JPH05119320A - Liquid crystal oriented film - Google Patents
Liquid crystal oriented filmInfo
- Publication number
- JPH05119320A JPH05119320A JP27919991A JP27919991A JPH05119320A JP H05119320 A JPH05119320 A JP H05119320A JP 27919991 A JP27919991 A JP 27919991A JP 27919991 A JP27919991 A JP 27919991A JP H05119320 A JPH05119320 A JP H05119320A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- liq
- crystal element
- crystal
- oriented film
- 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.)
- Pending
Links
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- Liquid Crystal (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、液晶配向膜に関する。
特に液晶素子の特性に影響する液晶分子の配向、ないし
液晶素子の表示の均一性に関する。FIELD OF THE INVENTION The present invention relates to a liquid crystal alignment film.
In particular, it relates to the alignment of liquid crystal molecules, which affects the characteristics of the liquid crystal element, or the display uniformity of the liquid crystal element.
【０００２】[0002]
【従来の技術】両基板の間隙に液晶組成物を充填して液
晶素子を得る。この際、一般的に使われる配向膜は、ポ
リイミド系単体から構成されることが多い。2. Description of the Related Art A liquid crystal device is obtained by filling a liquid crystal composition in a gap between both substrates. At this time, a commonly used alignment film is often made of a polyimide-based simple substance.
【０００３】なお、液晶分子の配向膜の概念は、佐々木
昭夫編、「液晶エレクトロニクスの基礎と応用」に詳し
い。The concept of an alignment film of liquid crystal molecules is detailed in "Basics and Applications of Liquid Crystal Electronics" edited by Akio Sasaki.
【０００４】[0004]
【発明が解決しようとする課題】ネマティック液晶素
子、強誘電性液晶素子において、表示の均一性等、液晶
分子の配向の均一性が問題となっている。In the nematic liquid crystal element and the ferroelectric liquid crystal element, the uniformity of the alignment of liquid crystal molecules, such as the uniformity of display, has been a problem.
【０００５】[0005]
【課題を解決するための手段】本発明は前述のような課
題を解決するために、対向する電極基板の間に液晶を封
入してなる液晶素子に設けられた液晶配向膜が、一般式
がAccording to the present invention, in order to solve the above-mentioned problems, a liquid crystal alignment film provided in a liquid crystal element in which liquid crystal is sealed between opposing electrode substrates has a general formula.
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】但し、Ｒ1、Ｒ2は、アルキル基、アルコキ
シ基、またはフェニル基であり、Ｒ 3、Ｒ4のうち一つは
水素、アルキル基、またはアルコキシ基であり、もう一
つは、トリフェニレン、ピレン、ベンゾピレン、ペリレ
ン、コロネン等の高次の芳香環からなる基からなるヒド
ラゾン系化合物を含むことを特徴とするものである。However, R1, R2Is an alkyl group, alkoxy
Si group or phenyl group, R 3, RFourOne of them
Hydrogen, an alkyl group, or an alkoxy group, another
One is triphenylene, pyrene, benzopyrene, perile
Of hydrazine, coronene and other high-order aromatic rings
It is characterized in that it contains a razone compound.
【０００８】[0008]
【作用】高次の芳香環からなる基が、かさ高く、これが
配向膜の表層近くにある時、液晶分子の並びは影響を受
けると想定される。これが、液晶分子の並びがより良化
される傾向をもっているようだ。When the group consisting of a higher order aromatic ring is bulky and is near the surface layer of the alignment film, it is assumed that the alignment of liquid crystal molecules is affected. This seems to tend to improve the alignment of liquid crystal molecules.
【０００９】また、高次の芳香環からなる基をヒドラゾ
ン化合物がもつ故に、液晶そのものへのヒドラゾン化合
物の溶解は検出し得ない。すなわち、優れた信頼性に直
結する。Further, since the hydrazone compound has a group consisting of a higher order aromatic ring, the dissolution of the hydrazone compound in the liquid crystal itself cannot be detected. That is, it is directly connected to excellent reliability.
