US 12,441,750 B2
Organic metal complex, organic light-emitting device including the same, display apparatus, imaging apparatus, electronic apparatus, illumination apparatus, and moving object
Tomokazu Tsuji, Fukui (JP); Kenji Yamada, Kanagawa (JP); Akira Tsuboyama, Tokyo (JP); and Yuto Ito, Tokyo (JP)
Assigned to Canon Kabushiki Kaisha, Tokyo (JP)
Filed by CANON KABUSHIKI KAISHA, Tokyo (JP)
Filed on Mar. 11, 2022, as Appl. No. 17/692,904.
Claims priority of application No. 2021-043285 (JP), filed on Mar. 17, 2021.
Prior Publication US 2022/0306666 A1, Sep. 29, 2022
Int. Cl. H01L 51/50 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 50/84 (2023.01); H10K 59/80 (2023.01); H10K 101/10 (2023.01)
CPC C07F 15/0033 (2013.01) [H10K 85/342 (2023.02); H10K 50/11 (2023.02); H10K 50/841 (2023.02); H10K 59/871 (2023.02); H10K 2101/10 (2023.02)] 21 Claims
OG exemplary drawing
 
1. An organic metal complex represented by formula (1):
MLmL′nL″1  (1)
where in formula (1), M represents a transition metal, and Lm, L′n, and L″l represent ligands different from each other; m is an integer of 1 to 3, n is an integer of 0 to 2, 1 is an integer of 0 to 2, and m+n+l=3; and MLm is a structure represented by formula (2):

OG Complex Work Unit Chemistry
where in formula (2), R11 to R14 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted amino group, a silyl group, and a cyano group;
X is selected from the group consisting of CRR′, SiRR′, S, SO, and SO2; R and R′ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a halogen atom;
Y1 to Y6 are each independently selected from the group consisting of a carbon atom and a nitrogen atom;
when Y1 to Y6 are carbon atoms, the carbon atoms may each be substituted with an alkyl group or an aryl group;
when Y3 to Y6 are carbon atoms, each of the carbon atoms may be bound to a carbon atom adjacent to the carbon atom to form a ring structure; and
ML′n and ML″l are each independently selected from the group consisting of formulae (4) and (5):

OG Complex Work Unit Chemistry
where in formulae (4) and (5), R31 to R38 and R41 to R43 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aralkyl group, a substituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.