JP2887693B2 - Small ring compounds - Google Patents
Small ring compoundsInfo
- Publication number
- JP2887693B2 JP2887693B2 JP21180690A JP21180690A JP2887693B2 JP 2887693 B2 JP2887693 B2 JP 2887693B2 JP 21180690 A JP21180690 A JP 21180690A JP 21180690 A JP21180690 A JP 21180690A JP 2887693 B2 JP2887693 B2 JP 2887693B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- small ring
- crystal composition
- compound
- present
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、新規な小員環化合物及び該化合物を有効成
分として含む液晶組成物に関する。Description: TECHNICAL FIELD The present invention relates to a novel small ring compound and a liquid crystal composition containing the compound as an active ingredient.
液晶を利用した表示素子は時計、電卓等に広く使用さ
れている。これらの液晶表示素子は液晶物質の光学異方
性及び誘電異方性を利用したものである。液晶にはネマ
チツク液晶相、スメクチツク液晶相、コレステリツク液
晶相を示すものがあり、そのうちネマチツク液晶相を利
用したものが最も広く実用化され、スメクチツク液晶相
については応用開発がさかんに行なわれている。Display elements using liquid crystals are widely used in watches, calculators, and the like. These liquid crystal display devices utilize the optical anisotropy and dielectric anisotropy of a liquid crystal material. Liquid crystals include a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase. Among them, those using the nematic liquid crystal phase have been most widely put to practical use, and the smectic liquid crystal phase is being actively developed for application.
液晶表示素子には液晶表示に応用されている電気光学
効果に対応して、TN（ねじれネマチツク）型、DS（動的
散乱）型、ゲスト・ホスト型、DAP型など各種方式のも
のがあり、それぞれに使用される液晶物質は水分、光、
熱、空気等に対して安定である上、自然界のなるべく広
い温度範囲で液晶相を示すものが望ましい。There are various types of liquid crystal display devices, such as TN (twisted nematic) type, DS (dynamic scattering) type, guest-host type, and DAP type, corresponding to the electro-optic effect applied to liquid crystal display. The liquid crystal material used for each is moisture, light,
Desirable are those which are stable against heat, air and the like, and which exhibit a liquid crystal phase in a temperature range as wide as possible in nature.
既に多くの液晶物質（一般に化合物）が知られている
が、現在のところ単一の液晶物質でそのような条件をみ
たすものはなく、数種の液晶物質またはさらに非液晶物
質を混合して実用に供されている。このような液晶物質
などの混合物すなわち液晶組成物はさらに省電力で、視
覚が広く、応答速度が速く、劣化しにくいものが望ま
れ、このためにしきい値電圧（Vth）が低く、光学異方
性値（Δｎ）が小さく、粘度が低くかつ化学的に安定な
ことが望まれている。Many liquid crystal materials (generally compounds) are already known, but at present there is no single liquid crystal material that satisfies such conditions, and several liquid crystal materials or even non-liquid crystal materials are mixed for practical use. Has been offered to. It is desired that such a mixture of liquid crystal substances, that is, a liquid crystal composition, further saves power, has a wide vision, has a high response speed, and is hardly deteriorated. Therefore, the threshold voltage (Vth) is low, and It is desired that the property value (Δn) is small, the viscosity is low, and the composition is chemically stable.
本発明の目的は、液晶組成物に係る上述の要請に鑑
み、これを満たす新規な液晶化合物及び該化合物を含む
液晶組成物を提供することにある。An object of the present invention is to provide a novel liquid crystal compound that satisfies the above-mentioned requirements for a liquid crystal composition and a liquid crystal composition containing the compound.
本発明は、一般式 （上式中、Ｒは直鎖又は枝分れした炭素数１〜15のアル
キル基、Ａは ｎは１〜15、Ｂは をそれぞれ示す。）で表わされる小員環化合物及び該化
合物を少なくとも一種類含有することを特徴とする液晶
組成物である。The present invention has the general formula (In the above formula, R is a linear or branched alkyl group having 1 to 15 carbon atoms, and A is n is 1 to 15, B is Are respectively shown. ), And a liquid crystal composition comprising at least one kind of the compound.
本発明の小員環化合物は、小さい正の誘電異方性値を
示す上低粘性で小さい屈折率異方性値を示す液晶性化合
物であり、かつ熱、空気、水分、光等に安定であるた
め、低温から高温まで広い温度範囲で動作する液晶組成
物を得るのに極めて有用な化合物である。The small ring compound of the present invention is a liquid crystalline compound exhibiting a small positive dielectric anisotropy value, a low viscosity and a small refractive index anisotropy value, and is stable to heat, air, moisture, light and the like. Therefore, it is a very useful compound for obtaining a liquid crystal composition which operates in a wide temperature range from a low temperature to a high temperature.
