Curable composition, method for preparing curable composition

Abstract

A curable composition for an electronic device includes: a curable material; and an oxide-containing complex; wherein the oxide-containing complex includes: i) an oxide core; and ii) an organic group chemically bonded to an atom on the surface of the oxide core, the organic group including: a) a curable group capable of reacting with the curable material; and b) a linking group connecting the atom on the surface of the oxide core to the curable group, and the oxide core includes alumina, silica, or a combination thereof.

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10-2019-0179804, filed on Dec. 31, 2019, which is incorporated herein by reference in its entirety for all purposes as if fully set forth herein. Technical Field

[0003] Exemplary embodiments of the present invention generally relate to curable compositions, and more particularly, to methods for preparing the curable compositions, cured materials of the curable compositions, methods for preparing the cured materials, and electronic devices including the cured materials. Background Art

[0004] Adhesive members that can be used for various purposes in various electronic devices need to exhibit satisfactory performance in terms of optical properties, adhesive properties, durability, and the like.

[0005] In recent years, flexible, foldable, and / or rollable articles and / or electronic devices have been actively developed.

[0006] The above information disclosed in this background art section is only for understanding the background of the inventive concept, and thus, it may include information that does not constitute the prior art. Summary of the Invention

[0007] During the development of flexible, foldable, and / or rollable electronic devices (e.g., display devices), the applicant has recognized the need to develop an adhesive member for flexible electronic devices that is easily deformable (e.g., bent and / or twisted) when an external force is applied and also has excellent resilience when the external force is removed.

[0008] Electronic devices and articles manufactured according to the principles and exemplary embodiments of the present invention include cured materials made from curable compositions having excellent optical properties, elasticity, flexibility, and resilience.

[0009] Advantageous methods for preparing the curable compositions and methods for preparing the cured materials according to the principles and exemplary embodiments of the present invention are particularly advantageous for use in electronic devices and articles.

[0010] Additional features of the inventive concept will be set forth in the following description, and will be, in part, apparent from the description, or may be learned by practice of the inventive concept.

[0011] According to one aspect of the present invention, a curable composition comprises: a curable material; and an oxide-containing complex; wherein the oxide-containing complex comprises: i) an oxide core; and ii) an organic group chemically bonded to an atom on the surface of the oxide core, the organic group comprising: a) a curable group capable of reacting with the curable material; and b) a linking group that links the atom on the surface of the oxide core to the curable group, and the oxide core comprises alumina, silica, or a combination thereof. The oxide core may have a diameter D15 of from about 1 nm to about 50 nm.

[0012] The oxide core may have a refractive index of from about 1.2 to about 2.5.

[0013] The organic group may have Formula 1:

[0014]

[0015] wherein, in Formula 1,

[0016] L 1 may be:

[0017] *-N(R 11 )-*', *-O-*', *-S-*', or *-C(=O)-*'; or

[0018] C 1 -C 60 alkylene, C 1 -C 60 alkyleneoxy, C 6 -C 60 arylene, or C 6 -C 60 aryloxy, all unsubstituted or substituted with deuterium, hydroxyl, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, or any combination thereof;

[0019] Both * and *' may indicate a binding site to an adjacent atom;

[0020] R 11 may be hydrogen, deuterium, hydroxyl, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl, or biphenyl;

[0021] a1 may be an integer from 1 to 10,000, and when a1 is 2 or greater, at least two L 1may be the same as or different from each other;

[0022] T 20 may be a curable group;

[0023] a2 may be an integer from 1 to 10, and when a2 is 2 or greater, at least two Ts 20 may be the same as or different from each other; and

[0024] T 1 and T 2 may each independently be hydrogen, deuterium, a hydroxyl group, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, an oxygen atom bonding to a silicon atom in an adjacent linking group, or a bonding site of oxygen between the linking group and an adjacent linking group;

[0025] wherein, in Formula 1, * may indicate a bonding site to the atom on the surface of the oxide core.

[0026] As the curable group of the T 20 may be a group of Formula 1-2(1) to Formula 1-2(8) as defined herein.

[0027] The oxide core and the organic group in the oxide-containing complex may have a weight ratio between about 10:1 and about 1:10.

[0028] The curable material may have a refractive index of about 1.2 to about 2.0.

[0029] The difference between the refractive index of the curable material and the refractive index of the oxide core may be about 0.01 to about 0.5.

[0030] According to another aspect of the present invention, a method for preparing a curable composition includes the following steps: providing an oxide-containing complex, the oxide-containing complex including: i) an oxide core; and ii) an organic group, the organic group being chemically bonded to an atom on the surface of the oxide core; and mixing the oxide-containing complex with a curable material to provide a curable composition including the oxide-containing complex and the curable material; wherein the organic group includes: a) a curable group capable of reacting with the curable material; and b) a linking group connecting the atom on the surface of the oxide core to the curable group; and the oxide core includes alumina, silica, or a combination thereof.

[0031] The step of providing the complex containing the oxide includes reacting an oxide precursor with a compound represented by Formula 2:

[0032]

[0033] wherein, in Formula 2, the variables are defined herein.

[0034] The cured material may include the curable composition described above.

[0035] The cured material may include a matrix material derived from the curable material, and the atoms on the surface of the oxide core in the complex containing the oxide may be chemically bonded to the matrix material via i) a residual group resulting from the reaction between the curable group in the complex containing the oxide and the curable material and ii) the linking group in the complex containing the oxide.

[0036] The matrix material may include a binder material.

[0037] The cured material may include a film.

[0038] The film may have a thickness of about 0.1 μm to about 700 μm.

[0039] The light transmittance with respect to light having a maximum emission wavelength of 600 nm may be about 96% or higher.

[0040] A method for preparing a cured material includes the following steps: providing the curable composition described above on a substrate; and curing the curable composition.

[0041] The step of curing the curable composition may include exposing the curable composition to ultraviolet light.

[0042] An electronic device may include the cured material described above.

[0043] The electronic device may include a flexible, foldable or rollable electronic device.

[0044] It should be understood that the foregoing general description and the following detailed description are both exemplary and explanatory and are intended to provide further explanation of the claimed invention. Brief Description of the Drawings

[0045] Drawings are included to provide a further understanding of the present invention, which are incorporated into this specification and form a part of this specification. The drawings illustrate exemplary embodiments of the present invention and, together with the description, are used to explain the inventive concept.

[0046] Figure 1Schematic diagram of an exemplary embodiment of a curable composition prepared according to the principles of the present invention.

[0047] Figure 2 is Figure 1 Schematic diagram of an exemplary embodiment of an oxide-containing complex of

[0048] Figure 3 Schematic diagram of an exemplary embodiment of a method for preparing an oxide-containing complex according to the principles of the present invention.

[0049] Figure 4 Schematic diagram of another exemplary embodiment of an oxide-containing complex constructed according to the principles of the present invention.

[0050] Figure 5 Schematic diagram of an exemplary embodiment of a cured material prepared according to the principles of the present invention. Detailed Description

[0051] In the following description, for purposes of explanation, numerous specific details are set forth in order to provide a thorough understanding of various exemplary embodiments or implementations. As used herein, "embodiment" and "implementation" are interchangeable terms that are non-limiting examples of a device or method that employs one or more inventive concepts disclosed herein. However, it will be apparent that the various exemplary embodiments may be practiced without these specific details or with one or more equivalent arrangements. In other instances, well-known structures and devices are shown in block diagram form to avoid unnecessarily obscuring the various exemplary embodiments. Additionally, the various exemplary embodiments may be different, but not necessarily exclusive. For example, without departing from the inventive concept of the present invention, the specific shapes, configurations, and characteristics of an exemplary embodiment may be used or implemented in another exemplary embodiment.

