WO2012165918A2 - Composition de résine pour film optique et film optique l'employant - Google Patents

Composition de résine pour film optique et film optique l'employant Download PDF

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Publication number
WO2012165918A2
WO2012165918A2 PCT/KR2012/004370 KR2012004370W WO2012165918A2 WO 2012165918 A2 WO2012165918 A2 WO 2012165918A2 KR 2012004370 W KR2012004370 W KR 2012004370W WO 2012165918 A2 WO2012165918 A2 WO 2012165918A2
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WO
WIPO (PCT)
Prior art keywords
optical film
resin composition
meth
film
acrylate
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Application number
PCT/KR2012/004370
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English (en)
Korean (ko)
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WO2012165918A3 (fr
Inventor
강병일
한창훈
이대우
서재범
김범석
최은정
김준식
이남정
김수경
성다은
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR20120051944A external-priority patent/KR101508038B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2014508304A priority Critical patent/JP2014514611A/ja
Priority to US14/009,488 priority patent/US20140046016A1/en
Priority to CN201280017567.9A priority patent/CN103459490B/zh
Publication of WO2012165918A2 publication Critical patent/WO2012165918A2/fr
Publication of WO2012165918A3 publication Critical patent/WO2012165918A3/fr

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to a resin composition for an optical film and an optical film using the same, and more particularly, to a resin composition for an optical film having a low dimensional change rate due to optical properties, heat resistance and temperature change, and an optical film using the same.
  • the most widely used polymer film for display is a triacetyl cellulose film (TAC), which is used as a polarizer protective film, and the TAC film has a low polarization degree when used for a long time in a high temperature or high humidity atmosphere. There is a problem that the film is separated or the optical properties are degraded.
  • TAC film polystyrene, acrylic such as methyl methacrylate, or polycarbonate-based polymer films having excellent heat resistance have been proposed. These polymer films have an advantage of excellent heat resistance, but when applied to a display device because birefringence occurs during film formation, there is a problem that the optical properties of the display device are lowered by the film birefringence.
  • a method of copolymerizing or blending a monomer or polymer having a positive birefringence with a monomer or a polymer having a negative birefringence as a material for a polymer film having excellent heat resistance and low retardation value has been proposed.
  • Typical examples of these methods include copolymers of benzyl methacrylate and methyl methacrylate.
  • the present invention is to solve the above problems, and provides a resin composition for an optical film and an optical film using the same as well as excellent optical properties and heat resistance, low dimensional change rate due to temperature changes.
  • the present invention includes an alkyl (meth) acrylate unit, a (meth) acrylate unit containing a benzene ring, a (meth) acrylic acid unit as an essential component, and optionally, a unit represented by the following formula (I)
  • a resin composition for an optical film comprising a copolymer further comprising a, wherein the residual monomer content in the resin composition provides a resin composition for an optical film of 2000 ppm or less.
  • X is N or O
  • R 1 and R 2 are each hydrogen, C 1 ⁇ 10 alkyl, C 3 ⁇ 20 cycloalkyl or C 3 ⁇ 20 aryl group.
  • the present invention provides an optical film made of the resin composition for an optical film and a polarizing plate including the optical film as a protective film.
  • the optical film using the resin composition for optical films according to the present invention is not only excellent in optical properties and heat resistance, but also has a low coefficient of thermal expansion and is suitable for use as a polarizing plate protective film.
  • the inventors of the present invention in order to develop a material for an optical film not only excellent in optical properties and heat resistance, but also have a low coefficient of thermal expansion, have been studied.
  • (meth) acryl containing an alkyl (meth) acrylate and a benzene ring When the residual monomer content in the resin composition copolymerized with the rate and the (meth) acrylic acid monomer was adjusted to a specific content, it was found that an optical film having excellent thermal resistance and low thermal expansion coefficient could be formed with a phase difference value close to zero.
  • the present invention has been completed.
  • the resin composition for an optical film of the present invention includes an alkyl (meth) acrylate unit, a (meth) acrylate unit containing a benzene ring, and a (meth) acrylic acid unit as essential components, and is optionally represented by the following Chemical Formula 1 It includes a copolymer containing a unit which becomes.
  • X is N or O
  • R 1 and R 2 are each hydrogen, C 1 ⁇ 10 alkyl, C 3 ⁇ 20 cycloalkyl or C 3 ⁇ 20 aryl group.
