JPH06166647A - Cyclohexene derivative - Google Patents
Cyclohexene derivativeInfo
- Publication number
- JPH06166647A JPH06166647A JP4343592A JP34359292A JPH06166647A JP H06166647 A JPH06166647 A JP H06166647A JP 4343592 A JP4343592 A JP 4343592A JP 34359292 A JP34359292 A JP 34359292A JP H06166647 A JPH06166647 A JP H06166647A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- cyclohexene
- reacting
- 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
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 title claims abstract description 13
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 24
- -1 4-substituted cyclohexanone Chemical class 0.000 abstract description 5
- 239000007818 Grignard reagent Substances 0.000 abstract description 5
- 150000004795 grignard reagents Chemical class 0.000 abstract description 5
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 abstract description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- ROOKGRFFQZPPMX-UHFFFAOYSA-N 4-(4-propoxycyclohexen-1-yl)benzonitrile Chemical compound C1C(OCCC)CCC(C=2C=CC(=CC=2)C#N)=C1 ROOKGRFFQZPPMX-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011777 magnesium Substances 0.000 abstract description 2
- 229910052749 magnesium Inorganic materials 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- YXLVGINZBGVEHL-UHFFFAOYSA-M magnesium;bromobenzene;bromide Chemical compound [Mg+2].[Br-].BrC1=CC=[C-]C=C1 YXLVGINZBGVEHL-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 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】本発明は液晶材料として有用なシ
クロヘキセン誘導体、およびシクロヘキセン誘導体を含
有する液晶組成物に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a cyclohexene derivative useful as a liquid crystal material, and a liquid crystal composition containing the cyclohexene derivative.
【０００２】[0002]
【従来の技術】液晶表示装置は、時計、電卓を始めワー
プロ、テレビ等に広く利用されている。これらの液晶表
示装置のなかで特に多く使用されているのは、液晶材料
の光学的異方性および誘電異方性を利用したＴＮ型（ね
じれネマチック型）液晶表示装置である。現在液晶表示
装置に用いられる液晶材料に要求される特性としては、
液晶温度範囲が広いこと、電気光学的な応答速度が速い
こと、視角範囲が広いこと、駆動電圧が低いこと、化学
的および光学的に安定であることなどが挙げられる。2. Description of the Related Art Liquid crystal display devices are widely used in timepieces, calculators, word processors, televisions and the like. Among these liquid crystal display devices, a TN type (twisted nematic type) liquid crystal display device which utilizes the optical anisotropy and the dielectric anisotropy of the liquid crystal material is particularly often used. The characteristics required for liquid crystal materials currently used in liquid crystal display devices are:
It has a wide liquid crystal temperature range, a high electro-optical response speed, a wide viewing angle range, a low driving voltage, and a chemically and optically stable state.
【０００３】[0003]
【発明が解決しようとする課題】液晶表示装置の駆動電
圧はしきい値電圧Ｖｔｈの値に依存し、しきい値電圧Ｖ
ｔｈは誘電異方性△εの平方根に比例する。そのため誘
電異方性△εの値が正の液晶材料を用いると、しきい値
電圧Ｖｔｈを低い値に抑えることができ、低電圧駆動が
可能になる。The drive voltage of the liquid crystal display device depends on the threshold voltage Vth, and the threshold voltage Vth
th is proportional to the square root of the dielectric anisotropy Δε. Therefore, when a liquid crystal material having a positive value of dielectric anisotropy Δε is used, the threshold voltage Vth can be suppressed to a low value and low voltage driving becomes possible.
【０００４】以上のような特性を全て満足する単一の液
晶化合物は未だ見いだされていない。そのためいろいろ
な特性をもった数種の液晶化合物を混合したり、あるい
はさらに非液晶化合物を混合したりして実用に供してい
るのが現状である。A single liquid crystal compound satisfying all the above characteristics has not been found yet. Therefore, at present, several kinds of liquid crystal compounds having various characteristics are mixed, or further non-liquid crystal compounds are mixed for practical use.
