JPS6383069A - 2-(3-fluoro-4-cyanophenyl)pyridine derivative - Google Patents
2-(3-fluoro-4-cyanophenyl)pyridine derivativeInfo
- Publication number
- JPS6383069A JPS6383069A JP22656486A JP22656486A JPS6383069A JP S6383069 A JPS6383069 A JP S6383069A JP 22656486 A JP22656486 A JP 22656486A JP 22656486 A JP22656486 A JP 22656486A JP S6383069 A JPS6383069 A JP S6383069A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- compound
- expressed
- fluoro
- 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
- NVHJLYVINACKFB-UHFFFAOYSA-N 2-fluoro-4-pyridin-2-ylbenzonitrile Chemical class C1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1 NVHJLYVINACKFB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005695 Ammonium acetate Substances 0.000 abstract description 3
- 235000019257 ammonium acetate Nutrition 0.000 abstract description 3
- 229940043376 ammonium acetate Drugs 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 150000002081 enamines Chemical class 0.000 abstract description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- -1 3-fluoro-4-bromphenyl ketone Chemical compound 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-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
- 238000001816 cooling Methods 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ZKTFZNPTAJIXMK-UHFFFAOYSA-N 2-cyclohexylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1CCCCC1 ZKTFZNPTAJIXMK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- 239000013078 crystal Substances 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical class C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発８ＡＦｉ電気光学的嚢示材料として有用な２−（３
′−フルオロ−４′−シアノフェニル）ピリジン誘導体
に関する。Detailed Description of the Invention [Industrial Application Field] 2-(3
'-Fluoro-4'-cyanophenyl)pyridine derivatives.
液晶表示セルの代表的なものにエム・シャット（Ｍ−８
＊ｈａｄｔ ）等（ＡＰＰＬＩＥＤ ＰＨＹＳＩＣ８Ｌ
ＥＴＴＥＲ８１８。M-Shut (M-8) is a typical liquid crystal display cell.
*hadt) etc. (APPLIED PHYSIC8L
ETTER818.
１２７〜１２８（１９７１））によって提案された電界
効果型セル（フィールド・エフェクト・モード・セル）
又はジー・エイチ・バイルマイヤー（Ｇ−ＨＨｅｉｌｍ
ｅｉｅｒ ）等（ＰＲＯＣＥＥＤＩＮＧ ＯＦ ＴＨＥ
１．Ｅ、Ｅ、Ｅ。127-128 (1971))
or G-H Heilm
eier ) etc. (PROCEEDING OF THE
1. E, E, E.
ツタリング・モード・セル）又はノー・エイチ・バイル
マイヤー（Ｇ−ＨＨｓｉ１ｍ＠ｉｓｒ ）等（ＡＰＰＬ
ＩＥＤＰＨＹＳＩＣ８ＬＥＴＴｇａｓ １３ 、９１
（１９６８））あるいはディー・エル・ホワイト（ＤＬ
Ｗｈｉｔ・）等（ＪＯＵＲＮＡＬ ＯＦ ＡＰＰＬＩＥ
Ｄ ＰＨＹＳＩＣ８４５、４７１８（１９７４））によ
って提案されたダスト・ホスト型セルなどがある。Tuttering Mode Cell) or No. H. Beilmeier (G-HHsi1m@isr) etc. (APPL
IEDPHYSIC8LETTgas 13, 91
(1968)) or D. L. White (DL
Whit・) etc. (JOURNAL OF APPLIE
There is a dust host type cell proposed by D PHYSIC 845, 4718 (1974).
これらの液晶表示セルには種々の特性が要求されている
が、低いしきい値電圧（Ｖｔｈ）は特に重要な要求特性
であり、低いしきい値電圧を有する液晶表示セルは低電
圧駆動が可能となる。These liquid crystal display cells are required to have various characteristics, but low threshold voltage (Vth) is a particularly important required characteristic, and liquid crystal display cells with low threshold voltage can be driven at low voltages. becomes.
このような目的で現在使用されている優れた液晶化合物
として発明者らが開発した
特開昭５８−８３６６５の
特開昭５９−８０６５１の
が知られている。JP-A-58-83665 and JP-A-59-80651, which were developed by the inventors, are known as excellent liquid crystal compounds currently used for such purposes.
