JP3065094B2 - Halogenated phenylcyclohexyldioxane having an ether bond - Google Patents
Halogenated phenylcyclohexyldioxane having an ether bondInfo
- Publication number
- JP3065094B2 JP3065094B2 JP2256518A JP25651890A JP3065094B2 JP 3065094 B2 JP3065094 B2 JP 3065094B2 JP 2256518 A JP2256518 A JP 2256518A JP 25651890 A JP25651890 A JP 25651890A JP 3065094 B2 JP3065094 B2 JP 3065094B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- substituted
- cell
- phenylcyclohexyldioxane
- 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 - Fee Related
Links
- KSHKJRNIUGFAAT-UHFFFAOYSA-N 2-cyclohexyl-2-phenyl-1,4-dioxane Chemical class C1CCCCC1C1(C=2C=CC=CC=2)OCCOC1 KSHKJRNIUGFAAT-UHFFFAOYSA-N 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 40
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 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 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 description 43
- 210000004027 cell Anatomy 0.000 description 21
- -1 4-substituted benzoic acid Chemical class 0.000 description 13
- 239000012071 phase Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 230000007704 transition Effects 0.000 description 8
- 239000004988 Nematic liquid crystal Substances 0.000 description 7
- 230000005669 field effect Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- KTEARTXATWOYDB-UHFFFAOYSA-N 1-chloro-4-[1-(4-chlorophenyl)ethyl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)C1=CC=C(Cl)C=C1 KTEARTXATWOYDB-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 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
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Liquid Crystal Substances (AREA)
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有用なエーテル結
合を有するハロゲン化フェニルシクロヘキシルジオキサ
ンに関するものである。Description: TECHNICAL FIELD The present invention relates to a halogenated phenylcyclohexyldioxane having an ether bond, which is useful as an electro-optical display material.
液晶表示セルの代表的なものにエム・シャット（M.Sc
hadt）等〔APPLIED PHYSICS LETTERS 18,127〜128（197
1）〕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）またはジー・エイチ・ハ
イルマイヤー（G.H.Heilmeier）等〔PROCEEDING OF THE
I.E.E.E.56,1162〜1171（1968）〕によって提案された
動的光散型セル（ダイミック・スキャッタリング・モー
ド・セル）またはジー・エイチ・ハイルマイヤー（G.H.
Heilmeier）等〔APPLIED PHYSICS LETTERS 13,91（196
8）〕あるいはディー・エル・ホワイト（D.L.White）等
［JOURNAL OF APPLIED PHYSICS 45,4718（1974）］によ
って提案されたゲスト・ホスト型セルなどがある。A typical liquid crystal display cell is M-Shut (M.Sc
hadt) etc. [APPLIED PHYSICS LETTERS 18,127-128 (197
1)] [PROCEEDING OF THE] such as a field effect type cell (field effect mode cell) or GH Heilmeier proposed by
IEEE56, 1162-1171 (1968)], a dynamic light-scattering cell (a dimic scattering mode cell) or a GH Heilmeier (GH).
Heilmeier) [APPLIED PHYSICS LETTERS 13,91 (196
8)] or a guest-host type cell proposed by DL White et al. [JOURNAL OF APPLIED PHYSICS 45, 4718 (1974)].
これらの液晶表示セルの中で現在主流をなすものは、
電界効果型セルの一種のTN型セルである。The mainstream of these liquid crystal display cells at present is
This is a kind of TN type field effect cell.