【００１０】また、この種のより簡単な構造の化合物
は、電荷移動物質として使用されている。本発明のもの
も、このような効果が若干、期待されるかも知れない。
配向膜の電気抵抗を下げることが、不純物イオンの吸着
を妨げることが出来、素子の電圧−透過率特性の電圧閾
値を下げ得ること、強誘電性液晶素子の場合、配向が良
化すること、均一な液晶素子の表示が可能となること
等、望ましい。Further, compounds of this type having a simpler structure are used as charge transfer substances. The present invention may also be expected to have some such effects.
Lowering the electrical resistance of the alignment film can prevent the adsorption of impurity ions, can lower the voltage threshold of the voltage-transmittance characteristic of the device, in the case of a ferroelectric liquid crystal device, the alignment is improved, It is desirable that a uniform liquid crystal element can be displayed.
【００１１】特に、強誘電性液晶素子においては、液晶
中の不純物イオンの影響が大きい。この種イオンが配向
膜表面に吸着し、悪影響を及ぼすことがしばしばであ
る。これに対する対策が望まれる。若干、配向膜が低抵
抗になる可能性があることは、このような現象を考える
時、有利になると想定する。Particularly in a ferroelectric liquid crystal device, the influence of impurity ions in the liquid crystal is large. These seed ions are often adsorbed on the surface of the alignment film and have an adverse effect. Measures against this are desired. It is assumed that there is a possibility that the alignment film may have a low resistance, which is advantageous when considering such a phenomenon.
【００１２】[0012]
【実施例】以下、本発明の実施例を説明する。EXAMPLES Examples of the present invention will be described below.
【００１３】（実施例１）分子全体が(Example 1) The whole molecule
【００１４】[0014]
【化３】 [Chemical 3]
【００１５】で表されるヒドラゾン化合物を入手した。
これを、ノーマル・メティル・２ピロリドン（ＮＭＰ）
に溶解し、ＮＭＰ溶液を調整した。A hydrazone compound represented by: was obtained.
This is normal methyl 2 pyrrolidone (NMP)
To prepare an NMP solution.
【００１６】このＮＭＰ溶液と、窒素（株）から入手し
た、ハイティルト用ポリイミド用インク、ＰＳＩ−Ａ−
２２０４−Ｍ０１のＮＭＰ溶液を混合した。前記ポリイ
ミド樹脂分（現実にはポリアミック酸樹脂）と（化３）
に表される樹脂分の重量比を、４：１とし、しかも全樹
脂分のＮＭＰ溶液の濃度は２％とした。This NMP solution and a polyimide ink for high tilt, PSI-A-, obtained from Nitrogen Co., Ltd.
2204-M01 NMP solution was mixed. The polyimide resin component (actually polyamic acid resin) and (Chemical formula 3)
The weight ratio of the resin component represented by (4) was set to 4: 1 and the concentration of the NMP solution of all the resin components was set to 2%.
【００１７】パターニングされた透明導電電極を主面上
に有するガラス基板上に、この溶液を、スピナーで塗布
した。溶媒のＮＭＰを加熱、気化させて、有機膜を得
た。２種類の化合物に対して、２種類の有機膜を得た。This solution was applied by a spinner onto a glass substrate having a patterned transparent conductive electrode on the main surface. The solvent NMP was heated and vaporized to obtain an organic film. Two types of organic films were obtained for two types of compounds.
【００１８】この膜を、レーヨン繊維でラビングした。
この基板を使い、スーパー・ツウイスティッド・ネマテ
ィック（ＳＴＮ）パネルを公知の方法で製作した。この
あと、偏光板等を取り付け、表示特性を評価した。この
パネルにおいては、電圧−透過率特性の電圧閾値が１５
％下がり、表示もより均一であった。特にラビングの不
均一性が、表示においては従来より緩和された。The film was rubbed with rayon fiber.
Using this substrate, a Super Twisted Nematic (STN) panel was manufactured by a known method. After that, a polarizing plate or the like was attached and the display characteristics were evaluated. In this panel, the voltage threshold value of the voltage-transmittance characteristic is 15
%, And the display was more uniform. In particular, the nonuniformity of rubbing was alleviated in the display as compared with the conventional case.
