JPH04235939A - Acetylene derivative, liquid crystal composition containing the same and liquid crystal display element produced by using the composition - Google Patents
Acetylene derivative, liquid crystal composition containing the same and liquid crystal display element produced by using the compositionInfo
- Publication number
- JPH04235939A JPH04235939A JP431491A JP431491A JPH04235939A JP H04235939 A JPH04235939 A JP H04235939A JP 431491 A JP431491 A JP 431491A JP 431491 A JP431491 A JP 431491A JP H04235939 A JPH04235939 A JP H04235939A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal display
- acetylene derivative
- display element
- trans
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 79
- 150000000475 acetylene derivatives Chemical class 0.000 title claims abstract description 20
- 239000000203 mixture Substances 0.000 title claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 27
- 150000001875 compounds Chemical class 0.000 abstract description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 abstract description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 description 23
- 239000012071 phase Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 5
- 230000010287 polarization Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AHAZEMSUUYFDMM-JOCQHMNTSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(O)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(O)C=C1 AHAZEMSUUYFDMM-JOCQHMNTSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は液晶表示装置に用いられ
る液晶組成物の成分として有用なアセチレン誘導体、そ
れを含有する液晶組成物およびその液晶組成物を用いる
液晶表示素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an acetylene derivative useful as a component of a liquid crystal composition used in a liquid crystal display device, a liquid crystal composition containing the acetylene derivative, and a liquid crystal display element using the liquid crystal composition.
【０００２】0002
【従来の技術】液晶の電気光学効果を利用した液晶表示
装置（ＬＣＤ）は他の表示装置に比べ動作電圧が低くて
消費電力が非常に少ない特徴を有するためＬＳＩ駆動回
路との適合性に優れており、従来より広い分野に応用さ
れてきた。液晶にはスメクチック相、ネマチック相、コ
レステリック相などの諸相が知られており、これらのう
ちネマチック相を用いたＬＣＤが最も普及している。ネ
マチック相を用いたＬＣＤの表示方式には動的散乱型、
ゲスト−ホスト型、捩れたネマチック型（ＴＮ型）、ス
ーパーツイステッドネマチック型（ＳＴＮ型）、スーパ
ーツイステッド複屈折型などがあり、これらのＬＣＤを
動作させる駆動方式にはスタティック駆動、時分割駆動
、二周波駆動、アクティブマトリックス駆動などが用い
られている。[Prior Art] Liquid crystal display devices (LCDs) that utilize the electro-optical effect of liquid crystals have low operating voltage and extremely low power consumption compared to other display devices, and are therefore highly compatible with LSI drive circuits. It has been applied to a wider range of fields than before. Liquid crystals are known to have various phases such as a smectic phase, a nematic phase, and a cholesteric phase, and among these, LCDs using a nematic phase are the most popular. Display methods of LCD using nematic phase include dynamic scattering type,
There are guest-host type, twisted nematic type (TN type), super twisted nematic type (STN type), and super twisted birefringent type.The drive methods for operating these LCDs include static drive, time-division drive, and dual drive. Frequency drive, active matrix drive, etc. are used.
