JPH03223242A - Ether-based liquid crystal compound for reducing threshold voltage - Google Patents
Ether-based liquid crystal compound for reducing threshold voltageInfo
- Publication number
- JPH03223242A JPH03223242A JP23534290A JP23534290A JPH03223242A JP H03223242 A JPH03223242 A JP H03223242A JP 23534290 A JP23534290 A JP 23534290A JP 23534290 A JP23534290 A JP 23534290A JP H03223242 A JPH03223242 A JP H03223242A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- compound
- compound shown
- ether
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 6
- 230000001603 reducing effect Effects 0.000 title abstract 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 abstract 2
- 239000000126 substance Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 7
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 5
- 229910000564 Raney nickel Inorganic materials 0.000 abstract description 2
- 238000007239 Wittig reaction Methods 0.000 abstract description 2
- 239000012769 display material Substances 0.000 abstract description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004210 ether based solvent Substances 0.000 abstract 1
- -1 useful for 5TN-LCD Chemical class 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ZKTFZNPTAJIXMK-UHFFFAOYSA-N 2-cyclohexylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1CCCCC1 ZKTFZNPTAJIXMK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing 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、更に詳しくは液晶表示装
置に有用なエーテル系液晶化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to electro-optical display materials, and more particularly to ether-based liquid crystal compounds useful in liquid crystal display devices.
液晶表示セルの代表的なものにＴＮ−ＬＣＤ （ツィス
テッド、ネマチック液晶表示装置）があり、時計、電卓
、電子手帳、ポケットコンピュータ、ワードプロセッサ
、パーソナルコンビ二一夕などに使用されている。近年
、ＯＡ機器の処理情報の増加に伴い、一画面に表示され
る情報量が増大しており、従来のＴＮ−ＬＣＤではコン
トラスト及び視野角等の表示品位面から特にワードプロ
セッサ、パーソナルフンピユータなどの高時分割駆動の
要求に応えられなくなっている。A typical liquid crystal display cell is a TN-LCD (twisted nematic liquid crystal display), which is used in watches, calculators, electronic notebooks, pocket computers, word processors, personal computers, etc. In recent years, with the increase in information processed by OA equipment, the amount of information displayed on a single screen has increased, and conventional TN-LCDs are particularly suitable for word processors, personal computer computers, etc. due to display quality such as contrast and viewing angle. It is no longer possible to meet the demands of high time division drive.
このような状況の中で、シェファ−（Ｓｃｈｅｆｆｅｒ
）等［ＳＩＤ ’８５ Ｄｉｇｅｓｔ、 Ｐ１２０ （
１９８５） ）あるいは衣用等（ＳＩＤ ’８６ Ｄｉ
ｇｅｓｔ、 Ｐ１２２ （１９８６） ）によって５Ｔ
Ｎ（スーパー・ツィステッド・ネマチック）−ＬＣＤが
開発され、ワードプロセッサ、パーソナルコンピュータ
などの高情報処理用の表示に広（普及しはじめている。In this situation, Scheffer
) etc. [SID '85 Digest, P120 (
1985) ) or clothing etc. (SID '86 Di
5T by gest, P122 (1986))
N (super twisted nematic)-LCDs have been developed and are beginning to become widespread as displays for high information processing applications such as word processors and personal computers.
５ＴＮ−ＬＣＤに特に有用な液晶化合物の一つとして、
一般式
（式中、Ｒは直鎖状アルキル基を表わす。）で表わされ
る化合物（以下、ＰＣＩという。）が知られている。As one of the liquid crystal compounds particularly useful for 5TN-LCD,
A compound (hereinafter referred to as PCI) represented by the general formula (wherein R represents a linear alkyl group) is known.
ＰＣＨは正の誘電率の異方性を有するＰ形の液晶化合物
として有用であるが、誘電率の異方性（△ε）の値が約
＋１２〜１３とさほど大きくなく、現在汎用されている
ネマチック液晶材料に混合した際に、液晶材料のしきい
値電圧の低下効果が小さいという欠点を有している。PCH is useful as a P-type liquid crystal compound with positive dielectric constant anisotropy, but the value of dielectric constant anisotropy (Δε) is not very large, about +12 to 13, and it is currently widely used. It has the disadvantage that when mixed with a nematic liquid crystal material, the effect of lowering the threshold voltage of the liquid crystal material is small.
