WO2004085449A1 - Verfahren zur herstellung von hochreinen organo-iridium-verbindungen - Google Patents
Verfahren zur herstellung von hochreinen organo-iridium-verbindungen Download PDFInfo
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- WO2004085449A1 WO2004085449A1 PCT/EP2004/003087 EP2004003087W WO2004085449A1 WO 2004085449 A1 WO2004085449 A1 WO 2004085449A1 EP 2004003087 W EP2004003087 W EP 2004003087W WO 2004085449 A1 WO2004085449 A1 WO 2004085449A1
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- Prior art keywords
- formula
- iii
- iridium
- different
- occurrence
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 48
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 claims description 45
- 239000007858 starting material Substances 0.000 claims description 45
- 239000003446 ligand Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 39
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- 230000007935 neutral effect Effects 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- -1 1-keto alcoholates Chemical class 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002503 iridium Chemical class 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 3
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 3
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229960004979 fampridine Drugs 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- SINKOGOPEQSHQD-UHFFFAOYSA-N cyclopentadienide Chemical compound C=1C=C[CH-]C=1 SINKOGOPEQSHQD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 239000008204 material by function Substances 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 239000007983 Tris buffer Substances 0.000 description 15
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 3
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical group 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
- C07F15/004—Iridium compounds without a metal-carbon linkage
Definitions
- active components functional materials
- Electroluminescent devices (general description of the structure see: US 4,539,507 and US 5,151, 629) or their individual components, the organic light-emitting diodes (OLEDs) or polymer light-emitting diodes (PLEDs) has already been launched on the market, as the car radios with "organic display” from Pioneer or a razor from Philips with
- connection class Significance for the resource-saving use of the named connection class.
- Several methods for the preparation of tris-ortho-metallated organo-iridium compounds have been described in the literature.
- the general access routes, the yields achieved by these and their disadvantages are briefly outlined below on the basic body of the compound class mentioned, the fac-tris [2- (2-pyridinyl- ⁇ J) phenyl- ⁇ C] iridium (III).
- di- ⁇ -chlorotetrakis [2- (2-pyridinyl- ⁇ N) phenyl- ⁇ C] di-iridium (III), which is initially obtained in approximately 72% yield from hydrated lridium (III) chloride and 2-phenylpyridine must be prepared [p. Spouse, K.A. King, P.J. Spellane, R.J. Watts J. Am. Chem. Soc, 1984, 106, 6647], used as starting material.
- This process consisting of the reaction of iridium (III) tris (acetylacetonate) or a similar 1,3-diketo-chelate complex, with a corresponding pyridine aryl or heteroaryl compound in the presence of a dipolar protic solvent under strong Heating for a long time (> 20 h) gives very good yields (up to 96%) and also very good purities (> 99.9%).
- the description in this disclosure is very good; in the case of repeat attempts, the corresponding information could also be reproduced; however, it was noticed that the synthesis sometimes worked worse at irregular intervals or with other ligands and under certain circumstances no longer worked. The reason for this was long unclear.
- Acetylacetonate or diketonate ligands which do not have the high symmetry of the iridium (III) tris (acetylacetonate), have significantly better yields or shorter reaction times than the process according to citation 4.
- v. a. the described "inexplicable" reproducibility problems are eliminated and the yields for others
- the present invention relates to a process for the preparation of homoleptic Ir (III) complexes of the formula (I),
- CyD is a cyclic group which contains at least one donor atom, preferably nitrogen or phosphorus, via which the cyclic group is bonded to the metal and which in turn can carry one or more substituents R; the groups CyD and CyC are connected to one another via a covalent bond;
- CyC is a cyclic group which contains a carbon atom via which the cyclic group is bonded to the metal and which in turn can carry one or more substituents R;
- R 1 and R 2 are the same or different at each occurrence H or an aliphatic or aromatic hydrocarbon radical with 1 to 20 C atoms, characterized by the reaction of an iridium (III) -containing starting material which contains at least one diketonate structural unit of the formula (II ) contains,
- a homoleptic complex is understood to mean a complex compound in which only ligands of the same type are bound to a metal. The opposite would be a heteroleptic complex in which different ligands are bound to one metal.
- Preferred starting materials according to the invention according to formula (II) containing iridium (III) are characterized in that they contain a structure according to formula (V),
- R 4 , R 5 , R 6 have the meanings given under formula (II) and the iridium metal is 6-coordinate of the four oxygen atoms of the diketonate ligands and two monodentate ligands which are either anionic (X) or can be neutral (Y); n can be 0, 1 or 2.
- the monodentate ligands X and Y can be ice or trans to each other.
- Preferred iridium (III) -containing starting materials according to the invention contain a compound of the formula (V), in which X is the same or different at each occurrence a fluoride, chloride, bromide, iodide anion.
- Particularly preferred iridium (III) -containing starting materials contain a compound of the formula (XI)
- the monodentate ligands X can be ice or trans to each other.