【０００３】前述のＬＣＤのなかでＴＮ型でスタティッ
ク駆動又は時分割駆動のＬＣＤが最も広く応用されてお
り、デジタルウォッチ、電卓、オーディオ機器、電話機
、カメラ等に用いられている。また、最近ではＳＴＮ型
で時分割駆動やＴＮ型でアクティブマトリックス駆動の
ＬＣＤがパソコン、ワープロ、液晶カラーテレビ等の非
常に表示容量の大きなものに応用されつつあり、将来は
ＣＲＴに代る表示装置として注目されている。Among the above-mentioned LCDs, TN type static drive or time division drive LCDs are most widely used, and are used in digital watches, calculators, audio equipment, telephones, cameras, and the like. In addition, in recent years, STN-type time-division drive and TN-type active matrix drive LCDs are being applied to devices with very large display capacities such as personal computers, word processors, and LCD color televisions, and in the future they will replace CRTs as display devices. It is attracting attention as
【０００４】次に、これらのＬＣＤに用いられているネ
マチック液晶にはその応用分野や表示方式等により様々
な特性を要請されるが、このような実用液晶材料の設計
には次の点を考慮する必要がある。■ 化学的、光化
学的、電気的に安定であること。■ 動作温度範囲が
広いこと。■ 粘度が小さく、高速応答ができること
。■ 電気光学特性のしきい値電圧（Ｖｔｈ）が低く
、その温度依存性が小さいこと。■ 電気光学特性の
急峻性が良好なこと。■ 視角範囲が広いこと。[0004] Next, the nematic liquid crystal used in these LCDs is required to have various characteristics depending on its application field, display method, etc., but the following points should be taken into consideration when designing such a practical liquid crystal material. There is a need to. ■ Be chemically, photochemically, and electrically stable. ■ Wide operating temperature range. ■ Low viscosity and high-speed response. ■ The threshold voltage (Vth) of electro-optical characteristics is low and its temperature dependence is small. ■ Good steepness of electro-optical characteristics. ■ Wide viewing angle range.
【０００５】ところで、これら諸特性を単一液晶化合物
で満足させることは不可能であり、実用的には少なくと
も数種類の液晶化合物又はその類似化合物を混合した液
晶組成物を用いている。[0005] However, it is impossible to satisfy these characteristics with a single liquid crystal compound, and in practice, a liquid crystal composition in which at least several types of liquid crystal compounds or similar compounds thereof are mixed is used.
【０００６】また、従来最も広く用いられている時分割
駆動方式のＬＣＤにおいてその表示容量は上記の特性の
うち
（ａ）しきい値電圧の温度依存性
（ｂ）急峻性
（ａ）視角依存性
の３つの特性により決定され、これらの値が小さいほど
表示容量は大きくなる。[0006] In addition, the display capacity of the time-division drive type LCD, which has been most widely used in the past, is determined by the following characteristics among the above characteristics: (a) temperature dependence of threshold voltage (b) steepness (a) viewing angle dependence The display capacity is determined by three characteristics, and the smaller these values, the larger the display capacity.
【０００７】[0007]
【発明が解決しようとする課題】従来より応答速度の速
い液晶材料として知られているフェニルシクロヘキサ系
の液晶化合物は時分割駆動方式のＴＮ又はＳＴＮ型ＬＣ
Ｄに用いた場合に急峻性と視角依存性が悪いために表示
容量が大きくとれない欠点があった。[Problems to be Solved by the Invention] Phenylcyclohexane-based liquid crystal compounds, which have been conventionally known as liquid crystal materials with a fast response speed, are suitable for use in time-division drive type TN or STN type LCs.
When used in D, there was a drawback that a large display capacity could not be obtained due to poor steepness and viewing angle dependence.
【０００８】そこで、本発明の目的は粘度が小さくて複
屈折の小さいアセチレン誘導体を提供することにある。
また、本発明の他の目的は本発明のアセチレン誘導体と
従来の液晶化合物又はその類似化合物を混合することに
より粘度が小さくて複屈折の小さい液晶組成物を提供す
ることにある。さらに、本発明の他の目的は本発明のア
セチレン誘導体を含有する液晶組成物を使用することに
より電気光学特性の急峻性が良好で視角が広く、しかも
応答速度が速い液晶表示素子、特に高速応答で高時分割
駆動が可能な液晶表示素子を提供することにある。[0008] Accordingly, an object of the present invention is to provide an acetylene derivative having low viscosity and low birefringence. Another object of the present invention is to provide a liquid crystal composition with low viscosity and low birefringence by mixing the acetylene derivative of the present invention with a conventional liquid crystal compound or a compound similar thereto. Furthermore, another object of the present invention is to provide a liquid crystal display device which has good steepness of electro-optical characteristics, wide viewing angle, and fast response speed by using the liquid crystal composition containing the acetylene derivative of the present invention, especially a high-speed response. An object of the present invention is to provide a liquid crystal display element that can be driven in multiple time divisions.