[0052] Unless otherwise stated, the exemplary embodiments shown should be understood to provide exemplary features of different details of some ways in which the inventive concepts of the present invention may be implemented in practice. Thus, unless otherwise stated, without departing from the inventive concept of the present invention, the features, components, modules, layers, films, panels, regions, and / or aspects, etc. (hereinafter individually or collectively referred to as "elements") of the various embodiments may be combined, separated, interchanged, and / or rearranged otherwise.

[0053] Cross-hatching and / or shading are commonly provided in the drawings to clarify the boundaries between adjacent elements. Thus, unless otherwise specified, the presence or absence of cross-hatching or shading does not convey or imply any preference or requirement regarding a particular material, material property, dimension, scale, commonality between the elements shown, and / or any other characteristic, attribute, property, etc. of the elements. Additionally, in the drawings, element sizes and relative sizes may be exaggerated for clarity and / or descriptive purposes. When exemplary embodiments can be implemented differently, a particular process order may be performed differently than the order described. For example, two consecutively described processes may be performed substantially simultaneously or in an order opposite to the described order. Additionally, like reference numerals denote like elements.

[0054] When an element or layer is referred to as being "on", "connected to", or "coupled to" another element or layer, the element or layer can be directly on, directly connected to, or directly coupled to the other element or layer, or intervening elements or layers may be present. However, when an element or layer is referred to as being "directly on", "directly connected to", or "directly coupled to" another element or layer, no intervening elements or layers are present. For this reason, the term "connected" can refer to physical, electrical, and / or fluid connection, whether or not intervening elements are present. Additionally, the D1 axis, D2 axis, and D3 axis are not limited to the three axes of a rectangular coordinate system, such as the x-axis, y-axis, and z-axis, and can be interpreted in a broader sense. For example, the D1 axis, D2 axis, and D3 axis can be perpendicular to each other, or can represent different directions that are not perpendicular to each other. For the purposes of this disclosure, "at least one of X, Y, and Z" and "at least one selected from the group consisting of X, Y, and Z" can be interpreted as only X, only Y, only Z, or any combination of two or more of X, Y, and Z, such as by way of example XYZ, XYY, YZ, and ZZ. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.

[0055] Although the terms "first", "second", etc. are used herein to describe different types of elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, a first element discussed below could be termed a second element without departing from the teachings of this disclosure.

[0056] For purposes of description, this document may use spatial relative terms, such as "below", "beneath", "under", "lower", "above", "upper", "on top", "higher", and "side" (e.g., in "sidewall"), etc., and thereby describe the relationship of one element to other elements as shown in the figures. In addition to the orientation depicted in the drawings, spatial relative terms are also intended to encompass different orientations of the device during use, operation, and / or manufacture. For example, if the device is flipped in the drawing, an element described as "below" or "beneath" other elements or features will subsequently be positioned "above" the other elements or features. Thus, the exemplary term "below" can encompass both the orientation of "above" and "below". In addition, the device can be otherwise positioned (rotated 90 degrees or in other orientations), and thus the spatial relative terms used herein can be interpreted accordingly.

[0057] The terms used herein are for the purpose of describing particular embodiments and are not intended to be limiting. As used herein, unless the context clearly indicates otherwise, the singular forms "a", "an", and "the" are also intended to include the plural forms. In addition, when used in this specification, the terms "comprises", "comprising", "includes", and "including" specify the presence of stated features, integers, steps, operations, elements, components, and / or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof. It is also noted that, as used herein, the terms "substantially", "about", and other similar terms are used as approximate terms and not as terms of degree, and thus are used to account for the inherent deviations of measured, calculated, and / or set values that would be recognized by one of ordinary skill in the art.

[0058] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. Unless specifically defined herein, terms (e.g., terms defined in a general dictionary) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and should not be interpreted as ideal or overly formal.

[0059] As used herein, the term "nano" may be abbreviated as "nm".

[0060] As used herein, the term "micro" may be abbreviated as "μm".

[0061] As used herein, the term "percent" may be abbreviated as "%".

[0062] The terms "hydrogen" and "deuterium" refer to their respective atoms and corresponding free radicals, and the terms "-F, -Cl, -Br and -I" are free radicals of fluorine, chlorine, bromine and iodine, respectively.

[0063] As used herein, the term "atom" can represent an element or its corresponding free radical bonded to one or more other atoms.

[0064] As used herein, a substituent for a monovalent group such as an alkyl group can also independently be a substituent for a corresponding divalent group such as an alkylene group.

[0065] Figure 1 is a schematic diagram of an exemplary embodiment of a curable composition prepared according to the principles of the present invention. Figure 2 is Figure 1 a schematic diagram of an exemplary embodiment of an oxide-containing complex of Figure 3 is a schematic diagram of an exemplary embodiment of a method for preparing an oxide-containing complex according to the principles of the present invention. Figure 4 is a schematic diagram of another exemplary embodiment of an oxide-containing complex constructed according to the principles of the present invention. Figure 5 is a schematic diagram of an exemplary embodiment of a cured material prepared according to the principles of the present invention.

[0066] Figure 1 The curable composition 100 shown in Figures 2 to 4 The oxide-containing complex 110 shown in Figures 2 to 4 can include: i) an oxide core 111; and ii) an organic group 113 chemically bonded to atoms 111A on the surface of the oxide core 111. The oxide-containing complex 110 can include at least one organic group 113.

[0067] By curing Figure 1 the curable composition 100 shown in Figure 5 the cured material 200 shown in Figure 5The cured material 200 may include a matrix material 220 derived from a curable material 120 included in the curable composition 100. Atoms 111A on the surface of the oxide-containing complex 110 included in the curable composition 100 may be "chemically bonded" to the matrix material 220 via i) a residual group 118 resulting from the reaction between the curable group 117 in the oxide-containing complex 110 and the curable material 120 and ii) a linking group 115 in the oxide-containing complex 110. Thus, Figure 5 the cured material 200 is different from a cured material (e.g., film B) in which the above-described matrix material and the oxide core (e.g., spherical oxide particles) are not "chemically bonded to each other" and are "physically mixed" with each other.

[0068] As described above, atoms 111A on the surface of the oxide core 111 in the cured material 200 may be "firmly and chemically bonded to" the matrix material 220. Thus, even when an external force such as bending and / or twisting is applied to the cured material 200 and then the external force is removed, the oxide core 111 can still effectively act as a structural support for restoring the original shape of the cured material 200. Therefore, the cured material 200 may have excellent resilience.

[0069] Oxide - containing complex 110 in curable composition 100

[0070] Figure 1 The curable composition 100 may include an oxide-containing complex 110. The oxide core 111 in the oxide-containing complex 110 may include aluminum oxide (e.g., Al 2 O 3 ), silicon oxide (e.g., SiO 2 ), or a combination thereof. Since the oxide core 111 includes aluminum oxide, silicon oxide, or a combination thereof, Figure 5 the cured material 200 may have excellent optical properties (e.g., light transmittance or refractive index, etc.).

