JPH0452269B2 - - Google Patents
Info
- Publication number
- JPH0452269B2 JPH0452269B2 JP19383983A JP19383983A JPH0452269B2 JP H0452269 B2 JPH0452269 B2 JP H0452269B2 JP 19383983 A JP19383983 A JP 19383983A JP 19383983 A JP19383983 A JP 19383983A JP H0452269 B2 JPH0452269 B2 JP H0452269B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- point
- dicyanopyrazinyl
- compound
- 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 23
- 239000000203 mixture Substances 0.000 claims description 16
- -1 2,3-dicyano-5-substituted pyrazine Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 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 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 239000013078 crystal Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IKKDQJGLFIXJKP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-2-oxoacetaldehyde;hydrate Chemical compound O.OC1=CC=C(C(=O)C=O)C=C1 IKKDQJGLFIXJKP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 229910052799 carbon Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 1
- STJIWQOFZIYYFH-UHFFFAOYSA-N 1-(2-phenylphenyl)cyclohexane-1-carbonitrile Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C1(C#N)CCCCC1 STJIWQOFZIYYFH-UHFFFAOYSA-N 0.000 description 1
- SHFGENOBPXWUJF-UHFFFAOYSA-N 2-(2-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SHFGENOBPXWUJF-UHFFFAOYSA-N 0.000 description 1
- ABUDUIUSKAVAPC-UHFFFAOYSA-N 2-oxo-2-phenylacetic acid;hydrate Chemical compound O.OC(=O)C(=O)C1=CC=CC=C1 ABUDUIUSKAVAPC-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
- VRGQQLFRUKMDSW-UHFFFAOYSA-N 4-(4-pentylphenyl)benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 VRGQQLFRUKMDSW-UHFFFAOYSA-N 0.000 description 1
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 1
- OZPPUPJQRJYTNY-UHFFFAOYSA-N 4-pentoxybenzoic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)C=C1 OZPPUPJQRJYTNY-UHFFFAOYSA-N 0.000 description 1
- QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VACLULPMEXHBMD-JOCQHMNTSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C(O)=O)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C(O)=O)C=C1 VACLULPMEXHBMD-JOCQHMNTSA-N 0.000 description 1
- JXPGQFKJNKWDKP-KTSLABGISA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 JXPGQFKJNKWDKP-KTSLABGISA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-M phenyl carbonate Chemical compound [O-]C(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Description
本発明は新規な有機化合物に関し更に詳しくな
誘電異方性が正の新規な化合物及びそれを含有す
る液晶組成物に関するものである。正の誘電異方
性を有する液晶物質は捩れた配列を持つたネマチ
ツク液晶を用いる液晶表示素子、いわゆるTN型
セルに利用できるほか、適当な色素物質を添加し
て、ゲスト・ホスト効果を応用したカラー液晶表
示素子にも利用される。これらの液晶材料は単独
の化合物ではその諸性能、すなわち液晶温度範
囲、動作電圧、応答性能等で実用的な使用に耐え
る物はない。実際には数種の液晶化合物または非
液晶化合物を混合して、使用に耐え得る物を得て
いるのが現状である。本発明の目的は、この様な
目的に適した実用的に安定な化合物を提供するこ
とにある。
本発明は上記の目的にあつた誘電率の異方性値
が大きな正の値を有し、液晶温度範囲が広く、か
つネマチツク−透明点（Ｎ−Ｉ点）の高い安定性
にすぐれた新規な液晶化合物を提供するものであ
る。本発明は、
一般式