- iridium (III) -containing starting materials which contain a structure of the formula (VI)
- R ", R °, R ° have the meanings given under formula (II) and where Z is chelatingly bonded to the iridium as a bidentate and / or bridging ligand and either a neutral ligand Z °, such as, for example, Is bipyridine, phenanthroline, ethylenediamine, propylenediamine or 2-, 3- or 4-aminopyridine, or a monoanionic bidentate ligand Z 1 , such as, for example, diketonate, carboxylate, Picolinate, aminocarboxylate or 1-keto alcoholate, or a dianionic bidentate ligand Z 2 , such as. B. oxalate, maleonate, phthalate, isophthalate, terephthalate, oxide or peroxide.
- Ligand Z instead of being chelated as in formula (VI), is bridged, so that several iridium metal atoms, which are simultaneously coordinated by two diketonate ligands, form oligomeric (o> 2) and polymer-like structures (o up to 100,000) get connected.
- G is the same or different on each occurrence either a monovalent anion X or a neutral monodentate ligand Y.
- n and p are the same or different on each occurrence 0 or 1.
- R 4 , R 5 , R 6 have the meanings given under formula (II) and the bidentate and / or bridging ligand Z, which can be neutral (Z °), monoanionic (Z 1 ) or dianionic (Z 2 ), connects two iridium metal atoms, which are already coordinated by two chelating diketonate ligands and can each be bound to a monodentate neutral or anionic ligand (G), n and p are the same or different at each occurrence 0 or 1.
- the bridging ligand Z and the monodentate ligand G can be bound to the iridium metal either ice or trans.
- iridium (III) -containing starting materials which contain structures according to formula (VI), (VII), (VIII) or (IX), characterized in that the neutral bidentate and / or bridging ligands are identical or different in Z ° each occurrence are bipyridine, phenanthroline, ethylenediamine, propylenediamine or 2-, 3- or 4-aminopyridine.
- iridium (III) -containing starting materials which contain structures according to formula (VI), (VII), (VIII) or (IX), characterized in that the monoanionic bidentate and / or bridging ligands Z 1 are identical or different with each occurrence acetylacetonate, carboxylate, such as. B. formate, acetate or propionate, picolinate, aminocarboxylate, such as. B. 2-amino acetate or 3-aminopropionate, 1-keto alcoholates, such as. B. tropolonate, benzoin, azide, cyanate, isocyanate, thiocyanate, isothiocyanate, halides, such as. B. chloride, bromide and iodide.
- iridium (III) -containing starting materials which contain structures of the formula (VI), (VII), (VIII) or (IX) in which the dianionic bidentate and / or bridging ligands Z 2 oxalate, maleonate, Phthalate, iso-
- phthalate terephthalate, oxide or peroxide.
- R 4 , R 5 , R 6 have the meanings given under formula (II) and Q is a monoanionic monodentate ligand X or a ⁇ -diketonate which is bonded to the metal via the carbon atom between the two keto carbon atoms.
- starting materials containing iridium (III) which contain structures of the formula (X), where Q is a fluoride, chloride, bromide or iodide ion.
- starting materials containing iridium (III) which contain structures of the formula (V), (VII), (VIII) and / or (IX) and in which X, each time it occurs, is identical or different to a monovalent anion, such as OH “ , F “ , CI “ , Br “ , I “ , SCN “ , CN “ , SH “ , SeH “ , N 3 “ , alcoholate, nitrate “ , carboxylate of the formula R 1 COO " , cyclopentadienide (C 5 H 5 “ ) or hydride (H “ ).
- a monovalent anion such as OH “ , F “ , CI “ , Br “ , I “ , SCN “ , CN “ , SH “ , SeH “ , N 3 “ , alcoholate, nitrate “ , carboxylate of the formula R 1 COO “ , cyclopentadienide (C 5 H 5 “ ) or hydride
- iridium (III) -containing starting materials which contain structures of the formulas (V), (VII) and / or (VIII) and in which Y is the same or different in each occurrence a neutral monodentate ligand, such as H 2 O, H 2 S, a dialkyl sulfide of the formula (R 1 ) 2 S, a dialkyl sulfoxide (R 1 ) 2 SO, NH 3 , a primary, secondary or tertiary amine, an alcohol of the formula R 1 OH, an ether of the formula (R 1 ) 2 O, a thiol of the formula R 1 SH, pyridine, quinoline, a nitrile of the formula R 1 CN, CO, a phosphine of the formula P (R 1 ) 3 , a phosphine oxide of the formula OP (R 1 ), an arsine Formula As (R 1 ) 3 or a phosphite of the formula P (OR
- lridium (III) complexes according to formula (I) can be produced, inter alia, from the lridium (III) -containing starting materials (1) to (12) shown below by way of example.
- Reaction media according to the invention are high-boiling dipolar protic solvents, such as ethylene glycol or propylene glycol, or else higher diols or polyalcohols, such as, for. B. glycerol, or polyether alcohols, such as polyethylene glycols, for example PEG600 and PEG1000, and their etherified
- Analogs such as B. triethylene glycol dimethyl ether or poly (ethylene glycol) - dimethyl ether, and NMP.
