JPH03220148A - Tricyclic fluorocompound having ether bond - Google Patents
Tricyclic fluorocompound having ether bondInfo
- Publication number
- JPH03220148A JPH03220148A JP1548190A JP1548190A JPH03220148A JP H03220148 A JPH03220148 A JP H03220148A JP 1548190 A JP1548190 A JP 1548190A JP 1548190 A JP1548190 A JP 1548190A JP H03220148 A JPH03220148 A JP H03220148A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- low
- equatorial
- 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.)
- Granted
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 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 4
- 239000000126 substance Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 26
- 239000000463 material Substances 0.000 abstract description 9
- 239000003054 catalyst Substances 0.000 abstract description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 239000012769 display material Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
- 230000000007 visual effect Effects 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- -1 4-substituted benzoic acid Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000005669 field effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- LHNYBDSPFVTMOA-UHFFFAOYSA-N 2,3-dicyclohexylbenzoic acid Chemical class C1CCCCC1C=1C(C(=O)O)=CC=CC=1C1CCCCC1 LHNYBDSPFVTMOA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 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
- 230000007423 decrease Effects 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring 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〕
配置のシ
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
を有するフッ素系３環式化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] Configuration The present invention relates to a fluorine-based tricyclic compound having an ether bond 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、５
ｃｈａｄｔ ）等（ＡＰＰＬＩＥＤ ＰＨＹＳＩＣＳ
ＬＥＴＴＥＲ５上工、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、Ｈ，Ｈｅｉｌｍｅｉｅｒ ）等（ＰＲ
ＯＣＲＥＤＩＮＧ ＯＦ ＴＨＥ Ｉ。M-Shut (M, 5) is a typical liquid crystal display cell.
chadt) etc. (APPLIED PHYSICS
LETTER5 Joukou, 127-128 (1971)
) proposed field-effect cell (field-effect cell)
effect mode cell) or G.H. Heilmeier (PR
OCREDING OF THE I.
Ｅ、Ｅ、Ｅ、 ５６１１６２〜１１７１ （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）又はジー・エイチ・バ
イルマイヤー（Ｇ、Ｈ，）Ｉｅｉｌｍｅｉｅｒ ）等（
ＡＰＰＬＩＥＤＰＨＹＳＩＣ５ＬＥＴＴＥＲＳ エム
、 ９１ （１９６８） ）あるいはデイ−・エル・ホ
ワイト（Ｄ、ＬＪｈｉｔｅ ）等［ＪＯＵＲＮＡＬ Ｏ
Ｆ ＡＰＰＬＩＥＤ ＰＨＹＳＩＣＳ ４ｆｉ 、 ４
７１８（１９７４） ］によって提案されたゲスト・ホ
スト型セルなどがある。E, E, E, 561162-1171 (1968)
) or the dynamic scattering mode cell proposed by G. H. Beilmeier (G.H.) et al.
APPLIEDPHYSIC5LETTERS M, 91 (1968)) or D, LJhite, etc. [JOURNAL O
F APPLIED PHYSICS 4fi, 4
718 (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ＴＮ型セルにおいては、Ｇ、Ｂａｕｅｒによって門
ｏ１． Ｃｒｙｓｔ、 Ｌｉｑ、 Ｃｒｙｓｔ、
６ ３． ４ ５ （１９８１） に報
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（Δｉ）とセルにおける液
晶層の厚さ（ｄ） μｍの積を成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、Δ
ｎ −ｄの値が０．５．１．０゜１．６又は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、視角特性が良くなるという特徴
があり、Δｎ −ｄの値を１．０１．６又は２．２に
設定した場合、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又は２．２に設定するのが普通である。In this TN type cell, gate o1. Cryst, Liq, Cryst,
6 3. 4 5 (1981), the refractive index anisotropy ( It is necessary to set the product of Δi) and the thickness (d) μm of the liquid crystal layer in the cell to a specific value. In practically used liquid crystal display cells, Δ
The value of nd is set to either 0.5.1.0°1.6 or 2.2. Normally, when the value of Δn -d is set to 0.5, the viewing angle characteristics are improved, and when the value of Δn -d is set to 1.01.6 or 2.2, the contrast from the front is improved. It has the characteristic that it improves. 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 Δn - d is set to 0.5, and in the case of a liquid crystal display cell that emphasizes contrast from the front, the value of Δn - d is set to 0.5. The value of 1.0.1
．． It is common to set it to 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
晶層の厚さは、通常、６〜１０μｍの限定された範囲で
成る値に設定されるため、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又は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, the thickness of the liquid crystal layer in practically used liquid crystal display cells is usually set within a limited range of 6 to 10 μm, so the value of Δn - d is set to 0.5. When setting the Δn-d value to 1.0, 1.6, or 2.2, a liquid crystal material with a large Δn value is required. becomes. In this way, Δn depends 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、混合液晶の誘電率の異方性
（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 addition, in a TN cell, the dielectric constant 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 a low voltage is used. is necessary.
