Compositions produced by solvent exchange methods and uses thereof

• US 20040258952A1
• Filed: 12/22/2003
• Published: 12/23/2004
• Est. Priority Date: 02/16/2001
• Status: Abandoned Application

• Current Assignee: Elecon Incorporated
• Original Assignee: Elecon Incorporated
• Inventors: Schuler, Peter, Vinciguerra, Michael A., Ryu, Jae, Mojazza, Hamid R., Haghighat, R. Ross
• Application Number:
  US10/744,671
• Publication Number:
  US 20040258952A1
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C08G 61/126 with a five-membered ring containing one sulfur atom in the ring
• CPC Class Codes: C08G 73/1039 comprising halogen-containing substituents
• CPC Class Codes: C08G 73/1057 Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
• CPC Class Codes: C09D 165/00 Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C09D107/00 - C09D157/00, C09D161/00 take precedence; Coating compositions based on derivatives of such polymers
• CPC Class Codes: H01G 11/48 Conductive polymers
• CPC Class Codes: H01G 11/56 Solid electrolytes, e.g. gels; Additives therein
• CPC Class Codes: H01G 9/028 Organic semiconducting electrolytes, e.g. TCNQ
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y02E 60/13 Energy storage using capacitors
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

Disclosed are compositions formed by a method for exchanging solvent in a mixture that includes water and an optionally substituted thiophene. Also disclosed are methods for making and using such compositions.

Claims

1. A composition comprising:

a combination of an aqueous dispersion of an optionally substituted poly-3,4 alkylene dioxythiophene cation and an associated polyanion; and

1% (w/v) to 100% (w/v) of one or more organic solvents, wherein the one or more organic solvents have a boiling point between from about 80°

C. to about 290°

C., wherein at least 30% (w/v) of the water from the aqueous dispersion is removed from said combination.

2. The composition of claim 1, wherein at least 90% of the water from the aqueous dispersion is removed.

3. The composition of claim 1, wherein the polyanion is polystyrene sulfonic acid (PSS).

4. The composition of claim 1, wherein the aqueous dispersion of said optionally substituted poly-3,4-alkylene dioxythiophene includes an aqueous dispersion of 0.5-5% by weight of poly-3,4-ethylene dioxythiophene and the anion is polystyrene sulfonic acid.

5. The composition of claim 1 further comprising at least one additive.

6. The composition of claim 5, wherein the additive is a binder.

7. The composition of claim 5, wherein the additive is ferric toluene sulfonic acid.

8. The composition of claim 7, wherein the ferric toluene sulfonic acid is present in trace amounts.

9. The composition of claim 1, wherein a coating of the composition has at least an order of magnitude higher conductivity than a coating of the corresponding unexchanged optionally substituted poly-3,4-alkylene dioxythiophene aqueous dispersion.

10. The composition of claim 1 wherein the aqueous dispersion of said optionally substituted poly-3,4-alkylene dioxythiophene includes an aqueous dispersion of 0.5-5% by weight of poly-3,4-ethylene dioxythiophene and the anion is polystyrene sulfonic acid.

11. The composition of claim 1 the aqueous dispersion of the optionally substituted poly-3,4-alkylene dioxythiophene cation and an associated polyanion is from about 0.38% to about 1.55% by weight of said composition.

12. The composition of claim 1 wherein the one or more organic solvents include lower alkyl acetamides, lower alcohols, diol alcohols, triol alcohols, pyrrolidones, lower alkyl pyrrolidones, higher alkyl pyrrolidones, lower alkyl sulfoxides, or mixtures thereof.

13. The composition of claim 1, wherein the one or more organic solvent is glycol or glycerin.

14. The composition of claim 1, wherein the one or more organic solvents is dimethylsulfoxide.

15. The composition of claim 1, wherein the one or more organic solvents is a mixture of ethylene glycol and N-methylpyrrolidone.

16. The composition of claim 1, wherein the one or more organic solvents is a mixture of ethylene glycol, dimethylacetamide, and N-methylphyrrolidone.

17. The composition of claim 1, wherein the polyanion is an anion of a polymeric carboxylic acid, a polymaleic acid, a polymeric sulphonic acid, or mixtures thereof.

18. The composition of claim 1, wherein the one or more organic solvents have a boiling point between from about 100°

C. to about 250°

C.

