IP Library Granted Patent US 7,569,159
Granted Patent B2
US 7,569,159 · App. 11/350,271 · Granted Aug 4, 2009

Hole injection/transport layer compositions and devices

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Quick Facts
Patent No.
US 7,569,159
App. No.
11/350,271
Granted
Aug 4, 2009
Kind
B2
Abstract

Compositions for use in HIL/HTL applications include intrinsically conductive polymer, planarizing agent, and dopant, which are soluble in non-aqueous solvents. Block copolymers of regioregular alkyl/alkoxy- and aryl-substituted polythiophenes can be used. The compositions can be formed into thin films. Excellent efficiency and lifetime stability can be achieved.

Claims (50)

1. A blend composition for use in a hole injection layer or hole transport layer comprising the following components:

(i) at least one intrinsically conductive polymer or copolymer,

(ii) at least one dopant for the conductive polymer or copolymer; and

(iii) at least one planarizing agent, wherein the planarizing agent is a synthetic polymer;

wherein the components are soluble in non-aqueous solvents and are formulated to form a compatible blend when the composition is in the form of a hole injection layer or hole transport layer less than about 200 nm thick, wherein the intrinsically conductive polymer or copolymer is a regioregular 3-substituted polythiophene.

2. The composition according to claim 1 , wherein the intrinsically conductive polymer or copolymer is a homopolymer.

3. The composition according to claim 1 , wherein the intrinsically conductive polymer or copolymer is a copolymer.

4. The composition according to claim 1 , wherein the intrinsically conductive polymer or copolymer is a block copolymer.

5. The composition according to claim 1 , wherein the intrinsically conductive polymer or copolymer is a regioregular alkyl/alkoxy-, etheric, poly(etheric), or aryl-substituted polythiophene block copolymer comprising a polythiophene block and a non-polythiophene block.

6. The composition according to claim 1 , wherein the intrinsically conductive polymer or copolymer is a regioregular alkyl/alkoxy-, etheric, poly(etheric), or aryl-substituted polythiophene block copolymer comprising a polythiophene block and a non-polythiophene block, and the non-polythiophene block is substantially similar to the planarizing agent.

7. The blend composition according to claim 1 , wherein the layer is less than about 100 nm thick.

8. The composition according to claim 1 , wherein the composition is in the form of a film about 2 nm to about 100 nm thick.

9. The composition according to claim 1 , wherein the amounts of the intrinsically conductive polymer or copolymer, and the planarizing agent are about 0.5 wt % to about 25 wt %, and about 0.5 wt % to about 70 wt %, respectively.

10. The composition according to claim 1 , wherein the amounts of the intrinsically conductive polymer or copolymer, and the planarizing agent are about 0.5 wt % to about 25 wt %, and about 0.5 wt % to about 80 wt %, respectively.

11. The composition according to claim 1 , wherein the planarizing agent is an organic polymer.

12. The composition according to claim 1 , wherein the dopant comprises organic oxidant.

13. The composition according to claim 1 , wherein the dopant is an acid dopant.

14. The composition according to claim 1 , wherein the dopant comprises organic oxidant, the planarizing agent is an organic polymer, the polymer or copolymer comprises regioregular polythiophene, and the amounts of the intrinsically conductive polymer or copolymer, and the planarizing agent are about 0.5 wt % to about 25 wt %, and about 0.5 wt % to about 70 wt %, respectively.

15. The composition according to claim 1 , wherein the dopant comprises organic oxidant, the planarizing agent is an organic polymer, and the amounts of the intrinsically conductive polymer or copolymer, and the planarizing agent are about 0.5 wt % to about 25 wt %, and about 0.5 wt % to about 80 wt %, respectively.

16. An electroluminescent (EL) device comprising an anode, a cathode, and a hole injection layer or a hole transport layer, wherein the hole injection layer or hole transport layer comprises a blend composition according to claim 1 .

17. A method comprising the step of ink jet printing the composition according to claim 1 , wherein the composition further comprises organic solvent.

18. An electroluminescent device comprising a hole injection layer or hole transport layer comprising the following components:

(i) at least one intrinsically conductive polymer or copolymer soluble in non-aqueous solvent, and wherein the intrinsically conductive polymer or copolymer is a regioregular 3-substituted polythiophene,

(ii) at least one dopant for the conductive polymer or copolymer; and

(iii) at least one planarizing agent, wherein the planarizing agent is a synthetic polymer soluble in non-aqueous solvent;

wherein the hole injection layer or hole transport layer is less than about 200 nm thick.

