Forming of optoelectronic devices, particularly of inverted-type OPV cells

Patent metadata

Field	Value
Publication number	US-9559304-B2
Application number	US-201314107296-A
Country	US
Kind code	B2
Filing date	Dec 16, 2013
Priority date	Jan 31, 2013
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

This forming involves a composition including: poly(3,4-ethylenedioxythiophene) or PEDOT; polystyrene sulfonate or PSS; a compound (A) having formula:

with 0<x/y<1; Ar1 and Ar2 representing two aromatic rings, which may be identical or different; Ar1 and/or Ar2 comprising at least one hydrophobic substituent on its ring.

First claim

The invention claimed is:

1. An ink composition comprising:
poly(3,4-ethylenedioxythiophene) (PEDOT);
polystyrene sulfonate (PSS); and
a compound (A) having formula:

with
0<x/y<1,
Ar1 and Ar2 representing aromatic rings, which may be identical or different,
Ar1 and/or Ar2 comprising at least one hydrophobic substituent on its ring, the compound (A) being from 0.01 to 0.2% by weight of the ink composition.

2. The ink composition of claim 1 wherein the compound (A) is electrically conductive or electrically semiconductive.

3. The ink composition of claim 1 , wherein each aromatic ring (Ar 1, Ar2) is selected from the group consisting of thiophene, bithiophene, terthiophene, thienothiophene, pyrrole, carbazole, diketopyrrolopyrrole (DPP), selenophene, cyclopentadithiophene (CPDT), dithieno cyclopentadithiophene, Si-cyclopentadithiophene (Si-CPDT), dithieno Si-cyclopentadithiophene, fluorene, dithienofluorene, benzene, benzothiazole, benzothiadiazole, dithienobenzothiadiazole, quinoxaline, thiazole, and phosphole.

4. The ink composition of claim 3 , wherein aromatic rings Ar1 and Ar2 are thiophenes.

5. The ink composition of claim 1 , wherein the hydrophobic substituent is an ether chain (—O—R), where R may be a linear or branched chain, comprising carbon atoms.

6. The ink composition of claim 5 , wherein Ar1 and/or Ar2, comprise a hydrophobic substituent having the following structure:

7. The ink composition of claim 5 , wherein the carbon atoms number from 1 to 15.

8. The ink composition of claim 5 , wherein R comprises heteroatoms.

9. The ink composition of claim 8 , wherein the heteroatoms are 0 or N.

10. The ink composition of claim 8 , wherein the heteroatoms number from 1 to 10.

11. The ink composition of claim 1 , wherein the compound (A) has the following formula:

12. The ink composition of claim 1 , wherein the ink composition further comprises at least one solvent selected from the group consisting of water, propan-2-ol, Ethylene glycol monobutyl ether (EGMBE), ethanol, butan-1-ol, butan-2-ol, ethylene glycol, propylene glycol, diethylene glycol, Dipropylene Glycol Methyl Ether, and ethylene glycol methyl ether.

13. The ink composition of claim 12 , wherein the ink composition comprises water, propan-2-ol, and 2-butoxyethanol.

14. The ink composition of claim 13 , wherein the water is in a proportion by volume smaller than 5%.

15. The ink composition of claim 13 , wherein the water is in a proportion by volume smaller than 2%.

16. The ink composition of claim 13 , wherein the propan-2-ol is in a proportion by volume greater than 30%.

17. The ink composition of claim 13 , wherein the propan-2-ol is in a proportion by volume between 40% and 60%.

18. The ink composition of claim 13 , wherein the propan-2-ol is in a proportion by volume between 50% and 55%.

19. The ink composition of claim 13 , wherein the 2-butoxyethanol is in a proportion by volume between 10% and 50%.

20. The ink composition of claim 13 , wherein the 2-butoxyethanol is in a proportion by volume between 15% and 35%.

21. The ink composition of claim 1 , wherein the compound (A) amounts to from 0.05 to 0.2% by weight of the ink composition.

22. The ink composition of claim 1 , wherein the compound (A) amounts to 0.1% by weight of the ink composition or more.

23. The ink composition of claim 1 , wherein the poly(3,4-ethylenedioxythiophene) (PEDOT), and the polystyrene sulfonate (PSS) together are more than 1.0% by weight of the ink composition.

24. A method for preparing the composition of claim 1 , comprising mixing the compound (A) in a dispersion containing PEDOT:PSS.

25. A method of forming an optoelectronic device, comprising the deposition on a layer of the composition of claim 1 .

26. The method of forming an optoelectronic device of claim 25 , wherein the deposition is performed by inkjet printing.

27. The method of forming a photovoltaic device of claim 26 , wherein the upper electrode, is deposited at the surface of the layer.

28. The method of forming a photovoltaic device of claim 25 , wherein the upper electrode, is deposited at the surface of the layer.

29. An ink composition consisting of:
poly(3,4-ethylenedioxythiophene) (PEDOT);
polystyrene sulfonate (PSS);
at least one solvent selected from the group consisting of water, propan-2-ol, ethylene glycol monobutyl ether (EGMBE), ethanol, butan-1-ol, butan-2-ol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol methyl ether, and ethylene glycol methyl ether; and
a compound (A) having formula:

with
0<x/y<1,
Ar1 and Ar2 representing aromatic rings, which may be identical or different,
Ar1 and/or Ar2 comprising at least one hydrophobic substituent on its ring,
the compound (A) being from 0.01 to 0.2% by weight of the ink composition.

30. The ink composition of claim 29 , wherein the ink composition further comprises at least one additive selected from the group consisting of a solvent of high boiling point, a crosslinking agent, and a surfactant agent.

31. The ink composition of claim 30 , wherein the solvent comprises an N-Methyl-2-pyrrolidone.

32. The ink composition of claim 30 , wherein the crosslinking agent comprises gamma-glycidoxypropyltimethoxysilane.

33. The ink composition of claim 30 , wherein the surfactant agent comprises an additive containing acetylenic diol.

Assignees

• Commissariat Energie Atomique

Inventors

• Senghor Mathieu
• Berson Solenn
• Manceau Matthieu

Classifications

• C08G2261/91

  Photovoltaic applications · CPC title

• C08G2261/1452

  containing sulfonyl or sulfonate-groups · CPC title

• C08G2261/1424

  containing ether groups, including alkoxy · CPC title

• C08G2261/3223

  containing one or more sulfur atoms as the only heteroatom, e.g. thiophene · CPC title

• H10K71/135

  using ink-jet printing · CPC title