- the reaction is carried out in a temperature range from 100 ° C. to 250 ° C.
- the concentration of the iridium (III) -containing starting material is in the range from 0.05 to 1.00 molar.
- the molar ratio according to the invention of the iridium (III) -containing starting material to the ligand according to formula (IV) is 1: 4 to 1:20, a ratio of 1: 6 to 1:15 is preferred, a ratio of 1: is particularly preferred 8 to 1:12.
- the preferred concentration of the starting material of the formula (IV) is in the range from 0.50 to 10.00 molar, particularly preferably in the range from 0.80 to 2.50 molar. According to the invention, the reaction is carried out within 20 to 120 h, preferably in the range from 30 to 60 h.
- the incomplete conversion of the iridium (III) -containing starting material used can result in losses in yield and in contamination of the product with starting material containing iridium (III) or intermediate stages.
- some of the compounds of the formula (I) can only be obtained in very moderate yields and purities using a process according to the prior art.
- the process according to the invention first of all gives access to iridium (III) complexes of the formula (I).
- the present invention therefore furthermore relates to homoleptic ir (III) complexes of the formula (I)
- Example 1 (comparative example): fac-Tris [2- (2-pyridinyl- ⁇ N) phenyl- ⁇ C] iridium (III) (according to: P. St maneuverel et ai, WO 02/060910)
- Example 2 fac-T ⁇ s [2- (2-pyridinyl- ⁇ N) phenyl- ⁇ C] -iridium (III)
- the yield - with a purity of> 99.9% according to HPLC - was 5.90 - 6.13 g corresponding to 90.1 - 93.6%.
- Precipitate was washed three times with 30 ml of a mixture of ethanol and aqueous 1N hydrochloric acid (4: 1, v: v), five times with 30 ml of a mixture of ethanol and water (1: 1, v: v) and five times with 30 ml of ethanol washed and then dried under high vacuum for 5 h at 80 ° C and 2 h at 200 ° C.
- the yield - with a purity of> 99.0% according to HPLC - was 3.24 - 3.45 g corresponding to 40.3 - 42.8%.
- the yield - with a purity of> 37.4% according to HPLC - was 4.30 -.4.56 g corresponding to 52.2 - 55.4%.
- Example 6 fac-tris [2- (2-pyridinyl- ⁇ N) benzo [b] thien-3-yl- ⁇ C] - iridium (III)
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Abstract
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020057018134A KR101086657B1 (ko) | 2003-03-27 | 2004-03-24 | 고순도 유기이리듐 화합물의 제조 방법 |
JP2006504827A JP4680889B2 (ja) | 2003-03-27 | 2004-03-24 | 高純度の有機イリジウム化合物を生成するための方法 |
US10/550,976 US7482450B2 (en) | 2003-03-27 | 2004-03-24 | Method for producing high-purity organoiridium compounds |
DE502004005504T DE502004005504D1 (de) | 2003-03-27 | 2004-03-24 | Verfahren zur herstellung von hochreinen organo-iridium-verbindungen |
EP04722811A EP1611146B1 (de) | 2003-03-27 | 2004-03-24 | Verfahren zur herstellung von hochreinen organo-iridium-verbindungen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10314102.2 | 2003-03-27 | ||
DE10314102A DE10314102A1 (de) | 2003-03-27 | 2003-03-27 | Verfahren zur Herstellung von hochreinen Organo-Iridium-Verbindungen |
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WO2004085449A1 true WO2004085449A1 (de) | 2004-10-07 |
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Family Applications (1)
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PCT/EP2004/003087 WO2004085449A1 (de) | 2003-03-27 | 2004-03-24 | Verfahren zur herstellung von hochreinen organo-iridium-verbindungen |
Country Status (7)
Country | Link |
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US (1) | US7482450B2 (de) |
EP (1) | EP1611146B1 (de) |
JP (1) | JP4680889B2 (de) |
KR (1) | KR101086657B1 (de) |
CN (1) | CN100439380C (de) |
DE (2) | DE10314102A1 (de) |
WO (1) | WO2004085449A1 (de) |
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Also Published As
Publication number | Publication date |
---|---|
CN1764669A (zh) | 2006-04-26 |
JP4680889B2 (ja) | 2011-05-11 |
EP1611146A1 (de) | 2006-01-04 |
JP2006521324A (ja) | 2006-09-21 |
DE10314102A1 (de) | 2004-10-14 |
DE502004005504D1 (de) | 2007-12-27 |
KR101086657B1 (ko) | 2011-11-24 |
EP1611146B1 (de) | 2007-11-14 |
US20060142604A1 (en) | 2006-06-29 |
KR20050123123A (ko) | 2005-12-29 |
US7482450B2 (en) | 2009-01-27 |
CN100439380C (zh) | 2008-12-03 |
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