JPH0142941B2 - - Google Patents
Info
- Publication number
- JPH0142941B2 JPH0142941B2 JP15427784A JP15427784A JPH0142941B2 JP H0142941 B2 JPH0142941 B2 JP H0142941B2 JP 15427784 A JP15427784 A JP 15427784A JP 15427784 A JP15427784 A JP 15427784A JP H0142941 B2 JPH0142941 B2 JP H0142941B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- benzoic acid
- compound
- fluoro
- crystal composition
- 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
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- LJXCFVJGBORMRW-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) benzoate Chemical compound C1=C(C#N)C(F)=CC(OC(=O)C=2C=CC=CC=2)=C1 LJXCFVJGBORMRW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- REIVHYDACHXPNH-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(F)=C1 REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 ester compound Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UGPYJKPYNQWEGN-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 4-(propoxymethyl)benzoate Chemical compound C1=CC(COCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 UGPYJKPYNQWEGN-UHFFFAOYSA-N 0.000 description 1
- ONRPXRPUBXXCCM-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(F)=C1 ONRPXRPUBXXCCM-UHFFFAOYSA-N 0.000 description 1
- LNEMDIUSUQPKIP-UHFFFAOYSA-N 2-phenyl-1,3-dioxane Chemical compound O1CCCOC1C1=CC=CC=C1 LNEMDIUSUQPKIP-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- KAWUBNUJMFOOOE-UHFFFAOYSA-N 3-amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC(Br)=C(O)C(Br)=C1 KAWUBNUJMFOOOE-UHFFFAOYSA-N 0.000 description 1
- WOYPUSSSRAPAOQ-UHFFFAOYSA-N 4-(propoxymethyl)benzoyl chloride Chemical compound CCCOCC1=CC=C(C(Cl)=O)C=C1 WOYPUSSSRAPAOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
【発明の詳細な説明】
〔発明の利用分野〕
本発明は新規な液晶化合物に関し、更に詳しく
は誘電率の異方性が正の液晶材料に添加する一成
分として使用することができる新規な液晶化合物
およびそれを含有する液晶組成物に関する。[Detailed Description of the Invention] [Field of Application of the Invention] The present invention relates to a novel liquid crystal compound, and more particularly to a novel liquid crystal compound that can be used as a component added to a liquid crystal material with positive dielectric constant anisotropy. The present invention relates to a compound and a liquid crystal composition containing the same.
周知のように、液晶化合物はその液晶相におけ
る誘電率の異方性および屈折率の異方性を利用し
て種々の表示装置に使用されている。これらの表
示装置は液晶の電気光学効果や熱光学効果を応用
したものであり、その表示方式によつてTN型
（ねじれネマチツク型）、DS（動的散乱型）、ゲス
ト・ホスト型、DAP型など各種の方式に分けら
れる。しかし、いずれの方式においても、それに
使用される液晶材料は単独の化合物ではその要求
される諸特性即ち、液晶温度範囲、動作電圧、応
答性能等で実用的な使用に耐えるものではなく、
実用的には数種の液晶化合物あるいは非液晶化合
物を混合してある程度の使用に耐え得る物を得て
いるのが現状である。
As is well known, liquid crystal compounds are used in various display devices by utilizing dielectric constant anisotropy and refractive index anisotropy in the liquid crystal phase. These display devices apply the electro-optic effect and thermo-optic effect of liquid crystals, and depending on the display method, there are TN type (twisted nematic type), DS (dynamic scattering type), guest-host type, and DAP type. It can be divided into various methods such as However, in either method, the liquid crystal material used as a single compound cannot withstand practical use in terms of the required properties, such as liquid crystal temperature range, operating voltage, response performance, etc.
Practically speaking, the current situation is to mix several types of liquid crystal compounds or non-liquid crystal compounds to obtain products that can withstand a certain level of use.
本発明の目的は実用的な性能の優れた且つ安定
な液晶組成物を構成する一成分として有用な特に
その作動電圧を低下させるに有用な液晶化合物を
提供することである。
An object of the present invention is to provide a liquid crystal compound useful as a component constituting a liquid crystal composition having excellent practical performance and stability, and particularly useful for lowering the operating voltage thereof.
