JP5950174B2 - 光学材料用樹脂組成物、光学フィルム及び液晶表示装置 - Google Patents
光学材料用樹脂組成物、光学フィルム及び液晶表示装置 Download PDFInfo
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- JP5950174B2 JP5950174B2 JP2015539149A JP2015539149A JP5950174B2 JP 5950174 B2 JP5950174 B2 JP 5950174B2 JP 2015539149 A JP2015539149 A JP 2015539149A JP 2015539149 A JP2015539149 A JP 2015539149A JP 5950174 B2 JP5950174 B2 JP 5950174B2
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000001384 succinic acid Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- QENJZWZWAWWESF-UHFFFAOYSA-N tri-methylbenzoic acid Natural products CC1=CC(C)=C(C(O)=O)C=C1C QENJZWZWAWWESF-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133528—Polarisers
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2201/00—Constructional arrangements not provided for in groups G02F1/00 - G02F7/00
- G02F2201/50—Protective arrangements
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polarising Elements (AREA)
- Liquid Crystal (AREA)
Description
で表される化合物(B)とを含有する光学材料用樹脂組成物であり、該化合物(B)の含有量が、前記重合体(A)100質量部に対して1〜10質量部であることを特徴とする光学材料用樹脂組成物を提供するものである。
測定装置:東ソー株式会社製「HLC−8220 GPC」
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテック製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
で表されるように、ビフェノール骨格を含む。ビフェニル骨格有する事によりアクリル系樹脂の光弾性係数の絶対値を小さくするという効果が期待できる。また、末端が前記A1やA2で封止されていることにより、保存安定性等の安定性に優れた樹脂組成物となる。
<光弾性係数(CR)の測定方法>
本発明の光学フィルムの一例として延伸して得られる光学フィルムを用い、この光学フィルムを延伸方向に幅15mmで切り抜き、測定サンプルを得る。この測定サンプルを光弾性測定用引張治具(王子計測機器株式会社製)に固定し、127.3g・fから727.3g・fまで100g・f毎に測定サンプルを引っ張る際の加重を変化させ、各々の加重をかけた際の588nmにおける面内位相差変化を位相差測定装置KOBRA−WR(王子計測機器株式会社製)にて測定する。測定は23℃、相対湿度55%雰囲気下で行う
温度計、攪拌器、還流冷却器及び窒素導入管を備えた1リットルの四ツ口フラスコに、テトラメチルビフェノール型エポキシ樹脂(エポキシ当量187)299g、安息香酸195gおよび触媒としてトリフェニルホスフィン1gを加え、115℃で20時間反応させて、前記一般式(1−1)で表される化合物(B1)を得た。化合物(B1)の酸価は、0.7で、水酸基価は178であった。
温度計、攪拌器、還流冷却器及び窒素導入管を備えた1リットルの四ツ口フラスコに、テトラメチルビフェノール型エポキシ樹脂(エポキシ当量187)299g、フェノール195gおよび触媒としてトリフェニルホスフィン1gを加え、115℃で20時間反応させて、前記一般式(1−2)で表される化合物(B2)を得た。化合物(B2)の酸価は、0.7で、水酸基価は178であった。
温度計、攪拌器、還流冷却器及び窒素導入管を備えた1リットルの四ツ口フラスコに、テトラメチルビフェノール型エポキシ樹脂(エポキシ当量187)299g、パラトルイル酸217gおよび触媒としてトリフェニルホスフィン1gを加え、115℃で24時間反応させて、前記一般式(1−1)で表される化合物(B3)を得た。化合物(B3)の酸価は、0.2で、水酸基価は171であった。
温度計、攪拌器及び還流冷却器を備えた内容積1リットルの四つ口フラスコに、エチレングリコール341g、アジピン酸659gを仕込んだ。更に、テトライソプロピルチタネートをエチレングリコール及びアジピン酸の合計量に対して30ppm加えて、窒素気流下で攪拌しながら220℃まで昇温し、24時間反応させ、数平均分子量が1,100で、酸価が0.19で、水酸基価が112の比較対照用ポリエステル樹脂(b´1)を得た。
コハク酸770g、1,2−プロピレングリコール595g及び、テトライソプロピルチタネートをコハク酸と1,2−プロピレングリコールの合計量に対して60ppm使用した以外は合成例3と同様にして数平均分子量が11,000で、酸価が0.7で、水酸基価が8の比較対照用ポリエステル樹脂(b´2)を得た。
アクリル樹脂(A1)〔メチルメタアクリル酸/無水マレイン酸/スチレン=50/40/10(モル比)の共重合体、数平均分子量27,800〕100部、ポリエステル樹脂(B1)5部を、塩化メチレン270部及びメタノール30部からなる混合溶剤に加えて溶解し本発明の光学材料用樹脂組成物(ドープ液)を得た。
示差走査熱量測定計DSC822e(METTLER TOLEDO社製)を用いた。具体的には、樹脂組成物5mgを軽量アルミパンに入れ、窒素雰囲気下、25℃から150℃まで毎分10℃で昇温した(1st run)後、0℃まで一旦急冷し、再度、0℃から150℃まで毎分10℃で昇温させた(2nd run)。ガラス転移温度Tgは2nd runから得られたDSC曲線より中点法によって決定した。
位相差測定装置KOBRA−WR(王子計測機器株式会社製)を用い、588nmにおける屈折率を求めた上で、下記式に従って面内複屈折(Δn)及び面外複屈折(ΔP)を求めた。
面内複屈折(Δn)=(nx)−(ny)
面外複屈折(ΔP)=[(nx)+(ny)]/2−(nz)
〔(nx):延伸方向の屈折率、(ny):延伸方向と直交する方向の屈折率、(nz):フィルム厚み方向の屈折率〕
尚、測定は23℃、相対湿度55%雰囲気下で行った。
延伸フィルムを延伸方向と平行に幅15mmで切抜いた延伸フィルムを光弾性測定用引張治具(王子計測機器株式会社製)に固定し、127.3g・fから727.3g・fまで100g・f毎に加重を変化させたときの588nmにおける面内位相差(Re)の変化を位相差測定装置KOBRA−WR(王子計測機器株式会社製)にて測定した。測定は23℃、相対湿度55%雰囲気下で行った。面内位相差(Re)は、下記式に従って求めた。
Re=(nx−ny)×d
〔(nx):延伸方向の屈折率、(ny):延伸方向と直交する方向の屈折率、d:フィルムの厚み(μm)〕
日本電色工業株式会社製NDH−5000を用いてJIS K 7136に準拠した。
第1表〜第2表に示す配合及び延伸条件で光学材料用樹脂組成物(ドープ液)を得た以外は実施例1と同様にして光学フィルム(2)〜(8)及び比較対照用延伸フィルム(1´)〜(5´)を得た。実施例1と同様の評価を行い、その結果を第1表〜第2表に示す。
測定不能:フィルムのヘーズが大きく光学特性測定ができなかった。
アクリルフィルム(A2):メタクリル酸メチル/α‐メチルスチレン=93/7(モル比)の共重合体、数平均分子量30,000)
測定不能:フィルムのヘーズが大きく光学特性測定ができなかった。
Claims (10)
- 前記L1、L2がそれぞれフェニル基またはトリル基である請求項2記載の光学材料用樹脂組成物。
- 前記R1〜R4がそれぞれメチル基である請求項2記載の光学材料用樹脂組成物。
- 前記重合体(A)がメタクリル酸メチルの単独重合体またはメタクリル酸メチルと他の単量体との共重合体である請求項1記載の光学材料用樹脂組成物。
- 前記重合体(A)の数平均分子量が20,000〜50,000である請求項1記載の光学材料用樹脂組成物
- 請求項1〜6のいずれか1項記載の光学材料用樹脂組成物を含有することを特徴とする光学フィルム。
- 偏光板保護用である請求項7記載の光学フィルム。
- 少なくとも一軸方向の延伸物で、光弾性係数の絶対値が2(×10−12/Pa)以下である請求項7または8記載の光学フィルム。
- 請求項7〜9のいずれか1項記載の光学フィルムを有することを特徴とする液晶表示装置。
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JP2011116912A (ja) * | 2009-12-07 | 2011-06-16 | Dic Corp | セルロースエステル樹脂組成物、それを用いた光学フィルム及び液晶表示装置用偏光板 |
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