KR20130048298A - Hard coating composition, hard coating film, polarizing plate and image display device using the same - Google Patents

Abstract

PURPOSE: A hard coating composition is provided to obtain superior hardness, scratch resistance, and superior adhesion to a substrate film by including a polysilsesquioxane compound with a specific structure. CONSTITUTION: A hard coating composition comprises a polysilsesquioxane compound represented by chemical formula 1 or 2. In chemical formula 1 or 2, R can contain 2-20 (meth)acrylate groups-containing C2-80 aliphatic group or aromatic hydrocarbon which can contain hetero atom or not. A hard coating film contains the hard coating composition spread on one or both sides of a transparent substrate.

Description

Hard coating composition, hard coating film, polarizing plate and display device using the same {Hard Coating Composition, Hard Coating Film, Polarizing Plate and Image Display Device Using the Same}

The present invention relates to a hard coating composition, a hard coating film, a polarizing plate and a display device using the same.

Hard coating films are widely used in various display panels, such as liquid crystal displays (LCDs), plasma displays (PDPs), CRTs, electroluminescent displays (ELs), and the like for surface protection. The hard coating film may also provide hard coating properties and properties of resistance to display by fingerprints, markers, and the like, and / or ease of removal (ie, antifouling).

These hard coat films include UV curable acrylic hard coat materials such as polyesters, acrylates, urethane acrylates and epoxy acrylates, as well as colloidal silica particles to impart sufficient surface protection properties to have as hard coat films. An organic-inorganic coating solution has been used as a hard coating composition to prepare a hard coating film having high hardness and improved wear resistance.

However, even when various organic-inorganic coating liquids containing silica particles were used as the composition for hard coating, stability problems due to precipitation and gel generation of colloidal silica particles whose silica surface was modified with organic materials or silanes were raised. Curability, optical clarity and adhesion still fail to meet the requirements for hard coat films for display device protection.

In order to improve the hardness of the hard coating film, the thickness of the hard coating film may be increased, but in this case, the hardness of the obtained hard coating film may be improved. There is a problem in that curling curls become large and handleability is lowered.

It is an object of the present invention to provide a hard coating composition that can be usefully used in the manufacture of a hard coating film that is excellent in hardness, scratch resistance and adhesion with a base film, and hardly causes curling.

Another object of the present invention is to provide a hard coating film formed using the hard coating composition and hardly occurs in hardness, scratch resistance and curling phenomenon.

Still another object of the present invention is to provide a polarizing plate having excellent hardness and scratch resistance provided with the hard coat film.

Still another object of the present invention is to provide an image display device having excellent hardness and scratch resistance provided with the hard coat film.

In order to achieve the above object, the present invention provides a hard coating composition comprising a polysilsesquioxane compound (C) represented by the following formula (1) or (2).

[Formula 1]

[Formula 2]

(In Formula 1 or Formula 2, R is an aliphatic or aromatic hydrocarbon having 2 to 80 carbon atoms containing 2 to 20 (meth) acrylate groups, and may or may not include a hetero atom.)

In addition, the hard coating composition may include a polyfunctional (meth) acrylate oligomer (A), a (meth) acrylate monomer (B), a photoinitiator (D) and a solvent (E).

The polysilsesquioxane compound (C) may be included in an amount of 0.1 to 50 parts by weight based on 100 parts by weight of the total hard coating composition.

The hard coating composition is 1 to 80 parts by weight of the (meth) acrylate oligomer (A), 1 to 70 parts by weight of the (meth) acrylate monomer (B) with respect to 100 parts by weight of the total, the polysilsesquioxane 0.1 to 50 parts by weight of the compound (C), 0.1 to 10 parts by weight of the photoinitiator (D) and 0.1 to 90 parts by weight of the solvent (E) may be included.

In order to achieve the other object of the present invention, the present invention provides a hard coating film having a hard coating layer formed by applying a hard coating composition on one side or both sides of a transparent substrate and then curing.

