KR20180093835A - Curable organic/inorganic hybrimer resin composition with high refractive index and the method of manufacturing the same - Google Patents

Abstract

The present invention relates to a curable organic/inorganic hybrimer resin composition with a high refractive index which has a high refractive index and simultaneously realizes excellent transparent, heat resistant, and molding properties, and an optical film using the same. The curable organic/inorganic hybrimer resin composition with a high refractive index comprises: (A) a monomer mixture including a pyran-based reactive monomer and a siloxane-based reactive monomer; and (B) a reactive inorganic nanosol having a functional group reactive with monomers within the monomer mixture.

Description

TECHNICAL FIELD [0001] The present invention relates to a high refractive index curable organic / inorganic hybrid resin composition and a method of manufacturing the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to a high refractive index curable organic / inorganic hybrid resin composition having a high refractive index and simultaneously exhibiting excellent transparency, heat resistance and moldability, and an optical film using the same.

Currently, devices used for display or illumination have low external light efficiency, and there is a growing demand for devices and materials that can be driven by environmentally friendly and low power consumption in the future lighting industry due to high power consumption.

Although organic light emitting devices (OLEDs) are applied to displays and lights for high efficiency due to the development of light emitting materials, there is a problem in that efficiency of light extraction due to the inter-layer refractive index difference is low. In order to emit light lost due to the difference in refractive index to the outside, development of a high refractive index material for internal light extraction similar to or higher than ITO refractive index, or a technique using a microlens or a nanostructure for external light extraction is required have.

In particular, polyimide-based and acrylic-based polymer materials including sulfur atoms have been developed as internal light extraction flat layer materials, but materials satisfying physical properties such as high refractive index, thermal stability, storage stability, and optical patterning function are extremely rare, There is a limit to the development of a material that can achieve a high refractive index only with a polymer material.

The present invention has been conceived to solve the above problems, and it is an object of the present invention to provide a light emitting device and a light emitting device, which can easily process a thin film and form a pattern using a thermosetting or photocuring reaction, It is an object of the present invention to provide a high refractive index curable organic / inorganic hybrid resin composition.

The present invention also relates to a high refractive index organic / inorganic hybrid resin composition which is capable of remarkably improving the refractive index including an inorganic nano-sol, exhibiting excellent thermal stability and high transparency, And an optical film produced using the resin composition.

One aspect of the present invention relates to a method for producing a polymer composition comprising (A) a monomer mixture comprising a pyran-based reactive monomer and a siloxane-based reactive monomer and (B) a reactive inorganic nano-sol having a functional group capable of reacting with monomers in the monomer mixture Based hybrid resin composition.

In the organic hygroscopic resin composition according to one embodiment of the present invention, the pyran-based reactive monomer may be a compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1), R ₁ may be any one or more functional groups selected from a (meth) acrylate group, a vinyl group and an epoxy group, or an alkyl group having one or more functional groups.

In the organic hygroscopic resin composition according to one embodiment of the present invention, the siloxane-based reactive monomer may be a compound represented by the following formula (2).

(2)

Wherein R ₂ to R ₅ are independently of each other a C ₁ -C ₂₀ alkyl group, R ₇ and R ₈ are independently of each other C ₁ -C ₁₀ alkylene, and R ₆ and R ₉ are independently of each other Is a group containing any one reactive functional group selected from a maleimide group, a maleic anhydride group, a carboxy group, an isocyanate group, an amine group, an epoxy group, or an alkyl group substituted therewith. The above-mentioned m is an integer of 1 to 1,000, preferably 1 to 100.

In the organic hygroscopic resin composition according to one embodiment of the present invention, the monomer mixture may further include a polyfunctional (meth) acrylate-based monomer.

In the organic hybrid resin composition according to one embodiment of the present invention, the multifunctional (meth) acrylate monomer may be selected from the group consisting of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate ), Pentaerythritol tetraacrylate, and pentaerythritol triacrylate. [0031] The term &

In the organic hygroscopic resin composition according to one embodiment of the present invention, the inorganic nano sol may be included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the monomer mixture.

The reactive inorganic nano-sol may be a functional group selected from an acrylate group, an epoxy group, a hydroxyl group and an amine group, and may be a surface-modified zirconia, titania, silica, alumina, Zirconium titanate, strontium titanate, and a compound of any of these compounds. The present invention is not limited to these examples.

Another embodiment of the present invention relates to an organic hybrid resin prepared from the resin composition described above.