[0071] For example, the oxide core 111 may be aluminum oxide or silicon oxide. In some exemplary embodiments, the oxide core 111 may be silicon oxide. In one or more exemplary embodiments, the atoms 111A on the surface of the oxide core 111 may be oxygen. The oxide core 111 may be spherical particles.

[0072] For example, the diameter D15 of the oxide core 111 may be in the range of about 1 nm to about 50 nm, about 1 nm to about 30 nm, or about 15 nm to about 25 nm. The refractive index of the oxide core 111 may be in the range of about 1.2 to about 2.5, about 1.2 to about 2.0, about 1.2 to about 1.8, or about 1.3 to about 1.8.

[0073] Since the diameter D15 and / or refractive index of the oxide core 111 are within any of the ranges described above, Figure 5 the cured material 200 can have excellent optical properties (e.g., light transmittance or refractive index, etc.). The diameter D15 can be measured by evaluating the particle size distribution curve using a particle size analyzer and evaluating the diameter corresponding to 15% by passing mass percentage.

[0074] Figures 2 to 4 The oxide-containing complex 110 in can include at least one organic group 113.

[0075] In an exemplary embodiment, the organic group 113 can be represented by Formula 1:

[0076]

[0077] Wherein, in Formula 1,

[0078] L 1 can be:

[0079] *-N(R 11 )-*', *-O-*', *-S-*', or *-C(=O)-*'; or

[0080] C 1 -C 60 alkylene, C 1 -C 60 alkoxyalkylene, C 6 -C 60 arylene or C 6 -C 60 aryloxy, all of which are unsubstituted or substituted with deuterium, hydroxyl, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl or any combination thereof,

[0081] * and *' can both indicate the binding positions to adjacent atoms,

[0082] R 11 can be hydrogen, deuterium, hydroxyl, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl or biphenyl,

[0083] a1 can be an integer from 1 to 10,000 (e.g., an integer from 1 to 5,000 or an integer from 1 to 1,000), and when a1 is 2 or greater, at least two L 1may be the same as or different from each other, T 20 may be a curable group 117,

[0084] a2 may be an integer from 1 to 10, and when a2 is 2 or greater, at least two Ts 20 may be the same as or different from each other,

[0085] T 1 and T 2 may each independently be hydrogen, deuterium, a hydroxyl group, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, an oxygen atom bonding to a silicon atom in an adjacent linking group, or a bonding site to an oxygen atom disposed between a linking group and an adjacent linking group,

[0086] wherein, in Formula 1, * indicates a bonding site to an atom 111A on the surface of the oxide core 111.

[0087] The curable group 117 in the oxide-containing complex 110 and the T in Formula 1 20 may be any suitable group that can react with the curable material 120 in the curable composition 100 during curing.

[0088] For example, the curable group 117 in the oxide-containing complex 110 and the T in Formula 1 20 may include vinyl groups, acrylate groups, acrylamide groups, epoxy groups, or any combination thereof.

[0089] In an exemplary embodiment, the curable group 117 in the oxide-containing complex 110 and the T in Formula 1 20 may be a group represented by one of Formula 1-2(1) to Formula 1-2(8):

[0090]

[0091] wherein, in Formula 1-2(1) to Formula 1-2(8),

[0092] R 1 to R 5 may each independently be hydrogen, deuterium, a hydroxyl group, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl or biphenyl, and

[0093] * may indicate a bonding site to the linking group 115.

[0094] The organic group 113 in the oxide-containing complex 110 may include a linking group 115. Thus, Figure 5 the curable material 200 in

[0095] may have improved elasticity, flexibility, and / or resilience.

[0096] For example, referring to Formula 1, the linking group 115 may be a group represented by Formula 1-1:

[0097]

[0098] wherein, in Formula 1-1, L 1 , a1, T 1 , T 2 and * may be understood by referring to the descriptions of L 1 , a1, T 1 , T 2 and * provided herein, respectively, and *' may indicate the binding site to the curable group 117 in the oxide-containing complex 110 or T 20 in Formula 1.

[0099] For example, in the oxide-containing complex 110 shown in Figure 4 , the atom 111A on the surface of the oxide core 111 is oxygen. Additionally, Figure 4 the linking group 115 in the oxide-containing complex 110 shown in 1 may be a group represented by Formula 1-1, wherein T 2 may be the binding site to the oxygen disposed between the linking group 115 and an adjacent linking group, T 1 may be the oxygen bonded to silicon in an adjacent linking group, L 20 may be propylene, and a1 may be 1, and the curable group 117 (or T 1 in Formula 1) may be a group represented by Formula 1-2(2), wherein R 2 may be methyl, and R 3 and R

[0100] In some exemplary embodiments, although not seen in Figure 4 , the linking group 115 in the oxide-containing complex 110 shown in Figure 4 may be a group represented by Formula 1-1, wherein T 1 may be the binding site to the oxygen disposed between the linking group 115 and an adjacent linking group, T 2 may be the oxygen bonded to silicon in an adjacent linking group, L1 may be propyleneoxy, and a1 may be 1, and the curable group 117 (or T in Formula 1) 20 ) may be a group represented by Formula 1-2(5), wherein, R 1 may be methyl, and R 2 and R 3 may both be hydrogen.

[0101] The weight ratio between the oxide core 111 and the organic group 113 in the oxide-containing complex 110 may be in the range of about 10:1 to about 1:10 (e.g., about 7:1 to about 1:7). In some exemplary embodiments, the weight ratio between the oxide core 111 and the organic group 113 in the oxide-containing complex 110 may be in the range of about 1:1 to about 1:5 (e.g., about 1:1 to about 1:3). When the weight ratio between the oxide core 111 and the organic group 113 in the oxide-containing complex 110 is within any of the ranges described above, Figure 5 the cured material 200 may have excellent elasticity, flexibility, and / or resilience and excellent optical properties.

[0102] Curable material 120 in curable composition 100

[0103] Figure 1 The curable material 120 in the curable composition 100 shown in Figure 5 may be any suitable material that can be changed into the matrix material 220 in the cured material 200 shown in Figure 5 through a curing process. The curable material 120 may be composed of one type of compound or may be a mixture of at least two different types of compounds. The refractive index of the curable material 120 may be in the range of about 1.2 to about 2.0, about 1.2 to about 1.7, about 1.2 to about 1.5, or about 1.3 to about 1.5. Since the refractive index of the curable material 120 is within any of the ranges described above, Figure 5

[0104] Figure 5 the cured material 200 may have excellent optical properties (e.g., light transmittance or refractive index, etc.). For example, the curable material 120 may be a photopolymerizable monomer.

