JP4610329B2 - 位相差フィルム及びそれを用いた液晶表示装置 - Google Patents
位相差フィルム及びそれを用いた液晶表示装置 Download PDFInfo
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- JP4610329B2 JP4610329B2 JP2004381588A JP2004381588A JP4610329B2 JP 4610329 B2 JP4610329 B2 JP 4610329B2 JP 2004381588 A JP2004381588 A JP 2004381588A JP 2004381588 A JP2004381588 A JP 2004381588A JP 4610329 B2 JP4610329 B2 JP 4610329B2
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- Prior art keywords
- spiro
- heptene
- bicyclo
- retardation film
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 238000007142 ring opening reaction Methods 0.000 claims description 38
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- DBJVLXKWHPAMOB-UHFFFAOYSA-N spiro[bicyclo[2.2.1]hept-2-ene-5,1'-cycloheptane] Chemical compound C1CCCC2(CC1)CC3CC2C=C3 DBJVLXKWHPAMOB-UHFFFAOYSA-N 0.000 description 1
- BMDGFYSQXPRJEW-UHFFFAOYSA-N spiro[bicyclo[2.2.1]hept-2-ene-5,1'-cyclohexane] Chemical compound C1CCC2(CC1)CC3CC2C=C3 BMDGFYSQXPRJEW-UHFFFAOYSA-N 0.000 description 1
- NEGAQZIQCFFBMI-UHFFFAOYSA-N spiro[bicyclo[2.2.1]hept-2-ene-5,1'-cyclooctane] Chemical compound C12(CCCCCCC1)C1C=CC(C2)C1 NEGAQZIQCFFBMI-UHFFFAOYSA-N 0.000 description 1
- PPGWQEFMUMFMJH-UHFFFAOYSA-N spiro[bicyclo[2.2.1]hept-2-ene-5,1'-cyclopentane] Chemical compound C1CCC2(C1)CC3CC2C=C3 PPGWQEFMUMFMJH-UHFFFAOYSA-N 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Landscapes
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Description
で表されるスピロ型ノルボルネン系開環重合体からなるフィルムを延伸してなることを特徴とするものである。
Ny=Nz>Nx (5)
で表される関係を満たすことをいう。このようなネガティブA位相差フィルムによれば、従来は困難であったTFT−LCD、STN−LCD等の視野角改善や色味改善等が可能となる。
で表されるスピロ型ノルボルネン系開環重合体からなるフィルムを延伸してなるものである。
にしたがって、対応するスピロ型ノルボルネン単量体(11)を開環重合せしめた後、得られた開環重合体(12)に対して水素添加することにより製造することができる。
にしたがってシクロペンタジエンと対応するexo−メチレン化合物のDiels−Alder反応によって製造することができる。
<ケトン型スピロノルボルネン(11’)の合成>
先ず、文献(Organic Syntheses,Vol.60,p.88)に記載の方法にしたがって2−メチレン−1−オキソ−1,2,3,4−テトラハイドロナフタレンを合成した(収率54%)。次に、2−メチレン−1−オキソ−1,2,3,4−テトラハイドロナフタレン(15.8g,0.1mol)とシクロペンタジエン(13.2g,0.2mol)との混合物を窒素雰囲気下、室温において20時間攪拌し、ロータリーエバポレーターで過剰のシクロペンタジエンを除去し、得られたオイル状物質をクーゲルロアで蒸留精製した(150℃/1mmHg)。その結果、淡黄色の液状物質として1,2−ベンゾシクロヘキセン−3−オン−4−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテン(11’)が22.0g(収率98%)得られた。得られた生成物についてNMRを用いて確認したところ、exo:endo=85:15(モル比)の混合物であることが確認された(Northcott,C.J.Valenta,Z.Can.J.Chem.1987,65,1917参照)。
窒素雰囲気下、1,2−ベンゾシクロヘキセン−3−オン−4−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテン(11’)(11.2g,0.05mol)のTHF溶液(100ml)にGrubbsII触媒(21.2mg,0.05mol%)のTHF溶液(12ml)を添加し、室温で20時間攪拌した。続いて、粘調な反応液を200mlのTHFで希釈し、4,000mlのメタノール中に投入して得られた沈殿をろ過した。次いで、真空乾燥機によって沈殿を乾燥し、1,2−ベンゾシクロヘキセン−3−オン−4−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテンの開環重合体(12’)9.5g(収率84.8%)を得た。得られた生成物についてGPCによって確認したところ、ポリスチレン換算の平均重量分子量(Mw)は430,000、Mw/Mnは2.0であった。
容量0.2リットルのオートクレーブに、1,2−ベンゾシクロヘキセン−3−オン−4−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテンの開環重合体(12’)(3.0g)、クロロベンゼン(150ml)、RuHCl(CO)(PPh3)3(150mg)を仕込み、窒素置換した。次いで、水素ガス圧10MPa、反応温度165℃の条件下で29時間加熱して水素化反応を行った後、得られた反応溶液を冷却し、水素ガスを放圧した。この反応溶液をクロロベンゼン(100ml)で希釈した後、4,000mlのアセトン中に注いで沈殿を分離回収し、得られた沈殿を乾燥して1,2−ベンゾシクロヘキセン−3−オン−4−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテンの開環重合体の水素添加物(1’)2.79g(収率93%)を得た。得られた生成物についてGPCによって確認したところ、ポリスチレン換算の平均重量分子量(Mw)は238,000、Mw/Mnは2.4であった。
<ラクトン型スピロノルボルネン(11'')の合成>
先ず、市販のα−メチレン−γ−ブチロラクトン(10g,0.1mol)とシクロペンタジエン(13.2g,0.2mol)との混合物を窒素雰囲気下、室温において20時間攪拌し、ロータリーエバポレーターで過剰のシクロペンタジエンを除去し、得られたオイル状物質をクーゲルロアで蒸留精製した(95℃/1mmHg)。その結果、無色透明な液状物質として4,5−ジヒドロフラン−2−オン−3−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテン(11'')が16.1g(収率96%)得られた。得られた生成物は数時間後に固化して白色結晶となった。
窒素雰囲気下、4,5−ジヒドロフラン−2−オン−3−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテン(11'')(10.0g,0.06mol)のクロロホルム溶液(100ml)にGrubbsII触媒(25.9mg,0.05mol%)のクロロホルム溶液(12ml)を添加し、室温で20時間攪拌した。続いて、粘調な反応液を300mlのクロロホルムで希釈し、4,000mlのメタノール中に投入して得られた沈殿をろ過した。次いで、真空乾燥機によって沈殿を乾燥し、4,5−ジヒドロフラン−2−オン−3−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテンの開環重合体(12'')10g(収率100%)を得た。得られた生成物についてGPCによって確認したところ、ポリスチレン換算の平均重量分子量(Mw)は529000、Mw/Mnは3.7であった。
容量0.2リットルのオートクレーブに、4,5−ジヒドロフラン−2−オン−3−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテンの開環重合体(12'')(3.0g)、クロロベンゼン(150ml)、RuHCl(CO)(PPh3)3(150mg)を仕込み、窒素置換した。次いで、水素ガス圧10MPa、反応温度165℃の条件下で29時間加熱して水素化反応を行った後、得られた反応溶液を冷却し、水素ガスを放圧した。この反応溶液をγ−ブチロラクトン(100ml)で希釈した後、4,000mlのアセトン中に注いで沈殿を分離回収し、得られた沈殿を乾燥して4,5−ジヒドロフラン−2−オン−3−スピロ−5‘−ビシクロ[2.2.1]−2’−ヘプテンの開環重合体の水素添加物(1'')2.85g(収率95%)を得た。得られた生成物についてGPCによって確認したところ、ポリスチレン換算の平均重量分子量(Mw)は493000、Mw/Mnは3.9であった。
<位相差フィルムの作製>
合成例1〜2で得られたスピロ型ノルボルネン系開環重合体(1’、1'')を5wt%濃度で含有するクロロホルム溶液をそれぞれ調製し、ガラス板上にキャスト法によってフィルム状に供給し、自然乾燥を24時間行った。次いで、得られたフィルムをガラス板から剥離した後、80℃の真空乾燥機でクロロホルム濃度が2.3%以下になるまで乾燥した。得られたフィルムの透明性はいずれも十分に高く、それらの膜厚は48〜54μmであった。
実施例1で得られた延伸フィルムの複屈折をレターデーション測定器(王子計測社製;「KOBRA21DH」)により測定し、得られた結果を表1及び図5に示す。なお、アッベの屈折系によって屈折率を測定した。また、前記フィルムの一軸延伸による延伸方向をX軸と定義し、且つ、X軸と直交する方向をY軸及びZ軸(Y軸とZ軸も直交)と定義し、X軸の屈折率(Nx)、Y軸の屈折率(Ny)及びZ軸の屈折率(Nz)を測定した。
Ny=Nz>Nx (5)
で表される関係を満たしていることから、いわゆるネガティブA位相差フィルムとして機能するものであることが確認された。
リタデーション:52.8nm
Nx:1.527
Ny:1.526
Nz:1.526
膜厚:99μm。
実施例1及び比較例1で得られた位相差フィルムをトリアセチルセルロースフィルムの表面上に紫外線硬化型接着剤(東亜合成社製、UVX−1942)を用いて密着せしめ、JIS K5400に記載の方法に準拠してそれらの密着性を評価したところ、いずれの位相差フィルムもトリアセチルセルロースフィルムとの密着性が非常に高いことが確認された。
Claims (5)
- 重量平均分子量が1000〜10000000であることを特徴とする請求項1に記載の位相差フィルム。
- ネガティブA位相差フィルムであることを特徴とする請求項1又は2に記載の位相差フィルム。
- 前記フィルムの一軸延伸による延伸方向をX軸と定義し、且つ、X軸と直交する方向をY軸及びZ軸と定義した場合に、X軸の屈折率(Nx)、Y軸の屈折率(Ny)及びZ軸の屈折率(Nz)が下記式(5):
Ny=Nz>Nx (5)
で表される関係を満たすことを特徴とする請求項3に記載の位相差フィルム。 - 請求項1〜4のうちのいずれか一項に記載の位相差フィルムを備えることを特徴とする液晶表示装置。
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JPH0873571A (ja) * | 1994-07-08 | 1996-03-19 | Japan Synthetic Rubber Co Ltd | 熱可塑性重合体の製造法 |
JP2000304930A (ja) * | 1999-02-17 | 2000-11-02 | Fuji Photo Film Co Ltd | 光学補償シート、楕円偏光板および液晶表示装置 |
JP2003255102A (ja) * | 2001-12-25 | 2003-09-10 | Jsr Corp | 熱可塑性ノルボルネン系樹脂系光学用フィルム |
JP2005290048A (ja) * | 2004-03-31 | 2005-10-20 | Nippon Zeon Co Ltd | 光学用樹脂材料および光学用成形体 |
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Publication number | Priority date | Publication date | Assignee | Title |
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JPH0873571A (ja) * | 1994-07-08 | 1996-03-19 | Japan Synthetic Rubber Co Ltd | 熱可塑性重合体の製造法 |
JP2000304930A (ja) * | 1999-02-17 | 2000-11-02 | Fuji Photo Film Co Ltd | 光学補償シート、楕円偏光板および液晶表示装置 |
JP2003255102A (ja) * | 2001-12-25 | 2003-09-10 | Jsr Corp | 熱可塑性ノルボルネン系樹脂系光学用フィルム |
JP2005290048A (ja) * | 2004-03-31 | 2005-10-20 | Nippon Zeon Co Ltd | 光学用樹脂材料および光学用成形体 |
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