【００１９】（実施例２）分子全体が（化３）で表され
るヒドラゾン化合物を入手した。これを、ノーマル・メ
ティル・２ピロリドン（ＮＭＰ）に溶解し、ＮＭＰ溶液
を調整した。(Example 2) A hydrazone compound whose entire molecule is represented by (Chemical Formula 3) was obtained. This was dissolved in normal methyl 2pyrrolidone (NMP) to prepare an NMP solution.
【００２０】これのＮＭＰ溶液と、東燃石油化学（株）
から入手した、ポリパラバン酸樹脂（商標ソルラック）
のＮＭＰ溶液を混合した。前記ポリパラバン酸樹脂分と
（化３）に表される樹脂分の重量比を、５：１とし、し
かも全樹脂分のＮＭＰ溶液の濃度は０．７％とした。NMP solution of this and Tonen Petrochemical Co., Ltd.
Polyparabanic acid resin (trademark Sollac) obtained from
Of NMP solution were mixed. The weight ratio of the polyparabanic acid resin component to the resin component represented by (Chemical Formula 3) was 5: 1, and the concentration of the NMP solution in the total resin component was 0.7%.
【００２１】この膜を、レーヨン繊維でラビングした。
この上に、０．００５ｗ％に希釈した、メルク社製垂直
配向剤、ＺＬＩ−３３３４（エタノール溶媒）をスピナ
ーで塗布、約１２０℃で３０分熱処理した。The film was rubbed with rayon fiber.
A vertical aligning agent ZLI-3334 (ethanol solvent) manufactured by Merck & Co., which was diluted to 0.005 w%, was applied onto this with a spinner and heat-treated at about 120 ° C for 30 minutes.
【００２２】この基板を使い、ＳＴＮパネルを公知の方
法で製作した。このあと、偏光板等を取り付け、表示特
性を評価した。このパネルにおいては、電圧−透過率特
性の電圧閾値が約１０％下がり、表示も均一であった。Using this substrate, an STN panel was manufactured by a known method. After that, a polarizing plate or the like was attached and the display characteristics were evaluated. In this panel, the voltage threshold of the voltage-transmittance characteristic was lowered by about 10%, and the display was uniform.
【００２３】なお、別の測定によれば、この基板に接す
る液晶分子のプレティルト角は約２５°であった。According to another measurement, the pretilt angle of liquid crystal molecules in contact with this substrate was about 25 °.
【００２４】また、この種の基板を用い、公知の方法
で、強誘電性液晶素子を製作した。全面、均一なユニフ
ォーム配向が得られた。電圧−透過率特性の電圧閾値特
性も、急峻であって、大容量マトリクス駆動が可能であ
った。また、信頼性も実用レベルにあった。Further, using this type of substrate, a ferroelectric liquid crystal element was manufactured by a known method. Uniform uniform orientation was obtained over the entire surface. The voltage threshold characteristic of the voltage-transmittance characteristic was also steep, and large-capacity matrix driving was possible. Also, the reliability was at a practical level.
【００２５】（実施例３）分子全体が(Example 3) The whole molecule
【００２６】[0026]
【化４】 [Chemical 4]
【００２７】で表されるヒドラゾン化合物を入手した。
これを、ノーマル・メティル・２ピロリドン（ＮＭＰ）
に溶解し、ＮＭＰ溶液を調整した。A hydrazone compound represented by: was obtained.
This is normal methyl 2 pyrrolidone (NMP)
To prepare an NMP solution.
【００２８】このＮＭＰ溶液と、窒素（株）から入手し
た、ハイティルト用ポリイミド用インク、ＰＳＩ−Ａ−
２２０４−Ｍ０１のＮＭＰ溶液を混合した。前記ポリイ
ミド樹脂分（現実にはポリアミック酸樹脂）と（化４）
に表される樹脂分の重量比を、４：１とし、しかも全樹
脂分のＮＭＰ溶液の濃度は２％とした。This NMP solution and a polyimide ink for high tilt, PSI-A-, obtained from Nitrogen Co., Ltd.
2204-M01 NMP solution was mixed. Polyimide resin component (actually polyamic acid resin) and (Chemical formula 4)
The weight ratio of the resin component represented by (4) was set to 4: 1 and the concentration of the NMP solution of all the resin components was set to 2%.
