JPH054649B2 - - Google Patents
Info
- Publication number
- JPH054649B2 JPH054649B2 JP1590186A JP1590186A JPH054649B2 JP H054649 B2 JPH054649 B2 JP H054649B2 JP 1590186 A JP1590186 A JP 1590186A JP 1590186 A JP1590186 A JP 1590186A JP H054649 B2 JPH054649 B2 JP H054649B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- degrees
- tilt angle
- polymer
- display element
- 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.)
- Expired - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 47
- 229920000642 polymer Polymers 0.000 claims description 10
- 229920002647 polyamide Polymers 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- 239000004642 Polyimide Substances 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 239000004962 Polyamide-imide Substances 0.000 claims description 2
- 229920002312 polyamide-imide Polymers 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000002966 varnish Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- -1 diamine compound Chemical class 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- KSFBTBXTZDJOHO-UHFFFAOYSA-N diaminosilicon Chemical compound N[Si]N KSFBTBXTZDJOHO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
Classifications
-
- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
-
- 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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- 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
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
-
- 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
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/139—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on orientation effects in which the liquid crystal remains transparent
- G02F1/1396—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on orientation effects in which the liquid crystal remains transparent the liquid crystal being selectively controlled between a twisted state and a non-twisted state, e.g. TN-LC cell
- G02F1/1397—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on orientation effects in which the liquid crystal remains transparent the liquid crystal being selectively controlled between a twisted state and a non-twisted state, e.g. TN-LC cell the twist being substantially higher than 90°, e.g. STN-, SBE-, OMI-LC cells
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Liquid Crystal (AREA)
- Nonlinear Science (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Mathematical Physics (AREA)
Description
〔産業上の利用分野〕
本発明は、200度から250度の範囲でねじれたら
旋構造を有する液晶の配向制御膜に係り、特にス
キヤツタリングドメインの発生しない好適な液晶
素子に関する。
〔従来の技術〕
従来のツイステツドネマチツク（TN）モード
の液晶素子においては、２枚の電極基板間で液晶
分子を90度ねじつて配向膜としてSiOの斜方蒸着
及びポリイミド系の材料が主に用いられている。
しかし、このモードでは時分割特性を飛躍的に向
