US 12,245,504 B2
Organic electroluminescent materials and devices
Tyler Fleetham, Yardley, PA (US); Morgan C. Macinnis, Yardley, PA (US); Noah Horwitz, Ewing, NJ (US); Jerald Feldman, Cherry Hill, NJ (US); and 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 Oct. 14, 2021, as Appl. No. 17/501,114.
Claims priority of provisional application 63/107,244, filed on Oct. 29, 2020.
Claims priority of provisional application 63/105,845, filed on Oct. 26, 2020.
Prior Publication US 2022/0131088 A1, Apr. 28, 2022
Int. Cl. C07D 403/04 (2006.01); C07F 5/02 (2006.01); C07F 7/08 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (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 101/30 (2023.01); H10K 101/40 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 403/04 (2013.01); C07F 5/02 (2013.01); C07F 5/027 (2013.01); C07F 7/0816 (2013.01); C09K 11/02 (2013.01); C09K 11/06 (2013.01); H10K 85/322 (2023.02); H10K 85/40 (2023.02); H10K 85/623 (2023.02); H10K 85/654 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1022 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02)] 20 Claims
 
1. A compound of Formula I:

OG Complex Work Unit Chemistry
wherein:
X1 to X16 are each independently C or N;
Y1 to Y4 are each independently selected from the group consisting of direct bond, NR, PR, O, S, Se, CRR′, SiRR′, GeRR′, BR, and BRR′;
at least two adjacent sites from X1 to X16 are both carbon and are fused to one of

OG Complex Work Unit Chemistry
wherein:
* indicates the attachment point for each structure;
Y5 and Y8 are each independently selected from the group consisting of direct bond, NR, PR, O, S, Se, CRR′, SiRR′, GeRR′, BR, and BRR′;
Y6 and Y7 are each independently selected from the group consisting of N, NR, PR, O, S, Se, CR, CRR′, SiRR′, GeRR′, BR, and BRR′;
Z1 is C;
custom character is a single or double bond;
X17 to X32 are each independently C or N;
if X21 to X25 are all C, then at least one of RE comprises a boron atom;
Ring H is a 5 membered or 6 membered carbocyclic or heterocyclic ring;
RA, RB, RC, RD, RE, RF, RG, and RH each independently represents mono to the maximum allowable substitution, or no substitution;
each R, R′, RA, RB, RC, RD, RE, RF, RG, RH, and RX 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;
any two adjacent R, R′, RA, RB, RC, RD, RE, RF, RG, RH, and RX may be joined or fused to form a ring; and
at least one of Y1-Y4 is selected from the group consisting of NR, PR, O, S, Se, CRR′, SiRR′, GeRR′, BR, and BRR′, or the compound is subject to the following provisos:
if the compound comprises Formula III, then at least one of Y6 and Y7 is N;
in Formula II, if X21-X25 are each C, then: Y5 is a direct bond; or at least one RE and RF is a substituent selected from the group consisting of heterocycloalkyl, germyl, boryl, selenyl, and combinations thereof;
if the compound comprises the structure of Formula IV in which Y′ is an atom, then at least one of the following is true:
i) RX joins with an RA, RB, RC, or RD of the respective ring to which Formula IV is fused to form a fused ring;
ii) RX joins with RH to form a fused ring;
iii) RX comprises two or more aromatic rings; or
iv) Y′ is an atom that has a substituent and said substituent comprises two or more aromatic rings.