JPWO2014017396A1 - 感光性樹脂組成物及び反射防止フィルム - Google Patents
感光性樹脂組成物及び反射防止フィルム Download PDFInfo
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- JPWO2014017396A1 JPWO2014017396A1 JP2014526894A JP2014526894A JPWO2014017396A1 JP WO2014017396 A1 JPWO2014017396 A1 JP WO2014017396A1 JP 2014526894 A JP2014526894 A JP 2014526894A JP 2014526894 A JP2014526894 A JP 2014526894A JP WO2014017396 A1 JPWO2014017396 A1 JP WO2014017396A1
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- photosensitive resin
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- antireflection film
- film
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- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- 239000002210 silicon-based material Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/02—Physical, chemical or physicochemical properties
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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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
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- 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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
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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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
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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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
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- G—PHYSICS
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
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- G02B5/0205—Diffusing elements; Afocal elements characterised by the diffusing properties
- G02B5/021—Diffusing elements; Afocal elements characterised by the diffusing properties the diffusion taking place at the element's surface, e.g. by means of surface roughening or microprismatic structures
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/40—Properties of the layers or laminate having particular optical properties
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/125—Monomers containing two or more unsaturated aliphatic radicals, e.g. trimethylolpropane triallyl ether or pentaerythritol triallyl ether
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
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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
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
-
- 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
- G02F2201/38—Anti-reflection arrangements
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/31504—Composite [nonstructural laminate]
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- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Laminated Bodies (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Liquid Crystal (AREA)
Abstract
Description
(1)分子内に少なくとも3個以上の(メタ)アクリロイル基を有する多官能(メタ)アクリレート、コロイダルシリカ、及び、表面改質剤としてアクリロイル基を有する有機変性ジメチルポリシロキサンとアクリレート変性パーフルオロポリエーテルを含有することを特徴とする反射防止フィルム用感光性樹脂組成物、
(2)感光性樹脂組成物の固形分100重量%に対してアクリロイル基を有する有機変性ジメチルポリシロキサンの含有量が0.01%〜30%であり、アクリレート変性パーフルオロポリエーテルの含有量が0.01%〜30%である、(1)に記載の感光性樹脂組成物、
(3)前記コロイダルシリカの屈折率が1.20〜1.45の範囲である、(1)又は(2)に記載の感光性樹脂組成物、
(4) 前記コロイダルシリカの含有量が感光性樹脂組成物の固形分100重量%に対して10〜90重量%である、(1)〜(3)のいずれか1項に記載の感光性樹脂組成物、
(5)(1)〜(4)のいずれか1項に記載の該感光性樹脂組成物を硬化させてなる反射防止フィルム、
(6)基板フィルム、ハードコート層及び低屈折率層を備える反射防止フィルムであって、基板フィルム上にハードコート層及び低屈折率層が順次積層されており、該低屈折率層はハードコート層よりも低い屈折率を有する、該反射防止フィルム、
(7)前記低屈折率層が(1)〜(4)のいずれか1項に記載の感光性樹脂組成物からなる、(6)に記載の反射防止フィルム、
(8)該低屈折率層の膜厚は、0.05μm以上0.15μm以下であり、且つハードコート層の膜厚が0.1μm以上30μm以下である、(6)又は(7)に記載の反射防止フィルム、
(9)前記ハードコート層が防眩性を有する、(6)〜(8)のいずれか1項に記載の反射防止フィルム、
(10)前記低屈折率層における屈折率が1.45以下である、(6)〜(9)のいずれか1項に記載の反射防止フィルム、
(11)水に対する接触角が90度以上であり、オレイン酸に対する接触角が50度以上である、(5)〜(10)のいずれか1項に記載の反射防止フィルム、
(12)(5)〜(11)のいずれか1項に記載の反射防止フィルムを含むことを特徴とする表示装置、
に関する。
また、具体的には、市場より、チバ・スペシャリティケミカルズ社製イルガキュア184(1−ヒドロキシシクロヘキシルフェニルケトン)、イルガキュア907(2−メチル−1−(4−(メチルチオ)フェニル)−2−(4−モルフォリニル)−1−プロパノン)、BASF社製ルシリンTPO(2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド)等を容易に入手出来る。また、これらは単独又は2種以上を混合して使用しても良い。
本発明の反射防止フィルムにおいては、上記感光性樹脂組成物からなる層(以下「低屈折率層」ともいう。)はハードコート層よりも屈折率が低い。
DPHA(アクリレート系感光性樹脂、日本化薬(株)製)100重量部、ニップシールSS−50B(平均粒径1.7μmのシリカ粒子、日本シリカ工業(株)製)15重量部、紫外線重合開始剤5重量部をトルエンとともに混合し、固形分濃度50重量%の防眩性ハードコート用塗布液を調製した。厚さ80μmのトリアセチルセルロースフィルムの片面に、バーコーターで該防眩性ハードコート用塗布液を塗工し、溶剤乾燥後、紫外線照射して硬化処理し、表面微細凹凸構造の防眩層を有するトリアセチルセルロースフィルムを得た。さらにジペンタエリスリトールヘキサアクリレートとペンタアクリレートとの混合物(日本化薬(株)製、KAYARAD DPHA)1.0重量部、スルーリア(ナノポーラスシリカのMIBK分散液(固形分20%、平均粒径:40〜70ナノメートル、日揮触媒化成工業(株)製)8.5重量部、表面改質剤1として固形分10%に希釈したTegoRad2600(アクリロイル基を有する有機変性ジメチルポリシロキサン、エボニック・デグサ・ジャパン(株)製)0.75重量部、表面改質剤2として固形分10%に希釈したオプツールDAC−HP(アクリレート変性パーフルオロポリエーテル、ダイキン工業(株)製)0.75重量部、イルガキュア184(チバ・スペシャリティ・ケミカルズ社製)0.075重量部、イルガキュア907(チバ・スペシャリティ・ケミカルズ社製)0.075重量部、メチルイソブチルケトン39重量部、メチルエチルケトン50重量部を混合して感光性樹脂組成物を得た。得られた感光性樹脂組成物を前記防眩性フィルム上に膜厚が約0.1μmになるように塗布し、80℃で乾燥後、紫外線照射機により硬化させ、反射防止フィルムを得た。
実施例1において、表面改質剤2をメガファックRS−75(アクリレート変性パーフルオロポリエーテル、大日本インキ(株)製)とした以外は同様に実施して、反射防止フィルムを得た。
実施例1において、表面改質剤2をメガファックRS−76E(アクリレート変性パーフルオロポリエーテル、大日本インキ(株)製)とした以外は同様に実施して、反射防止フィルムを得た。
実施例1において、表面改質剤1をBYK−3570(アクリロイル基を有する有機変性ジメチルポリシロキサン、BYK(株)製)とし、表面改質剤2をオプツールDAC−HP(アクリレート変性パーフルオロポリエーテル、ダイキン工業(株)製)とした以外は同様に実施して、反射防止フィルムを得た。
