JP7763343B2 - Organic-inorganic hybrid composition and adhesive film containing the same - Google Patents

Description

The present invention relates to an organic-inorganic hybrid composition and an adhesive film containing the same.

Optical clear adhesive (OCA) film is a transparent adhesive film used to bond optical components. Recently, demand for touch panels has rapidly increased in areas such as smartphones, tablet PCs, portable game consoles, and automotive navigation devices, leading to a rapid increase in demand for OCA film, which is used to bond touch panels to other optical components.

Display devices equipped with touch panels typically have a laminated structure of optical components, such as a display panel such as a liquid crystal panel, a touch panel body with a transparent conductive film made of indium tin oxide (ITO) or the like on its surface, and a cover panel that protects the transparent conductive film. Optically transparent adhesives can be used in the form of a film to bond the optical components together. With increasing demand for OCA films, interest in the adhesive materials used here is growing.

Conventional optically transparent adhesives have been made from organic materials such as silicone resins, polyurethane resins, and olefin resins. However, when such organic-based optically transparent adhesives are used in display optical materials, problems arise in that the optical properties are affected depending on the difference in refractive index between the laminated layers.

To address this issue, technology has been developed to increase the refractive index by mixing inorganic particles into organic-based optically transparent adhesives, but compatibility becomes an issue when mixing organic and inorganic particles.

The above-mentioned background art was held or acquired by the inventors in the process of deriving the contents of this specification, and is not necessarily publicly known art that was disclosed to the general public prior to the filing of this application.

To solve the above-mentioned problems, the present invention provides a surface treatment agent for organic-inorganic hybrid compositions.

According to one embodiment of the present invention, an organic-inorganic hybrid composition is provided.

However, the problems solved by the present invention are not limited to those mentioned above, and additional problems not mentioned will be clearly understood by those with ordinary skill in the art from the description below.

An organic-inorganic hybrid composition according to one embodiment of the present invention comprises inorganic particles whose surfaces have been modified with a surface treatment agent and an acrylic monomer, with the surface-modified inorganic particles and the acrylic monomer having a weight ratio of 1:1 to 2:1.

According to one embodiment, the inorganic particles may include at _least one selected from the group consisting of _ZrO2 , _SiO2 , _{Al2O3 , CeO2} , ZnO, _V2O5TiO2 , _BaTiO3 , _SrTiO3 , _BaTiO3 , _PbTiO3 , _{PbZrO3 ,} Pb(Zr,Ti _{) O3} (PZT), Pb1-xLaxZr1-yTiyO3 (PLZT), (1 _{- x )} Pb(Mg1 _/3Nb2 / ₃ ) _{O3- xPbTiO3 ( PMN} -PT), _HfO2 , and BN.

According to one embodiment, the inorganic particles have a diameter of 10 nm to 200 nm and a specific surface area of 1 m ² /g to 250 m ² /g.

According to one embodiment, the surface-modified inorganic particles comprise 40% to 50% by weight of the composition.

According to one embodiment, the acrylic monomer may include at least one selected from the group consisting of butyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, and 4-acryloyl morpholine.

In one embodiment, the acrylic monomer comprises 50% to 60% by weight of the composition.

According to one embodiment, the surface treatment agent is a copolymer of a silane-based monomer and a methacrylate-based monomer.

According to one embodiment, the silane-based monomer may include at least one selected from the group consisting of silane, _C1 - _C20 alkylsilane, alkoxysilane, isocyanatesilane, aminosilane, epoxysilane, acrylsilane, mercaptosilane, fluorine silane, methacryloxy silane, vinylsilane, phenylsilane, chlorosilane, and silazane. The methacrylate-based monomer may include at least one selected from the group consisting of 2-hydroxyethyl methacrylate (2-HEMA), 2-hydroxypropyl methacrylate (2-HPMA), and 2-hydroxy-1-methylethyl methacrylate.

According to one embodiment, the surface treatment agent may include a compound represented by any one of the following chemical formulas 1 to 3.

[Chemical formula 1]

[Chemical formula 2]

[Chemical formula 3]

(wherein R ₁ to R ₃ each contain at least one of H, a saturated or unsaturated, linear or branched C ₁ -C ₂₀ alkyl group, a hydroxyl group, a silane group, and an alkoxysilane group, and R ₄ contains H or a hydroxyl group.)

According to one embodiment, the surface treatment agent may be included in an amount of 10 to 30 parts by weight per 100 parts by weight of inorganic particles.

According to one embodiment, the composition may further comprise a dispersant containing at least one functional group selected from the group consisting of a carboxyl group, a phosphate group, a phosphonate group, a sulfonic acid group, and a phenolic hydroxyl group.