[0105] Examples of acrylic monomers include: monofunctional (meth)acrylate monomers such as 2-ethylphenoxy (meth)acrylate, 2-ethylphenylthio (meth)acrylate, phenyl (meth)acrylate, biphenylmethyl (meth)acrylate, benzyl (meth)acrylate, 2-phenylethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 2-(2-methylphenyl)ethyl (meth)acrylate, 2-(3-methylphenyl)ethyl (meth)acrylate, 2-(4-methylphenyl)ethyl (meth)acrylate, 2-(4-propylphenyl)ethyl (meth)acrylate, 2-(4-(1-methylethyl)phenyl)ethyl (meth)acrylate, 2-(4-methoxyphenyl)ethyl (meth)acrylate, 2-(4-cyclohexylphenyl)ethyl (meth)acrylate, 2-(2-chlorophenyl)ethyl (meth)acrylate, 2-(3-chlorophenyl)ethyl (meth)acrylate, 2-(4-chlorophenyl)ethyl (meth)acrylate, 2-(4-bromophenyl)ethyl (meth)acrylate, 2-(3-phenylphenyl)ethyl (meth)acrylate, 2-(4-benzylphenyl)ethyl (meth)acrylate, o-phenylphenoxyethyl acrylate and isobornyl acrylate; difunctional (meth)acrylate monomers such as dicyclopentyl di(meth)acrylate, caprolactone-modified dicyclopentyl di(meth)acrylate, alkylated cyclohexyl di(meth)acrylate, tricyclodecane dimethanol (meth)acrylate, dimethylol dicyclopentane di(meth)acrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, bisfluorene diacrylate, bisphenol-modified fluorene diacrylate, phenyl-modified urethane diacrylate and bisfluorene-modified urethane diacrylate; trifunctional or polyfunctional (meth)acrylate monomers such as trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated-trimethylolpropane tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, glycerol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, bis-trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, bis-trimethylolpropane tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, bis-trimethylolpropane penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate and bis-trimethylolpropane hexa(meth)acrylate; or any combination thereof.

[0106] In some exemplary embodiments, examples of acrylic monomers include Compound 1 (2-ethylhexyl acrylate), Compound 2 (butyl acrylate), Compound 3 (vinyl acetate), Compound 4 (methyl methacrylate), Compound 5 (ethyl acrylate), Compound 6 (methyl acrylate), Compound 7 (benzyl acrylate), Compound 8 (phenoxyethyl acrylate), Compound 9 (acrylic acid), Compound 10 (2-hydroxyethyl methacrylate), Compound 11 (glycidyl methacrylate), Compound 12 (acetoacetoxyethyl methacrylate), and Compound 13 (2-hydroxyethyl acrylate):

[0107]

[0108] Based on 100 parts by weight of the curable composition 100, Figure 1 the amount of the curable material 120 in the curable composition 100 shown can be in the range of about 10 parts by weight to about 99.5 parts by weight, about 50 parts by weight to about 99 parts by weight, or about 70 parts by weight to about 98 parts by weight. When the amount of the curable material 120 is within any of these ranges described above, an exposed portion can be effectively formed during the exposure for curing the curable composition 100, thereby forming a cured material 200 having excellent strength.

[0109] Curable composition 100

[0110] Figure 1 the curable composition 100 can include the above-described complex 110 containing an oxide and the curable material 120. Based on 100 parts by weight of the curable material 120, Figure 1 the amount of the complex 110 containing an oxide in the curable composition 100 can be in the range of about 0.01 parts by weight to about 20 parts by weight, about 0.1 parts by weight to about 10 parts by weight, or about 0.5 parts by weight to about 5 parts by weight. When the amount of the complex 110 containing an oxide is within any of these ranges described above, Figure 5 the cured material 200 can have excellent elasticity, flexibility, and / or resilience and excellent optical properties.

[0111] In an exemplary embodiment, the difference in refractive index (absolute value) between the curable material 120 and the oxide core 111 can be in the range of about 0.01 to about 0.5, about 0.01 to about 0.4, or about 0.02 to about 0.3. In one or more exemplary embodiments, the refractive index of the curable material 120 can be less than the refractive index of the oxide core 111.

[0112] When the refractive index of the curable material 120 and the refractive index of the oxide core 111 are within any of the ranges described above, multiple reflections and / or scattering of light incident on Figure 5 the curable material 200 can be effectively caused, thereby allowing the production of a curable material 200 having excellent optical properties.

[0113] As used herein, the term "refractive index" refers to the absolute refractive index with respect to the D line of sodium (Na) (λ = 589 nm, yellow). For example, the term "refractive index" can be, for example, an absolute refractive index measured at a temperature of 25 °C and a relative humidity of 50% using light with a wavelength of 589 nm according to the Cauchy Film Model by using a refractive index measuring instrument (e.g., an ellipsometer (sold under the trade name M-2000 Ellipsometer by J.A. Woollam of Lincoln, Nebraska)).

[0114] The term "refractive index of the curable material 120" refers to: 1) when the curable material 120 is composed of one type of compound, the refractive index of that one type of compound; or 2) when the curable material 120 is a mixture of at least two different types of compounds, the refractive index of the compound having the largest amount among the at least two different types of compounds. For example, i) when the curable material 120 is a mixture of compound A, compound B, and compound C, ii) when compound A, compound B, and compound C have amounts (parts by weight) of a, b, and c, respectively, and iii) when a > b > c, the refractive index of the curable material 120 can be the refractive index of compound A.

[0115] When the curable material 120 is a mixture of at least two different types of compounds and two or more compounds have the largest amount among the at least two different types of compounds, the refractive index of the curable material 120 can be the average of the refractive indices of the compounds having the largest amount. For example, i) when the curable material 120 is a mixture of compound A, compound B, and compound C, ii) when compound A, compound B, and compound C have amounts (parts by weight) of a, b, and c, respectively, and iii) when a > b > c, the refractive index of the curable material 120 can be the average of the refractive indices of compound A and compound B.

[0116] Table 1 shows the refractive indices of the following materials: 2-ethylhexyl acrylate, isobornyl acrylate, acrylic acid, methyl methacrylate, and 2-hydroxyethyl acrylate, which are exemplary embodiments of the curable material 120, respectively; Al 2 O 3 and SiO 2; and TiO used in Membrane A described herein 2 .

[0117] Table 1

[0118]

[0119]

[0120] For example, as shown in Table 1, in "Curable Composition 1", since SiO 2 (i.e., Oxide Core 111) has a refractive index of 1.45, and 2-ethylhexyl acrylate, which is present in the largest amount (60 parts by weight, based on 100 parts by weight of "Curable Composition 1") in the curable material 120, has a refractive index of 1.43, the difference between the refractive index of the curable material 120 and the refractive index of the oxide core 111 in "Curable Composition 1" is 0.02, and the refractive index of the curable material 120 in "Curable Composition 1" is less than the refractive index of the oxide core 111.

[0121] Curable composition 100 may further include any suitable polymerization initiator that can polymerize the curable material 120 described above, for example, any suitable photoinitiator.

[0122] From the perspectives of polymerization characteristics, initiation efficiency, absorption wavelength, availability, and price, the photoinitiator can be an acetophenone compound, a benzophenone compound, a triazine compound, a biimidazole compound, an oxime compound, a thioxanthone compound, or any combination thereof.

[0123] Examples of acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketone, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4-methylphenylthio)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylethenyl)phenyl]propan-1-one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, and hydroxydimethylacetophenone, etc.

[0124] Examples of benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone, etc.

[0125] Examples of triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, and the like.

[0126] Examples of bisimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl bisimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenyl bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl) bisimidazole, 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-bisimidazole, and imidazole compounds in which the phenyl groups are substituted with alkoxycarbonyl groups at the 4,4',5,5' positions, and the like.

[0127] Examples of oxime compounds include o-ethoxycarbonyl-α-oximino-1-phenylpropan-1-one and the like. Examples of thioxanthone compounds include 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like.

