KR101057734B1 - Acrylate having high refractive index and manufacturing method thereof - Google Patents

Abstract

The present invention relates to a photocurable resin composition comprising an acrylate having a high refractive index represented by the following general formula (1) or (2), and because the acrylate has a high refractive index, it is widely used in display component materials such as prism sheets. It can be used and it is characterized by the simple manufacturing process, high efficiency and economical.

(1) (2)

Description

Acrylate having a high refractive index and its manufacturing method {High Refractive Acrylate and the method for preparing the same}

The present invention relates to an acrylate and a method for manufacturing the same, and more particularly, a novel acrylate having a high refractive index that can be used for display component materials such as an optical film, a method for preparing the same, and a photocurable material including the acrylate monomer. It relates to a resin composition and an optical film using the same.

High refractive organic materials are used in various fields such as LCD prism sheets, light guide plates, film materials for organic light emitting diodes (OLEDs), AR film materials for PDPs, and optical lenses.

Among these, the prism sheet is used for the purpose of improving the brightness of the backlight unit disposed on the rear side of the liquid crystal display (LCD). In order to increase the brightness of the backlight unit, the light flow of the backlight unit should be appropriately used. Using a three-dimensional structure that can appropriately modify the interference, diffraction, polarization and light particle principles of light can control the light flow, and modifying the physical properties of the materials that make up the three-dimensional structure can further control the flow of light. It is known that the direction of the light particles can be aligned in the direction desired by the user, thereby improving the luminance in the direction.

In addition, an important optical parameter of the material constituting the prism layer of the prism sheet is a refractive index. Since a higher refractive index improves the performance of the prism film, a prism sheet having a high refractive index may increase the efficiency of the LCD backlight. Can be.

In general, the prism layer of the prism sheet is a polymer resin capable of polymerization by free radicals, and in particular, a photocurable resin is often used. Representative examples of the photocurable polymer material having a high refractive index include (meth) acrylates containing one or two or more aromatic groups or (meth) acrylates containing halogen or sulfur. Proper mixing is performed to produce a prism sheet and applied to the backlight unit. As a specific example, an optical product made of a polymerizable composition comprising a brominated monomer having a high refractive index is disclosed in Korean Patent Laid-Open Publication No. 2001-0012340 and Korean Patent Publication No. 10-2005-0010760.

However, conventionally used halogen compounds are highly toxic, and when burned, there is a problem in that they emit corrosive gases and a large amount of soot. In addition, sulfur compounds are oxidized over time, yellowing appears, which has the disadvantage that the transmittance is lowered. Various studies are being conducted to improve these problems, but domestic development of non-halogen acrylates is in no state, so it is dependent on imports.

In addition, the high refractive resin composition for forming the prism layer of the prism sheet should be stable to ultraviolet rays, and at the same time, it must maintain sufficient adhesive force and firmly increase the surface strength to support the transparent substrate film and the high refractive polymer resin. do. In addition, if the viscosity of the high refractive index composition is too high, there is a difficulty in processing, it is preferable to maintain a liquid state at room temperature.

At present, it is urgently required to develop a new high-refractive organic material having a price competitiveness in the manufacturing process while satisfying all of the above conditions.

The first problem to be solved by the present invention is to provide a novel acrylate compound having a high refractive index.

The second problem to be solved by the present invention is to provide a method for producing the acrylate compound having a high refractive index.

The third problem to be solved by the present invention is to provide a thermosetting resin composition comprising the acrylate compound.

The fourth problem to be solved by the present invention is to provide an optical film prepared using the thermosetting resin composition.

The fifth problem to be solved by the present invention is to provide a display device employing the optical film.

The present invention provides an acrylate compound represented by the following formula (1) or (2) in order to achieve the first object.