上記の本発明小員環化合物は通常、一般式（Ｉ）で示
したフエノール類を、N,N−ジメチルホルムアミド（以
下、DMFと略する。）を溶媒とし無水炭酸カリウムの存
在下一般式（II）で示すω−臭化アルキルシクロアルカ
ンと反応を行うことにより好適に製造される。The above small ring compound of the present invention is usually prepared by converting the phenol represented by the general formula (I) into N, N-dimethylformamide (hereinafter abbreviated as DMF) as a solvent in the presence of anhydrous potassium carbonate. It is preferably produced by reacting with an ω-alkylcycloalkane shown in II).
（上記反応式中、Ｒ、Ａ、ｎ、Ｂは前記と同一であ
る。） 〔発明の作用、効果〕 本発明の小員環化合物は、他の多くの液晶化合物、す
なわちエステル系、シツフ塩基系、ビフエニル系、フエ
ニルシクロヘキサン系、複素環系等の液晶化合物との相
溶性がよく、これら液晶化合物を含む液晶組成物に加え
た場合、Δｎを小さく保持しかつ低粘性化が可能とな
り、液晶表示素子用に好適な液晶組成物を与えることが
できる。 (In the above reaction formula, R, A, n, and B are the same as described above.) [Action and Effect of the Invention] The small-membered ring compound of the present invention includes many other liquid crystal compounds, that is, ester compounds and Schiff bases. System, biphenyl type, phenylcyclohexane type, good compatibility with liquid crystal compounds such as heterocyclic type, when added to a liquid crystal composition containing these liquid crystal compounds, it is possible to keep Δn small and reduce the viscosity, A liquid crystal composition suitable for a liquid crystal display device can be provided.
以下、実施例により本発明の化合物の製造法及び使用
例について更に詳細に説明するが、本発明はこれらの実
施例によつて何等限定されるものではない。Hereinafter, the production method and use examples of the compound of the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１ １−シクロプロピルメチルオキシ−４−（トランス−４
−プロピルシクロヘキシル）ベンゼン（前記一般式で示
す本発明化合物において、Ｒ＝C3H7−、 の場合。）の製造 ４−（トランス−４−プロピルシクロヘキシル）フエ
ノール2.1g（0.01モル）に200mlのDMFを加え、これに無
水炭酸カリウム50gを加えた。撹拌しながら臭化メチル
シクロプロパン3.6g（0.03モル）を加え、80℃で12時間
反応を行なつた。Example 1 1-cyclopropylmethyloxy-4- (trans-4
-Propylcyclohexyl) benzene (in the compound of the present invention represented by the above general formula, R = C 3 H 7 —, in the case of. Preparation of)) To 2.1 g (0.01 mol) of 4- (trans-4-propylcyclohexyl) phenol was added 200 ml of DMF, and 50 g of anhydrous potassium carbonate was added thereto. 3.6 g (0.03 mol) of methylcyclopropane bromide was added with stirring, and the reaction was carried out at 80 ° C. for 12 hours.
反応終了後、反応液に水を加え、析出した油状物をト
ルエンで抽出した。トルエン層を2N水酸化ナトリウムで
洗い、ついで中性になるまで水でトルエン層を洗つた。After completion of the reaction, water was added to the reaction solution, and the precipitated oil was extracted with toluene. The toluene layer was washed with 2N sodium hydroxide and then with water until neutral.
無水硫酸ナトリウムでトルエン層を乾燥後、トルエン
を減圧にして留去した。残つた結晶をアセトンで再結晶
を行なつて融点50.2〜50.6℃の１−シクロプロピルメチ
ルオキシ−４−（トランス−４−プロピルシクロヘキシ
ル）ベンゼン2.1g（収率77％）を得た。After drying the toluene layer with anhydrous sodium sulfate, the toluene was distilled off under reduced pressure. The remaining crystals were recrystallized from acetone to obtain 2.1 g (77% yield) of 1-cyclopropylmethyloxy-4- (trans-4-propylcyclohexyl) benzene having a melting point of 50.2 to 50.6 ° C.
実施例２〜４ ４−（トランス−４−プロピルシクロヘキシル）フエ
ノールに代えＲ、Ａを第１表参照のものとしたフエノー
ル類及び臭化メチルシクロプロパンに代えｎ、Ｂを第１
表参照のものとしたω−臭化アルキルシクロアルカンを
用いる以外は実施例１と同様にして種々の小員環化合物
を製造した。これらの結果を実施例１の結果と共に第１
表に示した。Examples 2 to 4 Instead of 4- (trans-4-propylcyclohexyl) phenol, R and A were the same as those shown in Table 1, and n and B were replaced by phenols and methylcyclopropane bromide.