[0128] Examples of commercially available photoinitiators include: initiators sold under the trade names Irgacure-907, Irgacure184, Irgacure 819, Irgacure 250, Darocur 1173, Irgacure OXE 01 and Irgacure OXE 02 (available from BASF in Ludwigshafen, Germany); initiators sold under the trade names WPI-113, WPI-116, WPI-169, WPI-170, WPI-124, WPAG-638, WPAG-469, WPAG-370, WPAG-367 and WPAG-336 (available from Wako Pure Chemical Industries, Ltd. in Osaka, Japan); initiators sold under the trade names B2380, B2381, C1390, D2238, D2248, D2253, I0591, T1608, T1609, T2041 and T2042 (available from Tokyo Kasei Kogyo Co., Ltd. in Yamato Koriyama City, Japan); initiators sold under the trade names AT-6992 and At-6976 (available from ACETO in Port Washington, New York); initiators sold under the trade names CPI-100, CPI-100P, CPI101A, CPI-200K and CPI-210S (available from San-Apro Ltd. in Kyoto, Japan); initiators sold under the trade names SP-056, SP-066, SP-130, SP-140, SP-150, SP-170, SP-171 and SP-172 (available from ADEKA Corporation in Tokyo, Japan); initiators sold under the trade names CD-1010, CD-1011 and CD-1012 (available from Sartomer Company, Inc. in Exton, Pennsylvania); initiators sold under the trade names San Aid SI-60, SI-80, SI-100, SI-60L, SI-80L, SI-100L, SI-L145, SI-L150, SI-L160, SI-L110 and SI-L147 (available from Sanshin Kagaku Kogyo Co., Ltd. in Nagoya, Japan); initiators sold under the trade name PI2074 (available from Rhodia S.A. in La Defense, France); and hydroxyacetophenone, which is available from Millipore Sigma in Darmstadt, Germany, in which Merck KGaA holds a majority stake.

[0129] Based on 100 parts by weight of the curable composition 100, the amount of the photopolymerization initiator can be in the range of about 0.1 part by weight to 10 parts by weight, 0.5 part by weight to 5 parts by weight, or 0.5 part by weight to 3 parts by weight. When the amount of the photopolymerization initiator is within any of the ranges described above, an exposed portion can be effectively formed during the exposure for curing the curable composition 100 to form a cured material 200 having excellent strength.

[0130] The curable composition 100 can be composed of the curable material 120, the oxide-containing complex 110, and the photopolymerization initiator described above. In some exemplary embodiments, the curable composition 100 may further include any suitable solvent that is miscible with the curable material 120 and the oxide-containing complex 110 described above.

[0131] Examples of the curable composition 100 include solvents that include: alkylene glycol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol methyl ethyl ether; diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; alkylene glycol alkyl ether acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monopropyl ether acetate; alkoxyalkyl acetates such as methoxybutyl acetate and methoxypentyl acetate; aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerol; esters such as ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and ethyl 3-phenylpropionate; cyclic esters such as γ-butyrolactone; or any combination thereof.

[0132] Based on 100 parts by weight of the curable composition 100, the amount of the solvent can be in the range of about 20 parts by weight to about 70 parts by weight (e.g., about 30 parts by weight to about 60 parts by weight). When the amount of the solvent is within any of the ranges described above, the curable composition 100 can have excellent viscosity while maintaining high solid dispersibility in the curable composition 100.

[0133] In addition to the curable material 120, the oxide-containing complex 110, the polymerization initiator, and the solvent described above, the curable composition 100 may further include an alkali-soluble resin, a dispersant, or any combination thereof. The alkali-soluble resin can be used to dissolve the unexposed portion in an alkaline solution, so that after the exposure of the curable composition 100, the unexposed portion can be removed and the exposed portion can be retained, and the oxide-containing complex 110 can be uniformly dispersed in the curable composition 100. The alkali-soluble resin can be selected from those alkali-soluble resins having an acid value in the range of about 50 to about 200 (KOH mg / g). As used herein, the term "acid value" refers to the measured amount (usually milligrams (mg)) of potassium hydroxide required to neutralize 1 gram (g) of a polymer and is related to solubility. When the alkali-soluble resin has an acid value within the above range, excellent development speed, adhesion to the substrate, and storage stability of the curable composition 100 can be achieved.

[0134] The alkali-soluble resin can be a polymer derived from the following monomers: a carboxyl group-containing unsaturated monomer; or a polymer of monomers having an unsaturated bond capable of polymerizing with the monomer; or any combination thereof. Examples of the carboxyl group-containing unsaturated monomer can include unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, unsaturated tricarboxylic acids, or any combination thereof. Examples of the unsaturated monocarboxylic acid can include acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid, etc. Examples of the unsaturated dicarboxylic acid can include maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid, etc. Examples of the unsaturated dicarboxylic acid include acid anhydrides (e.g., maleic anhydride, itaconic anhydride, and citraconic anhydride, etc.). In addition, the unsaturated dicarboxylic acid can be its mono(2-(meth)acryloyloxyalkyl) ester, such as mono(2-acryloyloxyethyl) succinate, mono(2-methacryloyloxyethyl) succinate, mono(2-acryloyloxyethyl) phthalate, or mono(2-methacryloyloxyethyl) phthalate, etc. The unsaturated dicarboxylic acid can be, for example, ω-carboxypolycaprolactone monoacrylate or ω-carboxypolycaprolactone monomethacrylate, etc. The carboxyl group-containing monomers can be used alone or in combination of at least two of them.

[0135] In addition, the monomers copolymerizable with the carboxyl group-containing unsaturated monomer can include aromatic vinyl compounds, unsaturated carboxylic acid ester compounds, unsaturated carboxylic acid aminoalkyl ester compounds, unsaturated carboxylic acid glycidyl ester compounds, carboxylic acid vinyl ester compounds, unsaturated ether compounds, vinyl cyanide compounds, unsaturated amide compounds, unsaturated imide compounds, aliphatic conjugated diene compounds, macromonomers having a single acryloyl or single methacryloyl group at the end of the molecular chain, bulky monomers, or any combination thereof.

[0136] Based on 100 parts by weight of the curable composition 100, the amount of the alkali-soluble resin can range from about 5 parts by weight to about 80 parts by weight (e.g., from about 10 parts by weight to about 70 parts by weight). When the amount of the alkali-soluble resin is within any of the ranges described above, reduction of the film of the pixel portion in the exposed portion during development can be prevented, and thus satisfactory omission of the non-pixel portion can be obtained.

[0137] A dispersant can be used to improve the deaggregation of the oxide-containing complex 110 in the curable composition 100. The dispersant can be a resin-type dispersant, such as a phosphate ester dispersant, a urethane dispersant, or an acrylic dispersant, etc. Specifically, commercially available dispersants can include those sold under the trade names DISPER BYK-103, DISPER BYK-110, DISPER BYK-111, DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2011, DISPER BYK-2070, DISPER BYK-2150, DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, and DISPER BYK-166, which are available from Byk-Chemie GmbH in Wesseling, Germany.

[0138] Based on 100 parts by weight of the curable composition 100, the amount of the dispersant can range from about 0.1 part by weight to about 15 parts by weight (e.g., from about 1 part by weight to about 10 parts by weight). When the amount of the dispersant is within any of the ranges described above, aggregation of the oxide-containing complex 110 in the curable composition 100 can be significantly prevented.

