JPS5811431B2 - optically active ester - Google Patents
optically active esterInfo
- Publication number
- JPS5811431B2 JPS5811431B2 JP228776A JP228776A JPS5811431B2 JP S5811431 B2 JPS5811431 B2 JP S5811431B2 JP 228776 A JP228776 A JP 228776A JP 228776 A JP228776 A JP 228776A JP S5811431 B2 JPS5811431 B2 JP S5811431B2
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- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- tnd
- crystal composition
- added
- 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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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、捩れた液晶配向をもつ液晶表示装置(いわゆ
るTwisted Nematic Di’5play
1以下TNDと略記する)に使用される正の誘電異方性
を有する液晶組成物の改良に使用する光学活性化合物に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a liquid crystal display device with twisted liquid crystal alignment (so-called Twisted Nematic Di'5play).
The present invention relates to an optically active compound used for improving liquid crystal compositions having positive dielectric anisotropy used in liquid crystal compositions (hereinafter abbreviated as TND).
更に詳しくは、TNDパネルに通常あられれる縞模様が
生成しない、外見の均一なTNDパネルの作成を容易に
する、光学活性体を含有するTND甲液晶組成物に使用
する光学活性化合物に関する。More specifically, the present invention relates to an optically active compound used in a TND liquid crystal composition containing an optically active substance, which facilitates the creation of a TND panel with a uniform appearance and which does not produce the striped pattern that normally occurs in TND panels.
TNDパネルに発生する縞模様は、液晶表示素子の外観
、見易さを損い、表示装置の市場価値を著るしく減少さ
せるものであるが、その発生の原因の一つは、液晶がセ
ル内で捩れる方向が左右一定しない場合に捩れる向きが
逆になった領域(通常これを&verse Twist
Domainと呼ぶ、以下これをRTDと略記する)
が生成しているためであることが知られている。The striped pattern that occurs on TND panels impairs the appearance and visibility of the liquid crystal display element, and significantly reduces the market value of the display device. One of the causes of this is that the liquid crystal is When the twisting direction is not constant on the left and right sides, the area where the twisting direction is reversed (usually called &verse Twist)
Domain (hereinafter abbreviated as RTD)
It is known that this is because it is generated.
捩れのむきを一方向に規制してRTDの生成を防ぐ方法
としてコレステリック化合物を少量添加する事が知られ
ている。It is known that a small amount of cholesteric compound is added as a method of controlling the twisting in one direction and preventing the generation of RTD.
そのコレステリック化合物としてはコレステリールノナ
エート(エレクトロニツクスレターズ(Electro
nics Letters)、9、P 130〜1(1
973))、コレステリールクロリド(同上誌、10、
P118〜20、(1974))等が知られている。The cholesteric compound is cholesteryl nonaate (Electronic Letters).
nics Letters), 9, P 130-1 (1
973)), cholesteryl chloride (ibid., 10,
P118-20, (1974)) and the like are known.
しかしこれ等のコレステロール誘導体は一般に知られて
いる様に化学的、光学的に比較的不安定な物質であるた
め、これらを添加するとTNDパネルの使用寿命に悪影
響がある。However, as is generally known, these cholesterol derivatives are chemically and optically relatively unstable substances, so their addition has an adverse effect on the service life of the TND panel.
従って化学的、光化学的に安定な、しかも同じ目的を達
成する事を可能にする様な化合物が望まれており特開昭
49−95882には、コレステロール誘導体の代りに
、光学活性を含有する次式の化合物(1)を使用するこ
とによりRTDの生成を抑制出来ることが報告されてい
る。Therefore, there is a need for a compound that is chemically and photochemically stable and that can achieve the same purpose. It has been reported that the production of RTD can be suppressed by using the compound (1) of the formula.
化合物(1)は、それ自身は液晶物質ではないが、化合
物(1)に類似する構造を有するシアノビフェニル液晶
に添加することより、化合物(1)の光学活性の故に、
液晶の捩れる方向も左又は右のうち一方向のみに規制さ
れるものと考えられる。Although compound (1) is not a liquid crystal substance itself, by adding it to cyanobiphenyl liquid crystal having a structure similar to compound (1), due to the optical activity of compound (1),
It is thought that the twisting direction of the liquid crystal is also restricted to only one of the left and right directions.
しかるにこの化合物(1)は合成経路が長く、製造が容
易でない。However, compound (1) requires a long synthetic route and is not easy to manufacture.
前記特開昭49−95882によれば化合物(1)は次
の経路で合成される。According to JP-A-49-95882, compound (1) is synthesized by the following route.
(同上実施例2及23)本発明者らは、より容易に製造
し得る光学活性化合物であり、かつ化学的光学的安定性
に於て優れている同じ目的を達成しつる化合物を探索し
た結果、次式(■)で示される新規な化合物が好適であ
る事を見出した。(Examples 2 and 23) The present inventors have searched for a compound that achieves the same purpose and is an optically active compound that can be produced more easily and has excellent chemical and optical stability. , it has been found that a novel compound represented by the following formula (■) is suitable.
