US 12,428,438 B2
Organic electroluminescent materials and devices
Lichang Zeng, Lawrenceville, NJ (US); Zhiqiang Ji, Hillsborough, NJ (US); Mingjuan T. Su, Ewing, NJ (US); Edward Barron, Hamilton, NJ (US); and Chun Lin, Yardley, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Oct. 13, 2022, as Appl. No. 17/965,283.
Application 17/965,283 is a continuation of application No. 15/805,483, filed on Nov. 7, 2017, granted, now 11,555,048.
Claims priority of provisional application 62/428,796, filed on Dec. 1, 2016.
Prior Publication US 2023/0183280 A1, Jun. 15, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 85/30 (2023.01); H10K 101/10 (2023.01)
CPC C07F 15/0086 (2013.01) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); H10K 50/11 (2023.02); H10K 85/342 (2023.02); H10K 85/346 (2023.02); C09K 2211/185 (2013.01); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound comprising a bidentate ligand LA of Formula I:

OG Complex Work Unit Chemistry
wherein G1 has at least one 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein G2 has at least two 5-membered or 6-membered carbocyclic or heterocyclic ring fused together;
wherein G1 and G2 are linked by a chemical group L having at least three backbone atoms;
wherein L is not fused with G1 or G2;
wherein LA is coordinated to a metal M;
wherein G2 comprises a first ring directly bonded to metal M and a second ring that is directly bonded to L, but not directly bonded to metal M;
wherein LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein M is optionally coordinated to other ligands; and
wherein at least one of the following is true:
(1) G1 is a 5-membered ring coordinated to metal M by N or carbene C and G2 either includes at least one 5-membered ring or includes a total of at least three rings;
(2) G1 is a 6-membered ring and at least one of the following conditions is true: (i) L comprises a moiety selected from the group consisting of cycloalkyl, aryl, heteroaryl, and silyl, (ii) G2 includes at least one 5-membered ring, or (iii) G2 comprises at least three 5-membered or 6-membered carbocyclic or heterocyclic rings;
(3) ligand LA has a structure selected from the group consisting of

OG Complex Work Unit Chemistry
 wherein, in the first structure, two R2 are not joined or fused to form a ring; or
(4) ligand LA has a structure of

OG Complex Work Unit Chemistry
 where two R1 or two R2 are joined or fused to form a ring;
wherein R1, R2, and R3 each independently represents none to a maximum allowable number of substituents;
wherein X is selected from a group consisting of O, S, Se, and NR4;
wherein each of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, and Z12 is independently selected from a group consisting of carbon and nitrogen;
wherein R1, R2, R3, and R4 each is independently selected from the group consisting of hydrogen, deuterium, halogen, nitrile, carbonyl, silyl, alkyl, cycloalkyl, alkyloxyl, cycloalkyloxyl, aryl, heteroaryl, and combinations thereof; and
wherein any two R1, R2, R3 and R4 are optionally joined to form a ring.