JPH0418089A - Halogenated phenylcyclohexyldioxane having ether linkage - Google Patents
Halogenated phenylcyclohexyldioxane having ether linkageInfo
- Publication number
- JPH0418089A JPH0418089A JP25651890A JP25651890A JPH0418089A JP H0418089 A JPH0418089 A JP H0418089A JP 25651890 A JP25651890 A JP 25651890A JP 25651890 A JP25651890 A JP 25651890A JP H0418089 A JPH0418089 A JP H0418089A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- substituted
- value
- 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.)
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Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 3
- 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 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 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 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000532 dioxanyl group Chemical group 0.000 claims abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000012769 display material Substances 0.000 abstract description 2
- 238000000034 method Methods 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
- 239000004973 liquid crystal related substance Substances 0.000 description 44
- 210000004027 cell Anatomy 0.000 description 20
- -1 phenyl ester Chemical class 0.000 description 13
- 239000012071 phase Substances 0.000 description 11
- 230000007704 transition Effects 0.000 description 8
- 239000004988 Nematic liquid crystal Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000005669 field effect Effects 0.000 description 3
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 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
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (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行用なエーテル結合
を有ずろハロゲン化フェニルノクロへキシルジオキサン
に関するしのである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a halogenated phenylnochlorohexyldioxane 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・ンヤット（Ｍ、５
ｃｈａｄｔ ）等 ＣＡＰＰＬＩＥＤ Ｐ）ＩＹＳ
ＩＣ３ＬＥ丁ＴＥＲ３１ｇ。M Nyat (M, 5) is a typical liquid crystal display cell.
chadt) etc. CAPPLIED P)IYS
IC3LE TER31g.
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・モート・セル
）またはジー・エイチ・バイルマイヤー（Ｇ、Ｈ，Ｈｅ
１ｌ −ｍｅｉｅｒ）等［ＰＲＯＣＥＥＤＩＮＧ ＯＦ
ＴＨＥ １．Ｅ、Ｅ、Ｅ、 ５６．１１６２〜１１７
１（１９６ｇ） ）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・モート・セル）また
はジー・エイチ・バイルマイヤー（Ｇ、ＨＨｅｉｌｍｅ
ｉｅｒ）等［：ＡＰＰＬＩＥＤ ＰＨＹＳＩＣ３ＬＥＴ
ＴＥＲ３１３，９１（１９６ｇ））あるいはデイ−・エ
ル・ホワイト（Ｄ、Ｌ。127-128 (1971)] or the field effect cell proposed by G.H.
1l-meier) etc. [PROCEEDING OF
THE 1. E, E, E, 56.1162-117
1 (196g)) or the dynamic scattering moat cell proposed by G.H.
ier) etc.[:APPLIED PHYSIC3LET
TER313,91 (196g)) or D.L.White (D,L.
Ｗｈｉｔｅ）等［ＪＯＵＲＮＡＬ ＯＦ ＡＰＩ’ＬＩ
ＥＤ ＰＨＹＳＩＣ３４５，４７１８（１９７４）］に
よって提案されたゲスト・ホスト型セルなどがある。White) etc. [JOURNAL OF API'LI
ED PHYSIC 345, 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。Among these liquid crystal display cells, the one currently mainstream is a TN type cell, which is a type of field effect cell.
この１’ Ｎ型セルにおいては、ノー・バウワー（Ｇ。In this 1' N type cell, there is no bower (G.
Ｂａｕｅｒ）ｉ Ｍｏ１．Ｃｒｙｓｔ、 Ｌｉｑ、 Ｃ
ｒｙｓｔ、 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＄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かあ
る。実用的に使用される液晶表示セルでは、Δｎ−ｄの
値か０．５．１．０．１．６または２，２のいずれかに
設定されている。Bauer) i Mo1. Cryst, Liq, C
ryst, 63.45 (1981)], the refractive index of the liquid crystal material filled into the cell is adjusted to prevent the occurrence of dry streaks on the cell surface, which can impair the appearance of the cell. It is necessary to set the product of the anisotropy Δn and the thickness d (μm) of the liquid crystal layer in the cell to a certain value. In practically used liquid crystal display cells, the value of Δn-d is set to either 0.5.1.0.1.6 or 2.2.
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１０
．１６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。Normally, when the value of Δn-d is set to 0.5, the viewing angle characteristics are improved, and the value of Δn-d is set to 10.
．． When set to 16 or 2.2, the contrast from the front is improved.
