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EP-4735544-A1 - CURABLE INK COMPOSITIONS WITH WATER-SEQUESTRATION AGENTS

EP4735544A1EP 4735544 A1EP4735544 A1EP 4735544A1EP-4735544-A1

Abstract

Curable ink compositions include a (meth)acrylate-based component and a water sequestration component. The ink composition is inkjet printable. The (meth)acrylate- based component includes an aliphatic (meth)acrylate, aromatic (meth)acrylate, or a combination, a multifunctional (meth)acrylate, and a photoinitiator. The water sequestration component is a reactive pair, the reactive pair being a co-curable epoxy- functional part and a co-curable anhydride-functional part. Upon curing, the ink forms a matrix with epoxy-functional and anhydride-functional groups. The ink composition when disposed and cured is optically clear and has an irreversible water uptake of at least 2% by weight upon exposure to 85°C/85% Relative Humidity for 7 days.

Inventors

  • LEWANDOWSKI, KEVIN M.
  • SCHWARTZ, EVAN L.
  • HARTMANN-THOMPSON, CLAIRE
  • XIE, SIHAN
  • YOON, KYUNG HWAN
  • CHO, Yunjung

Assignees

  • 3M Innovative Properties Company

Dates

Publication Date
20260506
Application Date
20240619

Claims (20)

