US 11,871,654 B2
Heteroleptic carbene complexes and the use thereof in organic electronics
Evelyn Fuchs, Mannheim (DE); Oliver Molt, Weinheim (DE); Korinna Dormann, Bad Duerkheim (DE); Thomas Gessner, Heidelberg (DE); Nicolle Langer, Heppenheim (DE); Ingo Muenster, Boehl-Iggelheim (DE); JianQiang Qu, Shanghai (CN); Christian Lennartz, Schifferstadt (DE); Christian Schildknecht, Mannheim (DE); Soichi Watanabe, Mannheim (DE); Gerhard Wagenblast, Wachenheim (DE); Guenter Schmid, Hemhofen (DE); Herbert Friedrich Boerner, Aachen (DE); and Volker van Elsbergen, Aachen (DE)
Assigned to UDC IRELAND LIMITED, Dublin (IE)
Filed by BASF SE, Ludwigshafen (DE); OLEDWORKS GMBH, Aachen (DE); and OSRAM OLEO GMBH, Regensburg (DE)
Filed on Nov. 15, 2021, as Appl. No. 17/526,503.
Application 17/526,503 is a continuation of application No. 16/294,403, filed on Mar. 6, 2019, granted, now 11,189,806.
Application 16/294,403 is a continuation of application No. 13/504,725, abandoned, previously published as PCT/EP2010/066400, filed on Oct. 28, 2010.
Claims priority of provisional application 61/255,499, filed on Oct. 28, 2009.
Prior Publication US 2022/0144869 A1, May 12, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/50 (2006.01); H10K 85/30 (2023.01); C07F 15/00 (2006.01); H10K 50/11 (2023.01); H10K 50/14 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C07F 15/0086 (2013.01); H10K 85/361 (2023.02); H10K 50/11 (2023.02); H10K 50/14 (2023.02); H10K 85/40 (2023.02); H10K 85/6572 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A heteroleptic complex of the general formula (I)

OG Complex Work Unit Chemistry
wherein:
M is a metal atom selected from the group consisting of Ir and Pt,
A1, A2 are each independently N or C,
n, m are each independently 1 or 2, where, if M is Pt, the sum of n and m is 2, or, if M is Ir, the sum of n and m is 3,
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 5 to 18 carbon atoms and/or heteroatoms,
R2, R3 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, 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 5 to 18 carbon atoms and/or heteroatoms,
R4, R5, R6, R7 are each independently hydrogen, substituent with donor or acceptor action, 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 5 to 18 carbon atoms and/or heteroatoms,
or
R4 and R5 or R5 and R6 and/or R6 and R7 together form a saturated, unsaturated or aromatic carbon ring optionally interrupted by at least one heteroatom and having a total of 5 to 30 carbon atoms or heteroatoms,
R8, R9 are each independently a free electron pair if A1 or A2 is N, or, if A1 or A2 is C, 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 5 to 18 carbon atoms and/or heteroatoms,
R10 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 5 to 18 carbon atoms and/or heteroatoms,
R11, R12, R13, R14 are each independently hydrogen, substituent with donor or acceptor action, 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 5 to 18 carbon atoms and/or heteroatoms,
or
R11 and R12 or R12 and R13 and/or R14 together form a saturated, unsaturated or aromatic carbon ring optionally interrupted by at least one heteroatom and having a total of 5 to 30 carbon atoms and/or heteroatoms,
R1 and R14 optionally together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which a substituted or unsubstituted, five-to eight-membered ring comprising carbon atoms and/or heteroatoms is optionally fused,
if A1 is C, R7 and R8 optionally together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms is optionally fused.