JP5713009B2 - 液晶配向処理剤、液晶配向膜及び液晶表示素子 - Google Patents
液晶配向処理剤、液晶配向膜及び液晶表示素子 Download PDFInfo
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- JP5713009B2 JP5713009B2 JP2012511706A JP2012511706A JP5713009B2 JP 5713009 B2 JP5713009 B2 JP 5713009B2 JP 2012511706 A JP2012511706 A JP 2012511706A JP 2012511706 A JP2012511706 A JP 2012511706A JP 5713009 B2 JP5713009 B2 JP 5713009B2
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- CFTXGNJIXHFHTH-UHFFFAOYSA-N bis(4-aminophenyl) benzene-1,4-dicarboxylate Chemical compound C1=CC(N)=CC=C1OC(=O)C1=CC=C(C(=O)OC=2C=CC(N)=CC=2)C=C1 CFTXGNJIXHFHTH-UHFFFAOYSA-N 0.000 description 1
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- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
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- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
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- 239000003480 eluent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
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- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
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- URMCFMOUMIWRAH-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine;n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN.CO[Si](OC)(OC)CCCNCCN URMCFMOUMIWRAH-UHFFFAOYSA-N 0.000 description 1
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- 238000007645 offset printing Methods 0.000 description 1
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- OURNLUUIQWKTRH-UHFFFAOYSA-N oxirane;phenol Chemical compound C1CO1.OC1=CC=CC=C1.OC1=CC=CC=C1 OURNLUUIQWKTRH-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- 229920000515 polycarbonate Polymers 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
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- 238000007639 printing Methods 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- JREWFSHZWRKNBM-UHFFFAOYSA-N pyridine-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1=CN=C(C(O)=O)C(C(O)=O)=C1C(O)=O JREWFSHZWRKNBM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