In order to achieve another object of the present invention, the present invention provides a polarizing plate having a hard coating film.

In order to achieve another object of the present invention, the present invention provides a display device having a hard coating film.

The hard coating composition according to the present invention includes an organic-inorganic hybrid type polysilsesquioxane compound represented by Chemical Formula 1 or 2, and exhibits excellent adhesiveness with the base film when coated on the base film. In addition, the hard coating composition according to the present invention is excellent in productivity due to the fast curing speed in the production of the coating film, the hard coating film prepared after curing has excellent hardness and scratch resistance as well as hardly curling phenomenon occurs. . Accordingly, the hard coat film of the invention has an effect of showing excellent physical properties when applied to the polarizing plate and the display device.

Hereinafter, the present invention will be described in more detail.

The hard coating composition according to the present invention comprises a polysilsesquioxane compound (C). The hard coating composition may include a polyfunctional (meth) acrylate oligomer (A), a (meth) acrylate monomer (B), a photoinitiator (D) and a solvent (E). Hereinafter, each component will be described in detail.

Multifunctional  ( Meta ) Acrylate Oligomer (A)

The polyfunctional (meth) acrylate oligomer (A) may be used without limitation in the art. (Meth) acrylate oligomer (A) represented by the following general formula (3) for better hardness improvement.

(3)

(In Formula 3, X is an aliphatic or aromatic hydrocarbon containing or not containing 2 to 80 heteroatoms including 2 to 20 (meth) acrylate functional groups, R is linear, branched Or a cyclic C3-C50 aliphatic or aromatic hydrocarbon, with or without a hetero atom, m is an integer from 1 to 10.)

The polyfunctional (meth) acrylate oligomer (A) represented by Formula 3 may be prepared by reacting a (meth) acrylate monomer containing a hydroxy group with a compound having two or more isocyanate groups in a molecule.

Compounds having two or more isocyanate groups in the molecule include 4,4'-dicyclohexyl diisocyanate, hexamethylene diisocyanate trimer, 1,4-diisocyanatobutane, 1,6-diisocyanatohexane, 1,8 -Diisocyanatooctane, 1,12-diisocyanatodecane, 1,5-diisocyanato-2-methylpentane, trimethyl-1,6-diisocyanatohexane, 1,3-bis (isocyanatomethyl) Cyclohexane, trans-1,4-cyclohexene diisocyanate, 4,4'-methylenebis (cyclohexyl isocyanate), isophorone diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, Xylene-1,4-diisocyanate, tetramethylxylene-1,3-diisocyanate, 1-chloromethyl-2,4-diisocyanate, 4,4'-methylenebis (2,6-dimethylphenylisocyanate) From 4,4'-oxybis (phenylisocyanate), hexamethylene diisocyanate A trifunctional isocyanate, at least one selected from the tree methane propanol air duct toluene diisocyanate, one isocyanate, the group consisting of meth-acryloyl isocyanate of an acrylic which can be used.

Also, the (meth) acrylate monomer containing a hydroxy group may be at least one selected from the group consisting of 2-hydroxyethyl (meth) acrylate, 2-hydroxyisopropyl (meth) acrylate, 4-hydroxybutyl (Meth) acrylate selected from the group consisting of hydroxy (meth) acrylate, pentaerythritol tri / tetra (meth) acrylate mixture, dipentaerythritol penta / hexa have.

The polyfunctional (meth) acrylate oligomer (A) is preferably included 1 to 80 parts by weight based on 100 parts by weight of the total hard coating composition. When the content of the multifunctional (meth) acrylate oligomer (A) is less than 1 part by weight based on the above-mentioned standards, it is difficult to produce sufficient hardness, and when it exceeds 80 parts by weight, there is a problem in that workability is poor due to poor compatibility with the coating solution.

( Meta ) Acrylate Monomer (B)

The (meth) acrylate monomer (B) is included to improve the hardness and the curling properties of the cured layer.

