JP6311891B2 - 硬化膜形成組成物、配向材および位相差材 - Google Patents
硬化膜形成組成物、配向材および位相差材 Download PDFInfo
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- JP6311891B2 JP6311891B2 JP2015504389A JP2015504389A JP6311891B2 JP 6311891 B2 JP6311891 B2 JP 6311891B2 JP 2015504389 A JP2015504389 A JP 2015504389A JP 2015504389 A JP2015504389 A JP 2015504389A JP 6311891 B2 JP6311891 B2 JP 6311891B2
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- JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
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- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/32—Holograms used as optical elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
- C09D133/12—Homopolymers or copolymers of methyl methacrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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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- 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
-
- 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
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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。)。
そのため、優れた液晶配向性と光透過特性とを両立する配向材として使用することができる硬化膜、及び該硬化膜を形成するための硬化膜形成組成物の開発が必要とされている。
(A)光配向性基と、ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる一つの基とを有する化合物の一種または複数種、
(B)(B−1):ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる少なくとも一つの置換基を有するポリマー、(B−2):(A)成分と熱反応可能な置換基を有し、自己架橋可能なポリマー、または(B−3):メラミンホルムアルデヒド樹脂、から選ばれる少なくとも一種のポリマー、並びに
(C)架橋剤(但し、(B)成分が上記(B−2)であるときは、(B−2)成分と同じであっても良い。)を含有し、(A)成分は、光配向性基として下記式[1]で表される基を有する化合物を少なくとも含有する硬化膜形成組成物に関する。
A3はヒドロキシ基、メルカプト基、アミノ基、炭素原子数1乃至10のアルコキシ基、炭素原子数1乃至10のアルキルチオ基、炭素原子数1乃至10のアルキルアミノ基、フェノキシ基、フェニルチオ基、フェニルアミノ基、ビフェニルアミノ基、フェニル基またはビフェニル基を表し、
フェニレン基上及びフェニル基上の水素原子は、それぞれ独立に、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、ハロゲン原子、シアノ基またはニトロ基から選ばれる少なくとも一種の置換基で置換されていてもよい。)
本発明によれば、下記式[1]で表される基と、ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる一つの基とを有する化合物を提供することができる。
A3はヒドロキシ基、メルカプト基、アミノ基、炭素原子数1乃至10のアルコキシ基、炭素原子数1乃至10のアルキルチオ基、炭素原子数1乃至10のアルキルアミノ基、フェノキシ基、フェニルチオ基、フェニルアミノ基、ビフェニルアミノ基、フェニル基またはビフェニル基を表し、
フェニレン基上及びフェニル基上の水素原子は、それぞれ独立に、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、ハロゲン原子、シアノ基またはニトロ基から選ばれる少なくとも一種の置換基で置換されていてもよい。)
本発明によれば、下記式[2]で表される化合物を提供することができる。
A3はヒドロキシ基、メルカプト基、アミノ基、炭素原子数1乃至10のアルコキシ基、炭素原子数1乃至10のアルキルチオ基、炭素原子数1乃至10のアルキルアミノ基、フェノキシ基、フェニルチオ基、フェニルアミノ基、ビフェニルアミノ基、フェニル基またはビフェニル基を表し、
フェニレン基上及びフェニル基上の水素原子は、それぞれ独立に、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、ハロゲン原子、シアノ基またはニトロ基から選ばれる少なくとも一種の置換基で置換されていてもよく、nは2乃至20の整数を表す。)
本発明の組成物の(A)成分は、低分子配向成分である。(A)成分は、本発明の組成物から得られる本実施形態の硬化膜に光配向性を付与する成分であり、ベースとなる後述の(B)成分のポリマーに比べて低分子の光配向成分となる。