【０００９】[0009]
【課題を解決するための手段】本発明は一般式[Means for Solving the Problems] The present invention is based on the general formula
【化４】
（ここで、Ｒは炭素原子数が１〜１０のアルキル基、ｍ
およびｎはｍ≧１、ｎ≧０、ｍ＋ｎ≦８を満足する整数
を表わし、シクロヘキサン環はトランス配置である。）
で表わされるアセチレン誘導体およびそのアセチレン誘
導体を含有する液晶組成物およびその液晶組成物を使用
した液晶表示素子である。embedded image (where R is an alkyl group having 1 to 10 carbon atoms, m
and n represents an integer satisfying m≧1, n≧0, m+n≦8, and the cyclohexane ring has a trans configuration. )
These are an acetylene derivative represented by the following formula, a liquid crystal composition containing the acetylene derivative, and a liquid crystal display element using the liquid crystal composition.
【００１０】本発明のアセチレン誘導体は粘度が小さく
て複屈折が小さい特徴を有する。The acetylene derivative of the present invention is characterized by low viscosity and low birefringence.
【００１１】次に、本発明のアセチレン誘導体の製造方
法について述べる。本発明の化合物は例えば次のスキー
ムにより製造することができる。即ち、４−（トランス
−４′−アルキルシクロヘキシル）フェノールとアルキ
ン−１−オールをテトラヒドロフラン中でアゾジカルボ
ン酸ジエチルとトリフェニルホスフィンを用いてアルコ
キシ化して本発明のアセチレン誘導体（Ｉ）を得る。Next, the method for producing the acetylene derivative of the present invention will be described. The compound of the present invention can be produced, for example, according to the following scheme. That is, 4-(trans-4'-alkylcyclohexyl)phenol and alkyn-1-ol are alkoxylated using diethyl azodicarboxylate and triphenylphosphine in tetrahydrofuran to obtain the acetylene derivative (I) of the present invention.
【化５】
（ここで、Ｒは炭素原子数が１〜１０のアルキル基、ｍ
およびｎははｍ≧１、ｎ≧０、ｍ＋ｎ≦８を満足する整
数を表わし、シクロヘキサン環はトランス配置である。
）本発明のアセチレン誘導体を従来の液晶化合物又はそ
の類似化合物より成るベース液晶と混合して液晶組成物
を作る場合、本発明の化合物の単一成分を混合すること
により粘度が低くて複屈折の小さい液晶組成物を得るこ
とが可能であるが、その複数成分を適切に組み合せて混
合するほうがより効果的である。embedded image (where R is an alkyl group having 1 to 10 carbon atoms, m
and n represents an integer satisfying m≧1, n≧0, m+n≦8, and the cyclohexane ring has a trans configuration. ) When preparing a liquid crystal composition by mixing the acetylene derivative of the present invention with a base liquid crystal consisting of a conventional liquid crystal compound or a compound similar thereto, by mixing a single component of the compound of the present invention, it is possible to obtain a liquid crystal composition with low viscosity and low birefringence. Although it is possible to obtain a small liquid crystal composition, it is more effective to properly combine and mix its multiple components.
【００１２】その場合に用いられるベース液晶の成分と
して次に挙げた化合物が好ましい。The following compounds are preferred as components of the base liquid crystal used in that case.
【化６】
本発明のアセチレン誘導体は上記の化合物のみならず従
来の全ての液晶化合物又はその類似化合物と高い相溶性
を有し、それらの化合物を用いたベース液晶と混合でき
る割合は１〜５０重量％であるが、より好ましくは３〜
３０重量％の範囲である。[Chemical formula 6] The acetylene derivative of the present invention has high compatibility not only with the above compounds but also with all conventional liquid crystal compounds or their similar compounds, and the mixing ratio with the base liquid crystal using these compounds is 1 to 50. % by weight, more preferably 3~
It is in the range of 30% by weight.