  1. 1. A curable ink composition comprising: a (meth)acrylate-based component capable of curing to form a (meth)acrylate- based matrix, comprising: at least one aliphatic (meth)acrylate, at least one aromatic (meth)acrylate, or a combination thereof; at least one multifunctional (meth)acrylate; and a photoinitiator; and a water sequestration component, the water sequestration component being a reactive pair, the reactive pair being a co-curable epoxy-functional part and a co-curable anhydride-functional part, wherein the co-curable anhydride -functional part comprises a co-curable aromatic anhydride, a co-curable aliphatic anhydride, or a combination thereof; such that upon curing, the ink composition forms a (meth)acrylate matrix wherein the (meth)acrylate matrix comprises epoxy-functional group and anhydride-functional groups, and wherein the (meth)acrylate matrix is capable of water sequestration whereby an anhydride-functional group, upon reacting with water forms acid-functional groups that react with epoxy-functional groups creating irreversible water uptake of the (meth)acrylate-based matrix, wherein the ink composition is inkjet printable, having a viscosity of 30 centipoise or less at a temperature of from room temperature to 35 °C, and is free from solvents, and wherein the ink composition when disposed and cured is optically clear, and has an irreversible water uptake of at least 2% by weight upon exposure to 85°C/85% Relative Humidity for 7 days.
  2. 2. The curable ink composition of claim 1, wherein the at least one aliphatic (meth)acrylate comprises a monofunctional (meth)acrylate compound of Formula I: H 2 C=CR2-(CO)-O-R3 Formula I wherein R3 is an alkyl group with 2-32 carbon atoms; and R2 is hydrogen or methyl.
  3. 3. The curable ink composition of claim 1, wherein the at least one aromatic (meth)acrylate comprises a monofunctional (meth)acrylate compound of Formula I: Formula II wherein at least one R1 comprises an aromatic substituent; t is an integer from 1 to 4; and R2 is hydrogen or methyl.
  4. 4. The curable ink composition of claim 1, wherein the at least one multifunctional (meth)acrylate comprises a compound of Formula II: (H 2 C=CR2-(CO)-O-) n A Formula III wherein R2 is hydrogen or methyl; (CO) is a carbonyl group C=O; and A is an n-valent group comprising an alkylene group, a heteroaromatic group, a fused aromatic group, a heteroalkylene group, or a group containing both heteroalkylene and aromatic groups; and n is an integer of 2 or greater.
  5. 5. The curable ink composition of claim 1, wherein at least a portion of the co-curable epoxy-functional part of the reactive pair of the water sequestration component comprises an epoxy-functional (meth)acrylate of Formula IV: H 2 C=CR2-(CO)-O-CH 2 -B Formula IV wherein R2 is hydrogen or methyl; (CO) is a carbonyl group C=O; and B is an epoxy-functional alkyl or heteroalkyl group.
  6. 6. The curable ink composition of claim 1, wherein at least a portion of the co-curable anhydride-functional part of the reactive pair of the water sequestration component comprises an aromatic anhydride (meth)acrylate of Formula V: H 2 C=CR2-(CO)-O-L 1 -O-(CO)-PA Formula V wherein R2 is hydrogen or methyl; (CO) is a carbonyl group C=O; L 1 is a divalent linking group comprising an alkylene group with at least 3 carbon atoms; and PA is a substituted or unsubstituted phthalic anhydride group.
  7. 7. The curable ink composition of claim 6, wherein the aromatic anhydride (meth)acrylate comprises an aromatic anhydride (meth)acrylate of Formula V: H 2 C=CR2-(CO)-O-L 1 -O-(CO)-PA Formula V wherein R2 is hydrogen; (CO) is a carbonyl group C=O; L 1 is a divalent linking group comprising a branched alkylene group with 3 carbon atoms, or a linear alkylene group with 4 carbon atoms; and PA is an unsubstituted phthalic anhydride group.
  8. 8. The curable ink composition of claim 1, wherein at least a portion of the co-curable anhydride-functional part of the reactive pair of the water sequestration component comprises an aliphatic anhydride (meth)acrylate of Formula VI: H 2 C=CR2-(CO)-O-L 2 -(CO)-O-(CO)-L 2 -O-(CO)-CR2=CH 2 Formula VI wherein R2 is hydrogen or methyl; (CO) is a carbonyl group C=O; each L 2 is a divalent linking group comprising alkylene groups or heteroalkylene groups linked by an ester group.
  9. 9. The curable ink composition of claim 8, wherein the aliphatic anhydride (meth)acrylate comprises an aliphatic anhydride (meth)acrylate of Formula VI: H 2 C=CR2-(CO)-O-L 2 -(CO)-O-(CO)-L 2 -O-(CO)-CR2=CH2 Formula VI wherein R2 is hydrogen; (CO) is a carbonyl group C=O; each L 2 is a divalent linking group comprising an alkylene group with at least 2 carbon atoms and an ester group.
  10. 10. The curable ink composition of claim 1, wherein the co-curable epoxy-functional part comprises 0.075 - 45% by weight of the total weight of the curable ink composition.
  11. 11. The curable ink composition of claim 1, wherein the co-curable anhydride -functional part comprises 0.075 - 45% by weight of the total weight of the curable ink composition.
  12. 12. An article comprising: a substrate with a first major surface and a second major surface; a cured organic layer adjacent to at least a portion of the second major surface of the substrate, wherein the cured organic layer comprises a crosslinked (meth)acrylate-based matrix containing epoxy-functional groups and anhydride-functional groups, and is optically clear; such that the cured organic layer has a water sequestration component, the water sequestration component being a reactive pair, the reactive pair being epoxyfunctional and anhydride-functional parts, wherein the (meth)acrylate matrix is capable of water sequestration whereby an anhydride-functional group, upon reacting with water forms acid-functional groups that react with epoxy-functional groups creating irreversible water uptake of the (meth)acrylate-based matrix,, wherein the irreversible water uptake is at least 2% by weight upon exposure to 85°C/85% Relative Humidity for 7 days.
  13. 13. The article of claim 12, wherein the cured organic layer comprises a curable ink composition that has been disposed and cured on at least a portion of the second major surface of the substrate, wherein the curable ink composition comprises: a (meth)acrylate-based component capable of curing to form a (meth)acrylate- based matrix, comprising: at least one aliphatic (meth)acrylate, at least one aromatic (meth)acrylate, or a combination thereof; at least one multifunctional (meth)acrylate; and a photoinitiator; and a water sequestration component, the water sequestration component being a reactive pair, the reactive pair being a co-curable epoxy-functional part and a co-curable anhydride-functional part, wherein the co-curable anhydride- functional part comprises a co-curable aromatic anhydride, a co-curable aliphatic anhydride, or a combination thereof; wherein the curable ink composition is inkjet printable having a viscosity of 30 centipoise or less at a temperature of from room temperature to 35 °C and is free from solvents.
  14. 14. The article of claim 12, wherein the cured organic layer has a thickness of from 1-16 micrometers.
  15. 15. The article of claim 12, wherein the article comprises an electronic device and the substrate comprises an optical electronic component.
  16. 16. The article of claim 15, wherein the optical electronic component comprises an organic light emitting diode (OLED), a quantum dot light emitting diode, a micro light emitting diode, or a quantum nanorod electronic device.
  17. 17. The article of claim 13, wherein at least a portion of the co-curable epoxy-functional part of the reactive pair of the water sequestration component comprises an epoxy- fimctional (meth)acrylate of Formula IV : H 2 C=CR2-(CO)-O-CH 2 -B Formula IV wherein R2 is hydrogen or methyl; (CO) is a carbonyl group C=O; and B is an epoxy-functional alkyl or heteroalkyl group.
  18. 18. The article of claim 13, wherein at least a portion of the co-curable anhydride- functional part of the reactive pair of the water sequestration component comprises an aromatic anhydride (meth)acrylate of Formula V : H 2 C=CR2-(CO)-O-L 1 -O-(CO)-PA Formula V wherein R2 is hydrogen or methyl; (CO) is a carbonyl group C=O; L 1 is a divalent linking group comprising a branched alkylene group with 3 carbon atoms, or a linear alkylene group with 4 carbon atoms; and PA is an unsubstituted phthalic anhydride group.
  19. 19. The article of claim 13, wherein at least a portion of the co-curable anhydride- functional part of the reactive pair of the water sequestration component comprises an aliphatic anhydride (meth)acrylate of Formula VI: H 2 C=CR2-(CO)-O-L 2 -(CO)-O-(CO)-L 2 -O-(CO)-CR2=CH 2 Formula VI wherein R2 is hydrogen or methyl; (CO) is a carbonyl group C=O; L 2 is a divalent linking group comprising a 2 alkylene groups with at least 2 carbon atoms, linked with an ester linkage.
  20. 20. The article of claim 13, wherein the co-curable epoxy-functional part comprises 0.075 - 45% by weight of the total weight of the curable ink composition.

