JP2004341030A - Liquid crystal aligning agent varnish, alignment layer using the varnish and liquid crystal display element having the alignment layer - Google Patents
Liquid crystal aligning agent varnish, alignment layer using the varnish and liquid crystal display element having the alignment layer Download PDFInfo
- Publication number
- JP2004341030A JP2004341030A JP2003134412A JP2003134412A JP2004341030A JP 2004341030 A JP2004341030 A JP 2004341030A JP 2003134412 A JP2003134412 A JP 2003134412A JP 2003134412 A JP2003134412 A JP 2003134412A JP 2004341030 A JP2004341030 A JP 2004341030A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- liquid crystal
- phenyl
- aligning agent
- aminophenyl
- 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.)
- Granted
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 265
- 239000002966 varnish Substances 0.000 title claims abstract description 173
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 156
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- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 239000004952 Polyamide Substances 0.000 claims abstract description 24
- 229920002647 polyamide Polymers 0.000 claims abstract description 24
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 20
- 239000004962 Polyamide-imide Substances 0.000 claims abstract description 16
- 229920002312 polyamide-imide Polymers 0.000 claims abstract description 16
- 239000004642 Polyimide Substances 0.000 claims abstract description 15
- 229920001721 polyimide Polymers 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 239000000203 mixture Substances 0.000 description 27
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- ZDEZEWYGGFXUAT-UHFFFAOYSA-N n,n'-ethylenebis-(allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboximide) Chemical compound C1=CC2CC1(CC=C)C(C1=O)C2C(=O)N1CCN(C1=O)C(=O)C2C1C1CC2(CC=C)C=C1 ZDEZEWYGGFXUAT-UHFFFAOYSA-N 0.000 description 3
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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
- 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
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Abstract
Description
【0001】
【発明の属する技術分野】
本発明は、ポリアミド酸、可溶性ポリイミド、ポリアミド、ポリアミドイミド、またはこれらの2種以上のポリマー成分を含有するワニスに、アルケニル置換ナジイミド化合物が添加された配向剤ワニス、該ワニスを基板上に塗布、焼成後、機械的または物理的な接触により表面を処理することにより形成される配向膜、該配向膜を有する、表示品位が高く、信頼性にも優れる液晶表示素子に関する。
【0002】
【従来の技術】
アルケニル置換ナジイミド化合物を構成成分の1つとする樹脂組成物が、例えば、下記特許文献1および2に開示されている。しかしながら、該文献に開示の樹脂組成物は主にカラーフィルター保護膜用樹脂組成物に関するものであり、本発明の配向膜の表示品位を改良するものとは本質的に異なっている。
また、アルケニル置換ナジイミド化合物を含有する光配向材料、光配向膜の例が、下記特許文献3に開示されている。ここに開示の光配向材料は、多官能マレイミド誘導体、およびアルケニル置換ナジイミド誘導体をもともとラビング処理などの機械的接触による表面処理を行わず、光を用いた非接触型の表面処理を行う光配向膜として用いることを目的とするものである。つまり、本発明のように機械的または物理的な接触を伴う接触型の表面配向処理、いわゆるラビング処理におけるラビング筋や傷などの発生防止のために利用するものではなく、また、ラビング処理におけるラビング筋や傷などの発生といった問題点を改善することについてはなんら記載も示唆もなく、本発明とは本質的に異なるものである。
【0003】
従来より、時計やテレビ等において液晶表示素子を用いた平面ディスプレイが広く採用されている。これらの液晶ディスプレイに用いられる液晶表示素子としては、ネマチック液晶を用いた表示素子が主流であり、90゜ツイストしたTN型液晶表示素子、通常180゜以上ツイストしたSTN型液晶表示素子、薄膜トランジスターを使用したいわゆるTN−TFT型液晶表示素子、更に昨今ではTFT型液晶表示素子の部類である、視覚特性を改良した横電界方式のイン−プレイン・スイッチング(In−Plane Switching、以下、略号「IPS」と表記する。)型液晶表示素子(非特許文献1参照)、垂直配向状態を利用したバーティカル・アラインメント(Vertical Alignment、以下、略号「VA」と表記する。)型液晶表示素子(非特許文献2参照)または応答速度が極めて速く、視野角も比較的広いことを特徴とするオプティカリ・コンペンセイティド・バイリフリンジェンス(Optically Compensate Birefringence、以下、略号「OCB」と表記する。)型液晶表示素子(非特許文献3参照)が提案されている。
【0004】
【特許文献1】
特開平9−325210号公報
【特許文献2】
特開平10−204126号公報
【特許文献3】
特開2002−265541公報
【非特許文献1】
イラスト・図解 液晶のしくみがわかる本 (株)技術評論社発行 p.159(1999)
【非特許文献2】
イラスト・図解 液晶のしくみがわかる本 (株)技術評論社発行 p.146〜150、160(1999)
【非特許文献3】
イラスト・図解 液晶のしくみがわかる本 (株)技術評論社発行 p.184〜185(1999)
【0005】
これらの液晶表示素子においては、液晶分子の長軸方向を均一に配向させることが重要である。このように液晶分子を均一に配向させる工業的に代表的な方法としては、次のようなラビング方法が知られている。即ち、基板表面に有機被膜からなる配向膜を設け、その表面を綿、ナイロン、ポリエステル等の布で一定方向にラビングし(擦る)、そのラビング方向に液晶分子を配向させる方法である。このラビング方法は、比較的容易に安定した均一配向が得られ、また生産性にも優れているため工業的に主流となっている。配向膜の材料として、例えばポリビニルアルコール、ポリオキシエチレン、ポリアミド、ポリイミド、ポリアミドイミド等のポリマーが知られているが、工業的な量産に耐え得る安定性と耐久性の観点から、ポリイミドが化学的、熱的安定性に優れているという理由で配向剤ワニスのポリマーとして最も多く用いられている。
【0006】
【発明が解決しようとする課題】
配向膜をラビングする配向処理方法は、簡便で生産性に優れた、工業的に有用な方法であるが、液晶表示素子が各分野で使用されるにつれて、液晶表示素子の高性能化により様々な問題が指摘されるようになってきた。例えば、ラビングにより生じた配向膜表面の傷が配向欠陥として見えてしまうこと、ラビングによって配向膜が削り取られ、その削りカスなどが表示欠陥になるといった問題点などが指摘されている。このようなラビングによる欠陥は、近年の大画面化に伴い、画面中にひとつでも欠陥が存在すると不良となってしまうなど、歩留まり低下に対する非常に大きな要因の一つとなっており、従来以上に厳しい耐ラビング性が要求されている。さらに近年、製造コスト等を下げるため、または軽量化のため従来のガラス基板の代わりにプラスチックフィルムを用いて液晶配向剤ワニスを200℃未満の低温で焼成する試みが行われている。しかし、特にポリイミドの前駆体であるポリアミド酸を基板上に塗布し低温で焼成した場合、ポリアミド酸の脱水閉環(イミド化)が十分に進行せず、得られるポリイミドの機械的強度不足による配向膜の傷等の問題がさらに深刻となっている。
【0007】
これらラビング方法に関わる種々の問題は、配向膜がポリマーであるためラビングによる摩擦に対応するための機械的強度が不足することに起因して、またはガラス基板等との密着性が不足することに起因して該ガラス基板から剥離してしまい、これらが改善された配向膜の開発が望まれている。機械的強度不足については、配向膜の分子構造を変えることによってある程度の改良が可能であるが、構造を変えることにより配向膜の電気的な特性や、液晶のプレチルト角も変動してしまう傾向があるため、改良するには非常に困難を伴っていた。また、ガラス基板との密着性についてはカップリング剤を用いることである程度の改良は可能であるが、カップリング剤は加水分解などを受けやすく、配向剤ワニスとしての保存安定性に問題があり、更に剥離防止のため過剰に用いると逆に液晶表示素子の性能を低下させるという点が問題となっている。
【0008】
【課題を解決するための手段】
本発明者らはこれらの問題点を解決するため鋭意検討した。その結果、アルケニル置換ナジイミドを液晶配向剤ワニスに添加すると該液晶配向剤ワニスより得られた液晶配向膜は機械的強度が強くなり、かつガラス基板との密着性が向上し、ラビングに対する耐性が高い液晶配向膜が得られると共に、更に保存安定性にも優れた液晶配向剤ワニスが得られることを見出した。本発明のアルケニル置換ナジイミド化合物誘導体は、分子骨格中にイミド結合基を含有しているため配向剤ワニスポリマー成分との相溶性も極めてよく、加水分解が発生するような部位が存在しないので、従来用いられてきたカップリング剤とは違い配向剤ワニスとしての保存安定性に問題がない。さらに剥離防止のため過剰に用いることによる液晶表示素子の表示性能等に悪影響を与えるといったことがない。また、分子内に架橋性基を有するので、配向膜のような薄膜状態で利用する場合には、比較的短時間の加熱で架橋による硬化が進行し、表面硬度が上がり、かつガラス基板との密着性も飛躍的に向上することを見出し、これらの知見に基づき、本発明を完成した。
【0009】
本発明は下記の(1)〜(9)項で構成される。
(1) ポリアミド酸、可溶性ポリイミド、ポリアミド、ポリアミドイミド、またはこれらの2種以上のポリマー成分を含有するワニスに、さらに、アルケニル置換ナジイミド化合物が添加されてなる液晶配向剤ワニス。
【0010】
(2) ポリマー成分が1種または2種以上のポリアミド酸である(1)項記載の液晶配向剤ワニス。
(3) ポリマー成分が1種または2種以上の可溶性ポリイミドである(1)項記載の液晶配向剤ワニス。
(4) ポリマー成分が1種または2種以上のポリアミドである(1)項記載の液晶配向剤ワニス。
(5) ポリマー成分が1種または2種以上のポリアミドイミドである(1)項記載の液晶配向剤ワニス。
【0011】
(6) アルケニル置換ナジイミド化合物が下記式(1)で表される化合物である前記第(1)項記載の液晶配向剤ワニス。
【0012】
【化2】
式中、R1およびR2はそれぞれ独立に、水素原子、炭素数1〜12のアルキル、炭素数3〜6のアルケニル、炭素数5〜8のシクロアルキル、アリール、ベンジルのいずれかを表し、nは1〜2の整数を表し;かつ、n=1のとき、R3は炭素数1〜12のアルキル、炭素数5〜8のシクロアルキル、炭素数6〜12のアリール、ベンジル、−{(CqH2q)Ot(CrH2rO)uCsH2s+1}(ただしq、r、sはそれぞれ独立に選ばれた2〜6の整数、tは0または1の整数及びuは1〜30の整数である)で表されるポリオキシアルキレンアルキル、−(R)a−C6H4−R4(ここで、aは0または1の整数、Rは炭素数1〜4のアルキレン、R4は水素原子若しくは炭素数1〜4のアルキルをそれぞれ表す)で表される基、−C6H4−T−C6H5{ここで、Tは−CH2−、−C(CH3)2−、−CO−、−S−若しくは−SO2―である}で表される基、またはこれらの基の芳香環に直結した1〜3個の水素原子が水酸基で置換された基であり;n=2のとき、R3は−CpH2p−(ただし、pは2〜20の整数)で表されるアルキレン、炭素数5〜8のシクロアルキレン、−{(CqH2qO)t(CrH2rO)uCsH2s}−(ここで、q、r、sはそれぞれ独立に2〜6の整数、tは0または1の整数及びuは1〜30の整数である)で表されるポリオキシアルキレン、炭素数6〜12のアリーレン、−(R)a−C6H4−R5−(ここで、aは0または1の整数、R及びR5は少なくとも一方が独立に選ばれた、炭素数1〜4のアルキレンである)で表される基、−C6H4−T―C6H4−{ただしTは−CH2−、−C(CH3)2−、−CO−、−O−、―OC6H4C(CH3)2C6H4O−、−S−、−SO2−}で表される基、またはこれらの基の芳香環に直結する1〜3個の水素原子が水酸基で置換された基である。
【0013】
(7) アルケニル置換ナジイミド化合物が液晶配向剤ワニス中のポリマー成分100重量部に対して0.01〜50重量部添加されていることを特徴とする前記第(1)項または第(6)項に記載の液晶配向剤ワニス。
【0014】
(8) 前記第(1)項〜第(7)項のいずれか1項に記載の液晶配向剤ワニスを基板上に塗布した後、焼成し、次いで、機械的または物理的な接触により表面を処理することにより形成される配向膜。
(9) 前記第(8)項記載の配向膜を含有する液晶表示素子。
【0015】
【発明の実施の形態】
本発明で用いられるアルケニル置換ナジイミド化合物について説明する。アルケニル置換ナジイミド化合物の具体例としては、例えば、
【0016】
N−メチル−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−メチル−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−メチル−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−メチル−メタリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(2−エチルヘキシル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
【0017】
N−(2−エチルヘキシル)−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−アリル−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−アリル−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−アリル−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−イソプロペニル−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−イソプロペニル−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−イソプロペニル−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−シクロヘキシル−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−シクロヘキシル−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−シクロヘキシル−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−フェニル−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
【0018】
N−フェニル−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−ベンジル−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−ベンジル−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−ベンジル−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(2’−ヒドロキシエチル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(2’−ヒドロキシエチル)−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(2’−ヒドロキシエチル)−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
【0019】
N−(2’,2’−ジメチル−3’−ヒドロキシプロピル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(2’,2’−ジメチル−3’−ヒドロキシプロピル)−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(2’,3’−ジヒドロキシプロピル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(2’,3’−ジヒドロキシプロピル)−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(3’−ヒドロキシ−1’−プロペニル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(4’−ヒドロキシ−シクロヘキシル)−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
【0020】
N−(4’−ヒドロキシフェニル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(4’−ヒドロキシフェニル)−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(4’−ヒドロキシフェニル)−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(4’−ヒドロキシフェニル)−メタリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(3’−ヒドロキシフェニル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(3’−ヒドロキシフェニル)−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−(p−ヒドロキシベンジル)−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−{2’−(2’−ヒドロキシエトキシ)エチル}−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
【0021】
N−{2’−(2’−ヒドロキシエトキシ)エチル}−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−{2’−(2’−ヒドロキシエトキシ)エチル}−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−{2’−(2’−ヒドロキシエトキシ)エチル}−メタリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−〔2’−{2’−(2”−ヒドロキシエトキシ)エトキシ}エチル〕−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−〔2’−{2’−(2”−ヒドロキシエトキシ)エトキシ}エチル〕−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−〔2’−{2’−(2”−ヒドロキシエトキシ)エトキシ}エチル〕−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−{4’−(4’−ヒドロキシフェニルイソプロピリデン)フェニル}−アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−{4’−(4’−ヒドロキシフェニルイソプロピリデン)フェニル}−アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、
N−{4’−(4’−ヒドロキシフェニルイソプロピリデン)フェニル}−メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、及びこれらのオリゴマー等が挙げられる。
【0022】
また、
N,N’−エチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−エチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−エチレン−ビス(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−トリメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ヘキサメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ヘキサメチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ドデカメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ドデカメチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−シクロヘキシレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−シクロヘキシレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
【0023】
1,2−ビス{3’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}エタン、
1,2−ビス{3’−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}エタン、
1,2−ビス{3’−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}エタン、
ビス〔2’−{3’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}エチル〕エーテル、
ビス〔2’−{3’−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}エチル〕エーテル、
1,4−ビス{3’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}ブタン、
1,4−ビス{3’−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}ブタン、
【0024】
N,N’−p−フェニレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−フェニレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−フェニレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−フェニレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−{(1−メチル)−2,4−フェニレン}−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−キシリレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−キシリレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
【0025】
2,2−ビス〔4’−{4’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
2,2−ビス〔4’−{4’−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
2,2−ビス〔4’−{4’−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
ビス{4−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
【0026】
ビス{4−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(メタリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}エーテル、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}エーテル、
ビス{4−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}エーテル、
ビス{4−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}スルホン、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}スルホン、
【0027】
ビス{4−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}スルホン、
1,6−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−3−ヒドロキシ−ヘキサン、
1,12−ビス(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−3,6−ジヒドロキシ−ドデカン、
1,3−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−5−ヒドロキシ−シクロヘキサン、
1,5−ビス{3’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)プロポキシ}−3−ヒドロキシ−ペンタン、
1,4−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−2−ヒドロキシ−ベンゼン、
【0028】
1,4−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−2,5−ジヒドロキシ−ベンゼン、
N,N’−p−(2−ヒドロキシ)キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−(2−ヒドロキシ)キシリレン−ビス(アリルメチルシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−(2−ヒドロキシ)キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−(2−ヒドロキシ)キシリレン−ビス(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−(2,3−ジヒドロキシ)キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
【0029】
2,2−ビス〔4’−{4’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−2’−ヒドロキシ−フェノキシ}フェニル〕プロパン、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−2−ヒドロキシ−フェニル}メタン、
ビス{3−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−4−ヒドロキシ−フェニル}エーテル、
ビス{3−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)−5−ヒドロキシ−フェニル}スルホン、
1,1,1−トリ{4’−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)}フェノキシメチルプロパン、
N,N’,N”−トリ(エチレンメタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)イソシアヌレート、
及びこれらのオリゴマー等が挙げられる。
【0030】
さらに、非対称なアルキレン・フェニレン基を含む次のようなものでも良い。
【0031】
【化3】
【0032】
また、これらのアルケニル置換ナジイミド化合物は、単独で用いてもよいし、これらの混合物として用いてもよい。
【0033】
上記のアルケニル置換ナジイミド化合物として、好ましいものは
N,N’−エチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−エチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−エチレン−ビス(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−トリメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ヘキサメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ヘキサメチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ドデカメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ドデカメチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−シクロヘキシレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−シクロヘキシレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
【0034】
N,N’−p−フェニレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−フェニレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−フェニレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−フェニレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−{(1−メチル)−2,4−フェニレン}−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−キシリレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−キシリレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
2,2−ビス〔4’−{4’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