According to one embodiment, the dispersant may be included in an amount of 1 to 10 parts by weight per 100 parts by weight of the composition.

According to one embodiment, the composition further comprises a dispersion solvent, which may include at least one selected from the group consisting of methyl ethyl ketone (MEK), ethanol, methanol, acetonitrile, toluene, tetrahydrofuran (THF), propylene glycol monomethyl ether acetate (PGMEA), and ethyl acetate.

According to one embodiment, the weight ratio of the surface-modified inorganic particles to the dispersion solvent is 1:1 to 1:2.

According to one embodiment, the dispersion solvent comprises 30% to 60% by weight of the composition.

According to one embodiment, the composition has a refractive index of 1.50 to 1.80, a viscosity of 180 cPs to 20,000 cPs (at 25°C), and a haze of 15% or less.

An adhesive film according to another embodiment of the present invention is an adhesive film manufactured using a composition, which includes inorganic particles surface-modified with a surface treatment agent and an acrylic monomer, and the surface-modified inorganic particles and the acrylic monomer may have a weight ratio of 1:1 to 2:1.

The present invention provides a surface treatment agent for organic-inorganic hybrid compositions.

According to one embodiment of the present invention, an organic-inorganic hybrid composition can be provided.

The following embodiments are described in detail with reference to the accompanying drawings. However, various modifications may be made to the embodiments, and the scope of the patent application is not limited or restricted by such embodiments. All modifications, equivalents, or alternatives to the embodiments should be understood to be included in the scope of the patent.

The terms used in the embodiments are for explanatory purposes only and should not be construed as limiting. The singular expressions include the plural expressions unless the context clearly dictates otherwise. In this specification, the terms "include" or "have" indicate the presence of features, numbers, steps, operations, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the possibility of the presence or addition of one or more other features, numbers, steps, operations, components, parts, or combinations thereof.

Unless otherwise defined, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by a person of ordinary skill in the art to which the present invention pertains. Commonly used, predefined terms should be interpreted to have a meaning consistent with the meaning they have in the context of the relevant art, and should not be interpreted as having an ideal or overly formal meaning unless expressly defined herein.

In addition, when describing components of an embodiment, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are used to distinguish the component from other components, and do not limit the nature, order, or sequence of the components. When a component is described as being "coupled," "coupled," or "connected" to another component, it should be understood that the component may be directly coupled or connected to the other component, but that additional components may be "coupled," "coupled," or "connected" between each component.

Component elements that share functions with components included in one embodiment will be described using the same names in other embodiments. Unless otherwise specified, descriptions given in one embodiment also apply to other embodiments, and specific descriptions will be omitted to the extent that they overlap.

An organic-inorganic hybrid composition according to one embodiment of the present invention may include inorganic particles whose surfaces have been modified with a surface treatment agent and an acrylic monomer. According to one embodiment, the organic-inorganic hybrid composition may be cured to form an adhesive film. According to the present invention, the organic-inorganic hybrid composition may provide an inorganic particle dispersion composition that is optically transparent or substantially optically transparent.

In one embodiment, the surface of the inorganic particles is modified using a surface treatment agent to improve the dispersibility of the inorganic particles, and by dispersing the particles evenly within the composition, an optically transparent inorganic particle dispersion composition can be provided.

According to one embodiment, the surface-modified inorganic particles and the acrylic monomer may have a weight ratio of 1:1 to 2:1. According to one embodiment, it is preferable that the weight of the acrylic monomer is the same as or greater than the weight of the surface-modified inorganic particles.

In one embodiment, the inorganic particles may be metal oxides. In one embodiment, the inorganic particles may be contained in a transparent polymer resin as metal oxides to increase the refractive index.

According to one embodiment, the inorganic particles may include at least one selected from the group consisting of _ZrO2 , _SiO2 , _{Al2O3 , CeO2} , ZnO, _V2O5TiO2 , _BaTiO3 , _SrTiO3 , _BaTiO3 , _PbTiO3 , _PbZrO3 , Pb(Zr,Ti _{) O3} (PZT), _Pb1 -xLaxZr1-yTiyO3 (PLZT), (1 _{- x )} Pb ₍ Mg1 _/ 3Nb2/ ₃ ) _{O3- xPbTiO3} (PMN-PT), _HfO2 , _and BN.

According to one embodiment, the inorganic particles may preferably include zirconia ( _ZrO2 ), which is transparent, has a high Abbe number, and has excellent mechanical strength and thermal stability, making it suitable for the composition according to one embodiment of the present invention.

According to one embodiment, the inorganic particles are nano-inorganic particles. According to one embodiment, the diameter of the inorganic particles may be 10 nm to 200 nm. Here, the diameter of the inorganic particles refers to the average diameter of the inorganic particles. Also, the diameter of the inorganic particles refers to the diameter of inorganic particles that have not been surface-modified with a surface treatment agent.