Further, another aspect of the present invention relates to an optical film produced from the above-mentioned organic-inorganic hybrid resin composition.

INDUSTRIAL APPLICABILITY The organic hygroscopic resin composition according to the present invention is excellent in moldability of a thin film by using a thermosetting or photo-curing reaction with an improved degree of curing, is easy to form a fine pattern, has a high refractive index, There is an excellent advantage.

The organic hygroscopic resin composition according to the present invention has an excellent heat resistance and transparency and is easy to control the refractive index.

The organic-inorganic hybrid resin composition according to the present invention will be described in detail. However, this is not intended to limit the scope of protection defined by the claims. In addition, technical terms and scientific terms used in the description of the present invention have the meanings as commonly understood by those of ordinary skill in the art to which the present invention belongs, unless otherwise defined.

Throughout the description describing the present invention, "including" an element means that it can include other elements, not excluding other elements unless specifically stated otherwise.

In the present invention, the term " (meth) acrylate " is used to collectively mean acrylate and methacrylate.

The inventors of the present invention have intensified their research on optical films that have high refractive indexes and are applicable to devices for display and optical applications. As a result, they have found that the combination of a specific pyran-based reactive monomer and a siloxane-based reactive monomer and a combination of inorganic nano- Based hybrid resin composition. The organic or inorganic hybrid resin prepared from the resin composition effectively prevents the phase separation between the organic and inorganic materials while facilitating thin film processing and pattern formation, and exhibits a high degree of curing by thermal curing or light curing. In addition, it has excellent moldability and is easy to form thin film and pattern. Further, it has been found that the refractive index can be remarkably improved, and excellent thermal stability, transparency, and high light transmittance can be realized.

Specifically, one embodiment of the present invention relates to a process for preparing a monomer mixture comprising (A) a monomer mixture comprising a pyran-based reactive monomer and a siloxane-based reactive monomer and (B) a reactive inorganic nano sol having a functional group capable of reacting with monomers in the monomer mixture And to provide a composition for producing an organic / inorganic hybrid resin having a high refractive index. Hereinafter, the composition for preparing an organic hybrid resin is referred to as an organic hybrid resin composition.

According to one embodiment of the present invention, the above-mentioned pyran-based reactive monomer is not limited to a great extent to achieve the object of the present invention, but it may preferably be represented by the following general formula (1).

[Chemical Formula 1]

In the above formula (1), R ₁ may be any one or more functional groups selected from a (meth) acrylate group, a vinyl group and an epoxy group, or an alkyl group having one or more functional groups. The alkyl group may have 1 to 6 carbon atoms.

The above-mentioned pyran-based reactive monomer may preferably be one having a (meth) acrylate group. This improves the degree of curing and can further increase the refractive index of the organic / inorganic hybrid resin, and at the same time, it is more effective in effectively preventing the phase separation between the organic materials.

According to one embodiment of the present invention, the pyran compound having a (meth) acrylate group may be a compound represented by the following formula (3). The (meth) acrylate group is preferably capable of photoreaction under a photocatalyst, and is advantageous in forming a light extraction flat layer of a high refractive index and forming a pattern.

(3)

The compound of formula (3) is not limited in its production method, but may be one prepared by the following reaction scheme 1 as a preferred embodiment.

[Reaction Scheme 1]

The compound of Formula 3 may be prepared by slowly adding triamine to 3,4-dihydro-2H-pyran-2-methanol as a pyran compound, The reaction product may be prepared by stirring the mixture at room temperature (25 ° C) to prepare a reaction product, and then dropping a solution in which methacryloyl chloride is diluted with an organic solvent to the reaction product slowly dropwise.

According to one embodiment of the present invention, the siloxane-based reactive monomer can be used in combination with the above-mentioned pyran-based reactive monomer to improve the degree of curing of the organic resin, improve thermal stability and further improve compatibility with inorganic nano sol .

Specifically, the siloxane-based reactive monomer may be a compound represented by the following formula (2).

(2)

Wherein R ₂ to R ₅ are independently of each other a C ₁ -C ₂₀ alkyl group, R ₇ and R ₈ are independently of each other C ₁ -C ₁₀ alkylene, and R ₆ and R ₉ are independently of each other Is a group containing any one reactive functional group selected from a maleimide group, a maleic anhydride group, a carboxy group, an isocyanate group, an amine group, an epoxy group, or an alkyl group substituted therewith. The functional group may be capable of reacting with the functional group of the monomer of formula (I) or may be capable of reacting with functional groups formed on the surface of the reactive inorganic nano-sol. Also, m is an integer of 1 to 1,000, preferably 1 to 500, and more preferably 2 to 100.