             (1) (2)

Wherein R ₁ is H, C ₁ -C ₆ alkyl, -OR ', -NR' ₂ , -CN, -NO ₂ , -CHO, -COR ', -COOR' (R 'is methyl, ethyl , Propyl), R ₂ is H or CH ₃ )

According to one embodiment of the present invention, the acrylate compound having a high reduction rate is 1,3-bis (1-naphthoxy) propan-2-yl acrylate represented by the following general formula (3) or the following general formula (4) It is preferable that it is 1, 3-bis (2-naphthoxy) propan-2-yl acrylate represented by.

            (3) (4)

In order to achieve the second object of the present invention, 1,3-bis (1-naphthoxy) -2-propanol of formula (5) or 1,3-bis (2-naphthoxy of formula (6) A method for preparing an acrylate compound of formula (3) or formula (4) from-)-2-propanol is provided according to the following scheme.

            (5) (3)

(6) (4)

(6) (4)

According to one embodiment of the present invention, 1,3-bis (1-naphthoxy) -2-propanol of formula (5) is a 1-naphthyl glycidyl ether of formula (7) Can be prepared by reacting 1-naphthol).

      (7) (8) (5)

According to another embodiment of the present invention, 1,3-bis (2-naphthoxy) -2-propanol of formula (6) is a 2-naphthyl glycidyl ether of formula (9) It can be prepared by reacting 2-naphthol of 10).

      (9) (10) (6)

The present invention to achieve the third object,

40 to 60% by weight of the acrylate monomer of the formula (1) or (2),

30-50% by weight of reactive acrylate monomer having at least one functional group and

It provides a photocurable resin composition comprising 1 to 5% by weight of a photopolymerization initiator.

According to one embodiment of the invention, the reactive acrylate monomer having at least one functional group is phenoxy ethyl acrylate, phenoxy diethylene glycol acrylate, phenoxy tetra ethylene glycol acrylate, phenoxy hexaethylene glycol acrylate, Dicyclo pentadiene acrylate, 4-hydroxy butyl acrylate and cyclohexane di methanol mono acrylate, tripropylene glycol diacrylate, polyethylene glycol diacrylate, tris (2-hydroxyethyl) isocyanurate diacryl Ethylene, Dimethylol Tricyclo Decane Diacrylate and Ethylene Oxide Addition Bisphenol A Diacrylate, Ethylene Oxide 3 Mole Addition Trimethylol Propane Triacrylate, Ethylene Oxide 6 Mole Addition Trimethylol Propane Triacrylate, Pentaery It may be a compound selected from the group consisting of tritol triacrylate, tris (acryloxyethyl) isocyanurate, dipentaerythritol hexa acrylate or caprolactone modified dipentaerythritol hexa acrylate.

According to another embodiment of the present invention, the photopolymerization initiator is benzophenone, benzophenone derivative, benzoin, benzoin alkyl ether benzyl dimethyl ketal, 1-hydroxy cyclohexyl phenyl ketone, diethoxy acetophenone, phosphine oxide type , Amino acetophenone series, 2-hydroxy-2-methyl-1-phenylpropano-1-non, 2-benzyl-2-dimethylamide-1- (4-morpholina phenyl) -butanane It may be a compound selected from one or more from.

The present invention provides an optical film, characterized in that produced using a photocurable resin composition containing an acrylate represented by the formula (1) or (2) to achieve the fourth object, the optical The film may for example be a prism sheet.

The present invention provides a display device, which is manufactured by employing the optical film in order to achieve the fifth object.

Since the new acrylate according to the present invention has a very high refractive index, it can be widely used in display part materials such as prism sheets, and is a simple acrylated reaction using an aromatic compound which is relatively inexpensive and can recover unreacted materials as a starting material. It can be manufactured by performing a high economical and commercialization possibility. In addition, since it is environmentally friendly as a non-halogen substance, it is not applicable to environmental regulations and thus is more likely to be used.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated in detail.

Looking at the results reported so far, the study was carried out using a compound having an aromatic functional group as a starting material, because the aromatic compounds such as naphthalene have a planar structure, the molecular accumulation can be very dense. Such a dense structure can increase the electron density, thereby improving the glass transition temperature (Tg) and the refractive index. Based on this concept, the present inventors synthesized a material having a high refractive index by performing an acrylated reaction after making the aromatic compound into glycidyl ether form.