（式中、Ｒは炭素数１〜９のアルキル基または
アルコキシ基を表わし、Ｘは−０−、−CH2−、
The present invention relates to a novel organic compound, and more particularly to a novel compound having positive dielectric anisotropy and a liquid crystal composition containing the same. Liquid crystal materials with positive dielectric anisotropy can be used in liquid crystal display devices that use nematic liquid crystals with twisted alignment, so-called TN cells, and can also be used to apply the guest-host effect by adding appropriate dye materials. It is also used in color liquid crystal display devices. These liquid crystal materials cannot be used as a single compound in terms of their performance, ie, liquid crystal temperature range, operating voltage, response performance, etc., for practical use. In reality, at present, products that can withstand use are obtained by mixing several types of liquid crystal compounds or non-liquid crystal compounds. An object of the present invention is to provide a practically stable compound suitable for such purposes. The present invention meets the above objectives and is a novel material having a large positive dielectric anisotropy value, a wide liquid crystal temperature range, and a high stability of the nematic clearing point (N-I point). The present invention provides a liquid crystal compound. The present invention is based on the general formula (In the formula, R represents an alkyl group or an alkoxy group having 1 to 9 carbon atoms, and X is -0-, -CH 2 -,
【式】【formula】
【式】【formula】
【式】【formula】
【式】または[expression] or
【式】を表わす）
で示される２，３−ジシアノ−５−置換ピラジン
誘導体およびそれを含有する液晶組成物である。
本発明の化合物は広いネマチツク温度範囲を有す
るが、結晶−ネマチツク点（Ｃ−Ｎ点）が高いた
めにこの化合物単独では表示素子用としての実用
性はない。しかし他の液晶化合物との相溶性にす
ぐれ又そのネマチツク−透明点（Ｎ−Ｉ点）が高
い為に他の液晶物質、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、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
ピリミジン系、フエニルメタジオキサン系などの
液晶の一種類、あるいは数種の系の混合物と混合
させる事により、その透明点を上昇せしめる、い
わゆる高温液晶成分として有用であり、更に従来
同様な目的で広く用いられているシアノターフエ
ニル系、シアノビフエニリルシクロヘキサン系な
どの液晶物質に比べ、誘電率の異方性値（△ε）
が大きく本発明の化合物を使用する事により少量
でもその液晶組成物の駆動電圧を大巾に下げる事
ができる。
この様に秀れた特徴を有する本発明の化合物は
次に示す反応によつて製造することができる。
先づ、４−ヒドロキシアセトフエノンＡに適当
な酸化剤、好しくは二酸化セレンを反応させ４−
ヒドロキシフエニルグリオキサール水和物Ｂを得
る。次にＢとジアミノマレオニトリルＣとをテト
ラヒドロフランなどの適当な不活性有機溶媒中に
て反応させＤのフエノール誘導体を得る。次に対
応するカルボン酸クロリドをピリジン存在下でＤ
と反応させれば目的の化合物Ｉが得られる。
以下実施例により本発明の化合物Ｉの製造方法
ならびに応用例を詳細に説明する。
以下、結晶−ネマチツク転移点をＣ−Ｎ点ネマ
チツク−透明点をＮ−Ｉ点、結晶−透明点をＣ−
Ｉ点と略記する。
実施例 １
４−（トランス−４−プロピルシクロヘキシル）
安息香酸４−（２，３−ジシアノピラジニル−５）
フエニルエステル
(1)４−ヒドロキシフエニルグリオキサール水和物
の製造
二酸化セレン11.1ｇ（0.1モル）を、ｐ−ジオ
キサン60c.c.、水２c.c.の混合溶液に加え60℃にて加
熱溶解させた。次に４−ヒドロキシアセトフエノ
ン13.6ｇ（0.1モル）を一度に加え、この混合物
を還流下に４時間加熱反応させた。反応終了後析
出した無機物を過し、液からｐ−ジオキサン
を溜去した。赤褐色の油状物に水80c.c.を加え、こ
の混合物を80℃にて２時間加熱撹拌させた。反応
終了後室温にまで放冷し析出した結晶を別し乾
燥し、10.7ｇの目的物を得た。融点：109〜111
℃。
(2)４−（２，３−ジシアノピラジニル−５）フエ
ノールの製造
(1)で得られた４−ヒドロキシフエニルグリオキ
サール水和物8.6ｇ（0.057モル）、およびジアミ
ノマレオニトリル6.2ｇ（0.057モル）を20c.c.のテ
トラヒドロフランに溶解させ、これらの混合物を
室温にて６時間撹拌した。反応終了後、反応混合