According to one embodiment, the diameter of the inorganic particles may be 10 nm or more, 20 nm or more, 30 nm or more, 40 nm or more, 50 nm or more, 60 nm or more, 70 nm or more, 80 nm or more, 90 nm or more, 100 nm or more, 110 nm or more, 120 nm or more, 130 nm or more, 140 nm or more, 150 nm or more, 160 nm or more, 170 nm or more, 180 nm or more, or 190 nm or more; or 200 nm or less, 190 nm or less, 180 nm or less, 170 nm or less, 160 nm or less, 150 nm or less, 140 nm or less, 130 nm or less, 120 nm or less, 110 nm or less, 100 nm or less, 90 nm or less, 80 nm or less, 70 nm or less, or 60 nm or less, or may be included in a range between any two values selected from the above-mentioned numerical values.

According to one embodiment, if the diameter of the inorganic particles is less than 10 nm, dispersion becomes difficult due to the increased surface energy of the inorganic particles, and if the diameter exceeds 200 nm, a scattering effect occurs, reducing the visibility of the adhesive film and increasing the thickness of the adhesive film.

According to one embodiment, the specific surface area of the inorganic particles may be 1 m ² /g to 250 m ² /g. Here, the specific surface area of the inorganic particles refers to the average specific surface area of the inorganic particles. The specific surface area of the inorganic particles may be measured by measuring the specific surface area of inorganic particles that have not been surface-modified with a surface treatment agent.

According to one embodiment, the specific surface area of the inorganic particles is 1 m ² /g or more, 10 m ² /g or more, 30 m ² /g or more, 50 m ² /g or more, 70 m ² /g or more, 90 m ² /g or more, 110 m ² /g or more, 130 m ² /g or more, 150 m ² /g or more, 170 m ² /g or more, 190 m ² /g or more, 210 m ² /g or more, or 230 m ² /g or more; or 250 m ² /g or less, 230 m ² /g or less, 210 m ² /g or less, 190 m ² /g or less, 170 m ^{2 /g or less, 150 m 2 /} g or less, 130 m ² /g or less, 110 m 2 /g or less, 90 m ² /g or more ^. /g or less, or 70 m ² /g or less, or may be included in a range between any two values selected from the aforementioned numerical values.

According to one embodiment, if the specific surface area of the inorganic particles exceeds the above numerical range, transmittance may decrease, quality may deteriorate due to scattering, and agglomerations may form.

According to one embodiment, the surface-modified inorganic particles may comprise 40% to 50% by weight of the composition. According to another embodiment, the surface-modified inorganic particles may comprise 40% to 45% by weight, or 45% to 50% by weight.

According to one embodiment, if the surface-modified inorganic particles in the composition are less than 40% by weight, the relative proportion of inorganic particles in the composition will be low, resulting in a decrease in the refractive index and brightness of the composition; if they are more than 50% by weight, cloudiness may occur when the adhesive film is subsequently manufactured.

According to one embodiment, the acrylic monomer may include at least one selected from the group consisting of butyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, and 4-acryloyl morpholine.

An adhesive film can be produced by curing a composition according to one embodiment of the present invention, and by using an acrylic monomer, it is possible to produce an adhesive film that is flexible yet optically excellent.

According to one embodiment, the acrylic monomer may be 50% to 60% by weight of the composition. According to another embodiment, the acrylic monomer may be 50% to 55% by weight, or 55% to 60% by weight.

According to one embodiment, if the acrylic monomer is less than 50% by weight of the composition, the proportion of inorganic particles increases, resulting in an increase in viscosity; if it exceeds 60% by weight, the proportion of inorganic particles decreases, resulting in a decrease in the refractive index and brightness of the adhesive film, and cloudiness may occur.

According to one embodiment, the surface treatment agent may be a copolymer of a silane-based monomer and a methacrylate-based monomer. Specifically, the surface treatment agent may be a random copolymer of a silane-based monomer and a methacrylate-based monomer.

According to one embodiment, the silane-based monomer may include at least one selected from the group consisting of silane, _C1 - _C20 alkylsilane, alkoxysilane, isocyanatesilane, aminosilane, epoxysilane, acrylsilane, mercaptosilane, fluorine silane, methacryloxy silane, vinylsilane, phenylsilane, chlorosilane, and silazane.