2,2−ビス〔4’−{4’−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
2,2−ビス〔4’−{4’−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
ビス{4−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
【0035】
ビス{4−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(メタリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}エーテル、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}エーテル、
ビス{4−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}エーテル、
ビス{4−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}スルホン、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}スルホン、
【0036】
ビス{4−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}スルホン、
アルケニル置換ナジイミド化合物として、更に好ましいものは、
N,N’−エチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−エチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−エチレン−ビス(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−トリメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ヘキサメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ヘキサメチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ドデカメチレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−ドデカメチレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−シクロヘキシレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−シクロヘキシレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
【0037】
N,N’−p−フェニレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−フェニレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−フェニレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−フェニレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−{(1−メチル)−2,4−フェニレン}−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−p−キシリレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−キシリレン−ビス(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
N,N’−m−キシリレン−ビス(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)、
【0038】
2,2−ビス〔4’−{4’−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
2,2−ビス〔4’−{4’−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
2,2−ビス〔4’−{4’−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェノキシ}フェニル〕プロパン、
ビス{4−(アリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(アリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
【0039】
ビス{4−(メタリルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
ビス{4−(メタリルメチルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド)フェニル}メタン、
等が挙げられる。
【0040】
本発明の液晶配向剤ワニスは、ポリアミド酸、可溶性ポリイミド、ポリアミド、ポリアミドイミドまたはこれらの2種以上の混合物などからなるポリマー成分を溶剤に溶解した状態のワニス組成物に、さらにアルケニル置換ナジイミド化合物が添加されたものであり、該アルケニル置換ナジイミド化合物の添加量は、ほぼポリマー成分100重量部に対して0.01〜50.0重量部であり、好ましくは0.1〜30.0重量部、より好ましくは0.3〜10.0重量部である。本発明のアルケニル置換ナジイミド化合物の添加量がこれらの範囲内であれば、耐ラビング性、液晶配向性、および表示品位との間のバランスが維持された液晶配向剤ワニスとすることができる。
【0041】
本発明で定義されるラビングによる液晶配向膜の削れ防止効果とは、液晶配向膜の基板からの剥離防止効果(密着性の向上効果)と液晶配向膜の表面硬度を上げることによるラビング削れ傷の低減効果をさす。
【0042】
本発明者らの実験によれば、液晶配向膜のラビングによる削れ傷は基板と液晶配向膜の密着性および表面硬度に関連性がある。つまり、液晶配向膜と基板の密着性が強くなればラビングによる液晶配向膜の剥離が防止でき、また表面硬度が高くなればラビング傷の発生が低減される。このような液晶配向膜の剥離防止効果とラビング傷の低減効果が互いに影響しあう相乗的効果により、ラビングによる液晶配向膜の削れを防止できる。
【0043】
本発明者らは液晶配向膜の表面硬度(押し込み硬度)に着目し鋭意検討した結果、下記の式から求められるアルケニル置換ナジイミドを添加した液晶配向剤ワニスより形成された液晶配向膜の表面硬度が、アルケニル置換ナジイミドを添加しない液晶配向剤ワニスより形成された液晶配向膜の表面硬度と比べ101%以上の変化率になり、耐ラビング性が高い液晶配向膜となっていることを見出した。
【0044】
本発明で用いる表面硬度は下記の式により定義される押し込み硬度(H)を指す。
押し込み硬度(H)=kF/h2
(ただし、F:硬さ評価時の押し込み荷重(gf:グラム重)、h:試験面に試験圧子を押し込んだときに形成されるくぼみの深さ(μm)、k:圧子の形状により決まる定数。)
kは、圧子形状により決まる定数であるが、本発明の表面硬度測定に用いる圧子の形状は三角錘であり、その稜間角には65°、100°、115°がある。本発明では、稜間角115°の圧子を用いており、この場合、k=37.926である。
【0045】
表面硬度測定に使用する液晶配向膜の膜厚には特に制限はないが、膜厚が薄い場合、測定値に液晶配向膜の下地の影響が現れる。したがって、液晶配向膜本来の表面硬度を測定するための膜厚の好適な範囲としては1μm以上がよい。また、液晶配向膜の本来の表面硬度測定のためには、圧子の押し込み深さの好適な範囲は、液晶配向膜の膜厚の1/3以下、好ましくは1/5以下、より好ましくは1/10以下である。
【0046】
配向膜にラビングによる削れ傷を生じさせないようにするためには基板との密着性と表面硬度の両方の視点からみると、アルケニル置換ナジイミド化合物の添加量は、ポリマー成分100重量部に対して0.3〜10.0重量部の範囲が特に有用である。
【0047】
本発明の液晶配向剤ワニスは、アルケニル置換ナジイミドとポリマー成分を、溶剤に溶解した状態のワニス組成物である。該ワニス中のポリマー成分は、ランダム共重合体またはブロック共重合体等のコポリマーであっても良く、複数種のポリマー成分を併用して使用しても良い。そして、該ポリマーの主成分としては、テトラカルボン酸二無水物とジアミンを反応させて得られるポリアミド酸、このポリアミド酸を脱水反応等によって脱水、閉環して得られる可溶性ポリイミド、ジカルボン酸若しくはその誘導体、例えばジカルボン酸ジハライドとジアミンとを反応させて得られるポリアミド、該ポリアミドのアミド結合(CONH)の水素原子が他の基で置換されたもの、ジアミンとテトラカルボン酸二無水物およびジカルボン酸若しくはその誘導体を反応させて得られるポリアミド、またはジアミンとトリメリット酸若しくはその誘導体を反応させて得られるポリアミドイミド等が挙げられ、好ましく用いられる。
【0048】
上記のテトラカルボン酸二無水物の選択条件はジアミンと反応してポリアミド酸を生成することが可能であるだけであり、また、ジカルボン酸またはジカルボン酸ジハライドの選択条件はジアミンと反応してポリアミドを生成することが可能であるだけであり、それぞれ他には何の制限もない。ジアミンについても同様に、テトラカルボン酸二無水物と反応してポリアミド酸を生成すること、およびジカルボン酸若しくはその誘導体と反応してポリアミドを生成することが可能であるだけが選択条件であり、他には何の制限もない。また、これらのテトラカルボン酸二無水物、ジカルボン酸若しくはその誘導体およびジアミンのそれぞれ2種以上を併用することについても、全く制限されない。
【0049】
ポリアミド酸またはポリアミドの原料としての酸類やジアミンのうち、テトラカルボン酸二無水物およびジアミンの具体例は、例えばWO 98/31725A1、WO 99/33902A1、WO 99/33923A1、WO 99/34252A1およびWO 01/00732A1等の公報に、それらの一部が記載されており、それらの化合物から任意に選択して用いることができる。また、ジカルボン酸の具体例は、例えばWO 01/14457A1にその一部が記載されており、それらの化合物およびそれらの化合物の酸ジハライドから任意に選択して用いることができる。
【0050】
具体的には次のようなものが挙げられる。
【0051】
ピロメリット酸二無水物、
3,3’,4,4’−ジフェニルテトラカルボン酸二無水物、
3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物、
ナフタレン酸二無水物(2,3,6,7−ナフタレン酸無水物等)、
3,3’,4,4’−ビフェニルスルホンテトラカルボン酸二無水物、
3,3’,4,4’−ビフェニルエ−テルテトラカルボン酸二無水物、
3,3’,4,4’−ジメチルジフェニルシランテトラカルボン酸二無水物、
4,4’−ビス(3,4−ジカルボキシフェノキシ)ジフェニルスルフィド二無水物、
4,4’−ビス(3,4−ジカルボキシフェノキシ)ジフェニルスルホン二無水物、
4,4’−ビス(3,4−ジカルボキシフェノキシ)ジフェニルプロパン二無水物、
3,3’,4,4’−パ−フルオロピリデンジフタル酸二無水物、
3,3’,4,4’−ビフェニルテトラカルボン酸二無水物、
ビス(フタル酸)フェニルスルフィンオキサイド二無水物、
p−フェニレン−ビス(トリフェニルフタル酸)二無水物、
m−フェニレン−ビス(トリフェニルフタル酸)二無水物、
ビス(トリフェニルフタル酸)−4,4’−ジフェニルエ−テル二無水物、
ビス(トリフェニルフタル酸)−4,4’−ジフェニルメタン二無水物等、
【0052】
シクロブタンテトラカルボン酸二無水物、
シクロペンタンテトラカルボン酸二無水物、
ビシクロ[2.2.2]−オクト−7−エン−2,3,5,6−テトラカルボン酸二無水物、
シクロヘキサン−1,2,5,6−テトラカルボン酸二無水物、
3,3’−ビシクロヘキシル−1,1’,2,2’−テトラカルボン酸二無水物、
2,3,5−トリカルボキシシクロペンチル酢酸二無水物、
5−(2,5−ジオキソテトラヒドロフラル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸二無水物、
1,3,3a,4,5,9b−ヘキサヒドロ−5−テトラヒドロ−2,5−ジオキソ−3−フラニル)−ナフト[1,2,−c]−フラン−1,3−ジオン、3,5,6−トリカルボキシノルボルナン−2−酢酸二無水物、
2,3,4,5−テトラヒドロフランテトラカルボン酸二無水物、
若しくはこれらにメチル、エチル基などの低級アルキルを一部置換したテトラカルボン酸二無水物、
【0053】
エチレンテトラカルボン酸二無水物、
ブタンテトラカルボン酸二無水物、
ペンタンテトラカルボン酸二無水物、
ヘキサンテトラカルボン酸二無水物、
ヘプタンテトラカルボン酸二無水物等。
【0054】
本発明に係わるテトラカルボン酸二無水物はこれらに限定されることなく、本発明の目的が達成される範囲内で他にも種々の酸二無水物を用いてもよい。また、これらのテトラカルボン酸二無水物は単独で、または2種以上を組み合わせて用いることもできる。
【0055】
本発明のポリアミドを与えるジカルボン酸若しくはその誘導体の具体例として以下のものを挙げることができる。
ジカルボン酸の形態で、マロン酸、蓚酸、ジメチルマロン酸、コハク酸、フマル酸、グルタル酸、アジピン酸、ムコン酸、2−メチルアジピン酸、トリメチルアジピン酸、ピメリン酸、2,2−ジメチルグルタル酸、3,3−ジエチルコハク酸、アゼライイン酸、セバシン酸およびスベリン酸等、
【0056】
1,1−シクロプロパンジカルボン酸、
1,2−シクロプロパンジカルボン酸、
1,1−シクロブタンジカルボン酸、
1,2−シクロブタンジカルボン酸、
1,3−シクロブタンジカルボン酸、
3,4−ジフェニル−1,2−シクロブタンジカルボン酸、
2,4−ジフェニル−1,3−シクロブタンジカルボン酸、
3,4−ビス(2−ヒドロキシフェニル)−1,2−シクロブタンジカルボン酸、
2,4−ビス(2−ヒドロキシフェニル)−1,3−シクロブタンジカルボン酸、
【0057】
1−シクロブテン−1,2−ジカルボン酸、
1−シクロブテン−3,4−ジカルボン酸、
1,1−シクロペンタンジカルボン酸、
1,2−シクロペンタンジカルボン酸、
1,3−シクロペンタンジカルボン酸、
1,1−シクロヘキサンジカルボン酸、
1,2−シクロヘキサンジカルボン酸、
1,3−シクロヘキサンジカルボン酸、
1,4−シクロヘキサンジカルボン酸、
1,4−(2−ノルボルネン)ジカルボン酸、
【0058】
ノルボルネン−2,3−ジカルボン酸、
ビシクロ[2.2.2]オクタン−1,4−ジカルボン酸、
ビシクロ[2.2.2]オクタン−2,3−ジカルボン酸、
2,5−ジオキソ−1,4−ビシクロ[2.2.2]オクタンジカルボン酸、
1,3−アダマンタンジカルボン酸、
4,8−ジオキソ−1,3−アダマンタンジカルボン酸、
2,6−スピロ[3.3]ヘプタンジカルボン酸、
1,3−アダマンタン二酢酸、
カンファー酸等。
【0059】
o−フタル酸、
イソフタル酸、
テレフタル酸、
5−メチルイソフタル酸、
5−tert−ブチルイソフタル酸、
5−アミノイソフタル酸、
5−ヒドロキシイソフタル酸、
2,5−ジメチルテレフタル酸、
テトラメチルテレフタル酸、
【0060】
1,4−ナフタレンジカルボン酸、
2,5−ナフタレンジカルボン酸、
2,6−ナフタレンジカルボン酸、
2,7−ナフタレンジカルボン酸、
1,4−アントラセンジカルボン酸、
1,4−アントラキノンジカルボン酸、
2,5−ビフェニルジカルボン酸、
4,4’−ビフェニルジカルボン酸、
1,5−ビフェニレンジカルボン酸、
4,4”−タ−フェニルジカルボン酸、
4,4’−ジフェニルメタンジカルボン酸、
4,4’−ジフェニルエタンジカルボン酸、
4,4’−ジフェニルプロパンジカルボン酸、
4,4’−ジフェニルヘキサフルオロプロパンジカルボン酸、
4,4’−ジフェニルエーテルジカルボン酸、
4,4’−ビベンジルジカルボン酸、
4,4’−スチルベンジカルボン酸、
4,4’−トランジカルボン酸、
4,4’−カルボニル二安息香酸、
4,4’−スルホニル二安息香酸、
4,4’−ジチオ二安息香酸、
【0061】
p−フェニレン二酢酸、
3,3’−p−フェニレンジプロピオン酸、
4−カルボキシ桂皮酸、
p−フェニレンジアクリル酸、
3,3’−[4,4’−(メチレンジ−p−フェニレン)]ジプロピオン酸、
4,4’−[4,4’−(オキシジ−p−フェニレン)]ジプロピオン酸、
4,4’−[4,4’−(オキシジ−p−フェニレン)]二酪酸、
(イソプロピリデンジ−p−フェニレンジオキシ)二酪酸、
【0062】
ビス(p−カルボキシフェニル)ジメチルシラン、
1,5−(9−オキソフルオレン)ジカルボン酸、
3,4−フランジカルボン酸、
4,5−チアゾールジカルボン酸、
2−フェニル−4,5−チアゾールジカルボン酸、
1,2,5−チアジアゾール−3,4−ジカルボン酸、
1,2,5−オキサジアゾール−3,4−ジカルボン酸、
2,3−ピリジンジカルボン酸、
2,4−ピリジンジカルボン酸、
2,5−ピリジンジカルボン酸、
2,6−ピリジンジカルボン酸、
3,4−ピリジンジカルボン酸、
3,5−ピリジンジカルボン酸、
3,6−ピリジンジカルボン酸等を挙げることが出来るが、これらのジカルボン酸はジカルボン酸ハライドの形のものであってもよい。
【0063】
本発明に係わるジカルボン酸若しくはジカルボン酸ハライドはこれらに限定されることなく、本発明の目的が達成される範囲内で他のジカルボン酸若しくはジカルボン酸ハライドを用いることもできる。また、これらのジカルボン酸若しくはジカルボン酸ハライドは単独で、または2種以上を組み合わせて用いることができる。
更に、ポリアミドイミドを合成するに際して別の酸成分としてトリメリット酸、またはその誘導体である塩化トリメリット酸無水物も有用である。
好ましく用いられるテトラカルボン酸二無水物として、以下の化合物が挙げられる。
【0064】
【化4】
【0065】
【化5】
【0066】
【化6】
【0067】
本発明に用いられるジアミンの具体例として以下のものを挙げることができる。
p−フェニレンジアミン、
m−フェニレンジアミン、
o−フェニレンジアミン、
p−キシレンジアミン、
m−キシレンジアミン、
p−キシリレンジアミン、
m−キシリレンジアミン、
2,4−ジアミノトルエン、
2,6−ジアミノトルエン、
2,3,5,6−テトラメチル−p−フェニレンジアミン、
2,5−ジメチル−p−フェニレンジアミン、
【0068】
3,3’−ジアミノジフェニルメタン、
4,4’−ジアミノジフェニルメタン、
3,3’−ジアミノジフェニルエタン、
4,4’−ジアミノジフェニルエタン、
1,3−ビス(4−アミノフェニル)プロパン、
2,2−ビス(4−アミノフェニル)プロパン、
2,2−ビス(3−アミノフェニル)プロパン、
2,2−ビス(4−アミノフェニル)パ−フルオロプロパン、
2,2−ビス(3−アミノフェニル)パ−フルオロプロパン、
【0069】
ビス(4−アミノ−3−メチルフェニル)メタン、
ビス(4−アミノ−2−メチルフェニル)メタン、
1,2−ビス(4−アミノ−3−メチルフェニル)エタン、
1,3−ビス(4−アミノ−3−メチルフェニル)プロパン、
1,2−ビス(4−アミノ−2−メチルフェニル)エタン、
1,3−ビス(4−アミノ−2−メチルフェニル)プロパン、
【0070】
1,4−ビス[(4−アミノフェニル)メチル]ベンゼン、
1,4−ビス[(3−アミノフェニル)メチル]ベンゼン、
1,4−ビス[(4−アミノフェニル)エチル]ベンゼン、
1,4−ビス[(3−アミノフェニル)エチル]ベンゼン、
1,4−ビス[(4−アミノ−3−メチル−フェニル)メチル]ベンゼン、
1,4−ビス[(4−アミノ−3−メチル−フェニル)エチル]ベンゼン、
【0071】
ビス−[(4−(4−アミノフェニルメチル)フェニル]メタン、
ビス−[(4−(4−アミノフェニルメチル)フェニル]エタン、
ビス−[(4−(3−アミノフェニルメチル)フェニル]メタン、
ビス−[(4−(3−アミノフェニルメチル)フェニル]エタン、
2,2’−ビス−[(4−(4−アミノフェニルメチル)フェニル]プロパン、
2,2’−ビス−[(4−(3−アミノフェニルメチル)フェニル)プロパン、
2,2’−ビス−[(4−(3−アミノフェニルメチル)フェニル)パ−フルオロプロパン、
【0072】
1,4−ビス(4−アミノフェノキシ)ベンゼン、
1,3−ビス(4−アミノフェノキシ)ベンゼン、
2,2−ビス(4−アミノフェノキシ)プロパン、
ビス[4−(4−アミノフェノキシ)フェニル]メタン、
2,2−ビス[4−(4−アミノフェノキシ)フェニル]エタン、
1,1−ビス[4−(4−アミノフェノキシ)フェニル]プロパン、
2,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン、
1,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン、
2,2−ビス[4−(2−アミノフェノキシ)フェニル]パ−フルオロプロパン、
2,2−ビス[4−(3−アミノフェノキシ)フェニル]パ−フルオロプロパン、
2,2−ビス[4−(4−アミノフェノキシ)フェニル]パ−フルオロプロパン、
2,2−ビス[4−(4−アミノフェノキシ)フェニル]ブタン、
【0073】
4,4’−ジアミノビフェニル、
3,3’−ジメチルベンジジン、
3,3’−ジメトキシベンジジン、
1,4−ビス(4−アミノフェニル)ベンゼン、
4,4’−ビス(4−アミノフェニル)ビフェニル、
4,4’−ジアミノタ−フェニル、
3,3’−ジメチル−4,4’−ジアミノビフェニル、
1,3−ビス[4−(4−アミノフェノキシ)フェニル]ベンゼン、
1,4−ビス[4−(4−アミノフェノキシ)フェニル]ベンゼン、
4,4−ビス[4−(4−アミノフェノキシ)フェニル]ビフェニル、
1,2−ビス[4−(4−アミノフェノキシ)フェニル]シクロヘキサン、
1,3−ビス[4−(4−アミノフェノキシ)フェニル]シクロヘキサン、
1,4−ビス[4−(4−アミノフェノキシ)フェニル]シクロヘキサン、
【0074】
1,5−ジアミノナフタレン、
2,6−ジアミノナフタレン、
2、7−ジアミノフルオレン、
9,9−ビス(4−アミノフェニル)フルオレン、
9,9−ビス(4−アミノフェニル)−10−アントラセン、
4,4’−(p−フェニレンジイソプロピリデン)ビスアニリン、
4,4’−(m−フェニレンジイソプロピリデン)ビスアニリン、
4,4’−ジアミノベンズアニリド、
3,3’−ジアミノベンゾフェノン、
3,4’−ジアミノベンゾフェノン、
4,4’−ジアミノベンゾフェノン、
3,3’−ジアミノジフェニルベンゾフェノン、
4,4’−ビス(4−アミノフェノキシ)ジフェニルケトン、
【0075】
3,3’−ジアミノジフェニルスルフィド、
4,4’−ジアミノジフェニルスルフィド、
ビス[4−(4−アミノフェノキシ)フェニル]スルフィド、
3,3’−ジアミノジフェニルスルホン、
4,4’−ジアミノジフェニルスルホン、
ビス[4−(4−アミノフェノキシ)フェニル]スルホン、
3,3’−ジアミノジフェニルエ−テル、
4,4’−ジアミノジフェニルエ−テル、
3,4’−ジアミノジフェニルエ−テル、
ビス−(4−アミノフェニル)ジエチルシラン、
ビス−(4−アミノフェニル)ジフェニルシラン、
ビス−(4−アミノフェニル)エチルホスフィンオキサイド、
【0076】
2,2−ビス[4−(3−カルバモイル−4−アミノフェノキシ)フェニル]パ−フルオロプロパン、
2,2−ビス−(3−スルファモイル−4−アミノフェニル)パ−フルオロプロパン、
2,2−ビス−(3−カルボキシ−4−アミノフェニル)パ−フルオロプロパン、
2,2−ビス[4−(3−スルファモイル−4−アミノフェノキシ)フェニル]パ−フルオロプロパン、
2,2−ビス[4−(3−カルボキシ−4−アミノフェノキシ)フェニル]パ−フルオロプロパン、
【0077】
1,3−ビス[2−{4−(4−アミノフェノキシ)フェニル}パ−フルオロイソプロピル]ベンゼン、
2,4−ビス(β−アミノ−t−ブチル)トルエン、
ビス(p−β−メチル−γ−アミノペンチル)ベンゼン、
ビスp−(1,1−ジメチル−5−アミノペンチル)ベンゼン、
ビス(p−β−アミノ−t−ブチルフェニル)エ−テル、
ビス(4−アミノベンゾルオキシ)メタン、
ビス(4−アミノベンゾルオキシ)エタン、
ビス(4−アミノベンゾルオキシ)プロパン、
ビス(4−アミノベンゾルオキシ)シクロヘキサン、
2,3−ジアミノピリジン、
2,6−ジアミノピリジン、
3,4−ジアミノピリジン、
2,4−ジアミノピリジン、
ジアミノピリミジン、
ジアミノピペラジン、
ビス−(4−アミノフェニル)−N−ブチルアミン、
N,N−ビス−(4−アミノフェニル)−N−メチルアミン、
N−(3−アミノフェニル)−4−アミノベンズアミド等。
【0078】
1,4−ジアミノシクロヘキサン、
1,3−ビス(アミノメチル)シクロヘキサン、
1,4−ビス(アミノメチル)シクロヘキサン、
イソホロンジアミン、
ノルボルナンジアミン、
4,4’−ジアミノジシクロヘキシルメタン、
ビス(2−メチル−4−アミノシクロヘキシル)メタン、
テトラヒドトジシクロペンタジエニレンジアミン、
ヘキサヒドロ−4,7−メタノインダニレンジメチレンジアミン、
トリシクロ[6.2.1.02、7]−ウンデシレンジメチルジアミン、
4,4’−メチレンビス(シクロヘキシルアミン)、
【0079】
2,5−ビス(アミノメチル)−ビシクロヘプタン、
2,6−ビスアミノメチル−ビシクロヘプタン、
2,3−ジアミノビシクロ[2,2,1]ヘプタン、
2,5−ジアミノビシクロ[2,2,1]ヘプタン、
2,6−ジアミノビシクロ[2,2,1]ヘプタン、
2,7−ジアミノビシクロ[2,2,1]ヘプタン、
2,3−ジアミノ−7−アザビシクロ[2,2,1]ヘプタン、
2,5−ジアミノ−7−アザビシクロ[2,2,1]ヘプタン、
2,6−ジアミノ−7−アザビシクロ[2,2,1]ヘプタン、
2,3−ジアミノ−7−チアビシクロ[2,2,1]ヘプタン、
2,5−ジアミノ−7−チアビシクロ[2,2,1]ヘプタン、
2,6−ジアミノ−7−チアビシクロ[2,2,1]ヘプタン、
2,3−ジアミノビシクロ[2,2,2]オクタン、
2,5−ジアミノビシクロ[2,2,2]オクタン、
2,6−ジアミノビシクロ[2,2,2]オクタン、
2,5−ジアミノビシクロ[2,2,2]オクタン−7−エン、
2,5−ジアミノ−7−アザビシクロ[2,2,2]オクタン、
2,5−ジアミノ−7−オキサビシクロ[2,2,2]オクタン、
2,5−ジアミノ−7−チアビシクロ[2,2,2]オクタン、
2,6−ジアミノビシクロ[3,2,1]オクタン、
2,6−ジアミノアザビシクロ[3,2,1]オクタン、
2,6−ジアミノオキサビシクロ[3,2,1]オクタン、
2,6−ジアミノチアビシクロ[3,2,1]オクタン、
2,6−ジアミノビシクロ[3,2,2]ノナン、
2,6−ジアミノビシクロ[3,2,2]ノナン−8−エン、
2,6−ジアミノ−8−アザビシクロ[3,2,2]ノナン、
2,6−ジアミノ−8−オキサビシクロ[3,2,2]ノナン、
2,6−ジアミノ−8−チアビシクロ[3,2,2]ノナン等。
【0080】
エチレンジアミン、トリメチレンジアミン、プロパンジアミン、テトラメチレンジアミン、ペンタメチレンジアミン、ヘキサメチレンジアミン、ヘプタメチレンジアミン、オクタメチレンジアミン、ノナメチレンジアミン、4,4−ジアミノヘプタメチレンジアミン等の脂肪族ジアミン化合物、およびアルキレン基の中に酸素原子を有するアルキレンジアミン等。
【0081】
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−メチルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−エチルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−プロピルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ブチルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ペンチルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ヘキシルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ヘプチルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−オクチルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ノニルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−デシルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ウンデシルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ドデシルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−トリデシルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−テトラデシルシクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−n−ペンタデシルシクロヘキサン、
【0082】
1,1−ビス(4−アミノフェニル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−メチルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−エチルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−プロピルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ブチルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ペンチルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ヘキシルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ヘプチルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−オクチルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ノニルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−デシルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ウンデシルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ドデシルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−トリデシルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−テトラデシルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−n−ペンタデシルシクロヘキサン、
【0083】
1,1−ビス(4−アミノフェニル)−4−シクロヘキシルシクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−メチル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−エチル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−プロピル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ブチル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ペンチル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ヘキシル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ヘプチル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−オクチル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ノニル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−デシル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ウンデシル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ドデシル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−トリデシル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−テトラデシル−トランス−シクロヘキシル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−(4−n−ペンタデシル−トランス−シクロヘキシル)シクロヘキサン、
