US 9,812,656 B2
Organic electroluminescent materials and devices
Chun Lin, Ewing, NJ (US); Chuanjun Xia, Ewing, NJ (US); Bin Ma, Ewing, NJ (US); Lichang Zeng, Ewing, NJ (US); Alan DeAngelis, Ewing, NJ (US); and Edward Barron, Ewing, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Appl. No. 14/113,533
Filed by Chun Lin, Ewing, NJ (US); Chuanjun Xia, Ewing, NJ (US); Bin Ma, Ewing, NJ (US); Lichang Zeng, Ewing, NJ (US); Alan DeAngelis, Ewing, NJ (US); and Edward Barron, Ewing, NJ (US)
PCT Filed Jun. 6, 2012, PCT No. PCT/US2012/040993
§ 371(c)(1), (2), (4) Date Jan. 13, 2014,
PCT Pub. No. WO2012/170463, PCT Pub. Date Dec. 13, 2012.
Claims priority of provisional application 61/494,667, filed on Jun. 8, 2011.
Prior Publication US 2014/0131687 A1, May 15, 2014
Int. Cl. H01L 51/00 (2006.01); C07F 15/00 (2006.01); H01L 51/50 (2006.01)
CPC H01L 51/0085 (2013.01) [C07F 15/0033 (2013.01); H01L 51/50 (2013.01); H01L 51/5012 (2013.01); H01L 51/0072 (2013.01); H01L 51/5016 (2013.01)] 20 Claims
OG exemplary drawing
 
1. A compound comprising a heteroleptic iridium complex having the formula:

OG Complex Work Unit Drawing
wherein R2, Rx, Ra, and Rb, represent mono, di, tri, tetra substitutions or no substitution;
wherein R1 is an alkyl or cycloalkyl with a molecular weight higher than 15.5 g/mol;
wherein X is selected from the group consisting of CRR′, SiRR′, C═O, N—R, B—R, O, S, SO, SO2, and Se;
wherein R, R′, R2, Rx, Ra, and Rb 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;
wherein Rc comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, and fluorine;
wherein any two adjacent substituents of R2, Ra, or both are optionally joined to form a ring, which may be further substituted;
and wherein n is 1 or 2.