JPS5832845A - Trans-4-substituted-cyclohexanecarboxylic acid 3,4-dichlorophenyl ester - Google Patents
Trans-4-substituted-cyclohexanecarboxylic acid 3,4-dichlorophenyl esterInfo
- Publication number
- JPS5832845A JPS5832845A JP13051181A JP13051181A JPS5832845A JP S5832845 A JPS5832845 A JP S5832845A JP 13051181 A JP13051181 A JP 13051181A JP 13051181 A JP13051181 A JP 13051181A JP S5832845 A JPS5832845 A JP S5832845A
- Authority
- JP
- Japan
- Prior art keywords
- trans
- cyclohexanecarboxylic acid
- compound
- liquid crystal
- substituted
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は正の誘電異方性を有する液晶物質及び非液晶物
質に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to liquid crystal materials and non-liquid crystal materials having positive dielectric anisotropy.
液晶表示素子は液晶物質が持つ光学異方性及び誘電異方
性を利用したものであるが、その表示様式によってＴＮ
型（ねじれネマチック型）、ＤＳ型（動的散乱型）、ゲ
スト・ホスト型、ＤＡＰ型など各種の方式に分けられ、
夫々の使用に適する液晶物質の性質は異る１、しかし、
いすり、の液晶物質も、水分、空気、熱、光等圧安定で
なけれはならないことは共通しており、又室温を中心と
して出来るだけ広い温度範囲で液晶相でちゃ、更に表示
素子の様式に適した誘電異方性値（△ｅ）を刹していな
１丁ればならない。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, but depending on the display format, TN
It is divided into various types such as type (twisted nematic type), DS type (dynamic scattering type), guest-host type, and DAP type.
The properties of liquid crystal materials suitable for each use vary1, but
It is common that the liquid crystal materials used in Isuri must be isobarically stable to moisture, air, heat, and light, and must remain in the liquid crystal phase over a wide temperature range centered around room temperature. The dielectric anisotropy value (Δe) suitable for the dielectric anisotropy value (Δe) must be one.
しかし現在のところ、単一化合物ではこの様な条件をみ
たす様な物質はなく、数種の液晶化合物や非液晶化合物
を混合して得られる液晶組成物を使用しているのが現状
である。However, at present, there is no single compound that satisfies these conditions, and the current situation is to use liquid crystal compositions obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds.
本発明の目的はこの様な液晶組成物の一成分として有用
な、特にΔεの値ン調節し、更に粘度を低くするのに適
した新規な液晶化合物を提供することＫある。An object of the present invention is to provide a novel liquid crystal compound useful as a component of such a liquid crystal composition, particularly suitable for adjusting the value of Δε and further lowering the viscosity.
即ち、本発明は一般式
（上式中ｎは１又ｔ１２であり、Ｒは炭素数１〜１０の
アルキル基を示す）
で表わされるトランス−４−置換シクロヘキサンカルボ
ン酸３，４−ジクロロフェニルエステ・：
ｋ及びこれを少なくとも一檻含有することを特徴とする
液晶組成物である。That is, the present invention provides trans-4-substituted cyclohexanecarboxylic acid 3,4-dichlorophenyl ester represented by the general formula (in the above formula, n is 1 or t12, and R represents an alkyl group having 1 to 10 carbon atoms). : k and at least one cage thereof.
本発明の化合物は△εが＋４程度で６１、又粘度が低く
、組成物に加えることＫよりもとの組成物の電気的特性
、すなわちしきい値電圧及び飽和電圧を下げることがで
きる。また（１）式中、ｎ ＝ １の化合物は非晶化合
物であるが、ｎ ＝ ２の化合物は広い範四で、高温ま
でネマチック液晶相を示すので、組成物のＮ−Ｉを上昇
させるのに有効である。The compound of the present invention has a Δε of about +4, 61, and has a low viscosity, so adding K to the composition can lower the electrical properties of the original composition, that is, the threshold voltage and saturation voltage. In addition, in formula (1), the compound with n = 1 is an amorphous compound, but the compound with n = 2 exhibits a nematic liquid crystal phase up to high temperatures in a wide range of ranges, so it is important to increase the N-I of the composition. It is effective for
つぎに本発明の化合物の製造法を示す。まず目的−に対
応するトランス−４−置換シクロヘキサンカルボン酸を
塩化チオニルを反応させて、トランス−４−を換シクロ
ヘキサンカルボン酸クロリドとし、ついでピリジン存在
下３，４−ジクロロフェノールと反応して目的の化合物
を得る。これを化学式で示すと
（上式中Ｋｌ、 Ｒは前記と同じ）
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。Next, a method for producing the compound of the present invention will be described. First, trans-4-substituted cyclohexanecarboxylic acid corresponding to the objective is reacted with thionyl chloride to obtain trans-4-substituted cyclohexanecarboxylic acid chloride, and then reacted with 3,4-dichlorophenol in the presence of pyridine to obtain the objective. Obtain the compound. This is expressed as a chemical formula (in the above formula, Kl and R are the same as above).The manufacturing method and usage examples of the compound of the present invention will be explained in more detail with reference to Examples below.
実施例１〔トランス−４−（トランス−４′−エチルシ
クロヘキシル）シクロヘキサン
カルホン酸３．４−ジクロロフェニル
エステルの製造〕
トランス−４−（）ランス−４′−エチルシクロヘキシ
ル）シクロヘキサンカルボン酸２．４ｆ（α０１モル）
と塩化チオニル１０−をフラスコに入れ、５０℃に加温
する。６時間で均一となる。過剰の塩化チオニルを減圧
にて留去する。Example 1 [Production of trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid 3.4-dichlorophenyl ester] Trans-4-()trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid 2.4f (α01 mol)
and thionyl chloride 10- are placed in a flask and heated to 50°C. It becomes uniform in 6 hours. Excess thionyl chloride is distilled off under reduced pressure.
残った油状物がトランス−４−（トランス−４′−エチ
ルシクロヘキシル）シクロヘキサンカルボン酸クロリド
である。一方３．４−ジクロロフェノール１．７ Ｆ
（０，０１モル）をピリジン１〇−にとかしておいたも
のに先に得られた酸クロリドを加え、乾燥トルエン１Ｕ
〇−加え、よくふシまぜ、−晩装置する。反応液を水に
あけ、６Ｎ塩酸、２Ｎ水酸化ナトリウム、ついで中性５
−
になるまで水洗する。トルエン層を無水硫酸ナトリウム
で乾燥後ｆ過してから、トルエンを減圧にて留去し、残
った油状物をエタノールで再結晶すると、目的のトラン
ス−４−（トランス−４１−エチルシクロヘキシル）シ
クロヘキサンカルボン酸３．４− ジクロロフェニルエ
ステルが得られた。収量２．７ Ｆ 、収率７０チ又、
そのＣ−Ｎ点は８５．５〜８７．１℃、Ｎ−Ｉ点は１０
０．３℃であった。The remaining oil is trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid chloride. On the other hand, 3.4-dichlorophenol 1.7 F
(0.01 mol) was dissolved in 10-pyridine, the acid chloride obtained earlier was added, and 1U of dry toluene was added.
〇-Add, stir well, and set aside overnight. Pour the reaction solution into water, add 6N hydrochloric acid, 2N sodium hydroxide, and then add neutral 5
- Rinse with water until . The toluene layer was dried over anhydrous sodium sulfate and filtered, and the toluene was distilled off under reduced pressure. The remaining oil was recrystallized from ethanol to obtain the desired trans-4-(trans-41-ethylcyclohexyl)cyclohexane. Carboxylic acid 3,4-dichlorophenyl ester was obtained. Yield 2.7F, yield 70T,
Its C-N point is 85.5-87.1℃, and its N-I point is 10
The temperature was 0.3°C.
実施例２〜１２
実施例１に於けるトランス−４−（）＞シス−４′−エ
チルシクロヘキシル）シクロヘキサンカルボン酸の代シ
に他のアルキル基を有するトランス−４−（）ランス−
４′−フルキルシクロヘキシル）シクロヘキサンカルボ
ン酸又はトランス−４−アルキルシクロへキサンカルボ
ン酸を使用して同様の操作で第１表の実施例２〜１２の
欄に示す（１）式の化合物を製造した。これらの収率、
物性値等を実施例１の結果と共に第１表に示す。Examples 2 to 12 Trans-4-() trans-4-() having another alkyl group in place of trans-4-()>cis-4'-ethylcyclohexyl)cyclohexanecarboxylic acid in Example 1
4'-Furkylcyclohexyl)cyclohexanecarboxylic acid or trans-4-alkylcyclohexanecarboxylic acid to produce a compound of formula (1) shown in the Examples 2 to 12 column of Table 1 in the same manner. did. These yields,
The physical property values and the like are shown in Table 1 together with the results of Example 1.