According to one embodiment, the silane-based monomer is specifically a vinyl group-containing silane-based monomer including at least one selected from the group consisting of vinyltrimethoxysilane (vinyltrimethoxysilane), vinyltriethoxysilane (vinyltriethoxysilane), and vinyltris(2-methoxyethoxy)silane (vinyltris(2-methoxyethoxy)silane), 3-methacryloxypropyltrimethoxysilane (3-methacryloxypropyltrimethoxysilane, MPTMS), 3-methacryloxypropyltriethoxysilane (3-methacryloxypropyltriethoxysilane, MPTES), 3-methacryloxypropylmethyldimethoxysilane (3-methacryl a methacryloxy group-containing silane-based monomer containing at least one selected from the group consisting of 3-acryloxypropyltrimethoxysilane (APTMS), 3-acryloxypropyltriethoxysilane (APTMS), and 3-methacryloxypropylmethyldiethoxysilane (APTMS), an acetoxy group-containing silane-based monomer containing vinyltriacetoxysilane (APTMS), an acryloxy group-containing silane-based monomer containing at least two of 3-acryloxypropyltrimethoxysilane (APTMS), and 3-acryloxypropyltriethoxysilane (APTMS), and an acryloxy group-containing silane-based monomer containing at least two of 3-glycidoxypropyltrimethoxysilane (APTMS), and an acryloxy group-containing silane-based monomer containing at least one of 3-glycidoxypropyltrimethoxysilane (APTMS), and an acryloxy group-containing silane-based monomer containing at least one of 3-glycidoxypropyltriethoxy ... 3-glycidoxypropyltrimethoxysilane (GPTMS), 3-glycidoxypropyltriethoxysilane (GPTES), 3-glycidoxypropylmethyldimethoxysilane (3-glycidoxypropylmethyldimethoxysilane), 3-glycidoxypropyltriethoxysilane (GPTMS), 3-glycidoxypropyltriethoxysilane (GPTES), 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltriethoxysilane an epoxy group-containing silane monomer containing at least one selected from the group consisting of 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, vinyltrichlorosilane, Chloro group-containing silane monomers including vinyltrichlorosilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, a mercapto group-containing silane-based monomer containing at least one selected from the group consisting of 3-mercaptopropylmethyldiethoxysilane, 3-mercaptopropylmethyldiethoxysilane, 3-trimethoxysilylpropyl succinic anhydride, 3-triethoxy ... anhydride), 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and N-2-(aminoethyl)-3-aminopropyltrimethoxysilane. The compound may include at least one selected from the group consisting of an amino group-containing silane monomer, and an isocyanate group-containing silane monomer, including 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, or both. According to one embodiment, the silane monomer may be a silane coupling agent.

According to one embodiment, the methacrylate monomer may include at least one selected from the group consisting of 2-hydroxyethyl methacrylate (2-HEMA), 2-hydroxypropyl methacrylate (2-HPMA), and 2-hydroxy-1-methylethyl methacrylate.

According to one embodiment, the surface treatment agent may include a compound represented by any one of the following chemical formulas 1 to 3:

[Chemical formula 1]

[Chemical formula 2]

[Chemical formula 3]

Here, R ₁ to R ₃ each include at least one of H, a saturated or unsaturated linear or branched C ₁ -C ₂₀ alkyl group, a hydroxyl group, a silane group, and an alkoxysilane group, and R ₄ may include H or a hydroxyl group.

According to one embodiment, for example, R ₁ to R ₃ may each comprise at least one selected from the group consisting of a C ₂ -C ₁₂ alkyltrimethoxysilane group, a C ₂ -C ₁₂ alkyltriethoxysilane group, and a C _{2 -C 12} alkyldimethoxyethoxysilane group. ₃ represents an ethyltrimethoxysilane group, a propyltrimethoxysilane group, a butyltrimethoxysilane group, a pentyltrimethoxysilane group, a hexyltrimethoxysilane group, a heptyltrimethoxysilane group, an octyltrimethoxysilane group, a nonyltrimethoxysilane group, a decyltrimethoxysilane group, an undecyltrimethoxysilane group, a dodecyltrimethoxysilane group, an ethyltriethoxysilane group, a propyltriethoxysilane group, a butyltriethoxysilane group, a pentyltriethoxysilane group, a hexyltriethoxysilane group, a heptyltriethoxysilane group, an octyltriethoxysilane group, and a nonyltriethoxysilane group. The silane group may include at least one selected from the group consisting of an ethoxysilane group, a decyltriethoxysilane group, an undecyltriethoxysilane group, a dodecyltriethoxysilane group, an ethyldimethoxyethoxysilane group, a propyldimethoxyethoxysilane group, a butyldimethoxyethoxysilane group, a pentyldimethoxyethoxysilane group, a hexyldimethoxyethoxysilane group, a heptyldimethoxyethoxysilane group, an octyldimethoxyethoxysilane group, a nonyldimethoxyethoxysilane group, a decyldimethoxyethoxysilane group, an undecyldimethoxyethoxysilane group, and a dodecyldimethoxyethoxysilane group.

