KR20170024836A - Organic-inorganic hybrid composition with high refractive index - Google Patents
Organic-inorganic hybrid composition with high refractive index Download PDFInfo
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- KR20170024836A KR20170024836A KR1020150120366A KR20150120366A KR20170024836A KR 20170024836 A KR20170024836 A KR 20170024836A KR 1020150120366 A KR1020150120366 A KR 1020150120366A KR 20150120366 A KR20150120366 A KR 20150120366A KR 20170024836 A KR20170024836 A KR 20170024836A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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Abstract
There is provided a high refractive index organic hybrid composition capable of producing a prism film having a high refractive index. The high refractive index organic hybrid composition according to the present invention includes a composition for a prism film comprising an acrylate monomer having a polycyclic aromatic skeleton structure and a photoinitiator, and high refractive index ceramic nanoparticles.
Description
The present invention relates to a high refractive index organic hybrid composition, and more particularly, to a high refractive index organic hybrid composition capable of producing a prism film having a high refractive index.
The prism film is used for the purpose of improving the brightness of the backlight unit disposed on the rear surface of the liquid crystal display (LCD). Various attempts have been made to increase the brightness of the backlight unit. In order to increase the brightness of the backlight unit, it is possible to use the light flow of the backlight unit appropriately.
Conventionally, a film made to have a special three-dimensional structure is used for increasing the front luminance of the light source device. These are prism layers having a structured surface on one side and a smooth surface on the other side and a plurality of isosceles triangles arranged side by side on the structured surface are arranged linearly at an angle of about 45 degrees with the smooth surface. Then, a brightness enhancement film (hereinafter, referred to as a prism film) was used in which two films having the above-mentioned prism layer were turned by about 90 ° and used in a superimposed manner.
One important optical parameter of the prism layer of the prism film is the refractive index. The higher the refractive index, the better the performance of the prism film. The prism film having such a high refractive index is used to increase the efficiency of the LCD backlight .
In particular, the composition for forming a prism layer of a prism film must satisfy both conditions of maintaining a sufficient adhesive force and conditions capable of increasing surface strength. In addition, if the viscosity of the high refractive index composition is high, there is difficulty in processing, so it is desirable to maintain the liquid state at room temperature.
Therefore, as a composition for forming a prism film, it is required to develop a technique for a prism film having a high refractive index in order to increase the brightness of a backlight unit while satisfying various conditions.
SUMMARY OF THE INVENTION It is an object of the present invention to provide a high refractive index organic hybrid composition capable of producing a prism film having a high refractive index.
According to an aspect of the present invention, there is provided a composition for a prism film comprising an acrylate monomer having a polycyclic aromatic skeleton structure and a photoinitiator; And high refractive index ceramic nanoparticles.
The polycyclic aromatic skeleton structure may be at least one of a naphthalene structure and a phenanthrene structure.
The high refractive index ceramic nanoparticles may be at least one of titanium oxide, zirconium oxide, niobium oxide and cerium oxide.
The high refractive index ceramic nanoparticles may be contained in an amount of 20 to 80 parts by weight based on 100 parts by weight of the high refractive index organic hybrid composition.
The high refractive index organic hybrid composition may have a refractive index of 1.65 to 1.80.
According to another aspect of the present invention, there is provided a composition for a prism film comprising an acrylate monomer having a polycyclic aromatic skeleton structure and a photoinitiator; And a high refractive index organic-inorganic hybrid composition including a high refractive index ceramic nanoparticle.
INDUSTRIAL APPLICABILITY As described above, according to the embodiments of the present invention, it is possible to obtain a hybrid organic-inorganic hybrid composition having a refractive index higher than that of conventional products, thereby further enhancing the brightness of the prism film.
Hereinafter, embodiments of the present invention will be described.
According to one embodiment of the present invention, there is provided an acrylic resin composition comprising: an acrylate monomer including a polycyclic aromatic skeleton; And a photoinitiator.
