JPWO2016194846A1 - 光配向用液晶配向剤、配向材および位相差材 - Google Patents
光配向用液晶配向剤、配向材および位相差材 Download PDFInfo
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- JPWO2016194846A1 JPWO2016194846A1 JP2017521923A JP2017521923A JPWO2016194846A1 JP WO2016194846 A1 JPWO2016194846 A1 JP WO2016194846A1 JP 2017521923 A JP2017521923 A JP 2017521923A JP 2017521923 A JP2017521923 A JP 2017521923A JP WO2016194846 A1 JPWO2016194846 A1 JP WO2016194846A1
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 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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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
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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
- C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
- C08F267/06—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00 on to polymers of esters
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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
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
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- 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
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- 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
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- 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
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
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- G—PHYSICS
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B30/00—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images
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- G02B30/22—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes of the stereoscopic type
- G02B30/25—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes of the stereoscopic type using polarisation techniques
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Abstract
Description
そして、観察者がメガネを着用して3D画像を観察するディスプレイの方式の1つとしては、円偏光メガネ方式等が知られている(例えば、特許文献1を参照。)。
そして、本発明の別の目的は、良好な液晶の配向性を実現できる紫外線照射の照射量のマージン領域を拡大することができる配向材とその配向材を用いて形成された位相差材を提供することにある。
本発明の他の目的および利点は、以下の記載から明らかとなるであろう。
本発明の第1の態様において、前記式(1)において、RがOHであることが好ましい。
本発明の第1の態様において、前記(B)成分の含有量が、前記(A)成分の100質量部あたり3質量部以上100質量部以下であることが好ましい。
本発明の光配向用液晶配向剤は、光配向性を有する硬化膜を形成するためのものであり、特定の光配向性部位を有する樹脂と、けい皮酸誘導体とを含有するものである。また、本発明の光配向用液晶配向剤は、(A)成分及び(B)成分に加えて、本発明の効果を損なわない限りにおいて、その他の添加剤を含有することができる。以下、各成分の詳細を説明する。
