Carbene containing metal complexes as OLEDs

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C556S136000, C546S004000, C313S504000

Reexamination Certificate

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07956192

ABSTRACT:
A process for preparing a compound having the formula L2IrL′ is provided. The process comprises:combiningand L′ in the presence of an organic solvent to form a mixture, wherein L is a suitable carbene ligand precursor coordinated to Ir; and L′ is a bidentate ligand or two monodentate ligands, and L is different from L′;Also provided is a process for preparing a compound having the formulaThe process comprises:(a) combining L, a carbene ligand precursor, with an organic solvent;(b) maintaining the mixture of step (a) at a temperature from about 175° C. to less than the boiling point of the organic solvent in (a).A process for preparing a compound with the formula L3Ir is also provided. This process comprises combiningand L in the presence of alcohol and a base to form a mixture, wherein L is a bidentate ligand that may form a five-membered chelate ring.

REFERENCES:
patent: 4769292 (1988-09-01), Tang et al.
patent: 5247190 (1993-09-01), Friend et al.
patent: 5703436 (1997-12-01), Forrest et al.
patent: 5707745 (1998-01-01), Forrest et al.
patent: 5834893 (1998-11-01), Bulovic et al.
patent: 5844363 (1998-12-01), Gu et al.
patent: 6013982 (2000-01-01), Thompson et al.
patent: 6087196 (2000-07-01), Sturm et al.
patent: 6091195 (2000-07-01), Forrest et al.
patent: 6097147 (2000-08-01), Baldo et al.
patent: 6160267 (2000-12-01), Kunugi et al.
patent: 6294398 (2001-09-01), Kim et al.
patent: 6303238 (2001-10-01), Thompson et al.
patent: 6310360 (2001-10-01), Forrest et al.
patent: 6337102 (2002-01-01), Forrest et al.
patent: 6383666 (2002-05-01), Kim et al.
patent: 6420057 (2002-07-01), Ueda et al.
patent: 6458475 (2002-10-01), Adachi
patent: 6468819 (2002-10-01), Kim et al.
patent: 6548956 (2003-04-01), Forrest et al.
patent: 6576134 (2003-06-01), Agner
patent: 6602540 (2003-08-01), Gu et al.
patent: 7431968 (2008-10-01), Shtein et al.
patent: 2001/0015432 (2001-08-01), Igarashi
patent: 2001/0019782 (2001-09-01), Igarashi et al.
patent: 2002/0024293 (2002-02-01), Igarashi et al.
patent: 2002/0034656 (2002-03-01), Thompson et al.
patent: 2002/0048689 (2002-04-01), Igarashi et al.
patent: 2002/0063516 (2002-05-01), Tsuboyama et al.
patent: 2002/0064681 (2002-05-01), Takiguchi et al.
patent: 2002/0071963 (2002-06-01), Fujii
patent: 2002/0121638 (2002-09-01), Grushin et al.
patent: 2002/0182441 (2002-12-01), Lamansky et al.
patent: 2002/0190250 (2002-12-01), Grushin et al.
patent: 2003/0068526 (2003-04-01), Kamatani et al.
patent: 2003/0068536 (2003-04-01), Tsuboyama et al.
patent: 2003/0072964 (2003-04-01), Kwong et al.
patent: 2003/0091862 (2003-05-01), Tokito et al.
patent: 2003/0096138 (2003-05-01), Lecloux et al.
patent: 2003/0141809 (2003-07-01), Furugori et al.
patent: 2003/0162299 (2003-08-01), Hsieh et al.
patent: 2003/0230980 (2003-12-01), Forrest et al.
patent: 2004/0075096 (2004-04-01), Grushin et al.
patent: 2004/0174116 (2004-09-01), Lu et al.
patent: 2004/0209116 (2004-10-01), Ren et al.
patent: 2005/0170206 (2005-08-01), Ma et al.
patent: 2005/0230665 (2005-10-01), Thompson
patent: 2005/0260448 (2005-11-01), Lin et al.
patent: 2006/0258043 (2006-11-01), Bold
patent: 2008/0018221 (2008-01-01), Egen et al.
patent: 2008/0200686 (2008-08-01), Molt et al.
patent: 1 191 613 (2002-03-01), None
patent: 1 191 614 (2002-03-01), None
patent: 1 239 526 (2002-09-01), None
patent: WO 92/02714 (1992-02-01), None
patent: WO 02/02714 (2002-01-01), None
patent: WO 02/15645 (2002-02-01), None
patent: WO 02/074015 (2002-09-01), None
patent: WO 03/084972 (2003-10-01), None
patent: WO 03/088271 (2003-10-01), None
patent: WO 03/099959 (2003-12-01), None
Tamayo et al., Journal of American Chemical Society, vol. 125, No. 24, pp. 7377-7387 (Published on the Web May 22, 2003).
Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, pp. 151-154 (1998).
Baldo et al., “Very High-Efficiency Green Organic Light-Emitting Devices Based on Electrophosphorescence,” Appl. Phys. Lett., vol. 75, No. 3, pp. 4-6 (1999).
Adachi et al., “Nearly 100% Internal Phosphorescent Efficiency in an Organic Light Emitting Device,” J. Appl. Phys., vol. 90, pp. 5048-05051 (2001).
“Inorganic Chemistry” (2ndEdition) by Gary L. Miessler and Donald A. Tarr, Prentice Hall, pp. 1-3, 422-424, 442, Aug. 1999 version.
Thomas H. Lowry et al., “Mechanism and Theory in Organic Chemistry,” Harper & Row Publishers, New York, p. 256 (1976).
Nicholas J. Turro, Modern Molecular Photochemistry, University Science Books, Sausalito, California, pp. 109-110, (Apr. 1991).
Nemcsok et al., “The Significance of π Interactions in Group 11 Complexes with N-Heterocyclic Carbenes”, Organometallics, vol. 23, pp. 3640-3646, 2004.
Koizumi et al., “Terpyridine-Analogous (N,N,C)-Tridentate Ligands: Synthesis, Structures, and Electrochemical Properties of Ruthenium (II) Complexes Bearing Gtridentate Pyridinium and Pyridinylidene Ligands,” Organometallics, vol. 22, pp. 970-975 (2003).
Bourissou et al., “Stable Carbenes,” Chem Rev. vol. 100, pp. 39-91 (2000).
Ashekenazi et al., “Discovery of the First Metallaquinone,” J. Am. Chem. Soc., vol. 122, pp. 8797-8798 (2000).
Cattoën, et al., “Amino-Aryl-Carbenes: Alternative Ligands for Transition Metals?” J. Am. Chem. Soc., vol. 126, pp. 1342-1343 (2004).
Wong et al., “Ruthenium (II) o-Acetylide and Carbene Complexes Supported by the Terpyridine-Bipyridine Ligand Set: Structural, Spectroscopic, and Photochemical Studies,” Organometallics, vol. 23, pp. 2263-2272 (2004).
Klapars et al., “A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycles,” J. Am. Chem. Soc., vol. 123, pp. 7727-7729 (2001).
Lai et al., “Carbene andf Isocyanide Ligation at Luminescent Cyclometalated 6-Phenyl-2,2′-bipyridyl Platinum (II) Complexes: Structural and Spectroscopic Studies,” Organometallics, vol. 18, pp. 3327-3336 (1999).
Xue et al., “Spectroscopic and Excited-State Properties of Luminescent Rhenium (I) N-Heterocyclic Carbene Complexes Containing Aromatic Diimine Ligands,” Organometallics, vol. 17, pp. 1622-1630 (1998).
Wang et al., “Facile Synthesis of Silver (I)-Carbene Complexes. Useful Carbene Transfer Agents,” Organometallics, vol. 17, pp. 972-975 (1998).
Cardin et al., “Transition Metal-Carbene Complexes,” Chem. Rev., vol. 72, pp. 545-574 (1972).
Kunkley et al., “Optical Properties of Transition Metal Complexes with N-Heterocyclic Carbenes as Ligands. 1,3-di-t-Butylimidazol-2-ylidene as Charge Transfer Donor and Acceptor,” J. Organometallic Chem., vol. 684, pp. 113-116 (2003).
Anthony R. Chianese et al., “Abnormal C5-Bound N-Heterocyclic Carbenes: Extremely Strong Electron Donor Ligands and Their Iridium (I) and Iridium (III) Complexes,” Organometallics, vol. 23, pp. 2461-2468 (2004).
Xile Hu et al., “Group 11 Metal Complexes of N-Heterocyclic Carbene Ligands: Nature of the Metal-Carbene Bone,” Organometallics, vol. 23, pp. 755-764 (2004).
Xile Hu et al., “A Bis-Carbenealkenyl Copper(I) Complex from a Tripodal Tris-Carbene Ligand,” Organometallics, vol. 22, pp. 3016-3018 (2003).
Siu-Wai Lai et al., “[{Pt(CN)(C10H21N4)}6]: A Luminescent Hexanuclear Platinum (II) Macrocycle Containing Chelating Dicarbene and Bridging Cyanide Ligands,” Angnew. Chem. Int. Ed., vol. 37, No. 1/2, pp. 182-184 (1998).
Xile Hu et al., “Silver Complexes of a Novel Tripodal N-Heterocyclic Carbene Ligand: Evidence for Significant Metal-Carbene π-Interaction,” Organometallics, vol. 22, pp. 612-614 (2003).
James P. Collman et al., “Principles and Applications of Organotransition Metal Chemistry,” University Science Books, Mill Valley, CA, pp. 119-121(1987).
Nicholas A. Piro, et al., “Pyridinium-derived N-heterocyclic carbene ligands: syntheses, structures an

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