一式一
実施例１６（使用例）
４−ベンチルー４′−シアノビフェニ−Ａ−５１１４−
ヘプチル−４７−ジアツビフエニ＃ ５ｉ４−オクチ
ルオキシ−４′−シアノピフェニル１７％
なる組成の液晶混合物のＮ−Ｉ点は４４．３℃、粘度は
２０′Ｃで４０ＣＩ）、誘電異方性は＋１２．４である
。この液晶混合物をケイ素でコーティングし、ラビング
処理した酸化スズ透明電極を備えた２枚の基板を組み立
てた厚さ１０μｍのセルに封入して液晶セルとし、２５
℃でその特性を測定したところ、しきい電圧１．６５Ｖ
％飽和電圧は２．３１Ｖでめった。Complete set 1 Example 16 (Usage example) 4-Benchrue 4'-Cyanobipheny-A-5114-
Heptyl-47-diatubiphenyl #5i 4-octyloxy-4'-cyanopiphenyl 17% The N-I point of the liquid crystal mixture is 44.3°C, the viscosity is 40CI at 20'C), and the dielectric anisotropy is +12 .4. This liquid crystal mixture was coated with silicon and sealed in a 10 μm thick cell assembled with two substrates equipped with rubbed tin oxide transparent electrodes to form a liquid crystal cell.
When its characteristics were measured at °C, the threshold voltage was 1.65V.
The % saturation voltage was 2.31V.
この液晶混合物９０部に本発明実施例２のトランス−４
−（）ランス−４７−プロピルシクロヘキシル）シクロ
ヘキサンカルボン２３．４−ジクロロフェニルエステル
１０部を力１えた液晶混合物のＮ−Ｉ点は５３．４℃に
上り、誘電異方性値は＋１１．５．粘度は２０℃で、３
８ｃｐに下がった。又しきい電圧はｔ６ＤＶ、飽和電圧
Ｕ２．２５Ｖに下った。Trans-4 of Example 2 of the present invention was added to 90 parts of this liquid crystal mixture.
-()lance-47-propylcyclohexyl)cyclohexanecarvone 23. The N-I point of a liquid crystal mixture containing 10 parts of 4-dichlorophenyl ester reaches 53.4°C, and the dielectric anisotropy value is +11.5. The viscosity is 3 at 20°C.
It dropped to 8 cp. Also, the threshold voltage fell to t6DV, the saturation voltage U2.25V.
以上 ９−that's all 9-
Claims (2)
ルキル基を示す） で表わされるトランス−４−置換シクロヘキサンカルボ
ン酸３．４−ジクロロフェニルエステル。(1) Trans-4-substituted cyclohexanecarboxylic acid 3,4-dichlorophenyl ester represented by the general formula (in the above formula, n is 1 or 2, and R represents an alkyl group having 1 to 10 carbon atoms).
ルキル基を示す） で表わされるトランス−４−置換シクロヘキサンカルボ
ン酸３．４−ジクロロフェニルエステルを少なくとも一
棟含有することを特徴とする液晶組成物。(2) At least one trans-4-substituted cyclohexanecarboxylic acid 3,4-dichlorophenyl ester represented by the general formula (in the above formula, n is 1 or 2, and R represents an alkyl group having 1 to 10 carbon atoms) A liquid crystal composition characterized by containing ridges.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13051181A JPS5832845A (en) | 1981-08-20 | 1981-08-20 | Trans-4-substituted-cyclohexanecarboxylic acid 3,4-dichlorophenyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13051181A JPS5832845A (en) | 1981-08-20 | 1981-08-20 | Trans-4-substituted-cyclohexanecarboxylic acid 3,4-dichlorophenyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5832845A true JPS5832845A (en) | 1983-02-25 |
| JPH0150691B2 JPH0150691B2 (en) | 1989-10-31 |
Family
ID=15036034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13051181A Granted JPS5832845A (en) | 1981-08-20 | 1981-08-20 | Trans-4-substituted-cyclohexanecarboxylic acid 3,4-dichlorophenyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5832845A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02243665A (en) * | 1979-05-28 | 1990-09-27 | Merck Patent Gmbh | Method for controlling dielectric anisotropy of liquid crystal mixture |
| JPH0733066A (en) * | 1993-06-22 | 1995-02-03 | Casio Comput Co Ltd | Motor-driven vehicle |
| JP2011207783A (en) * | 2010-03-29 | 2011-10-20 | Dic Corp | Transparent insulating composition |
| JP2014177446A (en) * | 2013-10-21 | 2014-09-25 | Dic Corp | Transparent insulation composition |
-
1981
- 1981-08-20 JP JP13051181A patent/JPS5832845A/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02243665A (en) * | 1979-05-28 | 1990-09-27 | Merck Patent Gmbh | Method for controlling dielectric anisotropy of liquid crystal mixture |
| JPH0433834B2 (en) * | 1979-05-28 | 1992-06-04 | Merck Patent Gmbh | |
| JPH0733066A (en) * | 1993-06-22 | 1995-02-03 | Casio Comput Co Ltd | Motor-driven vehicle |
| JP2011207783A (en) * | 2010-03-29 | 2011-10-20 | Dic Corp | Transparent insulating composition |
| JP2014177446A (en) * | 2013-10-21 | 2014-09-25 | Dic Corp | Transparent insulation composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0150691B2 (en) | 1989-10-31 |
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