The acrylate compound having a high refractive index according to the present invention is characterized by being a compound represented by the following general formula (1) or (2).

             (1) (2)

Wherein R ₁ is H, C ₁ -C ₆ alkyl, -OR ', -NR' ₂ , -CN, -NO ₂ , -CHO, -COR ', -COOR' (R 'is methyl, ethyl , Propyl), R ₂ is H or CH ₃ )

According to one embodiment of the present invention, the acrylate compound having a high reduction rate is 1,3-bis (1-naphthoxy) propan-2-yl acrylate represented by the following general formula (3) or the following general formula (4) It is preferable that it is 1, 3-bis (2-naphthoxy) propan-2-yl acrylate represented by.

          (3) (4)

According to the present invention, the acrylate compound of formula (3) or formula (4) may be selected from 1,3-bis (1-naphthoxy) -2-propanol of formula (5) or 1, From 3-bis (2-naphthoxy) -2-propanol it can be prepared according to the following scheme:

      (5) (3)

              (6) (4)

In addition, according to one embodiment of the present invention, 1,3-bis (1-naphthoxy) -2-propanol of the formula (5) is 1-naphthyl glycidyl ether of the formula (7) It can manufacture by reacting 1-naphthol of 8).

       (7) (8) (5)

According to another embodiment of the present invention, 1,3-bis (2-naphthoxy) -2-propanol of the formula (6) is a 2-naphthyl glycidyl ether of the formula (9) It can manufacture by making 2-naphthol of (10) react.

      (9) (10) (6)

On the other hand, the photocurable resin composition comprising an acrylate monomer according to the present invention is 40 to 60% by weight of the acrylate monomer of the formula (1) or (2), and 30 to 50% by weight of a reactive acrylate monomer having at least one functional group And 1 to 5% by weight of the photopolymerization initiator. In the photocurable resin composition according to the present invention, when the acrylate monomer is used in an amount of more than 50% by weight, the viscosity becomes high, which makes it difficult to cast the film. When the photopolymerization initiator is used in excess, physical properties such as refractive index are lowered. It is preferable to form a photocurable resin in the same content.

According to one embodiment of the invention, the reactive acrylate monomer having at least one functional group is phenoxy ethyl acrylate, phenoxy diethylene glycol acrylate, phenoxy tetra ethylene glycol acrylate, phenoxy hexaethylene glycol acrylate, Dicyclo pentadiene acrylate, 4-hydroxy butyl acrylate and cyclohexane di methanol mono acrylate, tripropylene glycol diacrylate, polyethylene glycol diacrylate, tris (2-hydroxyethyl) isocyanurate diacryl Ethylene, Dimethylol Tricyclo Decane Diacrylate and Ethylene Oxide Addition Bisphenol A Diacrylate, Ethylene Oxide 3 Mole Addition Trimethylol Propane Triacrylate, Ethylene Oxide 6 Mole Addition Trimethylol Propane Triacrylate, Pentae Tree toll may be triacrylate, tris (acryloxyethyl) isocyanate compound, New acrylate, dipentaerythritol hexaacrylate or caprolactone-modified dipentaerythritol at least one selected from the group consisting of hexaacrylate.

According to another embodiment of the present invention, the photopolymerization initiator is benzophenone, benzophenone derivative, benzoin, benzoin alkyl ether benzyldimethyl ketal, 1-hydroxy cyclohexyl phenyl ketone, diethoxy acetophenone, phosphine oxide type , Amino acetophenone series, 2-hydroxy-2-methyl-1-phenylpropano-1-non, 2-benzyl-2-dimethylamide-1- (4-morpholinaphenyl) -butanane It may be a compound selected from one or more from.

In another aspect, the present invention provides an optical film, which is prepared using a photocurable resin composition comprising an acrylate according to the formula (1) or (2), the optical film may be, for example, a prism sheet have.

