US 12,421,261 B2
Organic light emitting material
Qi Zhang, Beijing (CN); Xueyu Lu, Beijing (CN); Xinfang Hao, 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 May 18, 2021, as Appl. No. 17/323,274.
Claims priority of application No. 202010423833.4 (CN), filed on May 19, 2020; and application No. 202011492493.7 (CN), filed on Dec. 17, 2020.
Prior Publication US 2021/0380618 A1, Dec. 9, 2021
Int. Cl. H10K 85/30 (2023.01); C07F 7/08 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 85/60 (2023.01)
CPC C07F 15/0033 (2013.01) [C07F 7/0812 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); C09K 2211/1029 (2013.01); C09K 2211/1088 (2013.01); H10K 50/11 (2023.02); H10K 85/6572 (2023.02)] 32 Claims
OG exemplary drawing
 
1. A metal complex, wherein the metal complex has a maximum emission wavelength greater than or equal to 612 nm in a photoluminescence (PL) spectrum, wherein the metal complex has a structure of M(La)m(Lb)n(Lc)q and comprises a metal M selected from a metal with a relative atomic mass greater than 40, wherein
La, Lb and Lc are a first ligand, a second ligand, and a third ligand of the metal complex, respectively;
m is selected from 1, 2 or 3;
n is selected from 0, 1 or 2;
q is selected from 0, 1 or 2;
m+n+q is equal to the oxidation state of the metal M;
when m is greater than 1, the multiple La may be the same or different;
when n is 2, the two Lb may be the same or different;
when q is 2, the two Lc may be the same or different;
La, Lb and Lc can be optionally joined to form a multi-dentate ligand; and
ligand La has a structure represented by Formula 1:

OG Complex Work Unit Chemistry
wherein,
Z is selected from O;
X1 to X8 are, at each occurrence identically or differently, selected from C or CRx;
Y1 to Y6 are, at each occurrence identically or differently, selected from CRy1, CRy2 or N; at least one of Y1 to Y6 is selected from CRy1, and the Ry1 is fluorine, or at least one of Y1 to Y6 is selected from CRy2, and the Ry2 has a structure of -L-SiRs1Rs2Rs3;
Rx, Rs1, Rs2 and Rs3 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, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;
Ry1 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, 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 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, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof;
L is 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;
adjacent substituents Rx, Rs1, Rs2, Rs3 can be optionally joined to form a ring
Lb and Lc are, at each occurrence identically or differently, selected from the group consisting of the following structures:

OG Complex Work Unit Chemistry
wherein Ra, Rb and Rc represent, at each occurrence identically or differently, mono-substitution, multiple substitutions 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, 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;
wherein adjacent substituents Ra, Rb, Rc, RN1, RN2, RC1, RC2 can be optionally joined to form a ring.