According to one embodiment of the present invention, the siloxane-based reactive monomer may have a weight average molecular weight of 50 to 50,000 g / mol, specifically 500 to 40,000 g / mol, more specifically 800 to 30,000 g / mol. In view of realizing the synergistic effects of high refractive index, transparency and heat resistance, the present invention is not limited thereto.

More preferably, the siloxane-based reactive monomer may include a maleimide group. This is effective in terms of realizing a high degree of curing and a refractive index and realizing excellent heat resistance and moldability. Furthermore, it is more effective in effectively preventing the phase separation between the organic material and the inorganic material.

The siloxane-based reactive monomer having a maleimide group may be represented by the following general formula (4). Here, m is an integer of 1 to 1,000, preferably 1 to 100.

[Chemical Formula 4]

The compound of formula (4) is not limited in its production method, but may be prepared by the following reaction scheme 2 as a preferred embodiment.

[Reaction Scheme 2]

For example, when m = 1 in the compound of formula (4), 1,3-bis (3-aminopropyl) tetramethyldisiloxane is diluted with an organic solvent And slowly dropwise adding the solution to maleic anhydride.

According to one aspect of the present invention, the monomer mixture may have a combination comprising a polyfunctional (meth) acrylate-based monomer together with a pyran-based reactive monomer and a siloxane-based reactive monomer. This can further improve the curing degree of the organic or inorganic hybrid resin to be produced, and is more advantageous in terms of prevention of phase separation and formation of a light extraction flat layer of high refractive index and pattern formation.

The polyfunctional (meth) acrylate monomer is not particularly limited, but it is preferably at least two or more (meth) acrylate groups, more preferably at least three or more (Meth) acrylate group.

For example, the polyfunctional (meth) acrylate monomer may be selected from the group consisting of dipentaerythritol hexacrylate, dipentaerythritol pentaacrylate, pentaerythritol tetraacrylate, And pentaerythritol triacrylate. However, the present invention is not limited thereto. The term " pentaerythritol triacrylate " And more preferably dipentaerythritol hexaacrylate represented by the following formula (5).

[Chemical Formula 5]

The above-mentioned polyfunctional (meth) acrylate monomer can further improve the curing degree of the resin prepared by combination with the above-mentioned pyran-based reactive monomer and siloxane reactive monomer, and is capable of improving moldability, It is more effective in terms of being able to increase.

Further, the monomer mixture may be a compound containing a hydroxy group as the (meth) acrylate monomer. For example, it may be a compound represented by the following formula (6). This is more effective in terms of facilitating thermal polymerization and improving physical properties such as refractive index.

[Chemical Formula 6]

According to an embodiment of the present invention, the content of the monomer mixture in the organic-resin hybrid resin composition may be 20 to 80% by weight, specifically 25 to 75% by weight, more specifically 30 to 70% by weight. But the present invention is not limited to this in view of being able to have a high refractive index in the above range and simultaneously facilitate thin film processing and pattern formation.

According to one aspect of the present invention, the reactive inorganic nano-sol is a functional group having a functional group capable of reacting with monomers in the monomer mixture, and is a functional group selected from an acrylate group, an epoxy group, a hydroxyl group and an amine group. , And may be at least one selected from the group consisting of silica, alumina, magnesia, tin oxide, zinc oxide, barium titanate, zirconium titanate, strontium titanate, and compounds thereof, but is not limited thereto . In addition, the reactive inorganic nano-sol may include a non-surface-modified functional group, but it is preferable that the reactive inorganic nano-sol can be reacted with the monomers in the monomer mixture. Commercial examples of the reactive inorganic nano sols include, but are not limited to, PixClear-PM (Pixelligent Technologies).

The size of the reactive inorganic nano-sol may not be limited, but is preferably 1 to 500 nm, preferably 5 to 200 nm, and the size of the secondary particle obtained by dispersing the metal particle in a solvent is preferably May have a particle distribution of 10 to 1,000 nm, but the present invention is not limited thereto. This is preferable because it can secure a high transmittance at the same time as the refractive index increases.

The reactive inorganic nano-sol may be one in which inorganic particles are dispersed in a solvent, and the content of the inorganic particles, that is, the solid content may be 30 to 70% by weight, specifically 40 to 60% by weight. A high curing degree and transparency, a high refractive index and a heat resistance according to the combination with the monomers in the above range, but it is not necessarily limited to the above numerical range.

