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(12) United States Patent (10) Patent No.: US 7.414,133 B2 Stössel Et Al

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(12) United States Patent (10) Patent No.: US 7.414,133 B2 Stössel Et Al USOO7414133B2 (12) United States Patent (10) Patent No.: US 7.414,133 B2 Stössel et al. (45) Date of Patent: Aug. 19, 2008 (54) PALLADIUMAND PLATINUM COMPLEXES (58) Field of Classification Search ..................... 546/2: 549/3, 206; 313/504; 257/40: 528/423; (75) Inventors: Philipp Stössel, Frankfurt (DE); Ingrid 526/265 Bach, Bad Soden (DE); Hubert See application file for complete search history. Spreitzer, Viernheim (DE) (56) References Cited (73) Assignee: Merck Patent GmbH U.S. PATENT DOCUMENTS 4,539,507 A 9/1985 VanSlyke et al. (*) Notice: Subject to any disclaimer, the term of this 5,151,629 A 9/1992 VanSlyke patent is extended or adjusted under 35 5,621,131 A 4/1997 Kreuder et al. U.S.C. 154(b) by 637 days. 5,679,760 A 10, 1997 Mullen et al. 5,763,636 A 6/1998 Kreuder et al. (21) Appl. No.: 10/534,173 6,653,438 B1 1 1/2003 Spreitzer et al. 2004/O1384.55 A1 7/2004 Stossel et al. (22) PCT Filed: Nov. 4, 2003 FOREIGN PATENT DOCUMENTS EP O 707 O2O 4f1996 (86). PCT No.: PCT/EPO3/12279 EP O 842 208 5, 1998 EP O 894 107 2, 1999 S371 (c)(1), EP 1 O28 136 8, 2000 (2), (4) Date: May 6, 2005 EP 1 191 613 3, 2002 EP 1238981 9, 2002 WO WO-92, 18552 10, 1992 (87) PCT Pub. No.: WO2004/041835 WO WO-O2, 15645 2, 2000 WO WO-OO.22026 4/2000 PCT Pub. Date: May 21, 2004 WO WO-O2/O68435 9, 2002 (65) Prior Publication Data Primary Examiner P. Nazario Gonzalez US 2006/OO712O6A1 Apr. 6, 2006 (57) ABSTRACT (30) Foreign Application Priority Data The invention relates to novel metallo-organic compounds which are phosphorescence emitters. Such compounds can be Nov. 8, 2002 (DE) ................................ 10251986 used as active components (functional materials) in a range of different applications which form part of the electronics (51) Int. Cl. industry in the broadest sense. The inventive compounds are C07F 15/00 (2006.01) described by the formulae (1), (1a), (2), (2a), (3), (4), (5), (6), HOIL 5/54 (2006.01) (7) and (8). (52) U.S. Cl. ............................... 546/2:549/3; 549/206; 313/504; 257/40: 528/423: 526/265 27 Claims, No Drawings US 7,414,133 B2 1. 2 PALLADIUMAND PLATINUM COMPLEXES typical C–C bond-forming reactions (for example Stille or Suzuki coupling), or else C-heteroatom bond-forming reac RELATED APPLICATIONS tions (for example, for C. N. Hartwig-Buchwald coupling, similarly also for C O and C P) are possible here, in order This application is a national stage application (under 35 thus either to further functionalize the halogen-functionalized U.S.C. 371) of PCT/EP2003.012279 filed Nov.4, 2003 which compounds or to use them as (co)monomers in the prepara claims benefit to German application 10251986.2 filed Nov. tion of corresponding polymers. 8, 2002. 5'-mono-, 5.5"-di-halo-functionalized mono- and bis Organometallic compounds, especially compounds of the ortho-metalated organopalladium and organoplatinum com d metals, will find use as functional components in the near 10 pounds (according to compounds (1), (1a) or (2), (2a)), 5'5"- future as active components (functional materials) in a mono- or di-halo-functionalized bis-ortho-metalated bridged series of different types of application which can be classed organopalladium and organoplatinum compounds (according within the electronics industry in the broadest sense. to compound (3) and (4)) and cationic, uncharged or anionic The organic electroluminescent devices based on organic 5'-mono-halo-functionalized mono-ortho-metalated organo components (for a general description of the construction, see 15 palladium and organoplatinum compounds (according to U.S. Pat. No. 4,539,507 and U.S. Pat. No. 5,151,629) and compound (4), (6), (7) and (8)) have not been described to their individual components, the organic light-emitting date in the literature, but their efficient preparation and avail diodes (OLEDs), have already been introduced onto the mar ability as pure materials is of great significance for various ket, as demonstrated by the car radios having organic displays electrooptical applications. from Pioneer. For the polymeric OLEDs (PLEDs) too, a first The closest prior art may be regarded as being the mono product in the form of a relatively small display (in a shaver bromination and monoiodination of a cationic ruthenium(II) from PHILIPS N.V.) has become available on the market. complex which, in addition to the ortho-metalated 2-phe Further products of this type will shortly be introduced. In nylpyridine ligand, also bears 2,2'-bipyridine ligands C. spite of this, distinct improvements are still necessary here for Coudret, S. Fraysse, J.