物からテトラヒドロフランを溜去し、残つた固型
物を50c.c.のエタノールから再結晶して7.7ｇの目
的物を得た。
融点；204〜205℃。
(3)４−（トランス−４−プロピルシクロヘキシル）
安息香酸４−（２，３−ジシアノピラジニル−
５）フエニルエステルの製造
４−（トランス−４−プロピルシクロヘキシル）
安息香酸１ｇに塩化チオニル２ｇを加え還流下に
２時間反応させた。反応終了後、過剰の塩化チオ
ニルを溜去し酸クロリドを得た。一方(2)で得られ
た４−（２，３−ジシアノピラジニル−５）フエ
ノール１ｇを乾燥したピリジン３c.c.に溶解した溶
液に、先に得られた酸クロリドを加え、60℃にて
３時間加熱反応させた。反応終了後反応物を水
100c.c.中に投じ、析出した結晶をトルエン10c.c.に
て抽出した。抽出液を希塩酸、希水酸化ナトリウ
ム水溶液、次いで水にて洗浄し、トルエン層を無
水硫酸ナトリウム上で乾燥した。続いてトルエン
を溜去し残つた固型物をベンゼン５c.c.から再結晶
して1.1ｇの目的物を得た。Ｃ−Ｎ点；164.8〜
165.3℃、Ｎ−Ｉ点；273.0℃。
実施例 ２〜４
実施例１に準じた方法にて次に示す化合物を合
成した。
４−ブチル安息香酸４−（２，３−ジシアノピ
ラジニル−５）フエニルエステル
Ｃ−Ｉ；122.5〜123.0℃
４−ペンチルオキシ安息香酸４−（２，３−ジ
シアノピラジニル−５）フエニルエステル
Ｃ−Ｉ；126.4〜127.2℃
Ｎ−Ｉ；123.5〜123.8℃
トランス−４−（トランス−４−プロピルシクロ
ヘキシル）シクロヘキサンカルボン酸４−（２，
３−ジシアノピラジニル−５）フエニルエステル
Ｃ−Ｎ；165.7〜166.9℃
Ｎ−Ｉ；277.8〜278.1℃
実施例 ５〜９
実施例１に準じた方法により次の５種の化合物
を合成した。
ブチル−４−（２，３−ジシアノピラジニル−５）
フエニルカーボネート。ペンタン酸４−（２，３
−ジシアノピラジニル−５）フエニルエステル。
トランス−４−プロピルシクロヘキサンカルボ
ン酸４−（２，３−ジシアノピラジニル−５）フ
エニルエステル。
トランス−４−（４−ブチルフエニル）シクロ
ヘキサンカルボン酸４−（２，３−ジシアノピラ
ジニル−５）フエニルエステル。
４−（４−ペンチルフエニル）安息香酸４−
（２，３−ジシアノピラジニル−５）フエニルエ
ステル。
これらの化合物の相転移点を実施例１〜４の結
果とともに第１表に示す。A 2,3-dicyano-5-substituted pyrazine derivative represented by the following formula and a liquid crystal composition containing the same.
Although the compound of the present invention has a wide nematic temperature range, it has a high crystal-nematic point (C-N point), so this compound alone is not practical for use in display devices. However, because of its excellent compatibility with other liquid crystal compounds and its high nematic clearing point (N-I point), other liquid crystal substances such as Schiff bases, azoxys, benzoic acid phenyl esters, cyclohexane carboxylic acids, etc. By mixing with one type of liquid crystal such as phenyl ester, cyclohexyl cyclohexanecarboxylic acid ester, biphenyl, phenylcyclohexane, phenylpyrimidine, and phenylmetadioxane, or a mixture of several types of liquid crystals, It is useful as a so-called high-temperature liquid crystal component that increases the clearing point, and it has anisotropy in dielectric constant compared to liquid crystal materials such as cyanoterphenyl and cyanobiphenylylcyclohexane, which have been widely used for similar purposes. Value (△ε)
By using the compound of the present invention, the driving voltage of the liquid crystal composition can be significantly lowered even with a small amount. The compound of the present invention having such excellent characteristics can be produced by the following reaction. First, 4-hydroxyacetophenone A is reacted with a suitable oxidizing agent, preferably selenium dioxide.
Hydroxyphenylglyoxal hydrate B is obtained. Next, B and diaminomaleonitrile C are reacted in a suitable inert organic solvent such as tetrahydrofuran to obtain the phenol derivative D. Next, the corresponding carboxylic acid chloride was added to D in the presence of pyridine.