【0084】
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(シクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−メチルシクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−エチルシクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−プロピルシクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−ブチルシクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−ペンチルシクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−ヘキシルシクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−ヘプチルシクロヘキシル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(4−オクチルシクロヘキシル)シクロヘキサン、
【0085】
1,1−ビス(4−アミノフェニル)−4−(シクロヘキシルメチル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−メチルシクロヘキシル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−エチルシクロヘキシル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−プロピルシクロヘキシル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ブチルシクロヘキシル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ペンチルシクロヘキシル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ヘキシルシクロヘキシル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ヘプチルシクロヘキシル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−オクチルシクロヘキシル)メチル〕シクロヘキサン、
【0086】
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−(フェニルメチル)シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−4−〔(4−メチルフェニル)メチル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル)−4−〔(4−エチルフェニル)メチル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル)−4−〔(4−プロピルフェニル)メチル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル)−4−〔(4−ブチルフェニル)メチル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル)−4−〔(4−ペンチルフェニル)メチル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル)−4−〔(4−ヘキシルフェニル)メチル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル)−4−〔(4−ヘプチルフェニル)メチル〕シクロヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル)−4−〔(4−オクチルフェニル)メチル〕シクロヘキサン、
【0087】
1,1−ビス(4−アミノフェニル)−4−(フェニルメチル)シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−メチルフェニル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−エチルフェニル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−プロピルフェニル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ブチルフェニル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ペンチルフェニル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ヘキシルフェニル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−ヘプチルフェニル)メチル〕シクロヘキサン、
1,1−ビス(4−アミノフェニル)−4−〔(4−オクチルフェニル)メチル〕シクロヘキサン、
【0088】
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−(フェニルメチル)シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−メチルフェニル)メチル〕シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−エチルフェニル)メチル〕シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−プロピルフェニル)メチル〕シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−ブチルフェニル)メチル〕シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−ペンチルフェニル)メチル〕シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−ヘキシルフェニル)メチル〕シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−ヘプチルフェニル)メチル〕シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−〔(4−オクチルフェニル)メチル〕シクロヘキサン、
【0089】
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−メチルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−エチルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−プロピルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−ブチルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−ペンチルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−ヘキシルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−ヘプチルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−オクチルクロヘキサン。
【0090】
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(シクロヘキシルエチルシクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−メチル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−エチル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−プロピル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−ブチル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−ペンチル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−アミル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−ヘキシル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−ヘプチル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−オクチル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−ノニル−トランス−シクロヘキシル)エチル]シクロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}−4−[2−(4−ドデシル−トランス−シクロヘキシル)エチル]シクロヘキサン、
【0091】
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕ペンタン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ペンタン、
3,3−ビス〔4−(4−アミノフェノキシ)フェニル〕ペンタン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘキサン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘキサン、
3,3−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘキサン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘプタン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘプタン、
3,3−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘプタン、
4,4−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘプタン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕オクタン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕オクタン、
3,3−ビス〔4−(4−アミノフェノキシ)フェニル〕オクタン、
4,4−ビス〔4−(4−アミノフェノキシ)フェニル〕オクタン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕ノナン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ノナン、
3,3−ビス〔4−(4−アミノフェノキシ)フェニル〕ノナン、
4,4−ビス〔4−(4−アミノフェノキシ)フェニル〕ノナン、
5,5−ビス〔4−(4−アミノフェノキシ)フェニル〕ノナン、
1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕デカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕デカン、
3,3−ビス〔4−(4−アミノフェノキシ)フェニル〕デカン、
4,4−ビス〔4−(4−アミノフェノキシ)フェニル〕デカン、
5,5−ビス〔4−(4−アミノフェノキシ)フェニル〕デカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ウンデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ドデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕トリデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕テトラデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ペンタデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘキサデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ヘプタデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕オクタデカン、
2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕ノナデカン、
【0092】
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}ペンタン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ペンタン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}ペンタン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘキサン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘキサン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘプタン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘプタン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘプタン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘプタン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}オクタン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}オクタン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}オクタン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}オクタン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}ノナン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ノナン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}ノナン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}ノナン、
5,5−ビス{4−[(4−アミノフェニル)メチル]フェニル}ノナン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}デカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}デカン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}デカン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}デカン、
5,5−ビス{4−[(4−アミノフェニル)メチル]フェニル}デカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ウンデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ドデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}トリデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}テトラデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ペンタデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘキサデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ヘプタデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}オクタデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}ノナデカン、
【0093】
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロペンタン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロペンタン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロペンタン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘキサン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘキサン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘキサン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘプタン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘプタン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘプタン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘプタン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロオクタン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロオクタン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロオクタン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロオクタン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロノナン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロノナン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロノナン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロノナン、
5,5−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロノナン、
1,1−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロデカン、
3,3−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロデカン、
4,4−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロデカン、
5,5−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロウンデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロドデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロトリデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロテトラデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロペンタデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘキサデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロヘプタデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロオクタデカン、
2,2−ビス{4−[(4−アミノフェニル)メチル]フェニル}パ−フルオロノナデカン等。
【0094】
4−[3−(4−ビフェニルオキシ)プロポキシ]−1,3−ジアミン、
4−[8−(4−ビフェニルオキシ)オクチルオキシ]−1,3−ジアミノベンゼン、
4−[3−(4−シアノビフェニル−4’−オキシ)プロポキシ]−1,3−ジアミノベンゼン、
4−[12−(4−シアノビフェニル−4’−オキシ)ドデシルオキシ]−1,3−ジアミノベンゼン、
4−[6−(4−メトキシビフェニル−4’−オキシ)ヘキシルオキシ]−1,3−ジアミノベンゼン、
4−[3−(4−フルオロビフェニル−4’−オキシ)プロポキシ]−1,3−ジアミノベンゼン、
【0095】
2,4−ジアミノ安息香酸ドデシル、
2,4−ジアミノ安息香酸オクチル、
1,5−ジアミノ−2−オクチルオキシカルボニルアミノベンゼン、
1,4−ジアミノ−3−[4−(4−アルキルシクロヘキシル)シクロヘキシルオキシ]ベンゼン、
1,4−ジアミノ−3−[4−(4−アルキルフェニル)シクロヘキシルオキシ]ベンゼン、
1,4−ジアミノ−3−((4−アルキルタ−フェニル)オキシ)ベンゼン、
1,4−ジアミノ−(2−アルキル)ベンゼン、
1,4−ジアミノ−(2,5−ジアルキル)ベンゼン、
2−アルキルオキシ−1,4−ジアミノベンゼン等。
【0096】
1−シクロヘキシル−4−(4−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−メチルシクロヘキシル)−4−(4−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−プロピルシクロヘキシル)−4−(4−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−ペンチルシクロヘキシル)−4−(4−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−オクチルシクロヘキシル)−4−(4−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−デシルシクロヘキシル)−4−(4−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−ドデシルシクロヘキシル)−4−(4−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−シクロヘキシル−4−(3−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−メチルシクロヘキシル)−4−(3−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−プロピルシクロヘキシル)−4−(3−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−ペンチルシクロヘキシル)−4−(3−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−オクチルシクロヘキシル)−4−(3−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−デシルシクロヘキシル)−4−(3−アミノベンジル−2−アミノフェニル)シクロヘキサン、
1−(4−ドデシルシクロヘキシル)−4−(3−アミノベンジル−2−アミノフェニル)シクロヘキサン等。
【0097】
さらに、コレステリル、アンドロステリル、β―コレステリル、エピアンドロステリル、エリゴステリル、エストリル、11α−ヒドロキシメチルステリル、11α−プロゲステリル、ラノステリル、メラトラニル、メチルテストロステリル、ノレチステリル、プレグネノニル、β−シトステリル、スチグマステリル、テストステリル、酢酸コレステロ−ルエステル等のステロイド骨格の側鎖を有するジアミン。
【0098】
【化7】
【0099】
【化8】
【0100】
これらの式においてRは水素または炭素数1〜20のアルキル基を表し、任意の−CH2−は−O−、−CH=CH−または−C≡C−で置き換えられてもよい。また、本発明に係わるジアミンはこれらに限定されることなく、本発明の目的が達成される範囲内で他のジアミンを用いることができることは言うまでもない。また、これらのジアミンは単独で、または2種以上を組み合わせて用いることができる。
【0101】
さらに、本発明に係わる上記のジアミンと併用することができるその他のジアミンとして、シロキサン結合を含んだシロキサン系ジアミンを挙げることができる。該シロキサン系ジアミンは特に限定されるものではないが、式(3)で表されるものが本発明において好ましく使用することができる。
【0102】
【化9】
(式(3)中、R2およびR3は独立して炭素数1〜3のアルキルまたはフェニルである。また、R4はメチレン、フェニレンまたはアルキル置換されたフェニレンである。xは1〜6の整数を表し、yは1〜10の整数を表す)。
【0103】
なお、前記のポリアミド酸またはポリアミドの原料として、これらの反応末端を形成するためのモノアミン化合物、または/およびモノカルボン酸無水物を併用することも可能である。
【0104】
さらに、本発明の液晶配向剤ワニスに有機ケイ素化合物あるいはチタン系のカップリング剤を添加すれば、本発明の液晶配向剤ワニスを用いて形成される配向膜のガラス基板への密着性がさらに改善される。有機ケイ素化合物は特に限定されるものではないが、例えば、アミノプロピルトリメトキシシラン、アミノプロピルトリエトキシシラン、ビニルトリメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、ビニルトリエトキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシランなどのシランカップリング剤、ポリジメチルシロキサン、ポリジフェニルシロキサンなどのシリコーンオイル等を挙げることができる。
【0105】
該有機ケイ素化合物あるいはチタン系カップリング剤の液晶配向剤ワニスへの添加割合は特に限定されるものではないが、液晶配向剤ワニスが含有するポリマー成分100重量部に対し、0.01〜5重量部、好ましくは0.1〜3重量部である。
【0106】
本発明の液晶配向剤ワニス中のポリマ−成分濃度は、0.1〜40重量%であることが好ましい。ポリマ−成分の濃度がこの範囲内であれば、適切な粘度を有する液晶配向剤ワニスが得られ、ワニスを容易に希釈して最適な膜厚に調整することができる。スピンナ−法や印刷法の場合には、膜厚を良好に保つために、通常10重量%以下とすることが多い。その他の塗布方法、例えばディッピング法ではさらに低濃度とすることもあり得る。通常のスピンナ−法や印刷法等では0.1重量%以上、好ましくは0.5〜10重量%である。しかしながら、液晶配向剤ワニスの塗布方法によっては、さらに希薄な濃度で使用しても良い。
【0107】
本発明の液晶配向剤ワニスにおいて前記ポリマー成分と共に用いられる溶剤は、各種ポリマー成分やアルケニル置換ナジイミド化合物を溶解する能力を持つことだけが選択条件であり、他に格別の制限はない。従って、ポリアミド酸、可溶性ポリイミド、ポリアミド、およびポリアミドイミドの、それぞれの製造工程や用途方面で通常使用されている溶剤から、目的に応じた溶剤を適宜選択すればよい。これらの溶剤の例として、ポリアミド酸、可溶性ポリイミド、ポリアミド、およびポリアミドイミドに対し良溶媒である非プロトン性極性有機溶剤、例えばN−メチル−2−ピロリドン(以降、NMPと略記する。)、ジメチルイミダゾリジノン、N−メチルカプロラクタム、N−メチルプロピオンアミド、N,N−ジメチルアセトアミド(DMAc)、ジメチルスルホオキシド(DMSO)、N,N−ジメチルホルムアミド(DMF)、ジエチルアセトアミドまたはγ−ブチルラクトン(GBL)等を挙げることができる。
【0108】
また、アルケニル置換ナジイミドに対して良溶媒である他の溶剤としては、メタノール、エタノール、アセトン、メチルエチルケトン、メチルイソブチルケトン、テトラヒドロフラン、1,4−ジオキサン、メチルアセテート、ビニルアセテート、クロロホルム、クロロベンゼン、トルエン、キシレン、クレゾール、アセトニトリル、ピリジン、エチレングリコールジメチルエーテル等を挙げることができる。
【0109】
また、塗布性改善等を目的とした他の溶剤、例えば乳酸アルキル、3−メチル−3−メトキシブタノール、テトラリン、イソホロン、エチレングリコールモノブチルエーテル(以降、BCと略記する。)等のエチレングリコールモノアルキルエーテル、ジエチレングリコールモノエチルエーテル等のジエチレングリコールモノアルキルエーテル、エチレングリコールモノアルキルまたはフェニルアセテート、トリエチレングリコールモノアルキルエーテル、プロピレングリコールモノブチルエーテル等のプロピレングリコールモノアルキルエーテル、マロン酸ジエチル等のマロン酸ジアルキル、ジプロピレングリコールモノメチルエーテル等のジプロピレングリコールモノアルキルエーテル若しくはこれらのアセテート類等のエステル化合物系溶剤等も挙げることができる。また、本発明において該溶媒は混合溶媒であっても良い。
【0110】
本発明の液晶配向剤ワニスは、必要により各種の添加剤を含むことができる。例えば、塗布性の向上、帯電防止の向上などを望む場合にはかかる目的に沿った界面活性剤を配合してもよく、配向膜の特性を損なわない範囲において陰イオン界面活性剤、陽イオン界面活性剤、両性界面活性剤、非イオン界面活性剤を配合してもよい。
【0111】
本発明の配向膜はあらゆる液晶表示素子に用いることができ、且つあらゆる液晶表示素子において本発明の効果を奏する。その中でも、強い配向規制力を得るために強いラビング操作を行うモード、たとえば、IPSモード、STNモード、TNモード、OCBモード、強誘電性型、反強誘電性型、また電圧印加時に液晶分子の倒れ方を制御させるためにラビングを行う場合があるVAモードでは、ラビング傷が発生しない、あるいは配向不良がないと云った本発明の効果が顕著に認められる。
【0112】
本発明の配向膜の製造方法は特に限定されるものではないが、具体的には下記の手順によって製造することができる。本発明のワニスを刷毛塗り法、浸漬法、スピンナー法、スプレー法または印刷法等により透明電極付きガラス基板あるいは透明電極付きプラスティック基板に塗布する。次いで、該電極付き基板の温度を50〜150℃、好ましくは80〜120℃とし溶媒を蒸発させる。その後、透明電極付きガラス基板では、該温度を150〜400℃、好ましくは180〜280℃として焼成することにより該ガラス基板表面に膜が形成される。特にプラスチック基板を使用する場合は、基板の耐熱温度を考慮すると120〜160℃程度の低温度下で焼成を行うことが好ましい。そして、この膜表面を布などで一方向にラビングすることにより本発明の配向膜が得られる。
【0113】
なお、透明電極付きガラス基板あるいはプラスチック基板に本発明のワニスを塗布する前に、該基板表面をシランカップリング剤で処理すれば、該基板表面に形成される配向膜と基板との接着性がさらに向上する。
【0114】
本発明の液晶表示素子に使用する液晶組成物は特に限定されるものではなく、何れの液晶組成物を用いてもよい。本発明の配向膜と共に用いられるTN型、STN型、IPS型、OCB型の液晶表示素子の作製に用いる場合、共に用いられる誘電率異方性が正の液晶組成物としては特に制限はなく、各種の液晶組成物を用いることができ、例えば、特許3086228号公報、特許2635435号公報、特表平5−501735号公報、特開平8−157828号公報、特開平8−231960号公報、特開平9−241644号公報(EP 885272A1)、特開平9−302346号公報(EP 806466A1)、特開平8−199168号公報(EP 722998A1)、特開平9−235552号公報、特開平9−255956号公報、特開平9−241643号公報(EP 885271A1)、特開平10−204016号公報(EP 844229A1)、特開平10−204436号公報、特開平10−231482号公報、特開2000−087040公報、特開2001−48822公報、などに開示されている液晶組成物が好ましい。
【0115】