-P-Luanay, Chem. Commun., 1998, these displays to provide real competition to the currently 25 663-664. The brominating agent used is N-bromosuccinim market-leading liquid crystal displays (LCDS) or to overtake ide, the iodinating agent a mixture of iodobenzene diacetate them. and elemental iodine in a molar ratio of one to one. The A development in this direction which has emerged in isolated yield after chromatographic purification is reported recent years is the use of organometallic complexes which as 95% in the case of bromination, and as 50% in the case of exhibit phosphorescence instead of fluorescence M. A. 30 iodination. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R. The bromination, described by Clarket al., of ortho-meta Forrest, Applied Physics Letters, 1999, 75, 4-6. lated 2-phenylduinoline and 2,3-diphenyl-quinoxaline For theoretical reasons relating to the spin probability, up ligands of ruthenium(II) carbonyl chloro and osmium(II) car to four times the energy efficiency and performance effi bonyl chloro complexes with pyridinium perbromide should ciency are possible using organometallic compounds as phos 35 also be regarded analogously. After chromatographic purifi phorescence emitters. Whether this new development will cation, yields of from 27% to 92% were obtained A. M. establish itself firstly depends strongly upon whether corre Clark, C. E. F. Rickard, W. R. Roper, L. J. Wright, J. Orga sponding device compositions can be found which can utilize nomet. Chem., 2000, 598, 262-275. these advantages (triplet emission phosphorescence com In addition, it has been shown in the application WO pared to single emission fluorescence) in OLEDs too. The 40 02/068435 that the halogenation of octahedral homo- and essential conditions for practical use are in particular a long heteroleptic rhodium and iridium complexes with an ortho operative lifetime, a high stability against thermal stress and metalated ligand set proceeds very selectively and in good to a low use and operating Voltage, in order to enable mobile very good yields. applications. In addition, there has to be efficient chemical However, this prior art described in the abovementioned access to the corresponding organometallic compounds. Of 45 references has the following disadvantages: particular interest in this context are organopalladium and (1) only the halogenation of Ru, Os, Rh and Ir complexes, but -platinum compounds. Especially taking into account the cost not that of Pd or Pt compounds, is described. of palladium and platinum, it is of crucial importance here (2) no viable teaching is provided as to how square planar, that efficient access to the corresponding derivatives is homo- and heteroleptic palladium and platinum complexes enabled. 50 with an ortho-metalated ligand set can be halogenated The present invention provides 5'-mono-, 5'5"-di-halo selectively on the coordinated ligand. Rather, it is known functionalized mono- and bis-ortho-metalated organo-palla that these complexes are readily amenable to oxidative dium and organoplatinum compounds (according to com addition by halogens (L. Chassot, E. Müller, A. Zelewsky, pounds (1), (1a) or (2), (2a)), 5'5"-mono- or di-halo Inorg. Chem. 1984, 23, 4249-4253) and thus, according to functionalized bis-ortho-metalated bridged organopalladium 55 the prior art, change from square planar to octahedral and organoplatinum compounds (according to compound (3) geometry. and (4)), and cationic, uncharged or anionic 5'-mono-halo It has now been found that, Surprisingly, the novel com functionalized mono-ortho-metalated organopalladium and pounds (1), (1a), (2), (2a), according to Scheme 2, are organoplatinum compounds (according to compound (5), (6), obtained starting from the bis-ortho-metalated organopalla (7) and (8)), which will be the central key building blocks for 60 dium or organoplatinum compounds (9), (9a), (10), (10a), and obtaining highly efficient triplet emitters, since the halogen that the novel compounds (3) or (4), according to scheme 3, function can be converted to a multitude of functions with the are obtained starting from the bis-ortho-metalated, bridged aid of common methods described in the literature. This organopalladium and organoplatinum compounds (11) or allows not only the covalent incorporation of these active, (12), and that the novel compounds (5), (6), (7) or (8), accord light-emitting centers into a multitude of polymers, but also 65 ing to scheme 4, are obtained starting from the cationic, the tailoring of the optoelectronic properties of these building uncharged or anionic functionalized mono-ortho-metalated blocks. For instance, starting from the structure mentioned, organopalladium and organoplatinum compounds (13), (14), US 7,414,133 B2 3 (15) and (16) with a halogen or interhalogen, optionally in the presence of a base and optionally of a Lewis acid, and in the -continued presence or with Subsequent addition of a reducing agentor of an organic N-halogen
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