【００１３】本発明の液晶組成物を使用した液晶表示素
子は電気光学特性の急峻性が良好で視角が広く、しかも
応答速度が速い特徴を有するため、特に高速応答で高時
分割駆動のＴＮ型又はＳＴＮ型の液晶表示素子として有
用である。[0013] The liquid crystal display element using the liquid crystal composition of the present invention has good steepness of electro-optic characteristics, wide viewing angle, and fast response speed, so it is particularly suitable for use in TN type with high-speed response and high time division drive. Alternatively, it is useful as an STN type liquid crystal display element.
【００１４】次に、本発明の液晶表示素子の一例を第１
図に示す。透明なガラスなどからなる基板１および基板
２がフリットガラスや酸化アルミニウム等のギャップ材
を含むエポキシ系等の接着剤からなるシール材６により
所定の間隔、例えば５〜１５μｍでほぼ平行に封着され
、内部の空間に液晶組成物が封入されている。上記の基
板１および２の対向する内面上には所定のパターンのＳ
ｎＯ２やＩＴＯなどからなる透明電極３が形成され、更
に液晶組成物の接する面は液晶分子を決められた方向に
配向させるための配向制御層４となっている。このよう
な配向制御層は透明電極を有す基板面上に例えばＳｉＯ
を基板面に対して斜めの方向から蒸着させた斜方蒸着膜
又はポリイミド等の有機高分子や無機物を薄く塗布し、
その表面を綿布やナイロンブラシ等で一定方向に擦るラ
ビング処理により作られる。Next, an example of the liquid crystal display element of the present invention will be described in the first example.
As shown in the figure. A substrate 1 and a substrate 2 made of transparent glass or the like are sealed substantially parallel to each other at a predetermined interval, for example, 5 to 15 μm, using a sealing material 6 made of an epoxy adhesive or the like containing a gap material such as frit glass or aluminum oxide. , a liquid crystal composition is sealed in the internal space. A predetermined pattern of S is formed on the opposing inner surfaces of the substrates 1 and 2.
A transparent electrode 3 made of nO2, ITO, or the like is formed, and the surface in contact with the liquid crystal composition serves as an alignment control layer 4 for aligning liquid crystal molecules in a predetermined direction. Such an orientation control layer is formed by depositing, for example, SiO on the substrate surface having transparent electrodes.
An obliquely vapor-deposited film is deposited obliquely to the substrate surface, or a thin layer of organic polymer such as polyimide or an inorganic material is applied.
It is made by rubbing the surface in a certain direction with a cotton cloth, nylon brush, etc.
【００１５】液晶分子の配向方向は基板１と基板２とで
は方向を異ならせ基板１の方向から基板２の方向に向か
って捩れて配向させる。基板１と基板２の配向方向のな
す角、すなわち液晶分子のツイスト角は任意に選択する
ことができるが、ＴＮ型では８０−１３０度、ＳＴＮ型
では１８０−２６０度の範囲が一般的である。The orientation direction of the liquid crystal molecules is different between the substrates 1 and 2, and the liquid crystal molecules are twisted and oriented from the direction of the substrate 1 toward the direction of the substrate 2. The angle between the alignment directions of substrates 1 and 2, that is, the twist angle of the liquid crystal molecules, can be arbitrarily selected, but is generally in the range of 80-130 degrees for TN type and 180-260 degrees for STN type. .
