US 12,459,955 B2
Organic electroluminescent materials and devices
Chuanjun Xia, Lawrenceville, NJ (US); Lichang Zeng, Lawrenceville, NJ (US); Walter Yeager, Yardley, PA (US); and Zhiqiang Ji, Hillsborough, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Aug. 9, 2021, as Appl. No. 17/397,373.
Application 17/397,373 is a continuation of application No. 15/173,806, filed on Jun. 6, 2016, granted, now 11,127,905.
Claims priority of provisional application 62/198,173, filed on Jul. 29, 2015.
Prior Publication US 2021/0376256 A1, Dec. 2, 2021
Int. Cl. C07D 495/04 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/18 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC C07D 495/04 (2013.01) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/18 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound having a formula selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein X is selected from the group consisting of O, S, and Se;
wherein X1 to X10 are each independently selected from the group consisting of carbon and nitrogen;
wherein at least one of X1 to X6 is nitrogen;
wherein R and R′ each independently represent from mono to the possible maximum number of substitutions, or no substitution;
wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substitutions on the same ring are optionally joined or fused into a ring;
wherein at least one pair of adjacent substitutions on the same ring are joined or fused into a ring; and
wherein at least one of the following is true:
(i) an R′ is bonded to X1, X2, or X3 and comprises aryl or heteroaryl, and two adjacent R′ are joined or fused to form a ring;
(ii) the compound has a structure of Formula 1-1 or Formula 1-2, and at least one of an R′ is bonded to X4 and comprises aryl or heteroaryl or an R is bonded to X5 and comprises aryl or heteroaryl;
(iii) the compound has a structure of Formula 1-3, and at least one of an R′ is bonded to X4 and comprises aryl or heteroaryl or an R is bonded to X7 and comprises aryl or heteroaryl;
(iv) (a) at least one pair of adjacent substitutions on the same ring are joined or fused into a 6-membered ring and (b) an R is bonded to X6, X7, X8, X9, or X10 and comprises aryl or heteroaryl, and the R does not comprise anthracene and if an amino is present, the amino is part of a substituted or unsubstituted carbazole; or
(v) the compound has a structure of Formula 1-3 and an R is bonded to X5 and comprises aryl or heteroaryl, and the R does not comprise anthracene and if an amino is present, the amino is part of a substituted or unsubstituted carbazole;
provided that when adjacent substitutions on X5 and X6 in Formula 1-1 and 1-3 fuse into a six-membered ring, this ring and the ring having X1 to X10 can not be pyridine at the same time, and
provided that when adjacent substitutions on X5 and X6 in Formula 1-1 fused into phenyl, exactly one of X1 to X4 is N.