Semiconductor device manufacturing: process – Having organic semiconductive component
Reexamination Certificate
2007-10-02
2007-10-02
Baumeister, B. William (Department: 2891)
Semiconductor device manufacturing: process
Having organic semiconductive component
C257S040000, C257SE51006, C549S029000, C252S500000
Reexamination Certificate
active
11256281
ABSTRACT:
Acene-thiophene compounds are disclosed that are useful as organic semiconductors. The compounds, when used as the semiconductor layer in organic thin-film transistors exhibit device characteristics, like charge-carrier mobilities and current on/off ratios, that are comparable to those of pentacene. Also described are semiconductor devices comprising at least one compound of the invention; and articles comprising the semiconductor devices such as thin film transistors or transistor arrays, and electroluminescent lamps.
REFERENCES:
patent: 4645777 (1987-02-01), Burkart et al.
patent: 5347144 (1994-09-01), Garnier et al.
patent: 5546889 (1996-08-01), Wakita et al.
patent: 5956679 (1999-09-01), Komori et al.
patent: 6265243 (2001-07-01), Katz et al.
patent: 6288188 (2001-09-01), Godschaix et al.
patent: 6291621 (2001-09-01), Tan et al.
patent: 6312811 (2001-11-01), Frigoli et al.
patent: 6326640 (2001-12-01), Shi et al.
patent: 6355365 (2002-03-01), Hotta et al.
patent: 6359149 (2002-03-01), Tan et al.
patent: 6452207 (2002-09-01), Bao
patent: 6872801 (2005-03-01), Ong et al.
patent: 2003/0094959 (2003-05-01), Hoisington et al.
patent: 2003/0102471 (2003-06-01), Kelley et al.
patent: 2003/0105365 (2003-06-01), Smith et al.
patent: 2004/0067387 (2004-04-01), Kim et al.
patent: 2004/0119049 (2004-06-01), Heeney et al.
patent: 2006/0102890 (2006-05-01), Yamahara et al.
patent: 1 041 652 (2000-10-01), None
patent: 2-218716 (1990-08-01), None
patent: 2001-313176 (2001-11-01), None
patent: 2002-097465 (2002-04-01), None
patent: WO 03/095445 (2003-11-01), None
patent: WO 2004009679 (2004-01-01), None
Kelley, T. W.; Boardman, L. D.; Dunbar, T. D.; Muyres, D. V.; Pellerite, M.; Smith, T. P.; “High-Performance OTFTs Using Surface-Modified Alumina Dielectrics”,J. Phys. Chem. B2003, vol. 107, No. 24, pp. 5877-5881.
Knipp, D.; Street, R. A.; Völkel, A.; Ho, J., “Pentacene Thin Film Transistors on Inorganic Dielectrics: Morphology, Structural Properties, and Electronic Transport”,Journal of Applied. Physics, vol. 93, No. 1, Jan. 1, 2003, pp. 347-355.
Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Radlik, W.; Weber, W.;Journal of Applied. Physics, Nov. 1, 2002, vol. 92, No. 9, pp. 5259-5263.
Mattheus, C. C.; de Wijs, G. A.; de Groot, R. A.; Palstra, T. T. M.; “Modeling The Polymorphism Of Pentacene”,J. Am. Chem. Soc.2003, vol. 125, pp. 6323-6330.
Gundlach et al., “Solvent-Induced Phase Transition In Thermally Evaporated Pentacene Films”,Applied Physics Letters, 2000, vol. 74, No. 22, May 31, 1999, pp. 3302-3304.
Gundlach et al., “Thin-film Transistors Based on Well-Ordered Thermally Evaporated Naphthacene Films”, vol. 80, No. 16, Apr. 22, 2002, Applied Physics Letters, pp. 2925-2927.
James E. Banks,Naming Organic Compounds: A Programmed Introduction To Organic Chemistry, W. B. Saunders College Publishing, PA (1976) pp. 124.
Littke, A. F.; Schwarz, L.; Fu, G. C.; “Pd/P(t-Bu)3: A Mild and General Catalyst For Stille Reactions Of Aryl Chlorides and Aryl Bromides”,J. American Chem. Soc., vol. 124, pp. 6343-6348.
Farina, V.; Krishnamurthy, V.,Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc., 1997; vol. 50.
Ito, K.; Suzuki, T.; Sakamoto, Y.; Kubota, D.; Inoue, Y.; Sato, F; Tokito, S.; “Oligo(2,6-anthrylene)s: Acene-Oligomer Approach For Organic Field-Effect Transistors”,Angewandte Chem., Int. Ed. 2003, vol. 42, No. 10, pp. 1159-1162.
Katz, H.E.; Bao, Z.; Gilat, S. L.; “Synthetic Chemistry For Ultrapure, Processable, and High-Mobility Organic Transistor Semiconductors”,Accounts of Chemical Research, 2001, vol. 34, No. 5, pp. 359-369.
Miller, L. L.; Yuan, Y., “Synthesis of β-Methoxy, Methyl-Capped α-Oligothiophenes”,J. Org. Chem., 1995, vol. 60, No. 21, pp. 6813-6819.
Kirschbaum, T.; Briehn, C. A.; Bäuerle, P.,J. Chem. Soc., Perkin Trans.1, 2000, pp. 1211-1216.