上させることは難しく、今後大容量のデイスプレ
イを得ることは期待ができない。
一方、近年になり液晶分子を270度ねじつて配
向させるスーパーツイスト複屈折効果（SBE）
を用いた液晶素子の発表がSIDインターナシヨナ
ルシンポジウム、（PP120−123，1985）で成さ
れ、更には日経エレクトロニツクス（1985.8.26）
でも論じられ液晶の新たな応用分野を拓くものと
して期待されている。
ところで、SBE液晶素子のように液晶のねじ
れ（ツイスト）角を従来の90度に比べてはるかに
大きくした、例えば270度近くの素子に対しては、
従来のようなチルト角の小さいラビングによる配
向制御膜ではスキヤツタリングドメイン（光を散
乱するドメイン）が発生し、正常な動作は不可能
である。このスキヤツタリングドメインを防止す
るには配向制御膜のチルト角を大きくする以外の
今のところ方法はないが、斜方蒸着法ではバツチ
式の方法でもあり量産性に難があり、是非共チル
ト角を今までよりも大きくした有機高分子膜のラ
ビング法で可能な技術を実現することが重要な課
題になつている。
〔発明が解決しようとする問題点〕
上記従来技術のネマチツク液晶については、
TNモードに用いる配向制御膜は配向膜のチルト
角が小さくなるに従い時分割特性が向上する。し
たがつて、TNモードでは配向膜のチルト角が約
３度以下の膜材料を用いて製品化を行つているの
が現状である。しかし、SBEモードではTNモー
ドと相反して配向制御膜のチルト角が大きくない
とスキヤツタリングドメインが発生し正常な動作
を示さないという問題があつた。
本発明の目的は、SBE液晶素子のように液晶
のねじれ角を従来の90度に比べてはるかに大きく
した素子においても、チルト角の大きい有機高分
子材料のラビング法で可能な配向制御膜を用いる
ことにより、スキヤツタリングドメインが発生し
ない量産性に適した液晶素子を提供することにあ
る。
〔問題点を解決するための手段〕
本発明を概説すれば、本発明は液晶表示素子に
関する発明であつて、少なくとも一方は透光性の
電極を有する基板間に、正の誘電異方性を示し、
旋光性物質が添加されたネマチツク液晶が200度
から250度の範囲でねじれたら旋構造を有する液
晶を挾持した液晶素子において、該電極と液晶相
の間に、主鎖に炭素数８〜18のアルキレン基を含
むポリマー系の配向制御膜をラビングして用いた
ことを特徴とする。
前記した目的を達成するために本発明による液
晶表示素子は、液晶分子のら旋構造のねじれ角を
200度から250度の範囲とし、有機高分子材料を用
いてTNモード方式と同様にラビング法で可能な
チルト角の大きい配向制御膜を得る目的で、種々
の高分子膜及び無機膜等鋭意検討を進めた結果、
ある特定の含長鎖炭化水素ポリマーを用いた場
合、量産性に適したスキヤツタリングドメインの
発生しない均一配向性の可能な配向制御膜を見出
し、本発明に至つたものである。
本発明は特にSBE液晶素子に関する発明であ
つて、基板、電界印加手段、配向制御層及びネマ
チツク液晶層を包含する液晶素子において、該配
向制御層が、主鎖に炭素数８〜18のアルキレン基
を含むポリマー系の高分子膜で構成され、表示素
子、光変調素子、その他、用途のいかんにかかわ
らずデイスプレイとしてすべて用いることが可能
である。
該主鎖に炭素数８〜18のアルキレン基を含むポ
リマーは、３度以上のチルト角を有するものが好
適である。その例としては、ポリイミド系、ポリ
イミドシロキサン系、ポリイミドイソインドロキ
ナゾリン系、ポリヒドラジドイミド系、ポリアミ
ドイミド系又はポリアミド系のポリマーが挙げら
れる。
例えば、ジアミン化合物及び二塩基酸ヒドラジ
ド化合物等をテトラカルボン酸無水物及び二塩基
酸ハロゲン化合物と重縮合したものである。ま
た、重縮合したポリマー系同志をブレンドしても
良く、シランカツプリング剤及びBiO2，Al2O3，
TiO2等と併用させても可能である。また、配向
制御膜の形成に関しては、TNモード方式と同様
に一般的な浸漬法、回転塗布法、スプレー法、印
刷法などが用いられラビングして配向制御膜を得
る。
〔実施例〕
以下、本発明を実施例により更に具体的に説明
するが、本発明はこれら実施例に限定されない。
実施例 １
表１に示す長鎖のジヒドラジド化合物とピロメ
リツト酸二無水物をＮ−メチル−２−ピロリドン
溶液中で重縮合させて、得られたポリヒドラジド
酸ワニスを塗布後、300℃焼成を行い800Åのポリ
ヒドラジドイミド膜を作製した。その後、液晶分
子のねじれ角を220度にするために、上側電極基
板、下側電極基板をそれぞれの角度でラビングを
行い、更に基板間にスペーサーを挾持して8μｍ
ギヤツプの液晶セルを組立て、ビフエニル系液
晶、エステルシクロヘキサン（ECH）及びフエ
ニルシクロヘキサン（PCH）系液晶を主成分と
するネマチツク液晶に旋光性物質（メルク社の
S811）を0.5重量％添加した液晶材料を真空封入
し、素子作製を行つた。その後、上側偏光板の吸
収軸方向及び下側偏光板の吸収軸方向を調製しス
キヤツタリングドメイン（光を散乱するドメイ
ン）の有無を調べた。なお、上記の配向膜材料に
ついて別途通常の回転法を用いてHe−Neレーザ
で配向膜のチルト角を調べた。その結果について
まとめて表１に示す。
実施例 ２
表１に示す長鎖のジヒドラジド化合物と通常の
４，4′−ジアミノジフエニルエーテルを３，3′，
４，4′−ビフエニルテトラカルボン酸二無水物と
溶媒中で共重合させて得たポリヒドラジド酸−ア
ミド酸ワニスを塗布後、350℃焼成を行い500Åの
ポリヒドラジドイミド−イミド膜を作製した。そ
の後、液晶分子のねじれ角を240度になるよう実
施例１と同様にラビング、液晶材料及び偏光板の
調製を行いスキヤツタリングドメインの有無と上
記で用いた配向膜のチルト角を調べた。その結果
を表１に示す。
実施例 ３
表１に示す長鎖のジアミン化合物とイソフタル
酸クロライドを溶媒中で重合させて得たポリアミ
ドワニスを塗布後、250℃焼成を行い600Åのポリ
アミド膜を作製した。その後、液晶分子のねじれ
角を200度になるよう実施例１と同様にラビング、
