US 12,250,871 B2
Metal complexes
Philipp Stoessel, Frankfurt am Main (DE); Falk May, Mainz (DE); Armin Auch, Darmstadt (DE); and Charlotte Walter, Darmstadt (DE)
Assigned to UDC IRELAND LIMITED, Dublin (IE)
Appl. No. 17/603,704
Filed by UDC IRELAND LIMITED, Dublin (IE)
PCT Filed Apr. 14, 2020, PCT No. PCT/EP2020/060368
§ 371(c)(1), (2) Date Oct. 14, 2021,
PCT Pub. No. WO2020/212296, PCT Pub. Date Oct. 22, 2020.
Claims priority of application No. 19169355 (EP), filed on Apr. 15, 2019.
Prior Publication US 2022/0209141 A1, Jun. 30, 2022
Int. Cl. H01L 51/00 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 85/346 (2023.02); C09K 2211/1059 (2013.01); C09K 2211/1066 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 14 Claims
 
1. A compound of formula (1)
M(L)n(L′)m  Formula (1)
containing a substructure M(L)n of the formula (2):

OG Complex Work Unit Chemistry
where the symbols and indices used are as follows:
M is iridium or platinum;
D is C or N, where one D is C and the other D is N;
X is the same or different at each instance and is CR or N;
R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R1)2, CN, NO2, OR1, SR1, COOR1, 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, 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 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and may be substituted in each case by one or more R1 radicals; optionally, two R radicals together may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
R1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, OR2, SR2, Si(R2)3, B(OR2)2, C(═O)R2, P(=O)(R2)2, S(═O)2R2, 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 each be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R2)2, C═O, NR2, O, S or CONR2 and where one or more hydrogen atoms in the alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN, 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; optionally, two or more R1 radicals together may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
R2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, in which one or more hydrogen atoms may also be replaced by F;
L′ is the same or different at each instance and is a ligand;
n is 1, 2 or 3;
m is 0, 1, 2, 3 or 4;
optionally, L and one or more of L and L′ may join together by a single bond or a bivalent or trivalent bridge, thus forming a tridentate, tetradentate, pentadentate or hexadentate ligand system.