US 11,659,763 B2
Metal complexes
Philipp Stoessel, Frankfurt am Main (DE); and Armin Auch, Darmstadt (DE)
Assigned to Merck Patent GmbH
Appl. No. 16/771,537
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Dec. 10, 2018, PCT No. PCT/EP2018/084094
§ 371(c)(1), (2) Date Jun. 10, 2020,
PCT Pub. No. WO2019/115423, PCT Pub. Date Jun. 20, 2019.
Claims priority of application No. 17206950 (EP), filed on Dec. 13, 2017.
Prior Publication US 2021/0175441 A1, Jun. 10, 2021
Int. Cl. H10K 85/30 (2023.01); H01L 51/00 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H01L 51/50 (2006.01)
CPC H01L 51/0085 (2013.01) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H01L 51/5016 (2013.01)] 17 Claims
 
1. Compound of the formula (1)

OG Complex Work Unit Chemistry
where the symbols used are as follows:
L1 is a sub-ligand of the formula (2) which coordinates to the iridium via the two nitrogen atoms identified by * and which is bonded to V via the dotted bond,

OG Complex Work Unit Chemistry
where:
A is the same or different at each instance and is CR or N, where not more than one A group per ring is N;
RB is the same or different at each instance and is F, OR1, a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl group in each case may be substituted by one or more R1 radicals, or an aromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted in each case by one or more R1 radicals; at the same time, the two RB radicals together may also form a ring system;
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 may be the same as or different from L1;
V is a group of the formula (3), where the dotted bonds each represent the bonds to the sub-ligands L1, L2 and L3,

OG Complex Work Unit Chemistry
X1 is the same or different at each instance and is CR or N;
X2 is the same or different at each instance and is CR or N, or two adjacent X2 groups together are NR, O or S, thus forming 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, thus forming a five-membered ring; with the proviso that not more than two adjacent X2 groups in each ring are N;
X3 is C at each instance in one cycle or one X3 group is N and the other X3 group in the same cycle is C, where the X3 groups in the three cycles may be 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 at 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, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals and where one or more nonadjacent CH2 groups may be 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 may be substituted in each case by one or more R1 radicals; at the same time, two R radicals together may also form a ring system;
R1 is the same or different at 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, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R2 radicals and where one or more nonadjacent CH2 groups may be 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 may be substituted in each case by one or more R2 radicals; at the same time, two or more R1 radicals together may form a ring system;
R2 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
at the same time, the three bidentate ligands L1, L2 and L3, apart from by the V group, may also be closed by a further bridge to form a cryptate.