Deuterated compounds for luminescent applications

Patent metadata

Field	Value
Publication number	US-2016013413-A1
Application number	US-201514854317-A
Country	US
Kind code	A1
Filing date	Sep 15, 2015
Priority date	Dec 22, 2008
Publication date	Jan 14, 2016
Grant date	—

Abstract

This invention relates to deuterated compounds that are useful in electroluminescent applications. It also relates to electronic devices in which the active layer includes such a deuterated compound.

First claim

1 .- 16 . (canceled)

17 . An organic electronic device comprising a first electrical contact layer, a second electrical contact layer, and at least one active layer therebetween, wherein the active layer comprises a compound selected from the group consisting of diarylaminochrysenes, said compound having at least one D.

18 . The device of claim 17 , wherein the compound has Formula II:

wherein:
R 1 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy and aryl, where adjacent R 1 groups may be joined together to form a 5- or 6-membered aliphatic ring;
Ar 1 through Ar 4 are the same or different and are selected from the group consisting of aryl groups; and
b is the same or different at each occurrence and is an integer from 0 to 5;
wherein the compound has at least one D.

19 . The device of claim 18 , wherein R 1 is a deuterated alkyl.

20 . (canceled)

21 . The device of claim 18 having Formula II, wherein b=5 and R 1 is D.

22 . The device of claim 18 , wherein Ar 1 through Ar 4 is selected from the group consisting of naphthyl, phenylnapthyl, naphthylphenyl, binaphthyl, and a compound having Formula III:

where:
R 2 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, aryl, silyl, and siloxane, or adjacent R 2 groups can be joined to form an aromatic ring;
c is the same or different at each occurrence and is an integer from 0-4;
d is the same or different at each occurrence and is an integer from 0-5; and
m is the same or different at each occurrence and is an integer from 0 to 6.

23 . The device of claim 18 , wherein the compound is selected from E3 through E9.

24 . The device of claim 18 , wherein the active layer is an electroactive layer and further comprises a host material.

25 . The device of claim 24 , further comprising a buffer layer between the first electrical contact layer and the active layer.

26 . The device of claim 25 , wherein the buffer layer comprises at least one electrically conductive polymer and at least one fluorinated acid polymer.

27 . The device of claim 17 , wherein the compound has at least 50% deuteration.

28 . The device of claim 18 , wherein the compound has at least one substituent group on an aryl ring, wherein deuteration is on the substituent group on the aryl ring.

29 . The device of claim 18 , wherein at least one of Ar 1 through Ar 4 is a deuterated aryl group.

30 . The device of claim 29 , wherein Ar 1 through Ar 4 are at least 20% deuterated.

31 . The device of claim 18 wherein the compound has at least one substituent on an aryl ring, wherein deuteration is present on both at least one substituent group and at least one aryl ring.

32 . The device of claim 18 , wherein R 1 is a hydrocarbon alkyl.

33 . The device of claim 18 , wherein b=0.

34 . The device of claim 18 , wherein b=5 and R 1 is D.

35 . The device of claim 18 , wherein Ar 1 through Ar 4 are perdeuterated.

Assignees

• Du Pont

Inventors

• Herron Norman
• Rostovtsev Vsevolod
• Merlo Jeffrey A
• Howard Jr Michael Henry
• Fennimore Adam
• Gao Weiying
• Dogra Kalindi
• Radu Nora Sabina
• Wu Weishi
• Smith Eric Maurice
• Lecloux Daniel David

Classifications

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07B59/001 Primary

  Acyclic or carbocyclic compounds · CPC title

• H01L51/5088

  Electricity · mapped topic

• H01L51/006 Primary

  Electricity · mapped topic

• C07C2603/48

  Chrysenes; Hydrogenated chrysenes · CPC title