-
- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
-
- 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
- C08G73/1075—Partially aromatic polyimides
-
- 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
- C08G73/1075—Partially aromatic polyimides
- C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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Description
(1)
下記の式[1]で示されるジアミン化合物、及び下記の式[2]で示されるジアミン化合物を含むジアミン成分とテトラカルボン酸二無水物とを反応させて得られる重合体を含有する液晶配向処理剤。
式[1]中、X1が−NHCO−である(1)記載の液晶配向処理剤。
前記テトラカルボン酸二無水物が、下記の式[3]で示されるテトラカルボン酸二無水物である(1)又は(2)記載の液晶配向処理剤。
Z1が、下記の式[3a]〜式[3j]で示される構造である(3)に記載の液晶配向処理剤。
液晶配向処理剤中に、エポキシ基、オキセタン基、イソシアネート基及びシクロカーボネート基からなる群より選ばれる少なくとも1種の置換基を有する架橋性化合物、ヒドロキシル基、ヒドロキシアルキル基、アルコキシル基及び低級アルコキシアルキル基からなる群より選ばれる少なくとも1種の置換基を有する架橋性化合物、又は重合性不飽和結合を有する架橋性化合物を有する(1)〜(4)のいずれか一項に記載の液晶配向処理剤。
液晶配向処理剤中の重合体がポリアミド酸を脱水閉環させて得られるポリイミドである(1)〜(5)のいずれか一項に記載の液晶配向処理剤。
液晶配向処理剤中に5〜60質量%の貧溶媒を含有する(1)〜(6)のいずれか一項に記載の液晶配向処理剤。
(1)〜(7)のいずれか一項に記載の液晶配向処理剤を用いて得られる液晶配向膜。
(8)に記載の液晶配向膜を有する液晶表示素子。
(1)〜(7)のいずれか一項に記載の液晶配向処理剤を用いて得られる液晶配向膜であって、液晶に熱や紫外線照射により重合する重合性化合物を混合した液晶材料を用いて、液晶層に電圧を印加しながら前記重合性化合物を重合させて得られるポリマーで、駆動時の液晶の配向方向を制御する方法により得られる液晶表示素子に用いられる液晶配向膜。
(10)に記載の液晶配向膜を具備する液晶表示素子であって、液晶に熱や紫外線照射により重合する重合性化合物を混合した液晶材料を用いて、液晶層に電圧を印加しながら前記重合性化合物を重合させて得られるポリマーで、駆動時の液晶の配向方向を制御する方法により得られる液晶表示素子。
本発明の特定ジアミン化合物は、下記の式[1]で示されるジアミン化合物である。
本発明の特定側鎖型ジアミン化合物は、下記の式[2]で示されるジアミン化合物である。
本発明においては、本発明の効果を損なわない限りにおいて、特定ジアミン化合物及び特定側鎖型ジアミン化合物以外のその他のジアミン化合物を、ジアミン成分として併用することができる。その具体例を以下に挙げる。
本発明の重合体を得るためには、下記の式[3]で示されるテトラカルボン酸二無水物(特定テトラカルボン酸二無水物ともいわれる)を原料の一部に用いることが好ましい。
本発明においては、本発明の効果を損なわない限りにおいて、特定テトラカルボン酸二無水物以外のその他のテトラカルボン酸二無水物を併用することができる。その具体例は以下の化合物の二無水物である。
本発明で用いる重合体は、上述したように、上記式[1]で示される特定ジアミン化合物、及び上記式[2]で示される特定側鎖型ジアミン化合物を含有するジアミン成分とテトラカルボン酸二無水物との反応によって得られるポリアミド酸や、このポリアミド酸を脱水閉環させて得られるポリイミドである。かかるポリアミド酸及びポリイミドのいずれも液晶配向膜を得るための重合体として有用である。
