US 12,065,451 B2
Organic electroluminescent materials and devices
Hsiao-Fan Chen, Lawrence Township, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Jul. 30, 2021, as Appl. No. 17/389,729.
Claims priority of provisional application 63/067,595, filed on Aug. 19, 2020.
Prior Publication US 2022/0056062 A1, Feb. 24, 2022
Int. Cl. H01L 51/50 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01); H10K 101/40 (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 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/40 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound of the following Formula I

OG Complex Work Unit Chemistry
wherein,
M is Pt or Pd;
A1, A2, A3, and A4 are each independently a monocyclic ring comprising one 5-membered or 6-membered carbocyclic or heterocyclic ring, or a multicyclic fused ring system comprising at least two fused 5-membered or 6-membered carbocyclic or heterocyclic rings;
Z1-Z4 are each independently C or N;
at least two of K1-K4 are direct bonds;
K1-K4 are independently selected from the group consisting of a direct bond, O, and S when their corresponding connecting Z1-Z4 are carbon;
K1-K4 are independently a direct bond when their corresponding connecting Z1-Z4 are nitrogen;
L1, L2, L3, and L4 are each independently selected from the group consisting of a direct bond, O, S, Se, BR, BRR′, NR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, and heteroaryl;
indeces a, b, c, and d are each independently 0 or 1, wherein 0 means not present and 1 means present;
a+b+c+d=3 or 4;
each R1, R2, R3, and R4 independently represents mono to the maximum allowable substitution, or no substitution;
each R, R′, R1, R2, R3, and R4 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;
at least one of R1, R2, R3, and R4 is RB having the following Formula II

OG Complex Work Unit Chemistry
 wherein
R5 and R6 are each independently 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;
any two adjacent R, R′, R1, R2, R3, R4, R5, and R6 can be joined or fused to form a ring, with the proviso that R5 and R6 do not join with R1, R2, R3, and R4 to form a ring; and
at least one of R5 and R6 bonds to B atom with a C or N atom.
 
17. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound of the following Formula I

OG Complex Work Unit Chemistry
wherein
M is Pt or Pd;
A1, A2, A3, and A4 are each independently a monocyclic ring comprising one 5-membered or 6-membered carbocyclic or heterocyclic ring, or a multicyclic fused ring system comprising at least two fused 5-membered or 6-membered carbocyclic or heterocyclic rings;
Z1-Z4 are each independently C or N;
at least two of K1-K4 are direct bonds;
K1-K4 are independently selected from the group consisting of a direct bond, O, and S when their corresponding connecting Z1-Z4 are carbon;
K1-K4 are independently a direct bond when their corresponding connecting Z1-Z4 are nitrogen;
L1, L2, L3, and L4 are each independently selected from the group consisting of a direct bond, O, S, Se, BR, BRR′, NR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, and heteroaryl;
indeces a, b, c, and d are each independently 0 or 1, wherein 0 means not present and 1 means present;
a+b+c+d=3 or 4;
each R1, R2, R3, and R4 independently represents mono to the maximum allowable substitution, or no substitution;
each R, R′, R1, R2, R3, and R4 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;
at least one of R1, R2, R3, and R4 is RB having the following Formula II

OG Complex Work Unit Chemistry
 wherein
R5 and R6 are each independently 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;
any two adjacent R, R′, R1, R2, R3, R4, R5, and R6 can be joined or fused to form a ring, with the proviso that R5 and R6 do not join with R1, R2, R3, and R4 to form a ring; and
at least one of R5 and R6 bonds to B atom with a C or N atom.