By reacting with, the target compound I can be obtained. Hereinafter, the method for producing Compound I of the present invention and its application examples will be explained in detail with reference to Examples. Hereinafter, the crystal-nematic transition point is the C-N point, the nematic-clearing point is the N-I point, and the crystal-clearing point is the C-
It is abbreviated as point I. Example 1 4-(trans-4-propylcyclohexyl)
4-(2,3-dicyanopyrazinyl-5) benzoate
Phenyl ester (1) Production of 4-hydroxyphenylglyoxal hydrate 11.1 g (0.1 mol) of selenium dioxide was added to a mixed solution of 60 c.c. of p-dioxane and 2 c.c. of water and heated at 60°C. Dissolved. Next, 13.6 g (0.1 mol) of 4-hydroxyacetophenone was added at once, and the mixture was reacted under reflux for 4 hours. After the reaction was completed, the precipitated inorganic substances were filtered, and p-dioxane was distilled off from the liquid. 80 c.c. of water was added to the reddish-brown oil, and the mixture was heated and stirred at 80° C. for 2 hours. After the reaction was completed, the mixture was allowed to cool to room temperature, and the precipitated crystals were separated and dried to obtain 10.7 g of the desired product. Melting point: 109-111
℃. (2) Production of 4-(2,3-dicyanopyrazinyl-5)phenol 8.6 g (0.057 mol) of 4-hydroxyphenylglyoxal hydrate obtained in (1) and 6.2 g ( 0.057 mol) was dissolved in 20 c.c. of tetrahydrofuran and the mixture was stirred at room temperature for 6 hours. After the reaction was completed, tetrahydrofuran was distilled off from the reaction mixture, and the remaining solid material was recrystallized from 50 c.c. of ethanol to obtain 7.7 g of the desired product. Melting point: 204-205℃. (3)4-(trans-4-propylcyclohexyl)
4-(2,3-dicyanopyrazinyl-benzoate)
5) Production of phenyl ester 4-(trans-4-propylcyclohexyl)
2 g of thionyl chloride was added to 1 g of benzoic acid, and the mixture was reacted under reflux for 2 hours. After the reaction was completed, excess thionyl chloride was distilled off to obtain acid chloride. On the other hand, the acid chloride obtained earlier was added to a solution of 1 g of 4-(2,3-dicyanopyrazinyl-5)phenol obtained in (2) dissolved in 3 c.c. of dry pyridine, and the mixture was heated at 60°C. The mixture was heated and reacted for 3 hours. After the reaction is complete, remove the reactant with water.
It was poured into 100 c.c. and the precipitated crystals were extracted with toluene (10 c.c.). The extract was washed with dilute hydrochloric acid, dilute aqueous sodium hydroxide solution, and then water, and the toluene layer was dried over anhydrous sodium sulfate. Subsequently, toluene was distilled off and the remaining solid material was recrystallized from 5 c.c. of benzene to obtain 1.1 g of the desired product. C-N point; 164.8~
165.3℃, N-I point; 273.0℃. Examples 2 to 4 The following compounds were synthesized by a method similar to Example 1. 4-Butylbenzoic acid 4-(2,3-dicyanopyrazinyl-5) phenyl ester C-I; 122.5-123.0°C 4-pentyloxybenzoic acid 4-(2,3-dicyanopyrazinyl-5) Phenyl ester C-I; 126.4-127.2℃ N-I; 123.5-123.8℃ trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid 4-(2,
3-Dicyanopyrazinyl-5) Phenyl ester C-N: 165.7-166.9°C N-I: 277.8-278.1°C Examples 5-9 The following five compounds were synthesized by a method similar to Example 1. . Butyl-4-(2,3-dicyanopyrazinyl-5)
phenyl carbonate. Pentanoic acid 4-(2,3
-dicyanopyrazinyl-5) phenyl ester. Trans-4-propylcyclohexanecarboxylic acid 4-(2,3-dicyanopyrazinyl-5) phenyl ester. Trans-4-(4-butylphenyl)cyclohexanecarboxylic acid 4-(2,3-dicyanopyrazinyl-5) phenyl ester. 4-(4-pentylphenyl)benzoic acid 4-
(2,3-dicyanopyrazinyl-5) phenyl ester. The phase transition points of these compounds are shown in Table 1 along with the results of Examples 1 to 4.