Description

CURABLE INK COMPOSITIONS WITH WATER-SEQUESTRATION AGENTS Summary Disclosed herein are curable ink compositions with water sequestration agents. When cured to form an organic layer, and the water sequestration agents are polymerized into the matrix of the organic layer. Also disclosed are articles formed by disposing the curable ink compositions on a substrate and curing the ink to form an organic layer. In some embodiments, the curable ink composition comprises a (meth)acrylate- based component capable of curing to form a (meth)acrylate-based matrix, and a water sequestration component. The ink composition is inkjet printable, having a viscosity of 30 centipoise or less at a temperature of from room temperature to 35°C, and is free from solvents. The (meth)acrylate -based component comprises at least one aliphatic (meth)acrylate, at least one aromatic (meth)acrylate, or a combination thereof, at least one multifunctional (meth)acrylate, and a photoinitiator. The water sequestration component being a reactive pair, the reactive pair being a co-curable epoxy-functional part and a co- curable anhydride-functional part, wherein the co-curable anhydride-functional part comprises a co-curable aromatic anhydride, a co-curable aliphatic anhydride, or a combination thereof. Upon curing, the ink composition forms a (meth)acrylate matrix where the (meth)acrylate matrix comprises epoxy-functional group and anhydride-functional groups, such that the (meth)acrylate matrix is capable of water sequestration whereby an anhydride-functional group, upon reacting with water forms acid-functional groups that react with epoxy-functional groups creating irreversible water uptake of the (meth)acrylate-based matrix. The ink composition when disposed and cured is optically clear and has an irreversible water uptake of at least 2% by weight upon exposure to 85°C/85% Relative Humidity for 7 days. Also disclosed are articles formed with the curable ink compositions described above. In some embodiments, the articles comprise a substrate with a first major surface and a second major surface, and a cured organic layer adjacent to at least a portion of the second major surface of the substrate, where the cured organic layer comprises a crosslinked (meth)acrylate-based matrix containing epoxy-functional groups and anhydride-functional groups, and is optically clear, and is formed by curing the curable ink compositions described above. Brief Description of the Drawings The present application may be more completely understood in consideration of the following detailed description of various embodiments of the disclosure in connection with the accompanying drawings. Figure 1 is a cross-sectional view of an article of this disclosure. Detailed Description Optical devices are becoming more and more complex, which impacts what materials can be used in them. In particular, organic polymeric materials have found widespread use in optical devices, however, they still must meet the stringent requirements and demands needed for performance. For example, thin organic polymeric fdms are desirable for a wide range of uses in optical devices, as adhesives, protective layers, spacer layers, and the like. As articles have become more complex, the physical demands upon these layers have increased. For example, as optical devices have become more compact, they often include additional layers, resulting in a growing need for thinner layers. At the same time, since the layers are thinner, the layers also need to be more precise. For example, a thin spacer layer (of 1 micrometer thickness) needs to be level and free of gaps and holes in order to provide the proper spacing function. This requires deposition of the organic layer in a precise and consistent manner. Additionally, not only do these layers have to fulfill their physical role (adhesion, protection, spacing, and the like) they must also provide the requisite optical properties. Among the properties that are becoming increasingly important is refractive index. As light travels through the layers of a multilayer article, it encounters the interface between layers. If the refractive indices of the layers are different, light can be refracted. Therefore, to minimize this refraction, matching of the refractive indices of layers within a multilayer article is desirable. An example of an optical device that utilizes thin film layers are OLED (organic light-emitting diode) devices. In particular, the organic light-emitting devices are susceptible to degradation from the permeation of certain liquids and gases, such as water vapor and oxygen. To reduce permeability to these liquids and gases, barrier coatings are applied to the OLED device, which is known in the art as thin fdm encapsulation. Typically, these barrier coatings require a high refractive index to match with other layers in the devices. Typically, the organic thin fdm layers are a cured organic matrix. Because the layers are very thin the barri