The (meth) acrylate monomer (B) can be used without limitation, those generally used in the art. Preferably, the (meth) acrylate monomer (B) is dipentaerythritol penta / hexa (meth) acrylate, pentaerythritol tri / tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, (meth) Acrylic ester, trimethylolpropane tri (meth) acrylate, glycerol tri (meth) acrylate, tris (2-hydroxyethyl) isocyanurate, tri (meth) acrylate, ethylene glycol di (meth) acrylate , Propylene glycol (meth) acrylate, 1,3-butanedioldi (meth) acrylate, 1,4-butanedioldi (meth) acrylate, 1,6-hexanedioldi (meth) acrylate, neopentyl glycoldi (Meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, bis (2-hydroxyethyl) isocyanurate di ( Ta) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, isooctyl (meth) acrylate, iso-decyl (meth) acrylate, ste It may include at least one selected from the group consisting of aryl (meth) acrylate, tetrahydroperfuryl (meth) acrylate, phenoxyethyl (meth) acrylate, isobornol (meth) acrylate and the like.

The amount of the (meth) acrylate monomer (B) is not limited, but preferably 1 to 70 parts by weight based on 100 parts by weight of the total hard coating composition. If the content of the (meth) acrylate monomer (B) is less than 1 part by weight or more than 70 parts by weight based on the above criteria, it is difficult to exhibit the effect of sufficient hardness improvement.

Polysilsesquioxane  The compound (C)

The polysilsesquioxane compound (C) is included to impart hardness improvement and elasticity. The polysilsesquioxane compound (C) includes at least one selected from the group consisting of compounds represented by the following general formula (1) or (2).

The polysilsesquioxane compound (C) is a structure in which an organic component is connected to a ceramic structure made of silicon and oxygen. The organic component may be selected from organic molecules such as acrylate, aryl, alkyl, amino, ester, epoxy, vinyl, fluorocarbon and the like, preferably the polyfunctional (meth) acrylate oligomer and It is preferable to introduce the same acrylate group as the polymerization reactive group of the acrylate monomer.

[Formula 1]

[Formula 2]

(In Formula 1 or Formula 2, R is an aliphatic or aromatic hydrocarbon having 2 to 80 carbon atoms containing 2 to 20 (meth) acrylate groups, and may or may not include a hetero atom.)

In Formula 1 or Formula 2, R may include 2 to 20 (meth) acrylate groups, and preferably 5 to 15 (meth) acrylate groups. When the (meth) acrylate group is contained within the above range, occurrence of stain in an environment of high temperature and high humidity can be prevented.

The polysilsesquioxane represented by Formula 1 or Formula 2 may be prepared using trichlorosilane having three hydrolyzable reactors as a monomer, and prepared using trialkoxysilane. The production method using the silane triol produced in the middle of reaction is known. In this case, when the polysilsesquioxane is prepared using the above compounds, the polysilsesquioxane may be prepared by a heat-condensation polymerization method. Commercially available products as polysilsesquioxanes represented by the general formula (1) or (2) include MA0736 (Hybrideplastic, Cage type) or Vitolane? SF1000MA (TWI, Ladder type) can be used.

The polysilsesquioxane compound (C) is preferably included 0.1 to 50 parts by weight, more preferably 5 to 20 parts by weight based on 100 parts by weight of the total hard coating composition. If the content of the polysilsesquioxane compound (C) is less than 0.1 parts by weight based on the above standards, it is difficult to produce a hard coating film having sufficient hardness, and when it exceeds 50 parts by weight, it is advantageous for hardness and curling, Cracks may occur in the hard coat layer.

Photoinitiator (D)

The photoinitiator (D) may be applied without limitation as long as it is generally used in the art. The photoinitiator (D) may be used at least one selected from the group consisting of hydroxy ketones, amino ketones and hydrogen decyclic photoinitiator.

