US 12,227,525 B2
Organic electroluminescent materials and devices
Bin Ma, Plainsboro, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Jul. 20, 2020, as Appl. No. 16/933,458.
Claims priority of provisional application 62/886,394, filed on Aug. 14, 2019.
Prior Publication US 2021/0047353 A1, Feb. 18, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/00 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01)
CPC C07F 15/0033 (2013.01) [H10K 85/324 (2023.02); H10K 85/342 (2023.02); H10K 85/381 (2023.02); H10K 85/622 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 20 Claims
 
1. A compound of formula Ir(L1)x(L2)y(L3)z;
wherein:
L1 has

OG Complex Work Unit Chemistry
Y is selected from the group consisting of O, S, Se, NR, CRR′, and SiRR′;
L1 forms a 5-membered chelate ring with Ir;
L2 and L3 can be the same or different and have

OG Complex Work Unit Chemistry
wherein:
x and y are independently 1 or 2;
z is 0 or 1;
x+y+z=3;
RA represents mono to the maximum allowable substitutions;
RB and RC each represents mono to the maximum allowable substitutions, or no substitutions;
each R, R′, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R1, R2, R3, and R4 are each independently selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, and combinations thereof;
any two substituents, except two RA substituents, can be joined or fused together to form a ring;
L1, L2, and L3 are not joined to each other to form a tetradentate or hexadentate ligand;
L1 is different from L2 and L3; and
at least one of the following condition is true:
(1) one of R1 and R2 comprises an aryl or heteroaryl group, and the other one of R1 and R2 doesn't comprise a cyclic group, and at least one R3, R4, RB or RC is aryl or heteroaryl, that may optionally be substituted;
(2) at least one RA is not H or D, and at least one R3, R4, RB or RC is aryl or heteroaryl, that may optionally be substituted;
(3) R1 and R2 are joined to form a ring; or
(4) R1 and R2 each comprise at least four carbon.