本発明の液晶配向処理剤は、液晶配向膜を形成するための塗布液であり、樹脂被膜を形成するための樹脂成分が有機溶媒に溶解した溶液である。ここで、前記の樹脂成分は、上記した本発明の重合体、すなわち、上記式[1]で示される特定ジアミン化合物、及び上記式[2]で示される特定側鎖型ジアミン化合物を含むジアミン成分とテトラカルボン酸二無水物とを反応させて得られる重合体から選ばれる少なくとも一種の重合体を含む樹脂成分である。その際、樹脂成分の含有量は1質量%〜20質量%が好ましく、より好ましくは3質量%〜15質量%、特に好ましくは3〜10質量%である。
本発明の液晶配向処理剤は、基板上に塗布、焼成した後、ラビング処理や光照射などで配向処理をして、又は垂直配向用途などでは配向処理無しで液晶配向膜として用いることができる。この際、用いる基板としては透明性の高い基板であれば特に限定されず、ガラス基板、アクリル基板やポリカーボネート基板などのプラスチック基板などを用いることができる。また、液晶駆動のためのITO電極などが形成された基板を用いることがプロセスの簡素化の観点から好ましい。また、反射型の液晶表示素子では片側の基板のみにならばシリコンウエハー等の不透明な物でも使用でき、この場合の電極はアルミ等の光を反射する材料も使用できる。
(テトラカルボン酸二無水物)
CBDA:1,2,3,4−シクロブタンテトラカルボン酸二無水物
BODA:ビシクロ[3,3,0]オクタン−2,4,6,8−テトラカルボン酸二無水物
TCA:2,3,5−トリカルボキシシクロペンチル酢酸―1,4:2,3−二無水物
TDA:3,4−ジカルボキシ−1,2,3,4−テトラヒドロ−1−ナフタレンコハク酸二無水物
DA−1:4−(トランスー4−ヘプチルシクロヘキシル)ベンズアミド−2‘,4’−フェニレンジアミン
PCH7DAB:1,3−ジアミノ−4−〔4−(トランス−4−n−ヘプチルシクロへキシル)フェノキシ〕ベンゼン
PBCH5DAB:1,3−ジアミノ−4−{4−〔トランス−4−(トランス−4−n−ペンチルシクロへキシル)シクロへキシル〕フェノキシ}ベンゼン
m−PBCH5DABz:1,3−ジアミノ−5−{4−〔4−(トランス−4−n−ペンチルシクロヘキシル)シクロヘキシル〕フェノキシメチル}ベンゼン
ColDAB−1:下記の式で示される特定側鎖型ジアミン化合物
p−PDA:p−フェニレンジアミン
m−PDA:m−フェニレンジアミン
DBA:3,5−ジアミノ安息香酸
AP18:1,3−ジアミノ−4−オクタデシルオキシベンゼン
架橋性化合物(1):YH−434L(東都化成製)(エポキシ系架橋性化合物)
架橋性化合物(2):OXT−221(東亜合成製)(オキセタン系架橋性化合物)
架橋性化合物(3):下記の式で示される架橋性化合物(ヒドロキシル化フェノール系架橋性化合物)
NMP:N−メチル−2−ピロリドン
BCS:ブチルセロソルブ
合成例におけるポリイミドの分子量は、常温ゲル浸透クロマトグラフィー(GPC)装置(GPC−101)(昭和電工製)、カラム(KD−803、KD−805)(Shodex製)を用いて、以下のようにして測定した。
カラム温度:50℃
溶離液:N,N’−ジメチルホルムアミド(添加剤として、臭化リチウム−水和物(LiBr・H2O)が30mmol/L、リン酸・無水結晶(o−リン酸)が30mmol/L、テトラヒドロフラン(THF)が10ml/L)
流速:1.0ml/分
検量線作成用標準サンプル:TSK 標準ポリエチレンオキサイド(分子量 約900,000、150,000、100,000、30,000)(東ソー製)、及びポリエチレングリコール(分子量 約12,000、4,000、1,000)(ポリマーラボラトリー製)。
合成例におけるポリイミドのイミド化率は次のようにして測定した。ポリイミド粉末20mgをNMRサンプル管(NMRサンプリングチューブスタンダード φ5(草野科学製))に入れ、重水素化ジメチルスルホキシド(DMSO−d6、0.05%TMS(テトラメチルシラン)混合品)0.53mlを添加し、超音波をかけて完全に溶解させた。この溶液をNMR測定機(JNW−ECA500)(日本電子データム製)にて500MHzのプロトンNMRを測定した。イミド化率は、イミド化前後で変化しない構造に由来するプロトンを基準プロトンとして決め、このプロトンのピーク積算値と、9.5から10.0ppm付近に現れるアミド酸のNH基に由来するプロトンピーク積算値とを用い以下の式によって求めた。
イミド化率(%)=(1−α・x/y)×100
上記式において、xはアミド酸のNH基由来のプロトンピーク積算値、yは基準プロトンのピーク積算値、αはポリアミド酸(イミド化率が0%)の場合におけるアミド酸のNH基プロトン1個に対する基準プロトンの個数割合である。
