US 12,295,251 B2
Organic electroluminescent materials and devices
Bin Ma, Plainsboro, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Jun. 24, 2020, as Appl. No. 16/910,870.
Claims priority of provisional application 62/881,432, filed on Aug. 1, 2019.
Prior Publication US 2021/0036244 A1, Feb. 4, 2021
Int. Cl. H10K 85/40 (2023.01); C07F 7/08 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/40 (2023.02) [C07F 7/0816 (2013.01); C09K 11/02 (2013.01); C09K 11/06 (2013.01); H10K 85/6572 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 17 Claims
OG exemplary drawing
 
1. A compound of Formula I

OG Complex Work Unit Chemistry
wherein:
the dashed line between the phenyl rings containing R5 and R6 represents a single bond, the dashed line between the phenyl rings containing R3 and R4 represents no bond;
R3, R4, R5, and R6 each independently represents zero, mono, or up to a maximum allowed substitutions to its associated phenyl ring;
each R3, R4, and the R5 or R6 on the ring containing R is independently 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;
the other of R5 or R6 on the ring without R is 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; and
R is a group represented by Formula IV shown below:

OG Complex Work Unit Chemistry
R bonds to Formula I at a carbon atom that is para to the dashed line between the phenyl rings containing R5 and R6 from X1, X2, X4, X5, X7, or X8 of Formula IV;
wherein,
each R1 and R2 is independently selected from 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;
R1 and R2 each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
X1-X8 are each independently C or N;
at least two of X1-X8 are N;
any one of X1-X8 that is C directly bonds to the structure of Formula I;
if one of X1-X4 is C and directly bonds to the structure of Formula I, the remaining X1-X4 are also C;
if one of X5-X8 is C and directly bonds to the structure of Formula I, the remaining X5-X8 are also C;
exactly one carbon atom separates the at least two X1-X8 that are N, wherein said carbon atom has a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, unsubstituted aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
Y is O, S, or NR′, wherein R′ is a substituent selected from the group consisting of hydrogen, 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.