JPH0273050A - Liquid crystal compound - Google Patents
Liquid crystal compoundInfo
- Publication number
- JPH0273050A JPH0273050A JP63225707A JP22570788A JPH0273050A JP H0273050 A JPH0273050 A JP H0273050A JP 63225707 A JP63225707 A JP 63225707A JP 22570788 A JP22570788 A JP 22570788A JP H0273050 A JPH0273050 A JP H0273050A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- liquid crystal
- formula
- trans
- propylcyclohexyl
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 37
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 abstract description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 14
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract description 13
- 230000007704 transition Effects 0.000 abstract description 5
- 238000002156 mixing Methods 0.000 abstract description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000012769 display material Substances 0.000 abstract description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- SPBMPELOCAOZLY-UHFFFAOYSA-N 4-(4-ethyl-2-fluorophenyl)benzonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C(C=C(C=C1)CC)F SPBMPELOCAOZLY-UHFFFAOYSA-N 0.000 description 1
- HTRNHWBOBYFTQF-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylbenzene Chemical group FC1=CC(Br)=CC=C1C1=CC=CC=C1 HTRNHWBOBYFTQF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電気光学的表示材料として用いられる新規な液
晶化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel liquid crystal compound used as an electro-optical display material.
本発明は一般式
（上式中、Ｒは炭素原子数が１〜１２の直鎖アルキル基
を示し、シクロヘキサン環はトランス配置である。）で
表わされる新規な液晶化合物であり、ネマチック液晶相
を有する。また本発明の液晶化合物は以下に示す特徴を
有する。The present invention is a novel liquid crystal compound represented by the general formula (in the above formula, R represents a linear alkyl group having 1 to 12 carbon atoms, and the cyclohexane ring has a trans configuration), and exhibits a nematic liquid crystal phase. have Furthermore, the liquid crystal compound of the present invention has the following characteristics.
１、結晶−ネマチック相転移温度（以下、Ｃ−Ｎ点とい
う）が低い。1. Low crystal-nematic phase transition temperature (hereinafter referred to as C-N point).
２、ネマチック相−等方性液体転移点（以下、Ｎ−Ｉ点
という）が非常に高い。2. The nematic phase-isotropic liquid transition point (hereinafter referred to as NI point) is very high.
３、誘電率の異方性（以下、Δεという）が正で大きい
０．
４、複屈折率（以下、Δηという）が小さい。3. The dielectric constant anisotropy (hereinafter referred to as Δε) is positive and large. 4. Low birefringence (hereinafter referred to as Δη).
したがって、本発明の化合物（１）と他の液晶化合物を
混合した液晶組成物を用いることにより実用温度範囲が
広く、駆動電圧が低く、さらにしきい値特性の良い液晶
表示装置を提供することができる。Therefore, by using a liquid crystal composition obtained by mixing the compound (1) of the present invention with another liquid crystal compound, it is possible to provide a liquid crystal display device with a wide practical temperature range, low driving voltage, and good threshold characteristics. can.
液晶表示装置は液晶の持つ電気光学効果を利用したもの
であり、これに用いられる液晶相にはネマチック相、コ
レステリック相、スメクチック相がある。そして最も広
く用いられているネマチック相を利用した表示方式には
ねじれネマチック型（ＴＮ型）、動的散乱型、ゲスト−
ホスト型などがある。Liquid crystal display devices utilize the electro-optic effect of liquid crystals, and liquid crystal phases used therein include nematic phase, cholesteric phase, and smectic phase. Display methods using the most widely used nematic phase include twisted nematic type (TN type), dynamic scattering type, and guest-type.
There are host types.
液晶表示装置は １、小型でしかも薄くできる。liquid crystal display device 1. Can be made small and thin.
２、駆動電圧が低く、且つ消費電力が小さい。2. Low driving voltage and low power consumption.