  • the alkyl (meth) acrylate means both alkyl acrylate and alkyl methacrylate, but is not limited thereto, in view of optical transparency, compatibility, processability and productivity, It is preferable that carbon number of the alkyl group of alkyl (meth) acrylate is about 1-10, It is more preferable that it is about 1-4 carbon atoms, It is most preferable that it is a methyl group or an ethyl group.
  • the (meth) acrylate containing the benzene ring is to impart a suitable retardation value to the optical film of the present invention and at the same time to impart compatibility between alkyl (meth) acrylate and (meth) acrylic acid, for example Benzyl methacrylate, benzyl acrylate, 1-phenylethyl methacrylate, 2-phenoxyethyl methacrylate, 2-phenylethyl methacrylate, 3-phenylpropyl methacrylate, 3-phenylpropyl acrylate and It may be one or more selected from the group consisting of 2-phenoxyethyl acrylate, but is not limited thereto. Among these, benzyl methacrylate, benzyl acrylate, and the like are particularly preferable, and benzyl methacrylate is most preferable.
  • the (meth) acrylic acid improves heat resistance and serves to lower the coefficient of thermal expansion by introducing a polar group, for example, acrylic acid, methacrylic acid, methylacrylic acid, methylmethacrylic acid, ethylacrylic acid, ethyl methacryl Acid, butylacrylic acid or butyl methacrylic acid, particularly methacrylic acid.
  • a polar group for example, acrylic acid, methacrylic acid, methylacrylic acid, methylmethacrylic acid, ethylacrylic acid, ethyl methacryl Acid, butylacrylic acid or butyl methacrylic acid, particularly methacrylic acid.
  • the unit represented by the formula (1) is to improve the phase difference value and the coefficient of thermal expansion more, for example, glutaric anhydride, glutaric acid imide and the like.
  • glutaric anhydride is especially preferable.
  • the coefficient of thermal expansion of the polymer can be lowered.
  • the coefficient of thermal expansion may be lowered, but birefringence may be exhibited by stretching, which may cause problems in optical properties.
  • the copolymer containing the unit represented by the formula (1) it was shown that the coefficient of thermal expansion can be effectively lowered without adversely affecting the optical properties.
  • the resin composition of the present invention is a ternary copolymer resin composed of an alkyl (meth) acrylate unit, a (meth) acrylate unit containing a benzene ring, and a (meth) acrylic acid unit
  • the alkyl (meth) in the copolymer The content ratio of the acrylate unit, the (meth) acrylate unit containing the benzene ring, and the (meth) acrylic acid unit is preferably 70 to 95: 2 to 10: 3 to 20 by weight ratio. This is because a preferable retardation value, glass transition temperature and coefficient of thermal expansion can be obtained when the content ratio of each component is within the above range.
  • the resin composition of the present invention is a quaternary copolymer resin composed of an alkyl (meth) acrylate unit, a (meth) acrylate unit containing a benzene ring, a (meth) acrylic acid unit and a unit of formula (1)
  • the content ratio of the alkyl (meth) acrylate unit, the (meth) acrylate unit including the benzene ring, the (meth) acrylic acid unit and the unit represented by the formula (1) in the copolymer is 60 to 90: 2 to 10 by weight ratio: It is preferable that it is 3-10: about 5-20. This is because a preferable retardation value, glass transition temperature and coefficient of thermal expansion can be obtained when the content ratio of each component is within the above range.
  • the resin composition of the present invention is characterized in that the content of the unreacted residual monomer in the composition is 2000 ppm or less, preferably 1500 ppm or less, and most preferably 1000 ppm or less.
  • the inventors of the present invention found that when the content of the unreacted residual monomer in the composition exceeds 2000 ppm, the glass transition temperature of the resin composition is lowered, thereby lowering the heat resistance, It has been found that contamination and / or bubbles are likely to occur, thereby degrading optical properties.
  • the extruder vacuum vent portion is easily clogged, and the residual monomers are generally in the monomer or oligomer state. Due to its low thermal stability, bubbles are generated during film formation, making product production difficult. On the other hand, such bubble generation tends to be somewhat alleviated when the film forming temperature is lowered. However, when the film is formed at a low temperature, the pressure in the extruder is increased, so that the ejection is not smooth and the productivity is sharply worsened. There is a problem that the stain is not generated enough does not appear on the film appearance.
  • the content of residual monomers should be kept below a specific content.
  • the content of the residual monomer is 1000ppm or less, there is an advantage that the generation of bubbles significantly during film film formation.
  • the resin composition of the present invention having a low content of residual monomers as described above may be prepared by mixing the monomers of each component and polymerizing them, followed by drying the product for a specific time in a specific temperature range.
  • the method for producing a resin composition of the present invention comprises the steps of: (1) copolymerizing an alkyl (meth) acrylate monomer, a (meth) acrylate monomer containing a benzene ring and a (meth) acrylic acid monomer, and (2) And drying the copolymerization reaction product at 240 ° C. to 270 ° C. for 30 minutes to 2 hours.