The content of the reactive inorganic nano-sol in the organic-inorganic hybrid resin composition may be controlled within the range of the solid content of the reactive inorganic nano-sol. At this time, the content of the reactive inorganic nano-sol is not particularly limited, but may be specifically 20 to 80% by weight, more specifically 25 to 75% by weight. In this range, the degree of curing can be increased, and it is effective in improving transparency, heat resistance and refractive index characteristics, but is not limited to the above numerical range.

According to one aspect of the present invention, the organic-inorganic hybrid resin composition may include an initiator, preferably a photoinitiator. The photoinitiator can be used without being limited to a great extent within the scope of achieving the object of the present invention. Specifically, at least one selected from a benzophenone-based compound, an acetophenone-based compound, a nonimidazole-based compound, a triazine-based compound, an oxime-based compound, and mixtures thereof can be used. More specifically, it is possible to use benzophenone, benzoyl methyl benzoate, acetophenone, 2,4-diethyl thioxanthone, 2-chlorothioxanthone, Hydroxy-2-methyl-1-phenyl-propane (1-Hydroxy-cyclohexyl-phenyl-ketone), 2-chloro thioxanthone, ethyl anthraquinone, (2-Hydroxy-2-methyl-1-phenyl-propan-1-one) may be used as the solvent. However, it is not limited thereto. Commercial products include Irgacure from BASF But is not limited to.

The photoinitiator is more effective in forming a radical by ultraviolet rays and capable of crosslinking unsaturated hydrocarbons present in the organic / inorganic hybrid resin composition.

One aspect of the present invention is to provide an organic hygroscopic resin having a high refractive index represented by the following structural formula.

The organic hygroscopic resin according to one embodiment of the present invention has high refractive index, excellent thermal stability and light transmittance, and further does not cause phase separation between the copolymer and inorganic nanosol.

According to an embodiment of the present invention, the organic-inorganic hybrid resin composition may further include at least one additive selected from a releasing agent, a slipping agent, a plasticizer, a surfactant, a dispersing agent, and a leveling agent. At this time, BYK-333, BYK-347, and BYK-348 of BYK Chemie may be used alone or as a mixture of two or more of the leveling agents, but the present invention is not limited thereto.

According to one embodiment of the present invention, the organic-inorganic hybrid resin composition may be manufactured as an environment-friendly solvent-free type using no organic solvent, or may be a solvent-type using an organic solvent.

According to an aspect of the present invention, there is provided an organic-inorganic hybrid resin composition comprising an organic solvent, wherein the organic solvent can be used in consideration of physical properties, coating properties, curing properties, or physical properties of the final product. In one specific example, ketone solvents such as methyl isobutyl ketone, methyl ethyl ketone, and dimethyl ketone; Alcohol solvents such as isopropyl alcohol, isobutyl alcohol and normal butyl alcohol; Acetate solvents such as ethyl acetate or normal butylacetate; And cellosolve solvents such as ethyl cellusolve or butyl cellusolve can be used. Further, it is also possible to use N, N-dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), N, N-dimethylformamide (DMF), tetrahydrofuran N-dimethylacetamide (DEAc), N, N-dimethylmethoxyacetamide, dimethylsulfoxide, m-dioxane, p-dioxane, 1,2-dimethoxyethane, bis (2-methoxyethoxy) ether, propylene glycol monomethyl ether acetate (PGMEA), poly (2-methoxyethoxy) Ethylene glycol) methacrylate (PEGMA), and the like, but not always limited thereto.

Another aspect of the present invention is to provide an organic-inorganic hybrid resin prepared from the above organic-inorganic hybrid resin composition.

According to one embodiment of the present invention, the organic hygroscopic resin may have a weight average molecular weight of 500 to 200,000 g / mol, specifically 1,000 to 100,000 g / mol, more specifically 1,000 to 20,000 g / mol. When the above range is satisfied, it is more effective not only in terms of high refractive index and heat resistance, but also in compatibility and micro patterning in coating with a reaction solvent. In this case, the weight average molecular weight may be measured by a conventional method. For example, PL gel Olexis was used as a column, which was measured using 1260 Infinity (standard sample: polystyrene) manufactured by Agilent Technologies , And a sample containing 4 mg of DMAc as a solvent in 100 ml of LiCl (concentration: 0.5 wt%) was used.

Still another aspect of the present invention is to provide a film formed by applying the above organic hygroscopic resin composition.

