Ambipolar small molecule hosts for phosphorescent guest emitters

Patent metadata

Field	Value
Publication number	US-9133177-B2
Application number	US-201013379595-A
Country	US
Kind code	B2
Filing date	Jun 21, 2010
Priority date	Jun 24, 2009
Publication date	Sep 15, 2015
Grant date	Sep 15, 2015

Abstract

The inventions describe disclosed and described herein relate to ambipolar small molecule host materials for guest phosphorescent metal complexes. Methods of making the ambipolar small molecules are also described. These ambipolar small molecules, which comprise both an oxadiazole and one or more carbazole groups, can be used to make the emission layers of unexpectedly efficient OLED devices containing the materials of the inventions, wherein (I) at least one of the R 1 , R 2 and R 3 groups is an optionally substituted carbazole group.

First claim

What is claimed is:

1. A compound comprising an optionally substituted aryl or heteroaryl group bonded to a 1,3,4-oxadiazole group, the compound having the formula:

wherein
a) Ar is a C 5 -C 20 aryl or heteroaryl group optionally comprising one to five substituent groups independently selected from the group consisting of hydrogen, hydroxyl, fluorine, cyano, a C 1 -C 20 alkyl, perfluoroalkyl, alkoxide, and perfluoroalkoxide groups; and
b) at least two of the R 1 , R 2 and R 3 groups is an optionally substituted carbazole group having the structure

wherein R 5 and R 6 are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 6 organic group selected from alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides, and the remaining R 1 , R 2 or R 3 groups are independently selected from the group consisting of hydrogen, fluorine, cyano, or a C 1 -C 20 alkyl, perfluoroalkyl, alkoxide, and perfluoroalkoxide groups; or
one of the R 1 , R 2 , and R 3 groups is an optionally substituted carbazole group having the structure

wherein R 5 , R 5′ , R 6 and R 6′ are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 6 organic group selected from the group consisting of alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides, and the remaining R 1 , R 2 , or R 3 groups are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 6 organic group selected from the group consisting of alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides.

2. The compounds of claim 1 having the structure

wherein R 7 -R 11 are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 20 alkyl, perfluoroalkyl, alkoxide, and perfluoroalkoxide group.

3. The compounds of claim 1 wherein Ar comprises an optionally substituted phenyl, naphthyl, fluorenyl, anthracenyl, pyridyl, bipyridyl, thiophenyl, furanyl, or pyrolyl group.

4. The compounds of claim 1 wherein both the R 1 and R 3 groups have the structure

wherein R 5 and R 6 are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 6 organic group selected from the group consisting of alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides, and R 2 is hydrogen.

5. The compounds of claim 1 wherein one of the R 1 , R 2 , and R 3 is an optionally substituted carbazole group having the structure

wherein R 5 , R 5′ , R 6 and R 6′ are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 6 organic group selected from the group consisting of alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides, and the remaining R 1 , R 2 , or R 3 groups are hydrogen.

6. The compounds of claim 1 having the structure

wherein R 5 , R 5′ , R 6 , R 6′ , and R 12 are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 6 organic group selected from the group consisting of alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides.

7. The compounds of claim 1 having the structure

wherein R 5 , R 5′ , R 6 , R 6′ , and R 12 are independently selected from the group consisting of hydrogen, fluorine, cyano, and C 1 -C 6 organic group selected from the group consisting of alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides.

8. The compounds of claim 1 , wherein R 5 , R 5′ , R 6 , and R 6′ are hydrogen or t-butyl.

9. The compounds of claim 1 having the structure

wherein R 7 -R 11 are independently selected from the group consisting of hydrogen, fluorine, cyano, and a C 1 -C 6 organic group selected from the group consisting of alkyls, perfluoroalkyls, alkoxides, and perfluoroalkoxides.

10. A composition comprising at least one compound of claim 1 .

11. A device comprising at least one compound of claim 1 .

12. The device of claim 11 , wherein the device is a light emitting diode.

13. The device of claim 12 wherein the compound is used as a hole transporting material, an electron transporting material, or both.

14. The device of claim 12 comprising an emission layer comprising the compound of claim 1 as a host material to at least one phosphor.

15. The compound of claim 1 having the structure

Assignees

• Zhang Yadong
• Zuniga Carlos
• Deshayes Gaelle
• Leroy Julie
• Barlow Stephen
• Marder Seth R
• He Xuyang
• Kim Sung-Jin
• Kippelen Bernard
• Georgia Tech Res Inst

Inventors

• Zhang Yadong
• Zuniga Carlos
• Deshayes Gaelle
• Leroy Julie
• Barlow Stephen
• Marder Seth R
• He Xuyang
• Kim Sung-Jin
• Kippelen Bernard

Classifications

• C08G2261/149

  Side-chains having heteroaromatic units · CPC title

• H01L51/004

  Electricity · mapped topic

• H01L51/0043

  Electricity · mapped topic

• C08F120/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C08F12/14

  substituted by hetero atoms or groups containing heteroatoms · CPC title