JPS61233672A - Pyeridine derivative exhibiting positive dielectric anisotropy - Google Patents
Pyeridine derivative exhibiting positive dielectric anisotropyInfo
- Publication number
- JPS61233672A JPS61233672A JP60074075A JP7407585A JPS61233672A JP S61233672 A JPS61233672 A JP S61233672A JP 60074075 A JP60074075 A JP 60074075A JP 7407585 A JP7407585 A JP 7407585A JP S61233672 A JPS61233672 A JP S61233672A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- formulas
- tables
- 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.)
- Pending
Links
- 230000001747 exhibiting effect Effects 0.000 title 1
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000003222 pyridines Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 abstract description 29
- -1 trans-4-substituted cyclohexyl methyl ketone Chemical class 0.000 abstract description 13
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 8
- 150000008062 acetophenones Chemical class 0.000 abstract description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 4
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- PKQIDSVLSKFZQC-UHFFFAOYSA-N 3-oxobutanal Chemical class CC(=O)CC=O PKQIDSVLSKFZQC-UHFFFAOYSA-N 0.000 abstract description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 235000019253 formic acid Nutrition 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal 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
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical class CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-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
- AULWPXHFRBLPAE-UHFFFAOYSA-N 6-chloropyridine Chemical compound ClC1=C=CC=C[N]1 AULWPXHFRBLPAE-UHFFFAOYSA-N 0.000 description 1
- PGZHSVWXFKKCNR-UHFFFAOYSA-N 6-chloropyridine-2-carbonitrile Chemical compound ClC1=CC=CC(C#N)=N1 PGZHSVWXFKKCNR-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 210000004460 N cell Anatomy 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- NODGRWCMFMEGJH-UHFFFAOYSA-N p-ethylacetophenone Chemical compound CCC1=CC=C(C(C)=O)C=C1 NODGRWCMFMEGJH-UHFFFAOYSA-N 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は液晶組成物に添加することにより該組成物の正
の誘電異方性を大きくすることのできる新規な化合物お
よびこの化合物を含有する液晶組成物に関する。Detailed Description of the Invention [Technical Field] The present invention relates to a novel compound that can increase the positive dielectric anisotropy of a liquid crystal composition by adding it to the composition, and a liquid crystal composition containing this compound. Regarding.
液晶物質の電気光学効果を利用した液晶表示素子にはね
じれネマチック（ＴＮ）型、ゲストホスト（ＧＨ）型、
複屈折率制御（ＥＣＢ）型、動的散乱（ＤＳ ）型等の
各種の方式があシ、液晶物質に望まれる性質もそれぞれ
の方式によって異る。いずれの方式であっても、できる
だけ広い温度範囲で液晶相を示し、水分、熱、光、空気
などに対して安定であることが必要である。Liquid crystal display elements that utilize the electro-optic effect of liquid crystal materials include twisted nematic (TN) type, guest host (GH) type,
Various methods are available, such as a controlled birefringence (ECB) type and a dynamic scattering (DS) type, and the desired properties of the liquid crystal material also differ depending on each method. Regardless of the method, it is necessary to exhibit a liquid crystal phase over a wide temperature range as possible and to be stable against moisture, heat, light, air, etc.
現在のところ単一化合物でこの様な条件をすべて満たす
ものはなく、数種の液晶化合物や非液晶化合物を混合し
た液晶組成物が実用に供されている。At present, there is no single compound that satisfies all of these conditions, and liquid crystal compositions that are a mixture of several types of liquid crystal compounds and non-liquid crystal compounds are in practical use.
近年、よシ広い温度範囲で、かつ、より低い駆動電圧で
作動する液晶表示素子への要求がますます強くなシ、シ
きい電圧ならびに飽和電圧のよ如低い液晶組成物が要望
されている。In recent years, there has been an increasingly strong demand for liquid crystal display elements that operate over a wider temperature range and at lower driving voltages, and liquid crystal compositions with lower threshold voltages and saturation voltages are required.