BODA(7.50g,30.0mmol)、DA−1(1.53g,3.75mmol)、PCH7DAB(5.71g,15.0mmol)、p−PDA(2.03g,18.8mmol)をNMP(30.1g)中で混合し、80℃で5時間反応させた後、CBDA(1.47g,7.50mmol)とNMP(24.8g)を加え、40℃で6時間反応させ、樹脂固形分濃度が、24.9質量%のポリアミド酸溶液(1)を得た。このポリアミド酸の数平均分子量は25,400、重量平均分子量は73,300であった。
合成例1で得られた樹脂固形分濃度が24.9質量%のポリアミド酸溶液(1)(20.2g)に、NMPを加えて6質量%に希釈した後、イミド化触媒として無水酢酸(2.47g)、ピリジン(1.88g)を加え、80℃で4時間反応させた。この反応溶液をメタノール(320ml)中に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(2)を得た。このポリイミドのイミド化率は55%であり、数平均分子量は21,200、重量平均分子量は54,400であった。
BODA(6.89g,27.5mmol)、DA−1(1.40g,3.43mmol)、PBCH5DAB(4.47g,10.3mmol)、DBA(3.14g,20.6mmol)をNMP(28.6g)中で混合し、80℃で4.5時間反応させた後、CBDA(1.35g,6.88mmol)とNMP(23.4g)を加え、40℃で6時間反応させ、樹脂固形分濃度が、24.9質量%のポリアミド酸溶液を得た。
BODA(3.99g,15.9mmol)、DA−1(1.86g,4.56mmol)、m−PBCH5DABz(2.54g,5.69mmol)、DBA(1.91g,12.6mmol)をNMP(19.3g)中で混合し、80℃で4時間反応させた後、CBDA(1.34g,6.83mmol)とNMP(15.7g)を加え、40℃で6時間反応させ、樹脂固形分濃度が25.0質量%のポリアミド酸溶液を得た。
BODA(7.09g,28.3mmol)、DA−1(2.89g,7.09mmol)、ColDAB−1(2.62g,5.32mmol)、m−PDA(2.49g,23.0mmol)をNMP(27.9g)中で混合し、80℃で4時間反応させた後、CBDA(1.39g,7.09mmol)とNMP(22.5g)を加え、40℃で5時間反応させ、樹脂固形分濃度が24.6質量%のポリアミド酸溶液を得た。
TCA(3.43g,15.3mmol)、DA−1(0.62g,1.52mmol)、PCH7DAB(2.33g,6.12mmol)、p−PDA(0.83g,7.68mmol)をNMP(21.6g)中で混合し、40℃で7時間反応させ、樹脂固形分濃度が25.0質量%のポリアミド酸溶液(6)を得た。このアミド酸の数平均分子量は25,900、重量平均分子量は69,900であった。
TCA(3.11g,13.9mmol)、DA−1(0.57g,1.40mmol)、PBCH5DAB(1.80g,4.16mmol)、m−PDA(0.90g,8.32mmol)をNMP(19.2g)中で混合し、40℃で7時間反応させ、樹脂固形分濃度が24.9質量%のポリアミド酸溶液を得た。
BODA(1.21g,4.84mmol)、DA−1(1.31g,3.21mmol)、PBCH5DAB(2.09g,4.83mmol)、DBA(1.23g,8.08mmol)をNMP(13.8g)中で混合し、80℃で1.5時間反応させた後、TCA(2.53g,11.3mmol)とNMP(11.3g)を加え、40℃で8時間反応させ、樹脂固形分濃度が25.0質量%のポリアミド酸溶液を得た。
BODA(1.22g,4.88mmol)、DA−1(0.66g,1.62mmol)、ColDAB−1(1.60g,3.25mmol)、m−PDA(1.23g,11.4mmol)をNMP(12.5g)中で混合し、80℃で1.5時間反応させた後、TCA(2.55g,11.4mmol)とNMP(10.0g)を加え、40℃で7時間反応させ、樹脂固形分濃度が24.4質量%のポリアミド酸溶液を得た。
TDA(1.49g,4.96mmol)、DA−1(1.35g,3.31mmol)、PCH7DAB(2.52g,6.62mmol)、DBA(1.01g,6.64mmol)をNMP(14.2g)中で混合し、80℃で2時間反応させた後、CBDA(2.27g,11.6mmol)とNMP(11.7g)を加え、40℃で6時間反応させ、樹脂固形分濃度が25.0質量%のポリアミド酸溶液を得た。