Specific examples of the photoinitiator (D) are 2-methyl-1- [4- (methylthio) phenyl] -2-morphopropanone-1, diphenyl ketone benzyl dimethyl ketal, 2-hydroxy-2-methyl- 1-phenyl-1-one, 4-hydroxycyclophenylketone, dimethoxy-2-phenylatetophenone, anthraquinone, fluorene, triphenylamine, carbazole, 3-methylacetophenone, 4-knoloaceto At least one selected from the group consisting of phenone, 4,4-dimethoxyacetophenone, 4,4-diaminobenzophenone, 1-hydroxycyclohexylphenyl ketone, benzophenone, and the like can be used.

The photoinitiator (D) may be used in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the total hard coating composition. If the content of the photoinitiator (D) is less than 0.1 parts by weight based on the above standard, if the curing rate of the hard coating composition is slow and exceeds 10 parts by weight, cracks may occur in the hard coating layer cured by over curing.

Solvent (E)

The solvent (E) can be used without limitation so long as it is known as a solvent in the hard coating composition of the art.

Examples of the solvent (E) include alcohols (methanol, ethanol, isopropanol, butanol, methylcellulose, ethyl solusorb, etc.), ketones (methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, diethyl ketone, and dipropyl). Ketones, cyclohexanone and the like), hexane-based (hexane, heptane, octane and the like), benzene-based (benzene, toluene, xylene and the like) and the like can be used. The solvents exemplified above may be used alone or in combination of two or more.

The solvent (E) may be added 0.1 to 90 parts by weight based on 100 parts by weight of the total hard coating composition. If the solvent (E) is less than 0.1 parts by weight based on the above standard, the viscosity is high, the workability is low, and if it exceeds 90 parts by weight, it takes a lot of time in the curing process and there is a problem of low economic efficiency.

In addition to the above components, the hard coating composition according to the present invention includes an antioxidant, a UV absorber, a light stabilizer, a leveling agent, a surfactant, and an antifouling agent, which are generally used in the art within the scope of not deteriorating the effect of the present invention. It may further comprise one or two or more selected from.

The present invention provides a hard coat film manufactured using the above-described hard coat composition. That is, the hard coating film according to the present invention includes a hard coating layer formed by applying the above-described hard coating composition on one or both surfaces of the transparent substrate and then curing.

The hard coat film prepared by using the hard coating composition according to the present invention has excellent hardness and scratch resistance and exhibits a property of hardly curling phenomenon.

Any film can be used as long as the transparent substrate is a plastic film having transparency. Examples of the transparent substrate include cycloolefin derivatives having a unit of a monomer containing a cycloolefin such as norbornene or a polycyclic norbornene monomer, diacetyl cellulose, triacetyl cellulose, acetyl cellulose butyrate, and isobutyl Cellulose selected from ester cellulose, propionyl cellulose, butyryl cellulose or acetyl propionyl cellulose, ethylene-vinyl acetate copolymer, polyester, polystyrene, polyamide, polyetherimide, polyacryl, polyimide, polyether sulfone, poly Sulfone, polyethylene, polypropylene, polymethylpentene, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, polyvinyl acetal, polyether ketone, polyether ether ketone, polyether sulfone, polymethyl methacrylate, polyethylene terephthalate , Polybutyl Terephthalate, may be used polyethylene naphthalate, polycarbonate, polyurethane, may be used one selected from among epoxy, non-stretched uniaxially or biaxially stretched film.

Of these, preferred are monoaxially or biaxially oriented polyester films which are excellent in transparency and heat resistance, cycloolefin-based derivative films which are excellent in transparency and heat resistance and capable of coping with the enlargement of the film, transparency and optical anisotropy, An acetylcellulose film may suitably be used.

8-1000 micrometers is preferable and, as for the thickness of the said transparent base material, More preferably, it is 40-100 micrometers.

Application of the hard coating composition may be in a suitable manner such as die coater, air knife, reverse roll, spray, blade, casting, gravure and spin coating.

