Organic n-channel transistors based on core-cyanated perylene carboxylic diimide derivatives.

Five core-cyanated perylene carboxylic diimides end-functionalized with fluorine-containing linear and cyclic substituents have been synthesized and employed in the fabrication of air-stable n-channel organic thin-film field-effect transistors with carrier mobilities up to 0.1 cm2/Vs. The relationships between molecular structure, thin-film morphology, substrate temperature during vacuum deposition, transistor performance, and air stability have been investigated. Our experiments led us to conclude that the role of the fluorine functionalization in the air-stable n-channel operation of the transistors is different than previously thought.

[1]  P. Lin,et al.  High-performance bottom-contact devices based on an air-stable n-type organic semiconductor N,N-bis (4-trifluoromethoxybenzyl)-1,4,5,8-naphthalene-tetracarboxylic di-imide , 2007 .

[2]  Zhenan Bao,et al.  Air‐Stable n‐Channel Organic Semiconductors Based on Perylene Diimide Derivatives without Strong Electron Withdrawing Groups , 2007 .

[3]  Antonio Facchetti,et al.  Semiconductors for organic transistors , 2007 .

[4]  Zhenan Bao,et al.  Complementary inverter using high mobility air-stable perylene di-imide derivatives , 2007 .

[5]  H. Ishii,et al.  Air-stable n-channel organic field-effect transistors based on N,N′-bis(4-trifluoromethylbenzyl)perylene-3,4,9,10-tetracarboxylic diimide , 2007 .

[6]  H. Klauk,et al.  Ultralow-power organic complementary circuits , 2007, Nature.

[7]  J. Gómez‐Herrero,et al.  WSXM: a software for scanning probe microscopy and a tool for nanotechnology. , 2007, The Review of scientific instruments.

[8]  Zhenan Bao,et al.  Air Stable n-Channel Organic Semiconductors for Thin Film Transistors Based on Fluorinated Derivatives of Perylene Diimides , 2007 .

[9]  Zhenan Bao,et al.  Air-stable n-channel copper hexachlorophthalocyanine for field-effect transistors , 2006 .

[10]  Yoshio Taniguchi,et al.  High mobility n-type thin-film transistors based on N,N′-ditridecyl perylene diimide with thermal treatments , 2006 .

[11]  Tobin J Marks,et al.  Gate dielectric chemical structure-organic field-effect transistor performance correlations for electron, hole, and ambipolar organic semiconductors. , 2006, Journal of the American Chemical Society.

[12]  Tobin J Marks,et al.  Fluorocarbon-modified organic semiconductors: molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties. , 2006, Journal of the American Chemical Society.

[13]  D. Gundlach,et al.  High mobility n-channel organic thin-film transistors and complementary inverters , 2005 .

[14]  Shizuo Tokito,et al.  Organic Thin-Film Transistors with High Electron Mobility Based on Perfluoropentacene , 2005 .

[15]  Richard H. Friend,et al.  General observation of n-type field-effect behaviour in organic semiconductors , 2005, Nature.

[16]  Tobin J Marks,et al.  High-mobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides). , 2004, Angewandte Chemie.

[17]  Heinz von Seggern,et al.  n-type organic field-effect transistor based on interface-doped pentacene , 2004 .

[18]  M. Ratner,et al.  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. , 2004, Journal of the American Chemical Society.

[19]  A. Facchetti,et al.  Synthesis and characterization of diperfluorooctyl-substituted phenylene-thiophene oligomers as n-type semiconductors. Molecular structure-film microstructure-mobility relationships, organic field-effect transistors, and transistor nonvolatile memory elements , 2004 .

[20]  Fumio Sato,et al.  Perfluoropentacene: high-performance p-n junctions and complementary circuits with pentacene. , 2004, Journal of the American Chemical Society.

[21]  Tobin J Marks,et al.  Building blocks for n-type organic electronics: regiochemically modulated inversion of majority carrier sign in perfluoroarene-modified polythiophene semiconductors. , 2003, Angewandte Chemie.

[22]  Hongzheng Chen,et al.  Fluoroperylene diimide: a soluble and air-stable electron acceptor , 2003 .

[23]  Akihiko Fujiwara,et al.  Fabrication and characterization of C60 thin-film transistors with high field-effect mobility , 2003 .

[24]  Tobin J. Marks,et al.  n‐Type Building Blocks for Organic Electronics: A Homologous Family of Fluorocarbon‐Substituted Thiophene Oligomers with High Carrier Mobility , 2003 .

[25]  Alessandro Curioni,et al.  N-type organic thin-film transistor with high field-effect mobility based on a N,N′-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative , 2002 .

[26]  B. Das,et al.  Design and synthesis of N-nonpolar nucleobase dipeptides: application of the Ugi reaction for the preparation of dipeptides having fluoroarylalkyl groups appended to the nitrogen atom , 2002 .

[27]  H. Sirringhaus,et al.  Tuning the Semiconducting Properties of Sexithiophene by alpha,omega-Substitution-alpha,omega-Diperfluorohexylsexithiophene: The First n-Type Sexithiophene for Thin-Film Transistors We thank DARPA (N00421-98-1187) and the NSF-MRSEC program through the Northwestern Materials Research Center (DMR-9632 , 2000, Angewandte Chemie.

[28]  H. Sirringhaus,et al.  Tuning the Semiconducting Properties of Sexithiophene by α,ω‐Substitution—α,ω‐Diperfluorohexylsexithiophene: The First n‐Type Sexithiophene for Thin‐Film Transistors , 2000 .

[29]  Howard E. Katz,et al.  Naphthalenetetracarboxylic Diimide-Based n-Channel Transistor Semiconductors: Structural Variation and Thiol-Enhanced Gold Contacts , 2000 .

[30]  A. Dodabalapur,et al.  A soluble and air-stable organic semiconductor with high electron mobility , 2000, Nature.

[31]  Kuniaki Tanaka,et al.  Determination of effects of purity and atmospheric gases on electrical properties of perylene thin films by field effect measurement , 1999 .

[32]  Zhenan Bao,et al.  New Air-Stable n-Channel Organic Thin Film Transistors , 1998 .

[33]  D. M. Leeuw,et al.  Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices , 1997 .

[34]  A. J. Lovinger,et al.  n-Channel Organic Transistor Materials Based on Naphthalene Frameworks , 1996 .

[35]  T. Threlfall Analysis of organic polymorphs. A review , 1996 .

[36]  Gilles Horowitz,et al.  Evidence for n‐type conduction in a perylene tetracarboxylic diimide derivative , 1996 .

[37]  Robert C. Haddon,et al.  C60 thin film transistors , 1995 .

[38]  N. Karl,et al.  Structure of perylene-tetracarboxylic-dianhydride thin films on alkali halide crystal substrates , 1992 .

[39]  J. Mizuguchi,et al.  Strikingly different electronic spectra of structurally similar perylene imide compounds , 2006 .

[40]  Peter Atkins,et al.  Physical Chemistry (7th ed.) , 2002 .

[41]  A. F. Hebard,et al.  C-60 thin-film transistors , 1996 .

[42]  H. Wolf The Electronic Spectra of Aromatic Molecular Crystals , 1959 .