US 11,839,140 B2
Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDS
Oliver Molt, Weinheim (DE); Nicolle Langer, Heppenheim (DE); Evelyn Fuchs, Mannheim (DE); Korinna Dormann, Bad Duerkheim (DE); Christian Schildknecht, Mannheim (DE); Soichi Watanabe, Mannheim (DE); Gerhard Wagenblast, Wachenheim (DE); Christian Lennartz, Schifferstadt (DE); Thomas Schaefer, Liestal (CH); Heinz Wolleb, Fehren (CH); Teresa Marina Figueira Duarte, Mainz (DE); Stefan Metz, Mannheim (DE); and Peter Murer, Oberwil (CH)
Assigned to UDC IRELAND LIMITED, Dublin (IE)
Filed by UDC IRELAND LIMITED, Dublin (IE)
Filed on Aug. 31, 2022, as Appl. No. 17/823,523.
Application 17/823,523 is a continuation of application No. 17/132,829, filed on Dec. 23, 2020, granted, now 11,444,254.
Application 17/132,829 is a continuation of application No. 16/054,011, filed on Aug. 3, 2018, granted, now 10,916,716.
Application 16/054,011 is a continuation of application No. 15/288,057, filed on Oct. 7, 2016, granted, now 10,090,476.
Application 15/288,057 is a continuation of application No. 13/516,117, granted, now 9,487,548, previously published as PCT/EP2010/069541, filed on Dec. 13, 2010.
Claims priority of provisional application 61/391,712, filed on Oct. 11, 2010.
Claims priority of provisional application 61/323,885, filed on Apr. 14, 2010.
Claims priority of provisional application 61/286,046, filed on Dec. 14, 2009.
Claims priority of application No. 10187176 (EP), filed on Oct. 11, 2010.
Prior Publication US 2023/0026258 A1, Jan. 26, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 405/14 (2006.01); C07D 307/91 (2006.01); C07F 7/08 (2006.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/14 (2023.01); H10K 50/16 (2023.01); H10K 50/18 (2023.01); H10K 50/125 (2023.01); H10K 50/155 (2023.01); H10K 50/165 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07D 307/91 (2013.01); C07D 405/14 (2013.01); C07F 7/0816 (2013.01); C07F 15/0033 (2013.01); C07F 15/0086 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/30 (2023.02); H10K 85/346 (2023.02); H10K 85/40 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1059 (2013.01); C09K 2211/1088 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/125 (2023.02); H10K 50/14 (2023.02); H10K 50/155 (2023.02); H10K 50/16 (2023.02); H10K 50/165 (2023.02); H10K 50/18 (2023.02); H10K 85/653 (2023.02); H10K 2101/10 (2023.02); Y02E 10/549 (2013.01)] 20 Claims
 
1. A metal-carbene complex of the general formula (I):

OG Complex Work Unit Chemistry
wherein:
M is Ir or Pt,
n is an integer selected from 1, 2 and 3,
Y is NR1, O, S or C(R10)2,
A2, A3, A4, A5 are each independently N or C, where 2 A=nitrogen atoms and at least one carbon atom is present between two nitrogen atoms in the ring,
R1 is a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 carbon atoms and/or heteroatoms,
R2, R3, R4, R5 are each, if A2, A3, A4 and/or A5 is N, a free electron pair, or, if A2, A3, A4 and/or A5 is C, each independently hydrogen, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 carbon atoms and/or heteroatoms, group with donor or acceptor action,
R6, R7, R8, R9 are each independently hydrogen, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 carbon atoms and/or heteroatoms, group with donor or acceptor action,
or
R6 and R7, R7 and R8 or R8 and R9, together with the carbon atoms to which they are bonded, form a saturated, unsaturated or aromatic, optionally substituted ring optionally interrupted by at least one heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms,
and/or
if A5 is C, R5 and R6 together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, an aromatic unit, heteroaromatic unit and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which is optionally fused a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms,
R10 is independently a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 carbon atoms and/or heteroatoms,
K is an uncharged mono- or bidentate ligand,
L is a mono- or dianionic ligand,
m is 0, 1 or 2, where, when m is 2, the K ligands may be the same or different, and
o is 0, 1 or 2, where, when o is 2, the L ligands may be the same or different.