US 12,457,893 B2
Organic electroluminescent device
Chi Yuen Raymond Kwong, Beijing (CN); Jianfei Yao, Beijing (CN); Zhen Wang, Beijing (CN); Feng Li, Beijing (CN); Yang Wang, Beijing (CN); Junfei Wang, Beijing (CN); Gang Yang, Beijing (CN); Hongbo Li, Beijing (CN); Ming Sang, Beijing (CN); Wei Cai, Beijing (CN); and Chuanjun Xia, Beijing (CN)
Assigned to BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD., Beijing (CN)
Filed by BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD., Beijing (CN)
Filed on Dec. 10, 2021, as Appl. No. 17/547,737.
Claims priority of application No. 202011438482.0 (CN), filed on Dec. 11, 2020; and application No. 202111221350.7 (CN), filed on Oct. 27, 2021.
Prior Publication US 2022/0199916 A1, Jun. 23, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/30 (2023.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C09K 11/06 (2013.01); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1033 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 42 Claims
 
1. An organic electroluminescent device, comprising:
an anode,
a cathode, and
an organic layer disposed between the anode and the cathode, wherein the organic layer at least comprises a first metal complex and a first compound;
wherein the first metal complex contains a metal M and a ligand La coordinated to the metal M, wherein the ligand La has a structure represented by Formula 1:

OG Complex Work Unit Chemistry
wherein
the metal M is selected from a metal with a relative atomic mass greater than 40;
Cy is, at each occurrence identically or differently, selected from substituted or unsubstituted aryl having 5 to 24 ring atoms or substituted or unsubstituted heteroaryl having 5 to 24 ring atoms; and the Cy is joined to the metal M by a metal-carbon bond or a metal-nitrogen bond;
X is, at each occurrence identically or differently, selected from the group consisting of O, S, Se, NR1, CR1R1 and SiR1R1; when two R1 are present at the same time, the two R1 are identical or different;
X1 to X8 are, at each occurrence identically or differently, selected from C, CRx or N, and at least one of X1 to X4 is C and joined to the Cy;
X1, X2, X3 or X4 is joined to the metal M by a metal-carbon bond or a metal-nitrogen bond;
Rx and R1 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;
at least one of X1 to X8 is CRx, and the Rx is cyano or fluorine;
adjacent substituents R1, and/or Rx can be optionally joined to form a ring;
wherein the first compound has a structure represented by Formula 2:

OG Complex Work Unit Chemistry
wherein
Ar1 has a structure represented by Formula A:

OG Complex Work Unit Chemistry
wherein
Z is, at each occurrence identically or differently, selected from the group consisting of O, S and Se;
L is, at each occurrence identically or differently, selected from a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted arylene having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms or a combination thereof;
Z1 to Z8 are, at each occurrence identically or differently, selected from C, CRz or N, and at least one of Z1 to Z8 is C and joined to the L;
Rz is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;
at least one, at least two or at least three of Z1 to Z8 are selected from CRz, and the Rz is selected from substituted or unsubstituted aryl having 6 to 30 carbon atom;
Ar2 and Ar3 are, at each occurrence identically or differently, selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms or a combination thereof;
“*” represents a position where Formula A is joined to Formula 2; and
adjacent substituents Rz can be optionally joined to form a ring.