【００２９】パターニングされた透明導電電極を主面上
に有するガラス基板上に、この溶液を、スピナーで塗布
した。溶媒のＮＭＰを加熱、気化させて、有機膜を得
た。２種類の化合物に対して、２種類の有機膜を得た。This solution was applied to a glass substrate having a patterned transparent conductive electrode on the main surface by a spinner. The solvent NMP was heated and vaporized to obtain an organic film. Two types of organic films were obtained for two types of compounds.
【００３０】この膜を、レーヨン繊維でラビングした。
この基板を使い、スーパー・ツウイスティッド・ネマテ
ィック（ＳＴＮ）パネルを公知の方法で製作した。この
あと、偏光板等を取り付け、表示特性を評価した。この
パネルにおいては、電圧−透過率特性の電圧閾値が１５
％下がり、表示もより均一であった。特にラビングの不
均一性が、表示においては従来より緩和された。The film was rubbed with rayon fiber.
Using this substrate, a Super Twisted Nematic (STN) panel was manufactured by a known method. After that, a polarizing plate or the like was attached and the display characteristics were evaluated. In this panel, the voltage threshold value of the voltage-transmittance characteristic is 15
%, And the display was more uniform. In particular, the nonuniformity of rubbing was alleviated in the display as compared with the conventional case.
【００３１】（実施例４）分子全体が（化４）で表され
るヒドラゾン化合物を入手した。これを、ノーマル・メ
ティル・２ピロリドン（ＮＭＰ）に溶解し、ＮＭＰ溶液
を調整した。Example 4 A hydrazone compound whose entire molecule is represented by the formula (4) was obtained. This was dissolved in normal methyl 2pyrrolidone (NMP) to prepare an NMP solution.
【００３２】これのＮＭＰ溶液と、東燃石油化学（株）
から入手した、ポリパラバン酸樹脂（商標ソルラック）
のＮＭＰ溶液を混合した。前記ポリパラバン酸樹脂分と
（化４）に表される樹脂分の重量比を、５：１とし、し
かも全樹脂分のＮＭＰ溶液の濃度は０．７％とした。NMP solution of this and Tonen Petrochemical Co., Ltd.
Polyparabanic acid resin (trademark Sollac) obtained from
Of NMP solution were mixed. The weight ratio of the polyparabanic acid resin component to the resin component represented by (Chemical Formula 4) was 5: 1, and the concentration of the NMP solution of the total resin component was 0.7%.
【００３３】この膜を、レーヨン繊維でラビングした。
この上に、０．００５ｗ％に希釈した、メルク社製垂直
配向剤、ＺＬＩ−３３３４（エタノール溶媒）をスピナ
ーで塗布、約１２０℃で３０分熱処理した。The film was rubbed with rayon fiber.
A vertical aligning agent ZLI-3334 (ethanol solvent) manufactured by Merck & Co., which was diluted to 0.005 w%, was applied onto this with a spinner and heat-treated at about 120 ° C for 30 minutes.
【００３４】この基板を使い、ＳＴＮパネルを公知の方
法で製作した。このあと、偏光板等を取り付け、表示特
性を評価した。このパネルにおいては、電圧−透過率特
性の電圧閾値が約１０％下がり、表示も均一であった。Using this substrate, an STN panel was manufactured by a known method. After that, a polarizing plate or the like was attached and the display characteristics were evaluated. In this panel, the voltage threshold of the voltage-transmittance characteristic was lowered by about 10%, and the display was uniform.
【００３５】なお、別の測定によれば、この基板に接す
る液晶分子のプレティルト角は約２５°であった。According to another measurement, the pretilt angle of liquid crystal molecules in contact with this substrate was about 25 °.
【００３６】また、この種の基板を用い、公知の方法
で、強誘電性液晶素子を製作した。全面、均一なユニフ
ォーム配向が得られた。電圧−透過率特性の電圧閾値特
性も、急峻であって、大容量マトリクス駆動が可能であ
った。また、信頼性も実用レベルにあった。Further, using this type of substrate, a ferroelectric liquid crystal element was manufactured by a known method. Uniform uniform orientation was obtained over the entire surface. The voltage threshold characteristic of the voltage-transmittance characteristic was also steep, and large-capacity matrix driving was possible. Also, the reliability was at a practical level.
