Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2007-03-20
2007-03-20
Dye, Rena (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C252S301160, C252S301350, C252S500000, C257S040000, C313S504000, C313S506000, C548S148000, C548S262200
Reexamination Certificate
active
10414073
ABSTRACT:
Compounds, compositions, organic electronic devices, and methods for preparing organic electronic devices are described. The compounds of the invention contain at least two carbon-carbon triple bonds and a heteroaromatic ring having at least one —C═N— unit. The compounds can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices.
REFERENCES:
patent: 4252671 (1981-02-01), Smith
patent: 5061569 (1991-10-01), VanSlyke et al.
patent: 5166024 (1992-11-01), Bugner et al.
patent: 5256506 (1993-10-01), Ellis et al.
patent: 5351617 (1994-10-01), Williams et al.
patent: 5408109 (1995-04-01), Heeger et al.
patent: 5508136 (1996-04-01), Shirota et al.
patent: 5536588 (1996-07-01), Naito
patent: 5550290 (1996-08-01), Mizuta et al.
patent: 5621131 (1997-04-01), Kreuder et al.
patent: 5681664 (1997-10-01), Tamano et al.
patent: 5693446 (1997-12-01), Staral et al.
patent: 5695907 (1997-12-01), Chang
patent: 5707745 (1998-01-01), Forrest et al.
patent: 5708130 (1998-01-01), Woo et al.
patent: 5710097 (1998-01-01), Staral et al.
patent: 5725989 (1998-03-01), Chang et al.
patent: 5728801 (1998-03-01), Wu et al.
patent: 5792557 (1998-08-01), Nakaya et al.
patent: 5840217 (1998-11-01), Lupo et al.
patent: 5869350 (1999-02-01), Heeger et al.
patent: 5900327 (1999-05-01), Pei et al.
patent: 5929194 (1999-07-01), Woo et al.
patent: 5945502 (1999-08-01), Hsieh et al.
patent: 5998085 (1999-12-01), Isberg et al.
patent: 6030715 (2000-02-01), Thompson et al.
patent: 6074734 (2000-06-01), Kawamura et al.
patent: 6114088 (2000-09-01), Wolk et al.
patent: 6132641 (2000-10-01), Rietz et al.
patent: 6150043 (2000-11-01), Thompson et al.
patent: 6169163 (2001-01-01), Woo et al.
patent: 6194119 (2001-02-01), Wolk et al.
patent: 6203933 (2001-03-01), Nakaya et al.
patent: 6214520 (2001-04-01), Wolk et al.
patent: 6221543 (2001-04-01), Guehler et al.
patent: 6221553 (2001-04-01), Wolk et al.
patent: 6228543 (2001-05-01), Mizuno et al.
patent: 6228555 (2001-05-01), Hoffend, Jr. et al.
patent: 6242115 (2001-06-01), Thomson et al.
patent: 6242152 (2001-06-01), Staral et al.
patent: 6284425 (2001-09-01), Staral et al.
patent: 6329082 (2001-12-01), Kreuder et al.
patent: 6358664 (2002-03-01), Nirmal et al.
patent: 6485884 (2002-11-01), Wolk et al.
patent: 6521324 (2003-02-01), Debe et al.
patent: 6664111 (2003-12-01), Bentsen et al.
patent: 2002/0158574 (2002-10-01), Wolk et al.
patent: 2003/0068525 (2003-04-01), Bellmann et al.
patent: 2003/0124265 (2003-07-01), Bellmann et al.
patent: 2006/0051611 (2006-03-01), Brunner et al.
patent: 3610649 (1987-10-01), None
patent: 0 553 950 (1993-08-01), None
patent: 0650955 (1995-05-01), None
patent: 0827367 (1998-03-01), None
patent: 0879868 (1998-11-01), None
patent: 0891121 (1999-01-01), None
patent: 0953624 (1999-11-01), None
patent: 0968175 (2000-01-01), None
patent: 1 170 273 (2002-01-01), None
patent: 1170273 (2002-01-01), None
patent: 295695/1988 (1988-02-01), None
patent: 191694/1990 (1990-07-01), None
patent: 000792/1991 (1991-01-01), None
patent: 5-152072 (1993-06-01), None
patent: 5-202011 (1993-08-01), None
patent: 6-096860 (1994-04-01), None
patent: 10-195063 (1998-07-01), None
patent: 2000-195673 (2000-07-01), None
patent: WO 98/06773 (1998-02-01), None
patent: WO 98/55561 (1998-12-01), None
patent: WO 99/32537 (1999-07-01), None
patent: WO 99/40655 (1999-08-01), None
patent: WO 00/18851 (2000-04-01), None
patent: WO 00/70655 (2000-11-01), None
patent: WO 01/39234 (2001-05-01), None
patent: WO 01/41512 (2001-06-01), None
patent: WO 02/22374 (2002-03-01), None
patent: WO 03/019179 (2003-03-01), None
Ayabe et al., “Construction of Monomeric and Polymeric Porphyrin Compartments by a Pd(II)-Pyridine Interaction and Their Chiral Twisting by a BINAP Ligand”, Journal of Organic Chemistry, vol. 68, No. 3, pp. 1059-1066 (2003).
Ikeda et al., “A Novel Self-Assembled Porphyrin Polymer Constructed by a Pd(II)-Pyridine Interaction”, Chemical Letters, vol. 11, pp. 1138-1139 (2001).
Tomizaki et al., “Practical Synthesis of Perylene-Monoimide Building Blocks That Possess Features Appropriate For Use In Porphyrin-Based Light-Harvesting Arrays”, Tetrahedron, vol. 59, No. 8, pp. 1191-1207 (2003).
