JP2009128794A - 光学フィルム、及びその製造方法 - Google Patents
光学フィルム、及びその製造方法 Download PDFInfo
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- JP2009128794A JP2009128794A JP2007306089A JP2007306089A JP2009128794A JP 2009128794 A JP2009128794 A JP 2009128794A JP 2007306089 A JP2007306089 A JP 2007306089A JP 2007306089 A JP2007306089 A JP 2007306089A JP 2009128794 A JP2009128794 A JP 2009128794A
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- Prior art keywords
- optical film
- polymer
- optical
- film
- ester
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- 239000012788 optical film Substances 0.000 title claims abstract description 118
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 229920000642 polymer Polymers 0.000 claims abstract description 130
- 239000002904 solvent Substances 0.000 claims abstract description 64
- 230000003287 optical effect Effects 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 239000010408 film Substances 0.000 claims description 66
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- 239000000758 substrate Substances 0.000 claims description 37
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- 239000000463 material Substances 0.000 claims description 31
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- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229920000307 polymer substrate Polymers 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 12
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- 238000009835 boiling Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 229920005989 resin Polymers 0.000 description 6
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
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- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 5
- XCUMMFDPFFDQEX-UHFFFAOYSA-N 2-butan-2-yl-4-[2-(3-butan-2-yl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)CC)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)CC)=C1 XCUMMFDPFFDQEX-UHFFFAOYSA-N 0.000 description 4
- IWVAMAOCYGWCIN-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)-4-methylpentan-2-yl]-2,6-dimethylphenol Chemical compound C=1C(C)=C(O)C(C)=CC=1C(C)(CC(C)C)C1=CC(C)=C(O)C(C)=C1 IWVAMAOCYGWCIN-UHFFFAOYSA-N 0.000 description 4
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- 239000003054 catalyst Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WKVWOPDUENJKAR-UHFFFAOYSA-N 2-cyclohexyl-4-[2-(3-cyclohexyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(C2CCCCC2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1CCCCC1 WKVWOPDUENJKAR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- 239000000155 melt Substances 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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Abstract
【解決手段】特定構造のポリエステルを含有する光学フィルムによって上記課題を解決し得る。前記特定構造のポリエステルは、ビスフェノールとビフェニル構造を有するジカルボン酸の重縮合物であることが好ましく、ハロゲン原子を含有しないことがさらに好ましい。かかる光学フィルムは溶剤への溶解性のみならず、耐熱性や複屈折発現性にも優れていることが好ましい。さらに、ビフェニル構造の含有量を大きくすることによって、複屈折の波長分散の大きい光学フィルムとすることができる。
【選択図】なし
Description
(A及びBは、それぞれ置換基を表し、a及びbは、それぞれ対応するA及びBの置換数(0〜4までの整数)を表す。
A及びBは、それぞれ独立して水素、ハロゲン、炭素数1〜6のアルキル基、又は置換若しくは無置換アリール基を表す。
R1及びR2は、それぞれ独立して炭素数1〜10の直鎖若しくは分枝のアルキル基、置換若しくは無置換のアリール基を表す。
R3〜R6は、それぞれ独立して、水素原子、ハロゲン原子、炭素数1〜6の直鎖若しくは分枝のアルキル基、炭素数5〜10のシクロアルキル基、又は置換若しくは無置換のアリール基を表す(ただし、R3〜R6のうち、少なくともいずれか1つは水素原子でない)。
nは2以上の整数を表す。)
前記一般式(I)で表されるエステル系ポリマーと、溶媒とを含む溶液を調製する工程、及び
該溶液を、ポリマー基材の表面に塗布して、乾燥させ、該ポリマー基材上に密着積層されたフィルムを形成する工程、
を含む光学フィルムの製造方法に関する。
前記一般式(I)で表されるエステル系ポリマーと、溶媒とを含む溶液を調製する工程、
該溶液を、基材の表面に塗布して、乾燥させ、該基材上に密着積層されたフィルムを形成する工程、及び
該フィルムを別のポリマー基材に転写する工程、
を含む光学積層体の製造方法に関する。
示差走査熱量計(セイコー(株)製 製品名「DSC−6200」)を用いて、JIS K 7121(:1987)(プラスチックの転移温度測定方法)に準じた方法により求めた。具体的には、3mgの粉末サンプルを、窒素雰囲気下(ガス流量;50ml/分)、昇温速度10℃/分で、室温から220℃まで上昇させた後、降温速度10℃/分で30℃まで降温させた(1回目の測定)。その後、昇温速度10℃/分で再度350℃まで上昇させた(2回目の測定)。2回目の測定で得られたデータを採用し、中間点をガラス転移温度とした。なお、熱量計は、標準物質(インジウム)を用いて温度補正を行った。
重量平均分子量(Mw)は、各試料を0.1%THF溶液に調製し、0.45μmメンブレンフィルターにてろ過した後、GPC本体として東ソー社製HLC−8820GPCを用い、検出器としてRI(GPC本体に内蔵)を用いて測定した。具体的には、カラム温度40℃、ポンプ流量0.35mL/分とし、データ処理は、あらかじめ分子量が既知の標準ポリスチレンの検量線を用いて、ポリスチレン換算分子量より分子量を得た。尚、使用カラムは、SuperHZM−M(径6.0mm×15cm)、SuperHZM−M(径6.0mm×15cm)及びSuperHZ2000(径6.0mm×15cm)を直列につないだものを用い、移動相としてはTHFを用いた。
王子計測機器(株)製 商品名「KOBRA−WPR」を用いて、測定波長λ(ただし、λ=450nm及び、550nmである)における正面レターデーション及び、サンプルを40度の角度で傾けた際のレターデーションから、装置付属のプログラムにより、波長λにおける厚み方向複屈折Δnxz(λ)計算した。得られた値から波長λnmにおける厚み方向レターデーションRth(λ)を算出し(ただし、Rth(λ)=Δnxz(λ)×dである)、その値から波長分散(Rth(450)/Rth(550))を求めた。
なお、膜厚dは、Sloan製 製品名「Dektak」を用い、ポリマー塗布前後のガラスの厚み差から求めた値を用いた。
日立製作所(株)製の分光光度計「U−4100」を用いて、波長400nmにおける透過率を測定した。
各溶剤を入れたサンプル瓶に、ポリマーを少しずつ加え、溶解の程度を次の基準で目視により判断した。
◎=20重量%以上溶解、
○=10〜20重量%溶解、
△=溶解するが僅かに白濁、
×=不溶
(エステル系ポリマーの合成)
攪拌装置を備えた反応容器中に、2,2−ビス(3−sec−ブチル−4−ヒドロキシフェニル)プロパン1.00g、トリエチルアミン0.65gに塩化メチレンを加え、8mlの溶液とした。この溶液を攪拌下に、温度10℃で、4,4’−ビフェニルジカルボン酸クロライド0.41g及びイソフタル酸クロライド0.30gに塩化メチレンを加えて溶解した8mlの溶液を添加した。添加終了後、温度を室温(20℃)まで上昇させ、窒素雰囲気下で4時間攪拌して反応を進行させた。重合後の溶液を20mlの塩化メチレンで希釈し、希塩酸水及びイオン交換水で洗浄した後、メタノールに投入してポリマーを析出させた。析出したポリマーを濾過し、減圧下で乾燥することで、白色のポリマー1.15gを得た。
(光学フィルムの作製)
得られたポリマー(0.1g)をシクロペンタノン(0.5g)に溶解させ、スピンコート法によってガラス上に塗布し、70℃で5分間乾燥した後、更に、110℃で30分乾燥させて光学フィルム(乾燥後の厚み=7.3μm)を作製した。
用いた試薬の量を、4,4’−ビフェニルジカルボン酸クロライド0.61g、イソフタル酸クロライド0.15gとした以外は、実施例1と同様の方法で、ポリマーの合成と光学フィルムの作製を行った。
攪拌装置を備えた反応容器中、2,2−ビス(3,5−ジメチル−4−ヒドロキシフェニル)−4−メチルペンタン0.90g、ベンジルトリエチルアンモニウムクロライド0.03gを1M水酸化ナトリウム溶液15mlに溶解させた。この溶液に、4,4’−ビフェニルジカルボン酸クロライド0.39g及びイソフタル酸クロライド0.28gを15mlのクロロホルムに溶解させた溶液を攪拌しながら一度に加え、室温で90分間攪拌した。その後、重合溶液を静置分離してポリマーを含んだクロロホルム溶液を分離し、ついで酢酸水で洗浄し、イオン交換水で洗浄した後、メタノールに投入してポリマーを析出させた。析出したポリマーを濾過し、減圧下で乾燥することで、白色のポリマー1.21g(収率91%)を得た。
