Compositions – Electrically conductive or emissive compositions – Metal compound containing
Reexamination Certificate
2011-07-05
2011-07-05
Kopec, Mark (Department: 1766)
Compositions
Electrically conductive or emissive compositions
Metal compound containing
C428S690000, C257S040000, C257S102000, C257S103000
Reexamination Certificate
active
07972541
ABSTRACT:
The present invention relates to a doped organic semiconductor material comprising at least one organic matrix material, which is doped with at least one dopant, the matrix material being selected from a group consisting of certain phenanthroline derivatives; and also an organic light-emitting diode which comprises such a semiconductor material.
REFERENCES:
patent: 2566208 (1951-08-01), Jenkins
patent: 3083242 (1963-03-01), Ramsden
patent: 3226450 (1965-12-01), Blazejak
patent: 3558671 (1971-01-01), Martin
patent: 3563751 (1971-02-01), Cohen
patent: 4003943 (1977-01-01), Fukunaga
patent: 4066569 (1978-01-01), Lim
patent: 4133821 (1979-01-01), West et al.
patent: 4618453 (1986-10-01), Kim
patent: 4960916 (1990-10-01), Pazik et al.
patent: 5093698 (1992-03-01), Egusa
patent: 5110835 (1992-05-01), Walter et al.
patent: 5247226 (1993-09-01), Sato et al.
patent: 5281730 (1994-01-01), Zambounis et al.
patent: 5292881 (1994-03-01), Berneth et al.
patent: 5393614 (1995-02-01), Nakada
patent: 5556524 (1996-09-01), Albers
patent: 5811833 (1998-09-01), Thompson
patent: 5840217 (1998-11-01), Lupo et al.
patent: 5922396 (1999-07-01), Thompson et al.
patent: 6013384 (2000-01-01), Kido et al.
patent: 6013982 (2000-01-01), Thompson et al.
patent: 6103459 (2000-08-01), Diel et al.
patent: 6207835 (2001-03-01), Reiffenrath et al.
patent: 6350534 (2002-02-01), Boerner et al.
patent: 6423429 (2002-07-01), Kido et al.
patent: 6451415 (2002-09-01), Forrest et al.
patent: 6524728 (2003-02-01), Kijima et al.
patent: 6700058 (2004-03-01), Nelles et al.
patent: 6747287 (2004-06-01), Toguchi et al.
patent: 6824890 (2004-11-01), Bazan et al.
patent: 6908783 (2005-06-01), Kuehl et al.
patent: 6972334 (2005-12-01), Shibanuma et al.
patent: 7081550 (2006-07-01), Hosokawa et al.
patent: 7345300 (2008-03-01), Qin
patent: 2003/0064248 (2003-04-01), Wolk
patent: 2003/0165715 (2003-09-01), Yoon et al.
patent: 2003/0234397 (2003-12-01), Schmid et al.
patent: 2004/0068115 (2004-04-01), Lecloux et al.
patent: 2004/0076853 (2004-04-01), Jarikov et al.
patent: 2005/0040390 (2005-02-01), Pfeiffer et al.
patent: 2005/0061232 (2005-03-01), Werner et al.
patent: 2005/0072971 (2005-04-01), Marrocco et al.
patent: 2005/0086251 (2005-04-01), Hatscher et al.
patent: 2005/0110009 (2005-05-01), Blochwitz-Nimoth et al.
patent: 2005/0121667 (2005-06-01), Kuehl et al.
patent: 2005/0123793 (2005-06-01), Thompson et al.
patent: 2005/0231100 (2005-10-01), Elliott et al.
patent: 2006/0049397 (2006-03-01), Pfeiffer et al.
patent: 2006/0138453 (2006-06-01), Thompson et al.
patent: 2006/0204783 (2006-09-01), Conley et al.
patent: 2007/0026257 (2007-02-01), Begley et al.
patent: 2007/0058426 (2007-03-01), Sokolik et al.
patent: 2007/0252140 (2007-03-01), Limmert et al.
patent: 2007/0090371 (2007-04-01), Drechsel et al.
patent: 2007/0116984 (2007-05-01), Park et al.
patent: 2007/0145355 (2007-06-01), Werner et al.
patent: 2008/0103315 (2008-05-01), Egawa et al.
patent: 2008/0122345 (2008-05-01), Sakata et al.
patent: 2008/0145708 (2008-06-01), Heil et al.
patent: 2008/0265216 (2008-10-01), Hartmann et al.
patent: 2549309 (2005-09-01), None
patent: 354065 (1961-05-01), None
patent: 354066 (1961-05-01), None
patent: 19836408 (2000-02-01), None
patent: 10261662 (2004-07-01), None
patent: 1000998 (2000-05-01), None
patent: 61254582 (1986-11-01), None
patent: 63172274 (1988-07-01), None
patent: 63172275 (1988-07-01), None
patent: 04338760 (1992-11-01), None
patent: 7168377 (1995-07-01), None
patent: 2004010703 (2004-01-01), None
patent: 2004335557 (2004-11-01), None
patent: 03088271 (2003-10-01), None
patent: WO 03088271 (2003-10-01), None
patent: WO 03/104237 (2003-12-01), None
patent: 2005086251 (2005-09-01), None
patent: WO 2005086251 (2005-09-01), None
patent: WO 2006/067800 (2006-06-01), None
patent: WO 2008/022633 (2008-02-01), None
Akiba, Kin-Ya et al., “Direct Synthesis of 2,2-diaryl-3-methyl-2,3-dihydrobenzothiazoles from 3-methyl-2,3-dihydrobenzothiazole-2-thione and some mechanistic aspects,” Bulletin of the Chemical Society of Japan, vol. 52(1), pp. 156-159, (1979).