しかし、上記の化合物は、母体液晶に添加した場合、母
体液晶のしきい値電圧を低下させる効果が充分衣われる
ものの、母体液晶の粘度を上昇させる傾向がある。母体
額晶の粘度の上昇は、液晶表示セルの応答速度を遅くし
てしまう。今日の技術水準の高度化によって、低電圧駆
動にすぐれ、よシ高速応答性にすぐれた液晶組成物が所
望されるようになっている。However, when the above-mentioned compound is added to the matrix liquid crystal, although it has a sufficient effect of lowering the threshold voltage of the matrix liquid crystal, it tends to increase the viscosity of the matrix liquid crystal. An increase in the viscosity of the parent forehead crystal slows down the response speed of the liquid crystal display cell. With the increasing sophistication of today's technology, there is a demand for liquid crystal compositions that are excellent in low-voltage driving and have excellent high-speed response.
本発明の目的はしきい値電圧を効果的に低下せしめ、尚
かつ、粘度の上昇を小幅に抑える化合物の提供にめる。An object of the present invention is to provide a compound that effectively lowers the threshold voltage and also suppresses the increase in viscosity to a small extent.
本発明は、 一般式 で餞わされる化合物を提供するものである。 The present invention general formula The present invention provides a compound that is coated with
本発明の式（１）の化合物は、次の製造方法に従りて製
造することができる。The compound of formula (1) of the present invention can be produced according to the following production method.
意味をもち、式（ＩＩＩ）におけるＸはハロダン原子を
意味する。X in formula (III) means a halodane atom.
第１段階
式（ＩＩ）のエナミンをエーテル等の溶液中でトリエチ
ルアミンの如き塩基の存在下で式Ｃｍ）のハロビニル−
３−フルオロ−４−ブロムフェニルケトンと反応させた
彼、酸と反応させて式（ＩＶ）の化合物を製造する。The first step is to convert the enamine of formula (II) into a halobinyl compound of formula Cm) in a solution such as ether in the presence of a base such as triethylamine.
The compound of formula (IV) is prepared by reacting with 3-fluoro-4-bromphenyl ketone and acid.
第２段階
式（■）の化合物に酢酸等の溶媒中で酢酸アンモニウム
を反応させて式（Ｖ）の化合物を製造する。In the second step, the compound of formula (■) is reacted with ammonium acetate in a solvent such as acetic acid to produce a compound of formula (V).
第３段階
式（Ｙ）の化合物にＮ、Ｎ−ジメチルホルムアミド等の
溶媒中でシアン化第−銅を反応させて式（１）の化合物
を製造する。Third step: A compound of formula (Y) is reacted with cupric cyanide in a solvent such as N,N-dimethylformamide to produce a compound of formula (1).
斯くして製造される式（１）の化合物の代表的なものの
転移温度を第１表に掲げる。Table 1 lists the transition temperatures of representative compounds of formula (1) thus produced.
第１表
１ ｎ−Ｃ３Ｈ１１−０−２５（Ｃ−ｅＩン １
ｏ（Ｉ；：Ｎ）３ ｎ−０５Ｈ７−１（防９６（Ｃ−＋
Ｎ）１９３（Ｎａｔ）本発明に係る式ＣＩ）の化合物は
、正の誘電率異方性を有するネマチック液晶化合物であ
υ、従って、例えば、正又は負の誘電率異方性を有する
他のネマチック液晶化合物との混合物の状態で電界効果
製表示セルの材料として使用することができる。Table 1 1 n-C3H11-0-25 (C-elin 1
o(I;:N)3 n-05H7-1 (Defense 96 (C-+
N) 193 (Nat) The compound of formula CI) according to the invention is a nematic liquid crystal compound with positive dielectric anisotropy υ, and therefore can be used, for example, with other compounds with positive or negative dielectric anisotropy. It can be used as a material for field effect display cells in a mixture with nematic liquid crystal compounds.