また、本発明の液晶配向膜を、VA型の液晶表示素子の作製に用いる場合、共に用いられる誘電率異方性が負の液晶組成物として、例えば、特開昭57−114532号公報、特開平2−4725号公報、特開平4−224885号公報、特開平8−40953号公報、特開平8−104869号公報、特開平10−10168076号公報、特開平10−168453号公報、特開平10−236989号公報、特開平10−236990号公報、特開平10−236992号公報、特開平10−236993号公報、特開平10−236994号公報、特開平10−237000号公報、特開平10−237004号公報、特開平10−237024号公報、特開平10−237035号公報、特開平10−237075号公報、特開平10−237076号公報、特開平10−237448号公報(EP967261)、特開平10−287874号公報、特開平10−287875号公報、特開平10−291945号公報、特開平11−029581号公報、特開平11−080049号公報、特開2000−256307公報、特開2001−019965公報、特開2001−072626公報および特開2001−192657公報などに開示されている液晶組成物が好ましい。
【0116】
【実施例】
以下、実施例により本発明を詳細に説明するが、本発明はこれらの実施例に限定されるものではない。実施例中、NMRはすべて重クロロホルム中で測定した。分子量の測定はGPCを用い、ポリスチレンを標準溶液とし、溶出液はDMFを用いた。
【0117】
液晶表示素子の評価法
以下に実施例で用いた液晶表示素子の評価法を記載する。なお、本実施例中に記載された諸物性の測定値は、25℃の値である。
【0118】
(1−1)ラビングによる削れ
ラビング後の配向膜の削れを目視により観測した。
○:削れなし
×:削れあり
(1−2)表示ムラの有無
液晶セルに電圧を印加し、表示を行ったとき、表示不良となっている部分を目視により観察した。
○:表示不良なし
×:表示不良あり
【0119】
(2)液晶配向膜と基板の密着性
液晶配向膜の基板の密着性は、JIS K5400 8.5.2の碁盤目テープ法に準じて、試験片に1mmの碁盤目を100個作り、セロテープ(登録商標)によりピーリング試験を行った。そして碁盤目の剥離状態を観察し、次の条件で評価した。
○:100/100で剥れのないもの
△:50/100〜90/100
×:0/100〜50/100
【0120】
(3)液晶配向膜の表面硬度
配向膜の表面硬度(押し込み硬度)測定は、株式会社エリオニクス製 超微小押し込み硬さ試験機(ナノインデンテーションテスター) ENT1100aを用いて、押し込み荷重10mgf(250ステップ分割)、試験荷重保持時間1秒で測定した。
【0121】
(4)プレチルト角
クリスタルローテーション法により行った。なお、測定波長は589nmである。
【0122】
(5)電圧保持率
「水嶋他、第14回液晶討論会予稿集、p78」に記載の方法に準拠し行った。測定時セルに印加した電圧はゲート幅69μs、波高±4.5V、周波数30Hzまたは0.3Hzとした。
【0123】
アルケニル置換ナジイミド化合物は丸善石油化学株式会社より販売されている下記構造式を有する3種類の化合物を用いた。
BANI−H:式(2)で表される化合物である。
【化10】
【0124】
BANI−M:式(3)で表される化合物である。
【化11】
【0125】
BANI−X:式(4)で表される化合物である。
【化12】
【0126】
本発明の実施態様を具体的に示すために各種ポリマーを含有するワニスを調製し(実施例1〜9)、そのワニスと上述したアルケニル置換ナジイミドを調合して本発明の液晶配向剤ワニスを調製し、それから得られた配向膜を用いて性能を評価した(実施例10〜117)。尚、アルケニル置換ナジイミドを添加しないワニスについては比較例1〜9として本発明との比較対象とした。
【0127】
実施例1(液晶配向剤ワニスA−1(ポリアミド酸型)の調製)
200mL4つ口フラスコに、4,4’−ジアミノジフェニルメタン(以下、DDMと略記する。)を3.0164g(1.52×10−2mol)、脱水N−メチル−2−ピロリドン(以下、NMPと略記する。)54.00gをそれぞれ入れ、乾燥窒素気流下で攪拌溶解した。反応系の温度を5℃に保ちながら、シクロブタンテトラカルボン酸二無水物(以下、CBDAと略記する。)を2.9836g(1.52×10−2mol)加え、その後特に温度コントロールすることなく30時間反応させた。最後に、ブチルセロソルブ(以下、BCと略記する。)をそれぞれ40.00g加えて、ポリマー成分の濃度が6重量%のポリアド酸ワニスを合成した。合成したワニスを液晶配向剤ワニスA1とする。尚、本発明の実施例では、反応中の粘度をチェックしながら反応を行い、ブチルセロソルブを添加後の液晶配向剤ワニスの粘度が55〜65mPa・s(E型粘度計を使用、測定温度25℃)になった時点で反応を終了とし、低温にて保存した。
【0128】
実施例2(液晶配向剤ワニスB−1(ポリアミド酸型)の調製)
ジアミン化合物としてDDMの代わりに4,4’−ジアミノジフェニルエタン(以下、DDEtと略記する。)を1.0657g(5.02×10−3mol)、さらに1、1−ビス(4−((アミノフェニル)メチル)フェニル)−4−ヘプチルシクロヘキサン(以降、APM7C6と略記する。)を2.7351g(5.02×10−3mol)加え、また、酸二無水物としてCBDAの代わりに、ピロメリット酸二無水物(以下、PMDAと略記する。)を2.1900g(1.00×10−2mol)加えた以外は実施例1に準拠して液晶配向剤ワニスB1を合成した。
【0129】
実施例3(液晶配向剤ワニスC−1(ポリアミド酸型)の調製)
ジアミン化合物としてDDMの代わりに5−((4−(4−(4−ペンチルシクロヘキシル)シクロヘキシル)フェニル)メチル―1,3―ジアミノベンゼン(以下5CHCHPhMDAB略記する。)を3.9891g(9.22×10−3mol)加え、さらに、酸二無水物としてCBDAの代わりに、PMDAを2.0109g(9.22×10−3mol)加えた以外は実施例1に準拠して液晶配向剤ワニスC1を合成した。
【0130】
実施例4(液晶配向剤ワニスD−1(ポリアミド型)の調製)
(ポリアミドの調製)
500mL3つ口フラスコに、ジアミン化合物として、DDEtを1.1692g(5.51×10−3mol)加え、さらにAPM7C6を3.0007g(5.51×10−3mol)加え、酸化合物として、テレフタル酸を(以下、TPAと略記する。)1.8300g(1.10×10−2mol)加えた。また、ピリジン1mL、および塩化リチウムを2.803g(6.61×10−2mol)入れ、NMP(200mL)に溶解させた。この溶液に亜リン酸トリフェニルを10.2448g(3.31×10−2mol)滴下し、窒素気流中100℃で4時間反応させた。冷却後、反応物をメタノールにあけ、ポリマーを再沈澱させてろ過し粗生成物を得た。この粗生成物を純水500mLで2回、メタノール500mLで1回それぞれ30分程度煮沸洗浄した。120℃で8時間真空乾燥させポリアミドを4.8g(重量平均分子量10万)得た。
【0131】
(ポリアミドのメチル化)
3つ口フラスコへ、上記ポリアミド4.7gを入れ、NMP150mLに溶解させた。この溶液にナトリウムメトキシドを0.9469g(1.75×10−2mol)加え、さらに室温で3時間攪拌した。この溶液にヨウ化メチルを2.9856g(2.10×10−2mol)加え、さらに室温で2時間反応させた。反応物を純水2.5Lにあけて再沈澱させ、ろ過した後、純水1Lで2回それぞれ30分間煮沸洗浄した後、純水/IPA(重量比1/1)混合溶媒500mLで一回洗浄した。120℃で9時間真空乾燥させポリメチルアミドを3.8g得た。このポリマーをポリアミド−1(重量平均分子量は6万)とし、ポリアミド−1を実施例1と同様にNMP、BCを用いて溶解させたものを液晶配向剤ワニスD−1とする。また、アミド水素のメチル基への置換率はNMR法による測定からそれぞれ100%であった。
【0132】
実施例5(ポリアミドイミド:E−1の調製)
50mlの3つ口フラスコにジアミン化合物としてDDEtを1.1163g(5.26×10−3mol)、また、APM7C6を2.8650g(5.26×10−3mol)入れ、NMP20gに溶解した。この溶液にPMDAを1.1470g(5.26×10−3mol)加え、窒素気流中、1時間攪拌した。次いでテレフタル酸ジクロリド(TPACl)を1.0676g(5.26×10−3mol)加えた。その後ピリジン1mlをそれぞれ加え、さらに2時間攪拌した。反応終了後、無水酢酸20mlをそれぞれ加え100℃で1時間反応させた。冷却後反応物をメタノール300mlに加え、ポリマーを再沈澱させた。この粗生成物を、純水150mlで2回、メタノール150mlで1回、それぞれ30分程度煮沸洗浄した。120℃で7時間真空乾燥させポリアミドイミドをそれぞれ4.8g得た。このときの重量平均分子量は11万であった。
【0133】
3つ口フラスコに上記ポリアミドイミドを1.0g入れ、NMP(20ml)に溶解させた。ここに60%水素化ナトリウムをそれぞれ94mg(2.3mmol) を加え、室温で3時間攪拌させた。この溶液にヨウ化メチル430g(3.0mmol)をそれぞれ添加し、さらに室温で2時間反応させた。反応物を純水300mlに再沈させ、ろ過した後、純水150mlで2回各30分間煮沸洗浄した後、純水/イソプロピルアルコール(IPAと略記する。)(重量比1/1)混合溶媒50mlで1回洗浄した。120℃で8時間真空乾燥させ目的とするポリアミドイミドを960mg得た。このポリマーをそれぞれポリアミドイミド−1とする。このときの重量平均分子量は4.3万であり、アミド水素のメチル基への置換率は、NMR法による測定から97%であった。また、実施例1と同様にNMP、BCを用いて溶解させたもの液晶配向剤ワニスE−1とする。
【0134】
実施例6(混合ワニスの調製−1)
実施例1に準拠して得た液晶配向剤ワニスA−1のポリマー成分が90重量%および実施例2に準拠して得た液晶配向剤ワニスB−1のポリマー成分が10重量%となるように2種類のワニスを混合して、液晶配向剤ワニス(B−1/A−1:重量比1/9)を調製した。
【0135】
実施例7〜9(混合ワニスの調製−2)
液晶配向剤ワニスC−1、D−1、E−1についても実施例6と同様に、各液晶配向剤ワニス中のポリマー成分の重量と液晶配向剤ワニスA−1のポリマー成分の重量比が1/9になるように、それぞれ液晶配向剤ワニスA−1と混合して、液晶配向剤ワニスC−1/A−1(重量比1/9)(実施例7)、液晶配向剤ワニスD−1/A−1(重量比1/9)(実施例8)、液晶配向剤ワニスE−1/A−1(重量比1/9)(実施例9)を調製した。
【0136】
実施例10〜11
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスA−1への添加>
実施例1の方法で得られた液晶配向剤ワニスA−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例10では0.0060g、実施例11では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例10ではA−2、実施例11ではA−3とする。
【0137】
実施例12〜13
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスA−1への添加>
アルケニル置換ナジイミド化合物をBANI−Mに変更し、実施例12では0.0060g、実施例13では0.0600gをNMP10gに溶解して添加した以外は実施例10〜11と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例12ではA−4、実施例13ではA−5とする。
【0138】
実施例14〜15
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスA−1への添加>
アルケニル置換ナジイミド化合物をBANI−Xに変更し、実施例14では0.0060g、実施例15では0.0600gをNMP10gに溶解して添加した以外は実施例10〜11と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例14ではA−6、実施例15ではA−7とする。
【0139】
実施例16〜17
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスB−1への添加>
実施例2の方法で得られた液晶配向剤ワニスB−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例16では0.0060g、実施例17では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例16ではB−2、実施例17ではB−3とする。
【0140】
実施例18〜19
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスB−1への添加>
アルケニル置換ナジイミド化合物をBANI−Mに変更し、実施例18では0.0060g、実施例19では0.0600gをNMP10gに溶解して添加した以外は実施例16〜17と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例18ではB−4、実施例19ではB−5とする。
【0141】
実施例20〜21
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスB−1への添加>
アルケニル置換ナジイミド化合物をBANI−Xに変更し、実施例20では0.0060g、実施例21では0.0600gをNMP10gに溶解して添加した以外は実施例16〜17と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例2ではB−6、実施例21ではB−7とする。
【0142】
実施例22〜23
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスC−1への添加>
実施例3の方法で得られた液晶配向剤ワニスC−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例22では0.0060g、実施例23では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例22ではC−2、実施例23ではC−3とする。
【0143】
実施例24〜25
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスC−1への添加>
アルケニル置換ナジイミド化合物をBANI−Mに変更し、実施例24では0.0060g、実施例25では0.0600gをNMP10gに溶解して添加した以外は実施例22〜23と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例24ではC−4、実施例19ではC−5とする。
【0144】
実施例26〜27
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスC−1への添加>
アルケニル置換ナジイミド化合物をBANI−Xに変更し、実施例20では0.0060g、実施例21では0.0600gをNMP10gに溶解して添加した以外は実施例22〜23と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例26ではC−6、実施例27ではC−7とする。
【0145】
実施例28〜29
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスD−1への添加>
実施例4の方法で得られた液晶配向剤ワニスD−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例28では0.0060g、実施例29では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例22ではD−2、実施例23ではD−3とする。
【0146】
実施例30〜31
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスD−1への添加>
アルケニル置換ナジイミド化合物をBANI−Mに変更し、実施例30では0.0060g、実施例31では0.0600gをNMP10gに溶解して添加した以外は実施例28〜29と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例30ではD−4、実施例31ではD−5とする。
【0147】
実施例32〜33
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスD−1への添加>
アルケニル置換ナジイミド化合物をBANI−Xに変更し、実施例32では0.0060g、実施例33では0.0600gをNMP10gに溶解して添加した以外は実施例28〜29と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例32ではD−6、実施例33ではD−7とする。
【0148】
実施例34〜35
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスE−1への添加>
実施例5の方法に準拠して得られた液晶配向剤ワニスE−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例34では0.0060g、実施例35では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例34ではE−2、実施例35ではE−3とする。
【0149】
実施例36〜37
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスE−1への添加>
アルケニル置換ナジイミド化合物をBANI−Mに変更し、実施例36では0.0060g、実施例37では0.0600gをNMP10gに溶解して添加した以外は実施例34〜35と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例36ではE−4、実施例37ではE−5とする。
【0150】
実施例38〜39
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスE−1への添加>
アルケニル置換ナジイミド化合物をBANI−Xに変更し、実施例38では0.0060g、実施例39では0.0600gをNMP10gに溶解して添加した以外は実施例34〜35と同様の方法で添加を行った。これらの液晶配向剤ワニスを実施例2ではE−6、実施例21ではE−7とする。
【0151】
実施例40〜41
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスB−1/A−1への添加>
実施例6の方法で得られた液晶配向剤ワニスB−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例40では0.0060g、実施例41では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例40ではB−2/A−2、実施例41ではB−3/A−3とする。
【0152】
実施例42〜43
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスB−1/A−1への添加>
実施例6の方法で得られた液晶配向剤ワニスB−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Mを実施例42では0.0060g、実施例43では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例42ではB−4/A−4、実施例43ではB−5/A−5とする。
【0153】
実施例44〜45
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスB−1/A−1への添加>
実施例6の方法で得られた液晶配向剤ワニスB−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Xを実施例44では0.0060g、実施例45では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例44ではB−6/A−6、実施例45ではB−7/A−7とする。
【0154】
実施例46〜47
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスC−1/A−1への添加>
実施例7の方法で得られた液晶配向剤ワニスC−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例46では0.0060g、実施例47では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例46ではC−2/A−2、実施例47ではC−3/A−3とする。
【0155】
実施例48〜49
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスC−1/A−1への添加>
実施例7の方法で得られた液晶配向剤ワニスC−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Mを実施例48では0.0060g、実施例49では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例48ではC−4/A−4、実施例49でC−5/A−5とする。
【0156】
実施例50〜51
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスC−1/A−1への添加>
実施例7の方法で得られた液晶配向剤ワニスC−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Xを実施例50では0.0060g、実施例51では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例50ではC−6/A−6、実施例51ではC−7/A−7とする。
【0157】
実施例52〜53
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスD−1/A−1への添加>
実施例8の方法で得られた液晶配向剤ワニスD−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例52では0.0060g、実施例53では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例52ではD−2/A−2、実施例53ではD−3/A−3とする。
【0158】
実施例54〜55
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスD−1/A−1への添加>
実施例8の方法で得られた液晶配向剤ワニスD−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Mを実施例54では0.0060g、実施例55では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例54ではD−4/A−4、実施例55でD−5/A−5とする。
【0159】
実施例56〜57
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスD−1/A−1への添加>
実施例8の方法で得られた液晶配向剤ワニスD−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Xを実施例56では0.0060g、実施例57では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例56ではD−6/A−6、実施例57ではD−7/A−7とする。
【0160】
実施例58〜59
<アルケニル置換ナジイミド化合物:BANI−Hの液晶配向剤ワニスE−1/A−1への添加>
実施例9の方法で得られた液晶配向剤ワニスE−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Hを実施例58では0.0060g、実施例59では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例58ではE−2/A−2、実施例59はE−3/A−3とする。
【0161】
実施例60〜61
<アルケニル置換ナジイミド化合物:BANI−Mの液晶配向剤ワニスE−1/A−1への添加>
実施例9の方法で得られた液晶配向剤ワニスE−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Mを実施例60では0.0060g、実施例61では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例60ではE−4/A−4、実施例61でE−5/A−5とする。
【0162】
実施例62〜63
<アルケニル置換ナジイミド化合物:BANI−Xの液晶配向剤ワニスE−1/A−1への添加>
実施例9の方法で得られた液晶配向剤ワニスE−1/A−1を10.0gとり、アルケニル置換ナジイミド化合物としてBANI−Xを実施例62では0.0060g、実施例63では0.0600gをそれぞれNMP10gに溶解させてから添加し、室温で1時間攪拌混合した。これらの液晶配向剤ワニスを実施例62ではE−6/A−6、実施例63ではE−7/A−7とする。
【0163】
実施例1〜63の液晶配向剤ワニスの調整例を表1にまとめる。
【0164】
【表1】
【0165】
実施例64
ラビングによるスジ・傷の評価および液晶配向性の評価(液晶配向性、プレチルト角測定用セルの作成)
実施例10で得られた液晶配向剤ワニスA−2をNMP−BC混合溶剤(重量比1/1)で希釈して、液晶配向剤ワニス中のポリマー成分濃度が3重量%となるように調整し、塗布用液晶配向剤ワニスとした。この希釈ワニスを透明電極付基板上にスピンナーにて塗布し、80℃にて約5分間予備焼成した。次いで、210℃にて30分間焼成して膜厚60nmの配向膜を形成し、その表面を全面にわたって、ラビングすることにより配向処理を行った。これと同じ基板をもう1枚用意し、片方の基板の配向膜面上に20μmのギャップ材を散布し、もう一方の基板を、配向膜面が向き合うように重ねてからエポキシ硬化剤でシールして、ギャップ20μmのアンチパラレルセルを作成した。
このセルに下記に示す誘電率異方性が正である液晶組成物−1を注入し、注入口を光硬化剤で封止した。次いで、110℃で30分間加熱処理を行い、ホモジニアス配向させたセルを作製した。このセルをクロスニコル状態に配置した2枚の偏光板ではさみ、その中で回転したところ、ラビングにより配向膜に生じた傷による配向欠陥(以下、スジや傷と称する)のない均一で明瞭な明暗が認められ、ラビングによって液晶分子が良好に配向していることが確認された。このセルのプレチルト角をクリスタルローテーション法によって測定したところ1.0°であった。
【0166】
液晶組成物−1
【化13】
【0167】
電圧保持率評価用セルの作製と測定
実施例10における評価用セルにおいて、ギャップ剤として7μmに変えた以外はプレチルト角測定用セルと同様にしてアンチパラレルセルを作製し、電圧保持率評価用のセルとした。電圧保持率は30Hzでは、98.5%、0.3Hzでは93.3%であった。また、Vthムラは全く観察されなかった。
【0168】
密着性の評価
実施例10で用いた液晶配向剤ワニスA−1を基板上にスピンナーで塗布したこと以外は液晶セル作成の焼成条件と同様の条件で焼成を行った。密着性をJIS K5400 8.5.2の碁盤目テープ法準拠して評価したところ、液晶配向膜の基板からの剥れは確認されなかった(○:100/100)。
【0169】
表面硬度の評価
実施例10で用いた液晶配向剤ワニスA−1を透明電極付き基板上に膜厚1μmとなるようにスピンナーで塗布したこと以外は、液晶セル作成の焼成条件と同様の条件で焼成を行った。この透明電極付き基板上に作成された液晶配向膜の表面硬度の測定を行ったところ、63.5(mgf/μm2)であった。
【0170】
実施例65〜117
他の液晶配向剤ワニスについても、実施例64と同様にしてプレチルト角測定用セル、電圧保持率評価用のセルを作製し、プレチルト角、液晶の配向性、表示不良、電圧保持率、表示ムラを評価した。なお、実施例76〜81および実施例100〜105は、下記に示す誘電率異方性が負の液晶組成物を液晶セルに注入した以外は実施例64と同様にしてプレチルト角、液晶の配向性、表示不良、電圧保持率、表示ムラを評価した。また、密着性、表面硬度も実施例64と同様にして評価を行った。結果を表2および表3にまとめる。
【0171】
液晶組成物―2
【化14】
【0172】
比較例1〜9
実施例1〜9で調整したアルケニル置換ナジイミド化合物を添加しない液晶配向剤ワニス、A−1、B−1、C−1,D−1、E−1、B−1/A−1、C−1/A−1、D−1/A−1およびE−1/A−1を用いた以外は、実施例64と同様にしてプレチルト角測定用セル、電圧保持率評価用のセルを作製し、プレチルト角、液晶の配向性、表示不良、電圧保持率、表示ムラを評価した。なお、比較例3および7は、実施例76、実施例100と同一の誘電率異方性が負の液晶組成物を液晶セルに注入した以外は、プレチルト角、液晶の配向性、表示不良、電圧保持率、表示ムラを同様に評価した。また、密着性、表面硬度も実施例64と同様にして評価を行った。結果を表2および表3にまとめる。
【0173】
【表2】
【0174】
【表3】
【0175】
表2および表3中、ラビングによるスジや傷に関する評価、および表示ムラに関する○印はスジや傷、表示ムラがほとんど認められないものを示し、×印はスジや傷、表示ムラが認められ実用に際して問題であることを示す。また、密着性に関する評価も同様に○印は実用に際して有用であり、×印は問題であることを示す。
【0176】
表2および表3の結果から、アルケニル置換ナジイミド化合物を添加した液晶配向剤ワニスより形成される液晶配向膜は、ラビングによるスジや傷のない均一で明瞭な明暗がとれる良好な液晶配向性を示すことが分かる。一方、アルケニル置換ナジイミド化合物を添加しない液晶配向剤ワニスより形成される液晶配向膜はラビング方向に顕著なスジ、傷が認められた。また液晶の配向性も乱れてしまうことが分かる。
【0177】
これらの結果から、アルケニル置換ナジイミド化合物を添加した液晶配向剤ワニスより形成される液晶配向膜は、アルケニル置換ナジイミド化合物を添加しない液晶配向剤ワニスより形成される液晶配向膜と比べてラビングによる削れ傷等が低減したことにより、電圧保持率が向上していることが分かる。
【0178】
基板との密着性の評価
表2および表3の結果から、アルケニル置換ナジイミド化合物を添加する液晶配向剤ワニスより形成される液晶配向膜は、アルケニル置換ナジイミド化合物を添加しない液晶配向剤ワニスより形成される液晶配向膜と比べて良好な密着性を示すことが分かる。
【0179】
配向膜の押しこみ硬度の評価
表2および表3の結果から、アルケニル置換ナジイミド化合物を添加した液晶配向剤ワニスより形成される液晶配向膜は、アルケニル置換ナジイミド化合物を添加しない液晶配向剤ワニスより形成される液晶配向膜と比べて高い表面硬度を有していることが分かる。
【0180】
表2および表3の結果によると、プレチルト角1.0〜89.5°を示す液晶配向膜において、ラビング傷や削れに関するアルケニル置換ナジイミド化合物の添加効果が確認された。従って、TN型液晶表示素子、STN型液晶表示素子、TN−TFT型液晶表示素子、IPS型液晶表示素子、VA型液晶表示素子、OCB型液晶表示素子、強誘電性液晶表示素子、反強誘電性液晶表示素子など様々なタイプの液晶表示素子において本発明の効果が認められることが分かった。
【0181】
【発明の効果】
本発明のアルケニル置換ナジイミド化合物を添加した液晶配向剤ワニスから形成された液晶配向膜を用いることによって液晶配向膜の機械的強度を向上させ、その結果、ラビング操作による配向膜上のスジや傷を防止するという効果が得られる。即ち、本発明によればより高性能なTN型液晶表示素子、STN型液晶表示素子、TN−TFT型液晶表示素子、IPS型液晶表示素子、VA型液晶表示素子、OCB型液晶表示素子、強誘電性液晶表示素子、反強誘電性液晶表示素子を実現することができる。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention is a varnish containing a polyamic acid, a soluble polyimide, a polyamide, a polyamideimide, or a polymer component of two or more of these, an alkenyl-substituted nadimide compound is added to an aligning agent varnish, and the varnish is coated on a substrate. The present invention relates to an alignment film formed by treating the surface by mechanical or physical contact after baking, and a liquid crystal display device having the alignment film, which has high display quality and excellent reliability.