このTN方セルにおいては、ジー・バウワー（G.Baue
r）［Mol.Cryst.Liq.Cryst.63,45（1981）］によって報
告されているように、セル外観を損う原因となるセル表
面での干渉縞の発生を防止するために、セルに充填され
る液晶材料の屈折率の異方性Δｎとセルにおける液晶層
の厚さｄ（μｍ）の積をある特定の値に設定する必要が
ある。実用的に使用される液晶表示セルでは、Δｎ・ｄ
の値が0.5、1.0、1.6または2.2のいずれかに設定されて
いる。通常、Δｎ・ｄの値を0.5に設定した場合には、
視角特性が良くなるという特徴があり、Δｎ・ｄの値を
1.0、1.6または2.2に設定した場合には、正面からのコ
ントラストが良くなるという特徴がある。従って、どの
方向からも見やすい視角特性を重視する液晶表示セルの
場合は、Δｎ・ｄの値を0.5に設定し、特に正面からの
コントラストを重視する液晶表示セルの場合は、Δｎ・
ｄの値を1.0、1.6または2.2に設定するのが普通であ
る。In this TN cell, G. Baue
r) As reported by [Mol. Cryst. Liq. Cryst. 63, 45 (1981)], in order to prevent the occurrence of interference fringes on the cell surface, which would impair the appearance of the cell, It is necessary to set the product of the anisotropy Δn of the refractive index of the liquid crystal material to be filled and the thickness d (μm) of the liquid crystal layer in the cell to a specific value. In a practically used liquid crystal display cell, Δn · d
Is set to any of 0.5, 1.0, 1.6 or 2.2. Normally, when the value of Δn · d is set to 0.5,
There is a feature that the viewing angle characteristics are improved, and the value of Δn · d
When set to 1.0, 1.6 or 2.2, there is a feature that contrast from the front is improved. Therefore, the value of Δn · d is set to 0.5 for a liquid crystal display cell that emphasizes viewing angle characteristics that are easy to see from any direction, and particularly for a liquid crystal display cell that emphasizes contrast from the front, Δn · d
It is common to set the value of d to 1.0, 1.6 or 2.2.
一方、実用的に使用されている液晶表示セルにおける
液晶層の厚さｄは、通常、６〜10μｍの範囲内で設定さ
れるため、Δｎ・ｄの値を0.5に設定する場合は、Δｎ
の値の小さな液晶材料が必要となり、Δｎ・ｄの値を1.
0、1.6または2.2に設定する場合は、逆にΔｎの値の大
きな液晶材料が必要となる。このように、液晶表示セル
の表示特性に応じてΔｎの値が小さい液晶材料とΔｎの
値が大きい液晶材料が必要とされる。On the other hand, since the thickness d of the liquid crystal layer in a liquid crystal display cell that is practically used is usually set within a range of 6 to 10 μm, when the value of Δn · d is set to 0.5, Δn
Requires a liquid crystal material having a small value of Δn.d.
In the case of setting to 0, 1.6 or 2.2, a liquid crystal material having a large value of Δn is required. Thus, a liquid crystal material having a small value of Δn and a liquid crystal material having a large value of Δn are required in accordance with the display characteristics of the liquid crystal display cell.
また、TN型セルにおいては、混合液晶の誘電率異方性
Δεが正である必要があるため、Δεの値が大きく、し
きい値電圧が低く、低電圧で駆動できるネマチック液晶
化合物が必要とされている。In the TN type cell, since the dielectric anisotropy Δε of the mixed liquid crystal needs to be positive, a nematic liquid crystal compound which has a large value of Δε, a low threshold voltage, and can be driven at a low voltage is required. Have been.
本発明が解決しようとする課題は、Δｎの値が小さ
く、Δεの値が大きく、しきい値電圧の低い新規なネマ
チック液晶化合物を提供することにある。An object of the present invention is to provide a novel nematic liquid crystal compound having a small value of Δn, a large value of Δε, and a low threshold voltage.
本発明は、上記課題を解決するために、下記一般式
（Ｉ）で表される化合物を提供する。The present invention provides a compound represented by the following general formula (I) in order to solve the above problems.
