Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10749121-B2
Application number	US-201916511090-A
Country	US
Kind code	B2
Filing date	Jul 15, 2019
Priority date	Feb 10, 2006
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

Compounds comprising phosphorescent metal complexes comprising cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands, or isoelectronic or benzannulated analogs thereof, are described. 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-q are selected from the group consisting of C and N and collectively comprise an 18 pi-electron system, provided that E 1a and E 1p are different;
R 1b and R 1c are independently hydrocarbyl;
R 1a and R 1d-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 , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where R 1b and R 1c are linked and any two of other pair of adjacent substituents R 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring.

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, and the bidentate ligand is selected from the group consisting of:

3. The compound of claim 2 , wherein the bidentate ligand is of the formula gs1-1.

4. The compound of claim 2 , wherein the metal is Ir or Pt.

5. The compound of claim 1 , wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au, and at least one of R 1a-i is a 2,6-di-substituted aryl group, wherein if R 1b is a 2,6-di-substituted aryl group, the 2,6-di-substituted aryl group is linked to R 1c , and if R 1c is a 2,6-di-substituted aryl group, the 2,6-di-substituted aryl group is linked to R.

6. The compound of claim 5 , wherein R 1b is a 2,6-di-substituted aryl group and the 2,6-di-substituted aryl group is linked to R.

7. The compound of claim 6 , wherein the metal is Ir or Pt.

8. The compound of claim 5 , wherein the 2,6-di-substituted aryl group 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)phenyl; 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.

9. The compound of claim 1 , wherein any pair of adjacent substituents R 1d-i may be linked to only form a saturated, or non-aromatic ring.

10. The compound of claim 2 , wherein the compound is a homoleptic Ir complex.

11. The compound of claim 2 , wherein the compound is a heteroleptic Ir complex.

12. The compound of claim 1 , wherein R 1a and R 1d-i are each independently H, fluoro, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 8 cycloalkyl, or substituted or unsubstituted C 6 -C 18 aryl; R 1b and R 1c are independently substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 8 cycloalkyl, or substituted or unsubstituted C 6 -C 18 aryl; and the metal is Ir or Pt.

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

14. The compound of claim 13 , wherein each of E 1e-o and E 1q is carbon.

15. The compound of claim 13 , wherein at least one pair of adjacent substituents R 1c-i are linked to form a saturated or non-aromatic ring.

16. The compound of claim 1 , wherein the compound is:

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 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-q are selected from the group consisting of C and N and collectively comprise an 18 pi-electron system, provided that E 1a and E 1p ) are different;
R 1b and R 1c are independently hydrocarbyl;
R 1a and R 1d-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 , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where R 1b and R 1c are linked and any other pair of adjacent substituents R 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring.

18. The OLED of claim 17 , wherein the metal is Ir or Pt, and R 1b is a 2,6-di-substituted aryl group and the 2,6-di-substituted aryl group is linked to R.

19. The OLED of claim 17 , wherein the bidentate ligand is

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 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-q are selected from the group consisting of C and N and collectively comprise an 18 pi-electron system, provided that E 1a and E 1p ) are different;
R 1b and R 1c are independently hydrocarbyl;
R 1a and R 1d-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 , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where R 1b and R 1c are linked and any other pair of adjacent substituents R 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; and
wherein the consumer product is one of a flat panel display, a computer monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads up display, a fully transparent display, a flexible display, a laser printer, a telephone, a cell phone, a personal digital assistant (PDA), a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a vehicle, a large area wall, theater or stadi

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