IP Library Granted Patent US 8,187,501
Granted Patent B2
US 8,187,501 · App. 12/395,327 · Granted May 29, 2012

Planarizing agents and devices

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Quick Facts
Patent No.
US 8,187,501
App. No.
12/395,327
Granted
May 29, 2012
Kind
B2
Abstract

Use of certain materials in hole injection layer and/or hole transport layer can improve operational lifetimes in organic devices. Polymers having fused aromatic side groups such as polyvinylnaphthol polymers can be used in conjunction with conjugated polymers. Inks can be formulated and cast as films in organic electronic devices including OLEDs, SMOLEDs, and PLEDs. One embodiment provides a composition comprising: at least one conjugated polymer, and at least one second polymer different from the conjugated polymer comprising at least one optionally substituted fused aromatic hydrocarbon side group. The substituent can be hydroxyl. Aqueous-based inks can be formulated.

Claims (55)

1. A composition comprising:

at least one conjugated polymer, and

at least one second polymer different from the conjugated polymer comprising at least one fused aromatic hydrocarbon side group substituted with at least one hydroxyl.

2. The composition of claim 1 , wherein the fused aromatic hydrocarbon side group is a naphthalene group.

3. The composition of claim 1 , wherein the second polymer comprises a carbon backbone and the optionally substituted fused aromatic hydrocarbon side group comprises two fused benzene rings.

4. The composition of claim 1 wherein the second polymer provides a decreased singlet and/or triplet excited state energy.

5. The composition of claim 1 wherein the second polymer is an excited state stabilizer.

6. The composition of claim 1 wherein the second polymer has a number average molecular weight between about 5,000 and about 100,000 g/mol.

7. The composition of claim 1 , wherein the first and second polymers are soluble or dispersible in water.

8. The composition of claim 1 wherein the conjugated polymer is a heterocyclic polymer.

9. The composition of claim 1 wherein the conjugated polymer comprises a polythiophene backbone.

10. The composition of claim 1 wherein the conjugated polymer is self-doped.

11. The composition of claim 1 wherein the conjugated polymer is sulfonated poly(3-(methoxyethoxyethoxy)thiophene-2,5-diyl) and the second polymer is poly-2-vinylnaphthol.

12. The composition of claim 1 wherein the amount of the conjugated polymer and the amount of the second polymer are adapted for use of the composition as a hole injection layer or a hole transport layer in an electronic device.

13. The composition of claim 1 comprising between about 1 wt. % and 30 wt. % of the conjugated polymer and between about 70 wt. % and 99 wt. % of the second polymer.

14. The composition of claim 1 comprising between about 10 wt. % and 20 wt.

15. The composition of claim 1 , the composition further comprising a dopant.

16. The composition of claim 1 further comprising a dopant, wherein the dopant is an anionic polymer.

17. The composition of claim 1 further comprising at least one carrier solvent.

18. The composition of claim 1 further comprising at least one carrier solvent and wherein water is the primary solvent present in the most amount.

19. The composition of claim 1 , wherein the first and second polymers are soluble polymers, the first polymer is a sulfonated polythiophene, and the second polymer is a poly(vinyl naphthol).

20. The composition of claim 1 , wherein the first and second polymers are soluble polymers, the first polymer is a sulfonated polythiophene comprising ether substituents, and the second polymer is a poly(vinyl naphthol).

21. The composition of claim 1 , wherein the first and second polymers are soluble polymers, the first polymer is a sulfonated regioregular polythiophene comprising ether substituents, and the second polymer comprises at least one repeat unit represented by:

wherein R is a polar functional group, and wherein the amount of the conjugated polymer and the amount of the second polymer are adapted for use of the composition as a hole injection layer or a hole transport layer in an electronic device.

22. The composition of claim 1 , wherein the at least one second polymer comprises at least one repeat unit represented by:

wherein R is a polar functional group, and wherein the amount of the conjugated polymer and the amount of the second polymer are adapted for use of the composition as a hole injection layer or a hole transport layer in an electronic device.

23. The composition of claim 1 , further comprising a solvent carrier for the conjugated polymer and the second polymer, wherein the composition is formulated for use as a hole injection or hole transport layer in an organic device.

24. A device comprising a layer comprising the composition of claim 1 .

25. The device of claim 24 , wherein the layer is a hole injection layer or a hole transport layer.

26. The device of claim 24 , wherein the device is an OLED device.

27. A method of making a device comprising:

providing a substrate;

layering a transparent conductor on the substrate;

layering the composition of claim 1 on the transparent conductor to form a hole injection layer or hole transport layer;

layering an active layer on the hole injection layer or hole transport layer; and

layering a cathode on the active layer.

28. A method comprising: applying the composition of claim 1 , as part of an HIL or HTL layer in an OLED, a photovoltaic device, an ESD, a SMOLED, a PLED, a sensor, a supercapacitor, a cation transducer, a drug release device, an electrochromic device, a transistor, a field effect transistor, an electrode modifier, an electrode modifier for an organic field transistor, an actuator, or a transparent electrode.

29. The composition of claim 1 , wherein the second polymer is a copolymer.

30. The composition of claim 1 , wherein the second polymer is a block copolymer.

31. The composition of claim 1 , wherein the conjugated polymer comprises sulfonated polythiophene.

32. The composition of claim 1 , wherein the conjugated polymer comprises regioregular polythiophene.

33. The composition of claim 1 , wherein the conjugated polymer comprises derivatized polythiophene, wherein the derivative comprises at least one etheric side group.

34. A composition comprising:

at least one conjugated polymer;

at least one second polymer different from the conjugated polymer comprising at least one optionally substituted fused aromatic hydrocarbon side group; and

wherein the conjugated polymer comprises a sulfonated polythiophene.

35. A composition comprising:

at least one conjugated polymer;

at least one second polymer different from the conjugated polymer comprising at least one optionally substituted fused aromatic hydrocarbon side group; and

wherein the conjugated polymer comprises regioregular polythiophene.

36. The composition of claim 35 wherein the conjugated polymer comprises regioregular polythiophene, wherein the degree of regioregularity is greater than about 75% regioregular.

37. A composition comprising:

at least one conjugated polymer;

at least one second polymer different from the conjugated polymer comprising at least one optionally substituted fused aromatic hydrocarbon side group; and

wherein the conjugated polymer comprises derivatized polythiophene, wherein the derivative comprises at least one etheric side group.

Assignments (10)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: SOLVAY USA, INC.
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 039767/0225 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0742 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0619 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0641 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2014
From: PLEXTRONICS, INC.
To: SOLVAY USA INC.
Reel/Frame 032568/0780 →
SECURITY AGREEMENT Recorded Jan 30, 2014
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 032141/0680 →
SECURITY AGREETMENT Recorded Sep 23, 2013
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 031347/0336 →
SECURITY AGREEMENT Recorded May 24, 2013
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 030486/0137 →
SECURITY AGREEMENT Recorded Sep 2, 2011
From: PLEXTRONICS, INC.
To: SOLVAY NORTH AMERICA INVESTMENTS, LLC
Reel/Frame 026849/0711 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2009
From: BROWN, CHRISTOPHER T.; SESHADRI, VENKATARAMANAN
To: PLEXTRONICS, INC.
Reel/Frame 022823/0241 →