19. The device according to claim 18 , wherein conductive polymer or copolymer is a homopolymer.

20. The device according to claim 18 , wherein conductive polymer or copolymer is a copolymer.

21. The device according claim 18 , wherein the intrinsically conductive polymer or copolymer is a regioregular alkyl/alkoxy-, etheric, poly(etheric), or aryl-substituted polythiophene block copolymer comprising a polythiophene block and a non-polythiophene block.

22. The device according to claim 18 , wherein the intrinsically conductive polymer or copolymer is a regioregular alkyl/alkoxy-, etheric, poly(etheric), or aryl-substituted polythiophene block copolymer comprising a polythiophene block and a non-polythiophene block, and the non-polythiophene block is substantially similar to the planarizing agent.

23. The device according to claim 18 , wherein the hole injection layer or hole transport layer is about 2 nm to about 100 m thick.

24. The device according to claim 18 , wherein the amounts of the intrinsically conductive polymer or copolymer, and the planarizing agent are about 0.5 wt % to about 25 wt %, and about 0.5 wt % to about 80 wt %, respectively.

25. The device according to claim 18 , wherein the planarizing agent is an organic polymer.

26. The device according to claim 18 , wherein the dopant comprises organic oxidant.

27. The device according to claim 18 , wherein the dopant is an acid dopant.

28. The device according to claim 18 , wherein the dopant comprises organic oxidant, the planarizing agent is an organic polymer, the polymer or copolymer comprises regioregular polythiophene, and the amounts of the intrinsically conductive polymer or copolymer, and the planarizing agent are about 0.5 wt % to about 25 wt %, and about 0.5 wt % to about 70 wt %, respectively.

29. The device according to claim 18 , wherein the dopant comprises organic oxidant, the planarizing agent is an organic polymer, and the amounts of the intrinsically conductive polymer or copolymer, and the planarizing agent are about 0.5 wt % to about 25 wt %, and about 0.5 wt % to about 80 wt %, respectively.

30. An electroluminescent device comprising a hole injection layer or hole transport layer comprising the following components:

(i) at least one intrinsically conductive polymer or copolymer, wherein the intrinsically conductive polymer or copolymer is a regioregular 3-substituted polythiophene soluble in non-aqueous solvent;

(ii) at least one dopant for the conductive polymer or copolymer; and

(iii) at least one synthetic polymer soluble in non-aqueous solvent; wherein the hole injection layer or hole transport layer is less than about 200 nm thick.

31. The device according to claim 30 , wherein the dopant is an organic dopant.

32. An ink formulation for hole injection layer or hole transport layer application comprising:

about 0.5 wt. % to about 25 wt. % soluble regioregular 3substituted polythiophene soluble in organic solvent,

about 0.5 wt. % to about 70 wt. % organic polymer soluble in organic solvent, organic oxidant dopant, and

organic solvent.

33. An ink formulation for hole injection layer or hole transport layer application comprising:

about 0.5 wt. % to about 25 wt. % soluble regioregular 3substituted polythiophene soluble in organic solvent,

about 0.5 wt. % to about 80 wt. % organic polymer soluble in organic solvent, organic oxidant dopant, and

organic solvent.

Assignments (13)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: SOLVAY USA, INC.
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 039767/0225 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2014
From: PLEXTRONICS, INC.
To: SOLVAY USA INC.
Reel/Frame 032568/0780 →
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 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0742 →
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 →
RELEASE Recorded Mar 11, 2008
From: SILICON VALLEY BANK
To: PLEXTRONICS, INC.
Reel/Frame 020668/0884 →
SECURITY AGREEMENT Recorded May 23, 2007
From: PLEXTRONICS, INC.
To: SILICON VALLEY BANK
Reel/Frame 019330/0001 →
RE-RECORD TO CORRECT THE EXECUTION DATES OF THE ASSIGNORS, PREVIOUSLY RECORDED ON REEL 017509 FRAME 0778. Recorded Oct 19, 2006
From: HAMMOND, TROY D.; WILLIAMS, SHAWN P.; SHEINA, ELENA; LAIRD, DARIN W.; GRECO, CHRISTOPHER; WOODWORTH, BRIAN
To: PLEXTRONICS, INC.
Reel/Frame 018419/0496 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2006
From: HAMMOND, TROY D.; WILLIAMS, SHAWN P.; SHEINA, ELENA; LAIRD, DARIN W.; HANNAH, ANDREW W.; JIA, SHIJUN
To: PLEXTRONICS, INC.
Reel/Frame 017509/0778 →