実施例1において、表面改質剤をTegoRad2600のみとした以外は同様に実施して、反射防止フィルムを得た。
実施例1において、表面改質剤2をメガファックRS−75のみとした以外は同様に実施して、反射防止フィルムを得た。
実施例1において、表面改質剤をメガファックRS−444(パーフルオロアルキルエチレンオキシド付加物、大日本インキ(株)製)のみとした以外は同様に実施して、反射防止フィルムを得た。
アクリロイルオキシプロピルトリメトキシシラン(KBM−5103、信越化学工業(株)製)100重量部とメチルエチルケトン120重量部、ジイソプロポキシアルミニウムエチルアセトアセテート(商品名:ケロープEP−12、ホープ製薬(株)製)3重量部を加え混合した後、還流冷却を行いながら撹拌を行った。イオン交換水30重量部を加え、60℃で4時間反応させたのち、室温まで冷却し、ゾル液aを得た。ゾル液a6.2重量部にKAYARAD DPHA3.3重量部、スルーリア40重量部、X22−164C(信越化学工業(株)製)0.7重量部、IRG.907を0.2重量部、MEK299.6重量部を混合して反射防止フィルム用塗布液Aを得た。実施例1と同様に製膜し反射防止フィルムを得た。
ヘーズメーター 東京電色(株)製、TC−H3DPKを使用し測定した。
紫外・可視・赤外分光光度計(株)島津製作所製UV−3150を使用し測定した。
JISK5400に従い、鉛筆引っかき試験機を用いて、上記組成の塗工フィルムの鉛筆硬度を測定した。詳しくは、測定する硬化皮膜を有するポリエステルフィルム上に、鉛筆を45度の角度で、上から750gの荷重を掛け5mm程度引っかき、5回中、4回以上傷の付かなかった鉛筆の硬さで表した。
スチールウール#0000上に250g/cm2の荷重を掛けて10往復させ、傷の状況を目視で判定した。
◎:傷が見えない
○:傷が1〜10本
×:傷が10本以上
自動接触角計協和界面科学(株)製CA−V型を使用し、純水、オレイン酸の接触角を測定。撥水・撥油性の評価として用いる。撥水=純水の接触角が高いほど、撥油=オレイン酸の接触角が高いほど好ましい。
3%NaOH水溶液をフィルム上に滴下し、30分後のフィルム表面状態を観察した。
○:変化なし
×:変色または膜が剥離
マジックインキの黒「マッキー極細(商品名:ZEBRA製)」を使用して、塗工面に文字を書き、キムワイプにて拭取りを行ない、拭き取り性を目視で判定した。
◎:10回以上拭き取り可能
○:数回〜10回未満で拭き取れる
△:1回だけ拭き取れる
×:1回も拭き取れない
Claims (12)
- 分子内に少なくとも3個以上の(メタ)アクリロイル基を有する多官能(メタ)アクリレート、コロイダルシリカ、及び、表面改質剤としてアクリロイル基を有する有機変性ジメチルポリシロキサンとアクリレート変性パーフルオロポリエーテルを含有することを特徴とする反射防止フィルム用感光性樹脂組成物。
- 感光性樹脂組成物の固形分100重量%に対してアクリロイル基を有する有機変性ジメチルポリシロキサンの含有量が0.01%〜30%であり、アクリレート変性パーフルオロポリエーテルの含有量が0.01%〜30%である、請求項1に記載の感光性樹脂組成物。
- 前記コロイダルシリカの屈折率が1.20〜1.45の範囲である、請求項1又は2に記載の感光性樹脂組成物。
- 前記コロイダルシリカの含有量が感光性樹脂組成物の固形分100重量%に対して10〜90重量%である、請求項1〜3のいずれか1項に記載の感光性樹脂組成物。
- 請求項1〜4のいずれか1項に記載の感光性樹脂組成物を硬化させてなる反射防止フィルム。
- 基板フィルム、ハードコート層及び低屈折率層を備える反射防止フィルムであって、基板フィルム上にハードコート層及び低屈折率層が順次積層されており、該低屈折率層は該ハードコート層よりも低い屈折率を有する、該反射防止フィルム。
- 前記低屈折率層が請求項1〜4のいずれか1項に記載の感光性樹脂組成物からなる、請求項6に記載の反射防止フィルム。
- 前記低屈折率層の膜厚は、0.05μm以上0.15μm以下であり、且つハードコート層の膜厚が0.1μm以上30μm以下である、請求項6又は7に記載の反射防止フィルム。
- 前記ハードコート層が防眩性を有する、請求項6〜8のいずれか1項に記載の反射防止フィルム。
- 前記低屈折率層における屈折率が1.45以下である、請求項6〜9のいずれか1項に記載の反射防止フィルム。
- 水に対する接触角が90度以上であり、オレイン酸に対する接触角が50度以上である、請求項5〜10のいずれか1項に記載の反射防止フィルム。
- 請求項5〜11のいずれか1項に記載の反射防止フィルムを含むことを特徴とする表示装置。
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US10488558B2 (en) | 2019-11-26 |
KR20150037734A (ko) | 2015-04-08 |
WO2014017396A1 (ja) | 2014-01-30 |
HK1256843A1 (zh) | 2019-10-04 |
HK1206044A1 (en) | 2015-12-31 |
EP2878607A4 (en) | 2016-02-24 |
CN108623761A (zh) | 2018-10-09 |
TWI585535B (zh) | 2017-06-01 |
US20150148474A1 (en) | 2015-05-28 |
EP2878607B1 (en) | 2018-11-28 |
JP6317256B2 (ja) | 2018-04-25 |
CN104379620A (zh) | 2015-02-25 |
TW201409178A (zh) | 2014-03-01 |
EP2878607A1 (en) | 2015-06-03 |
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