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.
〔課題を解決するための手段］
本発明は、上記課題を解決するために、一般式
（式中、Ｒは炭素原子数１〜５の直鎖状アルキル基を表
わし、ｎは４〜８の整数を表わし、Ｘは水ランス（エカ
トリアル−エカトリアル）配置のシクロヘキサン環を表
わす。）
で表わされる化合物を提供する。[Means for Solving the Problems] In order to solve the above-mentioned problems, the present invention provides a general formula (wherein R represents a linear alkyl group having 1 to 5 carbon atoms, and n represents 4 to 8 carbon atoms). is an integer, and X represents a cyclohexane ring in a water lance (equatorial-equatorial) configuration.
本発明に係わる式（１）の化合物は次の製造方法に従っ
て製造することができる。The compound of formula (1) according to the present invention can be produced according to the following production method.
〔上記反応式中、Ｒは炭素原子数１〜５の直鎖状アルキ
ル基を表わし、ｎは４〜８の整数を表わし、Ｘは水素原
子又はフッ素原子を表わし、アル）のシクロヘキサン環
を表わす。〕第１段階−式（■）の化合物をテトラヒド
ロフラン中でマグネシウム末と反応させて、
式（ＩＩＩ）の如きグリニヤール試薬を製造する。[In the above reaction formula, R represents a linear alkyl group having 1 to 5 carbon atoms, n represents an integer of 4 to 8, X represents a hydrogen atom or a fluorine atom, and represents a cyclohexane ring of . [Step 1] A compound of formula (■) is reacted with magnesium powder in tetrahydrofuran to prepare a Grignard reagent such as formula (III).
第２段階−式（Ｉ［）の化合物にテトラヒドロフラン中
で式（ＩＶ）の化合物を反応させて、式（Ｖ）の化合物
を製造する。Step 2 - A compound of formula (I[) is reacted with a compound of formula (IV) in tetrahydrofuran to produce a compound of formula (V).
第３段階−式（Ｖ）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存
在下、脱水反応に付し、式（Ｖｌ）の化合物を製造する
。Third step - The compound of formula (V) is subjected to a dehydration reaction in toluene in the presence of an acidic catalyst such as p-toluenesulfonic acid to produce a compound of formula (Vl).
第４段階−式（Ｖｌ）の化合物をエタノールの如きアル
コール中でラネーニッケルを触媒
として、接触還元を行ない、式（１）
の化合物を製造する。Step 4 - Catalytic reduction of the compound of formula (Vl) in an alcohol such as ethanol using Raney nickel as a catalyst produces a compound of formula (1).
斯くして製造された式（１）の代表的な化合物の相転移
温度を第１表に掲げる。Table 1 lists the phase transition temperatures of representative compounds of formula (1) thus produced.
第 １ 表
（表中、Ｃは結晶相、Ｎはネマチック相、ｌは等方性液
体相を夫り表わす、）′
本発明に係わる式（Ｉ）の化合物は、正の誘電率の異方
性を有するネマチック液晶化合物であり、従って例えば
、負の誘電率の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、また正又は負の誘電率の異方性
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
。Table 1 (In the table, C represents a crystalline phase, N represents a nematic phase, and l represents an isotropic liquid phase). Therefore, it can be used, for example, as a material for dynamic light scattering type display cells in a mixture with other nematic liquid crystal compounds having negative dielectric constant anisotropy, and It can be used as a material for field-effect display cells in the form of a mixture with other nematic liquid crystal compounds having positive or negative dielectric constant anisotropy.