  • the copolymerization step may be used a copolymerization method well known in the art, for example, solution polymerization, bulk polymerization, suspension polymerization or emulsion polymerization method, and among these, it is particularly preferred to be made by a bulk polymerization method.
  • a drying step is carried out to control the residual monomer content in the resin product. At this time, it is preferable that drying temperature is about 240 degreeC-270 degreeC, and it is preferable that drying time is about 30 minutes-about 2 hours.
  • drying temperature is less than 240 °C volatilization of the residual monomer does not occur properly, it is difficult to control the content of the residual monomer, and if it exceeds 270 °C, it may cause thermal deformation of the resin composition due to high temperature.
  • the drying time is less than 30 minutes, volatilization of the residual monomer does not occur properly, and it is difficult to control the content of the residual monomer, and if it exceeds 2 hours, thermal deformation, thermal decomposition, etc. of the resin occur and serious productivity decreases. Because it can cause.
  • the discharge amount in the drying step is preferably about 3kg / hr to 6kg / hr based on a 20 liter pilot reactor. If the discharge amount is less than 3 kg / hr, the resin is deteriorated to cause a decrease in transparency, and when the discharge amount is less than 6 kg / hr, a large amount of residue is contained without sufficient drying.
  • the resin composition of the present invention prepared by the above method is about 120 ° C to 500 ° C, preferably 125 ° C to 500 ° C, more preferably 125 ° C to 200 ° C, and most preferably 130 ° C to 200 ° C It has a transition temperature.
  • the weight average molecular weight of the resin composition of the present invention is preferably 50,000 to 500,000, more preferably about 100,000 to 500,000.
  • the resin composition of the present invention has excellent optical properties with a haze value of about 0.1 to 3%, a light transmittance of 90% or more, and a yellow index of 4 or less on an injection specimen having a thickness of 3 mm.
  • the present invention relates to an optical film comprising the resin composition of the present invention.
  • the optical film may be prepared in the form of a film according to a method well known in the art, such as a solution caster method or an extrusion method. In view of economics, it is more preferable to use an extrusion method. In some cases, during the film production process, an additive such as a modifier may be further added within a range that does not impair the physical properties of the film, and a uniaxial or biaxial stretching step may be further performed.
  • the stretching step may be performed in the longitudinal direction (MD) stretching or in the transverse direction (TD) stretching, or both.
  • either stretching may be performed first and then stretched in the other direction, or both directions may be stretched simultaneously.
  • the stretching may be performed in one step or may be performed in multiple steps.
  • longitudinal stretching stretching by the speed difference between the rolls can be performed, and in the case of transverse stretching, a tenter can be used.
  • the starting angle of the tenter is usually within 10 degrees to suppress the bowing phenomenon occurring during the lateral stretching, and to control the angle of the optical axis regularly. Even when the transverse stretching is carried out in multiple stages, the anti-boeing effect can be obtained.
  • the stretching when the glass transition temperature of the resin composition is Tg, it is preferably carried out in the temperature range of (Tg-20 ° C) ⁇ (Tg + 30 ° C), the temperature range is the storage elastic modulus is lowered And thus the temperature ranges from the temperature at which the loss modulus becomes greater than the storage modulus to the temperature at which the orientation of the polymer chain is relaxed and lost.
  • the glass transition temperature of the resin composition can be measured by a differential scanning calorimeter (DSC).
  • DSC differential scanning calorimeter
  • the temperature at the time of the stretching step is more preferably the glass transition temperature of the resin composition.
  • the stretching speed is preferably in the range of 1 to 100 mm / min for the universal testing machine (Zwick Z010) and within the range of 0.1 to 2 m / min for the pilot stretching equipment.
  • the drawing ratio is preferably about 5 to 300%.
  • the optical film of the present invention prepared by the above method has a surface direction phase value (R in ) of about 0 to 10nm, preferably 0 to 5nm at a wavelength of 580nm, thickness direction retardation value (R th ) is About -5 to 10 nm, preferably -5 to 5 nm.
  • the surface direction retardation value refers to a value defined by Equation 1 below
  • the thickness direction retardation value refers to a value defined by Equation 2 below.
  • n x is the refractive index of the direction of the largest refractive index in the plane direction of the film
  • n y is the vertical direction of the n x direction in the plane direction of the film It is refractive index
  • n z is a refractive index of the thickness direction
  • d is the thickness of a film.
  • the thermal expansion coefficient of the optical film containing the resin composition of this invention is about 40-80 ppm / K, Preferably it is about 50-65 ppm / K.
  • the optical film of the present invention has a low coefficient of thermal expansion, curling may be minimized when the optical film of the present invention is used as a polarizing plate protective film.
  • the optical film of this invention is 20-200 micrometers, Preferably it is 40-120 micrometers, It is preferable that transparency is about 0.1 to 3%, and light transmittance is 90% or more. It is because it is suitable to be used as a polarizing plate protective film when the thickness, transparency, and transmittance of a film exist in the said range.
  • the content of the residual monomer in the film of the optical film of this invention is 700 ppm or less.
  • the residual monomer content in the film exceeds 700ppm, not only defects such as fish eyes are likely to occur due to the residual monomer, but also residual monomers may be migrated in the lamination process with a polarizer requiring high temperature (80 to 90 degrees). migration) to degrade the adhesiveness to the polarizer, and may cause defects such as bubbles generated between the polarizer and the optical film.
  • the present invention relates to a polarizer comprising a polarizer and an optical film according to the present invention provided on at least one surface of the polarizer as a protective film.
  • the optical film according to the present invention may be provided on both sides of the polarizer, or may be provided only on one surface.
  • a polarizer protective film well known in the art for example, TAC film, PET film, COP film, PC film, norbornene-based film, etc. Among them, in consideration of economics and the like, TAC film is particularly preferred.
  • the coefficient of thermal expansion of the optical film of the present invention is similar to that of the TAC film, when the TAC film is attached to one side of the polarizer and the optical film of the present invention is attached to the other side, the curl phenomenon caused by the difference in coefficient of thermal expansion is minimized. Can be.
  • the attachment of the polarizer and the optical film and / or protective film of the present invention after coating the adhesive on the surface of the film or polarizer using a roll coater, gravure coater, bar coater, knife coater or capillary coater, etc. ,
  • the protective film and the polarizer may be carried out by laminating by heating with a lamination roll, or laminating by pressing at room temperature.
  • adhesives used in the art for example, polyvinyl alcohol-based adhesives, polyurethane-based adhesives, acrylic adhesives and the like can be used without limitation.
  • the present invention relates to an image display device including the polarizing plate of the present invention.
  • the image display device may be, for example, a liquid crystal display (LCD), a plasma display (PDP), an electroluminescent device (LED), or the like.
  • the physical property evaluation method is as follows.
  • Glass transition temperature (Tg) Measured using a differential scanning calorimeter (DSC) of TA Instrument.
  • Retardation value (Rin, Rth): The film was stretched at the glass transition temperature, and then measured using Axoscan, Axometrics.
  • Coefficient of thermal expansion (ppm / ° C.): The film was biaxially stretched by (stretching ratio substrate), and then measured by TMA, a TA instrument, a linear coefficient of thermal expansion measurement.
  • Yellowness (Yellow Index, ASTM D 1925): The yellowness of the injection specimen with a thickness of 3 mm was measured by a colorimeter.
  • Residual monomer content 5 g of the sample was dissolved in acetone and then precipitated with methanol and measured by GC / FID (device name EQC-0248).
  • the resin was prepared into an optical film using a T-die extruder, and then the retardation value, thermal expansion coefficient and residual monomer content of the prepared optical film were measured.
  • the measurement results are shown in [Table 1] and [Table 2].
  • Example 1 Example 2
  • Example 3 Example 4
  • Example 5 Drying condition Drying temperature (°C) 270 270 240 240 Drying time (hr) 2 1.5 One 2 One Discharge amount (kg / hr) 3.2 3.8 4.4 3.2 4.4 Resin properties Tg (°C) 132 132 131 130 130 YI 4.0 3.4 2.4 2.8 1.4 Residual Monomer (ppm) 400 550 950 1050 1350 Film properties Phase difference (Rin / Rth) 0.1 / -2.1 0.3 / -1.8 0.2 / -1.0 0.2 / -1.4 0.6 / -1.0 Thermal expansion coefficient (ppm / °C) 60 60 60 60 61 Residual monomer (ppm) 200 230 330 430 520
  • Example 10 Drying condition Drying temperature (°C) 240 250 260 270 260 Drying time (hr) 0.5 One One 0.5 1.5 Discharge amount (kg / hr) 5.0 4.4 4.4 5 3.8 Resin properties Tg (°C) 129 130 130 130 130 YI 0.8 1.7 2.0 1.5 3.1 Residual Monomer (ppm) 1950 1250 1050 1450 810 Film properties Phase difference (Rin / Rth) 0.2 / 2.0 0.5 / 1.0 0.3 / -1.1 0.2 / -1.0 0.6 / -1.0 Thermal expansion coefficient (ppm / °C) 64 62 60 62 61 Residual monomer (ppm) 630 500 460 600 520 .
  • the resin was prepared into an optical film using a T-die extruder, and then the retardation value, thermal expansion coefficient and residual monomer content of the prepared optical film were measured.
  • the measurement results are shown in [Table 3].

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polarising Elements (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

La présente invention concerne un film optique et une composition pour le film optique qui comprend un copolymère comprenant un motif (méth)acrylate d'alkyle, un motif (méth)acrylate comprenant un cycle benzène, et un acide (méth)acrylique, la teneur en monomère résiduel dans la composition de résine étant inférieure à 2 000 ppm.
PCT/KR2012/004370 2011-06-01 2012-06-01 Composition de résine pour film optique et film optique l'employant WO2012165918A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2014508304A JP2014514611A (ja) 2011-06-01 2012-06-01 光学フィルム用樹脂組成物及びこれを用いた光学フィルム
US14/009,488 US20140046016A1 (en) 2011-06-01 2012-06-01 Resin composition for optical film and optical film using the same
CN201280017567.9A CN103459490B (zh) 2011-06-01 2012-06-01 光学膜用树脂组合物以及使用该树脂组合物的光学膜

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20110052907 2011-06-01
KR10-2011-0052907 2011-06-01
KR10-2012-0051944 2012-05-16
KR20120051944A KR101508038B1 (ko) 2011-06-01 2012-05-16 광학 필름용 수지 조성물 및 이를 이용한 광학 필름

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WO2012165918A3 WO2012165918A3 (fr) 2013-03-28

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015064575A1 (fr) * 2013-10-28 2015-05-07 株式会社クラレ Corps moulé en forme de plaque
CN113917589A (zh) * 2021-09-10 2022-01-11 明基材料有限公司 全周曲面偏光板

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6357613A (ja) * 1986-08-28 1988-03-12 Asahi Chem Ind Co Ltd 光学材料
EP0264508B1 (fr) * 1985-05-02 1991-09-11 Sumitomo Chemical Company, Limited Procédé de préparation de copolymères thermoplastiques stables à la chaleur
JP2000330272A (ja) * 1999-05-21 2000-11-30 Negami Kogyo Kk 感光性フィルム用感光性樹脂組成物および感光性フィルム
KR20100064971A (ko) * 2008-12-05 2010-06-15 제일모직주식회사 내열성이 우수한 메타크릴계 수지의 제조 방법 및 그에 따라 제조된 메타크릴계 수지
KR20100104518A (ko) * 2009-03-18 2010-09-29 주식회사 엘지화학 아크릴계 공중합체 수지, 이를 포함하는 광학 필름 및 액정표시 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0264508B1 (fr) * 1985-05-02 1991-09-11 Sumitomo Chemical Company, Limited Procédé de préparation de copolymères thermoplastiques stables à la chaleur
JPS6357613A (ja) * 1986-08-28 1988-03-12 Asahi Chem Ind Co Ltd 光学材料
JP2000330272A (ja) * 1999-05-21 2000-11-30 Negami Kogyo Kk 感光性フィルム用感光性樹脂組成物および感光性フィルム
KR20100064971A (ko) * 2008-12-05 2010-06-15 제일모직주식회사 내열성이 우수한 메타크릴계 수지의 제조 방법 및 그에 따라 제조된 메타크릴계 수지
KR20100104518A (ko) * 2009-03-18 2010-09-29 주식회사 엘지화학 아크릴계 공중합체 수지, 이를 포함하는 광학 필름 및 액정표시 장치

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015064575A1 (fr) * 2013-10-28 2015-05-07 株式会社クラレ Corps moulé en forme de plaque
JPWO2015064575A1 (ja) * 2013-10-28 2017-03-09 株式会社クラレ 板状成形体
CN113917589A (zh) * 2021-09-10 2022-01-11 明基材料有限公司 全周曲面偏光板

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