BODA(6.79g,27.1mmol)、PCH7DAB(5.16g,13.6mmol)、p−PDA(2.20g,20.3mmol)をNMP(25.0g)中で混合し、80℃で4時間反応させた後、CBDA(1.33g,6.78mmol)とNMP(20.5g)を加え、40℃で6時間反応させ、樹脂固形分濃度が、25.4質量%のポリアミド酸溶液(11)を得た。このポリアミド酸の数平均分子量は24,400、重量平均分子量は69,400であった。
合成例11で得られた樹脂固形分濃度が25.4質量%のポリアミド酸溶液(11)(20.0g)に、NMPを加えて6質量%に希釈した後、イミド化触媒として無水酢酸(2.45g)、ピリジン(1.86g)を加え、80℃で4時間反応させた。この反応溶液をメタノール(300ml)中に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(12)を得た。このポリイミドのイミド化率は56%であり、数平均分子量は19,800、重量平均分子量は51,900であった。
BODA(6.74g,26.9mmol)、DA−1(1.37g,3.36mmol)、AP18(5.07g,13.5mmol)、p−PDA(1.82g,16.8mmol)をNMP(26.3g)中で混合し、80℃で4時間反応させた後、CBDA(1.32g,6.73mmol)とNMP(22.8g)を加え、40℃で6時間反応させ、樹脂固形分濃度が、24.7質量%のポリアミド酸溶液を得た。
BODA(6.23g,24.9mmol)、DA−1(5.07g,12.4mmol)、p−PDA(2.02g,18.7mmol)をNMP(24.0g)中で混合し、80℃で4時間反応させた後、CBDA(1.22g,6.22mmol)とNMP(19.6g)を加え、40℃で6時間反応させ、樹脂固形分濃度が、25.0質量%のポリアミド酸溶液を得た。
BODA(1.12g,4.48mmol)、ColDAB−1(1.47g,2.98mmol)、m−PDA(1.29g,11.9mmol)をNMP(10.8g)中で混合し、80℃で2時間反応させた後、TCA(2.34g,10.4mmol)とNMP(8.42g)を加え、40℃で8時間反応させ、樹脂固形分濃度が、24.4質量%のポリアミド酸溶液を得た。
下記する実施例1〜実施例13、及び比較例1〜比較例5では、液晶配向処理剤の製造例を記載するが、各液晶配向処理剤の評価のために使用される本発明の液晶配向処理剤を表49、及び表50に示す。
液晶配向処理剤を、3×4cmITO電極付き基板のITO面にスピンコートし、ホットプレート上にて80℃で5分間、熱循環型クリーンオーブン中にて220℃で30分間加熱処理をして膜厚100nmのポリイミド液晶配向膜付きの基板を得た。
上記の「液晶配向膜の作製」で得られた液晶配向膜付きの基板、液晶にMLC−6608(メルク・ジャパン製)、及び全自動接触角計CA−W(協和界面科学製)を用い、液晶の濡れ拡がり性の評価を行った。評価は、液晶が液晶配向膜に着液して10秒後の液晶の接触角を測定し、その液晶の接触角が低いほど、液晶配向膜上における液晶の濡れ拡がり性が高いとした。
上記の「液晶配向膜の作製」で得られた液晶配向膜付きの基板の塗膜面をロール径120mm、レーヨン布のラビング装置にて、回転数300rpm、移動速度20mm/sec、押し込み量0.2mmの条件にてラビング処理をした。この液晶配向膜付き基板を2枚用意し、液晶配向膜面を内側にして6μmのスペーサーを挟み、ラビング方向が逆向きになるようにして組み合わせ、シール剤で周囲を接着して空セルを作製した。この空セルに減圧注入法によって、MLC−6608(メルク・ジャパン製)を注入し、注入口を封止して、アンチパラレル配向のネマティック液晶セルを得た。
上記の「液晶セルの作製」で得られた液晶セルについて、液晶注入後の初期、及び95℃5分加熱処理後に関して、プレチルト角測定装置PAS−301(ELSICON製)を用いて室温で測定した。また、各条件の液晶セルについて、偏光顕微鏡観察により液晶の配向均一性を確認した。いずれの液晶セルとも、ラビング処理に伴う削れや配向不良はなく、液晶は均一に配向していた。