液晶材料及び偏光板の調製を行いスキヤツタリン
グドメインの有無と上記で用いた配向膜のチルト
角を調べた。その結果を表１に示す。
実施例 ４
表１に示す長鎖のジヒドラジド化合物と通常の
４，4′−ジアミノジフエニルエーテル−３−カル
ボンアミドを３，3′，４，4′−ベンゾフエノンテ
トラカルボン酸二無水物と溶媒中で共重合させて
得たポリヒドラジド酸−アミド酸ワニスを塗布
後、300℃焼成を行い800Åのポリヒドラジド−イ
ミド−イソインドロキナゾリンジオン膜を作製し
た。その後、液晶分子のねじれ角を230度になる
よう実施例１と同様にラビング、液晶材料及び偏
光板の調製を行いスキヤツタリングドメインの有
無と上記で用いた配向膜のチルト角を調べた。そ
の結果を表１に示す。
実施例 ５
表１に示す長鎖のジヒドラジド化合物と通常の
ジアミノシランを３，3′，４，4′−ビフエニルテ
トラカルボン酸二無水物と溶媒中で共重合させて
得たポリヒドラジド酸−アミド酸シロキサンワニ
スを塗布後、350℃焼成を行い1000Åのポリヒド
ラジドイミド−イミドシロキサン膜を作製した。
その後、液晶分子のねじれ角を250度になるよう
実施例１と同様にラビング、液晶材料及び偏光板
の調製を行いスキヤツタリングドメインの有無と
上記で用いた配向膜のチルト角を調べた。その結
果を表１に示す。
実施例 ６
表１に示す長鎖のジアミン化合物とピロメリツ
ト酸二無水物を溶媒中で重合させて得たポリアミ
ド酸ワニスを塗布後、200℃焼成を行い300Åのポ
リアミド膜を作製した。その後、液晶分子のねじ
れ角を200度になるよう実施例１と同様にラビン
グ、液晶材料及び偏光板の調製を行いスキヤツタ
リングドメインの有無と上記で用いた配向膜のチ
ルト角を調べた。その結果を表１に示す。
実施例 ７
表１に示す長鎖のジヒドラジド化合物と３，
3′，４，4′−ビフエニルテトラカルボン酸二無水
物及びイソフタル酸クロライドを溶媒中で重合さ
せて得たポリヒドラジド酸−アミドワニスを塗布
後、250℃焼成を行い800Åのポリヒドラジドイミ
ド−アミド膜を作製した。その後、液晶分子のね
じれ角を220度になるよう実施例１と同様にラビ
ング、液晶材料及び偏光板の調製を行いスキヤツ
タリングドメインの有無と上記で用いた配向膜の
チルト角を調べた。その結果を表１に示す。
比較例 １
表１に示す通常の４，4′−ジアミノジフエニル
エーテル化合物とピロメリツト酸二無水物を溶媒
中で重合させて得たポリアミド酸ワニスを塗布
後、250℃焼成を行い800Åのポリイミド膜を作製
した。その後、液晶分子のねじれ角を220度にな
るよう実施例１と同様にラビング、液晶材料及び
偏光板の調製を行いスキヤツタリングドメインの
有無と上記で用いた配向膜のチルト角を調べた。
その結果を表１に示す。
比較例 ２
表１に示す通常の４，4′−ジ（ｐ−アミノフエ
ノキシ）−２，２−ジフエニルプロパン化合物と
イソフタル酸クロライドを溶媒中で重合させて得
たポリアミドワニスを塗布後、200℃焼成を行い
600Åのポリアミド膜を作製した。その後、液晶
分子のねじれ角を200度になるよう実施例１と同
様にラビング、液晶材料及び偏光板の調製を行い
スキヤツタリングドメインの有無と上記で用いた
配向膜のチルト角を調べた。その結果を表１に示
す。
[Industrial Application Field] The present invention relates to a liquid crystal alignment control film having a helical structure twisted in the range of 200 to 250 degrees, and particularly to a suitable liquid crystal element in which scattering domains do not occur. [Conventional technology] In conventional twisted nematic (TN) mode liquid crystal devices, liquid crystal molecules are twisted 90 degrees between two electrode substrates to form an alignment film using oblique evaporation of SiO and polyimide material. Mainly used.
However, in this mode, it is difficult to dramatically improve the time division characteristics, and we cannot expect to obtain large-capacity displays in the future. On the other hand, in recent years, the supertwist birefringence effect (SBE), which twists and aligns liquid crystal molecules by 270 degrees, has been introduced.
A presentation of a liquid crystal device using the same technology was made at the SID International Symposium (PP120-123, 1985), and also at Nikkei Electronics (August 26, 1985).
However, it is expected to open up new fields of application for liquid crystals. By the way, for devices such as SBE liquid crystal devices, where the twist angle of the liquid crystal is much larger than the conventional 90 degrees, for example close to 270 degrees,