誘電異方性（以下△εと略記する）のよシ大きな液晶組
成物を調製する方法として液晶組成物にその液晶組成物
との相溶性がよく、かつ、△εの大きな化合物を添加す
る方法がある。本発明は△εが正で大きく、かつ他の液
晶化合物と相溶性が良く、この化合物を含有する液晶組
成物を用いた液晶表示素子の駆動電圧を低下させること
のできるような新規な化合物を提供することにあシ、更
にはその化合物を含有する液晶組成物を提供するにある
。A method for preparing a liquid crystal composition with a large dielectric anisotropy (hereinafter abbreviated as △ε) is to add to the liquid crystal composition a compound that has good compatibility with the liquid crystal composition and has a large △ε. There is. The present invention provides a novel compound that has a positive and large Δε, has good compatibility with other liquid crystal compounds, and can reduce the driving voltage of a liquid crystal display element using a liquid crystal composition containing this compound. Another object of the present invention is to provide a liquid crystal composition containing the compound.
本発明は一般式
（式中Ｒは炭素数１〜１５のアルキル基またはアルコキ
シル基を示し、ＸはＸ＞、−Ｃ−イコＢＣＸを示し、Ｙ
はＦまたはＣ４を示す）で表されるピリジン誘導体、お
よびとのピリジン誘導体の少くとも１種を含有する液晶
組成物である。The present invention is based on the general formula (wherein R represents an alkyl group or an alkoxyl group having 1 to 15 carbon atoms, X represents X>, -C-icoBCX, and Y
represents F or C4), and at least one type of pyridine derivatives.
本発明のピリジン誘導体は以下の方法によって製造する
ことができる。すなわち、トランス−４−［ｍシクロヘ
キシルメチルケトン（１）または４−置換アセトフェノ
ン（１）とギ酸エステルとから得られるホルミルアセト
ン誘導体のナトリウムエルレート（ＩＩ）は、シアノア
セトアミドと水溶液中で縮合して３−シアノ−６−置換
−２（１）ピリドン（ＩＩＩ）を与える。これをオキシ
塩化リンと処理すれば２−置換−５−シアノ−６−クロ
ロピリジン（ＩＶ）が得られ、さらにフッ化カリウムを
用いたハロゲン交換反応によって２−＠ｐ−５−シアノ
−６−フルオロピリジン（Ｖ）が得られる。The pyridine derivative of the present invention can be produced by the following method. That is, sodium erulate (II), a formylacetone derivative obtained from trans-4-[m-cyclohexylmethylketone (1) or 4-substituted acetophenone (1) and formic acid ester, is condensed with cyanoacetamide in an aqueous solution. Provides 3-cyano-6-substituted-2(1)pyridone (III). Treatment of this with phosphorus oxychloride yields 2-substituted-5-cyano-6-chloropyridine (IV), which is further subjected to a halogen exchange reaction using potassium fluoride to yield 2-@p-5-cyano-6- Fluoropyridine (V) is obtained.
これを反応式で示すと次のようになる。This reaction formula is shown as follows.
（ＩＩ）
（Ｖｌ
式Ｖ）あるいは（Ｖ）で示される本発明の化合物祉その
１種または２種以上を１種または２種以上の他の液晶化
合物と混合して液晶組成物として使用することができる
。そのような他の液晶化合物としては、シッフ塩基系液
晶化合物、アゾキシ系液晶化合物、安息香酸エステル系
液晶化合物、シクロへキシルカルボン酸エステル系液晶
化合物、ビフェニル系液晶化合物、フェニルシクロヘキ
ザン系液晶化合物、フェニルピリミジン系液晶化合物等
を例示できる。(II) Mixing one or more of the compounds of the present invention represented by formula V or (V) with one or more other liquid crystal compounds for use as a liquid crystal composition. I can do it. Such other liquid crystal compounds include Schiff base liquid crystal compounds, azoxy liquid crystal compounds, benzoic acid ester liquid crystal compounds, cyclohexylcarboxylic acid ester liquid crystal compounds, biphenyl liquid crystal compounds, phenylcyclohexane liquid crystal compounds, Examples include phenylpyrimidine liquid crystal compounds.
本発明のピリジン誘導体は他の液晶化合物または液晶組
成物との相溶性に優れ、かつ大きな正の誘電異方性を有
するので、これを液晶組成物に添加することによシその
組成物の△εを正の側に大きくすることができ、ひいて
は液晶表示素子の駆動電圧を低下させることができる。The pyridine derivative of the present invention has excellent compatibility with other liquid crystal compounds or liquid crystal compositions, and has large positive dielectric anisotropy. It is possible to increase ε to the positive side, and as a result, it is possible to reduce the driving voltage of the liquid crystal display element.
