Bis(2-acenyl)acetylene semiconductors

Details Bis(2-acenyl)acetylene semiconductors Bis(2-acenyl)acetylene semiconductors

2006-09-19

2006-09-19

Richter, Johann (Department: 1621)

Active solid-state devices (e.g., transistors, solid-state diode

Organic semiconductor material

C552S271000, C585S026000

Reexamination Certificate

active

07109519

ABSTRACT:
Bis(2-acenyl)acetylene compounds that are useful as organic semiconductors are disclosed. The compounds, when used as the active layer in OTFTs 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: 5347144 (1994-09-01), Garnier et al.
patent: 5956679 (1999-09-01), Komori et al.
patent: 6215130 (2001-04-01), Dodabalapur
patent: 6265243 (2001-07-01), Katz et al.
patent: 6288188 (2001-09-01), Godschalx et al.
patent: 6433359 (2002-08-01), Kelley 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: 2003/0150384 (2003-08-01), Baude et al.
patent: 0 275 075 (1988-07-01), None
patent: 0 744 406 (1996-11-01), None
patent: WO 93/09079 (1993-05-01), None
patent: WO 93/09079 (1993-05-01), None
C. D. Sheraw et al., “Organic Thin-Film Transistor-Driven Polymer-Dispersed Liquid Crystal Displays on Flexible Polymeric Substrates”, Applied Physics Letter, (Feb. 11, 2002), pp. 1088-1090, vol. 80, No. 6, American Institute of Physics, Melville, NY.
C. D. Dimitrakopoulos, et al., “Organic Thin Film Transistors for Large Area Electronics”, Advanced Materials, (Jan. 16, 2002), pp. 99-117, vol. 14, No. 2, WILEY-VCH-Verlag GmbH, D-69469 Weinheim, Germany.
A. Kraft, “Organic Field-Effect Transistors—The Breakthrough at Last”, CHEMPHYSCHEM, (2001), pp. 163-165, vol. 2, WILEY-VCH-Verlag GmbH, D-69451, Weinheim, Germany.
S. J. Martin, “Development of a Low-Dielectric-Constant Polymer for the Fabrication of Integrated Circuit Interconnect”, Advanced Materials, (Dec. 1, 2000), pp. 1769-1778, vol. 12, No. 23, WILEY-VCH-Verlag GmbH, D-69469, Weinheim, Germany.
C. D. Sheraw, “Spin-On Polymer Gate Dielectric for High Performance Organic Thin Film Transistors”, Mat. Res. Soc. Symp. Proc., (2000), pp. 403-408, vol. 558, Materials Research Society.
P. Van Zant, “Microchip Fabrication”, (2000), 4thEdition, McGraw-Hill, NY.
S. M. Sze, “Physics of Semiconductor Devices”, (1981), pp. 492-493, 2thEdition, John Wiley & Sons, NY.
K. Ito, “Oligo(2,6-anthrylene)s: Acence-Oligomer Approach for Organic Field-Effect Transistors”, Angewandte Chemie International Edition, (2003), pp. 1159-1162, vol. 42, No. 10, WILEY-VCH-Verlag GmbH & Co. KGaA, Weinheim, Germany.
H. E. Katz, “Synthetic Chemistry for Ultrapure, Processable, and High-Mobility Organic Transistor Semiconductors”, Accounts of Chemical Research, (May 2001), pp. 359-369, vol. 34, No. 5, Amercian Chemical Society, Washington, DC.
“Organic Reactions”, (1997), vol. 50, John Wiley & Sons, Inc., NY.
A. F. Littke et al., “Pd/P(t-Bu)3: A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides”, Journal of the American Chemical Society, (Jun. 5, 2002), pp. 6343-6348, vol. 124, No. 22, American Chemical Society, Washington, DC.
J. E. Banks, “Cyclic Hydrocarbons and Substituted Hydrocarbons”, Naming Oragnic Compounds, (1976), p. 124, 2ndEdition, W. B. Saunders Co., Philadelphia, PA.