According to one embodiment, _R4 may have a H atom or a hydroxyl group at the end opposite to the portion linked to the methacryl group. For example, according to one embodiment, _R4 may include at least one selected from the group consisting of H, a 2-hydroxyethyl group, a 3-hydroxypropyl group, and a 2-hydroxybutyl group.

According to one embodiment, the surface treatment agent may be a copolymer of two different methacrylate-based monomers, a copolymer of an acrylate-based monomer and a methacrylate-based monomer, or a copolymer of an epoxy-based monomer and a methacrylate-based monomer.

According to one embodiment, the properties of a surface treatment agent for a composition containing a compound represented by any one of Chemical Formulas 1 to 3 can be determined depending on the ratio of m to n. According to one embodiment, m and n may have an integer ratio between 1:2 and 2:1. For example, m and n may have an integer ratio such as 1:1, 3:2, 2:3, 4:3, 5:3, 3:4, 5:4, or 7:4.

According to one embodiment, the surface treatment agent may be included in an amount of 10 to 30 parts by weight per 100 parts by weight of inorganic particles. According to one embodiment, if the surface treatment agent is included in an amount less than 10 parts by weight per 100 parts by weight of inorganic particles, dispersibility decreases, and if the amount is more than 30 parts by weight, curing does not occur smoothly during film production.

According to one embodiment, the surface treatment agent may further include at least one polymerization initiator selected from the group consisting of BPO (benzoyl peroxide), AIBN (azobisisobutylonitrile), and AIBA (2,2'-azobis(2-methylpropionamidine). According to one embodiment, the polymerization initiator may include a peroxide compound, an azo compound, or both.

According to one embodiment, the polymerization initiator may be present in an amount of 0.1% to 1% by weight of the surface treatment agent. According to one embodiment, if the polymerization initiator is present in an amount less than 0.1% by weight, copolymerization only partially occurs, and if the polymerization initiator content exceeds 1% by weight, excess polymerization initiator is distributed within the surface treatment agent and acts as an impurity.

According to one embodiment, the light transmittance of the surface treatment agent may be 40% or more.

According to one embodiment, the light transmittance of the surface treatment agent may be 40% or more, 42% or more, 45% or more, or 50% or more.

According to one embodiment, the haze of the surface treatment agent may be 80% or less.

According to one embodiment, the haze of the surface treatment agent may be 80% or less, 70% or less, 60% or less, or 50% or less.

According to one embodiment, the composition may further comprise a dispersant containing at least one functional group selected from the group consisting of a carboxyl group, a phosphate group, a phosphonate group, a sulfonic acid group, and a phenolic hydroxyl group. According to one embodiment, the dispersant may preferably contain a carboxyl group.

According to one embodiment, the dispersant may be commercially available. According to one embodiment, the dispersant may be a dispersant under the following trade names: DISPERBYK, DISPERBYK-101, DISPERBYK-102, DISPERBYK-103, DISPERBYK-106, DISPERBYK-107, DISPERBYK-108, DISPERBYK-109, DISPERBYK-110, DISPERBYK-111, DISPERBYK-112, DISPERBYK-115, DISPERBYK-116, DISPERBYK-118, DISPERBYK-130, DISPERBYK-140, DISPERBYK-141, DISPERBYK-142, DISPERBYK-143, DISPERBYK-144, DISPERBYK-145, DISPERBYK-146, DISPERBYK-147, DISPERBYK-148, DISPERBYK-149, DISPERBYK-150, DISPERBYK-151, DISPERBYK-152, DISPERBYK-153, DISPERBYK-154, DISPERBYK-155, DISPERBYK-156, DISPERBYK-157, DISPERBYK-158, DISPERBYK-159, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-167, DISPERBYK-168, DISPERBYK-169, DISPERBYK-170, DISPERBYK-171, DISPERBYK-172, ISPERBYK-140, DISPERBYK-142, DISPERBYK-145, DISPERBYK-160, DISP ERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBY K-165, DISPERBYK-166, DISPERBYK-167, DISPERBYK-168, DISPERBYK-16 9, DISPERBYK-170, DISPERBYK-171, DISPERBYK-174, DISPERBYK-176, DI SPERBYK-180, DISPERBYK-181, DISPERBYK-182, DISPERBYK-183, DISPE RBYK-184, DISPERBYK-185, DISPERBYK-187, DISPERBYK-190, DISPERBYK -191, DISPERBYK-192, DISPERBYK-193, DISPERBYK-194, DISPERBYK-200 0, DISPERBYK-2001, DISPERBYK-2008, DISPERBYK-2009, DISPERBYK-201 0, DISPERBYK-2020, DISPERBYK-2025, DISPERBYK-2050, DISPERBYK-2070, DISPERBYK-2090, DISPERBYK-2091, DISPERBYK-2095, DISPERBYK-2096, DISPERBYK-2150, DISPERBYK-2151, DISPERBYK-2152, DISPERBYK-2155, DISPERBYK-2163 and DISPERBYK-2164. In addition, according to one embodiment, the dispersant may include at least one selected from the group consisting of Antiterra-U, P104, Disperbyk110, Disperbyk130, Disperbyk160, Disperbyk170 Family, EFKA776, EFKA4050, EFKA4063, EFKA4051, Solsperse24000, Solsperse36600, Solsperse32600, Solsperse22000, and Solsperse5000, as long as the dispersant is of the above-mentioned trademark.