以下に実施例によって本発明を具体的に説明するが本発
明はこれらの例に限定されるものではない。The present invention will be specifically explained below with reference to Examples, but the present invention is not limited to these Examples.
実施例１
２− （４’−エチルフェニル）−５−シアノ−６−ク
ロロピリジンの製造
ナトリウムメトキサイド１６．２Ｆをトルエン３００Ｉ
＋Ｉ／に懸濁させ０℃以下に保っておく。この溶液に４
−エチルアセトフェノン４４．４１’およびギ酸エチル
２２．２ ｔの混合液を反応温度を５℃以下に保ちなが
ら滴下し、引き続き室温で８時間反応させた。反応液に
水３００ｍを加え反応物を抽出し、分取しＡにシアノア
セトアミド２５．２ ｆおよび酢酸ピペリジン８１を加
えて５時間加熱還流した。冷却後、反応液が酸性になる
まで酢酸を加え、生じた沈澱を濾過、乾燥１４：３−シ
アノ−６−（４’−エチルフェニル）−２（１）−ピリ
ドン３０２を得た。この化合物にオキシ塩化リン１２０
ｍを加え１００℃で８時間加熱反応させた後オキシ塩化
リンを留去し、得られた残留物を温水１５３ｉｌに加え
、次いで溶液がアルカリ性になるまで２Ｎ−水酸化ナト
リウム溶液を添加した。この溶液にトルエン３００ｄを
加えて生成物を抽出し、分取したトルエン層を洗浄水が
中性になるまで水洗した。Example 1 Production of 2-(4'-ethylphenyl)-5-cyano-6-chloropyridine Sodium methoxide 16.2F was mixed with toluene 300I
+I/ and kept below 0°C. Add 4 to this solution
A mixed solution of 44.41' of -ethylacetophenone and 22.2 t of ethyl formate was added dropwise while keeping the reaction temperature below 5° C., and the mixture was then reacted at room temperature for 8 hours. 300 mL of water was added to the reaction solution to extract the reaction product, and 25.2 f of cyanoacetamide and 81 g of piperidine acetate were added to fraction A, and the mixture was heated under reflux for 5 hours. After cooling, acetic acid was added until the reaction solution became acidic, and the resulting precipitate was filtered to obtain dried 14:3-cyano-6-(4'-ethylphenyl)-2(1)-pyridone 302. This compound contains phosphorus oxychloride 120
After adding m and reacting by heating at 100°C for 8 hours, phosphorus oxychloride was distilled off, and the obtained residue was added to 153 il of warm water, and then 2N sodium hydroxide solution was added until the solution became alkaline. To this solution, 300 d of toluene was added to extract the product, and the separated toluene layer was washed with water until the washing water became neutral.
このトルエン層からトルエンを留去し、残留物をエタノ
ールを用いて再結晶させて目的物の２−（４′−エチル
フェニル）−５−シアノ−６＝クロロピリジン２Ｃ１’
を得た。このものの融点は１０４．６〜１０５．６℃で
あった。Toluene was distilled off from this toluene layer, and the residue was recrystallized using ethanol to obtain the target product, 2-(4'-ethylphenyl)-5-cyano-6=chloropyridine 2C1'.
I got it. The melting point of this product was 104.6-105.6°C.
実施例２〜９
実施例１における４−エチルアセトフェノンに代えて各
種の４−１１換アセトフエノンあるいハトランス−４−
ｆ換シクロヘキシルメチルケトンを用い、実施例１と同
様の操作を施して各種のピリジン誘導体を合成した。Examples 2 to 9 In place of 4-ethylacetophenone in Example 1, various 4-11-substituted acetophenones or hatrans-4-
Various pyridine derivatives were synthesized using f-substituted cyclohexylmethylketone in the same manner as in Example 1.