At this time, the film may have a refractive index of 1.7 to 2.0, specifically 1.75 to 1.95, measured at a wavelength of 550 nm using a spectroscopic Ellipsometer (M2000D by Woollam).

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples and experimental examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited by the following examples.

(Production Example 1)

Preparation of Compound (3)

3,4-Dihydro-2H-pyran-2-methanol (30 g, 262.83 mmol) was added to a 500 mL three-necked flask, and triethylamine (33.2 g, 328.54 mmol) was slowly added thereto and the inside of the flask was lowered to 0 ° C. Methacryloyl chloride (30.2 g, 289.11 mmol) was diluted with 100 ml of tetrahydrofuran and added dropwise thereto. After completion of the reaction, the product was separated using column chromatography (EA: Hexane = 1: 6) to obtain 14 g (50% yield) of a pyran compound represented by the following formula (3), and its structure was confirmed by NMR and IR.

(3)

(Production Example 2)

Preparation of Compound (4)

Maleic anhydride (3.47 g, 35.41 mmol) and toluene (400 g) were added to a 3 L round-bottomed flask, and then 1,3-Bis (3-aminopropyl) tetramethyldisiloxane (4 g, 16.095 mmol) was diluted with toluene and slowly added dropwise. Then, the mixture was stirred at room temperature for 2 hours, and Zinc bromide (7.97 g, 35.41 mmol) and hexamethyldisilazane (13.14 g, 81.44 mmol) were added and stirred under reflux. As the reaction progressed, the color changed from white to brown, and the reaction was terminated by using 0.5N HCl after 12 hours. After extraction using EA / H ₂ O, the solvent was rotary evaporated to obtain 5 g (80% yield) of a silicone compound of the following formula (IV), which was an ivory solid, and its structure was confirmed by NMR and IR.

[Chemical Formula 4]

(Example 1)

Preparation of organic / inorganic hybrid resin composition

15% by weight of the pyran-based compound of Formula 3 prepared in Preparation Example 1, 25% by weight of the siloxane-based compound of Formula 4 prepared in Preparation Example 2 and 25% by weight of dipentaerythritol hexaacrylate (Cas. 29570-58-9) A photoinitiator (Irgacure 占 550 (BASF)) was added to a monomer mixture of 10% by weight and 50% by weight of zirconia inorganic nano sol (PixClear-PM, Pixellent Technologies, solid content 50% Respectively. The photoinitiator contained 1 part by weight per 100 parts by weight of the total of the monomer mixture and the inorganic nano sol. The reaction product was stirred at 25 DEG C to obtain a composition for preparing an organic hybrid resin.

The composition for the preparation of the organic-inorganic hybrid resin was dropped on a 2-inch silicon wafer, and then the material was coated at 1,500 rpm for 10 seconds using a spin coater to obtain a thin film. The thin film was heat-treated in a hot plate at 80 占 폚 for 10 minutes, and then photocured using a UV exposure apparatus (Flocimitty Exposure TME-150PRC manufactured by Topcon Co., Ltd., exposure dose: 13 mW / A high-refraction film was obtained. Thereafter, the physical properties were measured according to the following physical property evaluation, and the results are shown in Table 1.

(Example 2)

In Example 1, the content of the pyran-based compound represented by Formula (3) and the siloxane-based compound represented by Formula (4) were changed to 20 wt% and 30 wt%, respectively, without using dipentaerythritol hexaacrylate as the monomer mixture A high-refraction film having a thickness of 600 nm was obtained in the same manner as in Example 1. [

(Example 3)

The procedure of Example 1 was repeated except for changing the content of the pyran compound of Formula 3 to 10% by weight as a monomer mixture and further containing 10% by weight of the compound of Formula 6 below, A high-refraction film was obtained.

[Chemical Formula 6]

(Comparative Example 1)

In the same manner as in Example 2 except that the content of the siloxane-based compound represented by the general formula (4) was changed to 50 wt% without using the pyran-based compound represented by the general formula (3) as the monomer mixture in Example 2, A high-refraction film was obtained.

(Comparative Example 2)

The procedure of Example 2 was repeated except that the siloxane compound of Formula 4 was not used as the monomer mixture and the content of the pyran compound of Formula 3 was changed to 50 wt% A high-refraction film was obtained.

(Comparative Example 3)

The procedure of Example 1 was repeated except that the pyran compound of Formula 3 was not used as the monomer mixture and the content of the siloxane compound of Formula 4 was changed to 40 wt% A high-refraction film was obtained.