３、受光素子であるため長時間使用しても目が疲れない
。3. Since it is a light-receiving element, your eyes won't get tired even if you use it for a long time.
等の長所を持つことから、従来よりウォッチ、電卓、オ
ーディオ機器、各種計測器、自動車のダツシュボード等
に応用されている。特に最近ではパーソナルコンピュー
ターやワードプロセッサーのデイスプレィさらには白黒
又はカラーのポケットテレビなどの画素数のたいへん多
い表示にも応用されＣＲＴに代わる表示装置として注目
を集めている。この様に液晶表示装置は多方面に応用さ
れており、今後さらにその応用分野は拡大してゆくと考
えられる。これに伴ない液晶材料に要求される特性も変
化してゆくと思われるが、以下に示した特性は基本的な
もので必要不可欠である。Because of these advantages, it has been applied to watches, calculators, audio equipment, various measuring instruments, automobile dashboards, etc. Particularly recently, it has been applied to displays with a large number of pixels, such as displays of personal computers and word processors, as well as black-and-white or color pocket televisions, and is attracting attention as a display device that can replace CRTs. As described above, liquid crystal display devices are being applied in many fields, and it is thought that the fields of application will further expand in the future. It is thought that the characteristics required of liquid crystal materials will change along with this, but the characteristics shown below are basic and indispensable.
１、着色がなく、熱、光、電気的、化学的に安定である
こと。1. Must be non-colored and thermally, optically, electrically and chemically stable.
２、実用温度範囲が広いこと。2. Wide practical temperature range.
３、電気光学的な応答速度が速いこと。3. Fast electro-optical response speed.
４、駆動電圧が低いこと。4. Low driving voltage.
５、電圧−光透過率特性の立ちあがりが急峻であり、ま
たそのしきい値電圧の温度依存性が小さいこと。5. The rise of the voltage-light transmittance characteristic is steep, and the temperature dependence of the threshold voltage is small.
６、視角範囲が広いこと。6. Wide viewing angle range.
これらの特性のうち、１の特性を満足する液晶は数多く
知られているが、２以下の特性を単一成分で満足させる
液晶化合物は知られていない、そこでこれらの特性を得
るために数種類のネマチック液晶化合物又は非液晶化合
物を混合した液晶組成物を用いている。そして一般的に
は比較的低分子１でＣ−Ｎ点（又は融点）が室温付近の
液晶化合物と高分子量でＮ−Ｉ点が２００’ Ｃ以上あ
る液晶化合物を組み合せた組成物が用いられ、２の特性
を満足させるためにはＮ−Ｉ点ができるだけ高くしかも
Ｃ−Ｎ点ができるだけ低い液晶化合物が不可欠である。Among these properties, many liquid crystals that satisfy property 1 are known, but there are no liquid crystal compounds that satisfy property 2 or less with a single component.Therefore, several types of liquid crystal compounds are known that satisfy property 2 or less with a single component. A liquid crystal composition containing a nematic liquid crystal compound or a non-liquid crystal compound is used. Generally, a composition is used that combines a liquid crystal compound with a relatively low molecular weight and a C-N point (or melting point) near room temperature, and a liquid crystal compound with a high molecular weight and an N-I point of 200' C or more. In order to satisfy the characteristics No. 2, it is essential to have a liquid crystal compound with an N-I point as high as possible and a C-N point as low as possible.
しかし、従来のＮ−Ｉ点が２００６Ｃ以上ある液晶化合
物は第１表に示したようにＣ−Ｎ点は比較的低いがＮ−
Ｉ点は２５０°Ｃ以下である。However, as shown in Table 1, conventional liquid crystal compounds with an N-I point of 2006C or higher have relatively low C-N points, but N-
Point I is below 250°C.