〔式中、Ｒは炭素原子数１〜７の直鎖状アルキル基を
表し、ｎは１〜５の整数を表し、Ｘはフッ素原子または
塩素原子を表し、Ｙは水素原子またはフッ素原子を表
し、ジオキサン環およびシクロヘキサン環はトランス配
置である。〕 一般式（Ｉ）で表される化合物は下記に示すスキーム
に従って製造することができる。 [Wherein, R represents a linear alkyl group having 1 to 7 carbon atoms, n represents an integer of 1 to 5, X represents a fluorine atom or a chlorine atom, and Y represents a hydrogen atom or a fluorine atom. , The dioxane ring and the cyclohexane ring are in the trans configuration. The compound represented by the general formula (I) can be produced according to the following scheme.
このスキームは、式（II）と式（III）の化合物をト
ルエン中でｐ−トルエンスルホン酸の如き酸性触媒の存
在下に、還流温度で反応させて脱水するものである。 In this scheme, compounds of formulas (II) and (III) are dehydrated by reacting in toluene in the presence of an acidic catalyst such as p-toluenesulfonic acid at reflux temperature.
一般式（Ｉ）で表される化合物は、正の誘電率異方性
を有するネマチック液晶化合物であり、従って例えば、
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
の混合物の状態で動的光散乱型表示セルの材料として使
用することができ、また正また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
効果型表示セルの材料として使用することができる。The compound represented by the general formula (I) is a nematic liquid crystal compound having a positive dielectric anisotropy.
It can be used as a material of a dynamic light scattering type display cell in a state of a mixture with another nematic liquid crystal compound having a negative dielectric anisotropy, and other materials having a positive or negative dielectric anisotropy. It can be used as a material for a field effect display cell in a state of a mixture with a nematic liquid crystal compound.
一般式（Ｉ）で表される本発明の液晶化合物と混合し
て使用することのできる他のネマチック液晶化合物の好
ましい代表例としては、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ボ
ン酸４′−置換フェニルエステル、４−置換シクロヘキ
サンカルボン酸４′−置換ビフェニルエステル、４−
（４−置換シクロヘキサンカルボニルオキシ）安息香酸
４′−置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−置換４′−置換ビフェニル、４
−置換フェニル−４′−置換シクロヘキサン、４−置換
４″−置換ターフェニル、４−置換ビフェニル４′−置
換シクロヘキサン、２−（４−置換フェニル）−５−置
換ピリミジンなどを挙げることができる。Preferred representative examples of other nematic liquid crystal compounds that can be used by mixing with the liquid crystal compound of the present invention represented by the general formula (I) include, for example, 4-substituted benzoic acid 4′-.
Substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-substituted biphenyl ester, 4-substituted
(4-substituted cyclohexanecarbonyloxy) benzoic acid 4'-substituted phenyl ester, 4- (4-substituted cyclohexyl) benzoic acid 4'-substituted phenyl ester, 4-
(4-substituted cyclohexyl) benzoic acid 4'-substituted cyclohexyl ester, 4-substituted 4'-substituted biphenyl,
Examples include -substituted phenyl-4'-substituted cyclohexane, 4-substituted 4 "-substituted terphenyl, 4-substituted biphenyl 4'-substituted cyclohexane, 2- (4-substituted phenyl) -5-substituted pyrimidine and the like.
（実施例１） 式CH3O（CH2）3CH（CH2OH）２で表される化合物3.1g
（0.021mol）と式 で表される化合物4.7g（0.021mol）とに、トルエン50ml
およびｐ−トルエンスルホン酸・１水和物0.040g（0.00
021mol）を加えた後、これらを撹はんしながら還流温度
で３時間脱水反応を行った。室温まで冷却後、トルエン
層を飽和炭酸水素ナトリウム水溶液および飽和食塩水で
洗浄し、ついで乾燥した後、トルエンを留去して粗生成
物を得た。(Example 1) 3.1 g of a compound represented by the formula CH 3 O (CH 2 ) 3 CH (CH 2 OH) 2
(0.021mol) and the formula And 4.7 g (0.021 mol) of the compound represented by
And 0.040 g of p-toluenesulfonic acid monohydrate (0.00
After the addition of these, a dehydration reaction was carried out at reflux temperature for 3 hours while stirring them. After cooling to room temperature, the toluene layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated saline, and then dried. Then, toluene was distilled off to obtain a crude product.