尚、本発明において、光配向性基とは、光二量化または光異性化する構造部位の官能基を言う。
(A)成分である低分子配向成分は、以上の具体例を挙げることができるが、これらに限定されるものではない。
A3はヒドロキシ基、メルカプト基、アミノ基、炭素原子数1乃至10のアルコキシ基、炭素原子数1乃至10のアルキルチオ基、炭素原子数1乃至10のアルキルアミノ基、フェノキシ基、フェニルチオ基、フェニルアミノ基、ビフェニルアミノ基、フェニル基またはビフェニル基を表し、
フェニレン基上及びフェニル基上の水素原子は、それぞれ独立に、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、ハロゲン原子、シアノ基またはニトロ基から選ばれる少なくとも一種の置換基で置換されていてもよい。)で表される光配向性基を有する化合物を含有する。
上記式[1]で表される光配向性基およびアミノ基を有する化合物の具体例としては、4−(4−アミノベンゾイル)けい皮酸メチルエステル、4−(4−アミノベンゾイル)けい皮酸エチルエステル、4−(4−アミノベンゾイル)けい皮酸ターシャリーブチルエステル、4−(3−アミノベンゾイル)けい皮酸メチルエステル、4−(3−アミノベンゾイル)けい皮酸エチルエステル、4−(3−アミノベンゾイル)けい皮酸ターシャリーブチルエステル等が挙げられる。
A3はヒドロキシ基、メルカプト基、アミノ基、炭素原子数1乃至10のアルコキシ基、炭素原子数1乃至10のアルキルチオ基、炭素原子数1乃至10のアルキルアミノ基、フェノキシ基、フェニルチオ基、フェニルアミノ基、ビフェニルアミノ基、フェニル基またはビフェニル基を表し、
フェニレン基上及びフェニル基上の水素原子は、それぞれ独立に、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、ハロゲン原子、シアノ基またはニトロ基から選ばれる少なくとも一種の置換基で置換されていてもよく、nは2乃至20の整数を表す。)
この化合物は、文献未記載の新規化合物であり、例えば、下記のスキームで示される方法で製造することができる。
金属錯体触媒としては、種々の構造のものを用いることができるが、いわゆる低原子価のパラジウム錯体又はニッケル錯体を用いることが好ましく、特に3級ホスフィンや3級ホスファイトを配位子とするゼロ価金属錯体触媒が好ましい。また、反応系中で容易にゼロ価金属錯体触媒に変換される適当な前駆体を用いることもできる。さらに、反応系中で、3級ホスフィンや3級ホスファイトを配位子として含まない金属錯体と、配位子である3級ホスフィンや3級ホスファイトとを混合し、3級ホスフィンや3級ホスファイトを配位子とする低原子価金属錯体触媒を生成させることもできる。
本発明の組成物に含有される(B)成分は、(B−1):ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる少なくとも一つの置換基を有するポリマー、(B−2):(A)成分と熱反応可能な置換基を有し、自己架橋可能なポリマー、または(B−3):メラミンホルムアルデヒド樹脂、から選ばれる少なくとも一種のポリマーである。以下、各成分について詳細に述べる。
[(B−1)成分]
(B−1)成分は、ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる少なくとも一つの置換基を有するポリマー(以下、特定(共)重合体1とも言う。)である。
このうち、アクリル重合体としてはアクリル酸エステル、メタクリル酸エステル、スチレン等の不飽和二重結合を有するモノマーを重合して得られる重合体が適用されうる。
前記アクリル酸エステル化合物としては、例えば、メチルアクリレート、エチルアクリレート、プロピルアクリレート、イソプロピルアクリレート、ブチルアクリレート、イソブチルアクリレート、t−ブチルアクリレート、ベンジルアクリレート、ナフチルアクリレート、アントリルアクリレート、アントリルメチルアクリレート、フェニルアクリレート、グリシジルアクリレート、2,2,2−トリフルオロエチルアクリレート、シクロヘキシルアクリレート、イソボルニルアクリレート、2−メトキシエチルアクリレート、メトキシトリエチレングリコールアクリレート、2−エトキシエチルアクリレート、2−アミノエチルアクリレート、テトラヒドロフルフリルアクリレート、3−メトキシブチルアクリレート、2−メチル−2−アダマンチルアクリレート、2−プロピル−2−アダマンチルアクリレート、8−メチル−8−トリシクロデシルアクリレート、及び、8−エチル−8−トリシクロデシルアクリレート等が挙げられる。
本実施の形態の硬化膜形成組成物において、(B−2)成分は(A)成分と熱反応可能な置換基を有し、自己架橋可能なポリマー(以下特定(共)重合体2ともいう)とすることもできる。
特定(共)重合体2は、より詳しくは、(A)成分との熱反応及び自己架橋反応を起こし、かつ(A)成分の昇華温度より低温で反応する架橋性置換基(以下、架橋性置換基とヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基とをまとめて特定官能基ともいう)を有するポリマーである。(A)成分と(B−2)成分との熱反応により、(A)成分が昇華するのを抑制することができる。そして、本実施の形態の硬化膜形成組成物は、硬化膜として、上述したように、光反応効率の高い配向材を形成することができる。
そのようなポリマーとしては、例えば、ポリ(3−メタクリロキシプロピルトリメトキシシラン)、3−メタクリロキシプロピルトリメトキシシランとスチレンとの共重合体、ポリ(3−アクリロキシプロピルトリメトキシシラン)、3−アクリロキシプロピルトリメトキシシランとメチルメタクリレートとの共重合体等が挙げられる。
上記モノマーの具体例は、(B−1)成分のところで記載した通りである。
このようにして得られる特定(共)重合体2は、通常、溶剤に溶解した溶液の状態である。
