US 12,075,692 B2
Iridium complex-containing composition, organic light emitting device having the same, display apparatus, imaging apparatus, electronic equipment, lighting apparatus, and moving body
Yutaka Tani, Kanagawa (JP); Katsuyuki Hotta, Kanagawa (JP); and Kentaro Ito, Tokyo (JP)
Assigned to Canon Kabushiki Kaisha, Tokyo (JP)
Filed by CANON KABUSHIKI KAISHA, Tokyo (JP)
Filed on Apr. 7, 2021, as Appl. No. 17/224,565.
Claims priority of application No. 2020-085564 (JP), filed on May 15, 2020.
Prior Publication US 2021/0359225 A1, Nov. 18, 2021
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A composition comprising:
a homo-N-trans (HNT) iridium complex having an iridium atom, and a first ligand, a second ligand, and a third ligand that are bonded to the iridium atom,
the second ligand having the same structure as the first ligand,
the third ligand having a different structure from the first and second ligands; and
an isomer of the iridium complex, the isomer having an iridium atom, a fourth ligand, a fifth ligand, and the third ligand,
the fourth ligand being a ligand represented by the same condensed formula as that of the first ligand, and
the fifth ligand being a ligand represented by the same condensed formula as that of the second ligand,
wherein a composition ratio of the isomer relative to a total of the iridium complex and the isomer is 1.5% or more, and
wherein the iridium complex is an iridium complex represented by formula [1] or [2] below:

OG Complex Work Unit Chemistry
where, in formula [1] and formula [2], L represents a bidentate ligand, R1 to R18 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heteroaromatic group;
ring A represents a ring structure that may have a substituent and that is selected from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a 9,9-spirobifluorene ring, a chrysene ring, and a substituted or unsubstituted heteroaromatic group; and
IrL is represented by one of formulae [3] to [5] below:

OG Complex Work Unit Chemistry
where, in formulae [3] to [5], R19 to R33 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heteroaromatic group.