このように、式（Ｉ）の化合物と混合して使用すること
のできる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’−ｆｌｌｌｋフェニルエステル、４
−ｉ！換ジシクロ牛サンカルボン酸４′−１換ビフェニ
ルエステ／Ｌ＜、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
−（４−１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−ｉｆ換ジ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−置換フェニルー４′−置換シク
ロヘキサン、４−置換４”−’１ＷＡ９−フェニル、４
−置換ビフェニル４１−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。Thus, preferred representative examples which can be used in admixture with compounds of formula (I) include, for example, 4-substituted benzoic acid 4'-substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-flllk phenyl ester. , 4
-i! 4-(4-Substituted cyclohexanecarbonyloxy)benzoic acid 4'-substituted phenyl ester, 4
-(4-1 substituted cyclohexyl)benzoic acid 4'-substituted phenyl ester, 4-(4-if substituted dicyclohexylbenzoic acid 4'-substituted cyclohexyl ester, 4-substituted 4'
-Substituted biphenyl, 4-substituted phenyl-4'-substituted cyclohexane, 4-substituted 4''-'1WA9-phenyl, 4
-substituted biphenyl 41-substituted cyclohexane, 2-(4
-substituted phenyl)-5=substituted pyrimidine, and the like.
第２表はネマチック液晶材料として現在母体液晶として
汎用されている混合液晶（Ａ）の８０重量％と第１表に
示した式（１）の化合物Ｎｃｈｌと患ｌと類似化学構造
を有し、Δｎが低く正のΔεを有する化合物（ａ）の各
々の２０重量％とから成る各混合液晶について測定され
たΔｎとΔεとしきい値電圧を掲示し、比較のために混
合液晶（Ａ）自体について測定されたΔｎとΔεとしき
い値電圧を掲示したものである。Table 2 shows 80% by weight of mixed liquid crystal (A), which is currently widely used as a base liquid crystal as a nematic liquid crystal material, and has chemical structures similar to those of the compounds Nchl and Chl of formula (1) shown in Table 1. The Δn, Δε, and threshold voltage measured for each mixed liquid crystal consisting of 20% by weight of each compound (a) having a low Δn and positive Δε are posted, and for comparison, the mixed liquid crystal (A) itself is shown. The measured Δn, Δε, and threshold voltage are displayed.
尚、混合液晶（Ａ）は の公知化合物（特公昭６３−４４１３２号）である。In addition, the mixed liquid crystal (A) It is a known compound (Japanese Patent Publication No. 63-44132).
第 ２ 表
及び
から成るものであり、
化合物（ａ）は式
第２表に掲示したデータから、式（Ｉ）の化合物は混合
液晶のΔｎを低下させ、Δεを上昇し、しきい値電圧を
顕著に低下せしめ得ることが理解できる。本発明の効果
は、従来公知の化合物（ａ）が混合液晶のΔｎを上昇し
、Δεを低下させ、しきい値電圧を著しく上昇させてし
まうことからも明確である。Compound (a) has the formula From the data posted in Table 2, the compound of formula (I) lowers Δn, increases Δε, and increases the threshold voltage of the mixed liquid crystal. It can be seen that this can be significantly reduced. The effects of the present invention are clear from the fact that the conventionally known compound (a) increases Δn, decreases Δε, and significantly increases the threshold voltage of the mixed liquid crystal.
実施例１
マグネシウム末１．５ ｇ （０，０６モル）を乾燥テ
トラヒドロフラン１０ｍｆに加え、触媒量のジブコムエ
チレンで活性化した後、３０ ’Ｃ以下で、式を乾燥テ
トラヒドロフラン２５ｎｌに希釈した溶液を滴下した。Example 1 1.5 g (0.06 mol) of magnesium powder was added to 10 mf of dry tetrahydrofuran and after activation with a catalytic amount of dibucom ethylene, a solution of the formula diluted in 25 nl of dry tetrahydrofuran was added at below 30'C. dripped.
滴下終了後、０．５時間同温度で攪拌を続けた。次いで
、この反応液に、式上記化合物をトルエン２５０ｍｊ２
に溶解し、Ｐトルエンスルホン酸１ｇを加え４時間除水
装置で除水しながら、加熱還流した。After the dropwise addition was completed, stirring was continued at the same temperature for 0.5 hour. Next, to this reaction solution, add the compound of the above formula to 250 mj2 of toluene.
1 g of P-toluenesulfonic acid was added thereto, and the mixture was heated under reflux for 4 hours while removing water using a water removal device.
反応終了後、トルエン層を水洗、乾燥した後、溶媒を減
圧留去して得た残渣をエタノール１３０Ｉｌｌから再結
晶させて精製して、下記化合物１３．０ｇ （０，０３
５モル）を得た。After the reaction, the toluene layer was washed with water and dried, and the solvent was distilled off under reduced pressure. The resulting residue was purified by recrystallization from 130 Ill of ethanol to obtain 13.0 g of the following compound (0.03
5 mol) was obtained.