これをシリカゲルカラムクロマトグラフィーを用いて
精製した後、エタノールから再結晶させて精製し、下記
化合物3.8g（0.011mol）を得た。収率は52％であった。This was purified by silica gel column chromatography, and then purified by recrystallization from ethanol to obtain 3.8 g (0.011 mol) of the following compound. The yield was 52%.
この液晶化合物の相転移温度は、71℃（Ｃ→Ｓ）、77
℃（ＳＮ）、95℃（ＮＩ）であった。 The phase transition temperature of this liquid crystal compound is 71 ° C. (C → S), 77 ° C.
° C (SN) and 95 ° C (NI).
（実施例２） 上記実施例１と同様にして下記化合物を得た。収率は
62％であった。(Example 2) The following compound was obtained in the same manner as in Example 1 above. The yield is
It was 62%.
この液晶化合物の相転移温度は、107℃（Ｃ→Ｎ）、1
23℃（ＮＩ）であった。 The phase transition temperature of this liquid crystal compound was 107 ° C. (C → N), 1
23 ° C. (NI).
（実施例３） 上記実施例１と同様にして下記化合物を得た。収率は
30％であった。(Example 3) The following compound was obtained in the same manner as in Example 1 above. The yield is
30%.
この液晶化合物の相転移温度は、81℃（Ｃ→Ｎ）、87
℃（ＮＩ）であった。 The phase transition temperature of this liquid crystal compound is 81 ° C. (C → N), 87 ° C.
° C (NI).
（実施例４） 上記実施例１と同様にして下記化合物を得た。収率は
23％であった。Example 4 The following compound was obtained in the same manner as in Example 1 above. The yield is
23%.
この液晶化合物の相転移温度は、95℃（Ｃ→Ｎ）、12
1℃（ＮＩ）であった。 The phase transition temperature of this liquid crystal compound is 95 ° C. (C → N), 12 ° C.
1 ° C. (NI).
（実施例５） 上記実施例１と同様にして下記化合物を得た。収率は
61％であった。Example 5 The following compound was obtained in the same manner as in Example 1 above. The yield is
It was 61%.
この液晶化合物の相転移温度は、80℃（Ｃ→Ｓ）、83
℃（ＳＮ）、142℃（ＮＩ）であった。 The phase transition temperature of this liquid crystal compound is 80 ° C. (C → S), 83
° C (SN) and 142 ° C (NI).
（実施例６） 上記実施例１と同様にして下記化合物を得た。収率は
17％であった。(Example 6) The following compound was obtained in the same manner as in Example 1 above. The yield is
17%.
この液晶化合物の相転移温度は、89℃（Ｃ→Ｎ）、13
8℃（ＮＩ）であった。 The phase transition temperature of this liquid crystal compound is 89 ° C. (C → N), 13 ° C.
The temperature was 8 ° C (NI).
（実施例７） 上記実施例１と同様にして下記化合物を得た。収率は
56％であった。(Example 7) The following compound was obtained in the same manner as in Example 1 above. The yield is
56%.
この液晶化合物の相転移温度は、82℃（Ｃ→Ｎ）、10
6℃（ＮＩ）であった。 The phase transition temperature of this liquid crystal compound is 82 ° C. (C → N), 10 ° C.
6 ° C. (NI).
上記実施例１ないし実施例７の各液晶化合物の相転移
温度を第１表に示した。Table 1 shows the phase transition temperatures of the liquid crystal compounds of Examples 1 to 7.
ただし第１表中、Ｃは結晶相、Ｓはスメクチック相、
Ｎはネマチック相、Ｉは等方性液体相をそれぞれ表わ
す。However, in Table 1, C is a crystal phase, S is a smectic phase,
N represents a nematic phase, and I represents an isotropic liquid phase.
