US 12,239,012 B2
Organic electroluminescent materials and devices
Hsiao-Fan Chen, Lawrence Township, NJ (US); Jason Brooks, Philadelphia, PA (US); Douglas Williams, Mullica Hill, NJ (US); Charles J. Stanton, III, Wilmington, DE (US); Eugene S. Gutman, Philadelphia, PA (US); and Wei Bao, Hockessin, DE (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, PA (US)
Filed on May 24, 2023, as Appl. No. 18/322,617.
Application 18/322,617 is a continuation of application No. 16/884,545, filed on May 27, 2020, granted, now 11,700,765.
Application 16/884,545 is a continuation in part of application No. 16/217,467, filed on Dec. 12, 2018, granted, now 11,081,659.
Claims priority of provisional application 62/615,729, filed on Jan. 10, 2018.
Prior Publication US 2024/0049590 A1, Feb. 8, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/02 (2013.01); C09K 11/06 (2013.01); C09K 2211/1022 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/104 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. A compound selected from the group consisting of:
a structure having

OG Complex Work Unit Chemistry
and a structure having

OG Complex Work Unit Chemistry
wherein rings A and B are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein M is Pt or Pd;
wherein T1 and T2 are C;
wherein X1-X5, Z1, and Z2 are each independently selected from the group consisting of carbon and nitrogen;
wherein each RA, RB, RC, and RD represents mono to a maximum possible number of substitutions, or no substitution;
wherein Y1 is selected from the group consisting of CRR′, SiRR′, GeR″R″′, BR, O, and S;
wherein Y2 and Y3 are each selected from the group consisting of CRR′, SiRR′, BR, NR, O, and S;
wherein if one of Y2 and Y3 is O, S, or NR, the other is not O, S, or NR;
wherein n1 and n2 are each independently 0 or 1;
wherein when n1 or n2 is 1, L1 or L2 is present
wherein when n1 or n2 is 0, L1 or L2 is not present;
wherein n1+n2 is at least 1;
wherein if present, L1 and L2 are 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, cycloalkyl, and combinations thereof;
wherein R1, R2, R, R′, 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, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R″ and R″′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heterocycloalkyl, arylalkyl, amino, aryl, heteroaryl, ether, and combinations thereof;
wherein any two substituents may be joined or fused together to form a ring;
when Y1 is CRR′, BR, O, or S, R1 comprises aryl;
when Y1 is BR, at least one of the following is true:
i) R in BR is a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
ii) R1 is an aryl group comprising three or more phenyl rings that are joined to form a chain; or
iii) n2 in Formula I is 1 and L2 is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
when Y1 is SiRR′, at least one of the following is true:
i) R and R′ in SiRR′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein if aryl or heteroaryl are present, the aryl or heteroaryl are joined to form a fused ring; or
ii) R1 is an aryl group comprising three or more phenyl rings that are joined to form a chain;
if Y2 is CRR′ wherein at least one of R and R′ is hydrogen or deuterium, then at least one of the following is true:
i) the other of R and R′ of Y2 is a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; or
ii) Y3 is CRR′ wherein at least one of R and R′ is hydrogen or a substituent selected from the group consisting of deuterium, halogen, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.