According to one embodiment, the dispersant may be included in an amount of 1 to 10 parts by weight per 100 parts by weight of the composition. According to one embodiment, the dispersant may be included in an amount of 1 to 5 parts by weight, or 3 to 7 parts by weight per 100 parts by weight of the composition.

According to one embodiment, the composition further comprises a dispersion solvent, which may include at least one selected from the group consisting of methyl ethyl ketone (MEK), ethanol, methanol, acetonitrile, toluene, tetrahydrofuran (THF), propylene glycol monomethyl ether acetate (PGMEA), and ethyl acetate.

According to one embodiment, the weight of the dispersion solvent may be equal to or greater than the weight of the surface-modified inorganic particles. According to one embodiment, the weight ratio of the surface-modified inorganic particles to the dispersion solvent may be 1:1 to 1:2.

According to one embodiment, the dispersion solvent may be 30% to 60% by weight of the composition. According to one embodiment, the dispersion solvent may be 30% by weight or more, 40% by weight or more, or 50% by weight or more, or 60% by weight or less, 50% by weight or less, 40% by weight or less, or a range between any two values selected from the above-mentioned numerical values.

According to one embodiment, the refractive index of the composition may be between 1.50 and 1.80.

According to one embodiment, the composition is a high refractive index dispersion composition, having a refractive index of 1.50 or more, 1.55 or more, 1.60 or more, 1.65 or more, 1.70 or more, or 1.75 or more, or 1.80 or less, 1.75 or less, 1.70 or less, 1.65 or less, 1.60 or less, 1.55 or less, or a range between any two values selected from the aforementioned numerical values.

According to one embodiment, the viscosity of the composition may be 180 cPs to 20,000 cPs (based on 25°C). According to one embodiment, the viscosity of the composition can be adjusted using a viscosity modifier such as MEK, toluene, or ethyl acetate. According to one embodiment, the viscosity of the composition may be preferably 180 cPs to 10,000 cPs (based on 25°C), and more preferably 180 cPs to 1,000 cPs (based on 25°C).

According to one embodiment, the haze of the composition may be 15% or less.

According to one embodiment, the haze of the composition may be 15% or less, preferably 14% or less, and more preferably 6% or less.

An adhesive film according to an embodiment of the present invention may be manufactured using a composition according to an embodiment of the present invention. The adhesive film according to an embodiment of the present invention may be manufactured using a composition according to an embodiment of the present invention, which includes inorganic particles surface-modified with a surface treatment agent and an acrylic monomer, and the inorganic particles and the acrylic monomer have a weight ratio of 1:1 to 2:1.

According to one embodiment, the adhesive film may be, for example, an adhesive film such as an OCA film or a PSA (pressure sensitive adhesive) film, which can provide an adhesive film that is flexible yet optically transparent.

The present invention will be explained in more detail below through examples and comparative examples.

However, the following examples are intended to illustrate the present invention, and the content of the present invention is not limited to the following examples.

1. Manufacturing of surface treatment agents

Example 1-1

3-methacryloxypropyltrimethoxysilane (MPTMS) and 2-hydroxyethyl methacrylate (2-HEMA) were mixed as monomers in a 1:1 weight ratio in methyl ethyl ketone (MEK) solvent. 0.01 g of AIBN was added as a polymerization initiator. The solvent was mixed in an amount equal to the total weight of the monomers. Growth was carried out at 60°C for 3 hours under a nitrogen atmosphere, and then the mixture was stirred at room temperature for 12 hours to polymerize the monomers and obtain a polymer.

Comparative Example 1-1

The polymer was obtained in the same manner as in Example 1-1 above, except that 2-hydroxyethyl acrylate (2-HEA) was used instead of 2-HEMA.

Comparative Example 1-2

The polymer was obtained in the same manner as in Example 1-1 above, except that 2-hydroxybutyl acrylate (2-HBA) was used instead of 2-HEMA.

