JP2822079B2 - Cyclopropane derivative - Google Patents
Cyclopropane derivativeInfo
- Publication number
- JP2822079B2 JP2822079B2 JP4400690A JP4400690A JP2822079B2 JP 2822079 B2 JP2822079 B2 JP 2822079B2 JP 4400690 A JP4400690 A JP 4400690A JP 4400690 A JP4400690 A JP 4400690A JP 2822079 B2 JP2822079 B2 JP 2822079B2
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- Japan
- Prior art keywords
- liquid crystal
- compound
- trans
- type
- 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、新規なシクロプロパン誘導体液晶化合物お
よび該化合物を有効成分とする液晶組成物に関する。The present invention relates to a novel cyclopropane derivative liquid crystal compound and a liquid crystal composition containing the compound as an active ingredient.
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、その表示様式によつてTN
型（ねじれネマチツク型）、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。しかしいずれの
液晶物質も水分、空気、熱、光等に安定であることが必
要であることは共通しており、又、室温を中心としてで
きるだけ広い温度範囲で液晶相を示し、更に表示素子の
種類によつて異なる最適な誘導異方性値（△ε）を有す
るようにしなければならない。しかし現在のところ単一
化合物ではこのような条件を満たす物質はなく、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。最近は特に低温（−
40℃程度）から高温（100℃以上）にわたつて動作する
表示素子が要求されるようになつてきているので、より
広い温度範囲ですぐれた動作特性を持つた液晶組成物が
要望されている。Liquid crystal display devices use the optical anisotropy and dielectric anisotropy of liquid crystal materials.
There are various types of liquid crystal materials, such as a liquid crystal type (twisted nematic type), a DS type (dynamic scattering type), a guest-host type, and a DAP type. However, it is common that all liquid crystal substances need to be stable to moisture, air, heat, light, etc., and exhibit a liquid crystal phase in a temperature range as wide as possible around room temperature. It is necessary to have an optimal induced anisotropy value (異 な る ε) that differs depending on the type. However, at present, no single compound satisfies such conditions, and at present, a liquid crystal composition obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds is used. Recently, especially low temperature (-
Since a display element that operates from a temperature of about 40 ° C. to a high temperature (100 ° C. or more) has been required, a liquid crystal composition having excellent operation characteristics in a wider temperature range has been demanded. .
本発明の目的は低粘性で高温まで動作する液晶表示素
子に必要な新規な液晶化合物及び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 and a liquid crystal composition necessary for a liquid crystal display device which operates at a high temperature with a low viscosity.
本発明は一般式 （上式に於いてＲは炭素数１〜10の直鎖又は分岐のアル
キル基を示し、ｎは１〜10の整数を示す）で表わされる
シクロプロパン誘導体液晶化合物及びこれを少なくとも
一種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 Wherein, in the above formula, R represents a linear or branched alkyl group having 1 to 10 carbon atoms, and n represents an integer of 1 to 10; A liquid crystal composition characterized by the following.
本発明の化合物は小さい正の誘電異方性値を示し、液
晶温度範囲が広く、特に高い液晶−透明点（Ｎ−Ｉ点、
又はSm−Ｉ点）を持つていて、なおかつ低粘性の化合物
であり、更に熱、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 compound of the present invention exhibits a small positive dielectric anisotropy value, has a wide liquid crystal temperature range, and particularly has a high liquid crystal-clearing point (NI point,
Or Sm-I point) and is a low-viscosity compound, and is stable to heat, air, moisture, light, etc.
It is a compound that is extremely useful for obtaining a liquid crystal composition that operates in a wide temperature range from a low temperature to a high temperature.
つぎに本発明の化合物の製造法を示すと、４−〔トラ
ンス−４−（トランス−４−アルキルシクロヘキシル）
シクロヘキシル〕フエノールをN,N−ジメチルホルムア
ミド（以下、DMFと略す）を溶媒とし、無水炭酸カリウ
ムとω−臭化アルキルシクロプロパンと反応を行い、目
的のシクロプロパン誘導体液晶化合物を製造した。Next, the production method of the compound of the present invention is described as follows: 4- [trans-4- (trans-4-alkylcyclohexyl)
Cyclohexyl] phenol was used as a solvent with N, N-dimethylformamide (hereinafter abbreviated as DMF) as a solvent to react with anhydrous potassium carbonate and ω-alkylcyclopropane to produce a desired cyclopropane derivative liquid crystal compound.
〔本発明の効果〕 本発明の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容性がよ
く、本発明の化合物を液晶組成物に加えることにより、
△ｎは小さく保持でき、Ｎ−Ｉ点を上昇させることがで
きるために、高温度でも動作可能な液晶表示素子に用い
る液晶組成物に好適な化合物である。 [Effect of the present invention] The compound of the present invention has good compatibility with many other liquid crystal compounds, that is, liquid crystal compounds such as ester type, Schiff base type, biphenyl type, phenylcyclohexane type and heterocyclic type. By adding the compound of the invention to the liquid crystal composition,
Since Δn can be kept small and the NI point can be raised, it is a compound suitable for a liquid crystal composition used for a liquid crystal display element that can operate even at a high temperature.