The preferred coating thickness of the hard coating composition is 3 ~ 200㎛. After coating, the hard coating composition is dried by evaporation of volatiles for 10 seconds to 1 hour, preferably 30 seconds to 10 minutes at a temperature of 30 ~ 150 ℃. Thereafter, the hard coating composition is cured by irradiating UV light. The irradiation amount of UV light is about 0.01-10 J / cm ² , preferably 0.1-2 J / cm ² .

The thickness of the hard coating layer is not limited, but is preferably in the range of 5 to 30 μm, more preferably in the range of 10 to 25 μm. When the thickness of the hard coating layer is within the above range, curling hardly occurs and a hard coating film having excellent hardness can be obtained.

The present invention provides a polarizing plate having excellent physical properties formed by laminating the above-described hard coating film on at least one surface of the polarizer.

The polarizer is not particularly limited, but various kinds may be used. Examples of the polarizer include polyvinyl alcohol-based films and polyvinyl uniaxially stretched by adsorbing a dichroic substance such as iodine or a dichroic dye to a hydrophilic polymer film such as an ethylene-vinylacetate copolymer-based partially saponified film. Polyene type orientation films, such as alcohol dehydration and polyvinyl chloride dehydrochlorination, etc. can be illustrated. Among these, the polarizer which consists of dichroic substances, such as a polyvinyl alcohol-type film and iodine, can be used preferably. Although the thickness of the said polarizing plate is not specifically limited, Generally, it is about 5-80 micrometers.

The present invention also provides a display device to which the above-described hard coating film is applied.

For example, the polarizing plate on which the hard coat film of the present invention is formed may be incorporated in an image display device, thereby providing an image display device to which the hard coat film according to the present invention is applied. Further, by attaching the hard coat film of the present invention to the window of the image display device, it is possible to provide an image display device to which the hard coat film according to the present invention is applied.

The hard coat film of the present invention can be preferably used in reflective, transmissive, semi-transmissive LCD or LCD of various driving methods such as TN type, STN type, OCB type, HAN type, VA type, IPS type and the like. In addition, the hard coat film of the present invention can be preferably used for various display devices such as plasma displays, field emission displays, organic EL displays, inorganic EL displays, electronic papers, and the like.

The present invention will be further illustrated by the following examples, which are only specific examples of the present invention, and are not intended to limit or limit the protection scope of the present invention.

Synthesis Example 1 Synthesis of Polyfunctional (meth) acrylate Oligomer Containing 4,4'-Dicyclohexyl Diisocyanate]

As a compound having within the molecule two groups over isocyanate 4,4' dicyclohexyl sildi diisocyanate (H ¹² -MDI, Bayer Co.), 88.26g, as a di (meth) acrylate monomers containing hydroxyl groups of pentaerythritol penta / hexa acrylate (FASCAT 4202, Akenama) as a reaction catalyst and 0.5 g of methoxyhydroquinone (HQMME, Eastmana) as a polymerization inhibitor were charged at room temperature And the reaction temperature was raised to 90 DEG C while stirring. The reaction was carried out at 90 DEG C for 12 hours, and the reaction was terminated when the characteristic peak of isocyanate of 2260 cm < ^-1 > in the infrared spectroscopic spectrum completely disappeared. Thus, a polyfunctional (meth) acrylate oligomer containing 4,4'-dicyclohexyldiisocyanate was synthesized.

Synthesis Example 2 Synthesis of Polyfunctional (meth) acrylate Oligomers Containing Trimers Derived from Hexamethylene Diisocyanate]

75 g of a trimer (N3300, Bayer) derived from hexamethylene diisocyanate as an organic compound having two or more isocyanate groups in the molecule, 75 g of a dipentaerythritol penta / hexaacrylate mixture (KAYARAD) as a (meth) acrylate monomer containing a hydroxyl group , Nippon Kayakusa), 0.5 g of dibutyltin dilaurate (FASCAT 4202, Akema) as a reaction catalyst and 0.25 g of methoxyhydroquinone (HQMME, Eastman) as a polymerization inhibitor were added at room temperature, And the reaction temperature was raised to 110 ° C. The reaction was carried out at 110 DEG C for 10 hours and the reaction was terminated when the characteristic peak of isocyanate of 2260 cm < ^-1 > in the infrared spectroscopic spectrum completely disappeared. Thus, a multifunctional (meth) acrylate oligomer containing a trimer derived from hexamethylene diisocyanate was synthesized.

EXAMPLES 1-12 AND COMPARATIVE EXAMPLES 1-3 Production of Hard Coating Composition

To prepare a composition for a hard coating with the components shown in Table 1 and Table 2

Composition Example One 2 3 4 5 6 7 8 9 Multifunctional (meth) acrylate oligomer (A) 20 20 15 10 5 9 20 20 (Meth) acrylate monomer (B) 20 17 18 18 17 9 18 20 17 Polysilsesquioxane (C-1) 2 5 9 14 20 24 24 Polysilsesquioxane (C-2) 2 5 Silica sol Solvent (E) MEK 35 35 35 35 35 35 35 35 35 MEC 20 20 20 20 20 20 20 20 20 Photoinitiator (D) I-184 2 2 2 2 2 2 2 2 2 additive BYK-378 One One One One One One One One One

Composition Example Comparative example 10 11 12 13 14 One 2 3 Multifunctional (meth) acrylate oligomer (A) 15 10 5 9 42 20 (Meth) acrylate monomer (B) 18 18 17 9 18 42 18 Polysilsesquioxane (C-1) Polysilsesquioxane (C-2) 9 14 20 24 24 Silica sol 24 Solvent (E) MEK 35 35 35 35 35 35 35 25 MEC 20 20 20 20 20 20 20 10 Photoinitiator (D) I-184 2 2 2 2 2 2 2 2 additive BYK-378 One One One One One One One One

Each component used in Table 1 and Table 2 is as follows.

Multifunctional (meth) acrylate oligomer (A)

(Meth) acrylate monomer (B):

Taerythritol tree / tetraacrylate (Miwon Corporation, M340)

Polysilsesquioxane (C):

MA0736 (Hybrideplastic, Cage type, C-1)

Vitolane? SF1000MA (TWI, Ladder type, C-2)

Silica sol (THRULYA 2320; catalyzed sand; average particle size: 50 nm; solids content: 20 parts by weight)

MEK: methyl ethyl ketone

MEC: Methyl Cellulose Solution

I-184: 1-hydroxycyclohexyl phenyl ketone (Shiba Corporation)

BYK-378: silicone modified oil (BYK)

<Experimental Example>

The hard coating composition prepared in the above Examples and Comparative Examples was applied with a meyer bar (a kind of gravure coater) to a thickness of 6㎛ on a transparent substrate film (80㎛, TAC) after stirring for 1 hour and then at 1 ℃ at 70 ℃ After drying for a minute, a hard coat film including a hard coat layer formed by curing at 500 mJ / cm ² was prepared. The prepared hard coat film was used as a protective layer of the iodine-based absorption dichroic polarizing plate.

In this case, the physical properties of the hard coat film prepared as described above were measured as follows, and the results are shown in Tables 3 and 4 below.

(1) transmittance and haze

The total light transmittance and the haze value were measured by using a spectrophotometer (HZ-1, manufactured by Suga Japan Co., Ltd.) toward the light source D65.

(2) pencil hardness

The hard coating layer of the prepared hard coating film was subjected to a 500g load with a pencil hardness tester (PHT, manufactured by Seokbo Science, Inc.), and the pencil hardness was measured. The pencil was made five times per pencil hardness using Mitsubishi products. If there were two or more gases, it was determined to be defective, and pencil hardness was indicated by a pencil before the failure occurred.

