JPH045074B2 - - Google Patents
Info
- Publication number
- JPH045074B2 JPH045074B2 JP60079239A JP7923985A JPH045074B2 JP H045074 B2 JPH045074 B2 JP H045074B2 JP 60079239 A JP60079239 A JP 60079239A JP 7923985 A JP7923985 A JP 7923985A JP H045074 B2 JPH045074 B2 JP H045074B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- compound
- equatorial
- 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.)
- Expired - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 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 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RFFCUDDJJDOFLS-UHFFFAOYSA-N 1-cyclohexylcyclohexene Chemical class C1CCCCC1C1=CCCCC1 RFFCUDDJJDOFLS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
〔産業上の利用分野〕
本発明は電気光学的表示材料として有用なシク
ロヘキシルシクロヘキセン誘導体を含有する液晶
組成物に関する。
〔従来の技術〕
液晶表示セルの代表的なものにエム・シヤツト
（M.Schadt）等〔APPLIED PHYSICS
LETTERS 18 127〜128（1971）〕によつて提
案された電界効果型セル（フイールド・エフエク
ト・モード・セル）又はジー・エイチ・ハイルマ
イヤー（G.H Heilmeier）等〔PROCEEDING
OF THE I.E.E.E.56 1162〜1171（1968）〕によ
つて提案された動的光散型セル（ダイミツク・ス
キヤツタリング・モード・セル）又はジー・エイ
チ・ハイルマイヤー（G.H Heilmeier）等
〔APPLIED PHYSICS LETTERS13，91
（1968）〕あるいはデイ・エル・ホワイト（DL
White）等〔JOURNAL.OF APPLIED
PHYSICS45，4718（1974）〕によつて提案された
ゲスト・ホスト型セルなどがある。
これらの液晶表示セルに用いられる液晶材料に
は種々の特性が要求されるが、特に戸外で使用さ
れる液晶表示セルにおいては、低温での高速応答
性が要求されている。
応答時間（τ）は液晶材料の粘度（η）と比例
関係（τ∝η）があり、このことから低温で粘度
の低い液晶材料を使用すれば、低温で高速応答の
液晶表示セルを作製することができる。
現在、このような目的で用いられている特にす
ぐれた粘度低下剤には、式
[Industrial Application Field] The present invention relates to a liquid crystal composition containing a cyclohexylcyclohexene derivative useful as an electro-optical display material. [Prior art] Typical liquid crystal display cells include M.Schadt [APPLIED PHYSICS]
LETTERS 18 127-128 (1971)] or the field effect mode cell proposed by GH Heilmeier et al.
OF THE IEEE 56 1162-1171 (1968)] or the dynamic scattering mode cell proposed by GH Heilmeier et al. [APPLIED PHYSICS LETTERS] 13 , 91
(1968)] or Day L White (DL
White) etc. [JOURNAL.OF APPLIED
PHYSICS 45 , 4718 (1974)]. The liquid crystal materials used in these liquid crystal display cells are required to have various properties, and in particular, liquid crystal display cells used outdoors are required to have high-speed response at low temperatures. The response time (τ) has a proportional relationship (τ∝η) with the viscosity (η) of the liquid crystal material, so if a liquid crystal material with low viscosity is used at low temperatures, it is possible to create a liquid crystal display cell with high speed response at low temperatures. be able to. Particularly good viscosity reducing agents currently used for this purpose include the formula
【式】又は[Formula] or
【式】（両式中、Ｒ及び
R′は直鎖状アルキル基を表わす。）で表わされる
化合物等がある。
しかし、式There are compounds represented by the formula: (in both formulas, R and R' represent a linear alkyl group). However, the expression
【式】で表わ
される化合物は、現在ネマチツク液晶材料として
現在汎用されている母体液晶（以下、母体液晶と
いう。）に混合することによつて、混合液晶に対
する粘度低下効果は特に大きい反面、混合液晶の
ネマチツク相−等方性液体相転移温度（以下、Ｎ
−Ｉ転移温度という。）を著しく低下させるとい
う欠点を有していた。また、式
When the compound represented by the formula [formula] is mixed with a base liquid crystal (hereinafter referred to as base liquid crystal) that is currently widely used as a nematic liquid crystal material, it has a particularly large viscosity reducing effect on the mixed liquid crystal. The nematic phase-isotropic liquid phase transition temperature (hereinafter referred to as N
-I transition temperature. ) had the disadvantage of significantly lowering the Also, the expression
本発明の目的は、低粘性で、Ｎ−Ｉ転移温度が
比較的高いネマチツク液晶組成物の提供にある。
〔問題点を解決するための手段〕
本発明は、一般式
（式中、Ｒ及びR′は各々独立的に炭素原子数
１〜９の直鎖状アルキル基を表わし、シクロヘキ
サン環はトランス（エカトリアル−エカトリア
ル）配置である。）
で表わされる化合物を含有するネマチツク液晶組
成物を提供することにより前記問題点を解決し
た。
本発明に係わる式（）の化合物は次の製造方
法に従つて製造することができる。下記（）〜
（）の各式におけるＲ及びR′は夫々、式（）
におけるＲ及びR′と同じ意味をもつ。
第１段階では、式（）のトランス−４−ｎ−
アルキル−１−ブロムシクロヘキサンに無水エー
テルあるいは無水テトラヒドロフラン中でマグネ
シウム粉末と反応させ式（）の化合物の無水エ
ーテルあるいは無水テトラヒドロフラン溶液を製
造する。
第２段階では、第１段階で製造された式（）
の化合物の無水エーテルあるいは無水テトラヒド
ロフラン溶液に式（）の４−ｎ−アルキルシク
ロヘキサノンを反応させた後、塩酸等で分解し式
（）の化合物を製造する。
第３段階では、第２段階で製造された式（）