S. M. Sze,Physics of Semiconductor Devices, 2ndEdition, John Wiley and Sons, New York (1981), pp. 492-493.
Peter Van Zant inMicrochip Fabrication, Fourth Edition, McGraw-Hill, New York (2000).
C.D. Sheraw et al., “Spin-On Polymer Gate Dielectric For High Performance Organic Thin Film Transistors”, Materials Research Society Symposium Proceedings vol. 558, Materials Research Society, Warrendale, PA, USA, pp. 403-408 (2000).
Sheraw, C. D.; Zhou, L.; Huang, J. R.; Gundlach, D. J.; Jackson, T. N.; Kane, M. G.; Hill, I. G.; Hammond, M. S.; Campi, J.; Greening, B. K.; Franci, J.; West, J. “Organic Thin-Film Transistor-Driven Polymer-Dispersed Liquid Crystal Displays On Flexible Polymeric Substrates”,Applied Physics Letters, 2002, vol. 80, No. 6, pp. 1088-1090.
Meng, H.; Bao, Z.; Lovinger, A.J.; Wang, B. C.; Mujsce, A. M., “High Field-Effect Mobility Oligofluorene Derivatives With High Environmental Stability”,J. Am. Chem. Soc., 2001, 123, pp. 9214-9215.
Sirringhaus, H.; Kawase, T.; Friend, R. H.; Shimoda, T.; Inbasekaran, M.; Wu, W.; Woo, E. P.; “High-Resolution Inkjet Printing of All-Polymer Transistor Circuits”,Science(Washington, D.C., 1883-), Dec. 15, 2000, vol. 290, pp. 2123-2126.
Sirringhaus, H.; Wilson, R. J.; Friend, R. H.; Inbasekaran, M.; Wu, W.; Woo, E. P., Grell, M.; Brandley, D. D. C., “Mobility Enhancement In Conjugated Polymer Field-Effect Transistors Through Chain Alignment In A Liquid-Crystalline Phase”,Appl. Phys. Lett.Jul. 17, 2000, vol. 77, No. 3. pp. 406-408.
U.S. Appl. No. 10/434,377, filed May 8, 2003, entitled “Organic Polymers, Electronic Devices, and Methods”.
Martin, J.P., et al., “Development Of A Low-Dielectric-Constant Polymer For The Fabrication Of Integrated Circuit Interconnect”,Adv. Mater.Dec. 1, 2000, vol. 12, No. 23, pp. 1769-1778.
5-tri-n-butylstannyl-2,2′-bithiophene: Zhu, S. S.; Swager, T. M.; “Conducting Polymetallorotaxanes: Metal Ion Mediated enhancements In Conductivity And Charge Localization”,J. Am. Chem. Soc.1997, vol. 119, pp. 12568-12577.
5,5′-bis(tri-n-butylstannyl)-2,2′-bithiophene: Wei, Y.; Yang, Y.; Yeh, J.-M.; “Synthesis and Electronic Properties of Aldehyde End-Capped Thiophene Oligomers and Other α,ω-Substituted Sexithiophenes”,Chem. Mater.1996, vol. 8, No. 11, pp. 2659-2666.
Sotgiu, G.; Zambianchi, M.; Barbarella, G.; Botta, C. “Synthesis And Optical Properties Of Soluble Sexithiophenes With One Central Head-To-Head Junction”,Tetrahedron2002, vol. 58, pp. 2245-2251.
3,4′-dihexyl-2,2′-bithiophene: Kirschbaum, T.; Briehn, C. A.; Bäuerle, P.; “Efficient Solid-Phase Synthesis Of Regioregular Head-To-Tail-Coupled Oligo(3-alkyithiophene)s Up To A Dodecamer”,J. Chem. Soc., Perkin Trans.,. 1, 2000, pp. 1211-1216.
Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C., “Synthesis and Energy Transfer Properties of Terminally substituted Oligothiophenes”,J. Am. Chem. Soc., 1995, 117, pp. 8090-8099.
Netka, J.; Crump, S. L.; Rickborn, B., “Isobenzofuran-Aryne Cycloadducts: Formation And Regioselective Conversion To Anthrones And Substituted polycyclic Aromatics”,J. Org. Chem., 1986, vol. 51, No. 8, pp. 1189-1199.
Marquardt, D. J.; McCormick, F. A., “An Efficient Reduction Of Anthrones To Anthracenes”,Tetrahedron Letters, 1994, vol. 35, No. 8, pp. 1131-1134.
Porzi, G.; Concilio, C. J.,Organomet. Chem., 1977, 128, pp. 95-98.
Medne, R. S.; Livdane, A. D.; Neiland, O. Y., “Production Of Tetracenes By Reduction Of 6,11-Dihydroxy-5,12-Tetracenequinones, Phthalide Derivatives, With Aluminum Cyclohexanolate”,J. Org. Chem. USSR(Engl. Transl.), 1977, 13, pp. 572-575.
K. Y. Musick et al., “Synthesis of Binaphthyl—Oligothiophene Copolymers with Emissions of Different Colors: Systematically Tuning the Photoluminescence of Conjugated Polymers”, Macromolecules, (1998), pp. 2933-2942, vol. 31, American Chemical Society.
A. Rajca et
3M Innovative Properties Company
Baumeister B. William
Bronk John M.
Kokko Kent S.
Such Matthew W.
LandOfFree
Acene-thiophene semiconductors does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Acene-thiophene semiconductors, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Acene-thiophene semiconductors will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3870589