In another aspect, the present invention provides a display device characterized in that the manufacturing using the optical film.

Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited thereby.

Example 1- (1): Synthesis of 1-naphthyl glycidyl ether using 1-naphthol

KOH (0.295 g, 5.0 mmol) was added to a 50 mL round bottom flask using 1-naphthol (0.721 g, 5.0 mmol) as a starting material, followed by stirring with methanol. When the reaction reagents were completely dissolved in the reaction solvent, the solvent was completely removed using an evaporator and freeze-pump-thaw to obtain dried potassium salt. After raising the temperature of the oil bath to 60 ~ 90 ℃, the flask was immersed in the oil bath and epichlorohydrin (3.91 mL, 10.0 mmol) using a solvent and reagent was carried out for 30 minutes at 60 ℃. After the reaction, the reaction solution was washed with brine, and the product was extracted from the aqueous solution using a sufficient amount of CH ₂ Cl ₂ . Moisture was removed by Na ₂ SO ₄ , and the solvent was removed under reduced pressure. Silica gel column chromatography (Rf = 0.20, hexane: ethyl acetate = 16: 1, v / v) was performed from the crude product to obtain 1-naphthyl glycidyl ether (0.881 g, 88%).

¹ H NMR (CHCl ₃ ): δ 8.31 (m, 1 H, H at ArH), 7.82 (m, 1 H, H at ArH), 7.49 (m, 3 H, Hs at ArH), 7.38 (m, 1 H, H at ArH), 6,82 (m, 1 H, H at ArH), 4.41 (m, 1 H, H at C-3), 4.15 (m, 1 H, H at C-3), 3.50 (m, 1 H, H at C-2), 2.98 (m, 1 H, H at C-1), 2.87 (m, 1 H, H at C-1)

Example 1- (2): Synthesis of 1,3-bis (1-naphthoxy) -2-propanol with 1-naphthyl glycidyl ether

Tetrabutylammonium bromide (0.322 g, 1 mmol) and 1-naphthol (0.865 g, 6 mmol) were added to a 50 mL round bottom flask, starting with 1-naphthyl glycidyl ether (1.0 g, 5.0 mmol). The reaction was carried out at 110 ° C. for 4 hours and 30 minutes while refluxing with toluene as a solvent. Silica gel chromatography (Rf = 0.15, hexane: ethyl acetate = 9: 1, v / v) was carried out from the obtained crude product to give 1,3-bis (1-naphthoxy) -2-propanol (1.55 g, 90%) Could get

¹ H NMR (CDCl ₃ ): δ 8.27 (m, 2 H, Hs at ArH), 7.82 (m, 2 H, Hs at ArH), 7.49 (m, 6 H, Hs at ArH), 7.38 (t, J = 7.2 Hz, 2 H, Hs at ArH), 6.90 (d, J = 7.2 Hz, 2 H, Hs at ArH), 4.73 (m, 1 H, H at C-2), 4.46 (m, 4 H, Hs at C-1), 2.74 (d, J = 5.4 Hz, 1 H, Hs at OH)

Example 1- (3): Synthesis of 1,3-bis (1-naphthoxy) propan-2-yl acrylate using 1,3-bis (1-naphthoxy) -2-propanol

Starter 1,3-bis (1-naphthoxy) -2-propanol (0.7045 g, 2.0 mmol) was added to a 50 mL round bottom flask and dissolved in a small amount of methylene chloride. Triethylamine (0.5817 mL, 4.09 mmol) Was added and stirred. Acryloyl chloride (0.2553 mL, 3.068 mmol) was added dropwise under 0 ° C. and the reaction was carried out for 20 minutes while maintaining the 0 ° C. condition. After the reaction, the reaction solution was washed with NaHCO ₃ aqueous solution, and the product was extracted from the aqueous solution using a sufficient amount of methylene chloride.