このように、式（１）の化合物と混合して使用すること
のできる好ましい代茨例としては、例えば４−置換安息
香酸４′−置換フェニルエステル、４−置換シクロヘキ
サンカルゲン酸４’−［換フェニルエステル、４−ｆｌ
換シクロヘキサンカルデン酸４’ｌｔ換ビフェニルエス
テル、４−（４−ｆｌ換シクロヘキサンカルゲニルオキ
シ）安息香酸４′−置換フェニルエステル、４−（４−
ｆｌ置換シクロヘキシル 安息香酸４’ −ｅ換フェニ
ルエステル、４−（４−置換シクロヘキシル）安息香酸
４′−置換シクロヘキシルエステル、４−ｗｔ換４’−
［換ピ７工二／Ｉ／、 ４−Ｗｔ換４’−Ｒ換フェニル
シクロヘキサン、４−置換４′−置換ターフェニル、４
−ｔｌ換４′−ビフェニルシクロヘキサン、２ （４’
−［換フェニル）−５−置換ビリミジンなどを挙げるこ
とができる。As described above, examples of preferable substitutes that can be used in combination with the compound of formula (1) include 4-substituted benzoic acid 4'-substituted phenyl ester, 4-substituted cyclohexane cargenic acid 4'-[substituted Phenyl ester, 4-fl
4'-lt substituted biphenyl ester of substituted cyclohexane caldenic acid, 4-(4-fl substituted cyclohexane calgenyloxy)benzoic acid 4'-substituted phenyl ester, 4-(4-
fl substituted cyclohexyl benzoic acid 4'-e substituted phenyl ester, 4-(4-substituted cyclohexyl)benzoic acid 4'-substituted cyclohexyl ester, 4-wt substituted 4'-
[Converted 7-di/I/, 4-Wt-substituted 4'-R-substituted phenylcyclohexane, 4-substituted 4'-substituted terphenyl, 4
-tl-converted 4'-biphenylcyclohexane, 2 (4'
Examples include -[substituted phenyl)-5-substituted pyrimidine.
第２表は時分割駆動特性の優れたネマチック液晶材料と
して現在汎用されている母体液晶（Ａ）の９０重量％と
第１表に示した式（１）の化合物＆ｌ、ム２．４３の各
々の１０重量−とから成る各混合液晶について測定され
たしきい値電圧ｖｔｈと２０℃の粘度を掲示し、比較の
丸めに母体液晶（Ａ）自体並びに母体液晶（Ａ）の９０
重１１ｔｑｂと扁１．４２、Ａ３とそれぞれ類似化学構
造をもち、しきい値電圧を低下させる目的で使用されて
いる化合物（ａ）、化合物（ｂ）、化合物（、）の各々
の１０重量％とから成る各混合液晶について測定された
しきい値電圧と２０℃の粘度を掲示した。Table 2 shows 90% by weight of the base liquid crystal (A), which is currently widely used as a nematic liquid crystal material with excellent time-division driving characteristics, and each of the compounds &l and mu2.43 of the formula (1) shown in Table 1. The threshold voltage vth and viscosity at 20°C measured for each mixed liquid crystal consisting of 10% by weight of
10% by weight of each of compound (a), compound (b), and compound (,), which have a similar chemical structure to 11 tqb, 1.42 tqb, and A3, and are used for the purpose of lowering the threshold voltage. The threshold voltage and viscosity at 20° C. measured for each mixed liquid crystal consisting of the following are listed.
尚、母体液晶（Ａ）は
８重量−の
８重ｆ％の
８重量％の
８重量％の
８！ｉｔチの
及び
８１量チの
から成るものであり、化合物（、）、（ｂ）、（ｃ）は
、それぞれ下記の式で示されるものである。In addition, the base liquid crystal (A) is 8% by weight of 8% by weight of 8% by weight of 8% by weight. Compounds (, ), (b), and (c) are each represented by the following formula.
第２表
（Ａ） １．６５ ２１．
０（Ａ）＋（＆ｌ ） １．４５
２５．６（Ａ） ＋ （ム２） １．ｓｏ
２７．１（Ａ）十（Ｊ％３） １．
５０ ２７．３（Ａ）＋ （ａ）
１．４７ ２８．８（Ａ）十（ｂ）
１．５３ ２９．８（Ａ）＋ （ｅ）
１．５３ ３０．０第２表から
、式（１）の化合物は、母体液晶（Ａ）のしきい値電圧
を減少させ、かつ、粘度の上昇が小幅に抑えられている
のに対し、しきい値電圧を低下てせる目的で使用されて
いる上記の公知化合物（ａ）、（ｂ）、（ｃ）は、母体
液晶（Ａ）のしきい値電圧を式（１）の化合物と同程度
低下させるものの、母体液晶（Ａ）の粘度を式（１）の
化合物に比べて上昇させていることが理解できる。この
結果から、母体液晶の粘度の上昇を小幅に抑えながらし
きい値電圧の低下を起こさせる技術効果において、本発
明に係る化合物の優位性は明らかである。Table 2 (A) 1.65 21.