の化合物をトルエン等の溶媒中でｐ−トルエンス
ルホン酸等によつて脱水し式（）の化合物を製
造する。
斯くして製造される式（）の化合物の代表的
なものの転移温度を第１表に掲げる。
An object of the present invention is to provide a nematic liquid crystal composition having a low viscosity and a relatively high N-I transition temperature. [Means for solving the problems] The present invention provides the general formula (In the formula, R and R' each independently represent a linear alkyl group having 1 to 9 carbon atoms, and the cyclohexane ring has a trans (equatorial-equatorial) configuration.) The above problems have been solved by providing a liquid crystal composition. The compound of formula () according to the present invention can be produced according to the following production method. the below described()~
R and R' in each formula of () are each represented by the formula ()
has the same meaning as R and R' in . In the first step, the trans-4-n- of the formula ()
Alkyl-1-bromocyclohexane is reacted with magnesium powder in anhydrous ether or anhydrous tetrahydrofuran to prepare an anhydrous ether or anhydrous tetrahydrofuran solution of the compound of formula (). In the second stage, the formula () produced in the first stage
A solution of the compound in anhydrous ether or anhydrous tetrahydrofuran is reacted with 4-n-alkylcyclohexanone of the formula (), and then decomposed with hydrochloric acid or the like to produce the compound of the formula (). In the third stage, the formula () produced in the second stage
A compound of formula () is prepared by dehydrating the compound with p-toluenesulfonic acid or the like in a solvent such as toluene. Table 1 lists the transition temperatures of representative compounds of formula () thus produced.
【表】【table】
Claims (1)
１〜９の直鎖状アルキル基を表わし、シクロヘキ
サン環はトランス（エカトリアル−エカトリア
ル）配置である。〕 で表わされる化合物を含有する液晶組成物。[Claims] 1. General formula [In the formula, R and R' each independently represent a linear alkyl group having 1 to 9 carbon atoms, and the cyclohexane ring has a trans (equatorial-equatorial) configuration. ] A liquid crystal composition containing a compound represented by:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7923985A JPS61238738A (en) | 1985-04-16 | 1985-04-16 | Cyclohexylcyclohexene derivative |
| US06/850,585 US4698177A (en) | 1985-04-16 | 1986-04-11 | Cyclohexylcyclohexene derivatives |
| EP86302809A EP0198714B1 (en) | 1985-04-16 | 1986-04-15 | Liquid cristalline compositions containing cyclohexylcyclohexene derivatives, and their use |
| DE8686302809T DE3664906D1 (en) | 1985-04-16 | 1986-04-15 | Liquid cristalline compositions containing cyclohexylcyclohexene derivatives, and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7923985A JPS61238738A (en) | 1985-04-16 | 1985-04-16 | Cyclohexylcyclohexene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61238738A JPS61238738A (en) | 1986-10-24 |
| JPH045074B2 true JPH045074B2 (en) | 1992-01-30 |
Family
ID=13684308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7923985A Granted JPS61238738A (en) | 1985-04-16 | 1985-04-16 | Cyclohexylcyclohexene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61238738A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56133233A (en) * | 1980-02-22 | 1981-10-19 | Merck Patent Gmbh | Phenylcyclohexene derivatives and liquid crystal dielectric body and electronic optical display element containing same |
| JPS6016940A (en) * | 1983-06-14 | 1985-01-28 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Bicyclohexyl compound |
-
1985
- 1985-04-16 JP JP7923985A patent/JPS61238738A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56133233A (en) * | 1980-02-22 | 1981-10-19 | Merck Patent Gmbh | Phenylcyclohexene derivatives and liquid crystal dielectric body and electronic optical display element containing same |
| JPS6016940A (en) * | 1983-06-14 | 1985-01-28 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Bicyclohexyl compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61238738A (en) | 1986-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |