US 12,275,747 B2
Organic electroluminescent materials and devices
Jui-Yi Tsai, Newtown, PA (US); Alexey Borisovich Dyatkin, Ambler, PA (US); Walter Yeager, Yardley, PA (US); and Pierre-Luc T. Boudreault, Pennington, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on May 19, 2021, as Appl. No. 17/324,598.
Claims priority of provisional application 63/033,605, filed on Jun. 2, 2020.
Prior Publication US 2021/0388013 A1, Dec. 16, 2021
Int. Cl. C07F 15/00 (2006.01); H01L 51/00 (2006.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01)
CPC C07F 15/0086 (2013.01) [H10K 85/346 (2023.02); H10K 85/40 (2023.02); H10K 85/622 (2023.02); H10K 85/624 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02)] 19 Claims
OG exemplary drawing
 
1. A compound of Formula I:

OG Complex Work Unit Chemistry
wherein:
M is Pt or Pd;
rings A, B, C, and D are each independently 5- or 6-membered aryl or heteroaryl rings;
RA, RB, RC, and RD each independently represent zero, mono, or up to maximum allowed substitutions to its associated ring;
Z1, Z2, Z3 and Z4 are each independently C or N;
L1, L2, L3, L4 are each independently a direct bond, BR, BRR′, NR, PR, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, GeR′R″, or combinations thereof;
n is 0 or 1;
each of R, R′, and R″ 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;
each of RA, RB, RC, and RD 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, with at least one of RA, RB, RC, and RD comprising a structure of Formula II:

OG Complex Work Unit Chemistry
X1-X13 are each independently C or N;
each of RE-RG has the same definition as that of RA, RB, RC, or RD;
the maximum number of N atoms that can connect with each other is two;
custom character represents a single bond or a double bond; and
any two adjacent RA, RB, RC, RD, R, R′, R″ substituents can be joined to form a ring, with a proviso that none of rings A, B, C, and D is an N-heterocyclic carbene ligand;
at least one of the following is true:
i) Z1 and Z4 are N, and Z2 and Z3 are C, or Z1 and Z4 are C, and Z2 and Z3 are N;
ii) three of rings A, B, C, and D are 6-membered aromatic rings, and the remaining one is a 5-membered aromatic ring; or
iii) at least one of L1 or L3 is selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, GeR′R″, or combinations thereof;
and
if ring A, B, C, or D is pyrazole, then said pyrazole comprises at least one hydrogen atom.