即ち、本発明は一般式
（上式中、Ｒは１〜10個の炭素原子を有するアル
キル基を示す。）
で表わされる４−（α−アルコキシメチル）安息
香酸３−フルオロ−４−シアノフエニルエステル
および少くとも該化合物を１成分含有することを
特徴とする液晶組成物である。
That is, the present invention is based on the general formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms.) 4-(α-alkoxymethyl)benzoic acid 3-fluoro-4-cyanophenyl ester represented by and at least the compound This is a liquid crystal composition characterized in that it contains one component.
本発明によつて提供される化合物は、35〜40程
度の大きな正の誘電異方性値をもつた液晶化合物
であり他の液晶化合物と混合して、低いしきい電
圧、飽和電圧を持つ液晶組成物を構成するのに有
用な化合物である。従つて本化合物単独では表示
素子に使用されることはないが、相溶性に優れて
いるので他のネマチツク液晶、例えばシツフ塩基
系、アゾキシ系、安息香酸フエニルエステル系、
シクロヘキサンカルボン酸フエニルエステル系シ
クロヘキサンカルボン酸シクロヘキシルエステル
系、ビフエニル系、フエニルシクロヘキサン系、
フエニルメタジオキサン系、フエニルピリミジン
系等の液晶の一種類又は数種類の系と混合させる
ことにより得られる液晶組成物の駆動電圧を大幅
に低下せしめる効果を有する。
The compound provided by the present invention is a liquid crystal compound with a large positive dielectric anisotropy value of about 35 to 40, and can be mixed with other liquid crystal compounds to produce a liquid crystal with a low threshold voltage and saturation voltage. Compounds useful in forming compositions. Therefore, this compound is not used alone in display elements, but because of its excellent compatibility, it can be used with other nematic liquid crystals, such as Schiff base-based, azoxy-based, benzoic acid phenyl ester-based,
Cyclohexanecarboxylic acid phenyl ester system, cyclohexanecarboxylic acid cyclohexyl ester system, biphenyl system, phenylcyclohexane system,
It has the effect of significantly lowering the driving voltage of a liquid crystal composition obtained by mixing it with one type or several types of liquid crystals such as phenylmetadioxane type and phenylpyrimidine type.
本発明の化合物は次に示す反応によつて製造す
ることができる。
The compound of the present invention can be produced by the following reaction.
すなわち、４−（α−アルコキシメチル）安息
香酸クロリド（）と３−フルオロ−４−シアノ
フエノール（）とをピリジンの存在下で反応さ
せれば目的のエステル化合物（）が得られる。
ここで用いた４−（α−アルコキシメチル）安息
香酸クロリドは、特開昭57−77658号公報に記載
の方法により合成した。又３−フルオロ−４−シ
アノフエノールは２−フルオロ−４−ヒドロキシ
ベンズアルデヒドのオキシムを無水酢酸にて脱水
して製造することができる。 That is, by reacting 4-(α-alkoxymethyl)benzoic acid chloride () with 3-fluoro-4-cyanophenol () in the presence of pyridine, the desired ester compound () can be obtained.
The 4-(α-alkoxymethyl)benzoic acid chloride used here was synthesized by the method described in JP-A-57-77658. Further, 3-fluoro-4-cyanophenol can be produced by dehydrating the oxime of 2-fluoro-4-hydroxybenzaldehyde with acetic anhydride.
以下実施例により本発明の化合物の製造方法お
よび応用例により用途を詳細に説明する。
Hereinafter, the method for producing the compound of the present invention and its uses will be explained in detail with reference to Examples.