これらのポリマーは、単独でまたは2種以上を組み合わせて使用することができる。
本発明の組成物は、(C)成分として、架橋剤を含有する。
本発明の組成物に含有される(D)成分は、(C)成分と熱架橋可能な基とアクリル基とを有する化合物である。好ましくは、(A)成分以外の、ヒドロキシ基およびアクリル基を有する化合物である。
本発明の組成物は、上述した(A)成分、(B)成分および(C)成分に加え、上述の(D)成分を含有することができ、さらに、(E)成分として架橋触媒を含有することができる。
本発明の組成物は、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。
その他の添加剤としては、例えば、増感剤を含有することができる。増感剤は、本発明の組成物から本発明の実施形態の硬化膜を形成するに際し、その光反応を促進することにおいて有効となる。
本発明の組成物は、溶剤に溶解した溶液状態で用いられることが多い。その際に用いられる溶剤は、(A)成分、(B)成分および(C)成分、必要に応じて(D)成分、(E)成分、および/または、その他の添加剤を溶解するものであり、そのような溶解能を有する溶剤であれば、その種類および構造などは特に限定されるものでない。
本発明の組成物は、光配向性を有する熱硬化性の硬化膜形成組成物である。本発明の組成物は、上述したように、(A)成分である低分子配向成分、(B)成分である(B−1):ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる少なくとも一つの置換基を有するポリマー、(B−2):(A)成分と熱反応可能な置換基を有し、自己架橋可能なポリマー、または(B−3):メラミンホルムアルデヒド樹脂、から選ばれる少なくとも一種のポリマー、並びに、(C)成分である架橋剤を含有する。さらに、(D)成分として(A)成分以外の、ヒドロキシ基およびアクリル基を有する化合物を含有でき、(E)成分として架橋触媒を含有することができる。そして、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、さらに、溶剤を含有することができる。
本発明の組成物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3質量%乃至60質量%であり、より好ましくは5質量%乃至40質量%である。ここで、固形分とは、硬化膜形成組成物の全成分から溶剤を除いたものをいう。
本発明の組成物の溶液を基板(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、クロム等が被覆された基板、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、本発明の組成物は、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。
<光配向性基とヒドロキシ基とを有する化合物>
CIN1:4−(6−ヒドロキシヘキシルオキシ)けい皮酸メチルエステル
PEPO:ポリエステルポリオール重合体(下記構造単位を有するアジピン酸/ジエチレングリコール共重合体。分子量4,800。)
HMM:下記の構造式で表されるメラミン架橋剤
PTSA:パラトルエンスルホン酸
D−1:
MAA:メタクリル酸
MMA:メタクリル酸メチル
HEMA:2−ヒドロキシエチルメタクリレート
BMAA:N−ブトキシメチルアクリルアミド
AIBN:α、α’−アゾビスイソブチロニトリル
<溶剤>
実施例および比較例の各硬化膜形成組成物は溶剤を含有し、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(PGME)を用いた。
合成例におけるポリイミド、ポリアミック酸又はアクリルポリマーの分子量は、(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)。
装置:フーリエ変換型超伝導核磁気共鳴装置(FT−NMR)INOVA−400(Varian製)400MHz
溶媒:重水素化ジメチルスルホキシド(DMSO−d6)、重水素化クロロホルム(CDCl3)
標準物質:テトラメチルシラン(TMS)
<実施例および比較例>
(合成例1−1)CIN11の前駆体CIN11−1の合成
1H NMR (400 MHz,[D6]-DMSO):δ7.86-7.88 (d,2H), 7.73-7.75 (d,2H), 7.69-7.71 (d,2H), 7.62-7.66 (d,1H), 7.08-7.10 (d,2H), 6.65-6.69 (d,1H), 4.35-4.37 (t,1H), 4.06-4.09 (t,2H), 3.37-3.42 (q,2H), 1.73-1.77 (m,2H), 1.50 (s,9H), 1.37-1.46 (m,6H)
MAA 3.5g、MMA 7.0g、HEMA 7.0g、重合触媒としてAIBN 0.5gをPGME 53.9gに溶解し、70℃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25質量%)(P1)を得た。得られたアクリル共重合体のMnは10,300、Mwは24,600であった。
MMA 100.0g、HEMA11.1g、重合触媒としてAIBN 5.6gをPGME 450.0g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20質量%)(P2)を得た。得られたアクリル共重合体のMnは4,200、Mwは7,600であった。
BMAA100.0g、重合触媒としてAIBN 4.2gをPGME 193.5gに溶解し、90℃にて20時間反応させることによりアクリル重合体溶液(固形分濃度35質量%)(P3)を得た。得られたアクリル共重合体のMnは2,700、Mwは3,900であった。