美施例２
２−（４’ −ｎ−プロピルフェニル）−５−シアノ−
６−クロロピリジン融点８２．５〜８３．４℃実施例３
２−（４’−ｎ−ブチルフェニル）−５−シアノ−６−
クロロピリジン 融点１０５．９〜１０６．７℃実施例
４
２−（４’−ｎ−ペンチルオキシフェニル）−５−シア
ノ−６−クロロピリジン
融点 ７６．４〜７６．８℃
実施例５
２− （トランス−４’ −ｎ −フロビルシクロヘキ
シル）−５−シアノ−６−クロロピリジン融点 ２８．
７〜２９．５℃
実施例６
２−（）ランス−４′−ｎ−ペンチルシクロヘキシル）
−５−シアノ−６−クロロピリジン融点 ７０．３〜７
１．３℃
実施例７
２−（トランス−４′−ｎ−へプロルシクロヘキシル）
−５−シアノ−６−クロロピリジン融点 ４５．６〜４
６．３℃
実施例日
２−（４’−（）ランス−４１−ｎ−プロピルシクロヘ
キシル〕フェニル）−５−シア／−６−クロロピリジン
結晶−ネ−ｑ ｆ ツク点： １０８．４〜１０９．４
℃、ネマチック−透明点： １２０．５〜１２０．’７
℃７℃実施
２−（トランス−４’−（）ランス−４’−ｎ−プロピ
ルシクロヘキシル）シクロヘキシル）−５−シアノ−６
−クロロピリジン
結晶−ネマチック点： １０４．５〜１０５．３℃、ネ
マチック−透明点：１２４．’７〜１２４．８℃実施例
１０
２−（４’−エチルフェニル）−５−シアノ−６−フル
オロピリジンの製造
実施例１で得られた２−（４’−エテルフェニル）−５
−シアノ−６−クロロピリジン１０ｆ、フッ化カリウム
８２およびジメチルスルホキシド１００−の混合液を２
０時間加熱還流した。Beautiful Example 2 2-(4'-n-propylphenyl)-5-cyano-
6-chloropyridine Melting point 82.5-83.4°C Example 3 2-(4'-n-butylphenyl)-5-cyano-6-
Chloropyridine Melting point: 105.9-106.7°C Example 4 2-(4'-n-pentyloxyphenyl)-5-cyano-6-chloropyridine Melting point: 76.4-76.8°C Example 5 2-( Trans-4'-n-furobylcyclohexyl)-5-cyano-6-chloropyridine Melting point 28.
7-29.5°C Example 6 2-() lance-4'-n-pentylcyclohexyl)
-5-cyano-6-chloropyridine Melting point 70.3-7
1.3°C Example 7 2-(trans-4'-n-heprolcyclohexyl)
-5-cyano-6-chloropyridine Melting point 45.6-4
6.3°C Example day 2-(4'-() lance-41-n-propylcyclohexyl]phenyl)-5-cya/-6-chloropyridine crystal N-qf Point: 108.4-109 .4
°C, nematic clearing point: 120.5-120. '7
Conducted at 7°C 2-(trans-4'-()trans-4'-n-propylcyclohexyl)cyclohexyl)-5-cyano-6
- Chloropyridine crystal - Nematic point: 104.5-105.3°C, Nematic clearing point: 124. '7-124.8℃ Example 10 Production of 2-(4'-ethylphenyl)-5-cyano-6-fluoropyridine 2-(4'-ethylphenyl)-5 obtained in Example 1
- A mixture of 10f of cyano-6-chloropyridine, 82% of potassium fluoride and 100% of dimethyl sulfoxide was added to the
The mixture was heated under reflux for 0 hours.
冷却後、水２００ｍ／およびトルエン１００ｍ／を加え
て抽出し、トルエン層を分取し洗浄水が中性になるまで
水洗した後、トルエンを留去し、残留物をエタノールを
用いて再結晶させて目的の２− （４’−エチルフェニ
ル）−５−シアノ−６−フルオロピリジンを得た。After cooling, extract by adding 200 m/m of water and 100 m/m of toluene, separate the toluene layer and wash with water until the washing water becomes neutral, then distill off the toluene and recrystallize the residue using ethanol. The desired 2-(4'-ethylphenyl)-5-cyano-6-fluoropyridine was obtained.
実施例１１（応用例）
なる液晶組成物（Ａ）のネマチック−透明点は５２．１
℃、△εは＋１１．２、光学異方性値（以下△ｎと略記
する。）は０．１１９である。これを対向透明電極を有
するセル厚１ｏμｍのＴＮセルに封入した液晶セルの２
０Ｃにおけるしきい値電圧は１．５４ Ｖ 、飽和電圧
は２．１３ Ｖであった。この液晶組成物（Ａ） ９０
重量％に実施例１で製造シた２ −（４’−エチルフェ
ニル）−５−シアノ−６−クロロピリジン１０重量％を
加えた液晶組成物（Ｂ）のネマチック−透明点は４０．
７℃、△εは＋１２．７、△ｎは０．０４９、前述のＴ
Ｎセルに封入したものの２０℃におけるしきい値電圧は
１．２２Ｖ、飽和電圧は１．７１Ｖであった。Example 11 (Application example) The nematic clearing point of the liquid crystal composition (A) is 52.1
°C, Δε is +11.2, and the optical anisotropy value (hereinafter abbreviated as Δn) is 0.119. This was sealed in a TN cell with a cell thickness of 1 μm and having opposing transparent electrodes.
