Electro-optic displays, and materials for use therein

• US 7,551,346 B2
• Filed: 06/26/2007
• Issued: 06/23/2009
• Est. Priority Date: 11/05/2003
• Status: Active Grant

• Current Assignee: E Ink Corporation (E Ink Holdings Incorporated), Versum Materials US, LLC (Merck & Co., Inc.)
• Original Assignee: E Ink Corporation (E Ink Holdings Incorporated), Air Products and Chemicals Incorporated (Linde Plc)
• Inventors: Danner, Guy M., Miller, David D., Fazel, Shafiq N., Cao, Lan, Klingenberg, Eric H.
• Primary Examiner(s): Spector; David N
• Application Number:
  US11/768,395
• Publication Number:
  US 20070286975A1
• Time in Patent Office: 728 Days
• Field of Search: 359/245, 359/254, 359/265, 359/296, 359/321, 428/343, 428/355.AC, 428/355.EP
• US Class Current: 359/321
• CPC Class Codes: C08G 18/0804 Manufacture of polymers containing ionic or ionogenic groups
• CPC Class Codes: C08G 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/765 alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C09J 175/08 from polyethers
• CPC Class Codes: G02F 1/167 by electrophoresis
• CPC Class Codes: G02F 1/1675 Constructional details
• CPC Class Codes: G02F 2202/28 Adhesive materials or arrangements
• CPC Class Codes: Y10T 428/14 Layer or component removable to expose adhesive
• CPC Class Codes: Y10T 428/1476 Release layer
• CPC Class Codes: Y10T 428/24 Structurally defined web or sheet [e.g., overall dimension, etc.]
• CPC Class Codes: Y10T 428/28 Web or sheet containing structurally defined element or component and having an adhesive outermost layer
• CPC Class Codes: Y10T 428/2891 including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof

Abstract

An electro-optic display comprises a layer of solid electro-optic material; a backplane comprising at least one electrode; and an adhesive layer disposed between the layer of electro-optic material and the backplane and adhesively securing the layer of electro-optic material to the backplane, the adhesive layer comprising a thermally-activated cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid. The cross-linking agent reduces void growth when the display is subjected to temperature changes.

Claims

1. An electro-optic display comprising:

a layer of solid electro-optic material capable of changing at least one optical characteristic upon application of an electric field thereto;

a backplane comprising at least one electrode arranged to apply an electric field to the layer of electro-optic material; and

an adhesive layer disposed between the layer of electro-optic material and the backplane and adhesively securing the layer of electro-optic material to the backplane,

the adhesive layer comprising a thermally-activated cross-linking agent capable, upon exposure to an activation temperature, of cross-linking the adhesive layer, the cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid.

2. An electro-optic display according to claim 1 wherein the cross-linking agent is derived from a soybean or linseed oil.

3. An electro-optic display according to claim 1 wherein the cross-linking agent is a C_1-6 alkyl, C_2-6 alkenyl, epoxidized C_2-6 alkenyl, monoglycerol, diglycerol, C_4-6 polyol or glycol ester of a vegetable oil fatty acid, wherein the ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of the fatty acid.

4. An electro-optic display according to claim 1 wherein the cross-linking agent has an average of at least about three oxirane groups per molecule.

5. An electro-optic display according to claim 1 wherein the cross-linking agent is present in the adhesive layer in a concentration of at least about 5,000 parts per million by weight.

6. An electro-optic display according to claim 5 wherein the cross-linking agent is present in the adhesive layer in a concentration of at least about 10,000 parts per million by weight.

7. An electro-optic display according to claim 6 wherein the cross-linking agent is present in the adhesive layer in a concentration of from about 20,000 to about 40,000 parts per million by weight.

8. An electro-optic display according to claim 1 wherein the adhesive layer comprises a polyurethane.

9. An electro-optic display according to claim 8 wherein the adhesive layer comprises a polyurethane-polyurea polymer that is formed by reaction of at least one isocyanate with a polyol and a polyamine.

10. An electro-optic display according to claim 1 wherein the adhesive layer further comprises an agent effective to reduce the volume resistivity of the adhesive layer after cross-linking.

11. An electro-optic display according to claim 10 wherein the volume resistivity reducing agent comprises at least one of a salt, a polyelectrolyte or a hydroxyl containing polymer having a number average molecular weight not greater than about 5000.

12. An electro-optic display according to claim 11 wherein the volume resistivity reducing agent comprises a quaternary ammonium salt or a polyethylene glycol.

