Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10079349-B2
Application number	US-201213480176-A
Country	US
Kind code	B2
Filing date	May 24, 2012
Priority date	May 27, 2011
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

Abstract

Novel heteroleptic iridium complexes are described. These iridium compounds contain alkyl substituted phenylpyridine ligands, which provide these compounds with beneficial properties when the iridium complexes are incorporated into OLED devices.

First claim

The invention claimed is:

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

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 , are independently selected from the group consisting of hydrogen, deuterium, cycloalkyl, deuterated cycloalkyl, alkyl, and deuterated alkyl;
wherein one or more of the following is true: at least one of R 1 , R 2 , and R 3 is cycloalkyl or deuterated cycloalkyl, (ii) a pair of adjacent R 1 , R 2 , and R 3 are linked together to form a ring, (iii) a pair of adjacent R 4 , R 5 , and R 6 are linked together to form a ring;
and
wherein R and R′ represent mono-, di-, tri- or tetra-substitution and 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.

2. The compound of claim 1 , wherein R 1 is cycloalkyl or deuterated cycloalkyl.

3. The compound of claim 1 , wherein R 2 is cycloalkyl or deuterated cycloalkyl.

4. The compound of claim 1 , wherein R 3 is cycloalkyl or deuterated cycloalkyl.

5. The compound of claim 1 , wherein R 4 is alkyl.

6. The compound of claim 1 , wherein R 5 is alkyl.

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

8. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is cycloalkyl or deuterated cycloalkyl.

9. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is cycloalkyl or deuterated cycloalkyl and at least one of R 4 , R 5 , and R 6 is alkyl.

10. The compound of claim 1 , wherein at least one pair of adjacent R 1 , R 2 , and R 3 is linked together to form a ring.

11. The compound of claim 1 , wherein at least one of R 4 , R 5 , and R 6 is an alkyl that contains at least 3 carbons.

12. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is an cycloalkyl or deuterated cycloalkyl that contains at least 3 carbons and at most 6 carbons.

13. The compound of claim 1 , wherein at least one of R 4 , R 5 , and R 6 is an alkyl that contains greater than 10 carbons.

14. The compound of claim 1 , wherein the compound emits yellow light with a full width at half maximum between about 70 nm to about 110 nm when the light has a peak wavelength between about 530 nm to about 580 nm.

15. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is cycloalkyl or deuterated cycloalkyl.

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

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

18. The compound of claim 1 , wherein the compound has a structure of formula:

19. The compound of claim 1 , wherein the compound has a structure formula:

20. A first device comprising a first organic light emitting device, the 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 2 , R 3 , R 4 , R 5 , and R 6 , are independently selected from the group consisting of hydrogen, deuterium, cycloalkyl, deuterated cycloalkyl, alkyl, and deuterated alkyl;
wherein one or more of the following is true: at least one of R 1 , R 2 , and R 3 is cycloalkyl or deuterated cycloalkyl, (ii) a pair of adjacent R 1 , R 2 , and R 3 are linked together to form a ring, (iii) a pair of adjacent R 4 , R 5 , and R 6 are linked together to form a ring;
and
wherein R and R′ represent mono-, di-, tri- or tetra-substitution and 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.

21. The first device of claim 20 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.

22. The first device of claim 20 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

23. The first device of claim 20 , wherein the emissive layer comprises a host, and 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.

24. The first device of claim 23 , wherein the host has the formula:

25. The first device of claim 20 , wherein the emissive layer comprises a host, and the host is a metal complex.

26. The first device of claim 20 wherein the first device is selected from the group consisting of a consumer product, an organic light-emitting device, and a lighting panel.

27. The first device of claim 20 , wherein the first device further comprises a second emissive dopant having a peak wavelength of between 400 to 500 nanometers.

28. The first device of claim 27 , wherein the second emissive dopant is a fluorescent emitter.

29. The first device of claim 27 , wherein the second emissive dopant is a phosphorescent emitter.

30. The first device of claim 20 , wherein the first device further comprises a first organic light-emitting device comprising a compound of Formula I and a second light emitting

Assignees

• Tsai Jui Yi
• Xia Chuanjun
• Kottas Gregg
• Elshenaway Zeinab
• Ansari Nasrin
• Alleyne Bert
• Universal Display Corp

Inventors

• Tsai Jui-Yi
• Xia Chuanjun
• Kottas Gregg
• Elshenaway Zeinab
• Ansari Nasrin
• Alleyne Bert

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · 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

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title