The threshold voltage at 0 C was 1.54 V, and the saturation voltage was 2.13 V. This liquid crystal composition (A) 90
The nematic clearing point of the liquid crystal composition (B) in which 10% by weight of 2-(4'-ethylphenyl)-5-cyano-6-chloropyridine prepared in Example 1 was added to the weight% was 40.
7℃, △ε is +12.7, △n is 0.049, T as mentioned above
When sealed in an N cell, the threshold voltage at 20° C. was 1.22V, and the saturation voltage was 1.71V.
実施例１２（応用例）
実施例１１の液晶組成物（Ａ） ８５重量％に実施例日
で製造した２−（４’−（）ランス−４′−プロピルシ
クロヘキシル）フェニル）−５−シアノ−６−クロロピ
リジン１５重量％を加えた液晶組成物（Ｃ）のネマチッ
ク−透明点は５８．０℃、△εは＋１２．３、△ｎは０
．１７９、前述のＴＮセルに封入したものの２０℃にお
けるしきい値電圧は１，５８Ｖ、飽和電圧は２．２］−
Ｖであった。Example 12 (Application example) Liquid crystal composition (A) of Example 11 85% by weight of 2-(4'-()lans-4'-propylcyclohexyl)phenyl)-5-cyano- produced on the day of the example The nematic clearing point of the liquid crystal composition (C) containing 15% by weight of 6-chloropyridine is 58.0°C, Δε is +12.3, and Δn is 0.
．． 179, the threshold voltage at 20°C of the above-mentioned TN cell sealed is 1.58 V and the saturation voltage is 2.2]-
It was V.
以上that's all
Claims (2)
シ基を示し、Ｘは▲数式、化学式、表等があります▼、
▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼または ▲数式、化学式、表等があります▼を示し、ＹはＦまた
はＣｌを示す） で表されるピリジン誘導体。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents an alkyl group or alkoxy group having 1 to 15 carbon atoms, and X is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Mathematical formulas, chemical formulas, tables, etc. are available ▼, and Y represents F or Cl).
シ基を示し、Ｘは▲数式、化学式、表等があります▼、
▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼または ▲数式、化学式、表等があります▼を示し、ＹはＦまた
はＣｌを示す） で表されるピリジン誘導体の少くとも１種を含有する液
晶組成物。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents an alkyl group or alkoxy group having 1 to 15 carbon atoms, and X is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and Y represents F or Cl) A liquid crystal composition containing at least one type of pyridine derivative represented by .
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60074075A JPS61233672A (en) | 1985-04-08 | 1985-04-08 | Pyeridine derivative exhibiting positive dielectric anisotropy |
| US06/833,717 US4684477A (en) | 1985-03-06 | 1986-02-27 | Pyridine derivatives and their use in liquid crystals |
| EP86301614A EP0194153B1 (en) | 1985-03-06 | 1986-03-06 | Pyridine derivatives |
| DE8686301614T DE3675232D1 (en) | 1985-03-06 | 1986-03-06 | PYRIDE DERIVATIVES. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60074075A JPS61233672A (en) | 1985-04-08 | 1985-04-08 | Pyeridine derivative exhibiting positive dielectric anisotropy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61233672A true JPS61233672A (en) | 1986-10-17 |
Family
ID=13536690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60074075A Pending JPS61233672A (en) | 1985-03-06 | 1985-04-08 | Pyeridine derivative exhibiting positive dielectric anisotropy |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61233672A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006523184A (en) * | 2003-02-22 | 2006-10-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Cyanopyridone derivatives as liquid crystals |
-
1985
- 1985-04-08 JP JP60074075A patent/JPS61233672A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006523184A (en) * | 2003-02-22 | 2006-10-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Cyanopyridone derivatives as liquid crystals |
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