Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9893306-B2
Application number	US-201715659884-A
Country	US
Kind code	B2
Filing date	Jul 26, 2017
Priority date	Feb 10, 2006
Publication date	Feb 13, 2018
Grant date	Feb 13, 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. An emissive layer in an organic light emitting device, the emissive layer 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 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; provided that R 1a-i is other than H when attached to N, and

is excluded from the bidentate ligand.

2. The emissive layer of claim 1 , wherein the metal is Ir or Pt, and R 1b is a 2,6-di-substituted aryl group.

3. The emissive layer of claim 1 , wherein the bidentate ligand is

4. The emissive layer 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 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring.

5. The emissive layer of claim 4 , wherein the bidentate ligand is of the formula gs1-1.

6. The emissive layer of claim 4 , wherein the metal is Ir or Pt.

7. The emissive layer of claim 1 , further comprising a host material capable of transporting electrons.

8. The emissive layer of claim 1 , further comprising a host material capable of transporting holes.

9. The emissive layer of claim 1 , further comprising a fluorescent emissive material.

10. 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 a 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 1i-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; provided that R 1a-i is other than H when attached to N, and

is excluded from the bidentate ligand.

11. The OLED of claim 10 , 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 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring.

12. The OLED of claim 11 , wherein the bidentate ligand is of the formula gs1-1.

13. The OLED of claim 11 , wherein the metal is Ir or Pt.

14. The OLED of claim 10 , 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.

15. The OLED of claim 10 , wherein the organic layer further comprising a host material capable of transporting electrons.

16. The OLED of claim 10 , wherein the organic layer further comprising a host material capable of transporting holes.

17. The OLED of claim 10 , wherein the organic layer further comprising a fluorescent emissive material.

18. The OLED of claim 10 , wherein the organic layer further comprising an electron transporting layer.

19. 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 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

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

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1066

  with sulfur · CPC title

• C09K2211/1048

  with oxygen · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title