[0002]
[Prior art]
A resin composition containing an alkenyl-substituted nadimide compound as one of the constituent components is disclosed in, for example, Patent Documents 1 and 2 below. However, the resin composition disclosed in the document mainly relates to a resin composition for a color filter protective film, and is essentially different from the resin composition for improving the display quality of the alignment film of the present invention.
Patent Document 3 discloses an example of a photo-alignment material and a photo-alignment film containing an alkenyl-substituted nadiimide compound. The photo-alignment material disclosed herein is a multi-functional maleimide derivative, and an alkenyl-substituted nadiimide derivative.Originally, a photo-alignment film that performs a non-contact type surface treatment using light without performing surface treatment by mechanical contact such as rubbing treatment. It is intended to be used as. In other words, it is not used for preventing the occurrence of rubbing streaks or scratches in a contact type surface orientation treatment involving mechanical or physical contact as in the present invention, that is, rubbing in a rubbing treatment. There is no description or suggestion about improvement of problems such as generation of streaks or scratches, which is essentially different from the present invention.
[0003]
Conventionally, flat displays using liquid crystal display elements have been widely used in watches, televisions, and the like. As a liquid crystal display element used in these liquid crystal displays, a display element using a nematic liquid crystal is mainstream, and a TN type liquid crystal display element twisted by 90 °, an STN type liquid crystal display element twisted by 180 ° or more, and a thin film transistor are generally used. The so-called TN-TFT type liquid crystal display element used, and in recent years, a class of the TFT type liquid crystal display element, in-plane switching (In-Plane Switching, hereinafter abbreviated as "IPS") of an in-plane switching method with improved visual characteristics. ) -Type liquid crystal display device (see Non-Patent Document 1), Vertical Alignment (Vertical Alignment, hereinafter abbreviated as “VA”) using a vertical alignment state (Non-Patent Document 2). Or extremely fast response speed and a relatively wide viewing angle An optically compensated birefringence (hereinafter abbreviated as “OCB”) type liquid crystal display element (see Non-Patent Document 3) has been proposed.
[0004]
[Patent Document 1]
JP-A-9-325210
[Patent Document 2]
JP-A-10-204126
[Patent Document 3]
JP-A-2002-265541
[Non-patent document 1]
Illustrations / Illustrations A book that understands the structure of liquid crystals Published by Technology Review Co., Ltd. p. 159 (1999)
[Non-patent document 2]
Illustrations / Illustrations A book that understands the structure of liquid crystals Published by Technology Review Co., Ltd. p. 146-150, 160 (1999)
[Non-Patent Document 3]
Illustrations / Illustrations A book that understands the structure of liquid crystals Published by Technology Review Co., Ltd. p. 184-185 (1999)
[0005]
In these liquid crystal display devices, it is important that the major axis direction of the liquid crystal molecules is uniformly aligned. The following rubbing method is known as a typical industrial method for uniformly aligning liquid crystal molecules in this manner. That is, an alignment film made of an organic film is provided on the substrate surface, the surface is rubbed (rubbed) in a certain direction with a cloth of cotton, nylon, polyester or the like, and the liquid crystal molecules are aligned in the rubbing direction. This rubbing method is industrially mainstream because stable uniform orientation can be obtained relatively easily and productivity is excellent. As a material for the alignment film, for example, polymers such as polyvinyl alcohol, polyoxyethylene, polyamide, polyimide, and polyamideimide are known, but from the viewpoint of stability and durability that can withstand industrial mass production, polyimide is chemically It is most often used as an aligning agent varnish polymer because of its excellent thermal stability.
[0006]
[Problems to be solved by the invention]
The alignment treatment method of rubbing the alignment film is simple and excellent in productivity, and is an industrially useful method.However, as the liquid crystal display device is used in various fields, various methods are required due to the high performance of the liquid crystal display device. Problems have begun to be pointed out. For example, it has been pointed out that scratches on the surface of the alignment film caused by rubbing appear as alignment defects, and that the alignment film is shaved off by rubbing and shavings and the like become display defects. Defects due to such rubbing have become one of the most significant factors for a decrease in yield, such as a defect in the presence of at least one defect in the screen with the recent enlargement of the screen. Rubbing resistance is required. Further, in recent years, attempts have been made to burn a liquid crystal aligning agent varnish at a low temperature of less than 200 ° C. using a plastic film instead of a conventional glass substrate in order to reduce the manufacturing cost or reduce the weight. However, especially when a polyamic acid, which is a precursor of polyimide, is applied on a substrate and baked at a low temperature, the dehydration ring closure (imidization) of the polyamic acid does not sufficiently proceed, and the resulting polyimide has an alignment film due to insufficient mechanical strength. Problems such as scratches are becoming more serious.
[0007]
Various problems related to these rubbing methods are caused by insufficient mechanical strength to cope with rubbing friction because the alignment film is a polymer, or insufficient adhesiveness with a glass substrate or the like. As a result, the alignment film is peeled off from the glass substrate, and development of an alignment film in which these are improved is desired. The mechanical strength can be improved to some extent by changing the molecular structure of the alignment film.However, the electrical characteristics of the alignment film and the pretilt angle of the liquid crystal tend to fluctuate by changing the structure. Because of this, it was very difficult to improve. In addition, although the adhesion to the glass substrate can be improved to some extent by using a coupling agent, the coupling agent is susceptible to hydrolysis and the like, and has a problem in storage stability as an alignment agent varnish, Further, when used excessively to prevent peeling, the performance of the liquid crystal display element is deteriorated.
[0008]
[Means for Solving the Problems]
The present inventors have intensively studied to solve these problems. As a result, when the alkenyl-substituted nadiimide is added to the liquid crystal aligning agent varnish, the liquid crystal aligning film obtained from the liquid crystal aligning agent varnish has a high mechanical strength, and has improved adhesion to a glass substrate, and has high resistance to rubbing. It has been found that a liquid crystal aligning film can be obtained, and a liquid crystal aligning agent varnish having further excellent storage stability can be obtained. Since the alkenyl-substituted nadimide compound derivative of the present invention contains an imide bonding group in the molecular skeleton, it has extremely good compatibility with the aligning agent varnish polymer component, and there is no site where hydrolysis occurs. Unlike coupling agents that have been used, there is no problem in storage stability as an aligning agent varnish. Furthermore, there is no adverse effect on the display performance and the like of the liquid crystal display element due to excessive use for preventing peeling. In addition, since it has a crosslinkable group in the molecule, when it is used in the form of a thin film such as an alignment film, the curing by crosslinking proceeds with heating for a relatively short time, the surface hardness increases, and the glass substrate is hardened. The inventors have found that the adhesion is also dramatically improved, and based on these findings, completed the present invention.
[0009]
The present invention includes the following items (1) to (9).
(1) A liquid crystal aligning agent varnish obtained by further adding an alkenyl-substituted nadimide compound to a varnish containing a polyamic acid, a soluble polyimide, a polyamide, a polyamideimide, or two or more of these polymer components.
[0010]
(2) The liquid crystal aligning agent varnish according to (1), wherein the polymer component is one or more polyamic acids.
(3) The liquid crystal aligning agent varnish according to (1), wherein the polymer component is one or more soluble polyimides.
(4) The liquid crystal aligning agent varnish according to (1), wherein the polymer component is one or more polyamides.
(5) The liquid crystal aligning agent varnish according to (1), wherein the polymer component is one or more polyamideimides.
[0011]
(6) The liquid crystal aligning agent varnish according to the above (1), wherein the alkenyl-substituted nadimide compound is a compound represented by the following formula (1).
[0012]
Embedded image
Where R1And R2Each independently represents a hydrogen atom, alkyl having 1 to 12 carbons, alkenyl having 3 to 6 carbons, cycloalkyl having 5 to 8 carbons, aryl, or benzyl, and n is an integer of 1 to 2 And when n = 1, R3Is alkyl having 1 to 12 carbons, cycloalkyl having 5 to 8 carbons, aryl having 6 to 12 carbons, benzyl,-ベ ン ジ ル (CqH2q) Ot(CrH2rO)uCsH2s + 1(Where q, r, and s are independently selected integers of 2 to 6, t is an integer of 0 or 1, and u is an integer of 1 to 30), R)a-C6H4-R4(Where a is an integer of 0 or 1, R is alkylene having 1 to 4 carbon atoms, R4Represents a hydrogen atom or an alkyl having 1 to 4 carbon atoms), a group represented by -C6H4-TC6H5Twhere T is -CH2-, -C (CH3)2-, -CO-, -S- or -SO2-Is a group represented by}, or a group in which 1 to 3 hydrogen atoms directly bonded to an aromatic ring of these groups are substituted with a hydroxyl group;3Is -CpH2p-(Where p is an integer of 2 to 20) alkylene, cycloalkylene having 5 to 8 carbon atoms,-{(CqH2qO)t(CrH2rO)uCsH2sPolyoxyalkylene represented by}-(where q, r, and s are each independently an integer of 2 to 6, t is an integer of 0 or 1 and u is an integer of 1 to 30), and has 6 carbon atoms. -12 arylene,-(R)a-C6H4-R5-(Where a is an integer of 0 or 1, R and R5Is an alkylene having 1 to 4 carbon atoms, at least one of which is independently selected);6H4-TC6H4-{Where T is -CH2-, -C (CH3)2-, -CO-, -O-, -OC6H4C (CH3)2C6H4O-, -S-, -SO2A group represented by-}, or a group in which 1 to 3 hydrogen atoms directly bonded to an aromatic ring of these groups are substituted with a hydroxyl group.
[0013]
(7) The above item (1) or (6), wherein the alkenyl-substituted nadimide compound is added in an amount of 0.01 to 50 parts by weight based on 100 parts by weight of the polymer component in the liquid crystal aligning agent varnish. Liquid crystal aligning agent varnish according to 3.
[0014]
(8) After applying the liquid crystal aligning agent varnish as described in any one of the above items (1) to (7) on a substrate, baking and then applying mechanical or physical contact to the surface. An alignment film formed by the treatment.
(9) A liquid crystal display device containing the alignment film according to the above (8).
[0015]
BEST MODE FOR CARRYING OUT THE INVENTION
The alkenyl-substituted nadimide compound used in the present invention will be described. Specific examples of the alkenyl-substituted nadimide compound include, for example,
[0016]
N-methyl-allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-methyl-allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-methyl-methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-methyl-methallylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (2-ethylhexyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
[0017]
N- (2-ethylhexyl) -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-allyl-allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-allyl-allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-allyl-methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-isopropenyl-allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-isopropenyl-allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-isopropenyl-methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-cyclohexyl-allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-cyclohexyl-allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-cyclohexyl-methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-phenyl-allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
[0018]
N-phenyl-allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-benzyl-allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-benzyl-allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N-benzyl-methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (2'-hydroxyethyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (2'-hydroxyethyl) -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (2'-hydroxyethyl) -methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
[0019]
N- (2 ', 2'-dimethyl-3'-hydroxypropyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (2 ', 2'-dimethyl-3'-hydroxypropyl) -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (2 ', 3'-dihydroxypropyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (2 ', 3'-dihydroxypropyl) -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (3'-hydroxy-1'-propenyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (4'-hydroxy-cyclohexyl) -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
[0020]
N- (4'-hydroxyphenyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (4'-hydroxyphenyl) -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (4'-hydroxyphenyl) -methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (4'-hydroxyphenyl) -methallylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (3'-hydroxyphenyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (3'-hydroxyphenyl) -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- (p-hydroxybenzyl) -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- {2 '-(2'-hydroxyethoxy) ethyl} -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
[0021]
N- {2 '-(2'-hydroxyethoxy) ethyl} -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- {2 '-(2'-hydroxyethoxy) ethyl} -methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- {2 '-(2'-hydroxyethoxy) ethyl} -methallylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- [2 '-{2'-(2 "-hydroxyethoxy) ethoxy} ethyl] -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- [2 '-{2'-(2 "-hydroxyethoxy) ethoxy} ethyl] -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- [2 '-{2'-(2 "-hydroxyethoxy) ethoxy} ethyl] -methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- {4 '-(4'-hydroxyphenylisopropylidene) phenyl} -allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- {4 '-(4'-hydroxyphenylisopropylidene) phenyl} -allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide;
N- {4 ′-(4′-hydroxyphenylisopropylidene) phenyl} -methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, and oligomers thereof. .
[0022]
Also,
N, N'-ethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-ethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-ethylene-bis (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-trimethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-hexamethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-hexamethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-dodecamethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-dodecamethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-cyclohexylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-cyclohexylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
[0023]
1,2-bis {3 '-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) propoxy} ethane,
1,2-bis {3 '-(allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) propoxy} ethane,
1,2-bis {3 '-(methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) propoxy} ethane,
Bis [2 '-{3'-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) propoxy} ethyl] ether,
Bis [2 '-{3'-(allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) propoxy} ethyl] ether,
1,4-bis {3 '-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) propoxy} butane,
1,4-bis {3 '-(allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) propoxy} butane,
[0024]
N, N'-p-phenylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-phenylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-phenylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-phenylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N '-{(1-methyl) -2,4-phenylene} -bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-xylylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-xylylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
[0025]
2,2-bis [4 '-{4'-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
2,2-bis [4 '-{4'-(allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
2,2-bis [4 '-{4'-(methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
Bis {4- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
[0026]
Bis {4- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (methallylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} ether,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} ether,
Bis {4- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} ether,
Bis {4- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} sulfone,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} sulfone,
[0027]
Bis {4- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} sulfone,
1,6-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) -3-hydroxy-hexane,
1,12-bis (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) -3,6-dihydroxy-dodecane,
1,3-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) -5-hydroxy-cyclohexane,
1,5-bis {3 '-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) propoxy} -3-hydroxy-pentane,
1,4-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) -2-hydroxy-benzene,
[0028]
1,4-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) -2,5-dihydroxy-benzene,
N, N'-p- (2-hydroxy) xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p- (2-hydroxy) xylylene-bis (allylmethylcyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m- (2-hydroxy) xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m- (2-hydroxy) xylylene-bis (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p- (2,3-dihydroxy) xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
[0029]
2,2-bis [4 '-{4'-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) -2'-hydroxy-phenoxy} phenyl] propane,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) -2-hydroxy-phenyl} methane,
Bis {3- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -4-hydroxy-phenyl} ether,
Bis {3- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -5-hydroxy-phenyl} sulfone,
1,1,1-tri {4 '-(allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide)} phenoxymethylpropane,
N, N ', N "-tri (ethylene methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) isocyanurate;
And oligomers thereof.
[0030]
Further, the following compounds containing an asymmetric alkylene phenylene group may be used.
[0031]
Embedded image
[0032]
Further, these alkenyl-substituted nadimide compounds may be used alone or as a mixture thereof.
[0033]
Preferred as the above alkenyl-substituted nadimide compound is
N, N'-ethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-ethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-ethylene-bis (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-trimethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-hexamethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-hexamethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-dodecamethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-dodecamethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-cyclohexylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-cyclohexylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
[0034]
N, N'-p-phenylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-phenylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-phenylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-phenylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N '-{(1-methyl) -2,4-phenylene} -bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-xylylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-xylylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
2,2-bis [4 '-{4'-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
2,2-bis [4 '-{4'-(allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
2,2-bis [4 '-{4'-(methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
Bis {4- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
[0035]
Bis {4- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (methallylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} ether,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} ether,
Bis {4- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} ether,
Bis {4- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} sulfone,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} sulfone,
[0036]
Bis {4- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} sulfone,
More preferred alkenyl-substituted nadimide compounds are
N, N'-ethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-ethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-ethylene-bis (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-trimethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-hexamethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-hexamethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-dodecamethylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-dodecamethylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-cyclohexylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-cyclohexylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
[0037]
N, N'-p-phenylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-phenylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-phenylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-phenylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N '-{(1-methyl) -2,4-phenylene} -bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-p-xylylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-xylylene-bis (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
N, N'-m-xylylene-bis (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide),
[0038]
2,2-bis [4 '-{4'-(allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
2,2-bis [4 '-{4'-(allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
2,2-bis [4 '-{4'-(methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide) phenoxy} phenyl] propane,
Bis {4- (allylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (allylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
[0039]
Bis {4- (methallylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
Bis {4- (methallylmethylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) phenyl} methane,
And the like.
[0040]
The liquid crystal aligning agent varnish of the present invention is a varnish composition in which a polymer component composed of a polyamic acid, a soluble polyimide, a polyamide, a polyamide imide or a mixture of two or more thereof is dissolved in a solvent, and further an alkenyl-substituted nadimide compound is added. The alkenyl-substituted nadimide compound is added in an amount of 0.01 to 50.0 parts by weight, preferably 0.1 to 30.0 parts by weight, based on 100 parts by weight of the polymer component. More preferably, it is 0.3 to 10.0 parts by weight. When the addition amount of the alkenyl-substituted nadimide compound of the present invention is within these ranges, a liquid crystal aligning agent varnish in which the balance among rubbing resistance, liquid crystal alignment, and display quality is maintained can be obtained.
[0041]
The effect of preventing rubbing of the liquid crystal alignment film by rubbing as defined in the present invention includes the effect of preventing the liquid crystal alignment film from peeling off from the substrate (the effect of improving the adhesion) and the effect of increasing the surface hardness of the liquid crystal alignment film from rubbing scratches. Refers to the reduction effect.
[0042]
According to the experiments of the present inventors, scratches due to rubbing of the liquid crystal alignment film are related to the adhesion between the substrate and the liquid crystal alignment film and the surface hardness. That is, if the adhesiveness between the liquid crystal alignment film and the substrate becomes stronger, the separation of the liquid crystal alignment film by rubbing can be prevented, and if the surface hardness becomes higher, the occurrence of rubbing scratches is reduced. Such a synergistic effect that the effect of preventing the separation of the liquid crystal alignment film and the effect of reducing the rubbing scratch affect each other can prevent the liquid crystal alignment film from being scraped by rubbing.
[0043]
The present inventors have focused on the surface hardness (indentation hardness) of the liquid crystal alignment film and, as a result, have determined that the surface hardness of the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide is obtained, which is obtained from the following equation, is obtained. Further, it was found that the rate of change of the surface hardness of the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which no alkenyl-substituted nadiimide was added was 101% or more, and the liquid crystal alignment film had high rubbing resistance.
[0044]
The surface hardness used in the present invention indicates an indentation hardness (H) defined by the following equation.
Indentation hardness (H) = kF / h2
(However, F: indentation load at the time of hardness evaluation (gf: gram weight), h: depth of recess (μm) formed when the test indenter is pushed into the test surface, k: constant determined by the shape of the indenter .)
k is a constant determined by the shape of the indenter, and the shape of the indenter used for the surface hardness measurement of the present invention is a triangular pyramid, and the angles between the edges are 65 °, 100 °, and 115 °. In the present invention, an indenter having an edge angle of 115 ° is used. In this case, k = 37.926.
[0045]
The thickness of the liquid crystal alignment film used for the surface hardness measurement is not particularly limited, but when the film thickness is small, the measured value is affected by the underlayer of the liquid crystal alignment film. Therefore, a preferable range of the film thickness for measuring the original surface hardness of the liquid crystal alignment film is 1 μm or more. For measuring the original surface hardness of the liquid crystal alignment film, the suitable range of the indentation depth is 1/3 or less, preferably 1/5 or less, more preferably 1/5 or less of the thickness of the liquid crystal alignment film. / 10 or less.
[0046]
In order to prevent scratches due to rubbing on the alignment film, from the viewpoint of both the adhesion to the substrate and the surface hardness, the amount of the alkenyl-substituted nadiimide compound is 0 to 100 parts by weight of the polymer component. A range of 0.3 to 10.0 parts by weight is particularly useful.
[0047]
The liquid crystal aligning agent varnish of the present invention is a varnish composition in which an alkenyl-substituted nadimide and a polymer component are dissolved in a solvent. The polymer component in the varnish may be a copolymer such as a random copolymer or a block copolymer, or a plurality of polymer components may be used in combination. The main component of the polymer is a polyamic acid obtained by reacting a tetracarboxylic dianhydride with a diamine, a soluble polyimide obtained by dehydrating the polyamic acid by a dehydration reaction or the like, and a ring-closed polyimide, a dicarboxylic acid or a derivative thereof. For example, a polyamide obtained by reacting a dicarboxylic acid dihalide with a diamine, a polyamide obtained by substituting a hydrogen atom of an amide bond (CONH) of the polyamide with another group, a diamine and a tetracarboxylic dianhydride and a dicarboxylic acid or a dicarboxylic acid or a dicarboxylic acid thereof A polyamide obtained by reacting a derivative or a polyamideimide obtained by reacting a diamine with trimellitic acid or a derivative thereof, and the like are preferably used.
[0048]
The above selection conditions for tetracarboxylic dianhydride are only capable of producing a polyamic acid by reacting with a diamine, and the conditions for selecting a dicarboxylic acid or dicarboxylic acid dihalide are to react with a diamine to form a polyamide. They can only be generated, and each has no other restrictions. Similarly, for diamines, it is only possible to react with tetracarboxylic dianhydride to produce polyamic acid, and to react with dicarboxylic acid or a derivative thereof to produce polyamide. Has no restrictions. Further, the use of two or more of these tetracarboxylic dianhydrides, dicarboxylic acids or derivatives thereof, and diamines is not limited at all.
