Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10056566-B2
Application number	US-201414225591-A
Country	US
Kind code	B2
Filing date	Mar 26, 2014
Priority date	Mar 23, 2009
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

Novel heteroleptic iridium complexes having the structure of Formula I,

are provided. In Formula I, X is selected from the group consisting of NR, BR, and Se; R is selected from hydrogen and alkyl, and each R 1 , R 2 , R 3 , and R 4 is independently selected from hydrogen, alkyl, and aryl. The compounds may be used in organic light emitting devices, particularly as emitting dopants, to provide devices having improved efficiency, lifetime, and manufacturing.

First claim

The invention claimed is:

1. A heteroleptic compound having the formula:

wherein X is NR;
wherein R is isobutyl;
wherein R 1 , R 2 , R 3 , and R 4 may represent mono, di, tri, or tetra substitutions; and
wherein each of R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of hydrogen, alkyl, and aryl.

2. The heteroleptic compound of claim 1 , wherein R 1 and R 4 are independently selected from the group consisting of hydrogen and alkyl having four or fewer carbon atoms.

3. The heteroleptic compound of claim 1 , wherein R 2 and R 3 are independently selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms and aryl comprising an aryl ring with 5 or 6 atoms in the aryl ring.

4. The heteroleptic compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms and aryl comprising an aryl ring with 5 or 6 atoms in the aryl ring.

5. The heteroleptic compound of claim 1 , wherein the compound has the formula:

6. The heteroleptic compound of claim 1 , wherein the compound has the formula:

7. The heteroleptic compound of claim 1 , wherein the compound has the formula:

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

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

10. A first device comprising an organic light emitting device, comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, the organic layer comprising a heteroleptic compound having the formula:

wherein X is NR;
wherein R is isobutyl;
wherein R 1 , R 2 , R 3 and R 4 may represent mono, di, tri, or tetra substitutions;
wherein each of R 1 , R 2 , R 3 and R 4 is independently selected from the group consisting of hydrogen, alkyl, and aryl.

11. The device of claim 10 , wherein the organic layer is an emissive layer and the heteroleptic compound is an emitting dopant.

12. The device of claim 10 , wherein the organic layer further comprises a host.

13. The device of claim 12 , wherein the host comprises a triphenylene moiety and a dibenzothiophene moiety.

14. The device of claim 12 , wherein the host has the formula:

wherein R′ 1 , R′ 2 , R′ 4 , and R′ 6 may represent mono, di, tri, or tetra substitutions;
wherein R′ 3 and R′ 5 may represent mono, di, or tri substitutions; and
wherein each of R′ 1 , R′ 2 , R′ 3 , R′ 4 , R′ 5 , and R′ 6 is independently selected from the group consisting of hydrogen, alkyl, and aryl.

15. A heteroleptic compound having the formula:

wherein X is selected from the group consisting of BR and Se;
wherein R is selected from hydrogen and alkyl;
wherein R 1 , R 2 , R 3 , and R 4 may represent mono, di, tri, or tetra substitutions; and
wherein each of R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of hydrogen, alkyl, and aryl.

16. The heteroleptic compound of claim 15 , wherein X is Se.

17. The heteroleptic compound of claim 15 , wherein X is BR.

18. The heteroleptic compound of claim 1 wherein the compound is selected from the group consisting of:

19. The heteroleptic compound of claim 1 , wherein the compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Xia Chuanjun
• Kwong Raymond C
• Layek Suman

Classifications

• C09K2211/185

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

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title