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、△ｎ−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２２に設
定するのが普通である。Therefore, in the case of a liquid crystal display cell that emphasizes viewing angle characteristics that are easy to see from any direction, the value of △n-d should be set to 0.5,
Particularly in the case of a liquid crystal display cell in which emphasis is placed on contrast from the front, the value of Δn-d is usually set to 1, 0.1.6, or 22.
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〜ＩＯμｍの範囲内で設定さ
れるため、△ｎ−ｄの値を０５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
．０．１６または２２に設定する場合は、逆にΔｎの値
の大きな液晶材料かＺ・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
△ｎの値か大きい液晶材料か必要とされる。On the other hand, the thickness d of the liquid crystal layer in practically used liquid crystal display cells is usually set within the range of 6 to IO μm, so when setting the value of Δn−d to 05, Δn
A liquid crystal material with a small value of is required, and the value of Δn-d is reduced to 1.
．． When setting it to 0.16 or 22, on the other hand, a liquid crystal material with a large value of Δn is required. As described above, depending on the display characteristics of the liquid crystal display cell, a liquid crystal material with a small value of Δn and a liquid crystal material with a large value of Δn are required.
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、△ε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 addition, in TN-type cells, the dielectric anisotropy Δε of the mixed liquid crystal must be positive, so a nematic liquid crystal compound with a large Δε value, a low threshold voltage, and the ability to be driven at low voltage is required. It is said that
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。The problem to be solved by the present invention is that the value of Δn is small;
The object of the present invention is to provide a novel nematic liquid crystal compound having a large value of Δε and a low threshold voltage.
本発明は、上記課脛を解決するために、下記−般式（Ｉ
）で表される化合物を提供する。In order to solve the above problems, the present invention provides the following general formula (I
) is provided.
〔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ｌ−５の整数を表し、Ｘはフン素原子または塩
素原子を表し、Ｙは水素原子まｆコはフッ素原子を表し
、ノ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。〕
一般般式１）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かできる。[In the formula, R represents a linear alkyl group having 1 to 7 carbon atoms, n represents an integer of 1-5, X represents a fluorine atom or a chlorine atom, Y is a hydrogen atom, and It represents a fluorine atom, and the nooxane ring and cyclohexane ring have a trans configuration. ] The compound represented by general formula 1) can be produced according to the scheme shown below.
■
このスキームは、式（Ｕ）と式（１）の化合物をトルエ
ン中て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。(2) In this scheme, the compounds of formula (U) and formula (1) are reacted in toluene in the presence of an acidic catalyst such as p-toluenesulfonic acid at reflux temperature and dehydrated.
一般式（１）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
することかでき、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 (1) is a nematic liquid crystal compound having positive dielectric anisotropy, and therefore, for example, it can be used as a mixture with another nematic liquid crystal compound having negative dielectric anisotropy. It can be used as a material for dynamic light scattering type display cells, and it can also be used as a material for field effect type display cells in a mixture with other nematic liquid crystal compounds having positive or negative dielectric constant anisotropy. be able to.
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、９、香酸４′
−置換フェニルエステノ呟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ホニルオキシ）安息香
酸４′〜置換フエニルエステル、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−置換シクロヘキレル）安息香酸４′ −置換シク
ロへキシルエステノ呟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−置換ヒフェニル４′
−置換シクロヘキサン、２−（４−置換フェニル）−
５−置換ビリミジンなとを挙げることかできる。Preferred representative examples of other nematic liquid crystal compounds that can be used in combination with the liquid crystal compound of the present invention represented by general formula (I) include 4-substituted ammonium, 9, fragrant 4'
-substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-substituted biphenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-substituted phenyl ester,
-(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, 4-substituted phenyl to 4'-substituted cyclohexane, 4-
Substituted 4″-substituted terphenyl, 4-substituted hyphenyl 4′
-Substituted cyclohexane, 2-(4-substituted phenyl)-
Mention may be made of 5-substituted pyrimidine.
（実施例１）
式ＣＨ−０（ＣＨ２） ｓ ＣＨ（ＣＨ−ＯＨ） ｔ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５０ｍ１およびり−トルエンスルホン酸・ｌ水和物
０．０４０ｇ（０，ＯＯ０２１ｍｏｌ）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、ついて乾燥した
後、トルエンを留去して粗生成物を得た。(Example 1) 3.1 g (0,021 mol) of a compound represented by the formula CH-0(CH2) s CH(CH-OH) t and 4.7 g (0,021 mol) of a compound represented by the formula After adding 50 ml of toluene and 0.040 g (0.0021 mol) of tri-toluenesulfonic acid/l hydrate, a dehydration reaction was carried out at reflux temperature for 3 hours while stirring these. After cooling to room temperature, the toluene layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried, and the toluene was distilled off to obtain a crude product.
