Phosphorescent materials

Patent metadata

Field	Value
Publication number	US-9175211-B2
Application number	US-86835010-A
Country	US
Kind code	B2
Filing date	Aug 25, 2010
Priority date	Mar 3, 2010
Publication date	Nov 3, 2015
Grant date	Nov 3, 2015

Abstract

Compounds comprising a 2-phenylpyridine ligand further substituted with a heterocyclic group are provided. In particular, the compound comprises a 2-phenylpyridine ligand further substituted with a nitrogen-containing heterocycle. The compounds may be used in organic light emitting devices to provide devices having improved efficiency and lifetime.

First claim

The invention claimed is:

1. A heteroleptic compound having the formula M(L) x (L 1 ) y (L 2 ) z :
wherein L is

wherein L 1 is

wherein L 2 is

wherein L 1 and L 2 can be the same or different;
wherein M is Ir;
wherein x is 1 or 2 , y is 1 or 2, z is 0, 1 or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein ring C is pyridine;
wherein ring D is phenyl;
wherein rings B, E and F are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein L and L 1 are different;
wherein R is a 6-membered heterocyclic aromatic ring that contains at least one nitrogen atom, wherein R is, optionally, further substituted by one or more of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein R A , R B , R C , R D , R E and R F may represent mono, di, tri, or tetra substitutions;
wherein each of R A , R B , R C , R D , R E and R F , is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and
wherein the ligand L is coordinated bidentately to the metal M, wherein said compound is heteroleptic.

2. The compound of claim 1 , wherein the ligand L has the formula:

wherein G is a 6-membered heterocyclic aromatic ring that contains at least one nitrogen atom;
wherein X 1 , X 2 , and X 3 are independently selected from carbon, oxygen, sulfur and nitrogen;
wherein R G may represent mono, di, tri, tetra, or penta substitutions;
wherein R G is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.

3. The compound of claim 2 , wherein X 1 , X 2 , and X 3 are independently carbon or nitrogen.

4. The compound of claim 2 , wherein at least one of X 1 , X 2 , and X 3 is nitrogen.

5. The compound of claim 2 , wherein each of X 1 , X 2 , and X 3 is carbon.

6. The compound of claim 2 , wherein the compound has the formula:

7. The compound of claim 1 , wherein B is phenyl.

8. The compound of claim 1 , wherein L, L 1 and L 2 are connected to form a tetradentate ligand and a bidentate ligand or a hexadentate ligand.

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

10. A compound selected from the group consisting of:

11. A first device comprising an organic light emitting device, further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, the organic layer comprising a first heteroleptic compound having the formula M(L) x (L 1 ) y (L 2 ) z :
wherein L is

wherein L 1 is

wherein L 2 is

wherein L 1 and L 2 can be the same or different;
wherein M is Ir;
wherein x is 1 or 2, y is 1 or 2, z is 0, 1 or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein ring C is pyridine;
wherein ring D is phenyl;
wherein rings B, E and F are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein L and L 1 are different;
wherein R is a 6-membered heterocyclic aromatic ring that contains at least one nitrogen atom, wherein R is, optionally, further substituted by one or more of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl;
wherein R A , R B , R C , R D , R E and R F may represent mono, di, tri, or tetra substitutions;
wherein each of R A , R B , R c , R D , R E and R F is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and
wherein the ligand L is coordinated bidentately to the metal M, wherein said first compound is heteroleptic.

12. The device of claim 11 , wherein the ligand L has the formula:

wherein G is a 6-membered heterocyclic aromatic ring that contains at least one nitrogen atom;
wherein X 1 , X 2 , and X 3 are independently selected from carbon, oxygen, sulfur and nitrogen;
wherein R G may represent mono, di, tri, tetra, or penta substitutions;
wherein R G is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.

13. The device of claim 12 , wherein X 1 , X 2 , and X 3 are independently carbon or nitrogen.

14. The compound of claim 12 , wherein at least one of X 1 , X 2 , and X 3 is nitrogen.

15. The device of claim 12 , wherein each of X 1 , X 2 , and X 3 is carbon.

16. The device of claim 12 , wherein the compound has the formula:

17. The device of claim 11 , wherein B is phenyl.

18. The device of claim 11 , wherein L, L 1 and L 2 are connected to form a tetradentate ligand and a bidentate ligand or a hexadentate ligand.

19. The device of claim 11 , wherein the ligand L is selected from the group consisting of:

20. The device of claim 11 , wherein the compound is selected from the group consisting of:

Assignees

• Xia Chuanjun
• Alleyne Bert
• Ansari Nasrin
• Universal Display Corp

Inventors

• Xia Chuanjun
• Alleyne Bert
• Ansari Nasrin

Classifications

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• 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

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title