0(A)+(&l) 1.45
25.6(A) + (Mu2) 1. so
27.1(A) 10 (J%3) 1.
50 27.3(A)+(a)
1.47 28.8(A) 10(b)
1.53 29.8(A)+(e)
1.53 30.0 From Table 2, it can be seen that the compound of formula (1) reduces the threshold voltage of the host liquid crystal (A) and suppresses the increase in viscosity to a small extent; The above-mentioned known compounds (a), (b), and (c) used for the purpose of lowering the threshold voltage lower the threshold voltage of the host liquid crystal (A) to the same level as the compound of formula (1). It can be seen that although the viscosity of the base liquid crystal (A) is lowered, the viscosity of the base liquid crystal (A) is increased compared to that of the compound of formula (1). From this result, it is clear that the compound according to the present invention is superior in terms of the technical effect of causing a decrease in threshold voltage while suppressing an increase in the viscosity of the host liquid crystal to a small extent.
実施例１
Ｎ −（ｎ−へグチニル−１）−ピペリジン１８．１Ｎ
（０，１００モル）とトリエチルアミン１０．１．９（
０，１００七ル）のジエチルエーテル溶液２０ｒＩＬｌ
に３−フルオロ−４−ブロモフェニル−β−クロロビニ
ルケトン２６．４ ｉ （ｏ、１ｏｏモル）のジエチル
エーテル溶液を攪拌しながら室温で滴下後さらに室温で
１８時間反応させた。反応混合物に水を加えた後、反応
生成物をエーテルで抽出し、抽出液を水洗、乾燥後、こ
の液からエーテルを留去した。Example 1 N-(n-hegutynyl-1)-piperidine 18.1N
(0,100 mol) and triethylamine 10.1.9 (
0,100 liters) of diethyl ether solution 20 liters
A solution of 26.4 i (o, 10 mol) of 3-fluoro-4-bromophenyl-β-chlorovinyl ketone in diethyl ether was added dropwise at room temperature with stirring, and the mixture was further reacted at room temperature for 18 hours. After adding water to the reaction mixture, the reaction product was extracted with ether, the extract was washed with water, dried, and then the ether was distilled off from this liquid.
残留物に酢酸１５０ｄを加えて溶かした後、５Ｎ−ＨＣ
ｌ ３０ ｍＡ！を攪拌しながら加え、さらに室温で１
時間反応させた。次に酢酸アンモニウム２３．１．９（
０，３００モル）を上記反応液に加えた後、７時間還流
させた。冷却後、反応混合物を水で希釈し、反応生成物
をエーテルで抽出し、抽出液を水洗、乾燥後、この液か
らエーテルを留去した。得られた反応生成物をカラム精
製し、下記化合物１０．２Ｎ（０，０３１７モル）を得
た。After adding 150 d of acetic acid to the residue and dissolving it, 5N-HC
l 30 mA! was added with stirring, and then added at room temperature for 1
Allowed time to react. Then ammonium acetate 23.1.9 (
After adding 0,300 mol) to the above reaction solution, it was refluxed for 7 hours. After cooling, the reaction mixture was diluted with water, the reaction product was extracted with ether, the extract was washed with water, and after drying, the ether was distilled off from this liquid. The obtained reaction product was purified by column to obtain the following compound 10.2N (0,0317 mol).
これとシアン化第−銅３．２６ ＃ （０，０３６４モ
ル）をＮ、Ｎ−ツメチルホルムアミド５Ｑｍｌ中に加え
、６時間、還流させた。反応混合物を水５Ｑｍｌと濃塩
酸５ｄに塩化第二鉄水利物１３．９を溶解した溶液中に
注ぎ、６０〜７０℃で３０分加熱した。冷却後、反応混
合物を水で希釈し、反応生成物をエーテルで抽出し、抽
出液を水洗、乾燥後、この液からエーテルを留去した。This and 3.26 # (0,0364 mol) of cupric cyanide were added to 5 Qml of N,N-tmethylformamide, and the mixture was refluxed for 6 hours. The reaction mixture was poured into a solution of 13.9 ml of ferric chloride aquarium dissolved in 5 Q ml of water and 5 d of concentrated hydrochloric acid, and heated at 60 to 70°C for 30 minutes. After cooling, the reaction mixture was diluted with water, the reaction product was extracted with ether, the extract was washed with water, and after drying, the ether was distilled off from this liquid.