これをンリカゲル力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 using phosphoric gel chromatography and then recrystallized from ethanol to obtain 3.8 g (0,011 mol) of the following compound. Yield is 52
%Met.
この液晶化合物の相転移温度は、７１℃（Ｃ−Ｓ）、７
７°Ｃ（Ｓ二Ｎ）、９５℃（Ｎ：： Ｉ）であった。The phase transition temperature of this liquid crystal compound is 71°C (C-S), 7
The temperatures were 7°C (S2N) and 95°C (N::I).
（実施例２） 上記実施例１と同様にして下記化合物を得た。(Example 2) The following compound was obtained in the same manner as in Example 1 above.
収率は６２％であった。The yield was 62%.
この液晶化合物の相転移温度は、１０７℃（Ｃ−Ｎ）、
１２３°Ｃ（１１，：Ｉ）であった。The phase transition temperature of this liquid crystal compound is 107°C (CN),
The temperature was 123°C (11,:I).
（実施例３） 上記実施例Ｉと同様にして下記化合物を得た。(Example 3) The following compound was obtained in the same manner as in Example I above.
収率は３０％であった。The yield was 30%.
この液晶化合物の相転移温度は、８１’Ｃ（Ｃ−Ｎ）、
８７６Ｃ（Ｎ：： Ｉ）であった。The phase transition temperature of this liquid crystal compound is 81'C (CN),
876C(N::I).
（実施例４） 」二足実施例１と同様にして下記化合物を得た。(Example 4) The following compound was obtained in the same manner as in Example 1.
収率は２３％であった。The yield was 23%.
この液晶化合物の相転移温度は、９５℃（Ｃ−Ｎ）、１
２１’Ｃ（Ｎ：：ｌ）であった。The phase transition temperature of this liquid crystal compound is 95°C (CN), 1
21'C(N::l).
（実施例５） 上記実施例Ｉと同様にして下記化合物を得た。(Example 5) The following compound was obtained in the same manner as in Example I above.
収率は６１％であった。The yield was 61%.
この液晶化合物の相転移温度は、８０℃（Ｃ−Ｓ）、８
３°Ｃ（Ｓ二Ｎ）、１４２℃（Ｎ：： Ｉ）であった。The phase transition temperature of this liquid crystal compound is 80°C (C-S), 8
3°C (S2N), 142°C (N::I).
（実施例６） 上記実施例１と同様にして下記化合物を得た。(Example 6) The following compound was obtained in the same manner as in Example 1 above.
収率は１７％であった。The yield was 17%.
この液晶化合物の相転移温度は、８９℃（Ｃ−Ｎ）、１
３８°Ｃ（Ｎ：： Ｉ）であった。The phase transition temperature of this liquid crystal compound is 89°C (CN), 1
The temperature was 38°C (N::I).
（実施例７） 上記実施例１と同様にして下記化合物を得た。(Example 7) The following compound was obtained in the same manner as in Example 1 above.
収率は５６％であった。The yield was 56%.
この液晶化合物の相転移温度は、８２℃（Ｃ−Ｎ）、１
０６℃（Ｎ；：Ｉ）であっｆ二。The phase transition temperature of this liquid crystal compound is 82°C (CN), 1
06°C (N;:I) and f2.
上記実施例工ないし実施例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 each of the liquid crystal compounds of Examples to Example 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、■は等方性液体相をそれぞれ表わす。However, in Table 1, C is a crystalline phase, S is a smectic phase, and N
represents a nematic phase, and ■ represents an isotropic liquid phase.
（以下、余白）
第１表
（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か小さく、正のΔ
ε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ヒた。(Hereinafter, blank space) Table 1 (Application examples) 80 parts by weight of the following mixed liquid crystal (A), which is currently widely used as a base liquid crystal for nematic liquid crystal compositions, and each liquid crystal compound obtained in Examples 1 to 7 above. A liquid crystal composition was prepared by mixing with 20 parts by weight. In addition, as a comparative example, a liquid crystal compound having a similar chemical structure to that of Example 3, a small Δn, and a positive Δ
A liquid crystal composition consisting of 20 parts by weight of the following compound (a) having ε and 80 parts by weight of the following mixed liquid crystal was prepared.
