Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9634264-B2
Application number	US-201213673338-A
Country	US
Kind code	B2
Filing date	Nov 9, 2012
Priority date	Nov 9, 2012
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

Novel iridium complexes containing phenylpyridine and pyridyl aza-benzo fused ligands are described. These complexes are useful as light emitters when incorporated into OLEDs.

First claim

The invention claimed is:

1. A compound having the formula Ir(L A ) n (L B ) 3-n , having the structure:

wherein A 1 and A 2 are carbon or nitrogen;
wherein A 6 , A 7 , and A 8 are carbon;
wherein A 5 is nitrogen;
wherein X is O, S, or Se;
wherein R 1 , R 2 , R 3 , and R 4 independently represent mono-, di-, tri-, tetra-substitution, or no substitution;
wherein any adjacent substitutions in R 1 , R 2 , R 3 , and R 4 are optionally linked together to form a ring;
wherein R 1 , R 2 , R 3 , and R 4 are 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; and
wherein n is an integer from 1 to 3.

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

3. The compound of claim 1 , wherein A 1 and A 2 are carbon.

4. The compound of claim 1 , wherein X is O.

5. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, deuterium, alkyl, and combinations thereof.

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

7. The compound of claim 6 , wherein the alkyl is deuterated or partially deuterated.

8. The compound of claim 1 , wherein R 3 is alkyl.

9. The compound of claim 8 , wherein the alkyl is deuterated or partially deuterated.

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

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

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

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

14. A first device comprising a first organic light emitting device, further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula Ir(L A ) n (L B ) 3-n , having the structure:

wherein A 1 and A 2 are carbon or nitrogen;
wherein A 6 , A 7 , and A 8 are carbon;
wherein A 5 is nitrogen;
wherein X is O, S, or Se;
wherein R 1 , R 2 , R 3 , and R 4 independently represent mono-, di-, tri-, tetra-substitution, or no substitution;
wherein any adjacent substitutions in R 1 , R 2 , R 3 , and R 4 are optionally linked together to form a ring;
wherein R 1 , R 2 , R 3 , and R 4 are 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, sulfanyl, sulfonyl, phosphino, and combinations thereof; and
wherein n is an integer from 1 to 3.

15. The first device of claim 14 , wherein the first device is a consumer product.

16. The first device of claim 14 , wherein the first device is an organic light-emitting device.

17. The first device of claim 14 , wherein the first device comprises a lighting panel.

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

19. The first device of claim 12 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

20. The first device of claim 14 , wherein the organic layer further comprises a host.

21. The first device of claim 20 , 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 , and C n H 2n —Ar 1 ;
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.

22. The first device of claim 20 , wherein the host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

23. The first device of claim 20 , wherein the host is selected from the group consisting of:

and combinations thereof.

24. The first device of claim 20 , wherein the host comprises a metal complex.

Assignees

• Universal Display Corp

Inventors

• Beers Scott
• Xia Chuanjun
• Wendt Harvey
• Layek Suman

Classifications

• C09K2211/185

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

• C09K2211/1033

  with oxygen · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title