【０００５】そこで本発明は、誘電異方性△εが正の液
晶化合物の提供、および低電圧駆動が可能な液晶組成物
の提供を目的とするものである。Therefore, an object of the present invention is to provide a liquid crystal compound having a positive dielectric anisotropy Δε and a liquid crystal composition which can be driven at a low voltage.
【０００６】[0006]
【課題を解決するための手段】本発明のシクロヘキセン
誘導体は一般式（１）で表されるものである。The cyclohexene derivative of the present invention is represented by the general formula (1).
【０００７】[0007]
【化２】 [Chemical 2]
【０００８】（ただし、Ｒ1 は炭素数１〜１０のアルキ
ル基を示し、Ｘはシアノ基またはハロゲン原子を示し、
Ｙは水素原子またはハロゲン原子を示す。）(Wherein R 1 represents an alkyl group having 1 to 10 carbon atoms, X represents a cyano group or a halogen atom,
Y represents a hydrogen atom or a halogen atom. )
【０００９】また、本発明の液晶組成物は、前記シクロ
ヘキセン誘導体を含有するものである。The liquid crystal composition of the present invention contains the above cyclohexene derivative.
【００１０】本発明のシクロヘキセン誘導体の製造方法
について説明する。ただしＲ1 は炭素数１〜１０のアル
キル基を示し、Ｘはシアノ基またはハロゲン原子を示
し、Ｙは水素原子またはハロゲン原子を示す。The method for producing the cyclohexene derivative of the present invention will be described. However R 1 represents an alkyl group having 1 to 10 carbon atoms, X is a cyano group or a halogen atom, Y represents a hydrogen atom or a halogen atom.
【００１１】本発明の化合物（１）の製造方法の一例を
化３に示す。まずｐ−ジブロモベンゼン（ａ）とマグネ
シウムとを反応させグリニアール試薬（ｂ）を作製し、
次にグリニアール試薬（ｂ）と４−置換シクロヘキサノ
ン（ｃ）とを反応させ、その後脱水反応させることによ
り化合物（ｄ）が得られる。次にこの化合物（ｄ）をシ
アン化第１銅と反応させることにより目的のシクロヘキ
セン誘導体（１）が得られる。An example of the method for producing the compound (1) of the present invention is shown in Chemical formula 3. First, p-dibromobenzene (a) is reacted with magnesium to prepare a Grignard reagent (b),
Next, the compound (d) is obtained by reacting the Grignard reagent (b) with the 4-substituted cyclohexanone (c), followed by dehydration reaction. Then, the compound (d) is reacted with cuprous cyanide to obtain the desired cyclohexene derivative (1).
【００１２】[0012]
【化３】 [Chemical 3]
【００１３】本発明のシクロヘキセン誘導体は多くの液
晶化合物と混合し液晶組成物を製造することができる。
本発明の誘導体と混合可能な液晶化合物としてはエステ
ル系、シクロヘキシルフェニル系、ビフェニル系、ピリ
ミジン系、ジオキサン系、トラン系などが挙げられる。The cyclohexene derivative of the present invention can be mixed with many liquid crystal compounds to produce a liquid crystal composition.
Examples of liquid crystal compounds that can be mixed with the derivative of the present invention include ester-based, cyclohexylphenyl-based, biphenyl-based, pyrimidine-based, dioxane-based, and tolan-based compounds.
【００１４】[0014]
【実施例】次に実施例を挙げ、本発明を具体的に説明す
るが、本発明はこれらの実施例によりなんら制約される
ものではない。EXAMPLES Next, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples.