光配向性基を有するアクリル共重合体(以下、特定共重合体ともいう)は、斯かる構造を有するアクリル共重合体であればよく、アクリル共重合体を構成する高分子の主鎖の骨格及び側鎖の種類などについて特に限定されない。
そのようなモノマーの具体例としては、アクリル酸エステル化合物、メタクリル酸エステル化合物、マレイミド化合物、アクリルアミド化合物、アクリロニトリル、マレイン酸無水物、スチレン化合物、ビニル化合物、液晶性側鎖を有するモノマー、自己架橋性基及び架橋性基を有するモノマー、ヒドロキシ基、アミド基及びアミノ基から選ばれる置換基を有するモノマー等が挙げられる。
以下、前記モノマーの具体例を挙げるが、これらに限定されるものではない。
本発明の光配向用液晶配向剤は、(B)成分として、下記式(2)で表される化合物を含有する。
本発明の光配向用液晶配向剤は、主として溶剤に溶解した溶液状態で用いられる。その際に使用する溶剤は、(A)成分及び(B)成分、所望により、後述するその他添加剤を溶解できればよく、その種類及び構造などは特に限定されるものでない。
さらに、本発明の光配向用液晶配向剤は、本発明の効果を損なわない限りにおいて、必要に応じて、増感剤、密着向上剤、シランカップリング剤、界面活性剤、レオロジー調整剤、顔料、染料、保存安定剤、消泡剤、酸化防止剤等を含有することができる。
本発明の光配向用液晶配向剤は、(A)成分である樹脂と、(B)成分であるけい皮酸誘導体とを含有する。そして、本発明の光配向用液晶配向剤は、本発明の効果を損なわない限りにおいて、その他の添加剤を含有することができる。一方、本発明の光配向用液晶配向剤は、熱架橋系を実質的に有しない。
[1]:(A)成分と(B)成分とを含有し、(B)成分の含有量が、(A)成分の100質量部あたり3質量部以上100質量部以下である光配向用液晶配向剤。
[2]:(A)成分と(B)成分とが溶剤に溶解してなる光配向用液晶配向剤。
[3]:(A)成分と(B)成分とが溶剤に溶解してなり(B)成分の含有量が、(A)成分の100質量部あたり3質量部以上100質量部以下である光配向用液晶配向剤。
[4]:(A)成分と(B)成分とともに、増感剤、密着向上剤、シランカップリング剤、界面活性剤、レオロジー調整剤、顔料、染料、保存安定剤、消泡剤及び酸化防止剤から選ばれる添加剤の少なくとも一種が溶剤に溶解してなり(B)成分の含有量が、(A)成分の100質量部あたり3質量部以上100質量部以下である光配向用液晶配向剤。
本発明の光配向用液晶配向剤における固形分の割合は、各成分が均一に溶剤に溶解している限り、特に限定されるものではないが、1質量%乃至80質量%であり、好ましくは2質量%乃至60質量%であり、より好ましくは3質量%乃至40質量%である。ここで、固形分とは、光配向用液晶配向剤の全成分から溶剤を除いたものをいう。
本発明の光配向用液晶配向剤の溶液を基板(例えば、シリコン/二酸化シリコン被覆基板、シリコンナイトライド基板、金属、例えば、アルミニウム、モリブデン、クロムなどが被覆された基板、ガラス基板、石英基板、ITO基板等)やフィルム(例えば、トリアセチルセルロース(TAC)フィルム、シクロオレフィンポリマーフィルム、ポリエチレンテレフタレートフィルム、アクリルフィルム等の樹脂フィルム)等の上に、バーコート、回転塗布、流し塗布、ロール塗布、スリット塗布、スリットに続いた回転塗布、インクジェット塗布、印刷などによって塗布して塗膜を形成し、その後、ホットプレートまたはオーブン等で加熱乾燥することにより、硬化膜を形成することができる。
そのため、本発明の光配向用液晶配向剤は、各種位相差材(位相差フィルム)や液晶表示素子等の製造に好適に用いることができる。
以下の実施例および比較例で用いられる各組成成分は、次のとおりである。
<モノマー>
MA1:4−(6−メタクリルオキシヘキシル−1−オキシ)けい皮酸
実施例及び比較例の光配向用液晶配向剤は溶剤を含有し、その溶剤として、プロピレングリコールモノメチルエーテル(PM)、シクロヘキサノン(CYH)を用いた。
重合例におけるアクリル共重合体の分子量は、(株)Shodex社製常温ゲル浸透クロマトグラフィー(GPC)装置(GPC−101)、Shodex社製カラム(KD−803、KD−805)を用い以下のようにして測定した。
なお、下記の数平均分子量(以下、Mnと称す。)及び重量平均分子量(以下、Mwと称す。)は、ポリスチレン換算値にて表した。
カラム温度:50℃
溶離液:N,N−ジメチルホルムアミド(添加剤として、臭化リチウム−水和物(LiBr・H2O)が30mmol/L、リン酸・無水結晶(o−リン酸)が30mmol/L、テトラヒドロフラン(THF)が10mL/L)
流速:1.0mL/分
検量線作成用標準サンプル:東ソー社製 TSK 標準ポリエチレンオキサイド(分子量 約900,000、150,000、100,000、30,000)、及び、ポリマーラボラトリー社製 ポリエチレングリコール(分子量 約12,000、4,000、1,000)。
MA1 15.0g、重合触媒としてα,α’−アゾビスイソブチロニトリル 0.7gを1、4−ジオキサン 141.7gに溶解し、80℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度10質量%)を得た。アクリル共重合体溶液をジエチルエーテル 1000.0gに徐々に滴下して固体を析出させ、ろ過および減圧乾燥することで残モノマーを除去し、アクリル共重合体(P1)を得た。得られたアクリル共重合体のMnは6,700、Mwは21,000であった。