得られたポリマーを用いて、実施例1と同様にして光学フィルムの作製を行った。
用いた試薬の量を、2,2−ビス(3,5−ジメチル−4−ヒドロキシフェニル)−4−メチルペンタン1.00g、ベンジルトリエチルアンモニウムクロライド0.04g、4,4’−ビフェニルジカルボン酸クロライド0.43gとし、さらに、イソフタル酸クロライド0.28gに代えてテレフタル酸クロライド0.31gとした以外は、実施例3と同様の方法で、ポリマーの合成と光学フィルムの作製を行った。
用いた試薬の量を、2,2−ビス(3,5−ジメチル−4−ヒドロキシフェニル)−4−メチルペンタン1.00g、ベンジルトリエチルアンモニウムクロライド0.04g、4,4’−ビフェニルジカルボン酸クロライド0.64g、イソフタル酸クロライド0.16gとした以外は、実施例3と同様の方法で、ポリマーの合成と光学フィルムの作製を行った。
イソフタル酸クロライド0.16gに代えて、テレフタル酸クロライド0.16gを用いた以外は実施例5と同様にして、ポリマーの合成と光学フィルムの作製を行った。
2,2−ビス(3−sec−ブチル−4−ヒドロキシフェニル)プロパン1.00gに代えて、2,2−ビス(3−シクロへキシル−4−ヒドロキシフェニル)プロパン1.00gを用い、さらに、試薬の量をトリエチルアミン0.57g、4,4’−ビフェニルジカルボン酸クロライド0.36g、イソフタル酸クロライド0.26gとした以外は、実施例1と同様の方法で、ポリマーの合成と光学フィルムの作製を行った。
2,2−ビス(3−sec−ブチル−4−ヒドロキシフェニル)プロパン1.00gに代えて、2,2−ビス(3−シクロへキシル−4−ヒドロキシフェニル)プロパン1.00gを用い、試薬の量をトリエチルアミン0.57g、4,4’−ビフェニルジカルボン酸クロライド0.53g、イソフタル酸クロライド0.13gとした以外は、実施例1と同様の方法で、ポリマーの合成と光学フィルムの作製を行った。
2,2−ビス(3,5−ジメチル−4−ヒドロキシフェニル)−4−メチルペンタン0.90gに代えて、2,2−ビス(3−メチル−4−ヒドロキシフェニル)ブタン1.00gを用い、試薬の量をベンジルトリエチルアンモニウムクロライド0.04g、4,4’−ビフェニルジカルボン酸クロライド0.48g、イソフタル酸クロライド0.34gとした以外は、実施例3と同様の方法で、ポリマーの合成と光学フィルムの作製を行った。
用いた試薬の量を、4,4’−ビフェニルジカルボン酸クロライド0.70g、イソフタル酸クロライド0.17gとした以外は実施例9と同様にして、ポリマーの合成と光学フィルムの作製を行った。
4,4’−ビフェニルジカルボン酸クロライド0.39gに代えて、テレフタル酸クロライド0.31gを用い、さらに、試薬の量をベンジルトリエチルアンモニウムクロライド0.06g、1M水酸化ナトリウム溶液25ml、イソフタル酸クロライド0.31gとした以外は、実施例3と同様の方法で、ポリマーの合成と光学フィルムの作製を行った。
試薬の量をテレフタル酸クロライド0.47g、イソフタル酸クロライド0.16gとした以外は、比較例1と同様にして、ポリマーの合成と光学フィルムの作製を行った。
R 光学フィルム
T 透明保護フィルム
S 基材
1 光学積層体
Claims (14)
- 下記一般式(I)で表される繰り返し単位を有するエステル系ポリマーを含有する光学フィルム。
(A及びBは、それぞれ置換基を表し、a及びbは、それぞれ対応するA及びBの置換数(0〜4までの整数)を表す。
A及びBは、それぞれ独立して水素、ハロゲン、炭素数1〜6のアルキル基、又は置換若しくは無置換アリール基を表す。
R1及びR2は、それぞれ独立して炭素数1〜10の直鎖若しくは分枝のアルキル基、置換若しくは無置換のアリール基を表す。
R3〜R6は、それぞれ独立して、水素原子、ハロゲン原子、炭素数1〜6の直鎖若しくは分枝のアルキル基、炭素数5〜10のシクロアルキル基、又は置換若しくは無置換のアリール基を表す(ただし、R3〜R6のうち、少なくともいずれか1つは水素原子でない)。
nは2以上の整数を表す。) - 前記一般式(I)において、R1がメチル基であり、かつ、R2が炭素数2〜4の直鎖若しくは分枝のアルキル基である、請求項1に記載の光学フィルム。
- 前記一般式(I)において、R3及びR5が炭素数1〜4の直鎖若しくは分枝のアルキル基であり、かつ、R4及びR6が水素原子又は炭素数1〜4の直鎖若しくは分枝のアルキル基である、請求項1又は2に記載の光学フィルム。
- 前記エステル系ポリマーが、化学構造中にハロゲン原子を有さない非ハロゲン化エステル系ポリマーである、請求項1から3のいずれかに記載の光学フィルム。
- 前記エステル系ポリマーが、トルエン又は酢酸エチルに可溶である、請求項1から4のいずれかに記載の光学フィルム。
- 波長400nmにおける透過率が、90%以上である、請求項1から5のいずれかに記載の光学フィルム。
- 厚みが20μm以下である、請求項1から6のいずれかに記載の光学フィルム。
- フィルム厚み方向の屈折率(nz)が、フィルム面内の屈折率の最大値(nx)よりも小さい、請求項1から7のいずれかに記載の光学フィルム。
- 前記光学フィルムの波長550nmにおける厚み方向レターデーション(Rth(550))と波長450nmにおける厚み方向レターデーション(Rth(450)の比(Rth(450)/Rth(550))が1.09以上である、請求項1から8のいずれかに記載の光学フィルム。
- 請求項1から9のいずれかに記載の光学フィルムとポリマー基材とが密着積層されてなる光学積層体。
- 請求項1から9のいずれかに記載の光学フィルム、又は請求項10に記載の光学積層体と、偏光子とを含む偏光板。
- 請求項1から9のいずれかに記載の光学フィルム、請求項10に記載の光学積層体、請求項11に記載の偏光板の少なくともいずれか1つを含む画像表示装置。