合成例1で得られた樹脂固形分濃度24.9質量%のポリアミド酸溶液(1)(10.5g)、NMP(8.50g)、及びBCS(24.6g)を、25℃にて6時間混合して、液晶配向処理剤(1)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例2で得られたポリイミド粉末(2)(2.52g)、NMP(22.3g)、及びBCS(19.7g)を、25℃にて8時間混合して、液晶配向処理剤(2)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例3で得られたポリイミド粉末(3)(2.50g)、NMP(24.0g)、及びBCS(17.6g)を、25℃にて8時間混合して、液晶配向処理剤(3)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例4で得られたポリイミド粉末(4)(2.51g)、NMP(26.1g)、及びBCS(15.7g)を、25℃にて8時間混合して、液晶配向処理剤(4)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例5で得られたポリイミド粉末(5)(2.50g)、NMP(29.9g)、及びBCS(11.8g)を、25℃にて8時間混合して、液晶配向処理剤(5)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例6で得られた樹脂固形分濃度25.0質量%のポリアミド酸溶液(6)(11.0g)、NMP(11.1g)、及びBCS(23.7g)を、25℃にて6時間混合して、液晶配向処理剤(6)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例7で得られたポリイミド粉末(7)(2.51g)、NMP(30.0g)、及びBCS(11.8g)を、25℃にて8時間混合して、液晶配向処理剤(7)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例8で得られたポリイミド粉末(8)(2.50g)、NMP(26.0g)、及びBCS(15.7g)を、25℃にて8時間混合して、液晶配向処理剤(8)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例9で得られたポリイミド粉末(9)(2.50g)、NMP(31.9g)、及びBCS(9.80g)を、25℃にて8時間混合して、液晶配向処理剤(9)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例10で得られたポリイミド粉末(10)(2.53g)、NMP(30.3g)、及びBCS(11.9g)を、25℃にて8時間混合して、液晶配向処理剤(10)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例2で得られたポリイミド粉末(2)(2.50g)、NMP(22.1g)、BCS(19.6g)、及び架橋性化合物(1)(0.25g)を、25℃にて12時間混合し、液晶配向処理剤(11)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例3で得られたポリイミド粉末(3)(2.50g)、NMP(24.0g)、BCS(17.6g)、及び架橋性化合物(2)(0.50g)を、25℃にて12時間混合し、液晶配向処理剤(12)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例3で得られたポリイミド粉末(3)(2.51g)、NMP(24.1g)、BCS(17.7g)、及び架橋性化合物(3)(0.25g)を、25℃にて12時間混合し、液晶配向処理剤(13)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例11で得られた樹脂固形分濃度25.4質量%のポリアミド酸溶液(11)(10.0g)、NMP(8.50g)、及びBCS(23.9g)を、25℃にて6時間混合して、液晶配向処理剤(14)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例12で得られたポリイミド粉末(12)(2.50g)、NMP(22.1g)、及びBCS(19.6g)を、25℃にて8時間混合して、液晶配向処理剤(15)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例13で得られたポリイミド粉末(13)(2.51g)、NMP(24.1g)、及びBCS(17.7g)を、25℃にて8時間混合して、液晶配向処理剤(16)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例14で得られたポリイミド粉末(14)(2.50g)、NMP(22.1g)、及びBCS(19.6g)を、25℃にて8時間混合して、液晶配向処理剤(17)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