本発明が解決しようとする課題は、ＰＣＩと類似の化学
構造を有し、△εの値が大きく、現在汎用されているネ
マチック液晶材料に混合した際に、液晶材料のしきい値
電圧の低下効果が大きな化合物を提供することにある。The problem to be solved by the present invention is that it has a chemical structure similar to PCI, has a large value of Δε, and when mixed with the currently widely used nematic liquid crystal material, the threshold voltage of the liquid crystal material decreases. The objective is to provide compounds with great effects.
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２〜７の整数を表わし、す。）
で表わされる化合物を提供する。In order to solve the above-mentioned problems, the present invention is directed to the following: Provides compounds that can be used.
本発明に係わる一般式（Ｉ）で表わされる化合物は、次
の製造方法に従って製造することができる。The compound represented by general formula (I) according to the present invention can be produced according to the following production method.
（上記反応式におけるＲ及びｎは、 各々一般式 （） におけるＲ及びｎと同様の意味をもつ。(R and n in the above reaction formula are Each general formula () has the same meaning as R and n in .
）
第１段階：式（ｎ）の化合物をｔ−ブチルメチルエーテ
ルの如きエーテル系溶媒中
で、アルコキシメチル−トリフェニ
ルホスホニウムブロマイドとの
Ｗｉｔｔｉｇ反応に付し、式（ｍ）の化合物を製造する
。) First step: Compound of formula (n) is subjected to Wittig reaction with alkoxymethyl-triphenylphosphonium bromide in an ethereal solvent such as t-butyl methyl ether to produce compound of formula (m).
第２段階二式（ｍ）の化合物を酢酸エチル中、ラネー・
ニッケルを触媒として接触
還元を行ない、式（ＴＶ）の化合物を
製造する。2nd step Compound of formula (m) was mixed with Raney in ethyl acetate.
Catalytic reduction is performed using nickel as a catalyst to produce a compound of formula (TV).
第３段階二式（ｒＶ）の化合物をジメチルホルムアミド
の如き塩基性溶媒中でシアン
化第−銅と反応させて、式（Ｉ）の
化合物を製造する。Step 3: A compound of formula (rV) is reacted with cupric cyanide in a basic solvent such as dimethylformamide to produce a compound of formula (I).
斯くして製造された本発明に係わる一般式（１）で表わ
される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 the compounds represented by the general formula (1) according to the present invention thus produced.
第
１
表
（表中、Ｃは結晶相、Ｎはネマチック相、Ｉは等方性液
体相を各々表わす。）
一般式（１）の化合物と混合して使用することのできる
・・好ましい液晶化合物の代表例としては、例えば、４
−置換安息香酸４′−置換フェニルエステル、４−置換
シクロへ牛サンカルボン酸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’−ｉｔ換ピフェ
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−ｆｌ置換シクロヘキシル安息香酸
４′−置換シクロへ牛シルエステル、４−置換４′−置
換ピフェニル、４−置換フェニル４′−置換シクロへ牛
サン、４−置換４′−置換ターフェニル、４−置換ピフ
ェニル４′−置換シクロヘキサン、２− （４−１１換
フエニル）−５−置換ピリミジンなどを挙げることがで
きる。Table 1 (In the table, C represents a crystalline phase, N represents a nematic phase, and I represents an isotropic liquid phase.) Preferred liquid crystal compounds that can be used in combination with the compound of general formula (1) As a representative example, for example, 4
-substituted benzoic acid 4'-substituted phenyl ester, 4-substituted cyclohexancarboxylic acid 4'-substituted phenyl ester,
4-substituted cyclohexanecarboxylic acid 4'-it-substituted piphenyl ester, 4(4-substituted cyclohexanecarbonyloxy)benzoic acid 4'-substituted phenyl ester, 4-(
4-substituted cyclohexylbenzoic acid 4'-substituted phenyl ester, 4-(4-fl substituted cyclohexylbenzoic acid 4'-substituted cyclohexyl ester, 4-substituted 4'-substituted piphenyl, 4-substituted phenyl 4'- Examples include substituted cyclohexane, 4-substituted 4'-substituted terphenyl, 4-substituted piphenyl, 4'-substituted cyclohexane, and 2-(4-11 substituted phenyl)-5-substituted pyrimidine.