４の特性を満足させるためにはしきい値電圧を下げなけ
ればいけないが、しきい値電圧Ｖｔｈと弾性定数にと認
電率の異方性Δεとの間には次の関係があり、しきい値
電圧を下げるにはΔεが大きくＫが小さい液晶物質が必
要となる。In order to satisfy characteristic 4, the threshold voltage must be lowered, but there is the following relationship between the threshold voltage Vth, the elastic constant, and the anisotropy Δε of the acceptance rate. In order to lower the threshold voltage, a liquid crystal material with a large Δε and a small K is required.
また５、６の特性についてはΔ７が影響を及ぼす一つの
要因であるが、現在知られている液晶化合物はΔηの大
きいものが多く、液晶組成物のΔηを目的に合った値に
するためにはΔηの小さな液晶化合物が必要となる。Regarding the characteristics 5 and 6, Δ7 is one of the factors that influences it, but many of the currently known liquid crystal compounds have a large Δη, so it is necessary to adjust the Δη of the liquid crystal composition to a value that suits the purpose. requires a liquid crystal compound with a small Δη.
そこで本発明はこのような実状における要請に応じるも
のであり、その目的は他の１種又は２種以上のネマチッ
ク液晶化合物又は非液晶化合物と混合することにより実
用温度範囲が広く、Δηが小さくしかもしきい値電圧の
低い液晶組成物を得ることができる新規な液晶化合物を
提供することである。Therefore, the present invention meets the needs of these actual situations, and its purpose is to widen the practical temperature range, reduce Δη, and reduce Δη by mixing it with one or more other nematic liquid crystal compounds or non-liquid crystal compounds. An object of the present invention is to provide a novel liquid crystal compound from which a liquid crystal composition with a low threshold voltage can be obtained.
本発明は一般式
（上式中、Ｒは炭素原子数が１〜１２の直鎖アルキル基
を示し、シクロヘキサン環はトランス配置である。）で
表わされる液晶化合物である。The present invention is a liquid crystal compound represented by the general formula (in the above formula, R represents a linear alkyl group having 1 to 12 carbon atoms, and the cyclohexane ring has a trans configuration).
本発明の化合物（１）は次の製造方法により得ることか
できる。Compound (1) of the present invention can be obtained by the following production method.
（上式中、Ｒは炭素原子数が１〜１２の直鎖アルキル基
を示し、シクロヘキサン環はトランス配置である。）
工程１ 窒素気流下、化合物（２）を脱水テトラヒドロ
フラン（ＴＨＦ）中ヨウ素を触媒に用いてマグネシウム
を反応させグリニヤール試薬（３）を調整する。(In the above formula, R represents a straight-chain alkyl group having 1 to 12 carbon atoms, and the cyclohexane ring has a trans configuration.) Step 1 Under a nitrogen atmosphere, compound (2) is dehydrated and iodine is added in tetrahydrofuran (THF). A Grignard reagent (3) is prepared by reacting magnesium using a catalyst.
工程２ 窒素気流下、グリニヤール試薬（３）と化合物
く４）を塩化第一銅（ＣｕＣ１）触媒下にカップリング
反応をさせ化合物（５）を得る。Step 2 Under a nitrogen stream, Grignard reagent (3) and compound 4) are subjected to a coupling reaction under a cuprous chloride (CuC1) catalyst to obtain compound (5).
工程３ 化合物（５）を二硫化炭素溶媒中で無水塩化ア
ルミニウムを触媒に用い、塩化アセチルとフリーデルク
ラフッ反応をさせ化合物（６）を得る。Step 3 Compound (5) is reacted with acetyl chloride using anhydrous aluminum chloride as a catalyst in a carbon disulfide solvent to obtain Compound (6).
工程４ 化合物（６）を１．４−ジオキサン溶媒中で臭
素と水酸化ナトリウム水溶液から調整した次亜臭素酸ナ
トリウム（ＮａＯＢｒ）水溶液又は市販の次亜塩素酸ナ
トリウム水溶液（Ｎａ００１）とへロホルム反応させ化
合物（７）を得る。Step 4 Compound (6) is reacted with heroform with a sodium hypobromite (NaOBr) aqueous solution prepared from bromine and a sodium hydroxide aqueous solution or a commercially available sodium hypochlorite aqueous solution (Na001) in a 1,4-dioxane solvent. Compound (7) is obtained.