The acrylate monomer according to the present invention is an acrylate monomer containing a polycyclic aromatic skeleton. In particular, the acrylate monomer of the present invention may include a naphthalene structure or a phenanthrene structure as a polycyclic aromatic skeleton structure.
When the polycyclic aromatic skeleton structure is a naphthalene structure, the acrylate monomer may be an acrylate monomer represented by the following formula (1).
[Chemical Formula 1]
Alternatively, when the polycyclic aromatic skeleton structure is a phenanthrene structure, the acrylate monomer may be an acrylate monomer represented by the following formula (2).
(2)
When the acrylate monomer contains a polycyclic aromatic skeleton such as naphthalene or phenanthrene, when the resin composition is prepared using such an acrylate monomer, a high refractive index can be obtained even with the resin composition itself.
This is because naphthalene and phenanthrene are in a structure in which benzene rings on the plate are directly opposed to each other, so that the benzene rings can give higher refractive index characteristics to the composition for the prism film than other compounds to which the benzene rings are connected. In addition, naphthalene or phenanthrene has a relatively low melting point as compared with bisphenolene, so that it can maintain a liquid state at room temperature after reacting with an acrylic functional group. The composition for a prism film exhibits a high refractive index and a high viscosity in many cases. In this case, since the handling property in the subsequent prism film processing step is low, problems such as an increase in manufacturing cost and product defects occur, .
The acrylate monomer according to the present invention can be prepared by reacting an alcohol having a polycyclic aromatic skeleton structure with acrylic acid to form an acrylate monomer having a polycyclic aromatic skeleton structure. That is, the alcohol containing a polycyclic aromatic skeleton structure reacts with acrylic acid to form an acrylate monomer. The alcohol which can be used in the present invention is preferably a compound having a high reactivity with acrylic acid even if it contains a polycyclic aromatic skeleton structure because the number of carbon atoms is not large such as methanol or ethanol. In particular, methanol may be used as the alcohol. When methanol is used as the alcohol, methyl acrylate monomers can be obtained.
When the polycyclic aromatic skeleton structure is a naphthalene structure and the alcohol is methanol, the acrylate monomer according to the present invention is prepared by the reaction shown in Reaction Scheme 1 below.
[Reaction Scheme 1]
If the polycyclic aromatic skeleton structure is a phenanthrene structure, the acrylate monomer according to the present invention is prepared by the reaction shown in Reaction Scheme 2 below.
[Reaction Scheme 2]
The acrylate monomer production process comprises a synthesis step, a water washing and neutralization step, a filtration step, and a concentration step. First, the process for preparing an acrylate monomer according to the above reaction scheme 1 will be described. In the synthesis step, naphthalene methanol and acrylic acid are mixed at an equivalent ratio of about 1: 1.1. As the solvent, toluene or cyclohexane is mixed with a mixture of naphthalene methanol and acrylic acid To synthesize the monomers.
As the catalyst, para-toluenesulfonic acid, methanesulfonic acid, or sulfuric acid can be used. As the polymerization inhibitor, hydroquinone monomethyl ether or hydroquinone may be used, and butylated hydroxytoluene, phosphorous acid or sodium hypophosphite may be used as an additive such as an antioxidant. When toluene is used as the solvent, the reaction proceeds at 98 to 105 ° C for about 8 hours. When cyclohexane is used as the solvent, the reaction proceeds at 78 to 82 ° C for about 10 hours.
After completion of the reaction, the reaction mixture is washed twice with 10% brine, and neutralized once with 15% aqueous sodium hydroxide solution. After the neutralization, washing with water was performed three times with 10% brine, and filtration was performed using a 1 탆 filter.
The filtered product is heated to 110 DEG C for toluene and 90 DEG C for cyclohexane under a vacuum, and the solvent is removed to obtain an acrylate monomer.
The acrylate monomer according to the present invention can be photocured to produce a prism film. Thus, according to another embodiment of the present invention, there is provided a composition for a prism film comprising an acrylate monomer and a photoinitiator. In this embodiment, the acrylate monomer may be included in an amount of 5 to 95 parts by weight based on 100 parts by weight of the composition for a prism film and 5 to 10 parts by weight of the photoinitiator.
The composition for a prism film comprising an acrylate monomer and a photoinitiator according to the present invention has a refractive index of 1.64 to 1.67 when measured at 25 DEG C by an Abbe refractometer.
In the case of the prism film, the higher the refractive index, the better the luminance of the display device. However, the composition for the prism film has a refractive index of about 1.60 to 1.62 on the basis of the liquid composition at present due to its physical properties. However, the liquid-phase refractive index of the composition comprising the acrylate monomer according to the invention and the photoinitiator may represent a much higher 1.64 to 1.67. This is because the naphthalene structure or the phenanthrene structure is included in the acrylate monomer of the present invention, so that an excellent refractive index can be secured.
When the refractive index of the prism film is high, the angle of the light passing through the prism film is further arranged in the vertical direction of the prism film. Accordingly, a high refractive index of the prism film leads to a higher brightness of the display device. Therefore, in the display device including the prism film manufactured using the composition for a prism film securing a high refractive index according to the present invention, A display product can be manufactured.
When high refractive index ceramic nanoparticles are added to the composition for a prism film according to the present invention, a high refractive index organic hybrid composition is obtained. The size of the nanoparticles is preferably 30 nm or less, more preferably 15 nm or less for efficiency of transparency and improvement of refractive index. As the high refractive index ceramic nanoparticles, zirconium oxide, titanium oxide, niobium oxide, and cerium oxide may be used.
The nanoparticle can be produced by a conventional method of hydrolysis of an alkoxide or a nanoparticle dispersed sol prepared through hydrothermal synthesis of an aqueous or non-aqueous system. A high refractive index organic hybrid composition can be prepared by mixing nano particles prepared in a composition for a prism film and dispersing nanoparticles in a resin composition.
The composition for a prism film and the hybrid composition for a high refractive index organic solvent according to the present invention may be photocured and formed into a prism shape to obtain a prism film. To this end, the composition for a prism film includes a photoinitiator. As the photoinitiator, any photoinitiator capable of forming radicals by irradiation with light can be used. For example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound including monophenyl, an oxime-based compound, and the like can be used as a photoinitiator.
Acetophenone-based compounds that can be used as photoinitiators include, for example, 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, Dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-phenylacetophenone, 2,2'- Benzoyloxycarbonyl), 2-benzyl-2-dimethylamino-1- (4-methoxyphenyl) Morpholinophenyl) -butan-1-one and the like.
Examples of benzophenone-based compounds that can be used as photoinitiators include benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl- Benzoyl benzoic acid, benzoyl benzoic acid methyl, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, and 4,4'- have. Examples of thioxanthone compounds that can be used as photoinitiators include thioxanthone, 2-crothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 1- [9-ethyl- ) -9H-carbazol-3-yl] -1- (O-acetyloxime), 2,4-diethylthioxanthone, 2,4- diisopropylthioxanthone, And Santon.
Examples of the benzoin compound which can be used as a photoinitiator include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
Triazine-based compounds that can be used as photoinitiators include, for example, 4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -s (Trichloromethyl) -s-triazine, 2- (p -tryl) -4,6-bis (trichloromethyl) -s Triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, bis ) - 4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthol- 4-trichloromethyl (piperonyl) -6-triazine, and 2-4-trichloromethyl (4'-methoxystyryl) -6-triazine.
Oxime compounds which can be used as photoinitiators include, for example, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol- And oxime A (Oxime A) or oxime E (Oxime E), which are oxime ester compounds, can be used in the present invention. .
Hereinafter, the present invention will be described in more detail with reference to Examples.