In the conventional alignment control film formed by rubbing with a small tilt angle, scattering domains (domains that scatter light) occur, making normal operation impossible. There is currently no way to prevent this scattering domain other than increasing the tilt angle of the alignment control film, but since the oblique evaporation method is also a batch method and mass production is difficult, it is definitely possible to An important issue is to realize a technology that is possible using the rubbing method for organic polymer films with larger corners than ever before. [Problems to be solved by the invention] Regarding the nematic liquid crystal of the above-mentioned prior art,
The time-sharing characteristics of the alignment control film used in TN mode improve as the tilt angle of the alignment film becomes smaller. Therefore, in the TN mode, the current situation is to commercialize alignment films using film materials with a tilt angle of about 3 degrees or less. However, in SBE mode, contrary to TN mode, there was a problem in that unless the tilt angle of the alignment control film was large, scattering domains would occur and normal operation would not occur. The purpose of the present invention is to create an alignment control film that is possible by rubbing an organic polymer material with a large tilt angle, even in devices such as SBE liquid crystal devices in which the twist angle of the liquid crystal is much larger than the conventional 90 degrees. By using the present invention, it is an object of the present invention to provide a liquid crystal element suitable for mass production in which scattering domains do not occur. [Means for Solving the Problems] To summarize the present invention, the present invention relates to a liquid crystal display element, and the present invention relates to a liquid crystal display element, in which positive dielectric anisotropy is created between substrates, at least one of which has a transparent electrode. show,
When a nematic liquid crystal to which an optically active substance is added is twisted in the range of 200 to 250 degrees, in a liquid crystal element that sandwiches a liquid crystal having a rotary structure, a structure having a carbon number of 8 to 18 in the main chain is placed between the electrode and the liquid crystal phase. It is characterized by using a polymer-based alignment control film containing an alkylene group by rubbing. In order to achieve the above object, the liquid crystal display element according to the present invention has a twist angle of the helical structure of liquid crystal molecules.