実施例 １
〔４−（α−プロポキシメチル）安息香酸３−
フルオロ−４−シアノフエニルエステルの製
造〕
３−フルオロ−４−シアノフエノール1.5ｇ
（11ｍmol）を、乾燥したピリジン５mlに溶解し
ておき、これに４−（α−プロポキシメチル）安
息香酸クロリド2.3ｇ（11ｍmol）を乾燥トルエ
ン10mlに溶解した溶液を加え60℃にて３時間加熱
反応させた。反応終了後、反応物を水100ml中に
投入しトルエン層を分離し、6N塩酸、2N水酸化
ナトリウム水溶液、次いで水で洗浄してからトル
エン層を無水硫酸ナトリウム上で乾燥した。トル
エン層からトルエンを留去し、残つた油状物をエ
チルアルコール５mlから再結晶して、目的の４−
（α−プロポキシメチル）安息香酸３−フルオロ
−４−シアノフエニルエステル1.8ｇが得られた。
この物の融点は35.8〜36.2℃、Ｎ−Ｉ点（ネマチ
ツク−透明点）は13℃（モノトロピツク転移点）
であつた。収率：52％。Example 1 [4-(α-propoxymethyl)benzoic acid 3-
Production of fluoro-4-cyanophenyl ester] 1.5 g of 3-fluoro-4-cyanophenol
(11 mmol) was dissolved in 5 ml of dry pyridine, and a solution of 2.3 g (11 mmol) of 4-(α-propoxymethyl)benzoic acid chloride dissolved in 10 ml of dry toluene was added thereto and heated at 60°C for 3 hours. Made it react. After the reaction was completed, the reaction product was poured into 100 ml of water, and the toluene layer was separated, washed with 6N hydrochloric acid, 2N aqueous sodium hydroxide solution, and then water, and then dried over anhydrous sodium sulfate. Toluene was distilled off from the toluene layer, and the remaining oil was recrystallized from 5 ml of ethyl alcohol to obtain the desired 4-
1.8 g of (α-propoxymethyl)benzoic acid 3-fluoro-4-cyanophenyl ester was obtained.
The melting point of this product is 35.8-36.2℃, and the N-I point (nematic clearing point) is 13℃ (monotropic transition point).
It was hot. Yield: 52%.
実施例 ２
実施例１に準じた方法により４−（α−メトキ
シメチル）安息香酸３−フルオロ−４−シアノフ
エニルエステルを製造した。この物の融点は89.5
℃、Ｎ−Ｉ点は27.7℃（モノトロピツク）であつ
た。Example 2 4-(α-methoxymethyl)benzoic acid 3-fluoro-4-cyanophenyl ester was produced by a method similar to Example 1. The melting point of this substance is 89.5
°C, the N-I point was 27.7 °C (monotropic).
実施例 ３（応用例１）
上記組成のネマチツク液晶組成物のＡのＮ−
点は72.0℃、Δεは11.6、20℃における粘度は28cp
である。この液晶組成物をセル厚10nｍのTNセ
ルに封入したものの動作しきい電圧は1.75V、飽
和電圧は2.40Vであつた。該液晶組成物85重量部
に本発明の化合物の１つである実施例１に示した
４−（α−プロポキシメチル）安息香酸３−フル
オロ−４−シアノフエニルエステル15重量部を加
えた液晶組成物のＮ−Ｉ点は62.0℃、20℃におけ
る粘度は34cpで、これを前記のTNセルに封入し
たものの動作しきい電圧は1.28V、飽和電圧は
1.8Vに低下した。Example 3 (Application example 1) N- of A of the nematic liquid crystal composition having the above composition.
The point is 72.0℃, Δε is 11.6, and the viscosity at 20℃ is 28cp
It is. When this liquid crystal composition was sealed in a TN cell with a cell thickness of 10 nm, the operating threshold voltage was 1.75V and the saturation voltage was 2.40V. A liquid crystal obtained by adding 15 parts by weight of 4-(α-propoxymethyl)benzoic acid 3-fluoro-4-cyanophenyl ester shown in Example 1, which is one of the compounds of the present invention, to 85 parts by weight of the liquid crystal composition. The N-I point of the composition is 62.0℃, the viscosity at 20℃ is 34cp, and when this is sealed in the TN cell described above, the operating threshold voltage is 1.28V, and the saturation voltage is
It dropped to 1.8V.