[0049]
Specific examples of tetracarboxylic dianhydrides and diamines among acids and diamines as raw materials for polyamic acid or polyamide include, for example, WO 98 / 31725A1, WO 99 / 33902A1, WO 99 / 33923A1, WO 99 / 34252A1, and WO 01. Some of them are described in gazettes such as / 00732A1, and can be arbitrarily selected from those compounds and used. Further, specific examples of dicarboxylic acids are described in, for example, WO 01/14457 A1, and can be arbitrarily selected from those compounds and acid dihalides of these compounds.
[0050]
Specific examples include the following.
[0051]
Pyromellitic dianhydride,
3,3 ', 4,4'-diphenyltetracarboxylic dianhydride,
3,3 ', 4,4'-benzophenonetetracarboxylic dianhydride,
Naphthalene dianhydride (such as 2,3,6,7-naphthalene anhydride),
3,3 ', 4,4'-biphenylsulfonetetracarboxylic dianhydride,
3,3 ', 4,4'-biphenylethertetracarboxylic dianhydride,
3,3 ', 4,4'-dimethyldiphenylsilanetetracarboxylic dianhydride,
4,4'-bis (3,4-dicarboxyphenoxy) diphenyl sulfide dianhydride,
4,4'-bis (3,4-dicarboxyphenoxy) diphenylsulfone dianhydride,
4,4'-bis (3,4-dicarboxyphenoxy) diphenylpropane dianhydride,
3,3 ', 4,4'-per-fluoropyridene diphthalic dianhydride,
3,3 ', 4,4'-biphenyltetracarboxylic dianhydride,
Bis (phthalic acid) phenylsulfine oxide dianhydride,
p-phenylene-bis (triphenylphthalic acid) dianhydride,
m-phenylene-bis (triphenylphthalic acid) dianhydride,
Bis (triphenylphthalic acid) -4,4'-diphenylether dianhydride,
Bis (triphenylphthalic acid) -4,4'-diphenylmethane dianhydride and the like;
[0052]
Cyclobutanetetracarboxylic dianhydride,
Cyclopentanetetracarboxylic dianhydride,
Bicyclo [2.2.2] -oct-7-ene-2,3,5,6-tetracarboxylic dianhydride,
Cyclohexane-1,2,5,6-tetracarboxylic dianhydride,
3,3'-bicyclohexyl-1,1 ', 2,2'-tetracarboxylic dianhydride,
2,3,5-tricarboxycyclopentylacetic acid dianhydride,
5- (2,5-dioxotetrahydrofural) -3-methyl-3-cyclohexene-1,2-dicarboxylic dianhydride,
1,3,3a, 4,5,9b-Hexahydro-5-tetrahydro-2,5-dioxo-3-furanyl) -naphtho [1,2, -c] -furan-1,3-dione, 3,5 , 6-Tricarboxynorbornane-2-acetic acid dianhydride,
2,3,4,5-tetrahydrofurantetracarboxylic dianhydride,
Or a tetracarboxylic dianhydride partially substituted with a lower alkyl such as methyl or ethyl group,
[0053]
Ethylene tetracarboxylic dianhydride,
Butanetetracarboxylic dianhydride,
Pentanetetracarboxylic dianhydride,
Hexanetetracarboxylic dianhydride,
Heptanetetracarboxylic dianhydride and the like.
[0054]
The tetracarboxylic dianhydride according to the present invention is not limited to these, and various other acid dianhydrides may be used as long as the object of the present invention is achieved. These tetracarboxylic dianhydrides can be used alone or in combination of two or more.
[0055]
The following can be mentioned as specific examples of the dicarboxylic acid or its derivative that gives the polyamide of the present invention.
In the form of dicarboxylic acids, malonic acid, oxalic acid, dimethylmalonic acid, succinic acid, fumaric acid, glutaric acid, adipic acid, muconic acid, 2-methyladipic acid, trimethyladipic acid, pimelic acid, 2,2-dimethylglutaric acid , 3,3-diethylsuccinic acid, azelaic acid, sebacic acid and suberic acid, etc.
[0056]
1,1-cyclopropanedicarboxylic acid,
1,2-cyclopropanedicarboxylic acid,
1,1-cyclobutanedicarboxylic acid,
1,2-cyclobutanedicarboxylic acid,
1,3-cyclobutanedicarboxylic acid,
3,4-diphenyl-1,2-cyclobutanedicarboxylic acid,
2,4-diphenyl-1,3-cyclobutanedicarboxylic acid,
3,4-bis (2-hydroxyphenyl) -1,2-cyclobutanedicarboxylic acid,
2,4-bis (2-hydroxyphenyl) -1,3-cyclobutanedicarboxylic acid,
[0057]
1-cyclobutene-1,2-dicarboxylic acid,
1-cyclobutene-3,4-dicarboxylic acid,
1,1-cyclopentanedicarboxylic acid,
1,2-cyclopentanedicarboxylic acid,
1,3-cyclopentanedicarboxylic acid,
1,1-cyclohexanedicarboxylic acid,
1,2-cyclohexanedicarboxylic acid,
1,3-cyclohexanedicarboxylic acid,
1,4-cyclohexanedicarboxylic acid,
1,4- (2-norbornene) dicarboxylic acid,
[0058]
Norbornene-2,3-dicarboxylic acid,
Bicyclo [2.2.2] octane-1,4-dicarboxylic acid,
Bicyclo [2.2.2] octane-2,3-dicarboxylic acid,
2,5-dioxo-1,4-bicyclo [2.2.2] octanedicarboxylic acid,
1,3-adamantanedicarboxylic acid,
4,8-dioxo-1,3-adamantanedicarboxylic acid,
2,6-spiro [3.3] heptanedicarboxylic acid,
1,3-adamantane acetic acid,
Camphoric acid and the like.
[0059]
o-phthalic acid,
Isophthalic acid,
Terephthalic acid,
5-methylisophthalic acid,
5-tert-butyl isophthalic acid,
5-aminoisophthalic acid,
5-hydroxyisophthalic acid,
2,5-dimethylterephthalic acid,
Tetramethyl terephthalic acid,
[0060]
1,4-naphthalenedicarboxylic acid,
2,5-naphthalenedicarboxylic acid,
2,6-naphthalenedicarboxylic acid,
2,7-naphthalenedicarboxylic acid,
1,4-anthracene dicarboxylic acid,
1,4-anthraquinone dicarboxylic acid,
2,5-biphenyldicarboxylic acid,
4,4'-biphenyldicarboxylic acid,
1,5-biphenylenedicarboxylic acid,
4,4 "-tert-phenyldicarboxylic acid,
4,4'-diphenylmethanedicarboxylic acid,
4,4'-diphenylethanedicarboxylic acid,
4,4'-diphenylpropanedicarboxylic acid,
4,4'-diphenylhexafluoropropanedicarboxylic acid,
4,4'-diphenyl ether dicarboxylic acid,
4,4'-bibenzyldicarboxylic acid,
4,4'-stilbene dicarboxylic acid,
4,4'-trandicarboxylic acid,
4,4'-carbonyldibenzoic acid,
4,4'-sulfonyl dibenzoic acid,
4,4'-dithiodibenzoic acid,
[0061]
p-phenylene diacetate,
3,3'-p-phenylenedipropionic acid,
4-carboxycinnamic acid,
p-phenylenediacrylic acid,
3,3 '-[4,4'-(methylenedi-p-phenylene)] dipropionic acid,
4,4 '-[4,4'-(oxydi-p-phenylene)] dipropionic acid,
4,4 '-[4,4'-(oxydi-p-phenylene)] dibutyric acid,
(Isopropylidenedi-p-phenylenedioxy) dibutyric acid,
[0062]
Bis (p-carboxyphenyl) dimethylsilane,
1,5- (9-oxofluorene) dicarboxylic acid,
3,4-furandicarboxylic acid,
4,5-thiazoledicarboxylic acid,
2-phenyl-4,5-thiazoledicarboxylic acid,
1,2,5-thiadiazole-3,4-dicarboxylic acid,
1,2,5-oxadiazole-3,4-dicarboxylic acid,
2,3-pyridinedicarboxylic acid,
2,4-pyridinedicarboxylic acid,
2,5-pyridinedicarboxylic acid,
2,6-pyridinedicarboxylic acid,
3,4-pyridinedicarboxylic acid,
3,5-pyridinedicarboxylic acid,
Examples thereof include 3,6-pyridinedicarboxylic acid, and these dicarboxylic acids may be in the form of dicarboxylic acid halide.
[0063]
The dicarboxylic acid or dicarboxylic acid halide according to the present invention is not limited thereto, and other dicarboxylic acids or dicarboxylic acid halides can be used as long as the object of the present invention is achieved. These dicarboxylic acids or dicarboxylic acid halides can be used alone or in combination of two or more.
Furthermore, trimellitic acid or a derivative thereof, trimellitic chloride anhydride, is also useful as another acid component when synthesizing polyamideimide.
The following compounds are mentioned as a tetracarboxylic dianhydride used preferably.
[0064]
Embedded image
[0065]
Embedded image
[0066]
Embedded image
[0067]
Specific examples of the diamine used in the present invention include the following.
p-phenylenediamine,
m-phenylenediamine,
o-phenylenediamine,
p-xylenediamine,
m-xylenediamine,
p-xylylenediamine,
m-xylylenediamine,
2,4-diaminotoluene,
2,6-diaminotoluene,
2,3,5,6-tetramethyl-p-phenylenediamine,
2,5-dimethyl-p-phenylenediamine,
[0068]
3,3'-diaminodiphenylmethane,
4,4'-diaminodiphenylmethane,
3,3'-diaminodiphenylethane,
4,4'-diaminodiphenylethane,
1,3-bis (4-aminophenyl) propane,
2,2-bis (4-aminophenyl) propane,
2,2-bis (3-aminophenyl) propane,
2,2-bis (4-aminophenyl) perfluoropropane,
2,2-bis (3-aminophenyl) perfluoropropane,
[0069]
Bis (4-amino-3-methylphenyl) methane,
Bis (4-amino-2-methylphenyl) methane,
1,2-bis (4-amino-3-methylphenyl) ethane,
1,3-bis (4-amino-3-methylphenyl) propane,
1,2-bis (4-amino-2-methylphenyl) ethane,
1,3-bis (4-amino-2-methylphenyl) propane,
[0070]
1,4-bis [(4-aminophenyl) methyl] benzene,
1,4-bis [(3-aminophenyl) methyl] benzene,
1,4-bis [(4-aminophenyl) ethyl] benzene,
1,4-bis [(3-aminophenyl) ethyl] benzene,
1,4-bis [(4-amino-3-methyl-phenyl) methyl] benzene,
1,4-bis [(4-amino-3-methyl-phenyl) ethyl] benzene,
[0071]
Bis-[(4- (4-aminophenylmethyl) phenyl] methane,
Bis-[(4- (4-aminophenylmethyl) phenyl] ethane,
Bis-[(4- (3-aminophenylmethyl) phenyl] methane,
Bis-[(4- (3-aminophenylmethyl) phenyl] ethane,
2,2'-bis-[(4- (4-aminophenylmethyl) phenyl] propane,
2,2'-bis-[(4- (3-aminophenylmethyl) phenyl) propane,
2,2'-bis-[(4- (3-aminophenylmethyl) phenyl) perfluoropropane,
[0072]
1,4-bis (4-aminophenoxy) benzene,
1,3-bis (4-aminophenoxy) benzene,
2,2-bis (4-aminophenoxy) propane,
Bis [4- (4-aminophenoxy) phenyl] methane,
2,2-bis [4- (4-aminophenoxy) phenyl] ethane,
1,1-bis [4- (4-aminophenoxy) phenyl] propane,
2,2-bis [4- (4-aminophenoxy) phenyl] propane,
1,2-bis [4- (4-aminophenoxy) phenyl] propane,
2,2-bis [4- (2-aminophenoxy) phenyl] per-fluoropropane,
2,2-bis [4- (3-aminophenoxy) phenyl] per-fluoropropane,
2,2-bis [4- (4-aminophenoxy) phenyl] per-fluoropropane,
2,2-bis [4- (4-aminophenoxy) phenyl] butane,
[0073]
4,4'-diaminobiphenyl,
3,3'-dimethylbenzidine,
3,3'-dimethoxybenzidine,
1,4-bis (4-aminophenyl) benzene,
4,4'-bis (4-aminophenyl) biphenyl,
4,4'-diaminota-phenyl,
3,3'-dimethyl-4,4'-diaminobiphenyl,
1,3-bis [4- (4-aminophenoxy) phenyl] benzene,
1,4-bis [4- (4-aminophenoxy) phenyl] benzene,
4,4-bis [4- (4-aminophenoxy) phenyl] biphenyl,
1,2-bis [4- (4-aminophenoxy) phenyl] cyclohexane,
1,3-bis [4- (4-aminophenoxy) phenyl] cyclohexane,
1,4-bis [4- (4-aminophenoxy) phenyl] cyclohexane,
[0074]
1,5-diaminonaphthalene,
2,6-diaminonaphthalene,
2,7-diaminofluorene,
9,9-bis (4-aminophenyl) fluorene,
9,9-bis (4-aminophenyl) -10-anthracene,
4,4 '-(p-phenylenediisopropylidene) bisaniline,
4,4 '-(m-phenylenediisopropylidene) bisaniline,
4,4'-diaminobenzanilide,
3,3'-diaminobenzophenone,
3,4'-diaminobenzophenone,
4,4'-diaminobenzophenone,
3,3'-diaminodiphenylbenzophenone,
4,4'-bis (4-aminophenoxy) diphenyl ketone,
[0075]
3,3'-diaminodiphenyl sulfide,
4,4'-diaminodiphenyl sulfide,
Bis [4- (4-aminophenoxy) phenyl] sulfide,
3,3'-diaminodiphenyl sulfone,
4,4'-diaminodiphenyl sulfone,
Bis [4- (4-aminophenoxy) phenyl] sulfone,
3,3'-diaminodiphenyl ether,
4,4'-diaminodiphenyl ether,
3,4'-diaminodiphenyl ether,
Bis- (4-aminophenyl) diethylsilane,
Bis- (4-aminophenyl) diphenylsilane,
Bis- (4-aminophenyl) ethylphosphine oxide,
[0076]
2,2-bis [4- (3-carbamoyl-4-aminophenoxy) phenyl] per-fluoropropane,
2,2-bis- (3-sulfamoyl-4-aminophenyl) per-fluoropropane,
2,2-bis- (3-carboxy-4-aminophenyl) per-fluoropropane,
2,2-bis [4- (3-sulfamoyl-4-aminophenoxy) phenyl] per-fluoropropane,
2,2-bis [4- (3-carboxy-4-aminophenoxy) phenyl] per-fluoropropane,
[0077]
1,3-bis [2- {4- (4-aminophenoxy) phenyl} per-fluoroisopropyl] benzene,
2,4-bis (β-amino-t-butyl) toluene,
Bis (p-β-methyl-γ-aminopentyl) benzene,
Bis-p- (1,1-dimethyl-5-aminopentyl) benzene,
Bis (p-β-amino-t-butylphenyl) ether;
Bis (4-aminobenzoyloxy) methane,
Bis (4-aminobenzoyloxy) ethane,
Bis (4-aminobenzoyloxy) propane,
Bis (4-aminobenzoyloxy) cyclohexane,
2,3-diaminopyridine,
2,6-diaminopyridine,
3,4-diaminopyridine,
2,4-diaminopyridine,
Diaminopyrimidine,
Diaminopiperazine,
Bis- (4-aminophenyl) -N-butylamine,
N, N-bis- (4-aminophenyl) -N-methylamine,
N- (3-aminophenyl) -4-aminobenzamide and the like.
[0078]
1,4-diaminocyclohexane,
1,3-bis (aminomethyl) cyclohexane,
1,4-bis (aminomethyl) cyclohexane,
Isophorone diamine,
Norbornanediamine,
4,4'-diaminodicyclohexylmethane,
Bis (2-methyl-4-aminocyclohexyl) methane,
Tetrahydrodicyclopentadienylenediamine,
Hexahydro-4,7-methanoindanylene dimethylene diamine,
Tricyclo [6.2.1.02,7]-Undecylenedimethyldiamine,
4,4'-methylenebis (cyclohexylamine),
[0079]
2,5-bis (aminomethyl) -bicycloheptane,
2,6-bisaminomethyl-bicycloheptane,
2,3-diaminobicyclo [2,2,1] heptane,
2,5-diaminobicyclo [2,2,1] heptane,
2,6-diaminobicyclo [2,2,1] heptane,
2,7-diaminobicyclo [2,2,1] heptane,
2,3-diamino-7-azabicyclo [2,2,1] heptane,
2,5-diamino-7-azabicyclo [2,2,1] heptane,
2,6-diamino-7-azabicyclo [2,2,1] heptane,
2,3-diamino-7-thiabicyclo [2,2,1] heptane,
2,5-diamino-7-thiabicyclo [2,2,1] heptane,
2,6-diamino-7-thiabicyclo [2,2,1] heptane,
2,3-diaminobicyclo [2,2,2] octane,
2,5-diaminobicyclo [2,2,2] octane,
2,6-diaminobicyclo [2,2,2] octane,
2,5-diaminobicyclo [2,2,2] octane-7-ene,
2,5-diamino-7-azabicyclo [2,2,2] octane,
2,5-diamino-7-oxabicyclo [2,2,2] octane,
2,5-diamino-7-thiabicyclo [2,2,2] octane,
2,6-diaminobicyclo [3,2,1] octane,
2,6-diaminoazabicyclo [3,2,1] octane,
2,6-diaminooxabicyclo [3,2,1] octane,
2,6-diaminothiabicyclo [3,2,1] octane,
2,6-diaminobicyclo [3,2,2] nonane,
2,6-diaminobicyclo [3,2,2] nonan-8-ene,
2,6-diamino-8-azabicyclo [3,2,2] nonane,
2,6-diamino-8-oxabicyclo [3,2,2] nonane,
2,6-diamino-8-thiabicyclo [3,2,2] nonane and the like.
[0080]
Aliphatic diamine compounds such as ethylenediamine, trimethylenediamine, propanediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, 4,4-diaminoheptamethylenediamine, and alkylene Alkylene diamines having an oxygen atom in the group.
[0081]
1,1-bis [4- (4-aminophenoxy) phenyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-methylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-ethylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-propylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-butylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-pentylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-hexylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-heptylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-octylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-nonylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-decylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-undecylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-dodecylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-tridecylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-tetradecylcyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-n-pentadecylcyclohexane,
[0082]
1,1-bis (4-aminophenyl) cyclohexane,
1,1-bis (4-aminophenyl) -4-methylcyclohexane,
1,1-bis (4-aminophenyl) -4-ethylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-propylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-butylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-pentylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-hexylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-heptylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-octylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-nonylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-decylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-undecylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-dodecylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-tridecylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-tetradecylcyclohexane,
1,1-bis (4-aminophenyl) -4-n-pentadecylcyclohexane,
[0083]
1,1-bis (4-aminophenyl) -4-cyclohexylcyclohexane,
1,1-bis (4-aminophenyl) -4- (4-methyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-ethyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-propyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-butyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-pentyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-hexyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-heptyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-octyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-nonyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-decyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-undecyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-dodecyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-tridecyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-tetradecyl-trans-cyclohexyl) cyclohexane,
1,1-bis (4-aminophenyl) -4- (4-n-pentadecyl-trans-cyclohexyl) cyclohexane,
[0084]
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (cyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-methylcyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-ethylcyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-propylcyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-butylcyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-pentylcyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-hexylcyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-heptylcyclohexyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-octylcyclohexyl) cyclohexane,
[0085]
1,1-bis (4-aminophenyl) -4- (cyclohexylmethyl) cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-methylcyclohexyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-ethylcyclohexyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-propylcyclohexyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-butylcyclohexyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-pentylcyclohexyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-hexylcyclohexyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-heptylcyclohexyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-octylcyclohexyl) methyl] cyclohexane,
[0086]
1,1-bis [4- (4-aminophenoxy) phenyl] -4- (phenylmethyl) cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl] -4-[(4-methylphenyl) methyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl) -4-[(4-ethylphenyl) methyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl) -4-[(4-propylphenyl) methyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl) -4-[(4-butylphenyl) methyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl) -4-[(4-pentylphenyl) methyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl) -4-[(4-hexylphenyl) methyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl) -4-[(4-heptylphenyl) methyl] cyclohexane,
1,1-bis [4- (4-aminophenoxy) phenyl) -4-[(4-octylphenyl) methyl] cyclohexane,
[0087]
1,1-bis (4-aminophenyl) -4- (phenylmethyl) cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-methylphenyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-ethylphenyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-propylphenyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-butylphenyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-pentylphenyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-hexylphenyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-heptylphenyl) methyl] cyclohexane,
1,1-bis (4-aminophenyl) -4-[(4-octylphenyl) methyl] cyclohexane,
[0088]
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- (phenylmethyl) cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-methylphenyl) methyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-ethylphenyl) methyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-propylphenyl) methyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-butylphenyl) methyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-pentylphenyl) methyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-hexylphenyl) methyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-heptylphenyl) methyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-[(4-octylphenyl) methyl] cyclohexane,
[0089]
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-methylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-ethylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-propylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-butylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-pentylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-hexylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-heptylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4-octylclohexane.