19. A coating comprising a composition comprising:

a combination of an aqueous dispersion of an optionally substituted poly-3,4 alkylene dioxythiophene cation and an associated polyanion; and

1% (w/v) to 100% (w/v) of one or more organic solvents that include ethylene glycol, dimethylacetamide, N-methylpyrrolidone, or mixtures thereof, wherein at least 30% (w/v)of the water from the aqueous dispersion is removed from said combination.

20. The coating of claim 19, wherein at least 90% of the water from the aqueous dispersion is removed.

21. The coating of claim 19, wherein the polyanion is polystyrene sulfonic acid (PSS).

22. The coating of claim 19, wherein the aqueous dispersion of said optionally substituted poly-3,4-alkylene dioxythiophene includes an aqueous dispersion of 0.5-5% by weight of poly-3,4-ethylene dioxythiophene and the anion is polystyrene sulfonic acid.

23. The coating of claim 19, further comprising at least one additive.

24. The coating of claim 23, wherein the additive is a binder.

25. The coating of claim 23, wherein the additive is ferric toluene sulfonic acid.

26. The coating of claim 25, wherein the ferric toluene sulfonic acid is present in trace amounts.

27. The coating of claim 19, wherein the aqueous dispersion of said optionally substituted poly-3,4-alkylene dioxythiophene includes an aqueous dispersion of 0.5-5% by weight of poly-3,4-ethylene dioxythiophene and the anion is polystyrene sulfonic acid.

28. The coating of claim 19, the aqueous dispersion of the optionally substituted poly-3,4-alkylene dioxythiophene cation and an associated polyanion is from about 0.38% to about 1.55% by weight of said composition.

29. The coating of claim 19, wherein the one or more organic solvents has a boiling point of about 100°

C. to 250°

C.

30. The coating of claim 19, wherein the one or more organic solvents is a mixture of ethylene glycol and N-methylpyrrolidone.

31. The coating of claim 19, wherein the polyanion is an anion of a polymeric carboxylic acid, a polymaleic acid, a polymeric sulphonic acid, or mixtures thereof.

32. The coating of claim 19, wherein the coating is configured as a layer.

33. The coating of claim 32, wherein the layer has a surface resistance of between from about 10 to about 10¹² Ω

/sq.

34. The coating of claim 32 having between from about 1 mg/m² to about 500 mg/m² of the composition in the layer.

35. The coating of claim 32 in which the layer has an optical density of between from about 0.0001 to about 0.05 at between from about 300 nm to about 700 nm.

36. The coating of claim 32, wherein the layer has a light transmission of between from about 10% to about 99% as measured by a BYK Gardner Hazegard plus machine.

37. The coating of claim 32, wherein the layer has a light transmission of between from about 80% to about 95% as measured by a BYK Gardner Hazegard plus machine.

38. A coating of claim 19 further comprising least one polymer, co-polymer, graft polymer, or blend thereof.

39. The coating of claim 38, comprising a polymer, wherein the weight ratio of the composition to the polymer is about 10:

90 to about 0.1;

99.9.

40. The coating of claim 38, comprising a polymer, wherein the weight ratio of the composition to the polymer is about 6:

94 to about 0.5;

99.5.

41. The coating of claim 38, comprising a polymer, wherein the polymer is a polyimide.

42. The coating of claim 19, wherein the aqueous dispersion is 0.5-5% by weight of poly-3,4-ethylene dioxythiophene.

43. The coating of claim 19, wherein the coating exhibits a charge carrier mobility of greater than 0.1 Cm²/V-S.

44. The coating of claim 19, wherein the coating is prepared by employing non-vacuum, coating processes, wherein the coating exhibits a charge carrier mobility of greater than 1 Cm²/V-S.

45. The coating of claim 19, wherein the coating exhibits a charger carrier mobility of greater than 10 Cm²/V-S, wherein the charge carrier mobility is measured by the combination of van der Pauw and Hall effect methods.

46. A coating comprising a composition comprising:

a combination of an aqueous dispersion of an optionally substituted poly-3,4 alkylene dioxythiophene cation and an associated polyanion; and

1% (w/v) to 100% (w/v) of one or more organic solvents, wherein the one or more organic solvents have a boiling point between from about 80°

C. to about 290°

C., wherein at least 30% (w/v)of the water from the aqueous dispersion is removed from said combination.

