Phosphorescent heteroleptic phenylbenzimidazole dopants

Patent metadata

Field	Value
Publication number	US-9212197-B2
Application number	US-201113111490-A
Country	US
Kind code	B2
Filing date	May 19, 2011
Priority date	May 19, 2011
Publication date	Dec 15, 2015
Grant date	Dec 15, 2015

Abstract

Novel phosphorescent heteroleptic iridium complexes with benzimidazole and phenylpyridine ligands are provided. These iridium complexes can improve OLED properties, and are useful in white light applications.

First claim

The invention claimed is:

1. A compound comprising a heteroleptic iridium complex having the formula:

wherein R 1 , R 3 , R 4 , R 5 , and R 6 represent mono-, di-, tri- or tetra-substitution;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R 1 , R 3 , R 4 , R 5 , and R 6 are optionally fused and may be further substituted;
wherein (1) R 6 is alkyl or heteroalkyl at a position para to a pyridine bonded to iridium, or (2) R 6 is fused and, optionally, further substituted, or (3) both conditions (1) and (2) are satisfied; and
wherein n=1 or 2.

2. The compound of claim 1 , wherein n=2.

3. The compound of claim 1 , wherein n=1.

4. The compound of claim 1 , wherein R 2 is aryl or substituted aryl.

5. The compound of claim 4 , wherein R 2 is a 2,6-disubstituted aryl.

6. The compound of claim 5 , wherein R 2 is

7. The compound of claim 1 , wherein R 2 is alkyl.

8. The compound of claim 1 , wherein R 3 , R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and alkyl, and wherein at least one of R 3 , R 4 , R 5 and R 6 is alkyl.

9. The compound of claim 1 , wherein R 5 is aryl.

10. The compound of claim 1 , wherein R 6 is fused to form a naphthyl or aza-naphthyl ring system.

11. The compound of claim 1 , wherein R 1 , R 3 , and R 5 are hydrogen.

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

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

wherein R 1 , R 3 , R 4 , R 5 , and R 6 represent mono-, di-, tri- or tetra-substitution;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R 1 , R 3 , R 4 , R 5 , and R 6 are optionally fused and may be further substituted;
wherein (1) R 6 is alkyl or heteroalkyl at a position para to a pyridine bonded to iridium, or (2) R 6 is fused and, optionally, further substituted, or (3) both conditions (1) and (2) are satisfied; and
wherein n=1 or 2.

14. The first device of claim 13 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.

15. The first device of claim 13 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

16. The first device of claim 13 , wherein the organic layer further comprises a host.

17. The first device of claim 16 , wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , C n H 2n —Ar 1 , or no substitution;
wherein n is from 1 to 10; and
wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

18. The first device of claim 17 , wherein the host has the formula:

19. The first device of claim 16 , wherein the host is a metal complex.

20. The first device of claim 13 wherein the first device is a consumer product.

21. The first device of claim 13 , wherein the first device is an organic light-emitting device.

22. The first device of claim 13 , wherein the first device further comprises a second emissive dopant having a peak wavelength of between 400 to 500 nanometers.

23. The first device of claim 22 , wherein the second emissive dopant is a fluorescent emitter.

24. The first device of claim 22 , wherein the second emissive dopant is a phosphorescent emitter.

25. The first device of claim 13 , wherein the first device comprises a lighting panel.

26. The first device of claim 13 , wherein the first device further comprises a first organic light-emitting device comprising a compound of Formula I and a second light emitting device separate from the first organic light-emitting device comprising an emissive dopant having a peak wavelength of between 400 to 500 nanometers.

27. The first device of claim 13 , wherein the first device comprises an organic-light emitting device having a first emissive layer and a second emissive layer;
wherein the first emissive layer comprises a compound

Assignees

• Kottas Gregg
• Xia Chuanjun
• Elshenawy Zeinab
• Ansari Nasrin
• Universal Display Corp

Inventors

• Kottas Gregg
• Xia Chuanjun
• Elshenawy Zeinab
• Ansari Nasrin

Classifications

• C09K2211/185

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

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H01L51/0085

  Electricity · mapped topic

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• H01L51/5016

  Electricity · mapped topic