Water was removed by MgSO ₄ and solvent was removed under reduced pressure. Silica gel column chromatography (Rr = 0.25, hexane: ethyl acetate = 15: 1, v / v) was carried out from the obtained product to give 1,3-bis (1-naphthoxy) propan-2-yl acrylate (0.6074 g, 71%).

¹ H NMR (CDCl ₃ ): δ 8.25 (m, 2 H, Hs at ArH), 7.74 (m, 2 H, Hs at ArH), 7.42 (m, 6 H, Hs at ArH), 7.30 (m, 2 H, Hs at ArH), 6.76 (d, J = 7.5 Hz, 2 H, Hs at ArH), 6.47 (dd, J = 17.1, 1 Hz, 1 H, H at C-3 '6.16 (qd, J = 17.4, 10.5, 1 Hz, 1 H, H at C-2 '5.89 (m, 1 H, H at C-2), 5.77 (dd, J = 10.5, 1 Hz, 1 H, H at C-3' 4.44 (m, 4H, Hs at C-1)

¹³ C NMR (CDCl ₃ ): δ 165.79, 154.27, 134.70, 131.99, 128.22, 127.70, 126.73, 125.96, 125.75, 125.64, 122.10, 121.15, 105.18, 70.74, 66.97

Example 2- (1): Synthesis of 2-naphthyl glycidyl ether using 2-naphthol

KOH (1.48 g, 25.0 mmol) was added to a 50 mL round bottom flask using 2-naphthol (3.67 g, 25.0 mmol) as a starting material, followed by stirring with methanol. When the reaction reagents were completely dissolved in the reaction solvent, the solvent was completely removed using an evaporator and freeze-pump-thaw to obtain dried potassium salt. After raising the temperature of the oil bath to 60 ~ 90 ℃, the flask was immersed in the oil bath and epichlorohydrin (19.56 mL, 250 mmol) was used as a solvent and reagent for 30 minutes at 60 ℃. After the reaction, the reaction solution was washed with brine, and the product was extracted from the aqueous solution using a sufficient amount of CH ₂ Cl ₂ . Moisture was removed by Na ₂ SO ₄ , and the solvent was removed under reduced pressure. Silica gel column chromatography (Rf = 0.20, hexane: ethyl acetate = 16: 1, v / v) was performed from the crude product to obtain 2-naphthyl glycidyl ether (4.615 g, 92%).

¹ H NMR (CDCl ₃ ): δ 7.75 (m, 3 H, Hs at ArH), 7.44 (m, 1 H at ArH), 7.35 (m, 1 H, ArH), 7.17 (m, 2 H, Hs at ArH), 4.35 (dd, J = 11.1, 3 Hz, 1 H, H at C-3), 4.07 (dd, J = 11.3, 6 Hz, 1 H, H at C-3), 3.44 (m, 1 H, H at C-2), 2.95 (t, J = 4.5 Hz, 1 H, Hs at C-1), 2.82 (q, J = 2.4 Hz, 1 H, H at C-1)

Experimental Example 2- (2): Synthesis of 1,3-bis (2-naphthoxy) -2-propanol using 2-naphthyl glycidyl ether

Tetrabutylammonium bromide (0.081 g, 0.25 mmol) and 2-naphthol (0.441 g, 3 mmol) were added, starting with 2-naphthol glycidyl ether (0.5 g, 2.5 mmol), and toluene was used as a solvent. At reflux, the reaction was carried out at 110 ° C. for 2 hours 30 minutes. Silica gel column chromatography (Rf = 0.2, hexane: ethyl acetate = 5: 1, v / v) was carried out from the obtained crude product to give 1,3-bis (2-naphthoxy) -2-propanol (0.7579 g, 88% Could get.