[0090]
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (cyclohexylethylcyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-methyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-ethyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-propyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-butyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-pentyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-amyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-hexyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-heptyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-octyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-nonyl-trans-cyclohexyl) ethyl] cyclohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} -4- [2- (4-dodecyl-trans-cyclohexyl) ethyl] cyclohexane,
[0091]
1,1-bis [4- (4-aminophenoxy) phenyl] pentane,
2,2-bis [4- (4-aminophenoxy) phenyl] pentane,
3,3-bis [4- (4-aminophenoxy) phenyl] pentane,
1,1-bis [4- (4-aminophenoxy) phenyl] hexane,
2,2-bis [4- (4-aminophenoxy) phenyl] hexane,
3,3-bis [4- (4-aminophenoxy) phenyl] hexane,
1,1-bis [4- (4-aminophenoxy) phenyl] heptane,
2,2-bis [4- (4-aminophenoxy) phenyl] heptane,
3,3-bis [4- (4-aminophenoxy) phenyl] heptane,
4,4-bis [4- (4-aminophenoxy) phenyl] heptane,
1,1-bis [4- (4-aminophenoxy) phenyl] octane,
2,2-bis [4- (4-aminophenoxy) phenyl] octane,
3,3-bis [4- (4-aminophenoxy) phenyl] octane,
4,4-bis [4- (4-aminophenoxy) phenyl] octane,
1,1-bis [4- (4-aminophenoxy) phenyl] nonane,
2,2-bis [4- (4-aminophenoxy) phenyl] nonane,
3,3-bis [4- (4-aminophenoxy) phenyl] nonane,
4,4-bis [4- (4-aminophenoxy) phenyl] nonane,
5,5-bis [4- (4-aminophenoxy) phenyl] nonane,
1,1-bis [4- (4-aminophenoxy) phenyl] decane,
2,2-bis [4- (4-aminophenoxy) phenyl] decane,
3,3-bis [4- (4-aminophenoxy) phenyl] decane,
4,4-bis [4- (4-aminophenoxy) phenyl] decane,
5,5-bis [4- (4-aminophenoxy) phenyl] decane,
2,2-bis [4- (4-aminophenoxy) phenyl] undecane,
2,2-bis [4- (4-aminophenoxy) phenyl] dodecane,
2,2-bis [4- (4-aminophenoxy) phenyl] tridecane,
2,2-bis [4- (4-aminophenoxy) phenyl] tetradecane,
2,2-bis [4- (4-aminophenoxy) phenyl] pentadecane,
2,2-bis [4- (4-aminophenoxy) phenyl] hexadecane,
2,2-bis [4- (4-aminophenoxy) phenyl] heptadecane,
2,2-bis [4- (4-aminophenoxy) phenyl] octadecane,
2,2-bis [4- (4-aminophenoxy) phenyl] nonadecane,
[0092]
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} pentane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} pentane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} pentane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} hexane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} hexane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} hexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} heptane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} heptane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} heptane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} heptane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} octane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} octane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} octane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} octane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} nonane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} nonane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} nonane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} nonane,
5,5-bis {4-[(4-aminophenyl) methyl] phenyl} nonane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} decane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} decane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} decane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} decane,
5,5-bis {4-[(4-aminophenyl) methyl] phenyl} decane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} undecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} dodecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} tridecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} tetradecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} pentadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} hexadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} heptadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} octadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} nonadecane,
[0093]
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} perfluoropentane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoropentane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoropentane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorohexane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorohexane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorohexane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoroheptane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoroheptane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoroheptane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoroheptane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorooctane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorooctane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorooctane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorooctane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorononane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorononane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorononane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorononane,
5,5-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorononane,
1,1-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorodecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorodecane,
3,3-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorodecane,
4,4-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorodecane,
5,5-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorodecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoroundecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorododecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorotridecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorotetradecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} perfluoropentadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorohexadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluoroheptadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} per-fluorooctadecane,
2,2-bis {4-[(4-aminophenyl) methyl] phenyl} perfluorononadecane and the like.
[0094]
4- [3- (4-biphenyloxy) propoxy] -1,3-diamine,
4- [8- (4-biphenyloxy) octyloxy] -1,3-diaminobenzene,
4- [3- (4-cyanobiphenyl-4'-oxy) propoxy] -1,3-diaminobenzene,
4- [12- (4-cyanobiphenyl-4'-oxy) dodecyloxy] -1,3-diaminobenzene,
4- [6- (4-methoxybiphenyl-4'-oxy) hexyloxy] -1,3-diaminobenzene,
4- [3- (4-fluorobiphenyl-4'-oxy) propoxy] -1,3-diaminobenzene,
[0095]
Dodecyl 2,4-diaminobenzoate,
Octyl 2,4-diaminobenzoate,
1,5-diamino-2-octyloxycarbonylaminobenzene,
1,4-diamino-3- [4- (4-alkylcyclohexyl) cyclohexyloxy] benzene,
1,4-diamino-3- [4- (4-alkylphenyl) cyclohexyloxy] benzene,
1,4-diamino-3-((4-alkylta-phenyl) oxy) benzene,
1,4-diamino- (2-alkyl) benzene,
1,4-diamino- (2,5-dialkyl) benzene,
2-alkyloxy-1,4-diaminobenzene and the like.
[0096]
1-cyclohexyl-4- (4-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-methylcyclohexyl) -4- (4-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-propylcyclohexyl) -4- (4-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-pentylcyclohexyl) -4- (4-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-octylcyclohexyl) -4- (4-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-decylcyclohexyl) -4- (4-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-dodecylcyclohexyl) -4- (4-aminobenzyl-2-aminophenyl) cyclohexane,
1-cyclohexyl-4- (3-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-methylcyclohexyl) -4- (3-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-propylcyclohexyl) -4- (3-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-pentylcyclohexyl) -4- (3-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-octylcyclohexyl) -4- (3-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-decylcyclohexyl) -4- (3-aminobenzyl-2-aminophenyl) cyclohexane,
1- (4-dodecylcyclohexyl) -4- (3-aminobenzyl-2-aminophenyl) cyclohexane and the like.
[0097]
In addition, cholesteryl, androsteryl, β-cholesteryl, epiandrosteryl, erygosteryl, estrol, 11α-hydroxymethylsteryl, 11α-progesteryl, lanosteryl, melatranil, methyltestosterol, norethisteryl, pregnenonyl, β-sitosteryl, stigmasteryl and testosteril. And diamines having a side chain of a steroid skeleton such as cholesterol acetate.
[0098]
Embedded image
[0099]
Embedded image
[0100]
In these formulas, R represents hydrogen or an alkyl group having 1 to 20 carbon atoms;2-May be replaced by -O-, -CH = CH- or -C≡C-. In addition, the diamine according to the present invention is not limited to these, and it goes without saying that other diamines can be used as long as the object of the present invention is achieved. These diamines can be used alone or in combination of two or more.
[0101]
Further, as other diamines that can be used in combination with the above-mentioned diamines according to the present invention, there can be mentioned siloxane-based diamines containing siloxane bonds. The siloxane-based diamine is not particularly limited, but those represented by the formula (3) can be preferably used in the present invention.
[0102]
Embedded image
(In the formula (3), R2And R3Is independently alkyl having 1 to 3 carbons or phenyl. Also, R4Is methylene, phenylene or alkyl-substituted phenylene. x represents an integer of 1 to 6, and y represents an integer of 1 to 10).
[0103]
In addition, as a raw material of the above-mentioned polyamic acid or polyamide, it is also possible to use a monoamine compound or / and a monocarboxylic anhydride for forming these reaction terminals in combination.
[0104]
Furthermore, if an organosilicon compound or a titanium-based coupling agent is added to the liquid crystal aligning agent varnish of the present invention, the adhesion of the alignment film formed using the liquid crystal aligning agent varnish of the present invention to a glass substrate is further improved. Is done. Although the organosilicon compound is not particularly limited, for example, aminopropyltrimethoxysilane, aminopropyltriethoxysilane, vinyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N -(2-aminoethyl) -3-aminopropyltrimethoxysilane, vinyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, Examples thereof include silane coupling agents such as 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane and silicone oils such as polydimethylsiloxane and polydiphenylsiloxane.
[0105]
The addition ratio of the organosilicon compound or the titanium-based coupling agent to the liquid crystal aligning agent varnish is not particularly limited, but is 0.01 to 5 parts by weight based on 100 parts by weight of the polymer component contained in the liquid crystal aligning agent varnish. Parts, preferably 0.1 to 3 parts by weight.
[0106]
The polymer component concentration in the liquid crystal aligning agent varnish of the present invention is preferably 0.1 to 40% by weight. When the concentration of the polymer component is within this range, a liquid crystal aligning agent varnish having an appropriate viscosity can be obtained, and the varnish can be easily diluted and adjusted to an optimum film thickness. In the case of a spinner method or a printing method, the content is usually set to 10% by weight or less in order to keep a good film thickness. In other coating methods, for example, a dipping method, the concentration may be even lower. The content is 0.1% by weight or more, preferably 0.5 to 10% by weight in a usual spinner method or printing method. However, depending on the method of applying the liquid crystal aligning agent varnish, a more dilute concentration may be used.
[0107]
The solvent used together with the polymer component in the liquid crystal aligning agent varnish of the present invention is only a condition that has the ability to dissolve various polymer components and alkenyl-substituted nadimide compounds, and there is no particular limitation. Therefore, a solvent according to the purpose may be appropriately selected from solvents commonly used in the respective production steps and applications of polyamic acid, soluble polyimide, polyamide, and polyamideimide. Examples of these solvents include aprotic polar organic solvents that are good solvents for polyamic acids, soluble polyimides, polyamides, and polyamideimides, for example, N-methyl-2-pyrrolidone (hereinafter abbreviated as NMP), dimethyl. Imidazolidinone, N-methylcaprolactam, N-methylpropionamide, N, N-dimethylacetamide (DMAc), dimethylsulfoxide (DMSO), N, N-dimethylformamide (DMF), diethylacetamide or γ-butyllactone ( GBL).
[0108]
Other solvents that are good solvents for alkenyl-substituted nadimides include methanol, ethanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran, 1,4-dioxane, methyl acetate, vinyl acetate, chloroform, chlorobenzene, toluene, Examples thereof include xylene, cresol, acetonitrile, pyridine, and ethylene glycol dimethyl ether.
[0109]
In addition, other solvents for the purpose of improving coating properties, for example, alkyl lactate, ethylene glycol monoalkyl such as 3-methyl-3-methoxybutanol, tetralin, isophorone, ethylene glycol monobutyl ether (hereinafter abbreviated as BC) and the like. Ether, diethylene glycol monoalkyl ether such as diethylene glycol monoethyl ether, ethylene glycol monoalkyl or phenyl acetate, triethylene glycol monoalkyl ether, propylene glycol monoalkyl ether such as propylene glycol monobutyl ether, dialkyl malonate such as diethyl malonate, Dipropylene glycol monoalkyl ethers such as propylene glycol monomethyl ether or ester compounds such as acetates thereof Solvent and the like can also be mentioned. In the present invention, the solvent may be a mixed solvent.
[0110]
The liquid crystal aligning agent varnish of the present invention can contain various additives as necessary. For example, if it is desired to improve the coating properties and the antistatic property, a surfactant for such a purpose may be blended, and as long as the properties of the alignment film are not impaired, an anionic surfactant and a cationic surfactant may be used. A surfactant, an amphoteric surfactant and a nonionic surfactant may be blended.
[0111]
The alignment film of the present invention can be used for any liquid crystal display device, and the effect of the present invention is exhibited in any liquid crystal display device. Among them, modes in which a strong rubbing operation is performed to obtain a strong alignment regulating force, for example, IPS mode, STN mode, TN mode, OCB mode, ferroelectric type, antiferroelectric type, In the VA mode, in which rubbing may be performed to control how to fall, the effect of the present invention such that no rubbing scratches are generated or there is no alignment defect is remarkably recognized.
[0112]
Although the method for producing the alignment film of the present invention is not particularly limited, it can be specifically produced by the following procedure. The varnish of the present invention is applied to a glass substrate with a transparent electrode or a plastic substrate with a transparent electrode by a brush coating method, a dipping method, a spinner method, a spray method, a printing method, or the like. Next, the temperature of the substrate with electrodes is set to 50 to 150 ° C., preferably 80 to 120 ° C., and the solvent is evaporated. Then, in the glass substrate with a transparent electrode, the film is formed on the surface of the glass substrate by firing at a temperature of 150 to 400 ° C., preferably 180 to 280 ° C. In particular, when a plastic substrate is used, it is preferable to perform firing at a low temperature of about 120 to 160 ° C. in consideration of the heat resistance temperature of the substrate. Then, by rubbing the film surface in one direction with a cloth or the like, the alignment film of the present invention can be obtained.
[0113]
If the surface of the substrate is treated with a silane coupling agent before applying the varnish of the present invention to a glass substrate or a plastic substrate with a transparent electrode, the adhesion between the alignment film formed on the substrate surface and the substrate can be improved. Further improve.
[0114]
The liquid crystal composition used in the liquid crystal display device of the present invention is not particularly limited, and any liquid crystal composition may be used. When used in the production of a TN-type, STN-type, IPS-type, or OCB-type liquid crystal display element used together with the alignment film of the present invention, there is no particular limitation on the liquid crystal composition having a positive dielectric anisotropy used together. Various liquid crystal compositions can be used. For example, Japanese Patent No. 3086228, Japanese Patent No. 2635435, Japanese Patent Application Laid-Open No. 5-501735, Japanese Patent Application Laid-Open No. 8-157828, Japanese Patent Application Laid-Open No. 8-231960, JP-A-9-241644 (EP 885272A1), JP-A-9-302346 (EP 806466A1), JP-A-8-199168 (EP 722998A1), JP-A-9-235552, JP-A-9-255596, JP-A-9-241463 (EP 885271A1) and JP-A-10-204016 ( P 844229A1), Japanese Patent 10-204436, JP No. 10-231482, JP-2000-087040 Publication, liquid crystal compositions disclosed JP 2001-48822 publication, etc. are preferable.
[0115]
When the liquid crystal alignment film of the present invention is used for manufacturing a VA type liquid crystal display device, a liquid crystal composition having a negative dielectric anisotropy used together with the liquid crystal alignment film is disclosed in, for example, JP-A-57-114532. JP-A-2-4725, JP-A-4-224885, JP-A-8-40953, JP-A-8-104869, JP-A-10-101676, JP-A-10-168453, JP-A-10-168453 Japanese Patent Application Laid-Open Nos. Hei 10-236894, Hei 10-236990, Hei 10-236992, Hei 10-236993, Hei 10-236994, Hei 10-237000, Hei 10-237004 JP, JP-A-10-237024, JP-A-10-237035, JP-A-10-237075, JP-A-10-237015 Japanese Patent Application Laid-Open Nos. 0-237076, 10-237448 (EP 968261), 10-287874, 10-287875, 10-291945, 11-029581 and 11-029581. The liquid crystal compositions disclosed in Japanese Unexamined Patent Publication No. Hei 11-080049, JP-A-2000-256307, JP-A-2001-019965, JP-A-2001-072626, and JP-A-2001-192657 are preferable.
[0116]
【Example】
Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples. In the examples, all NMR was measured in deuterated chloroform. The molecular weight was measured using GPC, using polystyrene as a standard solution, and using DMF as an eluent.
[0117]
Evaluation method of liquid crystal display device
Hereinafter, the evaluation method of the liquid crystal display element used in the examples will be described. In addition, the measured values of various physical properties described in this example are values at 25 ° C.
[0118]
(1-1) Shaving by rubbing
Shaving of the alignment film after rubbing was visually observed.
○: No scraping
×: Shaved
(1-2) Display unevenness
When a voltage was applied to the liquid crystal cell and a display was performed, a portion having a display defect was visually observed.
○: No display failure
×: Display failure
[0119]
(2) Adhesion between liquid crystal alignment film and substrate
The adhesion of the liquid crystal alignment film to the substrate was determined in accordance with JIS K5400 8.5.2 according to the grid tape method, and 100 test pieces of 100 mm square were formed on the test piece, and a peeling test was performed using Cellotape (registered trademark). Then, the peeled state of the grid was observed and evaluated under the following conditions.
:: 100/100 without peeling
Δ: 50/100 to 90/100
×: 0/100 to 50/100
[0120]
(3) Surface hardness of liquid crystal alignment film
The surface hardness (indentation hardness) of the alignment film was measured using an ultra-fine indentation hardness tester (nano indentation tester) ENT1100a manufactured by Elionix Inc., with an indentation load of 10 mgf (split in 250 steps) and a test load holding time of 1 second. Was measured.
[0121]
(4) Pretilt angle
This was performed by the crystal rotation method. The measurement wavelength is 589 nm.
[0122]
(5) Voltage holding ratio
The test was performed according to the method described in "Mizushima et al., Proceedings of the 14th Liquid Crystal Symposium, p78". The voltage applied to the cell during the measurement was a gate width of 69 μs, a wave height of ± 4.5 V, and a frequency of 30 Hz or 0.3 Hz.
[0123]
As the alkenyl-substituted nadimide compound, three kinds of compounds having the following structural formula and sold by Maruzen Petrochemical Co., Ltd. were used.
BANI-H: a compound represented by the formula (2).
Embedded image
[0124]
BANI-M: a compound represented by the formula (3).
Embedded image
[0125]
BANI-X: a compound represented by the formula (4).
Embedded image
[0126]
Varnishes containing various polymers were prepared in order to specifically illustrate the embodiments of the present invention (Examples 1 to 9), and the varnish was blended with the alkenyl-substituted nadimide described above to prepare the liquid crystal aligning agent varnish of the present invention. Then, the performance was evaluated using the alignment film obtained therefrom (Examples 10 to 117). In addition, the varnishes to which no alkenyl-substituted nadimide was added were used as Comparative Examples 1 to 9 and were compared with the present invention.
[0127]
Example 1 (Preparation of liquid crystal aligning agent varnish A-1 (polyamic acid type))
3.0164 g (1.52 × 10 4) of 4,4′-diaminodiphenylmethane (hereinafter abbreviated as DDM) was placed in a 200 mL four-necked flask.-2mol), and 54.00 g of dehydrated N-methyl-2-pyrrolidone (hereinafter abbreviated as NMP), respectively, and stirred and dissolved under a dry nitrogen stream. While maintaining the temperature of the reaction system at 5 ° C., 2.9936 g (1.52 × 10 3) of cyclobutanetetracarboxylic dianhydride (hereinafter abbreviated as CBDA).-2mol), and reacted for 30 hours without temperature control. Finally, 40.00 g of butyl cellosolve (hereinafter abbreviated as BC) was added to each to synthesize a polyadic acid varnish having a polymer component concentration of 6% by weight. The synthesized varnish is referred to as a liquid crystal aligning agent varnish A1. In the examples of the present invention, the reaction was carried out while checking the viscosity during the reaction, and the viscosity of the liquid crystal aligning agent varnish after addition of butyl cellosolve was 55 to 65 mPa · s (using an E-type viscometer at a measurement temperature of 25 ° C. ), The reaction was terminated and stored at low temperature.
[0128]
Example 2 (Preparation of liquid crystal aligning agent varnish B-1 (polyamic acid type))
1.0657 g (5.02 × 10) of 4,4′-diaminodiphenylethane (hereinafter abbreviated as DDEt) as a diamine compound instead of DDM.-3mol) and 2.7351 g (5.02 × 10) of 1,1-bis (4-((aminophenyl) methyl) phenyl) -4-heptylcyclohexane (hereinafter abbreviated as APM7C6).-3mol), and 2.1900 g (1.00 × 10 4) of pyromellitic dianhydride (hereinafter abbreviated as PMDA) instead of CBDA as an acid dianhydride.-2mol), a liquid crystal aligning agent varnish B1 was synthesized in the same manner as in Example 1.
[0129]
Example 3 (Preparation of liquid crystal aligning agent varnish C-1 (polyamic acid type))
3.9891 g (9.22 ×) of 5-((4- (4- (4-pentylcyclohexyl) cyclohexyl) phenyl) methyl-1,3-diaminobenzene (hereinafter abbreviated as 5CHCHPhMDAB) as a diamine compound instead of DDM. 10-3mol), and 2.0109 g (9.22 × 10 2) of PMDA as an acid dianhydride instead of CBDA.-3mol) was added, and a liquid crystal aligning agent varnish C1 was synthesized in the same manner as in Example 1.
[0130]
Example 4 (Preparation of liquid crystal aligning agent varnish D-1 (polyamide type))
(Preparation of polyamide)
1.1692 g (5.51 × 10 5) of DDEt as a diamine compound was placed in a 500 mL three-necked flask.-3mol), and 3.0007 g (5.51 × 10 5) of APM7C6.-3), and 1.8300 g (1.10 × 10) of terephthalic acid (hereinafter abbreviated as TPA) as an acid compound.-2mol). In addition, 1 mL of pyridine and 2.803 g of lithium chloride (6.61 × 10 6-2mol), and dissolved in NMP (200 mL). To this solution was added 10.2448 g of triphenyl phosphite (3.31 × 10 3-2mol), and reacted at 100 ° C. for 4 hours in a nitrogen stream. After cooling, the reaction product was poured into methanol, and the polymer was reprecipitated and filtered to obtain a crude product. This crude product was washed by boiling twice with 500 mL of pure water and once with 500 mL of methanol for about 30 minutes each. After vacuum drying at 120 ° C. for 8 hours, 4.8 g (weight average molecular weight of 100,000) of polyamide was obtained.