工程５ 化合物（７）を塩化チオニルで塩素化して化合
物（８）を得る。Step 5 Compound (7) is chlorinated with thionyl chloride to obtain compound (8).
工程６ 化合物（８）をアセトン溶媒中アンモニア水と
反応させ化合物（９）を得る。Step 6 Compound (8) is reacted with aqueous ammonia in an acetone solvent to obtain compound (9).
工程７ 化合物（９）を塩化チオニル又はオキシ塩化リ
ン等で脱水して本発明の新規液晶化合物（１）を得る。Step 7 Compound (9) is dehydrated with thionyl chloride or phosphorus oxychloride to obtain the novel liquid crystal compound (1) of the present invention.
以下、実施例と応用例により本発明をさらに詳しく説明
する。Hereinafter, the present invention will be explained in more detail with reference to Examples and Application Examples.
実施例１
１−〔トランス−４”−（）ランス−４″′ −プロ
ピルシクロヘキシル）シクロヘキシル〕−２−（２−フ
ルオロ−４′−シアノビフェニル−４−イル）エタン（
化合物（１）でＲがＣｓＨ＋＋のもの）の製造方法。Example 1 1-[trans-4''-()trans-4'''-propylcyclohexyl)cyclohexyl]-2-(2-fluoro-4'-cyanobiphenyl-4-yl)ethane (
A method for producing compound (1) in which R is CsH++.
工程１ 窒素気流下、削状マグネシウム２．４ｇを加温
、攪拌して活性化した。ヨウ素０．１ｇとＴＨＦ３０ｍ
ｌを加え、次に４−ブロモ−２−フルオロビフェニル１
３．８ｇをＴＨＦ８０ｍｌに溶した溶液を滴下した０滴
下が終了したら５０°Ｃで３時間攪拌してグリニヤール
試薬のＴＨＦ溶液を調整した。Step 1 Under a nitrogen stream, 2.4 g of magnesium chips were activated by heating and stirring. 0.1g of iodine and 30m of THF
1 and then 4-bromo-2-fluorobiphenyl 1
A solution of 3.8 g dissolved in 80 ml of THF was added dropwise. After the completion of the dropwise addition, the mixture was stirred at 50° C. for 3 hours to prepare a THF solution of the Grignard reagent.
工程２ 工程１で調整したグリニヤール試薬のＴＨＦ溶
液を窒素気流下で濾過し、その中へ１−〔トランス−４
−（トランス−４′−プロピルシクロヘキシル）シクロ
ヘキシル〕−２−ブロモエタン１５．２ｇと塩化第一銅
５ｍｇをＴＨＦ ３０ ｍ ｌ Ｉ：、溶した溶液を２
時間かけて滴下した６滴下終了後６４時間還流した０３
反応液を冷却し１０％塩酸１００ｍ１を加えクロロホル
ムで抽出し、１０％塩酸、水の順で洗浄した。クロロホ
ルムを蒸留後、残渣をシリカゲルカラムでクロロホルム
溶媒を用いて処理し１−〔トランス−４“−（トランス
−４゛″′−プロピルシクロヘキシル）シクロヘキシル
） −２−（２−フルオロビフェニル−４−イル）エタ
ン１１．９ｇを得た。Step 2 The THF solution of the Grignard reagent prepared in Step 1 was filtered under a nitrogen stream, and 1-[trans-4
-(trans-4'-propylcyclohexyl)cyclohexyl]-2-bromoethane (15.2 g) and cuprous chloride (5 mg) in THF (30 ml I), a solution of 2
03 which was refluxed for 64 hours after the completion of 6 drops which were added over time
The reaction solution was cooled, 100 ml of 10% hydrochloric acid was added, extracted with chloroform, and washed successively with 10% hydrochloric acid and water. After distilling off chloroform, the residue was treated with chloroform solvent on a silica gel column to obtain 1-[trans-4"-(trans-4"'-propylcyclohexyl)cyclohexyl)-2-(2-fluorobiphenyl-4-yl). ) 11.9 g of ethane was obtained.
