US 12,473,318 B2
Organic electroluminescent materials and devices
Fadi M. Jradi, Abington, PA (US); Hsiao-Fan Chen, Lawrence Township, NJ (US); Nicholas J. Thompson, New Hope, PA (US); and Tyler Fleetham, Yardley, PA (US)
Assigned to Universal Display Corporation, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Mar. 29, 2022, as Appl. No. 17/656,885.
Claims priority of provisional application 63/314,827, filed on Feb. 28, 2022.
Claims priority of provisional application 63/310,330, filed on Feb. 15, 2022.
Claims priority of provisional application 63/266,781, filed on Jan. 14, 2022.
Claims priority of provisional application 63/262,587, filed on Oct. 15, 2021.
Claims priority of provisional application 63/262,247, filed on Oct. 8, 2021.
Prior Publication US 2023/0146345 A1, May 11, 2023
Int. Cl. H01L 51/54 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01)
CPC C07F 15/0086 (2013.01) [H10K 85/322 (2023.02); H10K 85/346 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02)] 20 Claims
 
1. A compound of Formula I:

OG Complex Work Unit Chemistry
wherein
rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z1 and Z2 are independently C or N;
K1, K2, K3, and K4 are each independently a direct bond, O, or S;
at least two of K1, K2, K3, and K4 are a direct bond;
X1-X8, X21, and X22 are each independently C or N;
L is selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′;
L1, L2, and L3 are each independently a direct bond, a single atom linker, or a two atom linker selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, GeRR′, and combinations thereof,
at least one of conditions (1), (2), (3), (4), (5), (6) or (7) is met:
(1) at least two of X1-X8 are N;
(2) X1 and X8 are both C, and at least one of X2—X7 is N;
(3) X1 and X8 are both C, and one of K1 and K2 is not a direct bond;
(4) at least one of K1, K2, K3, and K4 is not a direct bond;
(5) ring D is a six-membered ring and comprises at least one N that is not Z2;
(6) L2 is present and is not a direct bond;
(7) rings C and D are each independently a 6-membered carbocyclic or heterocyclic ring;
a, b, and c are each independently 0 or 1;
a+b+c=2 or 3;
X2 is C if a=1 and L1 is selected from the group consisting of BR, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′, and X7 is C if c=1 and L3 is selected from the group consisting of BR, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′; X1, X8, Z1, and Z2 are C if bonded to O or S;
RA, RB, RC, and RD each independently represent mono to the maximum allowable substitution, or no substitution;
each R, R′, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof,
each R″ is independently selected from the group consisting of O, S, NR and CRR′
M is Pt or Pd; and
any two adjacent R, R′, RA, RB, RC, and RD can be joined or fused to form a ring; and
with the proviso that the compound does not comprise Formula II:

OG Complex Work Unit Chemistry
wherein R1 and R2 are each independently alkyl or aryl; LX is a direct bond, CRXRX, or NRX; LY is a direct bond or NRX; RX is an aryl group that does not connect to ring X, ring Y, or ring Z; and Z1 and Z2 are C or N.