US 12,171,139 B2
Organic electroluminescent materials and devices
Jui-Yi Tsai, Newton, PA (US); Eric A. Margulies, Philadelphia, PA (US); Zhiqiang Ji, Chalfont, PA (US); Alexey Borisovich Dyatkin, Ambler, PA (US); Walter Yeager, Yardley, PA (US); and Mingjuan Su, Ewing, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on May 18, 2023, as Appl. No. 18/319,759.
Application 18/319,759 is a continuation of application No. 16/902,697, filed on Jun. 16, 2020, granted, now 11,690,284.
Application 16/902,697 is a continuation of application No. 16/235,390, filed on Dec. 28, 2018, granted, now 10,727,423, issued on Jul. 28, 2020.
Application 16/235,390 is a continuation in part of application No. 15/728,737, filed on Oct. 10, 2017, granted, now 10,686,140, issued on Jun. 16, 2020.
Application 15/728,737 is a continuation in part of application No. 15/619,159, filed on Jun. 9, 2017, granted, now 10,651,403, issued on May 12, 2020.
Claims priority of provisional application 62/643,472, filed on Mar. 15, 2018.
Claims priority of provisional application 62/352,119, filed on Jun. 20, 2016.
Prior Publication US 2023/0292589 A1, Sep. 14, 2023
Int. Cl. C09K 11/06 (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)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); H10K 85/40 (2023.02); H10K 85/615 (2023.02); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1033 (2013.01); C09K 2211/1037 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. A compound having a metal coordination complex structure;
wherein the compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;
wherein the compound has a formula of Pt(LA)(LB), wherein LA and LB are each independently selected from the group consisting of:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein LA and LB may be joined to form a tetradentate ligand;
wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the maximum possible number of substitution, or no substitution;
wherein R′, R″, Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a tetradentate ligand;
wherein a free-state of ligand LA or a tetradentate ligand when LA and LB are joined together has a first triplet energy T1 of EL at 77K;
wherein the compound has a first triplet energy T1 of E at 77K;
wherein the difference in energy between E and EL is ΔE;
wherein ΔE is ≤250 meV; and
wherein the compound has a triplet emission spectrum with a full width at half maximum (FWHM) value of no more than 45 nm at 22° C.