[0139] In addition, the curable composition 100 may further include an adhesion promoter for increasing the adhesion to the substrate, a surfactant for improving the coating property, an antioxidant, an ultraviolet absorber, or any combination thereof.

[0140] Other exemplary embodiments of curable compositions

[0141] According to some exemplary embodiments, the curable composition may include:

[0142] A curable material; and

[0143] An oxide-containing complex, wherein,

[0144] The oxide-containing complex may include i) an oxide core and ii) an organic group of atoms chemically bonded to the surface of the oxide core,

[0145] The organic group may include a) a curable group capable of reacting with the curable material and b) a linking group that connects an atom on the surface of the oxide core to the curable group, and the difference (absolute value) between the refractive index of the curable material and the refractive index of the oxide core may be in the range of about 0.01 to about 0.5.

[0146] In some exemplary embodiments, the oxide-containing complex is as described herein. In some exemplary embodiments, the oxide included in the oxide core of the oxide-containing complex may be selected from any suitable oxide that satisfies the refractive index difference range between the refractive index of the curable material and the refractive index of the oxide core. In some exemplary embodiments, the curable material is as described herein.

[0147] Method for preparing curable composition 100

[0148] The method for preparing the curable composition 100 described above may include: providing an oxide-containing complex 110, which includes: i) an oxide core 111; and ii) an organic group 113 chemically bonded to an atom 111A on the surface of the oxide core 111, and

[0149] mixing the oxide-containing complex 110 with the curable material 120 to provide a curable composition 100 including the oxide-containing complex 110 and the curable material 120.

[0150] The oxide-containing complex 110 and the curable material 120 may be understood by referring to the descriptions of the oxide-containing complex 110 and the curable material 120 provided herein, respectively.

[0151] In an exemplary embodiment, providing the oxide-containing complex 110 may include reacting an oxide precursor 110' with a compound represented by Formula 2:

[0152]

[0153] wherein, in Formula 2, L 1 , a1, T 20 and a2 may be understood by referring to the descriptions of L 1 , a1, T 20 and a2, respectively, and T 11 to T 13 may each independently be a hydroxyl group or a C 1 -C 20 alkoxy group.

[0154] Different from the oxide core 111 described herein, except that the organic group 113 is not bonded to the atom on the surface of the oxide precursor 110'. Figure 3The oxide precursor 110' shown in [reference] can be understood by referring to the description of the oxide core 111 described herein. At least one hydroxyl group may be present on the surface of the oxide precursor 110', as Figure 3 shown in

[0155] The Ts in Formula 2 11 to T 13 can be hydrolyzed and thereby become silanol (*-Si-OH) groups. Due to the dehydration condensation reaction of the silanol groups with the hydroxyl groups on the surface of the oxide precursor 110', the organic group 113 (e.g., the group represented by Formula 1) can be chemically bonded to the atom 111A on the surface of the oxide core 111, as described herein.

[0156] For example, the compound represented by Formula 2 can be:

[0157] i) 3-(Trimethoxysilyl)propyl methacrylate; or

[0158] ii) a compound in which 3-(glycidyloxypropyl)trimethoxylan and poly(ethylene glycol) methacrylate are bonded to each other by an epoxy ring-opening reaction.

[0159] The reaction of the oxide precursor 110' with the compound represented by Formula 2 can be carried out in the presence of an acid catalyst. For example, the acid catalyst can include hydrochloric acid (HCl), sulfuric acid (H 2 SO 4 )), acetic acid (CH 3 COOH), nitric acid (HNO 3 ), or any combination thereof.

[0160] The solvent that can be used in the reaction between the oxide precursor 110' and the compound represented by Formula 2 can be any suitable solvent that can be mixed with the oxide precursor 110' and the compound represented by Formula 2. For example, the solvent can include water, methanol, ethanol, ethylene glycol, glycerol, or any combination thereof.

[0161] Curing material 200

[0162] According to another aspect, the curable composition 100 described above can be cured to prepare a cured material 200 of the curable composition 100. Figure 5 The cured material 200 can include those derived from those included in Figure 4The matrix material 220 of the curable material 120 in the curable composition 100. The "matrix material 220 derived from the curable material 120" can be, for example, a matrix material 220 (e.g., a polymer) modified due to the polymerization of the curable material 120 (e.g., a photopolymerizable monomer).

[0163] As Figures 3 to 5 shown, the atoms 111A on the surface of the oxide-containing complex 110 included in the curable composition 100 can be "chemically bonded" to the matrix material 220 via i) the residual group 118 resulting from the reaction between the curable group 117 in the oxide-containing complex 110 and the curable material 120 and ii) the linking group 115 in the oxide-containing complex 110.

[0164] In some exemplary embodiments, Figure 5 the residual group 118 shown can be represented by Formula 3:

[0165] *-(L 11 ) a11 -*' Formula 3

[0166] wherein, in Formula 3,

[0167] L 11 can be:

[0168] *-N(R 21 )-*', *-O-*', *-S-*' or *-C(=O)-*'; or

[0169] C 1 -C 60 alkylene, C 1 -C 60 alkoxyalkylene, C 6 -C 60 arylene or C 6 -C 60 aryloxy, all of which are unsubstituted or substituted with deuterium, a hydroxyl group, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl or any combination thereof,

[0170] * and *' can both indicate the binding sites to adjacent atoms,

[0171] R 21 can be hydrogen, deuterium, a hydroxyl group, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl or biphenyl,

[0172] a11 can be an integer from 1 to 10,000 (e.g., an integer from 1 to 5,000, or an integer from 1 to 1,000), and when a11 is 2 or greater, at least two L 11 can be the same as or different from each other,

[0173] The * in Formula 3 can indicate the binding site to the Figure 5 linking group 115 shown in, and

[0174] The *' in Formula 3 can indicate the binding site to the Figure 5 substrate material 220 shown in.

[0175] Figure 5 The substrate material 220 in the curable material 200 shown in can be chemically bonded to the oxide core 111 via i) the residual group 118 and ii) the linking group 115, thereby forming a network structure. Thus, Figure 5 the oxide core 111 in the curable material 200 is chemically bonded to the substrate material 220 via i) the residual group 118 and ii) the linking group 115. Compared with the curable material (e.g., Film B) in which the above-described substrate material and oxide core (e.g., spherical oxide particles) are not "chemically bonded to each other" and are "physically mixed" with each other, the curable material 200 can have excellent resilience when an external force is applied and / or removed.

[0176] The curable material 200 can be used in various applications such as adhesive members, insulating members, optical members, protective members, and peeling members depending on the substrate material 220, all of which can be particularly suitable for use in electronic devices and articles. For example, the substrate material 220 in the curable material 200 can be an adhesive material. When the substrate material 220 in the curable material 200 is an adhesive material, the curable material 200 can be an adhesive member. The curable material 200 can be in the form of a film. For example, the thickness of the film can be in the range of about 0.1 μm to about 700 μm, about 1 μm to about 600 μm, or about 5 μm to about 500 μm (see, for example, Films 1 to 3 in the examples described herein).