第２表はネマチック液晶材料として現在汎用されている
混合液晶（Ａ）の７０重量％と一般式（Ｉ）で表わされ
る化合物のＮｏ １及びＮｎ２の化合物の各々３０重量
％から成る混合液晶の誘電率の異方性（△ε）としきい
値電圧（ｖ ｔｈ）を掲示し、比較のために混合液晶（
Ａ）自体のへεと、混合液晶（Ａ）の７０重量％と、一
般式（１）で表わされる化合物と類似構造を有する式（
ａ）の化合物及び式（ｂ）の化合物の各々３０重量％か
ら成る混合液晶の△εとｖｔｈを掲示したものである。Table 2 shows the dielectric properties of a mixed liquid crystal consisting of 70% by weight of mixed liquid crystal (A), which is currently widely used as a nematic liquid crystal material, and 30% by weight each of compounds No. 1 and Nn2 of the general formula (I). The rate anisotropy (△ε) and threshold voltage (v th) are displayed, and the mixed liquid crystal (
A) itself, 70% by weight of the mixed liquid crystal (A), and a compound having a structure similar to that of the compound represented by the general formula (1) (
Δε and vth of a mixed liquid crystal containing 30% by weight of each of the compound a) and the compound of formula (b) are shown.
尚、混合液晶（Ａ）は、 １６．６重量％の １６．６重量％の １６．６重量％の １６．６重量％の ６ ６重量％の 及び１６．６重量％の から成るものであり、 式（ａ）及び式（ｂ）の化合物は、 各々次式で表わされる化合物である。In addition, the mixed liquid crystal (A) is 16.6% by weight 16.6% by weight 16.6% by weight 16.6% by weight 6 6% by weight and 16.6% by weight It consists of The compounds of formula (a) and formula (b) are Each compound is represented by the following formula.
第
表
第２表に掲示したデータから、一般式（１）で表わされ
る化合物は、負の誘電率の異方性を有する混合液晶（Ａ
）に加えた時に、誘電率の異方性を増加させ、しきい値
電圧を低下させる効果を有することが理解できる。構造
類似で一般的に広く用いられている式（ａ）の化合物を
混合液晶（Ａ）に加えた時と比較すると、誘電率の異方
性も大きく、しきい値電圧が顕著に低いことが明確であ
る。From the data posted in Table 2, it can be seen that the compound represented by the general formula (1) is a mixed liquid crystal (A
), it can be seen that it has the effect of increasing the anisotropy of the dielectric constant and lowering the threshold voltage. Compared to when the compound of formula (a), which has a similar structure and is widely used, is added to the mixed liquid crystal (A), the anisotropy of the dielectric constant is large and the threshold voltage is significantly lower. It is clear.
本発明が容易に類推できないことは一般式（１）で表わ
される化合物と類似の構造を有する式（ｂ）の化合物の
しきい値電圧の低下効果が、本発明の化合物Ｎｏ １及
びＮＱ ２よりも顕著に小さいばかりでなく、式（ａ）
の化合物よりも小さいことからも理解できる。What is not easily analogous to the present invention is that the threshold voltage lowering effect of the compound of formula (b) having a structure similar to that of the compound represented by general formula (1) is greater than that of compounds No. 1 and NQ 2 of the present invention. is not only significantly smaller, but also equation (a)
This can be understood from the fact that it is smaller than the compound.
［実施例コ
実施例１
３０、２ｇ （０，０７５モル）をｔ−ブチルメチルエ
ーテル１００ｍ１に加え、−１０℃で攪拌下、カリウム
−ｔ−ブトキサイド９ｇ （０，０８モル）で処理し、
同温度で１０分間攪拌した後、更に室温で１時間攪拌し
た。[Example 1 30.2 g (0.075 mol) were added to 100 ml of t-butyl methyl ether and treated with 9 g (0.08 mol) of potassium t-butoxide while stirring at -10°C.
After stirring at the same temperature for 10 minutes, the mixture was further stirred at room temperature for 1 hour.
次いで反応混合物を一５°Ｃに冷却し、テトラヒドロフ
ラン２０ｍ１に式
を溶解した溶液を５分間かけて滴下した後、室温で１時
間反応させた。反応終了後、反応混合物に水４００ｍ１
を加え、酢酸エチル１００ｍ１で３回抽出し、有機層を
水洗、乾燥した後、溶媒を減圧留去した。The reaction mixture was then cooled to -5°C, and a solution of the formula dissolved in 20 ml of tetrahydrofuran was added dropwise over 5 minutes, followed by reaction at room temperature for 1 hour. After the reaction is complete, add 400ml of water to the reaction mixture.
was added and extracted three times with 100 ml of ethyl acetate. The organic layer was washed with water and dried, and then the solvent was distilled off under reduced pressure.