合成例15で得られたポリイミド粉末(15)(2.50g)、NMP(29.9g)、及びBCS(11.8g)を、25℃にて8時間混合して、液晶配向処理剤(18)を得た。この液晶配向処理剤に、濁りや析出などの異常は見られず、均一な溶液であることが確認された。
Claims (11)
- 下記の式[1]で示されるジアミン化合物、及び下記の式[2]で示されるジアミン化合物を含むジアミン成分とテトラカルボン酸二無水物とを反応させて得られる重合体を含有する液晶配向処理剤。
(式[1]中、X1は−NHCO−、−N(CH3)CO−、−CONH−、−CON(CH3)−より選ばれる2価の有機基であり、X2は単結合、ベンゼン環、又はシクロへキシル環より選ばれる2価の有機基であり、X3はベンゼン環、又はシクロへキシル環より選ばれる2価の有機基であり、X4はシクロへキシル環、又はベンゼン環より選ばれる2価の有機基であり、X5は炭素数1〜18のアルキル基、炭素数1〜18のフッ素含有アルキル基、炭素数1〜18のアルコキシル基、又は炭素数1〜18のフッ素含有アルコキシル基より選ばれ、nは1〜4の整数である)。
(式[2]中、Y1は−O−、−CH2O−、−(CH2)a−(aは1〜10の整数である)、−COO−、−OCO−、又は単結合より選ばれる2価の有機基であり、Y2は単結合、又は−(CH2)b−(bは1〜10の整数である)より選ばれる2価の有機基であり、Y3は単結合、−(CH2)c−(cは1〜10の整数である)、−O−、−CH2O−、−COO−、又は−OCO−より選ばれる2価の有機基であり、Y4はベンゼン環、シクロへキシル環、又は複素環から選ばれる2価の環状基、又は、ステロイド骨格を有する炭素数12〜25の2価の有機基を示し、前記環状基上の任意の水素原子は、炭素数1〜3のアルキル基、炭素数1〜3のアルコキシル基、炭素数1〜3のフッ素含有アルキル基、又は炭素数1〜3のフッ素含有アルコキシル基、フッ素原子から選ばれるもので置換されていても良く、Y5はシクロへキシル環、ベンゼン環、又は複素環から選ばれる2価の環状基を示し、これらの環状基上の任意の水素原子は、炭素数1〜3のアルキル基、炭素数1〜3のアルコキシル基、炭素数1〜3のフッ素含有アルキル基、又は炭素数1〜3のフッ素含有アルコキシル基、フッ素原子から選ばれるもので置換されていても良く、nは0〜4の整数であり、Y6は、炭素数1〜18のアルキル基、炭素数1〜18のフッ素含有アルキル基、炭素数1〜18のアルコキシル基、炭素数1〜18のフッ素含有アルコキシル基又は水素原子であり、mは1〜4の整数である)。 - 式[1]中、X1が−NHCO−である請求項1に記載の液晶配向処理剤。
- 液晶配向処理剤中に、エポキシ基、オキセタン基、イソシアネート基及びシクロカーボネート基からなる群より選ばれる少なくとも1種の置換基を有する架橋性化合物、ヒドロキシル基、ヒドロキシアルキル基、アルコキシル基及び低級アルコキシアルキル基からなる群より選ばれる少なくとも1種の置換基を有する架橋性化合物、又は重合性不飽和結合を有する架橋性化合物を有する請求項1〜請求項4のいずれか一項に記載の液晶配向処理剤。
- 液晶配向処理剤中の重合体がポリアミド酸を脱水閉環させて得られるポリイミドである請求項1〜請求項5のいずれか一項に記載の液晶配向処理剤。
- 液晶配向処理剤中に5〜60質量%の貧溶媒を含有する請求項1〜請求項6のいずれか一項に記載の液晶配向処理剤。
- 請求項1〜請求項7のいずれか一項に記載の液晶配向処理剤を用いて得られる液晶配向膜。
- 請求項8に記載の液晶配向膜を有する液晶表示素子。
- 請求項1〜請求項7のいずれか一項に記載の液晶配向処理剤を用いて得られる液晶配向膜であって、液晶に熱や紫外線照射により重合する重合性化合物を混合した液晶材料を用いて、液晶層に電圧を印加しながら前記重合性化合物を重合させて得られるポリマーで、駆動時の液晶の配向方向を制御する方法により得られる液晶表示素子に用いられる液晶配向膜。
- 請求項10に記載の液晶配向膜を具備する液晶表示素子であって、液晶に熱や紫外線照射により重合する重合性化合物を混合した液晶材料を用いて、液晶層に電圧を印加しながら前記重合性化合物を重合させて得られるポリマーで、駆動時の液晶の配向方向を制御する方法により得られる液晶表示素子。
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