表1に示す組成にて実施例及び比較例の各硬化膜形成組成物を調製し、それぞれについて、配向感度、パターン形成性、透過率の評価を行った。
実施例および比較例の各硬化膜形成組成物を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120秒間、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の直線偏光を垂直に照射し、配向材を形成した。基板上の配向材の上に、水平配向用重合性液晶溶液を、バーコータを用いて塗布し、次いで、70℃で60秒間ホットプレート上においてプリベークを行い、膜厚1.0μmの塗膜を形成した。この基板上の塗膜を300mJ/cm2で露光し、位相差材を作製した。作製した基板上の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、配向材が液晶配向性を示すのに必要な偏光UVの露光量を配向感度とした。評価結果は、後に表2にまとめて示す。
実施例および比較例の各硬化膜形成組成物を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120秒間、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。この硬化膜に350μmのラインアンドスペースマスクを介し313nmの直線偏光を40mJ/cm2垂直に照射した。次に、マスクを取り外し、基板を90度回転させた後、313nmの直線偏光を20mJ/cm2垂直に照射し、液晶の配向制御方向が90度異なる2種類の液晶配向領域が形成された配向材を得た。基板上の配向材の上に、水平配向用重合性液晶溶液を、バーコータを用いて塗布し、次いで、70℃で60秒間ホットプレート上においてプリベークを行い、膜厚1.0μmの塗膜を形成した。この基板上の塗膜を300mJ/cm2で露光し、異なる位相差特性を有する2種類の領域が規則的に配列されたパターン化位相差材を作製した。作製した基板上のパターン化位相差材を、偏光顕微鏡を用いて観察し、配向欠陥なく位相差パターンが形成されているものを○、配向欠陥が見られるものを×として評価した。評価結果は、後に表2にまとめて示す。
実施例および比較例の各硬化膜形成組成物を石英基板上にスピンコータを用いて塗布した後、温度110℃で120秒間ホットプレート上において加熱乾燥ベークを行い膜厚200nmの硬化膜を形成した。膜厚はFILMETRICS社製 F20を用いて測定した。この硬化膜を紫外線可視分光光度計((株)島津製作所製SHIMADZU UV−2550型番)を用いて波長400nmの光に対する透過率を測定した。
以上の評価を行った結果を、上述したように、表2に示す。
Claims (6)
- (A)光配向性基と、ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる一つの基とを有する化合物の一種または複数種、
(B)(B−1):ヒドロキシ基、カルボキシル基、アミノ基およびアルコキシシリル基からなる群から選ばれる少なくとも一つの置換基を有するポリマー、(B−2):(A)成分と熱反応可能な置換基を有し、自己架橋可能なポリマー、または(B−3):メラミンホルムアルデヒド樹脂、から選ばれる少なくとも一種のポリマー、並びに
(C)架橋剤(但し、(B)成分が上記(B−2)であるときは、(B−2)成分と同じであっても良い。)を含有し、(A)成分は、光配向性基として下記式[2]で表される化合物を少なくとも含有する硬化膜形成組成物。
A 3 はヒドロキシ基、メルカプト基、アミノ基、炭素原子数1乃至10のアルコキシ基、炭素原子数1乃至10のアルキルチオ基、炭素原子数1乃至10のアルキルアミノ基、フェノキシ基、フェニルチオ基、フェニルアミノ基、ビフェニルアミノ基、フェニル基またはビフェニル基を表し、
フェニレン基上及びフェニル基上の水素原子は、それぞれ独立に、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、ハロゲン原子、シアノ基またはニトロ基から選ばれる少なくとも一種の置換基で置換されていてもよく、nは2乃至20の整数を表す。) - 更に、(D)(A)成分以外の、ヒドロキシ基およびアクリル基を有する化合物を含有する請求項1に記載の硬化膜形成組成物。
- 更に、(E)架橋触媒を含有する請求項1又は請求項2に記載の硬化膜形成組成物。
- 請求項1乃至請求項3のいずれか1項に記載の硬化膜形成組成物を用い形成される配向材。
- 請求項1乃至請求項3のいずれか1項に記載の硬化膜形成組成物から得られる硬化膜を有する位相差材。
- 下記式[2]で表される化合物。
A3はヒドロキシ基、メルカプト基、アミノ基、炭素原子数1乃至10のアルコキシ基、炭素原子数1乃至10のアルキルチオ基、炭素原子数1乃至10のアルキルアミノ基、フェノキシ基、フェニルチオ基、フェニルアミノ基、ビフェニルアミノ基、フェニル基またはビフェニル基を表し、
フェニレン基上及びフェニル基上の水素原子は、それぞれ独立に、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、ハロゲン原子、シアノ基またはニトロ基から選ばれる少なくとも一種の置換基で置換されていてもよく、nは2乃至20の整数を表す。)
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CN104755571B (zh) | 2012-10-24 | 2018-07-13 | 日产化学工业株式会社 | 固化膜形成用组合物、取向材及相位差材 |
CN104781706B (zh) * | 2012-11-08 | 2018-01-02 | 日产化学工业株式会社 | 形成有固化膜的膜、取向材料及相位差材料 |
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