【００１６】基板１および２の外面には各々の基板のラ
ビング方向又はそれと垂直方向に偏光軸を合せて偏光板
５が配置されることにより透過型の液晶表示セルが得ら
れる。なお、反射型の液晶表示セルの場合には第１図に
は示されていないが、基板１又は２の偏光板上に更にア
ルミニウム等の反射板が配置される。A transmissive liquid crystal display cell is obtained by disposing a polarizing plate 5 on the outer surface of the substrates 1 and 2 with the polarization axis aligned in the rubbing direction of each substrate or in a direction perpendicular to the rubbing direction. In the case of a reflective liquid crystal display cell, although not shown in FIG. 1, a reflective plate made of aluminum or the like is further arranged on the polarizing plate of the substrate 1 or 2.
【００１７】ここで、本発明の液晶表示素子の動作原理
を説明する。液晶層に電界がかかっていないときは、外
来光は基板１の外側の偏光板を透過したとき、その偏光
軸に沿った直線偏光となり液晶層に入射されるが、液晶
分子は基板１上から基板２上に向かって捩れているので
液晶層を通過した光の偏光面もツイスト角だけ施光され
、基板２の外側の偏光板を通過して観察者には素子全面
が明るく見える。次に透明電極３に所定の電圧を印加す
るとその領域の液晶分子は電界の方向に沿って配向され
る。即ち、ＴＮ型やＳＴＮ型では当初液晶分子の分子軸
が基板と平行に配向され、しかも誘電異方性が所定の正
の値を有するため、しきい値電圧以上の電圧を印加する
と液晶分子は立ち上り始め、飽和電圧を超えると分子軸
が基板と垂直方向を向く。その結果、その領域では液晶
分子がツイストしていないため入射した光の偏光面は施
光されず基板２の外側の偏光板で遮断されて観察者は電
極部分が暗く見える。したがって、透明電極に電圧を印
加することにより表示を行なうことが可能である。The operating principle of the liquid crystal display element of the present invention will now be explained. When no electric field is applied to the liquid crystal layer, when the external light passes through the polarizing plate on the outside of the substrate 1, it becomes linearly polarized light along the polarization axis and enters the liquid crystal layer. Since it is twisted toward the top of the substrate 2, the polarization plane of the light that has passed through the liquid crystal layer is also applied by the twist angle, and passes through the polarizing plate on the outside of the substrate 2, so that the entire surface of the device appears bright to the viewer. Next, when a predetermined voltage is applied to the transparent electrode 3, the liquid crystal molecules in that region are aligned along the direction of the electric field. That is, in the TN type and STN type, the molecular axes of the liquid crystal molecules are initially aligned parallel to the substrate, and the dielectric anisotropy has a predetermined positive value, so when a voltage higher than the threshold voltage is applied, the liquid crystal molecules When it begins to rise and exceeds the saturation voltage, the molecular axis points perpendicular to the substrate. As a result, since the liquid crystal molecules are not twisted in that region, the polarization plane of the incident light is not applied and is blocked by the polarizing plate outside the substrate 2, so that the electrode portion appears dark to the observer. Therefore, display can be performed by applying a voltage to the transparent electrode.
【００１８】[0018]
【実施例】以下、実施例により本発明の化合物及び液晶
組成物及び液晶表示素子を更に詳しく説明する。
実施例１（化合物の製造）４−（トランス−４′−プロ
ピルシクロヘキシル）−１−（２″−プロピニルオキシ
）ベンゼンの製造方法。EXAMPLES The compounds, liquid crystal compositions, and liquid crystal display elements of the present invention will be explained in more detail with reference to Examples below. Example 1 (Production of compound) Method for producing 4-(trans-4'-propylcyclohexyl)-1-(2''-propynyloxy)benzene.
【００１９】４−（トランス−４′−プロピルシクロヘ
キシル）フェノール６．５ｇとトリフェニルホスフィン
１１．７ｇを無水テトラヒドロフラン１５０ｃｍ３に溶
解し、室温で撹拌しながらプロパギルアルコール２．５
ｇとアゾジカルボン酸 ジエチル７．８ｇを滴下した
。
その後、室温で１晩撹拌した。反応物中のテトラヒドロ
フランを留去し、残渣をクロロホルムを溶媒としてシリ
カゲルカラムで処理した。クロロホルムを留去し、残渣
をメタノールから再結晶して４−（トランス−４′−プ
ロピルシクロヘキシル）−１−（２″−プロピニルオキ
シ）ベンゼン５．２ｇを得た。この化合物の相転移温度
をＤＳＣを用いて測定した結果は次のとおりであった。
なお昇温及び降温速度は５℃／ｍｉｎとした。6.5 g of 4-(trans-4'-propylcyclohexyl)phenol and 11.7 g of triphenylphosphine were dissolved in 150 cm3 of anhydrous tetrahydrofuran, and 2.5 g of propargyl alcohol was added with stirring at room temperature.
g and 7.8 g of diethyl azodicarboxylate were added dropwise. Thereafter, the mixture was stirred at room temperature overnight. Tetrahydrofuran in the reaction mixture was distilled off, and the residue was treated with a silica gel column using chloroform as a solvent. Chloroform was distilled off, and the residue was recrystallized from methanol to obtain 5.2 g of 4-(trans-4'-propylcyclohexyl)-1-(2''-propynyloxy)benzene.The phase transition temperature of this compound was The results measured using DSC were as follows: The temperature rising and cooling rates were 5° C./min.
【化７】
（ここで、Ｃは結晶、Ｉは等方性液体を表わす。）以下
、実施例１と同様な製造方法により次の化合物を得た。embedded image (Here, C represents a crystal and I represents an isotropic liquid.) The following compound was obtained by the same manufacturing method as in Example 1.
【００２０】４−（トランス−４′−プロピルシクロヘ
キシル）−１−（２″−ブチニルオキシ）ベンゼン4-(trans-4'-propylcyclohexyl)-1-(2''-butynyloxy)benzene
【化
８】
４−（トランス−４′−プロピルシクロヘキシル）−１
−（３″−ブチニルオキシ）ベンゼン[Image Omitted] 4-(trans-4'-propylcyclohexyl)-1
-(3″-butynyloxy)benzene
【化９】
４−（トランス−４′−プロピルシクロヘキシル）−１
−（３″−ペンチニルオキシ）ベンゼンembedded image 4-(trans-4'-propylcyclohexyl)-1
-(3″-pentynyloxy)benzene
【化１０】
４−（トランス−４′−ペンチルシクロヘキシル）−１
−（２″−プロピニルオキシ）ベンゼンembedded image 4-(trans-4′-pentylcyclohexyl)-1
-(2″-propynyloxy)benzene
【化１１】
４−（トランス−４′−ヘキシルシクロヘキスル）−１
−（２″−プロピニルオキシ）ベンゼンembedded image 4-(trans-4'-hexylcyclohexyl)-1
-(2″-propynyloxy)benzene
【化１２】
実施例１で製造した化合物の相転移温度を第１表にまと
めて示した。embedded image The phase transition temperatures of the compounds produced in Example 1 are summarized in Table 1.
【表１】
実施例２（液晶組成物）市販のネマチック液晶組成物Ｚ
ＬＩ−１５６５（メルク社製）に本発明の化合物４−（
トランス−４′−プロピルシクロヘキシル）−１−（２
″−プロピニルオキシ）ベンゼンを混合した液晶組成物
をａを作った。[Table 1] Example 2 (Liquid crystal composition) Commercially available nematic liquid crystal composition Z
Compound 4-(of the present invention) was added to LI-1565 (manufactured by Merck & Co.)
trans-4'-propylcyclohexyl)-1-(2
A liquid crystal composition a was prepared by mixing ``-propynyloxy)benzene.
【化１３】
この液晶組成物のネマチック−等方性液体相転移温度（
Ｎ−Ｉ点）、複屈折（△ｎ）および粘度（η）は第２表
のとおりであった。
比較例１（液晶組成物）ＺＬＩ−１５６５およびこれと
４−（トランス−４′−プロピルシクロヘキシル）−１
−プロピルベンゼンを混合した液晶組成物ｂおよびｃを
作った。[Chemical formula 13] Nematic-isotropic liquid phase transition temperature of this liquid crystal composition (
N-I point), birefringence (Δn) and viscosity (η) were as shown in Table 2. Comparative Example 1 (Liquid Crystal Composition) ZLI-1565 and 4-(trans-4'-propylcyclohexyl)-1
- Liquid crystal compositions b and c were prepared by mixing propylbenzene.
【化１４】
これらの液晶組成物のＮ−Ｉ点、△ｎおよびηは第２表
のとおりであった。embedded image The N-I point, Δn and η of these liquid crystal compositions are as shown in Table 2.
【表２】
実施例３（液晶表示素子）第１図に示すようにガラス基
板１および２の対向する面上にＩＴＯの透明電極３を形
成し、この上にポリイミドを塗布し、この表面を綿布で
ラビングして配向制御層４を形成した。ガラス基板１お
よび２をギャップ材を混合したエポキシ系のシール剤６
を介して９μｍの間隔で平行に配置し、この空間に実施
例２の液晶組成物ａを封入した。基板１および２の外側
にラビング方向と偏光軸が一致するように偏光板５をは
りつけた。なお、ツイスト角は９０度のＴＮ型液晶表示
素子とした。[Table 2] Example 3 (Liquid crystal display element) As shown in FIG. 1, transparent electrodes 3 of ITO were formed on opposing surfaces of glass substrates 1 and 2, and polyimide was applied thereon. The alignment control layer 4 was formed by rubbing with a cotton cloth. Epoxy sealant 6 mixed with gap material for glass substrates 1 and 2
The liquid crystal composition a of Example 2 was placed in parallel at intervals of 9 μm through the space. A polarizing plate 5 was attached to the outside of the substrates 1 and 2 so that the rubbing direction and the polarization axis coincided. Note that a TN type liquid crystal display element with a twist angle of 90 degrees was used.
【００２１】このようにして作製した液晶表示素子Ａの
電気光学特性を測定した結果を第３表に示した。なお、
視角依存性α、急峻性βおよび動作マージンＭは次式で
定義し、τＲおよびτＤは立上りおよび立下り速度であ
る。Table 3 shows the results of measuring the electro-optical properties of the liquid crystal display element A thus produced. In addition,
Viewing angle dependence α, steepness β, and operation margin M are defined by the following equations, where τR and τD are rising and falling speeds.
【数１】
（ここで、Ｖ１０およびＶ９０はそれぞれ光透過率１０
％および９０％のときの電圧、Ｔは測定温度、φは視角
を表わし、φは基板面となす角度であり、Ｍは１／３バ
イアス−１／３デューティのときの値である。）比較例
２（液晶表示素子）実施例３と同様にして液晶組成物ｂ
およびｃを封入した液晶表示素子ＢおよびＣを作り、電
気光学特性を測定した結果を第３表に示した。[Equation 1] (Here, V10 and V90 are each light transmittance 10
% and the voltage at 90%, T is the measurement temperature, φ is the viewing angle, φ is the angle with the substrate surface, and M is the value when 1/3 bias - 1/3 duty. ) Comparative Example 2 (Liquid Crystal Display Element) Liquid crystal composition b was prepared in the same manner as in Example 3.
Liquid crystal display elements B and C were prepared in which liquid crystal display elements B and C were sealed, and the electro-optical properties were measured. The results are shown in Table 3.
【表３】[Table 3]
【００２２】[0022]
【発明の効果】以上、述べたように本発明のアセチレン
誘導体及びそれを含有する液晶組成物は粘度が小さく、
複屈折の小さいことがわかった。また、本発明のアセチ
レン誘導体を含有する液晶組成物を使用した液晶表示素
子は電気光学特性の急峻性が良好で視角が広く、応答速
度も比較的速く、さらに動作マージンも広いことが確認
された。[Effects of the Invention] As described above, the acetylene derivative of the present invention and the liquid crystal composition containing the same have a low viscosity;
It was found that the birefringence was small. In addition, it was confirmed that a liquid crystal display element using a liquid crystal composition containing an acetylene derivative of the present invention has good steepness of electro-optical characteristics, a wide viewing angle, a relatively fast response speed, and a wide operating margin. .