以下、実施例により本発明の化合物の整合法及び使用
例について更に詳細に説明するが、本発明はこの実施例
によつて何等限定されうものではない。Hereinafter, the matching 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−トランス−４−シクロヘキシ
ル〕ベンゼン（（Ｉ）式でＲ＝C3H7−、ｎ＝１のもの）
の製造 ４−〔トランス−４−（トランス−４−プロピルシク
ロヘキシル）シクロヘキシル〕フエノール3.0g（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時間反応を行つた。Example 1 1-cyclopropylmethyloxy-4 [trans-4-
Propylcyclohexyl-trans-4-cyclohexyl] benzene (in the formula (I), R = C 3 H 7 —, n = 1)
Preparation of 4- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] phenol to 3.0 g (0.01 mol) of DMF was added to 200 ml of DMF, and 50 g of anhydrous potassium carbonate was added thereto.
Was added. 3.6 g of methylcyclopropane bromide with stirring
(0.03 mol) and reacted 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
を行つた。結晶−スメクチツク点（Ｃ−Sm点）75.0℃、
スメクチツク−ネマチツク点（Sm−Ｎ点）172.3℃、ネ
マチツク−透明点（Ｎ−Ｉ点）184.3℃であつた。収量2
g（収率59％）であつた。このものが目的物であること
をNMRスペクトル、元素分析で確認した。After drying the toluene layer with anhydrous sodium sulfate, the toluene was distilled off under reduced pressure. The remaining crystals were recrystallized with acetone. Crystal-smectic point (C-Sm point) 75.0 ° C,
The smectic-nematic point (Sm-N point) was 172.3 ° C and the nematic-clearing point (NI point) was 184.3 ° C. Yield 2
g (yield 59%). It was confirmed by NMR spectrum and elemental analysis that this was the desired product.
実施例２（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 28％ トランス−４−ペンチル−（４′−シアノフエニル）
シクロヘキサン 42％ トランス−４−ヘプチル−（４′−シアノフエニル）
シクロヘキサン 30％ なる組成の液晶組成物のネマチツク液晶温度範囲は−３
〜52℃である。この液晶組成物をセル厚10μｍのTNセル
（ねじれネマチツクセル）に封入したものの動作しきい
値電圧は1.53V、飽和電圧は2.12Vであつた。又粘度は20
℃で23cpであつた。Example 2 (Example of use) trans-4-propyl- (4'-cyanophenyl)
Cyclohexane 28% trans-4-pentyl- (4'-cyanophenyl)
Cyclohexane 42% trans-4-heptyl- (4'-cyanophenyl)
The liquid crystal composition having a composition of 30% cyclohexane has a nematic liquid crystal temperature range of -3.
~ 52 ° C. Although the liquid crystal composition was sealed in a TN cell (twisted nematic cell) having a cell thickness of 10 μm, the operation threshold voltage was 1.53 V and the saturation voltage was 2.12 V. The viscosity is 20
It was 23 cp at ° C.
この液晶組成物90部に実施例１で製造した４−シクロ
プロピルメトキシ−〔トランス−４−（トランス−４−
プロピルシクロヘキシル）シクロヘキシル〕ベンゼン10
部を加えた液晶混合物のネマチツク温度範囲は−５〜62
℃に広がり、△εは8.8に低下し、しきい値電圧は1.63
V、飽和電圧は2.28Vと上昇しているが、粘度は24cpとわ
ずか上昇しただけであり、大巾にネマチツク液晶温度範
囲を高温側に上昇させることができた。To 90 parts of this liquid crystal composition was added 4-cyclopropylmethoxy- [trans-4- (trans-4-
Propylcyclohexyl) cyclohexyl] benzene 10
The nematic temperature range of the liquid crystal mixture to which the part was added was -5 to 62.
℃, △ ε drops to 8.8, threshold voltage is 1.63
Although the V and saturation voltage increased to 2.28 V, the viscosity increased only to 24 cp, and the temperature range of the nematic liquid crystal could be greatly increased to a higher temperature.
Claims (2)
ル基を示し、ｎは１〜10の整数を示す）で表されるシク
ロプロパン誘導体液晶化合物。(1) General formula (Wherein R represents a linear or branched alkyl group having 1 to 10 carbon atoms and n represents an integer of 1 to 10).
化合物を少なくとも一種含有することを特徴とする液晶
組成物。2. A liquid crystal composition comprising at least one cyclopropane derivative liquid crystal compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4400690A JP2822079B2 (en) | 1990-02-23 | 1990-02-23 | Cyclopropane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4400690A JP2822079B2 (en) | 1990-02-23 | 1990-02-23 | Cyclopropane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03246246A JPH03246246A (en) | 1991-11-01 |
| JP2822079B2 true JP2822079B2 (en) | 1998-11-05 |
Family
ID=12679619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4400690A Expired - Lifetime JP2822079B2 (en) | 1990-02-23 | 1990-02-23 | Cyclopropane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2822079B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100335134B1 (en) * | 1995-01-21 | 2002-10-31 | 엘지.필립스 엘시디 주식회사 | Cyclopropane compound and preparation thereof and liquid crystal compound using the same |
-
1990
- 1990-02-23 JP JP4400690A patent/JP2822079B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03246246A (en) | 1991-11-01 |
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