（応用例） ネマチック液晶組成物の現在母体液晶として汎用され
ている下記混合液晶（Ａ）80重量部と、上記実施例１な
いし実施例７で得た各液晶化合物20重量部とを混合して
液晶組成物とした。また比較例として、実施例３の液晶
化合物と類似化学構造を有し、Δｎが小さく、正のΔε
を有する下記化合物（ａ）20重量部と、下記混合液晶80
重量部とからなる液晶組成物を調整した。 (Application Example) 80 parts by weight of the following mixed liquid crystal (A), which is currently widely used as a base liquid crystal of a nematic liquid crystal composition, and 20 parts by weight of each of the liquid crystal compounds obtained in Examples 1 to 7 are mixed. A liquid crystal composition was obtained. As a comparative example, it has a similar chemical structure to the liquid crystal compound of Example 3, has a small Δn, and has a positive Δε
20 parts by weight of the following compound (a) having
A liquid crystal composition consisting of parts by weight was prepared.
これら各液晶組成物の屈折率異方性Δｎと誘電異方性
Δεとしきい値電圧を測定した。これらの結果を第２表
に示した。The refractive index anisotropy Δn, dielectric anisotropy Δε, and threshold voltage of each of the liquid crystal compositions were measured. Table 2 shows the results.
なお、混合液晶（Ａ）は以下のような組成からなるも
のである。 The mixed liquid crystal (A) has the following composition.
また液晶混合物（ａ）は下記式で表されるの公知化合
物（特公昭63−44132号）である。 The liquid crystal mixture (a) is a known compound represented by the following formula (JP-B-63-44132).
第２表より、従来公知の液晶化合物（ａ）を混合液晶
（Ａ）に混合した際には、混合液晶（Ａ）のΔｎを増加
させ、Δεを減少させ、しきい値電圧を著しく上昇させ
てしまうのに対して、実施例３で得た液晶化合物を混合
液晶（Ａ）に混合した際には、混合液晶（Ａ）のΔｎを
減少させ、Δεを増加させ、しきい値電圧を顕著に低下
せしめることが確認できた。 From Table 2, when the conventionally known liquid crystal compound (a) is mixed with the mixed liquid crystal (A), Δn of the mixed liquid crystal (A) is increased, Δε is decreased, and the threshold voltage is significantly increased. On the other hand, when the liquid crystal compound obtained in Example 3 was mixed with the mixed liquid crystal (A), Δn of the mixed liquid crystal (A) was decreased, Δε was increased, and the threshold voltage was significantly increased. It was confirmed that it was lowered.
本発明の一般式（Ｉ）で表される化合物は、Δｎが小
さく、かつΔεが大きいため、現在母体液晶として汎用
されているネマチック混合液晶に混合することによって
混合液晶のΔｎを減少させるかあるいはさほど上昇させ
ることなく、Δεを増加させ、しきい値電圧を顕著に低
下させることができる。Since the compound represented by the general formula (I) of the present invention has a small Δn and a large Δε, it is possible to reduce the Δn of the mixed liquid crystal by mixing it with a nematic mixed liquid crystal currently widely used as a base liquid crystal, or It is possible to increase Δε without significantly increasing the threshold voltage and to significantly reduce the threshold voltage.
また本発明の化合物は、構造類似の公知化合物と比
べ、その効果は顕著であり、視角特性に優れた低電圧駆
動可能なTN型液晶表示セルを作製するための材料として
極めて有用である。The compound of the present invention has a remarkable effect as compared with known compounds having similar structures, and is extremely useful as a material for producing a TN liquid crystal display cell having excellent viewing angle characteristics and capable of being driven at a low voltage.
