Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10978649-B2
Application number	US-202016927285-A
Country	US
Kind code	B2
Filing date	Jul 13, 2020
Priority date	Feb 10, 2006
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

Compounds comprising phosphorescent metal complexes comprising cyclometallated ligands having a structure of

In the vgs3, each of the E 1 atoms is selected from C and N, except that E 1g is selected from C, N, and S. The E 1 atoms collectively comprise an 18 pi-electron system, provided that E 1a and E 1p are different. The R 1 substituents are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 2a R 2b , BR 2a R 2b , or SiR 2a R 2b R 2c , where the R 2 substituents are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl. Any of the R 1 or R 2 substituents can be linked to form a saturated or unsaturated, aromatic or non-aromatic ring, provided that the R 1 substituents are not present when the corresponding one of E atoms is N or S. Organic light emitting diode devices comprising these compounds are also described.

First claim

We claim:

1. A phosphorescent compound comprising a metal and a monoanionic, bidentate ligand as set forth below, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein:
E 1a-f , E 1h-i , and E 1k-q are selected from the group consisting of C and N, E 1g is selected from the group consisting of C, N, and S, and E la-i and E 1k-q collectively comprise an 18 pi-electron system, provided that E la and E lp are different;
R 1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 2a R 2b , BR 2a R 2b , or SiR 2a R 2b R 2c ;
R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl; and
where any two adjacent substituents selected from R 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;
provided that R 1a , R 1b , R 1d , R 1e , R 1g , R 1h , and R 1i are not present when the corresponding one of E 1b , E 1c , E 1h , E 1m , E 1n , and E 1o is N, and R 1c is not present when E 1g is Nor S.

2. The compound of claim 1 , wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au.

3. The compound of claim 1 , wherein the metal is selected from the group consisting of Os, Ir, and Pt.

4. The compound of claim 1 , wherein the metal is selected from the group consisting of Ir.

5. The compound of claim 1 , wherein the bidentate ligand is selected from the group consisting of:

6. The compound of claim 1 , wherein at least one of R 1a to R 1i is 2,6-disubstituted aryl or 2,6-disubstituted heteroaryl groups.

7. The compound of claim 1 , wherein at least one of R 1a to R 1i is selected from the group consisting of 2,6-dimethylphenyl; 2,4,6-trimethylphenyl; 2,6-di-isopropylphenyl; 2,4,6-triisopropylphenyl; 2,6-di-isopropyl-4-phenylphenyl; 2,6-dimethyl-4-phenylphenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-diphenylphenyl; 2,6-diphenyl-4-isopropylphenyl; 2,4,6-triphenylphenyl; 2,6-di-isopropyl-4-(4-isopropylphenyl); 2,6-di-isopropyl-4-(3,5-dimethylphenyl)phenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-di-isopropyl-4-(pyridine-4-yl)phenyl; and 2,6-di-(3,5-dimethylphenyl)phenyl.

8. The compound of claim 1 , wherein at least one pair of R 1a-i is linked to form an aromatic ring.

9. The compound of claim 1 , wherein at least one pair of R 2a-c is linked to form a non-aromatic ring.

10. The compound of claim 1 , wherein the compound is homoleptic.

11. The compound of claim 1 , wherein the compound is heteroleptic.

12. The compound of claim 1 , wherein the bidentate ligand is

13. The compound of claim 1 , wherein the bidentate ligand is

14. An organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a phosphorescent compound comprising a metal and a monoanionic, bidentate ligand as set forth below, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein:
E 1a-f , E 1h-i , and E 1k-q are selected from the group consisting of C and N, E 1g is selected from the group consisting of C, N, and S, and E 1a-i and E 1k-q collectively comprise an 18 pi-electron system, provided that E 1a and E 1p are different;
R 1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 2a R 2b , BR 2a R 2b , or SiR 2a R 2b R 2c ;
R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl; and
where any two adjacent substituents selected from R 1a-i and R 2a-c be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;
provided that R 1a , R 1b , R 1d , R 1e , R 1g , R 1h , and R 1i are not present when the corresponding one of E 1b , E 1c , E 1h , E 1m , E 1n , and E 1o is N, and R 1c is not present when E 1g is Nor S.

15. The OLED of claim 14 , wherein the metal is selected from the group consisting of Os, Ir, and Pt.

16. The OLED of claim 14 , wherein the metal is selected from the group consisting of Ir.

17. The OLED of claim 1 , wherein the bidentate ligand is selected from the group consisting of:

18. The OLED of claim 14 , wherein at least one of R 1a to R 1i is 2,6-disubstituted aryl or 2,6-disubstituted heteroaryl groups.

19. The compound of claim 14 , wherein at least one of R 1a to R 1i is selected from the group consisting of 2,6-dimethylphenyl; 2,4,6-trimethylphenyl; 2,6-di-isopropylphenyl; 2,4,6-triisopropylphenyl; 2,6-di-isopropyl-4-phenylphenyl; 2,6-dimethyl-4-phenylphenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-diphenylphenyl; 2,6-diphenyl-4-isopropylphenyl; 2,4,6-triphenylphenyl; 2,6-di-isopropyl-4-(4-isopropylphenyl); 2,6-di-isopropyl-4-(3,5-dimethylphenyl)phenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-di-isopropyl-4-(pyridine-4-yl)phenyl; and 2,6-di-(3,5-dimethylphenyl)phenyl.

20. A consumer product comprising an organic light-emitting device, the organic light-emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a phosphorescent compound comprising a metal and a monoanionic, bidentate ligand as set forth below, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein:
E 1a-f , E 1h-i , and E 1k-q are selected from the group consisting of C and N, E 1g is selected from the group consisting of C, N, and S, and E la-1 and E 1k-q collectively comprise an 18 pi-electron

Assignees

• Universal Display Corp

Inventors

• Knowles David
• Lin Chun
• Mackenzie Peter
• Tsai Jui-Yi
• Walters Robert W
• Beers Scott
• Brown Cory S
• Yeager Walter

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/18

  Metal complexes · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07F15/0086

  Platinum compounds · CPC title