【００１５】（実施例１）ｐ−ジブロモベンゼン５４ｇ
を無水エーテル２００ｍｌに溶解した。次に、金属マグ
ネシウム粉末６ｇを含有する無水エーテルを攪拌しなが
らｐ−ジブロモベンゼンの無水エーテル溶液を１５〜２
０℃で滴下し、その後室温で１時間反応させてグリニア
ール試薬であるｐ−ブロモフェニルマグネシウムブロマ
イドを生成させた。生成したグリニアール試薬を攪拌し
ながら４−プロピルオキシシクロヘキサノン３０ｇを−
１０〜０℃で滴下した後、室温でさらに１時間反応させ
た。反応終了後、塩酸２０ｍｌを除々に滴下した後、ジ
エチルエーテルで抽出した。抽出液を飽和食塩水で洗浄
した後、無水硫酸ナトリウムを加えて抽出液を乾燥させ
た。これをろ過しろ液から溶媒を減圧留去して４−プロ
ピルオキシ−１−（ｐ−ブロモフェニル）シクロヘキサ
ノールの粗生成物を得た。(Example 1) 54 g of p-dibromobenzene
Was dissolved in 200 ml of anhydrous ether. Next, while stirring anhydrous ether containing 6 g of metallic magnesium powder, an anhydrous ether solution of p-dibromobenzene was added to 15-2.
The solution was added dropwise at 0 ° C. and then reacted at room temperature for 1 hour to generate p-bromophenylmagnesium bromide which is a Grignard reagent. While stirring the produced Grignard reagent, 30 g of 4-propyloxycyclohexanone-
After dropping at 10 to 0 ° C., the mixture was reacted at room temperature for 1 hour. After completion of the reaction, 20 ml of hydrochloric acid was gradually added dropwise and then extracted with diethyl ether. The extract was washed with saturated brine, anhydrous sodium sulfate was added, and the extract was dried. This was filtered and the solvent was distilled off from the filtrate under reduced pressure to obtain a crude product of 4-propyloxy-1- (p-bromophenyl) cyclohexanol.
【００１６】この粗生成物をトルエン４００ｍｌに溶解
し、この溶液に硫酸水素カリウム１２ｇを加えた後、攪
拌しながら還流し、反応によって生成する水をデカンタ
ーで除去した。この脱水反応を１時間行った後、反応混
合物を冷却した。トルエン層を飽和炭酸ナトリウム水溶
液、飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾
燥した後、トルエンを留去し、減圧蒸留して沸点１４５
℃／１ｍｍＨｇの留分を採った。これをアセトンから再
結晶させ、４−プロピルオキシ−１−（ｐ−ブロモフェ
ニル）シクロヘキセン３８ｇを得た。This crude product was dissolved in 400 ml of toluene, and 12 g of potassium hydrogen sulfate was added to this solution, which was then refluxed with stirring, and water produced by the reaction was removed by a decanter. After performing this dehydration reaction for 1 hour, the reaction mixture was cooled. The toluene layer was washed successively with saturated aqueous sodium carbonate solution and saturated brine and dried over anhydrous sodium sulfate, then toluene was distilled off and the residue was distilled under reduced pressure to give a boiling point of 145.
A fraction of ° C / 1 mmHg was collected. This was recrystallized from acetone to obtain 38 g of 4-propyloxy-1- (p-bromophenyl) cyclohexene.
【００１７】次にこの化合物をＮ−メチルピロリドン１
００ｍｌに溶解し、シアン化第１銅１４ｇを加えて２時
間還流する。その後約６０ｍｌのＮ−メチルピロリドン
を留去し、次いで塩化第２鉄水を加え６０℃で攪拌し、
トルエン抽出し酸洗浄し、さらに飽和食塩水で洗浄し、
無水硫酸ナトリウムで乾燥した後、トルエンを留去し、
エタノールから再結晶して化４で表される４−プロピル
オキシ−１−（ｐ−シアノフェニル）シクロヘキセン２
２ｇを得た。この化合物の融点５０．３℃であった。ま
た、この化合物の赤外線吸収スペクトルを図１に示す。Next, this compound was added to N-methylpyrrolidone 1
Dissolve in 00 ml, add 14 g of cuprous cyanide and reflux for 2 hours. Thereafter, about 60 ml of N-methylpyrrolidone was distilled off, ferric chloride water was added, and the mixture was stirred at 60 ° C.,
Extracted with toluene, washed with acid, washed with saturated saline,
After drying over anhydrous sodium sulfate, the toluene was distilled off,
4-Propyloxy-1- (p-cyanophenyl) cyclohexene 2 represented by Chemical formula 4 after recrystallization from ethanol
2 g was obtained. The melting point of this compound was 50.3 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００１８】[0018]
【化４】 [Chemical 4]
【００１９】（実施例２）化５で表される化合物のみか
らなる液晶組成物の特性はＮ−Ｉ点５２℃、△ｎ０．１
２０、粘度２３．０ｃｐｓ、Ｖth１．４５Ｖであった。
この液晶組成物９０重量部に、本発明の化合物である４
−プロピルオキシ−１−（ｐ−シアノフェニル）シクロ
ヘキセン１０重量部を加えた液晶組成物のＮ−Ｉ点は４
４℃、△ｎ０．１１５で粘度は２５．０ｃｐｓであり、
Ｖthは１．２４Ｖと低くなった。なお、しきい値電圧Ｖ
thはこの液晶組成物をセル厚９μｍのＴＮ型液晶表示装
置に搭載した際の値である。(Example 2) The characteristics of the liquid crystal composition consisting only of the compound represented by Chemical formula 5 have an NI point of 52 ° C. and a Δn of 0.1.