<Examples>
1. Preparation of composition for prism film
[Synthesis of acrylate monomers]
82 g of acrylic acid of TCI (Japan) was added under the condition of 4 g of para-toluene sulfonic acid of TCI (Japan) Co., and 158 g of naphthalene methanol was added to the reactor. 227 g of cyclohexane or toluene of TCI (Japan) Respectively. As a polymerization inhibitor, 1 g of hydroquinone monomethyl ether from TCI (Japan), 0.05 g of butylated hydroxytoluene from TCI (Japan) as an antioxidant and color stabilizer, 0.3 g of phosphorous acid of purified water (Korea) Co., TCI ) Sodium hypophosphite (0.29 g) were added in this order to the dehydration reaction at 78-84 캜 for 8 hours. At this time, a small amount of nitrogen was added to minimize coloring of the product.
The reaction product was put into a separatory funnel, and 50 g of 10% brine was added thereto. The mixture was mixed well, and the mixture was allowed to stand to separate the water and the product. When the layer completely separates, the lower layer of water is discarded. This washing process was repeated twice in total.
120 g of a 15% sodium hydroxide aqueous solution was added to the separatory funnel containing the washed product, neutralized by separating the water layer and the product layer by allowing to stand still.
40 g of 10% brine was added to the separatory funnel containing the neutralized product, and the mixture was thoroughly mixed and then separated into water and product. When the layer completely separates, the lower layer of water is discarded. This washing process was repeated three times in total.
The water-washed product was filtered with a 1 탆 filter. If the filtrate is not transparent, it is filtered several times until it becomes transparent.
The filtered product was placed in a reactor and 0.02 g of hydroquinone monomethyl ether manufactured by TCI (Japan) was added thereto, and the temperature was gradually raised under a reduced vacuum to extract the solvent. In the case of cyclohexane, the temperature was raised to 90 ° C. In the case of toluene, the temperature was elevated to 110 ° C. After 1 hour, if the solvent was no longer extracted, the reactor was cooled to obtain naphthalene methyl acrylate monomer.
[Composition for prism film]
3 g of each of Irgacure 184 and Irgacrue TPO from BASF (Germany) as photoinitiators were added to 96 g of the synthesized acrylate monomer, and the mixture was stirred at room temperature and 2,000 rpm for 20 minutes to obtain a composition for a prism film.
[evaluation]
The liquid refractive index of the composition for the synthesized prism film was measured at 25 캜 using an Abbe refractometer (NAR-1T LIQUID) manufactured by ATAGO. As a result of measurement, the refractive index was 1.64 to 1.66.
At present, the composition for a prism film exhibits a refractive index of about 1.60 to 1.62 on the basis of a liquid composition due to its own physical properties, and the composition for a prism film according to the present example exhibits a refractive index of 1.64 to 1.66, which is higher than that. Therefore, in the case of the composition for a prism film according to the present invention, the naphthalene structure or the phenanthrene structure is included in the acrylate monomer, so that the refractive index is higher than that of the conventional composition for a prism film,
2. High refractive index Abs hybrid Composition Manufacturing _ Example One
[Synthesis of Titanium Oxide Nanoparticle Dispersion Sol]
5.4 g of titanium isopropoxide (TTIP) (manufactured by Aldrich) and 61.5 g of 2-methoxyethanol (manufactured by Aldrich Co.) were placed in a 1 L three-necked flask Stir at 480 rpm. 0.68 g of distilled water and 65.96 g of 2-methoxyethanol were mixed and placed in a dropping funnel, which was then placed in a flask and dripped at a constant rate into the stirred solution. Thereafter, the mixture was stirred at room temperature for 16 hours, 0.2 g of dispersant KNJ-100 (manufactured by Polynetron) was added, and further stirred for 1 hour to prepare a dispersion of TiO 2 particles. The average size of the TiO 2 particles dispersed in the solution was 4.6 nm.
[Preparation of organic / inorganic hybrid composition]
A hybrid composition for organic TiO 2 content was prepared by adding a composition for a prism film prepared so as to vary the TiO 2 content ratio to 30 to 70 parts by weight in the prepared TiO 2 dispersion solution.
[evaluation]
In order to evaluate the refractive index of the prepared organic / inorganic hybrid composition, a coating film was formed on a slide glass by spin coating and photo-cured by an exposure machine. The refractive index of the produced organic / inorganic hybrid film was measured with an ellipsometer (Elli-SE-U, manufactured by Ellipso Technology).
Table 1 shows the results of the measurement of the refractive index by weight ratio of the composition for TiO 2 and prism film. As a result of the measurement, it was confirmed that a refractive index of 1.70 or more, which is larger than the refractive index of the composition for a prism film, was exhibited by dispersion of nano-sized TiO 2 particles, as compared with a refractive index of a composition for a prism film of 1.64 to 1.66.
2. High refractive index Abs hybrid Composition Manufacturing _ Example 2
[Synthesis of zirconium oxide nanoparticle dispersion sol]
150 g of a zirconia sol ZrO 2 (AC) of Nyacol Company, 2 [2- (2-methoxyethoxy) -ethoxy] acetic acid, MEEAA, ) Were placed in a 1 L round-bottomed flask and stirred for 30 minutes. Then, water and acetic acid were removed at 85 DEG C for 2 hours and 30 minutes using a rotary vacuum evaporator to obtain 60 g of a powder.
2,287.7 g of distilled water was redispersed in the obtained powder to prepare 2,343.7 g of a polyether acid zirconium salt. 670 g of a polyester zirconium salt was placed in a 1 L hydrothermal reactor and subjected to hydrothermal reaction in a nitrogen atmosphere. At this time, hydrothermal reaction time and temperature were hydrothermal reaction at 100 ° C. for 30 minutes, 150 ° C. for 1 hour and 30 minutes, and finally at 175 ° C. for 12 hours. The size of the dispersed ZrO 2 particles in the solution obtained after cooling the hydrothermal reactor was 22 nm on average. Subsequently, the solvent was replaced with 2-propanol to prepare a sol having dispersed zirconium oxide nanoparticles.
[Preparation of organic / inorganic hybrid composition]
To the prepared ZrO 2 dispersion solution, a composition for a prism film prepared to vary the ZrO 2 content ratio by 40 to 80 parts by weight was added to prepare an organic hybrid composition for each ZrO 2 content.
[evaluation]
In order to evaluate the refractive index of the prepared organic / inorganic hybrid composition, a coating film was formed on a slide glass by spin coating and photo-cured by an exposure machine. The refractive index of the produced organic / inorganic hybrid film was measured with an ellipsometer (Elli-SE-U, Ellipso Technology).
Table 2 shows the results of measurement of the refractive indexes by weight ratio of ZrO 2 and the composition for a prism film. As a result of measurement, it was confirmed that a refractive index of 1.67 or more, which is larger than the refractive index of a composition for a prism film, was obtained by dispersion of nano-sized ZrO 2 particles, compared with a refractive index of a composition for a prism film of 1.64 to 1.66.
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is clearly understood that the same is by way of illustration and example only and is not to be construed as limiting the scope of the invention as defined by the appended claims. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention.
Claims (6)
High refractive index organic nanocomposite; and high refractive index ceramic nanoparticles.
In the polycyclic aromatic skeleton structure,
A naphthalene structure, and a phenanthrene structure.
Wherein the high refractive index ceramic nanoparticles are at least one of titanium oxide, zirconium oxide, niobium oxide and cerium oxide.
Wherein the high refractive index ceramic nanoparticles comprise 20 to 80 parts by weight based on 100 parts by weight of the high refractive index organic hybrid composition.
Refractive index organic hybrid composition having a refractive index of 1.65 to 1.80.
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