2. Production of surface-treated inorganic particle dispersions

Example 2-1

40 g of zirconia powder with an average particle diameter of 10 nm, 60 g of methyl ethyl ketone (MEK) as a dispersion solvent, and 20 parts by weight of the polymer from Example 1-1 as a surface treatment agent per 100 parts by weight of the zirconia powder were added and dispersed for 3 hours to prepare an inorganic particle dispersion.

Example 2-2

An inorganic particle dispersion was prepared in the same manner as in Example 2-1 above, except that the amount of surface treatment agent added was 30 parts by weight per 100 parts by weight of zirconia powder.

Example 2-3

An inorganic particle dispersion was prepared in the same manner as in Example 2-1 above, except that the amount of surface treatment agent added was 40 parts by weight per 100 parts by weight of zirconia powder.

Comparative Example 2-1

An inorganic particle dispersion was prepared in the same manner as in Example 2-1 above, except that the polymer from Comparative Example 1-1 was not added as a surface treatment agent.

Comparative Example 2-2

An inorganic particle dispersion was prepared in the same manner as in Comparative Example 2-1, except that the amount of surface treatment agent added was 30 parts by weight per 100 parts by weight of zirconia powder.

Comparative Example 2-3

An inorganic particle dispersion was prepared in the same manner as in Comparative Example 2-1, except that the amount of surface treatment agent added was 40 parts by weight per 100 parts by weight of zirconia powder.

Comparative Example 2-4

An inorganic particle dispersion was prepared in the same manner as in Example 2-1 above, except that the polymer from Comparative Example 1-2 was not added as a surface treatment agent.

Comparative Example 2-5

In Comparative Examples 2-4, the inorganic particle dispersion was prepared in the same manner except that the amount of surface treatment agent added was 30 parts by weight per 100 parts by weight of zirconia powder.

Comparative Example 2-6

In Comparative Examples 2-4, the inorganic particle dispersion was prepared in the same manner except that the amount of surface treatment agent added was 40 parts by weight per 100 parts by weight of zirconia powder.

Comparative Example 2-7

40 g of zirconia powder with an average particle diameter of 10 nm, 60 g of methyl ethyl ketone (MEK) as a dispersion solvent, and 10 parts by weight of methacryloxypropyltrimethoxysilane as a surface treatment agent per 100 parts by weight of the zirconia powder were added and dispersed for 3 hours to prepare an inorganic particle dispersion.

Comparative Example 2-8

In Comparative Example 2-7, the inorganic particle dispersion was prepared in the same manner except that the amount of surface treatment agent added was 15 parts by weight per 100 parts by weight of zirconia powder.

Comparative Example 2-9

In Comparative Example 2-7, the inorganic particle dispersion was prepared in the same manner except that the amount of surface treatment agent added was 20 parts by weight per 100 parts by weight of zirconia powder.

Test Example 1: Optical Characteristics of Inorganic Particle Dispersions

To confirm the optical characteristics of the inorganic particle dispersions of Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-9 above, the total light transmittance and haze were measured and are shown in Table 1 below.

3. Organic-inorganic hybrid composition production example 3-1

Based on the total composition, 50 wt% of methyl ethyl ketone (MEK) as a dispersion solvent, 40 wt% of zirconia powder with an average particle diameter of 10 nm, and 10 wt% of the polymer from Example 1-1 as a surface treatment agent were mixed and stirred for 30 minutes. To ensure uniform dispersion of the zirconia particles, 200 wt% of zirconia beads (average particle diameter: 0.05 mm) were added per 100 wt% of the mixture, and the mixture was dispersed for 3 hours using a paint shaker. The dispersion was then recovered. Based on 50 wt% of the dispersion, 45 wt% of butylacrylate as an acrylic monomer and 5 wt% of a dispersant were added, and the pressure was reduced to remove the dispersion solvent, producing a composition.

Example 3-2

A composition was prepared in the same manner as in Example 3-1 above, except that 2-ethylhexyl acrylate was not added as an acrylic monomer.

Example 3-3

A composition was prepared in the same manner as in Example 3-1 above, except that isobornyl acrylate was not added as an acrylic monomer.

Example 3-4

A composition was prepared in the same manner as in Example 3-1 above, except that 4-acryloyl morpholine was not added as an acrylic monomer.

Comparative Example 3-1

A composition was prepared in the same manner as in Example 3-1 above, except that methacryloxypropyltrimethoxysilane was not added as a surface treatment agent.

Comparative Example 3-2

In Comparative Example 3-1, the composition was prepared in the same manner except that 2-ethylhexyl acrylate was not added as an acrylic monomer.

Comparative Example 3-3

In Comparative Example 3-1, the composition was prepared in the same manner except that isobornyl acrylate was not added as an acrylic monomer.

Comparative Example 3-4

In Comparative Example 3-1, the composition was prepared in the same manner except that 4-acryloyl morpholine was not added as an acrylic monomer.

