US 12,453,279 B2
Organic electroluminescent materials and devices
Pierre-Luc T. Boudreault, Pennington, NJ (US); and Bert Alleyne, Newtown, PA (US)
Assigned to Universal Display Corporation, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Jul. 23, 2019, as Appl. No. 16/519,287.
Claims priority of provisional application 62/720,983, filed on Aug. 22, 2018.
Prior Publication US 2020/0075870 A1, Mar. 5, 2020
Int. Cl. H10K 85/30 (2023.01); C07D 209/82 (2006.01); H10K 85/60 (2023.01)
CPC H10K 85/342 (2023.02) [C07D 209/82 (2013.01); H10K 85/346 (2023.02); H10K 85/622 (2023.02); H10K 85/636 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C07B 2200/05 (2013.01)] 20 Claims
OG exemplary drawing
 
1. A compound having a formula selected from the group consisting of Ir(LA)3, Ir(LA)(LB)2, Ir(LA)2(LB), Ir(LA)2(LC), and Ir(LA)(LB)(LC); wherein LB and LC are each a bidentate ligand, and wherein LA, LB, and LC are different from each other, wherein LA has the structure
of Formula I

OG Complex Work Unit Chemistry
wherein,
RA represents mono to the maximum allowable substitutions;
X1 to X4 are each independently CR or N;
RA, R, R1, and R2 are each independently selected from the group consisting of hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
at least one RA is not hydrogen;
at least one of R1 and R2 has the formula of -L1-G1;
L1 is an organic linker or a direct bond, G1 is a substituted cycloalkyl group or a substituted or unsubstituted spirocycle;
wherein when G1 is a substituted cycloalkyl group, the substituted cycloalkyl group is selected from the group consisting of alkyl substituted cycloalkyl, a partially or fully fluorinated cycloalkyl or alkyl substituted cycloalkyl;
LA is coordinated to Ir;
Ir can be coordinated to other ligands;
LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
two substituents RA are joined or fused together to form an aryl group, wherein RA or said aryl group further comprises a branched alkyl, a cycloalkyl, or a silyl;
R1 and R2 are not joined to form a ring;
wherein LB and LC are each independently selected from the group consisting of:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein,
Y1 to Y13 are each independently selected from the group consisting of carbon and nitrogen;
Y′ is selected from the group consisting of BRe, NRe, PRe, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf,
Re and Rf are optionally fused or joined to form a ring;
each Ra, Rb, Rc, and Rd can independently represent from mono substitution to the maximum possible number of substitutions, or no substitution;
Ra, Rb, Rc, Rd, Re and Rf are each independently selected from the group consisting of hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.