工程３ 粉細した無水塩化アルミニウム５．３ｇを二硫
化炭素４５ｍ１に分散させ、攪拌しながら塩化アセチル
２．９ｇを滴下した０次に食塩−氷浴で００Ｃ以下に冷
却し、攪拌しながら１−〔トランス−４”−（１−ラン
ス−４″′ −プロピルシクロヘキシル）シクロヘキシ
ル〕−２−（２−フルオロビフェニル−４−イル）エタ
ン１１．９ｇを二硫化炭素１００ｍ１に溶した溶液を滴
下した６滴下終了後、ざらに０°Ｃ以下で２時間攪拌し
た。反応物を塩酸と水中に注ぎ、二硫化炭素を水蒸気蒸
留してから水層をクロロホルムで抽出して１０％塩酸と
水で洗浄した。Step 3 5.3 g of powdered anhydrous aluminum chloride was dispersed in 45 ml of carbon disulfide, and 2.9 g of acetyl chloride was added dropwise with stirring. Next, the mixture was cooled to below 00C in a salt-ice bath, and 1- A solution of 11.9 g of [trans-4"-(1-trans-4"'-propylcyclohexyl)cyclohexyl]-2-(2-fluorobiphenyl-4-yl)ethane dissolved in 100 ml of carbon disulfide was added dropwise. After the dropwise addition was completed, the mixture was roughly stirred at 0°C or lower for 2 hours. The reaction mixture was poured into hydrochloric acid and water, carbon disulfide was steam distilled, and the aqueous layer was extracted with chloroform and washed with 10% hydrochloric acid and water.
クロロホルムを蒸留後、残渣をアセトン中から再結晶し
、１−〔トランス−４″−プロピルシクロヘキシル）シ
クロヘキシル）−２−（２−フルオロ−４′−アセチル
−４−イル）エタン１１゜ ２ｇを？ｑだ。After distilling off the chloroform, the residue was recrystallized from acetone to obtain 11°2 g of 1-[trans-4''-propylcyclohexyl)cyclohexyl)-2-(2-fluoro-4'-acetyl-4-yl)ethane. It's q.
工程４ １−（１−ランス−４″−プロピルシクロヘキ
シル）シクロヘキシル） −２−（２−フルオロ−４′
−アセチル−４−イル）エタン１１゜２ｇを１．４−ジ
オキサン１５０ｍ１中へ入れ、この混合物を氷水浴で５
°Ｃ以下に冷却し、激しく攪拌しながら臭素１６．２ｇ
と水酸化ナトリウム１０．２ｇとから調整した次亜臭素
酸ナトリウム溶液を滴下した。滴下終了後、さらに５°
Ｃ以下で１時間と４０°Ｃで１時間攪拌した０反応液に
１０％塩酸を加えて結晶を析出させた。結晶を濾過し水
で充分洗浄した。この結晶をエタノールから再結晶して
１−〔トランス−４“−プロピルシクロヘキシル）シク
ロヘキシル）−２−（２−フルオロ−４′−力ルボキシ
−４−イル〕エタン９．６ｇを得た。Step 4 1-(1-lance-4″-propylcyclohexyl)cyclohexyl)-2-(2-fluoro-4′
11.2 g of -acetyl-4-yl)ethane were placed in 150 ml of 1,4-dioxane, and the mixture was heated in an ice-water bath for 50 minutes.
16.2 g of bromine while cooling to below °C and stirring vigorously.
