US 12,262,628 B2
Organic electroluminescent materials and devices
Hsiao-Fan Chen, Lawrence Township, NJ (US); Tyler Fleetham, Newtown, PA (US); and Rasha Hamze, Philadelphia, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Feb. 9, 2024, as Appl. No. 18/437,316.
Application 18/437,316 is a continuation of application No. 16/944,629, filed on Jul. 31, 2020, granted, now 11,937,494.
Claims priority of provisional application 62/892,789, filed on Aug. 28, 2019.
Prior Publication US 2024/0260445 A1, Aug. 1, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/30 (2023.01); C07F 5/02 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/12 (2023.01); H10K 101/00 (2023.01)
CPC H10K 85/322 (2023.02) [C07F 5/027 (2013.01); C09K 11/02 (2013.01); C09K 11/06 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1018 (2013.01); H10K 50/121 (2023.02); H10K 2101/27 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound of Formula I

OG Complex Work Unit Chemistry
wherein:
rings A and B are each independently a 5-membered or 6-membered heterocyclic ring;
rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
L is N or CR;
X is O, S, NR, BR, BRR′, CRR′, or SiRR′;
RA, RB, RC, and RD each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
RA, RB, RC, and RD are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R and R′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;
two substituents can be joined or fused to form a ring; and
with the proviso that if rings A and B are both a 5-membered heterocyclic ring, then:
one of the following conditions i) and ii) is true:
i) L is N; or
ii) L is CR and R is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein if R is aryl, the aryl is a substituted aryl;
and at least one of the following conditions iii) and iv) is true:
iii) in at least one of ring A and ring B, the atom adjacent to the nitrogen atom is a carbon substituted with hydrogen; or
iv) two RA or two RB are joined to form a ring.