[0177] The curable material 200 can have excellent light transmittance. For example, the light transmittance of the curable material 200 with respect to light having a maximum emission wavelength of 600 nm is 96% (96%) or higher, for example, about 97% to about 100%. Therefore, the curable material 200 can be used in various devices having a light-emitting member (e.g., an organic light-emitting device or a quantum dot light-emitting device, etc.).

[0178] Method for preparing curing material 200

[0179] A method for preparing the curable material 200 can include:

[0180] Provide a curable composition 100 on a substrate; and

[0181] Cure the curable composition 100.

[0182] When curing the curable composition 100, a chemical reaction can occur between the curable group 117 in the oxide-containing complex 110 and the curable material 120. Therefore, a residual group 118 as shown in Figure 5 can be formed. Thus, the atoms 111A on the surface of the oxide core 111 can be chemically bonded to the matrix material 220 via i) the residual group 118 and ii) the linking group 115 in the oxide-containing complex 110.

[0183] The substrate provided with the curable composition 100 can be used in various ways depending on the application field. For example, when using the cured material 200 as an adhesive member for bonding electronic device components to a cover window, the substrate can be on top of the electronic device components.

[0184] The curing of the curable composition 100 can be carried out by photopolymerization, and exposure can be carried out for photopolymerization. The exposure can be exposure to ultraviolet light. The curing of the curable composition 100 can also include baking before and / or after exposure to remove a part of the solvent in the curable composition 100.

[0185] Article or device including curing material 200

[0186] According to some exemplary embodiments, articles and devices can include a cured material 200. The article can be a film laminate including the cured material 200. For example, the film laminate can be an antistatic film laminate, which includes a substrate, a cured material 200, and an antistatic film sequentially stacked in any of the devices described herein.

[0187] The device can be various electronic devices, such as display devices, cellular phones, and lighting devices, etc. For example, the electronic device can be a light-emitting diode such as an organic light-emitting device (OLED) or a quantum dot light-emitting device (QLED) for use in a display or other devices.

[0188] In an exemplary embodiment, the device can be a flexible device, a foldable device, or a rollable device where the application and removal of external force are relatively frequent. Hereinafter, the curable composition 100, the cured material 200, and their preparation methods will be described in more detail by examples and / or comparative examples.

[0189] Examples

[0190] Synthesis of oxide - containing complex 1

[0191] Mix 50 milliliters (mL) of ethanol and 2.5 g of SiO 2 particles (with a diameter D15 of 20 nm) together, and then stir for 30 minutes. Homogenize the mixture in an ice - water bath using a homogenizer for 30 minutes. Then, dropwise add a mixture of 2.5 g of 3 - (trimethoxysilyl)propyl methacrylate (MEMO) and 1 mL of water, and then stir for 2 hours. Adjust the pH of the resulting mixture to 2 using an aqueous hydrochloric acid solution (with a concentration of 38 mol%). Then, carry out the reaction under reflux at a stirring rate of 800 revolutions per minute (rpm) and at a temperature of 60 °C. Wash the resulting mixture with ethanol and water, and then perform centrifugation (at 4,000 rpm) for 30 minutes, and then dry at a temperature of 60 °C for 4 hours, thereby preparing an oxide - containing complex 1.

[0192] Synthesis of oxide - containing complex 2

[0193] Synthesize an oxide - containing complex 2 in a manner substantially the same as the synthesis of the oxide - containing complex 1, except that 3.375 g of MEMO is used.

[0194] Synthesis of oxide - containing complex 3

[0195] Synthesize an oxide - containing complex 3 in a manner substantially the same as the synthesis of the oxide - containing complex 1, except that 6.75 g of MEMO is used.

[0196] Synthesis of oxide - containing complex A

[0197] Except for using 2.5 g of TiO 2 particles (with a diameter D15 of 20 nm) to replace SiO 2 particles, synthesize an oxide - containing complex A in a manner substantially the same as the synthesis of the oxide - containing complex 2.

[0198] Preparation of curable composition 1

[0199] Mix the oxide - containing complex 1 (1 part by weight), curable monomer 1 (60 parts by weight), curable monomer 2 (20 parts by weight), curable monomer 3 (4 parts by weight), curable monomer 4 (4 parts by weight), curable monomer 5 (10 parts by weight), and a photoinitiator (1 part by weight) together, and then stir for 30 minutes using a size - mixing machine, thereby preparing a curable composition 1. Curable monomers 1 to 5 and the photoinitiator can be understood by referring to the descriptions of curable monomers 1 to 5 and the photoinitiator provided herein.

[0200] · Curable monomer 1: 2 - ethylhexyl acrylate (Aldrich Company)

[0201] · Curable monomer 2: Isobornyl acrylate (Aldrich Company)

[0202] · Curable monomer 3: Acrylic acid (Aldrich Company)

[0203] · Curable monomer 4: Methyl methacrylate (Aldrich Company)

[0204] · Curable monomer 5: 2-Hydroxyethyl acrylate (Aldrich Company)

[0205] · Photoinitiator: Hydroxy-dimethylacetophenone (Aldrich Company)

[0206] Preparation of curable compositions 2, 3 and A

[0207] Curable compositions 2, 3, and A are prepared in a manner that is substantially the same as the manner of preparing curable composition 1, except that complexes 2, 3, and A of oxides are used separately to replace complex 1 of oxides.

[0208] Preparation of curable composition B

[0209] Except for using 2.5 g of SiO 2 particles (with a diameter D15 of 20 nm) to replace complex 1 of oxides, curable composition B is prepared in a manner that is substantially the same as the manner of preparing curable composition 1.

[0210] Preparation of curable composition C

[0211] Curable composition C is prepared in a manner that is substantially the same as the manner of preparing curable composition 1, except that complex 1 of oxides is not used.

[0212] Table 2

[0213]

[0214] Preparation of film 1

[0215] Curable composition 1 is provided into the space between two polyethylene terephthalate (PET) films using a roll-to-roll coater. Then, pre-baking is performed for 1 minute at a temperature of 100 °C using a hot plate, and UV light (365 nm) is incident with an exposure dose of 200 millijoules per square centimeter (mJ / cm 2 ) using an exposure device. After that, post-baking is performed for 30 minutes at a temperature of 180 °C in a heating furnace in a nitrogen atmosphere, thereby preparing film 1 with a thickness of 50 μm.

[0216] Preparation of films 2, 3, A, B and C

[0217] Membranes 2, 3, A, B, and C were prepared in substantially the same manner as for preparing Membrane 1, except that curable compositions 2, 3, A, B, and C were used in place of curable composition 1.

[0218] Evaluation example 1 (Measurement of light transmittance)

[0219] The light transmittance (%) of Membranes 1, 2, 3, A, B, and C with respect to light having a maximum emission wavelength of 600 nm was measured using a UV-visible spectrometer. The results are shown in Table 3. The light transmittance of each membrane is shown as a value (%) relative to the light transmittance of Membrane C.

[0220] Table 3

[0221]

[0222]

[0223] Referring to the results in Table 3, Membranes 1 to 3 have unexpectedly and surprisingly excellent light transmittance compared to Membranes A and B.

[0224] Evaluation example 2 (Measurement of peel strength)

[0225] Samples of Membranes 1, 2, 3, A, B, and C were prepared according to the ASTM D3359-17 standard for the 180° peel test method. Then, the peel strength (N / 25 mm) was measured at a speed of 300 mm / min. The results are shown in Table 4. The peel strength of each membrane is shown as a value (%) relative to the peel strength of Membrane C.

