US 11,993,617 B2
Organic luminescent material having an ancillary ligand with a partially fluorine-substituted substituent
Zhihong Dai, Beijing (CN); Yongjun Wu, Beijing (CN); Jin Qiao, Beijing (CN); Chi Yuen Raymond Kwong, 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 Oct. 15, 2020, as Appl. No. 17/071,612.
Claims priority of application No. 201910970950.X (CN), filed on Oct. 18, 2019; and application No. 201911317196.6 (CN), filed on Dec. 19, 2019.
Prior Publication US 2021/0115069 A1, Apr. 22, 2021
Int. Cl. H10K 85/30 (2023.01); C07F 3/06 (2006.01); C07F 15/00 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC C07F 3/06 (2013.01) [C07F 15/0033 (2013.01); H10K 85/342 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 21 Claims
OG exemplary drawing
 
1. A metal complex, wherein the metal complex has a structure represented by Formula M(La)u(Lb)v(Lc)w; wherein the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt; wherein La, Lb, and Lc can be optionally joined to form a multi-dentate ligand; wherein u=1 or 2, v=1 or 2, w=0 or 1, and u+v+w=3; when u=2, two La may be identical or different; when v=2, two Lb may be identical or different;
wherein La with a structure represented by Formula 1:

OG Complex Work Unit Chemistry
wherein A is, at each occurrence identically or differently, selected from O, S, Se, or NR3;
wherein x1=0, 1, 2, or 3, y1=0, 1, 2, or 3, and x1+y1=3;
wherein x2=0, 1, 2, or 3, y2=0, 1, 2, or 3, and x2+y2=3;
wherein x3=0 or 1, y3=0 or 1, and x3+y3=1;
wherein y1+y2+y3≥1;
wherein R1 and R3 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, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
and when R1 and R3 are selected from the above substituted groups, the substitution is selected from the group consisting of deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, and combinations thereof;
wherein R2 is, at each occurrence identically or differently, selected from -L-C(F)m(R)n, and 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 ring carbon atoms;
and when L is selected from the above substituted groups, the substitution is selected from the group consisting of deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, and combinations thereof;
wherein m=1 or 2, n=1 or 2, and m+n=3; when n=2, two R may be identical or different;
wherein R is, at each occurrence identically or differently, selected from the group consisting of hydrogen, deuterium, 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, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
and when R is selected from the above substituted groups, the substitution is selected from the group consisting of unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, and unsubstituted alkylsilyl having 3 to 20 carbon atoms;
wherein adjacent substituents R1 can be optionally joined to form a ring;
wherein Lb and Lc are, at each occurrence identically or differently, selected from the group consisting of structures represented by Formula 2, Formula 3, or Formula 4:

OG Complex Work Unit Chemistry
wherein Ra and Rb each represent mono-substitution, multiple-substitutions, or non-substitution;
wherein substituents Ra and Rb 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, 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof,
wherein none of adjacent substituents Ra and Rb in Formula 2, Formula 3, and Formula 4 are joined to form a ring.