得られた反応生成物をカラム精製し下記化合物６．５２
、Ｓ＋ （０，０２４２モル）を得た。The obtained reaction product was purified by column to obtain the following compound 6.52.
, S+ (0,0242 mol) was obtained.
収率 ２４．２％ 転移温度 ２５℃（Ｃ→工）１０
℃（Ｉ ＃Ｎ）
実施例２
実施例１のＮ −（ｎ−へグチニル−１）−ピペリノン
の代わシにＮ（β−（トランス−４−ｎ−プロピルシク
ロヘキシル）−ビニル）−ビイリジンを用い、同様の要
領で下記化合物を得た。Yield 24.2% Transition temperature 25°C (C → Engineering) 10
°C (I #N) Example 2 N-(β-(trans-4-n-propylcyclohexyl)-vinyl)-biyridine was used in place of N-(n-heguthynyl-1)-piperinone in Example 1. , The following compound was obtained in the same manner.
収率 ２１．５％ 転移温度 ９２℃（Ｃ−＋Ｎ）１
８７℃（Ｎａｔ）
実施例３
実施例１のＮ −（ｎ−ヘプＪ炙−１）−ピペリじ：：
′＋Ｌジンの代ワりにＮ−（β−（４−ｎ−プロピルフ
ェニル）−ビニル）−ピペリジンを用い、同様の要領で
下記化合物を得た。Yield 21.5% Transition temperature 92°C (C-+N)1
87°C (Nat) Example 3 N-(n-hepJ-broiled-1)-piperidi of Example 1::
The following compound was obtained in the same manner using N-(β-(4-n-propylphenyl)-vinyl)-piperidine in place of '+L dine.
収率 ２２．４チ 転移温度 ９６℃（Ｃ−＋Ｎ）
１９３℃（Ｎａｒ）
〔発明の効果〕
本発明に係る式（１）の化合物は一般的な混合液晶に添
加した場合、混合液晶のしきい値電圧を顕著に低下させ
、且つ、粘度の上昇が従来同様の目的で使用されている
類似化合物と比較して小幅に抑えられている。従って、
本発明に係る式（１）の化合物は、低電圧駆動の液晶表
示セルを製作するための材料として極めて有用である。Yield: 22.4cm Transition temperature: 96°C (C-+N)
193°C (Nar) [Effects of the Invention] When the compound of formula (1) according to the present invention is added to a general mixed liquid crystal, it significantly lowers the threshold voltage of the mixed liquid crystal and prevents an increase in viscosity. Compared to similar compounds conventionally used for similar purposes, this is slightly suppressed. Therefore,
The compound of formula (1) according to the present invention is extremely useful as a material for manufacturing a liquid crystal display cell driven at a low voltage.
Claims (1)
わし、▲数式、化学式、表等があります▼は▲数式、化
学式、表等があります▼又は▲数式、化学式、表等があ
ります▼を表わし、▲数式、化学式、表等があります▼
はトランス（エカトリアル−エカトリアル）配置を表わ
し、ｎは０又は１である。 表される化合物。[Claims] General formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R represents a linear alkyl group having 1 to 10 carbon atoms, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
represents a trans (equatorial-equatorial) configuration, and n is 0 or 1. Compound represented.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22656486A JPS6383069A (en) | 1986-09-25 | 1986-09-25 | 2-(3-fluoro-4-cyanophenyl)pyridine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22656486A JPS6383069A (en) | 1986-09-25 | 1986-09-25 | 2-(3-fluoro-4-cyanophenyl)pyridine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6383069A true JPS6383069A (en) | 1988-04-13 |
Family
ID=16847132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22656486A Pending JPS6383069A (en) | 1986-09-25 | 1986-09-25 | 2-(3-fluoro-4-cyanophenyl)pyridine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6383069A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4409431B4 (en) * | 1993-04-03 | 2006-06-29 | Merck Patent Gmbh | Cyanophenylpyri (mi) din derivatives and liquid crystalline medium |
-
1986
- 1986-09-25 JP JP22656486A patent/JPS6383069A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4409431B4 (en) * | 1993-04-03 | 2006-06-29 | Merck Patent Gmbh | Cyanophenylpyri (mi) din derivatives and liquid crystalline medium |
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