(Comparative Example 4)

A high-refraction film having a thickness of 600 nm was obtained in the same manner as in Example 1, except that the siloxane-based compound of the formula (4) was not used as the monomer mixture and the content of the formula (3) was changed to 40% by weight.

division Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Refractive index 1.7963 1.7824 1.7995 1.6281 1.5943 1.5273 1.5366 Transmittance 93 93 95 72 74 79 76 Thermal stability ○ ○ ○ × × × × Fine Pattern Formability ○ ○ ○ × × × ×

(Property evaluation)

(1) Refractive index: The refractive index at a wavelength of 550 nm was measured using a spectroscopic Ellipsometer (M2000D by Woollam).

(2) Transmittance: The light transmittance at a wavelength of 400 nm was measured using a spectrophotometer UV-3100PC (Shimadzu Corporation).

(3) Thermal Stability: The decomposition temperatures of the films prepared in Examples and Comparative Examples were measured using TGA1 (STAR SYSTEM, METTLER TOLEDO) equipment. TGA was measured at 0 ° C to 500 ° C in a nitrogen atmosphere at a heating rate of 10 ° C / min, and 1% and 5% weight loss were determined. When the criterion was met based on the decomposition temperature, Respectively.

(4) Fine pattern formation property: The fine pattern was exposed to a photomask and a silicon wafer on which a circuit pattern was drawn using a mask aligner, and the pattern formed was visually inspected using an optical microscope and SEM equipment Respectively. If the pattern is well formed, the pattern is marked as × if the pattern is not crushed or damaged.

As can be seen from Table 1, the high refractive index films of Examples 1 to 3 prepared according to an embodiment of the present invention have a high refractive index of 1.7824@550 nm to 1.7995@550 nm, and transmittances of up to 95% In addition, it was confirmed that it is possible to apply the present invention to a flat layer for light extraction, because of its excellent thermal stability and fine pattern formation property, and thus can be applied to lighting or display fields. On the other hand, in the case of Comparative Examples 1 to 4, the refractive index and the transmittance were lower than those of the Examples, and the thermal stable and fine Pattern-forming properties could not be ensured.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, Those skilled in the art will recognize that many modifications and variations are possible in light of the above teachings.

Accordingly, the spirit of the present invention should not be construed as being limited to the embodiments described, and all of the equivalents or equivalents of the claims, as well as the following claims, belong to the scope of the present invention .

Claims (9)

(A) a monomer mixture comprising a pyran-based reactive monomer and a siloxane-based reactive monomer and
(B) a reactive inorganic nano sol having a functional group capable of reacting with monomers in the monomer mixture
And a high refractive index. The method according to claim 1,
Wherein the pyran-based reactive monomer is a compound represented by the following formula (1).
[Chemical Formula 1]

(In the above formula (1), R ₁ may be any one or more functional groups selected from among a (meth) acrylate group, a vinyl group and an epoxy group, or an alkyl group having one or more functional groups.) The method according to claim 1,
Wherein the siloxane-based reactive monomer is a compound represented by the following formula (2).
(2)

(Wherein R ₂ to R ₅ are independently of each other a C ₁ -C ₂₀ alkyl group, R ₇ and R ₈ are each independently C ₁ -C ₁₀ alkylene, and R ₆ and R ₉ are a And m is an integer of from 1 to 1,000, and is independently a group containing a reactive functional group selected from a maleimide group, a maleic anhydride group, a carboxy group, an isocyanate group, an amine group, an epoxy group, .) The method according to claim 1,
Wherein the monomer mixture further comprises a polyfunctional (meth) acrylate-based monomer. 5. The method of claim 4,
Wherein the polyfunctional (meth) acrylate monomer is at least one selected from the group consisting of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, pentaerythritol tetraacrylate, and pentaerythritol triacrylate. Wherein the high refractive index resin has a high refractive index. The method according to claim 1,
Wherein the inorganic nano-sol has a high refractive index of 1 to 50 parts by weight based on 100 parts by weight of the monomer mixture. The method according to claim 1,
The reactive inorganic nano-sol may be a functional group selected from the group consisting of an acrylate group, an epoxy group, a hydroxyl group and an amine group. The functional inorganic nano-sol includes zirconia, titania, silica, alumina, magnesia, tin oxide, zinc oxide, barium titanate, zirconium titanate , Strontium titanate, and a compound of any of these compounds. An organic or inorganic hybrid resin prepared from the composition of any one of claims 1 to 7. An optical film produced from the organic / inorganic hybrid resin of claim 8.