実施例 ４
実施例３で使用したネマチツク液晶組成物A90
重量部に本発明の実施例２で得られた４−（α−
メトキシメチル）安息香酸３−フルオロ−４−シ
アノフエニルエステル10重量部を加えて得られる
液晶組成物のＮ−Ｉ点は62.0、Δεは16.0、20℃に
於ける粘度は34cpであつた。又、これを実施例
３で使用したのと同様のTNセルに封入したもの
の動作しきい電圧は1.36V、飽和電圧は2.00Vに
低下した。Example 4 Nematic liquid crystal composition A90 used in Example 3
4-(α- obtained in Example 2 of the present invention in parts by weight)
The liquid crystal composition obtained by adding 10 parts by weight of methoxymethyl)benzoic acid 3-fluoro-4-cyanophenyl ester had an N-I point of 62.0, a Δε of 16.0, and a viscosity at 20°C of 34 cp. Furthermore, when this was sealed in a TN cell similar to that used in Example 3, the operating threshold voltage decreased to 1.36V and the saturation voltage decreased to 2.00V.
比較例
実施例４に於ける４−（α−メトキシメチル）
安息香酸３−フルオロ−４−シアノフエニルエス
テルに代えて４−プロピル安息香酸３−クロロ−
４−シアノフエニルエステルを10重量部加えた液
晶組成物を調製したところ、そのＮ−Ｉ点は48
℃、Δεは14.2、20℃に於ける粘度は39cpであつ
た。又この組成物を使用して得られた実施例４と
同様なTNセルのしきい電圧は1.51V、飽和電圧
は2.13Vであつた。Comparative example 4-(α-methoxymethyl) in Example 4
4-propylbenzoic acid 3-chloro- in place of benzoic acid 3-fluoro-4-cyanophenyl ester
When a liquid crystal composition containing 10 parts by weight of 4-cyanophenyl ester was prepared, its N-I point was 48.
°C and Δε were 14.2, and the viscosity at 20 °C was 39 cp. A TN cell similar to Example 4 obtained using this composition had a threshold voltage of 1.51V and a saturation voltage of 2.13V.
以上の実施例３、４、比較例の結果から本発明
の化合物を使用することにより、その液晶組成物
の駆動電圧を低下させる効果の著しいことが判
る。 From the results of Examples 3 and 4 and Comparative Examples above, it can be seen that the use of the compound of the present invention has a remarkable effect of lowering the driving voltage of the liquid crystal composition.
Claims (1)
キル基を示す。） で表わされる４−（α−アルコキシメチル）安息
香酸３−フルオロ４−シアノフエニルエステル。 ２ 一般式 （上式中、Ｒは１〜10個の炭素原子を有するアル
キル基を示す。） で表わされる４−（α−アルコキシメチル）安息
香酸３−フルオロ４−シアノフエニルエステルを
少くとも一成分含有することを特徴とする２成分
以上よりなる液晶組成物。[Claims] 1. General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms.) 4-(α-alkoxymethyl)benzoic acid 3-fluoro4-cyanophenyl ester. 2 General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms.) Contains at least one component of 4-(α-alkoxymethyl)benzoic acid 3-fluoro-4-cyanophenyl ester represented by A liquid crystal composition comprising two or more components.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15427784A JPS6133159A (en) | 1984-07-25 | 1984-07-25 | Cyanophenyl ester derivative |
| US06/706,609 US4661283A (en) | 1984-03-02 | 1985-02-28 | Benzoate derivatives having a large positive dielectric anisotropy value and liquid crystal compositions containing same |
| EP85301457A EP0155792B1 (en) | 1984-03-02 | 1985-03-04 | Benzoate derivatives having positive dielectric anisotropy and liquid crystal compositions containing them |
| DE8585301457T DE3560259D1 (en) | 1984-03-02 | 1985-03-04 | Benzoate derivatives having positive dielectric anisotropy and liquid crystal compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15427784A JPS6133159A (en) | 1984-07-25 | 1984-07-25 | Cyanophenyl ester derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6133159A JPS6133159A (en) | 1986-02-17 |
| JPH0142941B2 true JPH0142941B2 (en) | 1989-09-18 |
Family
ID=15580639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15427784A Granted JPS6133159A (en) | 1984-03-02 | 1984-07-25 | Cyanophenyl ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6133159A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL9201059A (en) * | 1992-06-15 | 1994-01-03 | Bootsman Holding Bv | POSITION DETECTION SYSTEM. |
-
1984
- 1984-07-25 JP JP15427784A patent/JPS6133159A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6133159A (en) | 1986-02-17 |
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