- 前記請求項1の一般式(I)で表されるエステル系ポリマーと、溶媒とを含む溶液を調製する工程、及び
該溶液を、ポリマー基材の表面に塗布して、乾燥させ、該ポリマー基材上に密着積層されたフィルムを形成する工程、
を含む光学フィルムの製造方法。 - 前記請求項1の一般式(I)で表されるエステル系ポリマーと、溶媒とを含む溶液を調製する工程、
該溶液を、基材の表面に塗布して、乾燥させ、該基材上に密着積層されたフィルムを形成する工程、及び
該光学フィルムを別のポリマー基材に転写する工程、
を含む光学積層体の製造方法。
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JP2007306089A JP4927690B2 (ja) | 2007-11-27 | 2007-11-27 | 光学フィルム、及びその製造方法 |
CN200880001155XA CN101583888B (zh) | 2007-11-27 | 2008-11-06 | 光学薄膜及其制造方法 |
KR1020097008063A KR20090080501A (ko) | 2007-11-27 | 2008-11-06 | 광학 필름 및 그 제조 방법 |
US12/516,036 US7999059B2 (en) | 2007-11-27 | 2008-11-06 | Optical film and method for production thereof |
PCT/JP2008/070226 WO2009069444A1 (ja) | 2007-11-27 | 2008-11-06 | 光学フィルム、及びその製造方法 |
TW97143745A TWI383014B (zh) | 2007-11-27 | 2008-11-12 | An optical film and a method for manufacturing the same |
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JP (1) | JP4927690B2 (ja) |
KR (1) | KR20090080501A (ja) |
CN (1) | CN101583888B (ja) |
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Cited By (4)
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JP2011104998A (ja) * | 2009-10-22 | 2011-06-02 | Nitto Denko Corp | 透明基板 |
KR20200045771A (ko) * | 2018-10-23 | 2020-05-06 | 주식회사 엘지화학 | 폴리에스테르계 수지 및 이를 포함하는 광학 부재 |
WO2022239655A1 (ja) * | 2021-05-14 | 2022-11-17 | 富士フイルム株式会社 | コーティング用樹脂組成物、ポリマー、ポリマーの製造方法、コーティング膜及びその製造方法 |
WO2022239656A1 (ja) * | 2021-05-14 | 2022-11-17 | 富士フイルム株式会社 | コーティング用樹脂組成物、ポリマー、ポリマーの製造方法、コーティング膜及びその製造方法 |
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JP5096865B2 (ja) * | 2007-09-07 | 2012-12-12 | 日東電工株式会社 | 光学フィルム、およびその製造方法 |
KR101821841B1 (ko) * | 2010-06-30 | 2018-01-24 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 다층 광학 필름 |
EP2588904A1 (en) | 2010-06-30 | 2013-05-08 | 3M Innovative Properties Company | Optical stack having birefringent layer of optically symmetrical crystallites |
JPWO2015159836A1 (ja) * | 2014-04-14 | 2017-04-13 | 富士フイルム株式会社 | 応力測定方法、応力測定用部材、および応力測定用セット |
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- 2008-11-06 CN CN200880001155XA patent/CN101583888B/zh active Active
- 2008-11-06 KR KR1020097008063A patent/KR20090080501A/ko not_active Application Discontinuation
- 2008-11-06 US US12/516,036 patent/US7999059B2/en active Active
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WO2009069444A1 (ja) | 2009-06-04 |
CN101583888B (zh) | 2011-03-16 |
US7999059B2 (en) | 2011-08-16 |
TW200936652A (en) | 2009-09-01 |
TWI383014B (zh) | 2013-01-21 |
CN101583888A (zh) | 2009-11-18 |
KR20090080501A (ko) | 2009-07-24 |
US20110064930A1 (en) | 2011-03-17 |
JP4927690B2 (ja) | 2012-05-09 |
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