【００３７】なお、Incidentally,
【００３８】[0038]
【化５】 [Chemical 5]
【００３９】に示された化合物、A compound represented by
【００４０】[0040]
【化６】 [Chemical 6]
【００４１】示された化合物を入手した。これは一般に
電荷移動物質としてよく使われているものである。The indicated compound was obtained. This is commonly used as a charge transfer material.
【００４２】これを、実施例と同様にして、ＳＴＮパネ
ルや、強誘電性液晶パネルを作製した。液晶分子の並び
や、特性、パネルの信頼性はやや不満足なものであっ
た。用途によっては使用可能であるが。An STN panel and a ferroelectric liquid crystal panel were produced in the same manner as in the example. The alignment of liquid crystal molecules, characteristics, and panel reliability were somewhat unsatisfactory. It can be used depending on the application.
【００４３】以上、本発明は、直接には、電荷移動物質
の性質には、ほとんど依存していないことが理解され
る。From the above, it can be understood that the present invention is not directly dependent on the properties of the charge transfer material.
【００４４】[0044]
【発明の効果】以上本発明は、優れた配向膜を提案する
ものであり、優れた液晶素子を得ることが出来、産業に
貢献するところ大である。As described above, the present invention proposes an excellent alignment film, and it is possible to obtain an excellent liquid crystal element, which greatly contributes to the industry.
Claims (1)
なる液晶素子に設けられた液晶配向膜が、一般式が 【化１】 但し、Ｒ1、Ｒ2は、アルキル基、アルコキシ基、または
フェニル基であり、Ｒ 3、Ｒ4のうち一つは水素、アルキ
ル基、またはアルコキシ基であり、もう一つは、トリフ
ェニレン、ピレン、ベンゾピレン、ペリレン、コロネン
等の高次の芳香環からなる基からなるヒドラゾン系化合
物を含むことを特徴とする液晶配向膜。1. A liquid crystal is sealed between opposing electrode substrates.
The liquid crystal alignment film provided on the liquid crystal element has a general formula:However, R1, R2Is an alkyl group, an alkoxy group, or
A phenyl group, R 3, RFourOne of them is hydrogen, Archi
Group is an alkoxy group or an alkoxy group.
Enylene, pyrene, benzopyrene, perylene, coronene
Hydrazone compounds consisting of groups consisting of higher aromatic rings such as
A liquid crystal alignment film containing a substance.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27919991A JPH05119320A (en) | 1991-10-25 | 1991-10-25 | Liquid crystal oriented film |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27919991A JPH05119320A (en) | 1991-10-25 | 1991-10-25 | Liquid crystal oriented film |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05119320A true JPH05119320A (en) | 1993-05-18 |
Family
ID=17607818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27919991A Pending JPH05119320A (en) | 1991-10-25 | 1991-10-25 | Liquid crystal oriented film |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05119320A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6046791A (en) * | 1995-11-10 | 2000-04-04 | Seiko Epson Corporation | Polymer dispersed liquid crystal electro-optical device and method for manufacturing the same |
| WO2013085315A1 (en) * | 2011-12-06 | 2013-06-13 | 주식회사 엘지화학 | Liquid crystal cell |
| CN103988121A (en) * | 2011-12-06 | 2014-08-13 | 株式会社Lg化学 | Liquid crystal cell |
-
1991
- 1991-10-25 JP JP27919991A patent/JPH05119320A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6046791A (en) * | 1995-11-10 | 2000-04-04 | Seiko Epson Corporation | Polymer dispersed liquid crystal electro-optical device and method for manufacturing the same |
| WO2013085315A1 (en) * | 2011-12-06 | 2013-06-13 | 주식회사 엘지화학 | Liquid crystal cell |
| CN103988121A (en) * | 2011-12-06 | 2014-08-13 | 株式会社Lg化学 | Liquid crystal cell |
| TWI480636B (en) * | 2011-12-06 | 2015-04-11 | Ｌｇ化學股份有限公司 | Liquid crystal cell |
| US9182624B2 (en) | 2011-12-06 | 2015-11-10 | Lg Chem, Ltd. | Liquid crystal cell |
| US9588369B2 (en) | 2011-12-06 | 2017-03-07 | Lg Chem, Ltd. | Liquid crystal cell |
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