A sodium hypobromite solution prepared from and 10.2 g of sodium hydroxide was added dropwise. After dropping, add another 5°
10% hydrochloric acid was added to the reaction solution which was stirred for 1 hour at 40°C or lower and for 1 hour at 40°C to precipitate crystals. The crystals were filtered and thoroughly washed with water. The crystals were recrystallized from ethanol to obtain 9.6 g of 1-[trans-4''-propylcyclohexyl)cyclohexyl)-2-(2-fluoro-4'-carboxy-4-yl]ethane.
工程５ 工程４で得た１−〔トランス−４″−プロピル
シクロヘキシル）シクロヘキシル〕−２（２−フルオロ
−４′−力ルボキシ−４−イル）エタン９．６ｇを塩化
チオニル１６ｍ１と件に５時間還流した。その後アスピ
レータ−減圧下に過剰な塩化チオニルを蒸留した。次に
残渣をトルエン１５ｍ１に溶解してからアスピレ−減圧
下にトルエンを蒸留した。残漬をヘキサンから再結晶し
て１−〔トランス−４″プロピルシクロヘキシル）シク
ロヘキシル〕−２−（２−フルオロ−４′−クロロホル
ミル−４−イル）エタン８．７ｇを得た。Step 5 9.6 g of 1-[trans-4″-propylcyclohexyl)cyclohexyl]-2(2-fluoro-4′-carboxy-4-yl)ethane obtained in Step 4 was mixed with 16 ml of thionyl chloride for 5 hours. The excess thionyl chloride was then distilled off under aspirator vacuum. The residue was then dissolved in 15 ml of toluene, and the toluene was distilled off under aspirator vacuum. The residue was recrystallized from hexane to give 1-[ 8.7 g of trans-4''propylcyclohexyl)cyclohexyl]-2-(2-fluoro-4'-chloroformyl-4-yl)ethane was obtained.
工程６ 工程５で得た１−〔トランス−４“−プロピル
シクロヘキシル）シクロヘキシル〕−２−（２−フルオ
゛ロー４′−クロロホルミル−４−イル）エタン８，７
ｇをアセトン３５ｍ１に溶解した液を氷水浴で５°Ｃ以
下に冷却し、そし中へ漬アンモニア水１９ｍ１を激しく
攪拌しながら滴下した。析出した結晶を濾過し、アンモ
ニア臭が消えるまで水で洗浄した。この結晶を８０１０
で乾燥し、１−〔トランス−４“プロピルシクロヘキシ
ル）シクロヘキシル〕−２−（２−フルオロ−４′−ア
ミド−４−イル〕エタン７．７ｇを得た。Step 6 1-[trans-4"-propylcyclohexyl)cyclohexyl]-2-(2-fluoro-4'-chloroformyl-4-yl)ethane 8,7 obtained in Step 5
A solution obtained by dissolving G in 35 ml of acetone was cooled to below 5°C in an ice-water bath, and 19 ml of diluted ammonia water was added dropwise into the solution with vigorous stirring. The precipitated crystals were filtered and washed with water until the ammonia odor disappeared. This crystal is 8010
to obtain 7.7 g of 1-[trans-4"propylcyclohexyl]cyclohexyl]-2-(2-fluoro-4'-amido-4-yl)ethane.