D. J. Gundlach et al., “Solvent-Induced Phase Transition in Thermally Evaporated Pentacene Films”, Applied Physics Letters, (May 31, 1999), pp. 3302-3304, vol. 74, No. 22, American Institute of Physics, Melville, NY.
H. Klauk et al., “High-Mobility Polymer Gate Dielectric Pentacene Thin Film Transistors”, Journal of Applied Physics, (Nov. 1, 2002), pp. 5259-5263, vol. 92, No. 9, American Institute of Physics, Melville, NY.
D. Knipp et al., “Pentacene Thin Film Transistors on Inorganic Dielectrics: Morphology, Structural Properties, and Electronic Transport”, Journal of Applied Physics, (Jan. 1, 2003), pp. 347-355, vol. 93, No. 1, American Intstitute of Physics, Melville, NY.
T. W. Kelley et al., “High-Performance OTFTs Using Surface-Modified Alumina Dielectrics”, Journal of Physical Chemistry, (Jun. 19, 2003), pp. 5877-5881, vol. 107, No. 24, American Chemistry Society.
H. Sirringhaus et al., “Mobility Enhancement in Conjugated Polymer Field-Effect Transistors Through Chain Alignment in a liquid-Crystalline Phase”, Applied Physics Letters, (Jul. 17, 2000), pp. 406-408, vol. 77, No. 3, American Institute of Physics, Melville, NY.
U.S. Appl. No. 10/434,377, filed May 8, 2003, entitled “Organic Polymers, Electronic Devices, and Methods”.
U.S. Appl. No. 10/328,461, filed Dec. 23, 2002, entitled “AC Powered Logic Circuitry”.
Liu et al., “Photophysical Behaviors of Oligomer Based on 1,1′-Binaphthol with 3,3'-Acetylene Spacer”, Chinese Journal of Polymer Science, (1998), pp. 234-240, vol. 16, No. 3.
Schmidt et al., “2,2′-(Ethynediyl)bis(4-alkoxy-1-naphthols)and Dinaphthofuro[3,2-b] furans—Substances with Unusual Photoreactivity and Photochromic Behavior”, Angew. Chem. Int. Ed. Engl., (1991), pp. 866-867, vol. 30, No. 7.
Murai et al., “Development of Novel Heterobimetallic Catalyst Using Linked BINOL as a Ligand and its Application to Tandem Henry Reaction”, pp. 60-61, The Institute of Scientific and Industrial Research, Osaka University, Japan.
Hird et al., “The Synthesis and High Optical Birefringence of Nematogens Incorporating 2,6-disubstituted Naphthalenes and Terminal Cyano-Substituents”, Liquid Crystals, (1993), pp. 123-150, vol. 15, No. 2.
Meng et al., “Stepwise Synthesis and Characterization of Oligomers Based on 1,1′-binaphthol with 3,3′-acetylene Spacer”, Tetrahedron: Asymmetry 9 (1998), pp. 3693-3707, Elsevier Science Ltd.
Li, et al., “Palladium Catalysed Polymerization of Aryl Diodides with Acetylene Gas in Aqueous Medium: A Novel Synthesis of Areneethynylene Polymers and Oligomers”, Chem. Commun., (1997) pp. 1569-1570.
Tayama et al., “Activation of Ether Functionality of Allyl Vinyl Ethers by Chiral Bis(organoaluminum)Lewis Acids: Application to Asymmetric Claisen Rearrangement”, Tetrahedron 58, (2002), pp. 8307-8312, Elsevier Science Ltd.
Wang et al., “Enantiometric Discrimination of Chiral Amines with New Fluorescent Chemosensors”, Chem. Commun., (1998), pp. 1747-1748.
Yin et al., “A Synthesis of Trisquinones”, J. Org. Chem., (1998), pp. 5726-5727, vol. 63, American Chemical Society.

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