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US 11,535,640 B2Granted
Metal complexes
AssigneeMerck Patent GmbH
InventorsPhilipp Stoessel, Armin Auch
Life of this patent
Estimating the term…
Abstract
The present invention relates to iridium complexes suitable for use in organic electroluminescent devices, especially as emitters.
Claims17
A compound of formula (1):
- wherein
- L1 is a sub-ligand of formula (2):
- which coordinates to the iridium via the two Z groups and which is bonded to V via the dotted bond;
- A is the same or different in each instance and is CR2, O, S, or NR, wherein at least one A group is CR2;
- Z is the same or different in each instance and is O, S, or NR;
- L2 is a bidentate, monoanionic sub-ligand which coordinates to the iridium via one carbon atom and one nitrogen atom or via two carbon atoms;
- L3 is a bidentate, monoanionic sub-ligand which coordinates to the iridium via one carbon atom and one nitrogen atom or via two carbon atoms, or is a sub-ligand of the formula (2) which is optionally the same as or different from L1;
- V is a group of formula (3), wherein the dotted bonds each denote the linkage of sub-ligands L1, L2 and L3,
- X1 is the same or different in each instance and is CR or N;
- X2 is the same or different in each instance and is CR or N, or two adjacent X2 groups together are NR, O, or S, so as to define a five-membered ring;
- or two adjacent X2 groups together are CR or N when one of the X3 groups in the cycle is N, so as to form a five-membered ring;
- with the proviso that not more than two adjacent X2 groups in each ring are N;
- X3 is C in each instance in one cycle or one X3 group is N and the other X3 group in the same cycle is C, wherein the X3 groups in the three cycles are optionally selected independently, with the proviso that two adjacent X2 groups together are CR or N when one of the X3 groups in the cycle is N;
- R is the same or different in each instance and is H, D, F, Cl, Br, I, N(R1)2, OR1, SR1, CN, NO2, COOH, C(═O)N(R1)2, Si(R1)3, B(OR1)2, C(═O)R1, P(═O)(R1)2, S(═O)R1, S(═O)2R1, OSO2R1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group in each case is optionally substituted by one or more R1 radicals and wherein one or more nonadjacent CH2 groups are optionally replaced by Si(R1)2, C═O, NR1, O, S, or CONR1, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R1 radicals;
- and wherein two R radicals together optionally define a ring system;
- R1 is the same or different in each instance and is H, D, F, Cl, Br, I, N(R2)2, OR2, SR2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group in each case are optionally substituted by one or more R2 radicals, wherein one or more nonadjacent CH2 groups are optionally replaced by Si(R2)2, C═O, NR2, O, S, or CONR2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R2 radicals;
- and wherein two or more R1 radicals together optionally define a ring system;
- R2 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, and/or heteroaromatic organic radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms is optionally replaced by F;
- and
- wherein the three bidentate ligands L1, L2, and L3, in addition to bridge V, are also optionally connected via a further bridge so as to form a cryptate.
17 more elements
Dependencies are inferred from the claim text.