US 11,903,306 B2
Organic electroluminescent materials and devices
Zhiqiang Ji, Hillsborough, NJ (US); Lichang Zeng, Lawrenceville, NJ (US); Jui-Yi Tsai, Newtown, PA (US); Chun Lin, Yardley, PA (US); Chuanjun Xia, Lawrenceville, NJ (US); Alexey Borisovich Dyatkin, Ambler, PA (US); and Walter Yeager, Yardley, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Dec. 20, 2022, as Appl. No. 18/069,016.
Application 17/075,989 is a division of application No. 15/619,170, filed on Jun. 9, 2017, granted, now 10,862,054, issued on Dec. 8, 2020.
Application 18/069,016 is a continuation of application No. 17/075,989, filed on Oct. 21, 2020, granted, now 11,588,121.
Claims priority of provisional application 62/516,329, filed on Jun. 7, 2017.
Claims priority of provisional application 62/480,746, filed on Apr. 3, 2017.
Claims priority of provisional application 62/479,795, filed on Mar. 31, 2017.
Claims priority of provisional application 62/450,848, filed on Jan. 26, 2017.
Claims priority of provisional application 62/352,139, filed on Jun. 20, 2016.
Prior Publication US 2023/0133996 A1, May 4, 2023
Int. Cl. H10K 85/30 (2023.01); C09K 11/06 (2006.01); C09K 11/02 (2006.01); C07F 15/00 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/81 (2023.01); H10K 50/00 (2023.01); H10K 101/10 (2023.01); H10K 101/00 (2023.01); H10K 50/82 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/346 (2023.02); H10K 85/622 (2023.02); H10K 85/654 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (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 rings A, B, C, and D are each a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein in Formula III:
L1 and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
n1, n2 each independently is 0 or 1;
when n1 or n2 is 1, L2 or L4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof; and
when n1 or n2 is 0, L2 or L4 is not present;
Q1, Q2, Q3 and Q4 each independently selected from the group consisting of direct bond and oxygen;
when any of Z1, Z2, Z3 and Z4 is nitrogen, the Q1, Q2, Q3 and Q4 attached thereto is a direct bond;
ring A is trans to ring D, ring B is trans to ring C in a square-planar coordination configuration;
wherein R1, R2, R3, and R4 each represents mono to the maximum possible number of substitution, or no substitution;
wherein Z1, Z2, Z3, and Z4 are each independently selected from the group consisting of carbon and nitrogen;
wherein M2 is a metal selected from the group consisting of Pt and Pd;
wherein a fourth distance is the distance between the atom in R1 that is the farthest away from M2 to the atom in R4 that is the farthest away from M2;
wherein a fifth distance is the distance between the atom in R2 that is the farthest away from M2 to the atom in R3 that is the farthest away from M2;
wherein the fourth distance is longer than the fifth distance by at least 4.3 Å;
wherein R, R′, R1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein (i) each of R1 and R4 comprises at least one cyclic moiety selected from the group consisting of aryl, heteroaryl, and cycloalkyl, or (ii) at least one of R1 and R4 comprises at least two cyclic moieties each independently selected from the group consisting of aryl, heteroaryl, and cycloalkyl; and
wherein any two substituents among R, R′, R1, R2, R3, and R4 are optionally joined or fused into a ring.