工程７ 工程６で得た１−〔トランス−４“−プロピル
シクロヘキシル）シクロヘキシル〕−２−（２−フルオ
ロ−４′−アミド−４−イル）エタン７．７ｇと塩化チ
オニル２５ｍ１を２０時間還流した。過剰な塩化チオニ
ルをアスピレータ−減圧下に蒸留した。残渣をクロロホ
ルムとアセトンの混合溶媒から再結晶して１−〔トラン
ス−４“−（トランス−４″′−プロピルシクロヘキシ
ル）シクロヘキシル）−２−（２−フルオロ−４′−シ
アノビフェニル−４−イル）エタン５．４ｇを得た。こ
の化合物を液体クロマトグラフで分析したところ１００
．０％であった。またＤＳＣの測定よりこの化合物の相
転移温度は以下のとおりであった。Step 7 7.7 g of 1-[trans-4"-propylcyclohexyl)cyclohexyl]-2-(2-fluoro-4'-amido-4-yl)ethane obtained in Step 6 and 25 ml of thionyl chloride were refluxed for 20 hours. Excess thionyl chloride was distilled under reduced pressure using an aspirator. The residue was recrystallized from a mixed solvent of chloroform and acetone to give 1-[trans-4"-(trans-4"'-propylcyclohexyl)cyclohexyl)-2- 5.4 g of (2-fluoro-4'-cyanobiphenyl-4-yl)ethane was obtained.This compound was analyzed by liquid chromatography and showed 100%
．． It was 0%. Further, the phase transition temperature of this compound was as follows from measurement by DSC.
くここで、Ｃ１およびＣ２は結晶相、Ｎはネマチック相
、工は等方性液体を示す、）
応用例１
市販の混合液晶ＺＬＩ−１５６５（メルク社製、Ｎ−Ｉ
点８９．３°Ｃ）をベース液晶とし、現在一般的にＮ−
Ｉ点を高くする目的で使用されている４−ペンチル−４
“−シアノターフェニルと本発明化合物である実施例１
の１−〔トランス−４−（トランス−４″′−プロピル
シクロヘキシル）シクロヘキシル）−２−（２−フルオ
ロ−４′シアノビフェニル−４−イル）エタンの特性比
較を行なった。(Here, C1 and C2 are crystalline phases, N is a nematic phase, and N is an isotropic liquid.) Application example 1 Commercially available mixed liquid crystal ZLI-1565 (manufactured by Merck & Co., Ltd., N-I
Point 89.3°C) is used as the base liquid crystal, and currently N-
4-pentyl-4, which is used to increase the I point
“-Cyanoterphenyl and the compound of the present invention Example 1
The properties of 1-[trans-4-(trans-4''-propylcyclohexyl)cyclohexyl)-2-(2-fluoro-4'cyanobiphenyl-4-yl)ethane were compared.
ＺＬＩ−１５６５
９０重量部
〔組成物Ｂ〕
ＺＬＩ−１５６５
９０重量部
よりなる組成物Ａ及びＢを作り、それぞれ厚さ７μｍの
ＴＮセルに封入し、交流スタテック駆動、２５°Ｃで電
圧−輝度特性を測定した。結果を第２表に示す。90 parts by weight of ZLI-1565 [Composition B] Compositions A and B consisting of 90 parts by weight of ZLI-1565 were prepared, each was sealed in a 7 μm thick TN cell, and the voltage-luminance characteristics were measured under AC static drive at 25°C. was measured. The results are shown in Table 2.
第２表 ＴＮセル測定方向θ＝９０°Ｃからの測定値である。Table 2 These are the measured values from the TN cell measurement direction θ=90°C.
以上に述べた如く、一般的な液晶組成物に本発明の化合
物を混合することにより、実用温度範囲、しきい値特性
の向上が確認された。よって本発明の液晶化合物はネマ
チック液晶組成物の混合成分として大いに有用である。As described above, it was confirmed that the practical temperature range and threshold characteristics were improved by mixing the compound of the present invention into a general liquid crystal composition. Therefore, the liquid crystal compound of the present invention is highly useful as a mixed component of a nematic liquid crystal composition.
