US 12,331,237 B2
Organic electroluminescent materials and devices
Zhiqiang Ji, Chalfont, PA (US); Pierre-Luc T. Boudreault, Pennington, NJ (US); Wei-Chun Shih, Lawrenceville, NJ (US); Walter Yeager, Yardley, PA (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 Sep. 16, 2020, as Appl. No. 17/022,151.
Claims priority of provisional application 63/010,815, filed on Apr. 16, 2020.
Claims priority of provisional application 62/906,305, filed on Sep. 26, 2019.
Prior Publication US 2021/0098717 A1, Apr. 1, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 50/11 (2023.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01); H10K 102/00 (2023.01)
CPC C09K 11/06 (2013.01) [C07F 15/0033 (2013.01); C09K 11/02 (2013.01); H10K 85/342 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1037 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 2101/10 (2023.02); H10K 2102/351 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound comprising a first ligand LA of Formula I:

OG Complex Work Unit Chemistry
wherein:
ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring, which can be further fused;
X1, X2, and X3 are each independently CRA or N;
R is a 5-membered or 6-membered aryl or heteroaryl ring, which can be further fused or substituted;
provided that
(1) when ring B is an unfused 6-membered ring, X1 and X2 are N, and X3 is C;
(2) when ring B is a fused 6-membered ring, ring B has the structure of Formula II;

OG Complex Work Unit Chemistry
wherein:
the wave line indicates the point of connection to ring A;
Q1, Q2, Q3, Q4, Q5, and Q6 are each independently C or N; and
when proviso (2) applies,
R is two or more fused or unfused 5-membered or 6-membered aryl or heteroaryl rings, which can be further fused or substituted, and if at least one of X1 to X3 is N, then R is further substituted by at least one substituent R′ that is other than H or D or at least one RA is other than H or D;
wherein RB and RC each independently represents mono to the maximum number of allowable substitutions, or no substitution;
each 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;
wherein LA is coordinated to a metal M through the indicated dashed lines;
wherein M is selected from the group consisting of Ir, Os, Pt, Pd, Cu, Ag, and Au;
wherein M can be coordinated to other ligands;
wherein LA can join with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein, with the exception of two RA, any two substituents can be joined or fused to form a ring.