フロントページの続き (72)発明者 マルチン シヤツト スイス国 シーエイチ―4411 ゼルテイ スベルク リースタラーストラッセ 77 (72)発明者 リヒヤルト ブーフエツカー スイス国 シーエイチ―8008 チユーリ ツヒ フエルゼンストラツセ 10 (56)参考文献 特開 平３−294275（ＪＰ，Ａ) 特開 昭58−159488（ＪＰ，Ａ) 特開 昭59−62533（ＪＰ，Ａ) 特開 昭60−226835（ＪＰ，Ａ) 特表 平４−503678（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07D 319/06 C09K 19/34 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)Continuing on the front page (72) Inventor Martin Schutz, Switzerland-4411 Zeltey Sberg, Riestelstrasse 77 (72) Inventor Richard Buchuetzker, Switzerland CH-8008 Tyuri Züch Felsenstrasse 10 (56) References JP-A 3- 294275 (JP, A) JP-A-58-159488 (JP, A) JP-A-59-62533 (JP, A) JP-A-60-226835 (JP, A) JP-A-4-503678 (JP, A) (58) Field surveyed (Int. Cl. 7 , DB name) C07D 319/06 C09K 19/34 CA (STN) REGISTRY (STN)
Claims (3)
し、ｎは１〜５の整数を表し、Ｘはフッ素原子または塩
素原子を表し、Ｙは水素原子またはフッ素原子を表し、
ジオキサン環およびシクロヘキサン環はトランス配置で
ある。〕1. A compound represented by the following general formula (I). [Wherein, R represents a linear alkyl group having 1 to 7 carbon atoms, n represents an integer of 1 to 5, X represents a fluorine atom or a chlorine atom, and Y represents a hydrogen atom or a fluorine atom. ,
The dioxane and cyclohexane rings are in the trans configuration. ]
物。2. The compound according to claim 1, wherein X is a fluorine atom.
物。3. The compound according to claim 1, wherein X is a chlorine atom.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2256518A JP3065094B2 (en) | 1990-04-12 | 1990-09-26 | Halogenated phenylcyclohexyldioxane having an ether bond |
| DE69110733T DE69110733T2 (en) | 1990-04-12 | 1991-04-09 | Phenylcyclohexyldioxane derivatives with an ether bond for electro-optical substances. |
| EP91810258A EP0452274B1 (en) | 1990-04-12 | 1991-04-09 | Phenylcyclohexyldioxane derivatives having an ether bond for electro-optical displays |
| US07/683,009 US5171472A (en) | 1990-04-12 | 1991-04-10 | Phenylcyclohexyldioxane derivatives having an ether bond for electro-optical displays |
| KR1019910005782A KR0166379B1 (en) | 1990-04-12 | 1991-04-11 | Phenylcyclodioxane derivatives having an ether bond |
| HK98105005A HK1005873A1 (en) | 1990-04-12 | 1998-06-05 | Phenylcyclohexyldioxane derivatives having an ether bond for electro-optical displays |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2-97060 | 1990-04-12 | ||
| JP9706090 | 1990-04-12 | ||
| JP2256518A JP3065094B2 (en) | 1990-04-12 | 1990-09-26 | Halogenated phenylcyclohexyldioxane having an ether bond |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0418089A JPH0418089A (en) | 1992-01-22 |
| JP3065094B2 true JP3065094B2 (en) | 2000-07-12 |
Family
ID=26438266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2256518A Expired - Fee Related JP3065094B2 (en) | 1990-04-12 | 1990-09-26 | Halogenated phenylcyclohexyldioxane having an ether bond |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3065094B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998017664A1 (en) * | 1996-10-22 | 1998-04-30 | Chisso Corporation | Dioxane derivatives, liquid-crystal compositions containing the same, and liquid-crystal display devices made by using the same |
| US10655065B2 (en) | 2016-08-01 | 2020-05-19 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
-
1990
- 1990-09-26 JP JP2256518A patent/JP3065094B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0418089A (en) | 1992-01-22 |
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