In order to obtain an orientation control film with a large tilt angle in the range of 200 to 250 degrees, which can be achieved by the rubbing method similar to the TN mode method using organic polymer materials, we are actively investigating various polymer films and inorganic films. As a result of proceeding with
When a certain long-chain hydrocarbon polymer is used, an orientation control film that is suitable for mass production and that does not generate scattering domains and can achieve uniform orientation has been discovered, leading to the present invention. The present invention particularly relates to an SBE liquid crystal element, which includes a substrate, an electric field applying means, an alignment control layer, and a nematic liquid crystal layer, in which the alignment control layer has an alkylene group having 8 to 18 carbon atoms in the main chain. It is composed of a polymer-based polymer film containing , and can be used as a display element, a light modulation element, or any other display regardless of its purpose. The polymer containing an alkylene group having 8 to 18 carbon atoms in its main chain preferably has a tilt angle of 3 degrees or more. Examples thereof include polyimide-based, polyimidosiloxane-based, polyimideisoindoroquinazoline-based, polyhydrazidoimide-based, polyamide-imide-based, or polyamide-based polymers. For example, it is a product obtained by polycondensing a diamine compound, a dibasic acid hydrazide compound, etc. with a tetracarboxylic acid anhydride and a dibasic acid halogen compound. Furthermore, polycondensed polymers may be blended together, such as a silane coupling agent and BiO 2 , Al 2 O 3 ,
It is also possible to use it in combination with TiO 2 etc. Regarding the formation of the orientation control film, similar to the TN mode method, a general dipping method, spin coating method, spray method, printing method, etc. are used, and the orientation control film is obtained by rubbing. [Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples. Example 1 A long-chain dihydrazide compound shown in Table 1 and pyromellitic dianhydride were polycondensed in an N-methyl-2-pyrrolidone solution, and the resulting polyhydrazidic acid varnish was applied and then baked at 300°C. An 800 Å polyhydrazide imide film was fabricated. After that, in order to make the twist angle of the liquid crystal molecules 220 degrees, the upper electrode substrate and the lower electrode substrate were rubbed at different angles, and a spacer was further sandwiched between the substrates to make the twist angle 8 μm.
Gap's liquid crystal cell was assembled, and an optically active substance (Merck's
A liquid crystal material containing 0.5% by weight of S811) was vacuum-sealed to fabricate a device. Thereafter, the absorption axis direction of the upper polarizing plate and the absorption axis direction of the lower polarizing plate were adjusted to examine the presence or absence of scattering domains (domains that scatter light). Note that the tilt angle of the alignment film of the above-mentioned alignment film material was separately investigated using a He--Ne laser using a normal rotation method. The results are summarized in Table 1. Example 2 The long-chain dihydrazide compound shown in Table 1 and ordinary 4,4'-diaminodiphenyl ether were mixed into 3,3',
After applying a polyhydrazidic acid-amic acid varnish obtained by copolymerizing with 4,4'-biphenyltetracarboxylic dianhydride in a solvent, it was baked at 350°C to produce a 500 Å polyhydrazidoimide-imide film. . Thereafter, rubbing was performed in the same manner as in Example 1, and the liquid crystal material and polarizing plate were prepared so that the twist angle of the liquid crystal molecules was 240 degrees, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were investigated. The results are shown in Table 1. Example 3 A polyamide varnish obtained by polymerizing a long-chain diamine compound shown in Table 1 and isophthalic acid chloride in a solvent was applied, and then baked at 250°C to produce a 600 Å polyamide film. After that, rubbing was performed in the same manner as in Example 1 so that the twist angle of the liquid crystal molecules was 200 degrees.