（０，０４５モル）を乾燥テトラヒドロフラン３０憔ｌ
に溶解した溶液を２５°Ｃ以下で滴下し、その後、室温
で３時間反応させた。(0,045 mol) in 30 liters of dry tetrahydrofuran
was added dropwise at a temperature below 25°C, and then reacted at room temperature for 3 hours.
反応終了後、反応液に９％塩酸５Ｑｔａ７！に加え、ト
ルエン１００ＩＩＮで３回抽出、水洗、乾燥した後、溶
媒を減圧留去し、下記化合物１５．２ ｇ（０，０３９
モル）を得た。After the reaction is complete, add 5Qta7! of 9% hydrochloric acid to the reaction solution. In addition, the following compound (15.2 g (0,039
mole) was obtained.
Ｈ
上記化合物をエタノール２５０ｍ１２に溶解し、ラネー
ニッケル１ｇを加えた後、室温下、水素圧５気圧で１５
時間接触還元した。反応終了後、触媒を除去した後、エ
タノールを減圧留去して得た残渣をｎ−ヘキサン８０ｏ
＋ｆから再結晶させて精製して、下記化合物８．５ｇ
（０，０２３モル）を得た。H The above compound was dissolved in 250 ml of ethanol, 1 g of Raney nickel was added, and the mixture was dissolved at room temperature under a hydrogen pressure of 5 atm.
Time contact reduction. After the reaction was completed, the catalyst was removed and the ethanol was distilled off under reduced pressure.
Recrystallize from +f and purify to obtain 8.5 g of the following compound.
(0,023 mol) was obtained.
転移温度 室温以下（Ｃ−→５）４０°Ｃ（Ｓ−
ヨＮ）
１０７°Ｃ（Ｎ；廿■）
〔発明の効果］
本発明に係わる式（１）の化合物は、Δｎが低く、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
を低下させ、Δεを上昇させ、しきい値電圧を低下させ
ることができる０本発明に係わる式（Ｉ）の化合物は、
構造類位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。Transition temperature Below room temperature (C-→5) 40°C (S-
YON) 107°C (N; 廿■) [Effects of the Invention] The compound of formula (1) according to the present invention has a low Δn and a low Δε
Since the Δn of the mixed liquid crystal is large, it is possible to reduce the
The compound of formula (I) according to the present invention is capable of lowering Δε, increasing Δε, and lowering the threshold voltage.
Its effect is remarkable compared to known compounds of similar structural rank.
It is extremely useful as a material for producing a TN-type liquid crystal display cell that has excellent viewing angle characteristics and can be driven at low voltage.
Claims (1)
わし、ｎは４〜８の整数を表わし、Ｘは水素原子又はフ
ッ素原子を表わし、▲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）配置のシク
ロヘキサン環を表わす。） で表わされる化合物。[Claims] 1. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R represents a linear alkyl group having 1 to 5 carbon atoms, and n represents an integer of 4 to 8. , X represents a hydrogen atom or a fluorine atom, ▲There are mathematical formulas, chemical formulas, tables, etc.▼
represents a cyclohexane ring in trans (equatorial-equatorial) configuration. ) A compound represented by
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1548190A JP2822530B2 (en) | 1990-01-25 | 1990-01-25 | Fluorine-based tricyclic compound having an ether bond |
| US07/557,336 US5068462A (en) | 1989-07-28 | 1990-07-26 | Fluorine-substituted compound containing ether bond and intermediate thereof |
| EP90114454A EP0415090B1 (en) | 1989-07-28 | 1990-07-27 | Fluorine-substituted compound containing ether bond and intermediate thereof |
| DE69006803T DE69006803T2 (en) | 1989-07-28 | 1990-07-27 | Fluorine-substituted compound containing ether linkage and intermediate therefor. |
| US07/709,842 US5166448A (en) | 1989-07-28 | 1991-06-04 | Intermediate for preparing fluorine-substituted compound containing ether bond |
| HK98104381A HK1005184A1 (en) | 1989-07-28 | 1998-05-21 | Fluorine-substituted compound containing ether bond and intermediate thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1548190A JP2822530B2 (en) | 1990-01-25 | 1990-01-25 | Fluorine-based tricyclic compound having an ether bond |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03220148A true JPH03220148A (en) | 1991-09-27 |
| JP2822530B2 JP2822530B2 (en) | 1998-11-11 |
Family
ID=11889984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1548190A Expired - Lifetime JP2822530B2 (en) | 1989-07-28 | 1990-01-25 | Fluorine-based tricyclic compound having an ether bond |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2822530B2 (en) |
-
1990
- 1990-01-25 JP JP1548190A patent/JP2822530B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2822530B2 (en) | 1998-11-11 |
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