US 11,952,390 B2
Phosphorescent organic metal complex and use thereof
Wei Cai, Beijing (CN); Ming Sang, Beijing (CN); Chi Yuen Raymond Kwong, Beijing (CN); Chuanjun Xia, Beijing (CN); Zhen Wang, Beijing (CN); Tao Wang, Beijing (CN); and Hongbo Li, Beijing (CN)
Assigned to Beijing Summer Sprout Technology Co., Ltd., (CN)
Filed by BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD., Beijing (CN)
Filed on Jul. 24, 2020, as Appl. No. 16/937,864.
Claims priority of application No. 202010569837.3 (CN), filed on Jun. 20, 2020.
Prior Publication US 2022/0002329 A1, Jan. 6, 2022
Int. Cl. C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01)
CPC C07F 15/0033 (2013.01) [H10K 85/342 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (2023.02)] 39 Claims
OG exemplary drawing
 
1. A metal complex, having a general formula of M(La)m(Lb)n(Lc)q, wherein
M is, at each occurrence identically or differently, selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt;
m is 1, 2, or 3, n is 0, 1, or 2, q is 0, 1, or 2, and m+n+q equals the oxidation state of the metal M; wherein when m is greater than or equal to 2, the multiple La are the same or different; when n is equal to 2, the two Lb are the same or different; when q is equal to 2, the two Lc are the same or different;
La, Lb, and Lc are a first ligand, a second ligand, and a third ligand coordinated to the metal M, respectively; La, Lb, and Lc can be optionally joined to form a multidentate ligand;
La has a structure represented by Formula 1:

OG Complex Work Unit Chemistry
wherein,
Z is selected from the group consisting of O, S, Se, NR, CRR, and SiRR, wherein when two R are present, the two R are the same or different;
X1 to X8 are, at each occurrence identically or differently, selected from C, CRx, or N;
Y1 to Y4 are, at each occurrence identically or differently, selected from CRy or N;
at least one of X1 to X8 is selected from CRx, and the Rx is cyano;
at least two of Y1 to Y4 are selected from CRy, and wherein at least one of the Ry is deuterium, and at least one of the Ry has a structure of -L-Rd;
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 combinations thereof;
Rd is, at each occurrence identically or differently, selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 ring carbon atoms, substituted heteroalkyl having 1 to 20 carbon atoms, a substituted heterocyclic group having 3 to 20 ring atoms, substituted arylalkyl having 7 to 30 carbon atoms, substituted alkoxy having 1 to 20 carbon atoms, substituted aryloxy having 6 to 30 carbon atoms, substituted alkenyl having 2 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, substituted alkylsilyl having 3 to 20 carbon atoms, substituted arylsilyl having 6 to 20 carbon atoms, substituted amino having 0 to 20 carbon atoms, or combinations thereof; the substitution in the above-mentioned group of Rd contains at least one deuterium atom;
R, Rx, and Ry 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, and
adjacent substituents R, Rx, Ry, L, and Rd can be optionally joined to form a ring; and
Lb and Lc are, at each occurrence identically or differently, selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein,
Ra, Rb, and Rc are, at each occurrence identically or differently, represent mono-substitution, multi-substitution, or non-substitution;
Xb is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NRN1, and CRC1RC2;
Xc and Xd are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NRN2;
Ra, Rb, Rc, RN1, RN2, RC1, and RC2 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; and
in structures of Lb and Lc, adjacent substituents Ra, Rb, Rc, RN1, RN2, RC1, and RC2 can be optionally joined to form a ring.