ;
Newman, CR ;
Ewbank, PC ;
da Silva, DA ;
Brédas, JL ;
Miller, LL ;
Mann, KR ;
Frisbie, CD .
JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (50) :19281-19292
[7]   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
[8]   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
[9]   Building blocks for n-type molecular and polymeric electronics.: Perfluoroalkyl-versus alkyl-functionalized oligothiophenes (nT; n=2-6).: Systematics of thin film microstructure, semiconductor performance, and modeling of majority charge injection in field-effect transistors [J].
Facchetti, A ;
Mushrush, M ;
Yoon, MH ;
Hutchison, GR ;
Ratner, MA ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13859-13874
[10]   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-+