The viscosity was 20, the viscosity was 23.0 cps, and the Vth was 1.45V.
90 parts by weight of this liquid crystal composition was added with 4 parts of the compound of the present invention.
The liquid crystal composition containing 10 parts by weight of -propyloxy-1- (p-cyanophenyl) cyclohexene had an NI point of 4
At 4 ° C and Δn0.115, the viscosity is 25.0 cps,
Vth became as low as 1.24V. The threshold voltage V
th is a value when this liquid crystal composition is mounted on a TN type liquid crystal display device having a cell thickness of 9 μm.
【００２０】[0020]
【化５】 [Chemical 5]
【００２１】[0021]
【発明の効果】本発明のシクロヘキセン誘導体は、誘電
異方性Δεが正を示す。そのため本発明の誘導体を含有
する液晶組成物は液晶材料として優れた特性を有し、ま
たその液晶組成物を用いた液晶表示装置は良好な表示特
性を示し、特に低電圧駆動に優れる。さらに本発明の誘
導体は種々の液晶化合物との相互溶解性が大きく、液晶
組成物の構成成分として多くの液晶材料と組み合わせて
使用することができ、液晶組成物の特性改良に有用なも
のである。The cyclohexene derivative of the present invention has a positive dielectric anisotropy Δε. Therefore, the liquid crystal composition containing the derivative of the present invention has excellent properties as a liquid crystal material, and a liquid crystal display device using the liquid crystal composition exhibits excellent display properties, and particularly excellent in low voltage driving. Further, the derivative of the present invention has a large mutual solubility with various liquid crystal compounds, can be used in combination with many liquid crystal materials as a constituent component of the liquid crystal composition, and is useful for improving the characteristics of the liquid crystal composition. .
【図１】 本発明シクロヘキセン誘導体の赤外線吸収ス
ペクトルを表す図である。FIG. 1 is a diagram showing an infrared absorption spectrum of a cyclohexene derivative of the present invention.
Claims (2)
誘導体。 【化１】 （ただし、Ｒ1 は炭素数１〜１０のアルキル基を示し、
Ｘはシアノ基またはハロゲン原子を示し、Ｙは水素原子
またはハロゲン原子を示す。）1. A cyclohexene derivative represented by the general formula (1). [Chemical 1] (However, R 1 represents an alkyl group having 1 to 10 carbon atoms,
X represents a cyano group or a halogen atom, and Y represents a hydrogen atom or a halogen atom. )
含有する液晶組成物。2. A liquid crystal composition containing the cyclohexene derivative according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4343592A JPH06166647A (en) | 1992-12-01 | 1992-12-01 | Cyclohexene derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4343592A JPH06166647A (en) | 1992-12-01 | 1992-12-01 | Cyclohexene derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06166647A true JPH06166647A (en) | 1994-06-14 |
Family
ID=18362722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4343592A Pending JPH06166647A (en) | 1992-12-01 | 1992-12-01 | Cyclohexene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06166647A (en) |
-
1992
- 1992-12-01 JP JP4343592A patent/JPH06166647A/en active Pending
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