【００２３】したがって、本発明のアセチレン誘導体を
含有する液晶組成物を使用した液晶表示素子は高速応答
で高時分割駆動方式のＴＮ型又はＳＴＮ型液晶表示素子
としてたいへん有用である。Therefore, a liquid crystal display device using a liquid crystal composition containing an acetylene derivative of the present invention is very useful as a TN type or STN type liquid crystal display device with high-speed response and high time division driving method.
【図１】本発明の実施例で作製した液晶表示素子の断面
を示す図。FIG. 1 is a diagram showing a cross section of a liquid crystal display element manufactured in an example of the present invention.
１、２ ガラス基板 ３ 透明電極 ４ 配向制御層 ５ 偏光板 ６ シール剤 1, 2 Glass substrate 3 Transparent electrode 4 Orientation control layer 5 Polarizing plate 6 Sealant
Claims (3)
およびｎはｍ≧１、ｎ≧０、ｍ＋ｎ≦８を満足する整数
を表わし、シクロヘキサン環はトランス配置である。）
で表わされることを特徴とするアセチレン誘導体。Claim 1: General formula [Formula 1] (wherein, R is an alkyl group having 1 to 10 carbon atoms, m
and n represents an integer satisfying m≧1, n≧0, m+n≦8, and the cyclohexane ring has a trans configuration. )
An acetylene derivative represented by:
およびｎはｍ≧１、ｎ≧０、ｍ＋ｎ≦８を満足する整数
を表わし、シクロヘキサン環はトランス配置である。）
で表わされるアセチレン誘導体を少なくとも一成分含有
することを特徴とする液晶組成物。Claim 2: General formula [Formula 2] (wherein, R is an alkyl group having 1 to 10 carbon atoms, m
and n represents an integer satisfying m≧1, n≧0, m+n≦8, and the cyclohexane ring has a trans configuration. )
1. A liquid crystal composition containing at least one component of an acetylene derivative represented by:
およびｎはｍ≧１、ｎ≧０、ｍ＋ｎ≦８を満足する整数
を表わし、シクロヘキサン環はトランス配置である。）
で表わされるアセチレン誘導体を少なくとも一成分含有
する液晶組成物を用いることを特徴とする液晶表示素子
。Claim 3: General formula [Formula 3] (wherein, R is an alkyl group having 1 to 10 carbon atoms, m
and n represents an integer satisfying m≧1, n≧0, m+n≦8, and the cyclohexane ring has a trans configuration. )
A liquid crystal display element characterized in that it uses a liquid crystal composition containing at least one component of an acetylene derivative represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP431491A JPH04235939A (en) | 1991-01-18 | 1991-01-18 | Acetylene derivative, liquid crystal composition containing the same and liquid crystal display element produced by using the composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP431491A JPH04235939A (en) | 1991-01-18 | 1991-01-18 | Acetylene derivative, liquid crystal composition containing the same and liquid crystal display element produced by using the composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04235939A true JPH04235939A (en) | 1992-08-25 |
Family
ID=11581019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP431491A Pending JPH04235939A (en) | 1991-01-18 | 1991-01-18 | Acetylene derivative, liquid crystal composition containing the same and liquid crystal display element produced by using the composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04235939A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003064367A (en) * | 2001-08-29 | 2003-03-05 | Dainippon Ink & Chem Inc | Liquid crystal display element |
-
1991
- 1991-01-18 JP JP431491A patent/JPH04235939A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003064367A (en) * | 2001-08-29 | 2003-03-05 | Dainippon Ink & Chem Inc | Liquid crystal display element |
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