【表】
第１表中、相転移点の欄のＣ，Ｎ，Ｉはそれぞ
れ結晶、ネマチツク液晶および等方性液体の各相
を示し、下欄の・印は上記の相の存在することを
示す。また、（）はモノトロビツク転移点を示す。
応用例[Table] In Table 1, C, N, and I in the phase transition point column indicate the crystal, nematic liquid crystal, and isotropic liquid phases, respectively, and the mark in the bottom column indicates the presence of the above phases. show. In addition, () indicates the monotrovik transition point. Application example
【式】30重量部[Formula] 30 parts by weight
【式】40重量部[Formula] 40 parts by weight
【式】30重量部
なる割合の液晶組成物のネマチツク温度範囲は−
５〜52℃である。この液晶組成物をセル厚10μm
のTNセルに封入したものの動作しきい電圧は
1.54V、飽和電圧は2.13Vであつた。また粘度は
20℃で23.5cPであつた。上記の液晶組成物95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−（トランス−４−プロピルシクロヘキシ
ル）安息香酸４−（２，３−ジシアノピラジニル
−５）フエニルエステル５重量部を加えた液晶組
成物のネマチツク液晶温度範囲は−５℃〜59℃で
あつた。これを前述と同じセル厚10μmのTNセ
ルに封入した物の動作しきい電圧は1.20V、飽和
電圧は1.82Vと大幅に改善された。また粘度は20
℃で25cPであつた。[Formula] The nematic temperature range of a liquid crystal composition of 30 parts by weight is -
The temperature is 5-52°C. This liquid crystal composition has a cell thickness of 10 μm.
The operating threshold voltage of the TN cell sealed in is
The voltage was 1.54V, and the saturation voltage was 2.13V. Also, the viscosity is
It was 23.5cP at 20℃. 4-(2,3-dicyanopyrazinyl-5) 4-(trans-4-propylcyclohexyl)benzoate shown in Example 1, which is one of the compounds of the present invention, was added to 95 parts by weight of the above liquid crystal composition. ) The nematic liquid crystal temperature range of the liquid crystal composition containing 5 parts by weight of phenyl ester was -5°C to 59°C. When this was sealed in a TN cell with the same cell thickness of 10 μm as described above, the operating threshold voltage was 1.20V, and the saturation voltage was significantly improved to 1.82V. Also, the viscosity is 20
It was 25cP at ℃.
Claims (1)
アルコキシ基を表わし、Ｘは−０−、−CH2−、
【式】【式】 【式】 【式】 【式】または 【式】を表わす） で示される２，３−ジシアノ−５−置換ピラジン
誘導体。 ２ 一般式 （式中、Ｒは炭素数１〜９のアルキル基または
アルコキシ基を表わし、Ｘは−０−、−CH2−、
【式】【式】 【式】 【式】 【式】または 【式】を表わす） で示される２，３−ジシアノ−５−置換ピラジン
誘導体を含有することを特徴とする液晶組成物。[Claims] 1. General formula (In the formula, R represents an alkyl group or an alkoxy group having 1 to 9 carbon atoms, and X is -0-, -CH 2 -,
A 2,3-dicyano-5-substituted pyrazine derivative represented by [Formula] [Formula] [Formula] [Formula] [Formula] or [Formula]. 2 General formula (In the formula, R represents an alkyl group or an alkoxy group having 1 to 9 carbon atoms, and X is -0-, -CH 2 -,
A liquid crystal composition characterized by containing a 2,3-dicyano-5-substituted pyrazine derivative represented by the formula: [Formula] [Formula] [Formula] or [Formula].
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19383983A JPS6084273A (en) | 1983-10-17 | 1983-10-17 | 2,3-dicyano-5-substituted pyrazine derivative |
| DE8484109430T DE3481055D1 (en) | 1983-08-22 | 1984-08-08 | 2,3-DICYAN-5-SUBSTITUTED PYRAZINE AND LIQUID CRYSTAL COMPOSITION CONTAINING THEM. |
| EP84109430A EP0136480B1 (en) | 1983-08-22 | 1984-08-08 | 2,3-dicyano-5-substituted pyrazines and liquid crystal composition containing them |
| US06/641,730 US4592857A (en) | 1983-08-22 | 1984-08-17 | 2,3-dicyano-5-substituted pyrazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19383983A JPS6084273A (en) | 1983-10-17 | 1983-10-17 | 2,3-dicyano-5-substituted pyrazine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6084273A JPS6084273A (en) | 1985-05-13 |
| JPH0452269B2 true JPH0452269B2 (en) | 1992-08-21 |
Family
ID=16314592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19383983A Granted JPS6084273A (en) | 1983-08-22 | 1983-10-17 | 2,3-dicyano-5-substituted pyrazine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6084273A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2554191Y2 (en) * | 1991-05-16 | 1997-11-12 | 三菱農機株式会社 | Recoil starter for mobile farm equipment |
| CN111995589B (en) | 2015-11-10 | 2023-12-05 | 国立大学法人九州大学 | Method for producing 2,5-dicyano-3,6-dihalopyrazine |
-
1983
- 1983-10-17 JP JP19383983A patent/JPS6084273A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6084273A (en) | 1985-05-13 |
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