¹ H NMR (CDCl ₃ ): δ 7.76 (m, 6 H, Hs at ArH), 7.45 (td, J = 7.2, 1.5 Hz, 2 H, Hs at ArH), 7.35 (m, 2 H, Hs at ArH ), 7.20 (m, 4 H, Hs at ArH), 4.54 (m, 1 H, Hs at C-2), 4.33 (m, 4 H, Hs at C-1), 2.68 (d, J = 4.8 1 H, Hs at OH)

Example 2- (3): Synthesis of 1,3-bis (2-naphthoxy) propan-2-yl acrylate using 1,3-bis (2-naphthoxy) -2-propanol

Starter 1,3-bis (2-naphthoxy) -2-propanol (0.5166 g, 1.5 mmol) was added to a 50 mL round bottom flask and dissolved in a small amount of methylene chloride. Triethylamine (0.4243 mL, 3 mmol) Was added and stirred. Acryloyl chloride (0.2553 mL, 3.068 mmol) is added dropwise under 0 ° C. The reaction was carried out for 30 minutes while maintaining the 0 ° C condition. After the reaction, the reaction solution was washed with NaHCO ₃ aqueous solution, and the product was extracted from the aqueous solution using a sufficient amount of methylene chloride. Water was removed by MgSO ₄ and solvent was removed under reduced pressure. Silica gel column chromatography (Rr = 0.3, hexane: ethyl acetate = 10: 1, v / v) was carried out from the obtained product to give 1,3-bis (2-naphthoxy) propan-2-yl acrylate (0.47 g, 75%).

¹ H NMR (CDCl ₃ ): δ 7.77 (m, 5 H, H at ArH), 7.45 (m, 2 H, Hs at ArH), 7.36 (m, 2 H, Hs at ArH), 7.20 (m, 4 H, Hs at ArH), 6.53 (dd, J = 17.1, 1.5 Hz, 1 H, H at C-3 '6.23 (dd, J = 17.4, 10.2 Hz, 1 H, H at C-2', 5.92 ( dd, J = 10.2, 1.5 Hz, 1 H at C-3 '5.75 (m, 1 H, H at C-1), 4.49 (d, J = 5.4 Hz, 4 H, Hs at C-2)

¹³ C NMR (CDCl ₃ ): δ 165.90, 156.64, 134.71, 132.20, 129.84, 129.48, 128.32, 127.95, 127.13, 126.78, 124.19, 119.02, 107.32, 70.87, 66.47

Experimental Example 1: Refractive Index Measurement

1,3-bis (1-naphthoxy) propan-2-yl acrylate prepared from Example 1 and 1,3-bis (2-naphthoxy) propan-2-yl acrylate prepared from Example 2 The Abbe Refractometer NAR-1T Solid Refractometer was measured at 20 ° C Neat condition to obtain the following refractive index values. This value is considerably higher than that of conventional acrylates, and is expected to have a very good brightness enhancement effect when used in products such as optical films.

division Chemical formula Refractive Index

Example 1: 1,3-bis (1-naphthoxy) propan-2-yl acrylate

1.6259

Example 2: 1,3-bis (2-naphthoxy) propan-2-yl acrylate

1.6208

Experimental Example 2: Melting Point Measurement

As a result of measuring the melting point of the acrylates prepared in Examples 1 and 2, 1,3-bis (1-naphthoxy) propan-2-yl acrylate was a viscous solid material, 1,3 -Bis (2-naphthoxy) propan-2-yl acrylate was measured at 122-123 degreeC.

Example 3: Preparation of Photocurable Resin Composition

40 to 60% by weight of the acrylate monomers synthesized in Examples 1 and 2 were mixed with 30 to 50% by weight of the reactive acrylate monomer having 1 or more functional groups and 1 to 5% by weight of the photopolymerization initiator to form a photocurable resin composition. It can manufacture. In this embodiment, 50% by weight of 1,3-bis (1-naphthoxy) propan-2-yl or 1,3-bis (2-naphthoxy) propan-2-yl as the reactive acrylate and the reactive acrylate monomer 45 wt% of phenoxy hexaethylene glycol acrylate was used, and 5 wt% of 2-hydroxy-2-methyl-1-phenylpropa-1-non was used as the photopolymerization initiator.

Example 4: Preparation of Optical Film

The photocurable resin composition prepared in Example 3 was irradiated with UV light in the direction of the transparent base film in a state of contacting the coating surface of the transparent base film (PET film) to photocuring the composition coated on the frame, the transparent base film A prism optical film having a prism layer formed on one surface of the transparent substrate film was prepared by separating the coated and cured coating layer.

1 is a ¹ H NMR graph of 1-naphthyl glycidyl ether.

2 is a ¹ H NMR graph of 2-naphthyl glycidyl ether.

3 is a ¹ H NMR graph of 1,3-bis (1-naphthoxy) -2-propanol.

4 is a ¹ H NMR graph of 1,3-bis (2-naphthoxy) -2-propanol.

5 is a ¹ H NMR graph of 1,3-bis (1-naphthoxy) propan-2-yl acrylate.

Figure 6 is a ¹ H NMR graph of 1,3-bis (2-naphthoxy) propan-2-yl acrylate.

7 is a ¹³ C NMR graph of 1,3-bis (1-naphthoxy) propan-2-yl acrylate.

8 is a ¹³ C NMR graph of 1,3-bis (2-naphthoxy) propan-2-yl acrylate.

9 is an IR spectrum of 1,3-bis (1-naphthoxy) propan-2-yl acrylate.

10 is an IR spectrum of 1,3-bis (2-naphthoxy) propan-2-yl acrylate.

11 is a High Resolution Mass spectrum of 1,3-bis (1-naphthoxy) propan-2-yl acrylate.

12 is a High Resolution Mass spectrum of 1,3-bis (2-naphthoxy) propan-2-yl acrylate.

Claims (14)

delete delete delete delete delete delete delete delete 40 to 60% by weight of an acrylate monomer represented by the following formula (1) or (2), 30-50% by weight of reactive acrylate monomer having at least one functional group and A photocurable resin composition comprising 1 to 5% by weight of a photopolymerization initiator:

(One)

(2) (Wherein R ₁ is H, C ₁ -C ₆ alkyl, -OR ', -NR' ₂ , -CN, -NO ₂ , -CHO, -COR '-COOR' (R '= methyl, ethyl, propyl) Selected from the group and R ₂ is H or CH ₃ ) 10. The method of claim 9, Reactive acrylate monomers having at least one functional group include phenoxy ethyl acrylate, phenoxy diethylene glycol acrylate, phenoxy tetraethylene glycol acrylate, phenoxy hexaethylene glycol acrylate, dicyclo pentadiene arclate, 4 -Hydroxy butyl acrylate and cyclohexane di methanol mono acrylate, tripropylene glycol diacrylate, polyethylene glycol diacrylate, tris (2-hydroxyethyl) isocyanurate diacrylate, dimethylol tricyclodecane di Acrylate and ethylene oxide addition bisphenol A diacrylate, ethylene oxide 3 mole addition trimethylol propane triacrylate, ethylene oxide 6 mole addition trimethylol propane triacrylate, pentaerythritol triacrylate, Switch (acryloyl oxyethyl) isocyanate New acrylate, dipentaerythritol hexaacrylate or caprolactone-modified dipentaerythritol optical path, characterized in that compounds of at least one selected from the group consisting of hexadecyl acrylate resin composition. 10. The method of claim 9, The photopolymerization initiator is benzophenone, benzophenone derivative, benzoin, benzoin alkyl ether benzyldimethyl ketal, 1-hydroxy cyclohexyl phenyl ketone, diethoxy acetophenone, phosphine oxide type, amino acetophenone type, 2-hydroxy It is a compound selected from the group consisting of 2-methyl-1-phenylpropano-1-non, 2-benzyl-2-dimethylamide-1- (4-morpholinaphenyl) -butanane Photocurable resin composition. An optical film produced by using the photocurable resin composition according to claim 9. The optical film according to claim 12, which is a prism sheet. The display apparatus which employ | adopted the optical film of Claim 12.

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