得られた残渣をシリカゲルカラムクロマトグラフィー（
展開溶媒ｎ−へキサン：トルエン＝１：１）を用いて、
下記化合物８．２ｇ （０，０２５モル）を分離した。The resulting residue was subjected to silica gel column chromatography (
Using the developing solvent n-hexane:toluene=1:1),
8.2 g (0,025 mol) of the following compound were isolated.
次に、この化合物を酢酸エチル３００ｍ１に溶解し、触
媒としてラネー・ニッケル１ｇを加え、オートクレーブ
中、水素圧５ｋｇ／ｃｍ’で接触還元した。Next, this compound was dissolved in 300 ml of ethyl acetate, 1 g of Raney nickel was added as a catalyst, and catalytic reduction was carried out in an autoclave at a hydrogen pressure of 5 kg/cm'.
反応終了後、触媒を濾別し、溶媒を減圧留去して、下記
化合物７．８ｇ （０，０２４モル）を得た。After the reaction was completed, the catalyst was filtered off and the solvent was distilled off under reduced pressure to obtain 7.8 g (0,024 mol) of the following compound.
次に上記化合物７．８ｇ （０，０２４モル）をジメチ
ルホルムアミド８０１に溶解し、この溶液にシアン化第
−銅３．９ｇ （０，０４３モル）を加え、４時間加熱
還流した。反応終了後、アンモニア水１００ｍ１を加え
た後、酢酸エチルで抽出した。抽出液を水洗、乾燥した
後、溶媒を減圧留去して得た残渣をエタノールから再結
晶させて精製して、下記化合物４．５ｇ（０，０１６モ
ル）を得た。Next, 7.8 g (0,024 mol) of the above compound was dissolved in dimethylformamide 801, and 3.9 g (0,043 mol) of cupric cyanide was added to this solution, followed by heating under reflux for 4 hours. After the reaction was completed, 100 ml of aqueous ammonia was added, followed by extraction with ethyl acetate. After washing the extract with water and drying, the solvent was distilled off under reduced pressure, and the resulting residue was purified by recrystallization from ethanol to obtain 4.5 g (0,016 mol) of the following compound.
相転移温度 ４１°Ｃ（Ｃ→工） １０°Ｃ（Ｉｅ２Ｎ） 実施例２ 実施例１と同様にして下記化合物を得た。Phase transition temperature 41°C (C → engineering) 10°C (Ie2N) Example 2 The following compound was obtained in the same manner as in Example 1.
相転移温度 ４５°Ｃ（Ｃ−１）
１２９Ｃ（Ｉ、＋Ｎ）
〔発明の効果〕
本発明に係わる一般式（Ｉ）で表わされる化合物は、Ｐ
ＣＨと類似の化学構造をもち、ＰＣＨのしきい値電圧の
低下効果が小さいという欠点を補ない、しかもＰＣＨよ
りも誘電率の異方性が大きい化合物である。Phase transition temperature 45°C (C-1) 129C (I, +N) [Effects of the invention] The compound represented by the general formula (I) according to the present invention is P
It is a compound that has a chemical structure similar to CH, compensates for the drawback of PCH that the effect of lowering the threshold voltage is small, and has a larger dielectric anisotropy than PCH.
従って、本発明に係わる一般式（１）で表わされる化合
物は、低電圧駆動及び高時分割駆動に優れたＴＮ−ＬＣ
Ｄあるいは５ＴＮ−ＬＣＤ用の材料として極めて有用で
ある。Therefore, the compound represented by the general formula (1) according to the present invention is a TN-LC with excellent low voltage drive and high time division drive.
It is extremely useful as a material for D or 5TN-LCD.
Claims (1)
わし、ｎは２〜７の整数を表わし、 ▲数式、化学式、表等があります▼はトランス配置のシ
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 2 to 7. , ▲There are mathematical formulas, chemical formulas, tables, etc. ▼ represents a cyclohexane ring in the trans configuration.) A compound represented by.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1-312864 | 1989-12-01 | ||
| JP31286489 | 1989-12-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03223242A true JPH03223242A (en) | 1991-10-02 |
| JP2874308B2 JP2874308B2 (en) | 1999-03-24 |
Family
ID=18034358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23534290A Expired - Lifetime JP2874308B2 (en) | 1989-12-01 | 1990-09-05 | Ether-based liquid crystal compound for lowering threshold voltage |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2874308B2 (en) |
-
1990
- 1990-09-05 JP JP23534290A patent/JP2874308B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2874308B2 (en) | 1999-03-24 |
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