47. The coating of claim 46, wherein at least 90% of the water from the aqueous dispersion is removed.

48. The coating of claim 46, wherein the polyanion is polystyrene sulfonic acid (PSS).

49. The coating of claim 46, wherein the aqueous dispersion of said optionally substituted poly-3,4-alkylene dioxythiophene includes an aqueous dispersion of 0.5-5% by weight of poly-3,4-ethylene dioxythiophene and the anion is polystyrene sulfonic acid.

50. The coating of claim 46, further comprising at least one additive.

51. The coating of claim 50, wherein the additive is a binder.

52. The coating of claim 51, wherein the additive is ferric toluene sulfonic acid.

53. The coating of claim 52, wherein the ferric toluene sulfonic acid is present in trace amounts.

54. The coating of claim 46 wherein the aqueous dispersion of said optionally substituted poly-3,4-alkylene dioxythiophene includes an aqueous dispersion of 0.5-5% by weight of poly-3,4-ethylene dioxythiophene and the anion is polystyrene sulfonic acid.

55. The coating of claim 46, the aqueous dispersion of the optionally substituted poly-3,4-alkylene dioxythiophene cation and an associated polyanion is from about 0.38% to about 1.55% by weight of said composition.

56. The coating of claim 46, wherein the one or more organic solvents include lower alkyl acetamides, lower alcohols, including diol and triol alcohols, pyrrolidones, lower alkyl pyrrolidones, higher alkyl pyrrolidones, lower alkyl sulfoxides, or mixtures thereof.

57. The coating of claim 46, wherein the one or more organic solvent is glycol or glycerin.

58. The coating of claim 46, wherein the one or more organic solvents is dimethylsulfoxide.

59. The coating of claim 46, wherein the one or more organic solvents is a mixture of ethylene glycol and N-methylpyrrolidone.

60. The coating of claim 46, wherein the one or more organic solvents is a mixture of ethylene glycol, dimethylacetamide, and N-methylphyrrolidone.

61. The coating of claim 46, wherein the one or more organic solvents have a boiling point between from about 100°

C. to about 250°

C.

62. The coating of claim 46, wherein the polyanion is an anion of a polymeric carboxylic acid, a polymaleic acid, a polymeric sulphonic acid, or mixtures thereof.

63. The coating of claim 46, wherein the coating is configured as a layer.

64. The coating of claim 63, wherein the layer has a surface resistance of between from about 10 to about 10¹² Ω

/sq.

65. The coating of claim 63, having between from about 1 mg/m² to about 500 mg/m² of the composition in the layer.

66. The coating of claim 63, in which the layer has an optical density of between from about 0.0001 to about 0.05 at between from about 300 nm to about 700 nm.

67. The coating of claim 63, wherein the layer has a light transmission of between from about 10% to about 99% as measured by a BYK Gardner Hazegard plus machine.

68. The coating of claim 63, wherein the layer has a light transmission of between from about 80% to about 95% as measured by a BYK Gardner Hazegard plus machine.

69. A coating of claim 46 further comprising least one polymer, co-polymer, graft polymer, or blend thereof.

70. The coating of claim 69 further comprising a polymer, wherein the weight ratio of the composition to the polymer is about 10:

90 to about 0.1;

99.9.

71. The coating of claim 69, further comprising a polymer, wherein the weight ratio of the composition to the polymer is about 6:

94 to about 0.5;

99.5.

72. The coating of claim 69 further comprising a polymer wherein the polymer is a polyimide.

73. The coating of claim 46 wherein the aqueous dispersion is 0.5-5% by weight of poly-3,4-ethylene dioxythiophene.

74. The coating of claim 46,wherein the coating exhibits a charge carrier mobility of greater than 0.1 Cm²/V-S.

75. The coating of claim 46, wherein the coating is prepared by employing non-vacuum, coating processes, wherein the coating exhibits a charge carrier mobility of greater than 1 Cm²/V-S.

76. The coating of claim 46, wherein the coating exhibits a charger carrier mobility of greater than 10 Cm²/V-S, wherein the charge carrier mobility is measured by the combination of van der Pauw and Hall effect methods.