A liquid crystal material and a polarizing plate were prepared, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were investigated. The results are shown in Table 1. Example 4 The long-chain dihydrazide compound shown in Table 1 and ordinary 4,4'-diaminodiphenyl ether-3-carbonamide were combined with 3,3',4,4'-benzophenonetetracarboxylic dianhydride. After applying a polyhydrazide acid-amic acid varnish obtained by copolymerization in a solvent, baking was performed at 300°C to produce an 800 Å polyhydrazide-imide-isoindoquinazolinedione film. Thereafter, rubbing was performed in the same manner as in Example 1, and the liquid crystal material and polarizing plate were prepared so that the twist angle of the liquid crystal molecules was 230 degrees, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were investigated. The results are shown in Table 1. Example 5 Polyhydrazide acid obtained by copolymerizing the long-chain dihydrazide compound shown in Table 1 and ordinary diaminosilane with 3,3',4,4'-biphenyltetracarboxylic dianhydride in a solvent. After applying the amic acid siloxane varnish, baking was performed at 350°C to produce a 1000 Å polyhydrazidoimide-imidosiloxane film.
Thereafter, rubbing was carried out in the same manner as in Example 1 so that the twist angle of the liquid crystal molecules was 250 degrees, and the liquid crystal material and polarizing plate were prepared, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were investigated. The results are shown in Table 1. Example 6 A polyamide acid varnish obtained by polymerizing the long-chain diamine compound shown in Table 1 and pyromellitic dianhydride in a solvent was applied, and then baked at 200°C to produce a 300 Å polyamide film. Thereafter, rubbing was performed in the same manner as in Example 1, and the liquid crystal material and polarizing plate were prepared so that the twist angle of the liquid crystal molecules was 200 degrees, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were investigated. The results are shown in Table 1. Example 7 A long chain dihydrazide compound shown in Table 1 and 3,
After coating a polyhydrazide acid-amide varnish obtained by polymerizing 3',4,4'-biphenyltetracarboxylic dianhydride and isophthalic acid chloride in a solvent, it was baked at 250°C to form a polyhydrazide imide-amide of 800 Å. A membrane was prepared. Thereafter, rubbing was carried out in the same manner as in Example 1, and the liquid crystal material and polarizing plate were prepared so that the twist angle of the liquid crystal molecules was 220 degrees, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were investigated. The results are shown in Table 1. Comparative Example 1 After applying a polyamic acid varnish obtained by polymerizing the usual 4,4'-diaminodiphenyl ether compound and pyromellitic dianhydride shown in Table 1 in a solvent, baking was performed at 250°C to form an 800 Å polyimide film. was created. Thereafter, rubbing was performed in the same manner as in Example 1, and the liquid crystal material and polarizing plate were prepared so that the twist angle of the liquid crystal molecules was 220 degrees, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were examined.
The results are shown in Table 1. Comparative Example 2 After applying a polyamide varnish obtained by polymerizing the usual 4,4'-di(p-aminophenoxy)-2,2-diphenylpropane compound shown in Table 1 and isophthalic acid chloride in a solvent, the temperature was 200°C. Perform firing
A 600 Å polyamide membrane was fabricated. Thereafter, rubbing was carried out in the same manner as in Example 1 so that the twist angle of the liquid crystal molecules was 200 degrees, and the liquid crystal material and polarizing plate were prepared, and the presence or absence of scattering domains and the tilt angle of the alignment film used above were investigated. The results are shown in Table 1.