13. An electro-optic display according to claim 12 wherein the volume resistivity reducing agent comprises tetrabutylammonium chloride, tetrabutylammonium hexafluorophosphate or a polyethylene glycol having a number average molecular weight not greater than about 2000.

14. A process for producing an electro-optic display, the process comprising:

providing an assembly comprising a layer of solid electro-optic material capable of changing at least one optical characteristic upon application of an electric field thereto;

a backplane comprising at least one electrode arranged to apply an electric field to the layer of electro-optic material; and

an adhesive layer disposed between the layer of electro-optic material and the backplane and adhesively securing the layer of electro-optic material to the backplane, the adhesive layer comprising a thermally-activated cross-linking agent capable of cross-linking the adhesive layer, the cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid; and

exposing the adhesive layer to a temperature sufficient to activate the cross-linking agent, thereby cross-linking the adhesive layer.

15. An electro-optic display comprising:

a layer of solid electro-optic material capable of changing at least one optical characteristic upon application of an electric field thereto;

a backplane comprising at least one electrode arranged to apply an electric field to the layer of electro-optic material; and

an adhesive layer disposed between the layer of electro-optic material and the backplane and adhesively securing the layer of electro-optic material to the backplane,

the adhesive layer having been cross-linked by a thermally-activated cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid.

16. An article of manufacture comprising in order:

a light-transmissive electrically-conductive layer;

a layer of a solid electro-optic medium in electrical contact with the electrically-conductive layer;

an adhesive layer; and

a release sheet,

the adhesive layer comprising a thermally-activated cross-linking agent capable, upon exposure to an activation temperature, of cross-linking the adhesive layer, the cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid.

17. An article of manufacture comprising:

a layer of a solid electro-optic medium having first and second surfaces on opposed sides thereof,

a first adhesive layer on the first surface of the layer of solid electro-optic medium;

a release sheet disposed on the opposed side of the first adhesive layer from the layer of solid electro-optic medium; and

a second adhesive layer on the second surface of the layer of solid electro-optic medium,

wherein at least one of the first and second adhesive layers comprises a thermally-activated cross-linking agent capable, upon exposure to an activation temperature, of cross-linking the adhesive layer in which it is present, the cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid.

18. An article of manufacture comprising, in order:

a release sheet;

a layer of a solid electro-optic medium;

an adhesive layer; and

at least one of a light-transmissive protective layer and a light-transmissive electrically-conductive layer,

the adhesive layer comprising a thermally-activated cross-linking agent capable, upon exposure to an activation temperature, of cross-linking the adhesive layer, the cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid.

19. An adhesive composition comprising a polyurethane and a thermal cross-linking agent capable, upon exposure to an activation temperature, of cross-linking the polyurethane, the cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid.

20. An adhesive composition according to claim 19 wherein the cross-linking agent is derived from a soybean or linseed oil.

21. An adhesive composition according to claim 19 wherein the cross-linking agent is a C_1-6 alkyl, C_2-6 alkenyl, epoxidized C_2-6 alkenyl, monoglycerol, diglycerol, C_4-6 polyol or glycol ester of a vegetable oil fatty acid, wherein the ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of the fatty acid.

22. An adhesive composition according to claim 19 wherein the cross-linking agent has an average of at least about three oxirane groups per molecule.

23. An adhesive composition according to claim 19 wherein the cross-linking agent is present in a concentration of at least about 5,000 parts per million by weight.

24. An adhesive composition according to claim 23 wherein the cross-linking agent is present in a concentration of at least about 10,000 parts per million by weight.

25. An adhesive composition according to claim 24 wherein the cross-linking agent is present in a concentration of from about 20,000 to about 40,000 parts per million by weight.

26. A laminate structure comprising first and second layers of solid glass, metal or plastic, and an adhesive layer disposed between the first and second layers and securing the first and second layers to each other, wherein the adhesive layer comprises the adhesive layer comprising a thermally-activated cross-linking agent capable, upon exposure to an activation temperature, of cross-linking the adhesive layer, the cross-linking agent comprising an epoxidized vegetable oil fatty acid or an epoxidized ester of such a fatty acid.

27. A laminate structure according to claim 26 wherein at least one of the first and second layers has at least one layer of an inorganic, organic or metallized components within or on its surface.

28. A laminate structure according to claim 26 in the form of a printed circuit board.

29. A laminate structure according to claim 26 wherein the cross-linking agent has an average of at least about three oxirane groups per molecule.

30. A laminate structure according to claim 26 wherein the adhesive layer comprises a polyurethane.

31. A laminate structure according to claim 26 wherein the adhesive layer further comprises an agent effective to reduce the volume resistivity of the adhesive layer after cross-linking.