Various small-membered ring compounds were produced in the same manner as in Example 1 except that the ω-alkyl bromide cycloalkane shown in the table was used. These results were combined with the results of Example 1 in the first
It is shown in the table.
実施例５（使用例） トランス−４−プロピル−（４′−シアノフエニル）
シクロヘキサン 24重量％ トランス−４−ペンチル−（４′−シアノフエニル）
シクロヘキサン 36重量％ トランス−４−ヘプチル−（４′−シアノフエニル）
シクロヘキサン 25重量％ トランス−４−ペンチル−（４′−シアノビフエニ
ル）シクロヘキサン 15重量％ からなる液晶組成物（Ａ）のＮ−Ｉ点は72.6℃、Δεは
＋11.6、20℃における粘度は26.4cp、Δｎは0.138であ
る。別途液晶セルとして、酸化ケイ素をコーテイングし
ラビング処理した酸化スズ透明電極を有する基板を対向
させて組立てた電極間距離10μｍのものを用意し、これ
に上記の液晶組成物（Ａ）を封入して20℃でその特性を
測定したところ、しきい値電圧は1.78Vであつた。 Example 5 (Example of use) trans-4-propyl- (4'-cyanophenyl)
Cyclohexane 24% by weight trans-4-pentyl- (4'-cyanophenyl)
Cyclohexane 36% by weight trans-4-heptyl- (4'-cyanophenyl)
The liquid crystal composition (A) comprising 25% by weight of cyclohexane and 15% by weight of trans-4-pentyl- (4'-cyanobiphenyl) cyclohexane has an NI point of 72.6 ° C., Δε of +11.6, and a viscosity at 20 ° C. of 26.4 cp. , Δn is 0.138. Separately, a liquid crystal cell having a distance of 10 μm between electrodes assembled with a substrate having a tin oxide transparent electrode coated with silicon oxide and rubbed was prepared, and the above liquid crystal composition (A) was sealed therein. When its characteristics were measured at 20 ° C., the threshold voltage was 1.78 V.
一方、この液晶組成物（Ａ）85重量％に本発明の実施
例１で製造した１−シクロプロピルメチルオキシ−４−
（トランス−４−プロピルシクロヘキシル）ベンゼン15
重量％を溶解した組成物についてＮ−Ｉ点、Δε、Δｎ
及び粘度を求めたところ、それぞれ58.9℃、＋10.1、0.
123及び25.5cpであつた。又しきい値電圧は1.61Vと低下
した。On the other hand, 1-cyclopropylmethyloxy-4- produced in Example 1 of the present invention was added to 85% by weight of the liquid crystal composition (A).
(Trans-4-propylcyclohexyl) benzene 15
% NI, Δε, Δn
When the viscosity was determined, the temperature was 58.9 ° C., +10.1, and 0.1, respectively.
123 and 25.5 cp. The threshold voltage dropped to 1.61V.
このように、本発明液晶組成物とすることによりΔ
ｎ、粘度及びしきい値電圧がいずれも改善された。Thus, by using the liquid crystal composition of the present invention, Δ
n, viscosity and threshold voltage were all improved.
Claims (2)
キル基、Ａは ｎは１〜15、Ｂは をそれぞれ示す。）で表わされる小員環化合物。(1) General formula (In the above formula, R is a linear or branched alkyl group having 1 to 15 carbon atoms, and A is n is 1 to 15, B is Are respectively shown. A small ring compound represented by the formula:
キル基、Ａは ｎは１〜15、Ｂは をそれぞれ示す。）で表わされる小員環化合物を少なく
とも一種類含有することを特徴とする液晶組成物。2. The general formula (In the above formula, R is a linear or branched alkyl group having 1 to 15 carbon atoms, and A is n is 1 to 15, B is Are respectively shown. A liquid crystal composition comprising at least one kind of the small ring compound represented by the formula (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21180690A JP2887693B2 (en) | 1990-08-10 | 1990-08-10 | Small ring compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21180690A JP2887693B2 (en) | 1990-08-10 | 1990-08-10 | Small ring compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0495044A JPH0495044A (en) | 1992-03-27 |
| JP2887693B2 true JP2887693B2 (en) | 1999-04-26 |
Family
ID=16611911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21180690A Expired - Lifetime JP2887693B2 (en) | 1990-08-10 | 1990-08-10 | Small ring compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2887693B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107286948A (en) * | 2015-02-15 | 2017-10-24 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal composition and its application in liquid crystal display |
-
1990
- 1990-08-10 JP JP21180690A patent/JP2887693B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0495044A (en) | 1992-03-27 |
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