MA2 4.0g、重合触媒としてα,α’−アゾビスイソブチロニトリル 0.1gを1、4−ジオキサン 36.9gに溶解し、80℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度10質量%)を得た。アクリル共重合体溶液をジエチルエーテル 500.0gに徐々に滴下して固体を析出させ、ろ過および減圧乾燥することで残モノマーを除去し、アクリル共重合体(P2)を得た。得られたアクリル共重合体のMnは9,700、Mwは24,000であった。
MA1 8.0g、MA3 1.1g、重合触媒としてα,α’−アゾビスイソブチロニトリル 0.2gを1,4−ジオキサン 99.4gに溶解し、80℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度10質量%)を得た。アクリル共重合体溶液をジエチルエーテル 1000.0gに徐々に滴下して固体を析出させ、ろ過および減圧乾燥することで残モノマーを除去し、アクリル共重合体(P3)を得た。得られたアクリル共重合体のMnは11,000、Mwは21,000であった。
MA1 6.0g、MA3 3.2g、重合触媒としてα,α’−アゾビスイソブチロニトリル 0.1gを1,4−ジオキサン 99.2gに溶解し、80℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度10質量%)を得た。アクリル共重合体溶液をジエチルエーテル 1000.0gに徐々に滴下して固体を析出させ、ろ過および減圧乾燥することで残モノマーを除去し、アクリル共重合体(P4)を得た。得られたアクリル共重合体のMnは14,000、Mwは30,000であった。
MA1 6.0g、MA4 0.2g、重合触媒としてα,α’−アゾビスイソブチロニトリル 0.2gを1,4−ジオキサン 57.2gに溶解し、80℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度10質量%)を得た。アクリル共重合体溶液をジエチルエーテル 500.0gに徐々に滴下して固体を析出させ、ろ過および減圧乾燥することで残モノマーを除去し、アクリル共重合体(P5)を得た。得られたアクリル共重合体のMnは20,000、Mwは40,000であった。
表1に示す組成にて実施例1乃至11および比較例1乃至5の各光配向用液晶配向剤を調製した。次に、各光配向用液晶配向剤を用いて硬化膜を形成し、得られた硬化膜それぞれについて、配向性の評価を行った。
実施例および比較例の各光配向用液晶配向剤をTACフィルム上にバーコータを用いて塗布した後、温度110℃で1分間、熱循環式オーブン中で加熱乾燥を行い、硬化膜を形成した。この各硬化膜に313nmの直線偏光を25mJ/cm2、50mJ/cm2、あるいは100mJ/cm2の露光量で垂直に照射し、配向材を形成した。TACフィルム上の配向材の上に、メルク株式会社製の水平配向用重合性液晶溶液RMS14−048Cを、バーコータを用いて塗布し、次いで、65℃で60秒間ホットプレート上においてプリベークを行い、塗膜を形成した。この塗膜を300mJ/cm2で露光し、位相差材を作製した。作製した位相差材を一対の偏光板で挟み込み、位相差材における位相差特性の発現状況を観察し、位相差が欠陥なく発現しているものを○、位相差が発現しているが欠陥が見られるものを△、位相差が発現していないものを×として「配向性」の欄に記載した。
Claims (6)
- (A)下記式(1)で表される構造を含む側鎖を有する樹脂と、(B)下記式(2)で表される化合物とを含有する光配向用液晶配向剤。
- 前記(A)成分の樹脂がアクリル共重合体であることを特徴とする請求項1に記載の光配向用液晶配向剤。
- 前記式(1)において、RがOHであることを特徴とする請求項1または2に記載の光配向用液晶配向剤。
- (B)成分の含有量が、(A)成分の100質量部あたり3質量部以上100質量部以下である請求項1乃至3のいずれか一項に記載の光配向用液晶配向剤。
- 請求項1乃至4のいずれか一項に記載の光配向用液晶配向剤を用いて作成された配向材。
- 請求項5に記載の配向材を用いて形成された位相差材。
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EP3299879B1 (en) | 2020-09-09 |
TW201712048A (zh) | 2017-04-01 |
KR20180014695A (ko) | 2018-02-09 |
KR102588261B1 (ko) | 2023-10-12 |
TWI696636B (zh) | 2020-06-21 |
JP6777888B2 (ja) | 2020-10-28 |
EP3299879A1 (en) | 2018-03-28 |
EP3299879A4 (en) | 2018-04-25 |
WO2016194846A1 (ja) | 2016-12-08 |
US20180119016A1 (en) | 2018-05-03 |
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