以 上 出願人 セイコーエプソン株式会社that's all Applicant: Seiko Epson Corporation
Claims (1)
を示し、シクロヘキサン環はトランス配置である。） で表わされる液晶化合物。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (In the above formula, R represents a straight-chain alkyl group having 1 to 12 carbon atoms, and the cyclohexane ring is in the trans configuration. .) A liquid crystal compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63225707A JPH0273050A (en) | 1988-09-09 | 1988-09-09 | Liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63225707A JPH0273050A (en) | 1988-09-09 | 1988-09-09 | Liquid crystal compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0273050A true JPH0273050A (en) | 1990-03-13 |
Family
ID=16833543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63225707A Pending JPH0273050A (en) | 1988-09-09 | 1988-09-09 | Liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0273050A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824543A (en) * | 2017-11-23 | 2019-05-31 | 江苏和成显示科技有限公司 | A kind of compound and its liquid-crystal composition and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60161956A (en) * | 1984-01-17 | 1985-08-23 | メルク・パテント・ゲゼルシャフト・ミツト・ベシュレンクテル・ハフツング | Ethane derivative |
-
1988
- 1988-09-09 JP JP63225707A patent/JPH0273050A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60161956A (en) * | 1984-01-17 | 1985-08-23 | メルク・パテント・ゲゼルシャフト・ミツト・ベシュレンクテル・ハフツング | Ethane derivative |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824543A (en) * | 2017-11-23 | 2019-05-31 | 江苏和成显示科技有限公司 | A kind of compound and its liquid-crystal composition and application |
| CN109824543B (en) * | 2017-11-23 | 2022-02-22 | 江苏和成显示科技有限公司 | Compound, liquid crystal composition and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5061400A (en) | Liquid crystal compounds | |
| EP0442266B1 (en) | Tolan derivatives, liquid crystal compositions containing them, and liquid crystal elements using them | |
| JPH1045642A (en) | Liquid crystal compound with extremely high dielectric constant anisotropy | |
| JPH05279279A (en) | Difluorocyclohexane derivative | |
| JPH0273050A (en) | Liquid crystal compound | |
| EP0390329B1 (en) | Pyrimidine derivative | |
| JP2897397B2 (en) | Difluorobenzonitrile derivative, liquid crystal composition containing the same, and liquid crystal display using the same | |
| JPH0525068A (en) | Terphenyl derivative, liquid crystal composition containing the same and liquid crystal display element using the same | |
| JPH0558981A (en) | Terphenyl derivative, liquid crystal composition containing the same and liquid crystal display element using the same | |
| JP3899557B2 (en) | Fluorobibiphenyl derivatives | |
| JPH05140043A (en) | Terphenyl derivative, liquid crystal composition containing the same derivative and liquid crystal element using the same composition | |
| JPH0338572A (en) | Pyrimidine derivative | |
| JP2636347B2 (en) | Fluoro compound | |
| JPH04356432A (en) | Cyclohexyl terphenyl derivative and liquid crystal composition containing the same and liquid crystal display element using the same | |
| JP3412211B2 (en) | 1,1-Difluoro-2-phenylethylene derivative, liquid crystal composition containing the same, and liquid crystal display device using the same | |
| JPH0656718A (en) | Fluorocyclohexane derivative | |
| JPH06298685A (en) | 3,5-difluorobiphenyl derivative | |
| JP2819682B2 (en) | Pyrimidine derivative and liquid crystal composition | |
| JPH05140042A (en) | Unsaturated esters | |
| JPH04257535A (en) | Thrphenyl derivative, liquid crystal composition containing the same and liquid crystal display element using the same | |
| JPH04169573A (en) | Pyrimidine derivative, liquid crystal composition containing the derivative and liquid crystal display element produced by using the same | |
| JPH04312546A (en) | Biphenyl derivative, liquid crystal composition containing the derivative and time-shared liquid crystal display element using the composition | |
| JPH0640971A (en) | Fluorotolan derivative | |
| JPH04266836A (en) | Terphenyl derivative, liquid crystalline composition containing the same derivative and liquid crystal display device using the same composition | |
| JPH04290859A (en) | Cyclohexylterphenyl derivative, liquid crystal composition containing the same and liquid crystal display element produced by using the composition |