Hole transport compositions and related devices and methods (I)

Patent metadata

Field	Value
Publication number	US-9577194-B2
Application number	US-201113175710-A
Country	US
Kind code	B2
Filing date	Jul 1, 2011
Priority date	Jul 2, 2010
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

A composition comprising: at least one compound comprising a hole transporting core, wherein the core is covalently bonded to a first arylamine group and also covalently bonded to a second arylamine group different from the first, and wherein the compound is covalently bonded to at least one intractability group, wherein the intractability group is covalently bonded to the hole transporting core, the first arylamine group, the second arylamine group, or a combination thereof, and wherein the compound has a molecular weight of about 5,000 g/mole or less. Blended mixtures of arylamine compounds, including fluorene core compounds, can provide good film formation and stability when coated onto hole injection layers. Solution processing of OLEDs is a particularly important application.

First claim

What is claimed is:

1. A composition comprising:
at least one first compound and at least one second compound different from the first,
wherein the at least one first compound comprises a hole transporting core which is a fluorene core or a biphenyl core, wherein the hole transporting core is covalently bonded to a first arylamine group and also covalently bonded to a second arylamine group, and wherein the core is further covalently bonded to at least two solubilizing groups comprising at least four carbon atoms, and wherein the solubilizing groups are optionally substituted with intractability groups;
wherein the at least one second compound comprises a hole transporting core which is a fluorene core or a biphenyl core, wherein the hole transporting core is covalently bonded to a first arylamine group and also covalently bonded to a second arylamine group, wherein the second compound further comprises at least one intractability group which may be bonded to the first arylamine group, the second arylamine group, or both;
wherein the first and second compounds have molecular weight of about 5,000 g/mole or less,
wherein for the first compound, the solubilizing group is substituted with the intractability group, and for the second compound the core further comprises at least two solublizing groups comprising at least four carbon atoms, and
wherein for the second compound the solubilizing groups do not comprise intractability groups.

2. The composition of claim 1 , wherein the relative amounts of the first and second compounds are about 99:1 to about 1:99 by weight, respectively.

3. The composition of claim 1 , wherein the relative amounts of the first and second compounds are about 90:10 to about 10:90 by weight, respectively.

4. The composition of claim 1 , wherein the relative amounts of the first and second compounds are about 20:80 to about 40:60 by weight, respectively.

5. The composition of claim 1 , wherein the relative amounts of the first and second compounds are about 99:1 to about 80:20 by weight, respectively.

6. The composition of claim 1 , wherein the relative amounts of the first and second compounds are about 40:60 to about 60:40 by weight, respectively.

7. The composition of claim 1 , wherein the molecular weight of the first compound is about 2,000 or less, and the molecular weight of the second compound is about 2,000 or less.

8. The composition of claim 1 , wherein the molecular weight of the first compound is about 1,000 or less, and the molecular weight of the second compound is about 1,000 or less.

9. The composition of claim 1 , wherein the first compound has only two arylamine groups, and the second compound has only two arylamine groups.

10. The composition of claim 1 , wherein the hole transporting core for the first and second compounds is the fluorene core, not the biphenyl core, wherein the core fluorene group of the first and second compounds are bonded to the arylamines at the 2 and 7 positions of the fluorene group and the core fluorene group is bonded to the solubilizing groups at the 9 position.

11. The composition of claim 1 , wherein for the first compound the two solubilizing groups each comprise at least eight carbon atoms.

12. The composition of claim 1 , wherein the second compound comprises at least one intractability group which is bonded to the first arylamine group, and at least one intractability group which is bonded to the second arylamine group.

13. The composition of claim 1 , wherein the intractability group for the second compound is vinyl.

14. The composition of claim 1 , wherein the intractability group for the second compound is vinyl which is covalently bonded to a phenyl ring to form a styrene unit.

15. The composition of claim 1 , wherein for the first and second compounds, the first and second arylamine groups are the same group.

16. The composition of claim 1 , wherein the two solubilizing groups bonded to the fluorene core or the biphenyl core are the same groups.

17. The composition of claim 1 , wherein at least one of the arylamine groups of the first or second compound comprises an optionally substituted naphthyl group bonded to nitrogen of the aryl amine group.

18. The composition of claim 1 , wherein at least one of the arylamine groups comprises an both an optionally substituted naphthyl group and an optionally substituted phenyl group bonded to nitrogen.

19. The composition of claim 1 , wherein the first and second compounds have a solubility of at least 5 wt. %.

20. The composition of claim 1 , wherein the intractable groups of the first and second compounds are polymerizable groups.

21. The composition of claim 20 , wherein the relative amounts of the first and second compounds are about 20:80 to about 40:60 by weight, respectively.

22. The composition of claim 1 , wherein the first and second compounds have a solubility of at least 5 wt. % and the intractable groups of the first and second compound are polymerizable groups.

23. The composition of claim 22 , wherein the first compound and the second compound comprise different intractability groups.

24. The composition of claim 1 , wherein the relative amounts of the first and second compounds are about 25:75 to about 35:65 by weight, respectively.

25. The composition of claim 1 , wherein for the first compound the intractability group is benzocyclobutane.

26. The composition of claim 1 , wherein for the second compound the at least two solublizing groups comprise at least eight carbon atoms.

27. The composition of claim 1 , wherein the first compound and the second compound comprise different intractability groups.

28. The composition of claim 1 , wherein the first compound is represented by:

29. The composition of claim 1 , wherein the second compound is represented by:

30. The composition of claim 1 , wherein the first compound is represented by

and the second compound is represented by:

31. The composition of claim 1 , wherein the composition further comprises a solvent system to form an ink.

32. The composition of claim 1 , wherein the composition further comprises a solvent system to form an ink, wherein the solid content of the ink is about 0.5 to about 5 wt/wt % total solids.

33. The composition of claim 1 , wherein the composition further comprises a solvent system to form an ink, and the solvent system comprises toluene, o-xylene, chlorobenze, or mixtures thereof as solvent.

34. The composition of claim 1 , wherein the intractable groups are polymerizable groups, and the polymerizable groups are reacted.

35. A composition prepared by reaction of the first and second compounds of the composition of claim 1 .

36. The composition of claim 1 , wherein the composition further comprises at least one third compound, different from the first and second compounds,

Assignees

• Brown Christopher T
• Chopra Neetu
• Knittel Christopher R
• Mathai Mathew
• Seshadri Venkataramanan
• Wang Jing
• Woodworth Brian
• Nissan Chemical Ind Ltd

Inventors

• Brown Christopher T
• Chopra Neetu
• Knittel Christopher R
• Mathai Mathew
• Seshadri Venkataramanan
• Wang Jing
• Woodworth Brian

Classifications

• C09D11/00

  Inks · CPC title

• C09B69/109

  containing other specific dyes · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• C08G2261/76

  crosslinking · CPC title

• C08G2261/512

  Hole transport · CPC title