[0131]
(Methylation of polyamide)
4.7 g of the above polyamide was placed in a three-necked flask and dissolved in 150 mL of NMP. 0.9469 g of sodium methoxide (1.75 × 10-2mol), and the mixture was further stirred at room temperature for 3 hours. 2.9856 g of methyl iodide (2.10 × 10-2mol), and reacted at room temperature for 2 hours. The reaction product was poured into 2.5 L of pure water, reprecipitated, filtered, washed twice with 1 L of pure water for 30 minutes each, and then once with 500 mL of a mixed solvent of pure water / IPA (weight ratio 1/1). Washed. Vacuum drying was performed at 120 ° C. for 9 hours to obtain 3.8 g of polymethylamide. The polymer was polyamide-1 (weight average molecular weight: 60,000), and the polyamide-1 was dissolved using NMP and BC in the same manner as in Example 1 to obtain a liquid crystal aligning agent varnish D-1. The substitution rate of amide hydrogen to methyl group was 100% as measured by NMR.
[0132]
Example 5 (Preparation of polyamideimide: E-1)
In a 50 ml three-necked flask, 1.1163 g (5.26 × 10-3mol), and 2.8650 g of APM7C6 (5.26 × 10-3mol) and dissolved in 20 g of NMP. 1.1470 g of PMDA (5.26 × 10-3mol), and the mixture was stirred for 1 hour in a nitrogen stream. Then, 1.0676 g (5.26 × 10 6 terephthalic acid dichloride (TPACl)) was added.-3mol). Thereafter, 1 ml of pyridine was added, and the mixture was further stirred for 2 hours. After the reaction was completed, 20 ml of acetic anhydride was added, and the mixture was reacted at 100 ° C. for 1 hour. After cooling, the reaction product was added to 300 ml of methanol to reprecipitate the polymer. The crude product was washed by boiling twice with 150 ml of pure water and once with 150 ml of methanol for about 30 minutes each. Vacuum drying was performed at 120 ° C. for 7 hours to obtain 4.8 g of each polyamideimide. The weight average molecular weight at this time was 110,000.
[0133]
1.0 g of the above polyamideimide was placed in a three-necked flask and dissolved in NMP (20 ml). 94 mg (2.3 mmol) of 60% sodium hydride was added thereto, and the mixture was stirred at room temperature for 3 hours. To this solution, 430 g (3.0 mmol) of methyl iodide was added, and the mixture was further reacted at room temperature for 2 hours. The reaction product was reprecipitated in 300 ml of pure water, filtered, washed by boiling twice in 150 ml of pure water for 30 minutes each, and then a mixed solvent of pure water / isopropyl alcohol (abbreviated as IPA) (weight ratio 1/1). Washed once with 50 ml. Vacuum drying was performed at 120 ° C. for 8 hours to obtain 960 mg of a target polyamideimide. This polymer is referred to as polyamideimide-1. At this time, the weight average molecular weight was 43,000, and the substitution rate of amide hydrogen for a methyl group was 97% as measured by NMR. A liquid crystal aligning agent varnish E-1 was obtained by dissolving with NMP and BC in the same manner as in Example 1.
[0134]
Example 6 (Preparation of mixed varnish-1)
The polymer component of the liquid crystal aligning agent varnish A-1 obtained according to Example 1 was 90% by weight, and the polymer component of the liquid crystal aligning agent varnish B-1 obtained according to Example 2 was 10% by weight. Was mixed with two kinds of varnishes to prepare a liquid crystal aligning agent varnish (B-1 / A-1: weight ratio 1/9).
[0135]
Examples 7 to 9 (Preparation of mixed varnish-2)
As for the liquid crystal aligning agent varnishes C-1, D-1, and E-1, the weight ratio of the polymer component in each liquid crystal aligning agent varnish to the polymer component of the liquid crystal aligning agent varnish A-1 was the same as in Example 6. Liquid crystal aligning agent varnish C-1 / A-1 (weight ratio 1/9) (Example 7), liquid crystal aligning agent varnish D was mixed with liquid crystal aligning agent varnish A-1 so as to be 1/9. -1 / A-1 (weight ratio 1/9) (Example 8) and liquid crystal aligning agent varnish E-1 / A-1 (weight ratio 1/9) (Example 9) were prepared.
[0136]
Examples 10 to 11
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish A-1>
Take 10.0 g of the liquid crystal aligning agent varnish A-1 obtained by the method of Example 1, 0.0060 g of BANI-H as an alkenyl-substituted nadimide compound in Example 10, 0.0600 g of Example 11 to 10 g of NMP. After dissolution, the mixture was added, and the mixture was stirred and mixed at room temperature for 1 hour. These liquid crystal aligning agent varnishes are A-2 in Example 10 and A-3 in Example 11.
[0137]
Examples 12 to 13
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish A-1>
The alkenyl-substituted nadimide compound was changed to BANI-M, and was added in the same manner as in Examples 10 to 11 except that 0.0060 g in Example 12 and 0.0600 g in Example 13 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are A-4 in Example 12 and A-5 in Example 13.
[0138]
Examples 14 to 15
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish A-1>
The alkenyl-substituted nadimide compound was changed to BANI-X, and in the same manner as in Examples 10 to 11, except that 0.0060 g in Example 14 and 0.0600 g in Example 15 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are A-6 in Example 14 and A-7 in Example 15.
[0139]
Examples 16 to 17
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish B-1>
10.0 g of the liquid crystal aligning agent varnish B-1 obtained by the method of Example 2 was used, and BANI-H was used as an alkenyl-substituted nadimide compound in an amount of 0.0060 g in Example 16 and 0.0600 g in Example 17 to 10 g of NMP. After dissolution, the mixture was added, and the mixture was stirred and mixed at room temperature for 1 hour. These liquid crystal aligning agent varnishes are B-2 in Example 16 and B-3 in Example 17.
[0140]
Examples 18 to 19
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish B-1>
The alkenyl-substituted nadimide compound was changed to BANI-M, and was added in the same manner as in Examples 16 to 17 except that 0.0060 g in Example 18 and 0.0600 g in Example 19 were added by dissolving in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are B-4 in Example 18 and B-5 in Example 19.
[0141]
Examples 20 to 21
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish B-1>
The alkenyl-substituted nadimide compound was changed to BANI-X, and in the same manner as in Examples 16 to 17, except that 0.0060 g in Example 20 and 0.0600 g in Example 21 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are B-6 in Example 2 and B-7 in Example 21.
[0142]
Examples 22 to 23
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish C-1>
10.0 g of the liquid crystal aligning agent varnish C-1 obtained by the method of Example 3 was used, and BANI-H was used as an alkenyl-substituted nadimide compound in 0.0022 g in Example 22 and 0.0600 g in Example 23 to 10 g of NMP. After dissolution, the mixture was added, and the mixture was stirred and mixed at room temperature for 1 hour. These liquid crystal aligning agent varnishes are C-2 in Example 22 and C-3 in Example 23.
[0143]
Examples 24 to 25
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish C-1>
The alkenyl-substituted nadimide compound was changed to BANI-M, and was added in the same manner as in Examples 22 to 23 except that 0.0060 g in Example 24 and 0.0600 g in Example 25 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are C-4 in Example 24 and C-5 in Example 19.
[0144]
Examples 26 to 27
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish C-1>
The alkenyl-substituted nadimide compound was changed to BANI-X, and in the same manner as in Examples 22 to 23, except that 0.0060 g in Example 20 and 0.0600 g in Example 21 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are C-6 in Example 26 and C-7 in Example 27.
[0145]
Examples 28 to 29
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish D-1>
10.0 g of the liquid crystal aligning agent varnish D-1 obtained by the method of Example 4 was used, and BANI-H was used as an alkenyl-substituted nadimide compound in an amount of 0.0060 g in Example 28 and 0.0600 g in Example 29 to 10 g of NMP. After dissolution, the mixture was added, and the mixture was stirred and mixed at room temperature for 1 hour. These liquid crystal aligning agent varnishes are D-2 in Example 22 and D-3 in Example 23.
[0146]
Examples 30 to 31
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish D-1>
The alkenyl-substituted nadimide compound was changed to BANI-M, and was added in the same manner as in Examples 28 to 29 except that 0.0060 g in Example 30 and 0.0600 g in Example 31 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are D-4 in Example 30 and D-5 in Example 31.
[0147]
Examples 32 to 33
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish D-1>
The alkenyl-substituted nadimide compound was changed to BANI-X, and in the same manner as in Examples 28 to 29 except that 0.0060 g in Example 32 and 0.0600 g in Example 33 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are D-6 in Example 32 and D-7 in Example 33.
[0148]
Examples 34-35
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish E-1>
10.0 g of the liquid crystal aligning agent varnish E-1 obtained according to the method of Example 5 was used, and 0.0060 g of BANI-H was used as the alkenyl-substituted nadiimide compound in Example 34, and 0.0600 g was used in Example 35. Each was dissolved in 10 g of NMP and then added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are E-2 in Example 34 and E-3 in Example 35.
[0149]
Examples 36 to 37
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish E-1>
The alkenyl-substituted nadimide compound was changed to BANI-M, and was added in the same manner as in Examples 34 to 35 except that 0.0060 g in Example 36 and 0.0600 g in Example 37 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are E-4 in Example 36 and E-5 in Example 37.
[0150]
Examples 38-39
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish E-1>
The alkenyl-substituted nadimide compound was changed to BANI-X, and in the same manner as in Examples 34 to 35, except that 0.0060 g in Example 38 and 0.0600 g in Example 39 were dissolved and added in 10 g of NMP. Was. These liquid crystal aligning agent varnishes are E-6 in Example 2 and E-7 in Example 21.
[0151]
Examples 40 to 41
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish B-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish B-1 / A-1 obtained by the method of Example 6 was used, and BANI-H was 0.0060 g in Example 40 and 0.0600 g in Example 41 as alkenyl-substituted nadimide compound. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are B-2 / A-2 in Example 40 and B-3 / A-3 in Example 41.
[0152]
Examples 42 to 43
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish B-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish B-1 / A-1 obtained by the method of Example 6 was used, and BANI-M was 0.0060 g in Example 42 and 0.0600 g in Example 43 as alkenyl-substituted nadimide compound. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are B-4 / A-4 in Example 42 and B-5 / A-5 in Example 43.
[0153]
Examples 44 to 45
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish B-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish B-1 / A-1 obtained by the method of Example 6 was used, and BANI-X was used as the alkenyl-substituted nadiimide compound in the amount of 0.0060 g in Example 44 and 0.0600 g in Example 45. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are B-6 / A-6 in Example 44, and B-7 / A-7 in Example 45.
[0154]
Examples 46 to 47
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish C-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish C-1 / A-1 obtained by the method of Example 7 was used, and 0.0060 g of BANI-H was used as the alkenyl-substituted nadimide compound in Example 46, and 0.0600 g in Example 47. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are C-2 / A-2 in Example 46 and C-3 / A-3 in Example 47.
[0155]
Examples 48 to 49
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish C-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish C-1 / A-1 obtained by the method of Example 7 was used, and 0.0060 g of BANI-M was used as the alkenyl-substituted nadiimide compound in Example 48, and 0.0600 g in Example 49. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are C-4 / A-4 in Example 48 and C-5 / A-5 in Example 49.
[0156]
Examples 50 to 51
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish C-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish C-1 / A-1 obtained by the method of Example 7 was used, and 0.0060 g of BANI-X was used as the alkenyl-substituted nadimide compound in Example 50, and 0.0600 g in Example 51. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are C-6 / A-6 in Example 50 and C-7 / A-7 in Example 51.
[0157]
Examples 52 to 53
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish D-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish D-1 / A-1 obtained by the method of Example 8 was used, and 0.0060 g of BANI-H was used as the alkenyl-substituted nadimide compound in Example 52, and 0.0600 g in Example 53. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are D-2 / A-2 in Example 52 and D-3 / A-3 in Example 53.
[0158]
Examples 54 to 55
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish D-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish D-1 / A-1 obtained by the method of Example 8 was used, and BANI-M was 0.0060 g in Example 54 and 0.0600 g in Example 55 as an alkenyl-substituted nadimide compound. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are D-4 / A-4 in Example 54 and D-5 / A-5 in Example 55.
[0159]
Examples 56 to 57
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish D-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish D-1 / A-1 obtained by the method of Example 8 was used, and BANI-X was used as the alkenyl-substituted nadiimide compound in the amount of 0.0060 g in Example 56 and 0.0600 g in Example 57. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are D-6 / A-6 in Example 56, and D-7 / A-7 in Example 57.
[0160]
Examples 58 to 59
<Addition of alkenyl-substituted nadimide compound: BANI-H to liquid crystal aligning agent varnish E-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish E-1 / A-1 obtained by the method of Example 9 was used, and BANI-H was used as an alkenyl-substituted nadiimide compound in the amount of 0.0060 g in Example 58 and 0.0600 g in Example 59. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are E-2 / A-2 in Example 58, and E-3 / A-3 in Example 59.
[0161]
Examples 60 to 61
<Addition of alkenyl-substituted nadimide compound: BANI-M to liquid crystal aligning agent varnish E-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish E-1 / A-1 obtained by the method of Example 9 was used, and BANI-M was 0.0060 g in Example 60 and 0.0600 g in Example 61 as an alkenyl-substituted nadimide compound. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are E-4 / A-4 in Example 60 and E-5 / A-5 in Example 61.
[0162]
Examples 62 to 63
<Addition of alkenyl-substituted nadimide compound: BANI-X to liquid crystal aligning agent varnish E-1 / A-1>
10.0 g of the liquid crystal aligning agent varnish E-1 / A-1 obtained by the method of Example 9 was used, and BANI-X was 0.0060 g in Example 62 and 0.0600 g in Example 63 as alkenyl-substituted nadimide compound. Was dissolved in 10 g of NMP, and added, followed by stirring and mixing at room temperature for 1 hour. These liquid crystal aligning agent varnishes are E-6 / A-6 in Example 62, and E-7 / A-7 in Example 63.
[0163]
Table 1 summarizes the adjustment examples of the liquid crystal aligning agent varnishes of Examples 1 to 63.
[0164]
[Table 1]
[0165]
Example 64
Evaluation of lines and scratches by rubbing and evaluation of liquid crystal alignment (creation of liquid crystal alignment, pretilt angle measurement cell)
The liquid crystal aligning agent varnish A-2 obtained in Example 10 was diluted with an NMP-BC mixed solvent (weight ratio 1/1), and adjusted such that the polymer component concentration in the liquid crystal aligning agent varnish became 3% by weight. Then, a liquid crystal aligning agent varnish for coating was obtained. This diluted varnish was applied on a substrate with a transparent electrode by a spinner and preliminarily baked at 80 ° C. for about 5 minutes. Next, the film was baked at 210 ° C. for 30 minutes to form an alignment film having a thickness of 60 nm, and the entire surface was rubbed to perform an alignment treatment. Prepare another one of the same substrates, sprinkle a 20 μm gap material on the alignment film surface of one substrate, overlay the other substrate so that the alignment film surfaces face each other, and seal with an epoxy curing agent. Thus, an anti-parallel cell having a gap of 20 μm was prepared.
Liquid crystal composition-1 having the following positive dielectric anisotropy was injected into this cell, and the injection port was sealed with a photocuring agent. Next, a heat treatment was performed at 110 ° C. for 30 minutes to produce a cell with homogeneous alignment. This cell was sandwiched between two polarizing plates arranged in a crossed Nicols state, and when rotated in the same, uniform and clear alignment defects (hereinafter referred to as streaks and scratches) due to scratches generated in the alignment film by rubbing were observed. Light and dark were observed, and it was confirmed that the liquid crystal molecules were favorably aligned by rubbing. The pretilt angle of the cell measured by a crystal rotation method was 1.0 °.
[0166]
Liquid crystal composition-1
Embedded image
[0167]
Preparation and measurement of cell for voltage holding ratio evaluation
An anti-parallel cell was prepared in the same manner as the pretilt angle measurement cell except that the gap cell was changed to 7 μm in the evaluation cell in Example 10, and used as a cell for voltage holding ratio evaluation. The voltage holding ratio was 98.5% at 30 Hz, and 93.3% at 0.3 Hz. No Vth unevenness was observed at all.
[0168]
Evaluation of adhesion
The sintering was performed under the same conditions as in the sintering of the liquid crystal cell except that the liquid crystal aligning agent varnish A-1 used in Example 10 was applied to the substrate with a spinner. When the adhesion was evaluated in accordance with the grid tape method of JIS K5400 8.5.2. No peeling of the liquid crystal alignment film from the substrate was confirmed (確認: 100/100).
[0169]
Evaluation of surface hardness
The liquid crystal alignment agent varnish A-1 used in Example 10 was baked under the same conditions as in the preparation of the liquid crystal cell, except that the liquid crystal aligning agent varnish A-1 was applied on a substrate with a transparent electrode by a spinner so as to have a film thickness of 1 μm. . When the surface hardness of the liquid crystal alignment film formed on the substrate with the transparent electrode was measured, it was 63.5 (mgf / μm2)Met.
[0170]
Examples 65 to 117
Regarding other liquid crystal aligning agent varnishes, a pretilt angle measurement cell and a cell for voltage holding ratio evaluation were prepared in the same manner as in Example 64, and the pretilt angle, liquid crystal orientation, display failure, voltage holding ratio, and display unevenness were measured. Was evaluated. In Examples 76 to 81 and Examples 100 to 105, the pretilt angle and the alignment of the liquid crystal were the same as in Example 64 except that a liquid crystal composition having the following negative dielectric anisotropy was injected into the liquid crystal cell. The properties, display defects, voltage holding ratio and display unevenness were evaluated. The adhesion and the surface hardness were also evaluated in the same manner as in Example 64. The results are summarized in Tables 2 and 3.
[0171]
Liquid crystal composition-2
Embedded image
[0172]
Comparative Examples 1 to 9
Liquid crystal aligning agent varnishes prepared in Examples 1 to 9 to which no alkenyl-substituted nadimide compound is added, A-1, B-1, C-1, D-1, E-1, B-1 / A-1, C- A cell for pretilt angle measurement and a cell for voltage holding ratio evaluation were prepared in the same manner as in Example 64 except that 1 / A-1, D-1 / A-1 and E-1 / A-1 were used. , Pretilt angle, liquid crystal orientation, display failure, voltage holding ratio, and display unevenness were evaluated. In Comparative Examples 3 and 7, except that the same liquid crystal composition having the same negative dielectric anisotropy as in Examples 76 and 100 was injected into the liquid crystal cell, the pretilt angle, the orientation of the liquid crystal, the display failure, The voltage holding ratio and display unevenness were similarly evaluated. The adhesion and the surface hardness were also evaluated in the same manner as in Example 64. The results are summarized in Tables 2 and 3.
[0173]
[Table 2]
[0174]
[Table 3]
[0175]
In Tables 2 and 3, the evaluation of rubbing for streaks and scratches, and the mark ○ for display unevenness indicates that streaks, scratches and display unevenness were hardly observed, and the mark x indicates streaks, scratches and display unevenness recognized for practical use. This is a problem. Similarly, in the evaluation of the adhesion, the mark “○” is useful in practical use, and the mark “X” indicates a problem.
[0176]
From the results shown in Tables 2 and 3, the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide compound was added exhibited good liquid crystal alignment properties with uniform and clear brightness without rubbing or scratches. You can see that. On the other hand, in the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which no alkenyl-substituted nadiimide compound was added, remarkable streaks and scratches were observed in the rubbing direction. Further, it can be seen that the orientation of the liquid crystal is also disturbed.
[0177]
From these results, the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide compound was added was compared with the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide compound was not added, and the abrasion due to rubbing was reduced. It can be seen that the voltage holding ratio has been improved by the reduction of the above.
[0178]
Evaluation of adhesion to substrate
From the results in Tables 2 and 3, the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide compound was added was smaller than the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide compound was not added. It can be seen that good adhesion is exhibited.
[0179]
Evaluation of indentation hardness of alignment film
From the results of Tables 2 and 3, the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide compound was added was compared with the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadimide compound was not added. It turns out that it has high surface hardness.
[0180]
According to the results of Tables 2 and 3, in the liquid crystal alignment film exhibiting a pretilt angle of 1.0 to 89.5 °, the effect of adding the alkenyl-substituted nadiimide compound on rubbing scratches and scraping was confirmed. Therefore, TN liquid crystal display element, STN liquid crystal display element, TN-TFT liquid crystal display element, IPS liquid crystal display element, VA liquid crystal display element, OCB liquid crystal display element, ferroelectric liquid crystal display element, anti-ferroelectric It has been found that the effects of the present invention can be recognized in various types of liquid crystal display devices such as a liquid crystal display device.
[0181]
【The invention's effect】
The mechanical strength of the liquid crystal alignment film is improved by using the liquid crystal alignment film formed from the liquid crystal alignment agent varnish to which the alkenyl-substituted nadiimide compound of the present invention is added, and as a result, streaks and scratches on the alignment film due to the rubbing operation are reduced. The effect of prevention is obtained. That is, according to the present invention, a higher-performance TN liquid crystal display element, STN liquid crystal display element, TN-TFT liquid crystal display element, IPS liquid crystal display element, VA liquid crystal display element, OCB liquid crystal display element, A dielectric liquid crystal display element and an antiferroelectric liquid crystal display element can be realized.
Claims (9)
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JP2003134412A JP4192670B2 (en) | 2003-05-13 | 2003-05-13 | Liquid crystal aligning agent varnish, alignment film using the varnish, and liquid crystal display element having the alignment film |
KR1020040032945A KR100676784B1 (en) | 2003-05-13 | 2004-05-11 | Liquid crystal aligning film and liquid crystal display element using said liquid crystal aligning film |
KR1020060092795A KR20060115682A (en) | 2003-05-13 | 2006-09-25 | Liquid crystal aligning film and liquid crystal display element using said liquid crystal aligning film |
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JP4192670B2 (en) | 2008-12-10 |
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KR100676784B1 (en) | 2007-01-31 |
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