【表】【table】
【表】【table】
【表】【table】
以上説明したように本発明によれば、液晶のね
じれ角が200度から250度範囲内でのSBEモード
の液晶素子についても、従来の配向膜よりもチル
ト角の大きい配向制御膜を達成することができる
ので、TNモード方式と同様にラビング法を適用
してもスキヤツタリングドメインの発生が無く、
量産性に適した液晶表示素子が可能になるという
顕著な効果が奏せられる。
As explained above, according to the present invention, it is possible to achieve an alignment control film with a larger tilt angle than conventional alignment films even for SBE mode liquid crystal elements in which the twist angle of the liquid crystal is within the range of 200 degrees to 250 degrees. Therefore, even if the rubbing method is applied like the TN mode method, there is no scattering domain.
This has the remarkable effect of making it possible to create a liquid crystal display element suitable for mass production.
Claims (1)
間に、正の誘電異方性を示し、旋光性物質が添加
されたネマチツク液晶が200度から250度の範囲で
ねじれたら旋構造を有する液晶を挟持した液晶素
子において、該電極と液晶相の間に、主鎖に炭素
数８〜18のアルキレン基を含むポリマー系の配向
制御膜をラビングして用いたことを特徴とする液
晶表示素子。 ２ 該主鎖に炭素数８〜18のアルキレン基を含む
ポリマーは、３度以上のチルト角を有するもので
ある特許請求の範囲第１項記載の液晶表示素子。 ３ 該主鎖に炭素数８〜18のアルキレン基を含む
ポリマーが、ポリイミド系、ポリイミドシロキサ
ン系、ポリイミドイソインドロキナゾリン系、ポ
リヒドラジドイミド系、ポリアミドイミド系又は
ポリアミド系のポリマーである特許請求の範囲第
１項又は第２項記載の液晶表示素子。[Claims] 1. When a nematic liquid crystal exhibiting positive dielectric anisotropy and doped with an optically active substance is twisted between 200 degrees and 250 degrees between substrates, at least one of which has a transparent electrode. In a liquid crystal element sandwiching a liquid crystal having a circular structure, a polymer alignment control film containing an alkylene group having 8 to 18 carbon atoms in the main chain is rubbed between the electrode and the liquid crystal phase. LCD display element. 2. The liquid crystal display element according to claim 1, wherein the polymer containing an alkylene group having 8 to 18 carbon atoms in its main chain has a tilt angle of 3 degrees or more. 3. A patent claim in which the polymer containing an alkylene group having 8 to 18 carbon atoms in the main chain is a polyimide-based, polyimidosiloxane-based, polyimidoisoindoquinazoline-based, polyhydrazidoimide-based, polyamideimide-based, or polyamide-based polymer. A liquid crystal display element according to range 1 or 2.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61015901A JPS62174724A (en) | 1986-01-29 | 1986-01-29 | liquid crystal display element |
| EP87100473A EP0231781B1 (en) | 1986-01-22 | 1987-01-15 | Liquid crystal display element |
| DE8787100473T DE3777844D1 (en) | 1986-01-22 | 1987-01-15 | LIQUID CRYSTAL DISPLAY ELEMENT. |
| KR1019870000494A KR900005862B1 (en) | 1986-01-22 | 1987-01-22 | Liquid crystal display |
| US07/005,899 US4781439A (en) | 1986-01-22 | 1987-01-22 | Liquid crystal polyimide alignment free of scattering domains |
| US07/905,407 USRE34885E (en) | 1986-01-22 | 1992-06-29 | Liquid crystal polyimide alignment free of scattering domains |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61015901A JPS62174724A (en) | 1986-01-29 | 1986-01-29 | liquid crystal display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62174724A JPS62174724A (en) | 1987-07-31 |
| JPH054649B2 true JPH054649B2 (en) | 1993-01-20 |
Family
ID=11901679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61015901A Granted JPS62174724A (en) | 1986-01-22 | 1986-01-29 | liquid crystal display element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62174724A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2780183B2 (en) * | 1989-02-27 | 1998-07-30 | セイコーエプソン株式会社 | Alignment film and liquid crystal device |
-
1986
- 1986-01-29 JP JP61015901A patent/JPS62174724A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62174724A (en) | 1987-07-31 |
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