US 7,482,450 B2
Method for producing high-purity organoiridium compounds
Ingrid Bach, Bad Soden (Germany); Philipp Stössel, Frankfurt (Germany); and Hubert Spreitzer, Viernheim (Germany)
Assigned to Merck Patent GmbH, (Germany)
Appl. No. 10/550,976
PCT Filed Mar. 24, 2004, PCT No. PCT/EP2004/003087
§ 371(c)(1), (2), (4) Date Sep. 26, 2005,
PCT Pub. No. WO2004/085449, PCT Pub. Date Oct. 07, 2004.
Claims priority of application No. 103 14 102 (DE), filed on Mar. 27, 2003.
Prior Publication US 2006/0142604 A1, Jun. 29, 2006
Int. Cl. C07F 15/00 (2006.01)
U.S. Cl. 546—2  [556/146] 18 Claims
 
1. A process for preparing homoleptic Ir(III) complexes of the formula (I)

OG Complex Work Unit Drawing
in which:
CyD is a cyclic group which contains at least one donor atom via which the cyclic group is bonded to the metal and which may in turn bear one or more substituents R; the CyD and CyC groups are joined together 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 may in turn bear one or more substituents R;
R is the same or different at each instance and is H, F, Cl, Br, I, NO2, CN, a straight-chain or branched or cyclic alkyl or alkoxy group having from 1 to 20 carbon atoms, in which one or more nonadjacent CH2 groups may be replaced by —O—, —S—, —NR1—, —CONR2—, —CO—O—, —CR1═CR1— or —C≡C—, and in which one or more hydrogen atoms may be replaced by F, or an aryl or heteroaryl group which has from 4 to 14 carbon atoms and may be substituted by one or more nonaromatic R radicals; where a plurality of substituents R, both on the same ring and on the two different rings, together may in turn form a further mono- or polycyclic, aliphatic or aromatic ring system;
R1 and R2 are the same or different at each instance and are H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms,
characterized by the reaction of an iridium(III)-containing reactant which contains at least one diketonate structural unit of the formula (II)

OG Complex Work Unit Drawing
in which:
R4, R6 are the same or different at each instance and are a linear, branched or cyclic alkyl group having 1-20 carbon atoms, in which one or more nonadjacent CH2 groups may be replaced by —O—, —S—, —NR1—, —CONR2—, —CO—O—, —CR1═CR1— or —C≡C—, and in which one or more hydrogen atoms may be replaced by F or aromatic groups each having from 3 to 14 carbon atoms, or an aryl and/or heteroaryl group having 3-20 carbon atoms or an alkoxy group OR1,
R5 is the same or different at each instance and is a linear, branched or cyclic alkyl group having 1-20 carbon atoms, in which one or more nonadjacent CH2 groups may be replaced by —O—, —S—, —NR1—, —CONR2—, —CO—O—, —CR1═CR1— or —C≡C—, and in which one or more hydrogen atoms may be replaced by F or aromatic groups each having from 3 to 14 carbon atoms, or an aryl and/or heteroaryl group having 3-20 carbon atoms,
R1 and R2 are the same or different at each instance and are H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms,
excluding homoleptic diketonate complexes of the formula (II) and compounds of the formula (II) which contain two ligands of the formula (III)

OG Complex Work Unit Drawing
where the symbols CyC and CyD in formula (III) are each as defined under formula (I),with a compound of the formula (IV)

OG Complex Work Unit Drawing
in which the symbols CyD and CyC are each as defined under formula (I).