Tomizaki et al., “Synthesis and Photophysical Properties of Light-Harvesting Arrays Comprised of a Porphyrin Bearing Multiple Perylene-Monoimide Accessory Pigments”, Journal of Organic Chemistry, vol. 67, pp. 6519-6534 (2002).
Cha et al., “Synthesis and Luminescence Properties of Four-Armed Conjugated Structures Containing 1,3,4-oxadiazole Moieties”, Journal of Materials Chemistry, vol. 13, No. 8, pp 1900-1904 (2003).
Nam et al., “Photoluminescence and Electroluminescence Properties of Poly(9-vinylcarbarzole)Doped With Anthracene Derivatives Containing bis(ethynylphenyl oxadiazole)or bis(vinylphenyl oxadiazole)Substituents”, Synthetic Metals, vol. 130, No. 3, pp. 271-277 (2002).
Amashukeli et al.,J. Phys. Chem. A., 106(33) 7593-7598 (2002).
Bailey, T.R.,Tetrahedron Lett., 27, 4407-4410 (1986).
Barton et al.,Tetrahedron Lett., 24 (15) 1601-1604 (1983).
Bettenhausen et al.,Synthetic Metals, 91, 223-228 (1997).
Bokova et al.,J. Org. Chem. USSR(Engl. Transl), 5, 1103-1106 (1969).
Brownstein, S.K., et al.,J. Org. Chem., 67, 663 (2002).
Bumagin, N.A. et al.,J. Organomet. Chem., 364 231-234 (1989).
Chen, C.H., et al., “Recent Developments in Molecular Organic Electroluminescent Materials,”Macromolecular Symposia, 125, 1-48 (1997).
Clayden, J., et al.,J. Chem. Soc., Perkin Trans, 1, 7 (1995).
Creason, S.C., et al.,J. Org. Chem. 37, 4440-4446 (1972).
Fischer,Chem Ber., 25, 2826-2846 (1892).
Friend, R.H., et al., “Electroluminescence in Conjugated Polymers”,Nature, 121, 397 (1999).
Fritsch, et al.,Chem Ber., 125, 849-855 (1992).
Fujikawa, et al.,Synthetic Metals, 91, 161-162 (1997).
Gautun et al.,Acta Chem. Scand., 45(6), 609-615 (1991).
Goodbrand et al.,J. Org. Chem. 64, 670-674 (1999).
Grazulevicius, J.V. et al., “Charge-Transporting Polymers and Molecular Glasses”,Handbook of Advanced Electronic and Photonic Materials and Devices, H.S. Nalwa (ed.), 10, 233-274 (2001).
Grekov et al.,J. Gen. Chem. USSR(Engl. Transl) 30, 3763-3766 (1960).
Halls, J.J.M., et al., “Light-emitting and Photoconductive Diodes Fabricated with Conjugated Polymers,”Thin Solid Films, 276, 13-20 (1996).
Huntress et al.,J. Am. Chem. Soc., 55, 4262-4270 (1933).
Ishiyama et al.,J. Org. Chem., 60, 7508-7510 (1995).
Kajino et al.,Chem. Pharm. Bull, 39 (11), 2888-2895 (1991).
Kido, J., “Organic Electroluminescent Devices Based on Polymeric Materials,”Trends in Polymer Science, 2, 350-355 (1994).
Klingsberg, E.J. Org. Chem., 23, 1086-1087 (1958).
Koene, B.E., et al.,Chem. Mater., 10, 2235-2250 (1998).
Kraft, et al.,Angew. Chem. Int. Ed., 37, 402-428 (1998).
Kreger, K. et al.,Synthetic Metals, 119, 163 (2001).
Kristensen et al.,Org. Lett., 10, 1435-1438 (2001).
Meng, et al.,J. Am. Chem. Soc., 123(37), 9214-9215 (2001).
Miyaura, N., et al.,Chemical Reviews, 95, 2457-2483 (1995).
Moss, et al.,J. Chem. Soc. Perkin Trans, 1(9), 1999-2006 (1982).
Myznikov et al.,J. Gen. Chem. USSR(Engl. Transl.), 62(6), 1125-1128 (1992).
Namkung et al.,J. Med. Chem. Soc., 8, 551-554 (1965).
Otera, J., et al.,Bull. Chem. Soc. Jpn, 54, 2964-2967 (1981).
Park, M., et al.,Tetrahedron, 42, 12707-12714 (1998).
Pei, et al.,J. Org. Chem., 67, 4924-4936 (2002).
Pei, Q., et al., “Polymer Light-Emitting Electrochemical Cells: In Situ Formation of Light-Emitting p-n Junction,”Journal of the American Chemical Society, 118, 3922-3929 (1996).
Pilgram, K., et al.,J. Heterocycl. Chem, 7, 629-633 (1970).
Prudchenko, A.T., et al.,J. Gen. Chem. USSR(Engl. Transl.), 37,2082-2084 (1967).
Ranger, M., et al.,Can. J. Chem., 76, 1571-1577, 1998.
Ranger, M., et al.,Chem. Commun., 1597-1598 (1997).
Rule et al.,J. Chem. Soc., 1096-1101 (1937).
Salbeck et al., Low Molecular Organic Glasses for Blue Electroluminescence,Synthetic Metals, 91, 209-2
Lamansky Sergey A.
Li Yingbo
Roberts Ralph R.
3M Innovative Properties Company
Dye Rena
Lown Jean A.
Thompson Camie S
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