US 12,331,065 B2
Organic electroluminescent materials and devices
Wei-Chun Shih, Lawrenceville, NJ (US); Zhiqiang Ji, Chalfont, PA (US); Pierre-Luc T. Boudreault, Pennington, NJ (US); Walter Yeager, Yardley, PA (US); Bert Alleyne, Newton, PA (US); Derek Wozniak, Bensalem, PA (US); and James Fiordeliso, Morrisville, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Jul. 20, 2021, as Appl. No. 17/380,518.
Application 17/380,518 is a continuation in part of application No. 17/022,151, filed on Sep. 16, 2020.
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 2022/0402954 A1, Dec. 22, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 50/11 (2023.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01)
CPC C07F 15/0033 (2013.01) [H10K 85/342 (2023.02); H10K 85/40 (2023.02); H10K 85/622 (2023.02); H10K 85/624 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound comprising a first ligand LA of the following 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 carbocyclic or heterocyclic 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 the following Formula II;

OG Complex Work Unit Chemistry
wherein:
the wave line indicates the point of connection to ring A;
Q1, Q2, Q3, Q1, Q5, and Q6 are each independently C or N; and
when proviso (2) applies, at least one of the following conditions is true:
(I) R is two or more fused or unfused 5-membered or 6-membered carbocyclic or heterocyclic 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; or
(II) at least ring A or R is substituted with a partially or fully deuterated alkyl or partially or fully deuterated cycloalkyl group;
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, germyl, boryl, selenyl, 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;
wherein if R is joined or fused with an RA to form a ring, then R is a 5-membered or 6-membered aryl or heteroaryl ring, which can be further fused or substituted; and
wherein any two, RB or RC substituents can be joined or fused to form a ring.