[0226] Table 4

[0227]

[0228]

[0229] Referring to the results in Table 4, Membranes 1 to 3 have unexpectedly and surprisingly excellent peel strength compared to Membranes A and B.

[0230] Evaluation example 3 (Measurement of modulus at break point)

[0231] Samples of films 1, 2, 3, A, B, and C were prepared according to the ASTM D882-18 standard for tensile test methods. Then, the modulus at the break point in kilopascals (kPa) was measured using a stress-strain diagram at a rate of 50 mm / min. The results are shown in Table 5. The modulus at the break point of each film is shown as a value (%) relative to the modulus at the break point of film C.

[0232] Table 5

[0233]

[0234] Referring to the results in Table 5, films 1 to 3 have a modulus at the break point that is superior to film A and equal to or superior to film B.

[0235] Evaluation example 4 (Measurement of relaxation rate)

[0236] Samples of films 1, 2, 3, A, B, and C were prepared according to the ASTM D882-18 standard for stress relaxation test methods. Next, the relaxation rate (%) was measured under the given conditions of a rate of 100 mm / min and a strain of 200%. The results are shown in Table 6. The relaxation rate of each film is shown as a value (%) relative to the relaxation rate of film C.

[0237] Table 6

[0238]

[0239] Referring to the results in Table 6, films 1 to 3 have unexpectedly and surprisingly excellent relaxation rates compared to films A, B, and C.

[0240] Although certain exemplary embodiments and implementations have been described herein, other embodiments and modifications will be apparent from this description. Accordingly, the inventive concept is not limited to these embodiments, but rather to the broader scope of the appended claims and various obvious modifications and equivalent arrangements that will be apparent to those of ordinary skill in the art.

Claims

1. A curable composition, the curable composition comprises: a curable material; and an oxide-containing complex; wherein the oxide-containing complex comprises: i) an oxide core; and ii) an organic group, the organic group being chemically bonded to an atom on the surface of the oxide core, the organic group comprises: a) a curable group capable of reacting with the curable material; and b) a linking group that links the atom on the surface of the oxide core to the curable group, and the oxide core comprises alumina, silica or a combination thereof, and the oxide core has a refractive index of 1.2 to 2.5, the curable material has a refractive index of 1.2 to 2.0, and the difference between the refractive index of the curable material and the refractive index of the oxide core is 0.01 to 0.

5.

2. The curable composition according to claim 1, wherein, the oxide core has a diameter D15 of 1 nm to 50 nm.

3. The curable composition according to claim 1, wherein, the organic group has Formula 1: wherein, in Formula 1, L 1 is: *-N(R 11 )-*, *-O-*, *-S-*, or *-C(=O)-*; or C 1 -C 60 Alkylene, C 1 -C 60 Alkoxy, C 6 -C 60 Arylene or C 6 -C 60 Aryloxy, all unsubstituted or substituted with deuterium, hydroxyl, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl or any combination thereof; * and *' each indicate a binding position to an adjacent atom; R 11 is hydrogen, deuterium, hydroxyl, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl or biphenyl; a1 is an integer from 1 to 10,000, and when a1 is 2 or greater, at least two Ls 1 are the same as or different from each other; T 20 is a curable group; a2 is an integer from 1 to 10, and when a2 is 2 or greater, at least two Ts 20 are the same as or different from each other; and T 1 and T 2 are each independently hydrogen, deuterium, a hydroxyl group, C 1 -C 20 -alkyl, C 1 -C 20 -alkoxy, phenyl, biphenyl, an oxygen atom bonding to a silicon atom incorporated in an adjacent linking group, or a bonding site of oxygen provided between the linking group and an adjacent linking group; wherein, in Formula 1, * indicates a binding position to the atom on the surface of the oxide core.

4. The curable composition according to claim 3, wherein, As the T 20 The curable group is a group represented by one of Formula 1-2(1) to Formula 1-2(8): wherein, in Formulas 1-2(1) to 1-2(8), R 1 to R 5 are each independently hydrogen, deuterium, a hydroxyl group, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, phenyl or biphenyl; and * indicates a binding position to the linking group.

5. The curable composition according to claim 1, wherein, the oxide core and the organic group in the oxide-containing complex have a weight ratio between 10:1 and 1:

10.

6. A method for preparing a curable composition, the method comprising the following steps: providing an oxide-containing complex, the oxide-containing complex comprises: i) an oxide core having a refractive index of 1.2 to 2.5; and ii) an organic group, the organic group being chemically bonded to an atom on the surface of the oxide core; and mixing the oxide-containing complex with a curable material having a refractive index of 1.2 to 2.0 to provide a curable composition comprising the oxide-containing complex and the curable material, and the difference between the refractive index of the curable material and the refractive index of the oxide core is 0.01 to 0.5; wherein the organic group comprises: a) a curable group capable of reacting with the curable material; and b) a linking group that links the atom on the surface of the oxide core to the curable group; and the oxide core comprises alumina, silica or a combination thereof.

7. The method according to claim 6, wherein, the step of providing the oxide-containing complex comprises reacting an oxide precursor with a compound represented by Formula 2: wherein, in Formula 2, L 1 is: *-N(R 11 )-*, *-O-*, *-S-*, or *-C(=O)-*; or C 1 -C 60 Alkylene, C 1 -C 60 Alkoxy, C 6 -C 60 Arylene or C 6 -C 60 Aryloxy, all unsubstituted or substituted with deuterium, hydroxyl, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl or any combination thereof; * and *' each indicate a binding position to an adjacent atom; R 11 is hydrogen, deuterium, a hydroxyl group, C 1 -C 20 -alkyl, C 1 -C 20 -alkoxy, phenyl or biphenyl; a1 is an integer from 1 to 10,000, and when a1 is 2 or greater, at least two Ls 1 are the same as or different from each other; T 20 is a curable group; a2 is an integer from 1 to 10, and when a2 is 2 or greater, at least two Ts 20 are the same as or different from each other; and T 11 to T 13 are each independently a hydroxyl group or a C 1 -C 20 alkoxy group.

8. A cured material, wherein, the cured material comprises the curable composition according to any one of claims 1 to 5.

9. The cured material according to claim 8, wherein, The cured material includes a matrix material derived from the curable material, and atoms on the surface of the oxide core in the oxide-containing complex are chemically bonded to the matrix material via i) a residual group resulting from the reaction between the curable group in the oxide-containing complex and the curable material and ii) the linking group in the oxide-containing complex.

10. The cured material according to claim 9, wherein, the matrix material includes a binder material.

11. The cured material according to claim 9, wherein, the cured material is in the form of a film.

12. The cured material according to claim 11, wherein, the film has a thickness of 0.1 μm to 700 μm.

13. The cured material according to claim 9, wherein, the light transmittance with respect to light having a maximum emission wavelength of 600 nm is 96% or higher.

14. A method for preparing a cured material, wherein, the method includes the following steps: providing a curable composition according to any one of claims 1 to 5 on a substrate; and curing the curable composition.

15. The method according to claim 14, wherein, the step of curing the curable composition includes exposing the curable composition to ultraviolet light.

16. An electronic device, wherein, the electronic device includes a cured material according to any one of claims 8 to 13.

17. The electronic device according to claim 16, wherein, the electronic device includes a flexible, foldable or rollable electronic device.

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