これら各液晶組成物の屈折率異方性△ｎと誘電異方性Δ
ε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。Refractive index anisotropy Δn and dielectric anisotropy Δ of each of these liquid crystal compositions
ε and threshold voltage were measured. These results are shown in Table 2.
第 ２ 表
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。Table 2 The mixed liquid crystal (A) has the following composition.
２０重量％のｎ−Ｃ３Ｈ７１ｃＮ
１６重＠％のｎ−Ｃ３Ｈ＋＋（〉（）ＣＮ１６重量％の
ｎ −Ｃ７ｌ−（１５＄ ＣＮ８ ￥ ｔ％ｎ ｎ−Ｃ
５Ｈ７−ＩＢ）−Ｃ，ＯＯ％０Ｃ２Ｈ５８璽ｔ％のｎ−
Ｃ３Ｈ７Ｘ亘ＸＣ００Ｘ巨ｘＯ−ｎ−Ｃ＝ｓＨ９８ｇ量
％ｔｎ ｎ（４Ｈｇ ％ Ｃｏ罎０ＣＨ３８更量％）ｎ
−Ｃ４Ｈ９８ＣＯＯ−＠−０Ｃ２Ｈ５８重量％ ノｎ−
Ｃ５Ｈ＋ ＋ 舎ｃｏｏ（シ○ＣＨ３８重！（／６のｎ
−ＣｓＨ＋ ＋ ％ Ｃ００％ ＯＣ２Ｈ５また液晶
化合物（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。20wt% n-C3H71cN 16wt% n-C3H++ (〉()CN16wt% n-C7l-(15$ CN8 ￥t%n n-C
5H7-IB) -C,OO%0C2H58 t%n-
C3H7X Wataru
-C4H98COO-@-0C2H58% by weight non-
C5H+ + sha coo (shi○CH38 heavy! (/6 no n
-CsH+ + % C00% OC2H5 The liquid crystal compound (a) is a known compound (Japanese Patent Publication No. 44132/1983) represented by the following formula.
ｎ−Ｃ３Ｈ−ｒｑＦ
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Δ。n-C3H-rqF From Table 2, it can be seen that the conventionally known liquid crystal compound (a) is mixed with a mixed liquid crystal (
When mixed with A), the Δ of the mixed liquid crystal (A).
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て得た液晶化合物
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。On the other hand, when the liquid crystal compound obtained in Example 3 was mixed with the mixed liquid crystal (A), the mixed liquid crystal (A) It was confirmed that Δn was decreased, Δε was increased, and the threshold voltage was significantly lowered.
本発明の一般式（Ｉ）で表される化合物は、△ｎが小さ
く、かっ△ε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ろ
ことなく、Δεを増加させ、しきい値電圧を顕著に低下
させることかできる。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, which is currently widely used as a base liquid crystal. Alternatively, the threshold voltage can be significantly lowered by increasing Δε without increasing it much.
まに本発明の化合物は、構造類似の公知化合物と比へ、
その効果は顕著であり、視角特性に優れた低？’［工部
動可能なＴ入型液晶表示セルを作製するための１月とし
て極めてＧ用である。However, the compound of the present invention has a relatively similar structure to a known compound,
The effect is remarkable and the viewing angle characteristics are excellent. '[The engineering department is extremely suitable for G as January for producing a movable T-type liquid crystal display cell.
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). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) [In the formula, R represents a linear alkyl group having 1 to 7 carbon atoms, n represents an integer from 1 to 5, and X represents represents a fluorine atom or a chlorine atom, Y represents a hydrogen atom or a fluorine atom,
The dioxane ring and cyclohexane ring are in the trans configuration. ]
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 |
|---|---|---|---|
| JP9706090 | 1990-04-12 | ||
| JP2-97060 | 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 true JPH0418089A (en) | 1992-01-22 |
| JP3065094B2 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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009132927A (en) * | 1996-10-22 | 2009-06-18 | Chisso Corp | Dioxane derivative, liquid crystal composition containing the same, and liquid crystal display unit using the composition |
| 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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009132927A (en) * | 1996-10-22 | 2009-06-18 | Chisso Corp | Dioxane derivative, liquid crystal composition containing the same, and liquid crystal display unit using the composition |
| US10655065B2 (en) | 2016-08-01 | 2020-05-19 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3065094B2 (en) | 2000-07-12 |
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