Test Example 2: Physical Properties of Organic-Inorganic Hybrid Compositions

To confirm the physical properties of the compositions of Examples 3-1 to 3-4 and Comparative Examples 3-1 to 3-4, the refractive index, viscosity, and haze were measured and are shown in Table 2 below.

Although the embodiments have been described above, those skilled in the art may apply various technical modifications and variations based on the above. For example, the described techniques may be performed in a different order than described, and/or the components of the described systems, structures, devices, circuits, etc. may be combined or combined in a different manner than described, or may be substituted or replaced by other components or equivalents, and still achieve suitable results. Accordingly, other implementations, other embodiments, and equivalents to the claims are also within the scope of the following claims.

Claims (15)

Inorganic particles whose surfaces have been modified with a surface treatment agent;
an acrylic monomer;
Including,
The surface-modified inorganic particles and the acrylic monomer have a weight ratio of 1:1 to 2:1,
the surface treatment agent is a copolymer of a silane-based monomer and a methacrylate-based monomer,
the silane-based monomer is 3-methacryloxypropyltrimethoxysilane (MPTMS);
The organic-inorganic hybrid composition, wherein the methacrylate monomer is 2-hydroxyethyl methacrylate (2-HEMA) . The inorganic particles are
2. The organic- _inorganic hybrid composition of _claim 1 _, comprising at _{least one} selected from the _group consisting of _ZrO2 , SiO2, _Al2O3 , _CeO2 , _ZnO , _V2O5TiO2 , BaTiO3, SrTiO3, _BaTiO3 , _PbTiO3 , _PbZrO3 , Pb(Zr,Ti) _O3 (PZT) _{, Pb1} -xLaxZr1-yTiyO3 (PLZT), (1 _{- x} )Pb(Mg1/3Nb2/ ₃ ) _O3 - _{xPbTiO3 (} PMN-PT), _HfO2 , and _BN . The inorganic particles have a diameter of 10 nm to 200 nm,
2. The organic-inorganic hybrid composition according to claim 1, wherein the inorganic particles have a specific surface area of 1 m ² /g to 250 m ² /g. The organic-inorganic hybrid composition according to claim 1, wherein the surface-modified inorganic particles account for 40% to 50% by weight of the composition. The organic-inorganic hybrid composition according to claim 1, wherein the acrylic monomer includes at least one selected from the group consisting of butyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, and 4-acryloyl morpholine. The organic-inorganic hybrid composition according to claim 1, wherein the acrylic monomer accounts for 50% to 60% by weight of the composition. The organic-inorganic hybrid composition according to claim 1, wherein the surface treatment agent is contained in an amount of 10 to 30 parts by weight per 100 parts by weight of the inorganic particles. The organic-inorganic hybrid composition according to claim 1, further comprising a dispersant containing at least one functional group selected from the group consisting of a carboxyl group, a phosphate group, a phosphonate group, a sulfonic acid group, and a phenolic hydroxyl group. 9. The organic-inorganic hybrid composition according to claim 8 , wherein the dispersant is contained in an amount of 1 to 10 parts by weight based on 100 parts by weight of the composition. Further comprising a dispersion solvent,
2. The organic-inorganic hybrid composition according to claim 1, wherein the dispersion solvent comprises at least one selected from the group consisting of methyl ethyl ketone (MEK), ethanol, methanol, acetonitrile, toluene, tetrahydrofuran (THF), propylene glycol monomethyl ether acetate (PGMEA), and ethyl acetate. 11. The organic-inorganic hybrid composition according to claim 10 , wherein the weight ratio of the surface-modified inorganic particles to the dispersion solvent is 1:1 to 1:2. 11. The organic-inorganic hybrid composition according to claim 10 , wherein the dispersion solvent accounts for 30% to 60% by weight of the composition. The composition comprises:
The refractive index is 1.50 to 1.80,
The viscosity is 180 cPs to 20,000 cPs (at 25°C),
2. The organic-inorganic hybrid composition according to claim 1, having a haze of 15% or less. An adhesive film produced using the composition,
The composition comprises:
Inorganic particles whose surfaces have been modified with a surface treatment agent;
an acrylic monomer;
Including,
The surface-modified inorganic particles and the acrylic monomer have a weight ratio of 1:1 to 2:1,
the surface treatment agent is a copolymer of a silane-based monomer and a methacrylate-based monomer,
the silane-based monomer is 3-methacryloxypropyltrimethoxysilane (MPTMS);
The adhesive film, wherein the methacrylate monomer is 2-hydroxyethyl methacrylate (2-HEMA) . 15. The PSA film of claim 14, wherein the acrylic monomer comprises at least one selected from the group consisting of butyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, and 4-acryloyl morpholine.