Granted Patent B2

US 12,317,745 · App. 15/792,893 · Granted May 27, 2025

Inventors: Pierre-Luc T. Boudreault (Ewing, NJ); Bert Alleyne (Ewing, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/6572C07D209/82C07D239/70C07D239/78C07D251/42C07F15/00C09K11/06G09F9/30H05B33/12H05B33/14H10K50/00H10K59/00H10K85/6574H10K85/6576H10K99/00

Abstract

Claims (56)

1. A compound comprising a ligand L A , having a structure of

wherein:

the combination of ring A and R 1 has a structure selected from the group consisting of:

wherein each bond ------- is linked to the azaphenanthrene and each bond ″″″″″″ is linked to the metal;

wherein L A is coordinated to an Ir atom;

wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein Ir is optionally coordinated to other ligands.

2. The compound of claim 1 , wherein the compound has a formula of M(L A ) n (L B ) m-n ;

wherein M is Ir;

L B is a bidentate ligand; and

wherein m is 3, and n is 1, 2, or 3.

3. The compound of claim 2 , wherein L B is selected from the group consisting of:

wherein each X 1 to X 13 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, SO 2 , CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;

wherein R′, R″, R a , R b , R c , and R d 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 R a , R b , R c , and R d are optionally fused or joined to form a ring or to form a multidentate ligand.

4. The compound of claim 1 , wherein the compound has the formula Ir(L A ) 2 (L Cj ); and

wherein L C is selected from the group consisting of:

5. The compound of claim 4 , wherein no two R 1 are joined to form a ring, the R 1 para to the Ir is not hydrogen, the R 1 ortho to the Ir is not hydrogen; and the remaining R 1 are hydrogen.

6. The compound of claim 4 , wherein the combination of ring A and R 1 have a structure selected from the group consisting of:

7. The compound of claim 4 , wherein the combination of ring A and R 1 have a structure of

8. The compound of claim 1 , wherein the compound has the formula Ir(L A )(L Bk ) 2 ; and

wherein L B is selected from the group consisting of:

9. The compound of claim 8 , wherein no two R 1 are joined to form a ring, the R 1 para to the Ir is not hydrogen, the R 1 ortho to the Ir is not hydrogen; and the remaining R 1 are hydrogen.

10. The compound of claim 8 , wherein the combination of ring A and R 1 have a structure selected from the group consisting of:

11. The compound of claim 1 , wherein no two R 1 are joined to form a ring.

12. The compound of claim 11 , wherein the R 1 para to the Ir is not hydrogen, the R 1 ortho to the Ir is not hydrogen; and the remaining R 1 are hydrogen.

13. The compound of claim 11 , wherein the R 1 para to the Ir is alkyl, the R 1 ortho to the Ir is alkyl; and the remaining R 1 are hydrogen.

14. The compound of claim 11 , wherein the combination of ring A and R 1 have a structure selected from the group consisting of:

15. The compound of claim 1 , wherein the combination of ring A and R 1 have a structure of

16. A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L A ,

wherein:

the combination of ring A and R 1 has a structure selected from the group consisting of:

wherein each bond ------- is linked to the azaphenanthrene and each bond ″″″″″″″ is linked to the metal;

wherein L A is coordinated to an Ir atom;

wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein Ir is optionally coordinated to other ligands.

17. An organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L A ,

wherein:

the combination of ring A and R 1 has a structure selected from the group consisting of:

wherein each bond ------- is linked to the azaphenanthrene and each bond ″″″″″″ is linked to the metal;

wherein L A is coordinated to an Ir atom;

wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein Ir is optionally coordinated to other ligands.

18. The OLED of claim 17 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

19. The OLED of claim 17 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

20. The OLED of claim 17 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

Assignments (1)

Continuity (2)

References Cited (218)