Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10158090-B2
Application number	US-201815860737-A
Country	US
Kind code	B2
Filing date	Jan 3, 2018
Priority date	Feb 10, 2006
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

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; and
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 , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1b-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:

wherein:
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 , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1b-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring.

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.

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

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 two of R 1b-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-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; 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 R 1b-i are linked to form a saturated, or non-aromatic ring.

16. The compound of claim 15 , wherein the compound is selected from the group consisting of:

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; and
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 , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1b-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring.

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

19. An 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; and
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 , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1b-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 stadium screen, or a sign.

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

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/1062

  with oxygen · CPC title

• C09K2211/1066

  with sulfur · CPC title

• C09K2211/1055

  with other heteroatoms · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title