Kiss: 0 OK

Kiss: 1 OK

Ges: 2 or more NG

(3) scratch resistance

Scratch resistance was tested by reciprocating 10 times under 1 kg / (2 cm x 2 cm) using a steel wool tester (WT-LCM100, Korea Protec Co.).

Steel wool used # 0000.

A: 0 scratches

A ': 1 to 10 scratches

B: 11-20 scratches

C: 21-30 scratches

D: 31 or more scratches

(4) Adhesion

Eleven straight lines were drawn on the coated surface of the film at intervals of 1 mm each to form 100 squares, and then three peel tests were conducted using a tape (CT-24, Nichi Nippon Corp.). Three 100 squares were tested and averaged. The adhesion was recorded as follows.

Adhesion = n / 100

n: number of rectangles not peeled off

100: total squares

Therefore, when none of the peeling was recorded as 100/100.

(5) curling

The sample cut into the square shape of A4 size (29.7 X 21.0 cm) was placed on a flat glass plate with the coated surface of the film facing up, and the distance from the square glass plate was measured at 25? And 50% RH, and then averaged. Was taken as a measured value.

Very good: 0 to 15 mm or less, Good: 15 mm to 30 mm or less, Poor: 30 mm to 50 mm or less, Very poor: 50 mm or more.

Example One 2 3 4 5 6 7 8 9 Total light transmittance 92 92 92 92 91 91 92 91 91 Hayes 0.2 0.2 0.2 0.2 0.3 0.2 0.3 0.2 0.2 Pencil hardness 3H 4H 5 H 5H 5H 5H 4H 4 H 5 H Scratch resistance A A A A A A A A A Adhesiveness 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 curling Good Good Good Good Good Good Good Good Good

Example Comparative example 10 11 12 13 14 One 2 3 Total light transmittance 91 91 91 91 92 91 92 92 Hayes 0.2 0.3 0.2 0.3 0.2 0.2 0.2 0.4 Pencil hardness 5 H 5H 5H 5H 4H 2 H 2 H 2H Scratch resistance A A A A A C B A ' Adhesiveness 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 100
/ 100 curling Good Good Good Good Good Bad Very bad Bad

As shown in Tables 3 and 4, in the case of the hard coating composition comprising the polysilsesquioxane compound represented by Chemical Formula 1 or Chemical Formula 2 according to the present invention, the hardness, In addition to excellent scratch resistance and adhesion, it can be confirmed that curling hardly occurs.

Claims (7)

Hard coating composition comprising a polysilsesquioxane compound (C) represented by the following formula (1) or (2).
[Formula 1]

(2)

(In Formula 1 or Formula 2, R is an aliphatic or aromatic hydrocarbon having 2 to 80 carbon atoms containing 2 to 20 (meth) acrylate groups, and may or may not include a hetero atom.) The method according to claim 1,
The hard coating composition comprising a polyfunctional (meth) acrylate oligomer (A), a (meth) acrylate monomer (B), a photoinitiator (D) and a solvent (E). The method according to claim 1,
The polysilsesquioxane compound (C) is a hard coating composition, characterized in that it comprises 0.1 to 50 parts by weight based on 100 parts by weight of the total hard coating composition. The method according to claim 2,
1 to 80 parts by weight of the (meth) acrylate oligomer (A), 1 to 70 parts by weight of the (meth) acrylate monomer (B), and the polysilsesquioxane compound based on 100 parts by weight of the total hard coating composition. (C) 0.1 to 50 parts by weight, 0.1 to 90 parts by weight of the photoinitiator (D) and 0.1 to 90 parts by weight of the solvent (E) comprises a hard coating composition. Hard coating film according to any one of claims 1 to 4 comprising a hard coating layer formed by applying a hard coating composition on one or both sides of the transparent substrate and then curing. The hard coating film of claim 5 is provided, characterized in that the polarizing plate. The hard coating film of claim 5 is provided.