Akutagawa., T. et al. “Multi Electron and Proton-Transfer System Based on 2,2′-biimidazole derivatives,” Science and Technology of Syn. Metals, 1994, 346.
Alonso, R. A. et al. “Photostimulated Reaction of Diphenylarsenide and Diphenylstibide Ions with Haloaromatic Compounds by the Srn1 Mechanism. Electron Transfer vs. Bond Breaking of the Radical Anion Intermediate,” J. Org. Chem. (1982) 47(1) pp. 77-80.
Auch et al. “Eine neue Synthese und die Kristallstrukturanalyse von., Krokonat-Blau . . . ,” Chem. Ber. 120, 1691-1696 (1987), extract, pp. 1691-1693, 6 total pages.
Bach, U. et al. “Solid-state dye-sensitized mesoporous TiO2solar cells with high photon-to-electron conversion efficiencies,” Nature, vol. 395, Oct. 8, 1998, pp. 583-585.
Bamgboye, T.T. et a. “Lewis acidity of Ph2SbX3, wherein X = Cl or Br. Crystal structures of Ph2SbCl3*H20 and Ph2SbBr3*MeCN,” J. of Organometallic Chem. vol. 362, Feb. 28, 1989, pp. 77-85.
Barton, D.H.R. et al. “Comparative Arylation Reactions with Pentaphenylbismuth and with Triphenylbismuth Carbonate,” J. Chem. Soc. Chem. Commun. (1980) 17, pp. 827-829.
Baumgartel, H. et al., “Polarographische Untersuchungen zur Konformation von 1.2.3.4.5-pentaarylimidazoliumkationen,” Ber. Bunsenges (1972) 76/2, 94-100.
Baumgartel, H. et al., “Uber eine neue Synthese von tetraaryl-imidazolen und pentaaryl-imidazolium-salzen,” Chem. Ber. (1968), 101, 3504.
Bhattacharya, S.N. et al. “Preparation & Characterization of Some Triarylarsenic & Triarylantimony Mixed Halides & Related Compounds,” Indian J. Chem. 16A (1978) pp. 778-781.
Blinka et al. “Octacyanotetramethylenecyclobutane Dianioin and its Anion-Radical,” Tetrahedron Lett. (1983). vol. 24, No. 1567-1568.
Blochwitz, J., et al., “Low voltage organic light emitting diodes featuring doped phthalocyanine as hole transport material,” Applied Physics Letters, vol. 73, No. 6, Aug. 10, 1998, pp. 729-731.
Bonati, F. et al. “Reactions of C-imidazolyllithium derivatives with Broup Ib compounds: tris[micro-(1-alkylimidazolato-N3, C2)]tri-gold (I) and -silver (I),” J. Organomet. Chem. 1989, 375, pp. 147-160.
Brucsis, L. et al. “Substituionasreaktionen an 1,4-dihalogen-2,3,5,6-tetracyan-benzolen,” Chem. Ber. 109(1976) pp. 2469-2474.
Cherkashin M. I. et al. “Studies on 2,4,5-triarylimidazoles,” Izv. Akad. Nauk SSSR, Seriya Khim. 1982, 2, pp. 376-377.
Chonan et al. “The synthesis of difluoro and dimethyl derivatives of 2,6-bis(dicyanomethylene)-2,6-dihydro-4H-cyclopenta[2, l-b:3,4-b′]-dithiophen-4-one (CPDT-TCNQ) and the Conducting Properties of the Metallic Salts Based on the Dimethy Derivative,” The Chemical Society of Japan (2004) pp. 1487-1497.
Curini, M. et al., “Ytterbium Triflate Promoted Synthesis of Benzimidazole Derivatives,” Synlett, No. 10, pp. 1832-1834, 2004.
Dedik, S.G. et al. “Tetrahalotetraazafulvalenes—new strong electron acceptors,” Chemistry of Heterocyclic Compounds (A Translation of Khimiyageterotsiklicheskikh Soedinenii), Plenum Press Co., New York, U.S., vol. 10, Jan. 1, 1989, p. 1421.
Deluca, Mark et al., “The p-toluenesulfonic acid promoted synthesis of 2-substituted benzoxazoles and benzimidazoles from diacylated precursors,” Tetrahedron, vol. 53, No. 2, pp. 457-464, 1997.
Endo, Jun et al., “Organic Electroluminescent Devices with a vacuum-deposited Lewis Acid doped hole injecting layer,” Japan Society of Applied Physics, vol. 41, 2002, pp. L358-L360, Part 2, No. 3B, Mar. 15, 2002.
Fatiadi et al. “Electrochemical Oxidation of Several Oxocarbon Salts in N,N-dimethylformamide,” J. Electroanalytical Chem. (1982) vol. 135, pp. 193-209.
Fatiadi, “Psuedooxocarbons, Synthesis of 1,2,3-tris(dicyanomethylene)croconate Salts; A New Bond-Delocalized Dianion, Croconate Bl
Lux Andrea
Salbeck Josef
Werner Ansgar
Kopec Mark
Novaled AG
Sutherland & Asbill & Brennan LLP
Thomas Jaison P
LandOfFree
Doped organic semiconductor material does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Doped organic semiconductor material, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Doped organic semiconductor material will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2740270