IP Library › Granted Patent US 9,062,152
Granted Patent B2
US 9,062,152 · App. 13/281,023 · Granted Jun 23, 2015

Organic electronic devices, including organic photovoltaic devices, polymers, and monomers

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Quick Facts
Patent No.
US 9,062,152
App. No.
13/281,023
Granted
Jun 23, 2015
Kind
B2
Abstract

Materials for organic electronic devices including organic photovoltaic devices. An oligomer or polymer comprising: wherein R 1 , R 2 , R 3 , and R 4 are independently hydrogen or solubilizing groups. Monomers and ink compositions can be also prepared. The materials can be used in an OPV active layer and show excellent absorption properties with bathochromic shift.

Claims (33)

1. An oligomer or polymer comprising:

wherein R 1 , R 2 , R 3 , and R 4 are independently hydrogen or solubilizing groups.

2. The oligomer or polymer of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are the same group.

3. The oligomer or polymer of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an aromatic group.

4. The oligomer or polymer of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an arylalkyl group.

5. The oligomer or polymer of claim 1 , wherein it is as polymer having a molecular weight of at least 10,000 number average molecular weight.

6. The oligomer or polymer of claim 1 , wherein the oligomer or polymer is a donor-acceptor oligomer or polymer.

7. The oligomer or polymer of claim 1 , wherein the oligomer or polymer is a donor-acceptor polymer, and has at least two types of donors, or at least two types of acceptors.

8. The oligomer or polymer of claim 1 , wherein the oligomer or polymer is soluble in chloroform, chlorobenzene, dichlorobenzene, or trichlorobenzene.

9. The oligomer or polymer of claim 1 , wherein the oligomer or polymer has a molecular weight of at least 10,000 number average molecular weight and is soluble in chloroform, chlorobenzene, dichlorobenzene, or trichlorobenzene.

10. A coated substrate comprising at least one substrate and at least one coating, wherein the coating comprises at least one polymer according to claim 1 .

11. A monomer comprising a moiety represented by:

wherein R 1 , R 2 , R 3 , and R 4 are independently hydrogen or solubilizing groups.

12. The monomer of claim 11 , wherein R 1 , R 2 , R 3 , and R 4 are the same group.

13. The monomer of claim 11 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an aromatic group.

14. The monomer of claim 11 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an arylalkyl group.

15. The monomer of claim 11 , wherein the monomer is functionalized with electrophilic groups for polymerization.

16. The monomer of claim 11 , wherein the monomer is functionalized with nucleophilic groups for polymerization.

17. The monomer of claim 11 , wherein the monomer is functionalized for Ullman, Yamamoto, or Suzuki polymerization.

18. The monomer of claim 11 , wherein the terminal thiophene rings are functionalized for polymerization.

19. An ink composition comprising at least one oligomer or polymer according to claim 1 and at least one solvent for the oligomer or polymer.

20. The ink composition of claim 19 , wherein the R 1 , R 2 , R 3 , and R 4 are the same group.

21. The ink composition of claim 19 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an aromatic group.

22. The ink composition of claim 19 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an arylalkyl group.

23. The ink composition of claim 19 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and are a C 1 -C 25 group.

24. The ink composition of claim 19 , wherein the solvent comprises at least two solvents, and the ink composition further comprises at least one additive.

25. The ink composition of claim 19 , wherein the solvent comprises a mixture comprising at least orthodichlorobenzene and trichlorobenzene.

26. A OPV device comprising at least one OPV active layer comprising at least one polymer comprising:

wherein R 1 , R 2 , R 3 , and R 4 are independently hydrogen or solubilizing groups.

27. The device of claim 26 , wherein the R 1 , R 2 , R 3 , and R 4 are the same group.

28. The device of claim 26 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an aromatic group.

29. The device of claim 26 , wherein R 1 , R 2 , R 3 , and R 4 are the same group and comprise an arylalkyl group.

30. The device of claim 26 , wherein the polymer is a donor-acceptor polymer.

Assignments (8)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2011
From: GRENIER, CHRISTOPHE RENE GASTON
To: PLEXTRONICS, INC.
Reel/Frame 027383/0954 →