化合物(II)は3つの反応の組み合せである次の反む
ルートによって製造できる。Compound (II) can be prepared by the following route, which is a combination of three reactions.
主原料の(−)活性アルコールは日本国内で容易に入手
しつる唯一の光学活性第1級アルコールである。The main raw material (-) active alcohol is the only optically active primary alcohol that is easily available in Japan.
他の主原料は市販のp−ヒドロキシ安息香酸とp−ジア
ノフェノールである。Other main raw materials are commercially available p-hydroxybenzoic acid and p-dianophenol.
化合物(■)は融点88〜89℃の無色針状結晶体で、
クロロホルム溶液中での比施光度は〔α〕2δ=+6.
1°である。Compound (■) is a colorless needle-like crystal with a melting point of 88-89°C.
The specific power in chloroform solution is [α]2δ=+6.
It is 1°.
又第1図の紫外線吸収スペクトルに示す様に化合物(I
I)は300μm以上の波長範囲に吸収を持たない。Furthermore, as shown in the ultraviolet absorption spectrum of Fig. 1, the compound (I
I) has no absorption in the wavelength range of 300 μm or more.
従って液晶セルのガラス板を透過する光は吸収しない故
、使用中光化学的反応の可能性はない。Therefore, since the light transmitted through the glass plate of the liquid crystal cell is not absorbed, there is no possibility of photochemical reaction during use.
化合物(II)は通常知られているすべての化合物タイ
プのTND用液晶に使用してすぐれたRTD消去効果を
示すことがわかった。Compound (II) was found to exhibit excellent RTD elimination effects when used in all known compound types of TND liquid crystals.
それらの液晶の代表的なものをグループ別に示すと次の
如くであるが、別にこれ等に限定されない。Typical liquid crystals are shown below by group, but the invention is not limited to these.
(1)p−アルキルオキシベンシリデンーメーアルキル
アニリン類よりなる負の誘電異方性を有するシッフ化合
物液晶に、p−アルキルオキシベンジリデン−p′−シ
アノアニリン、及び/又はp−アルキルベンジリデン−
p′−シアノアニリン及び/又はp−シアノベンジリデ
ン−p’−アルキルアニリンを溶解して得られるシッフ
化合物系のTND用液晶組成物。(1) p-alkyloxybenzylidene-p'-cyanoaniline and/or p-alkylbenzylidene-p'-cyanoaniline and/or p-alkylbenzylidene-
A Schiff compound-based TND liquid crystal composition obtained by dissolving p'-cyanoaniline and/or p-cyanobenzylidene-p'-alkylaniline.
(2)p−アルキルオキシベンジリデン−p−アルキル
アニリン類よりなるシッフ化合物液晶にアルキル安息香
酸p−シアノフェニルエステル及び/又はアルキルオキ
シ安息香酸p−シアノフェニルエステルを溶解して得ら
れるTND用液晶組成物。(2) A liquid crystal composition for TND obtained by dissolving alkylbenzoic acid p-cyanophenyl ester and/or alkyloxybenzoic acid p-cyanophenyl ester in a Schiff compound liquid crystal consisting of p-alkyloxybenzylidene-p-alkylanilines. thing.
(3)p−アルキルオキシベンジリデン−p′−シアノ
アニリン類、p−アルキルベンジリデン=p′−シアノ
アニリン類及びそれ等の混合物であるTND用液晶組成
物。(3) A liquid crystal composition for TND which is p-alkyloxybenzylidene-p'-cyanoaniline, p-alkylbenzylidene-p'-cyanoaniline, and a mixture thereof.
(4)p−アルキル−p′−シアノビフェニルとp−ア
ルキルオキシ−p′−シアノビフェニルよりなる混合液
晶組成物及び、これ等にp−アルキル−p′−シアノタ
ーフェニル、及び/又はp−アルキル−pl−ビフェニ
ルカルボン酸のシアノフェノールエステルを添加したT
ND用液晶組成物。(4) A mixed liquid crystal composition consisting of p-alkyl-p'-cyanobiphenyl and p-alkyloxy-p'-cyanobiphenyl, and p-alkyl-p'-cyanoterphenyl and/or p- T added with cyanophenol ester of alkyl-pl-biphenylcarboxylic acid
Liquid crystal composition for ND.
(5)アルキル安息香酸のシアノフェノールエステル及
びアルキルオキシ安息香酸のシアノフェニルエステルよ
りなるTND用液晶組成物。(5) A liquid crystal composition for TND comprising a cyanophenol ester of alkylbenzoic acid and a cyanophenyl ester of alkyloxybenzoic acid.
(6)p−アルキル−p′−アルキルオキシアゾキシベ
ンゼンにアルキルオキシ安息香酸のシアンフェノールエ
ステルを添加することにより得られるTND用液晶組成
物。(6) A liquid crystal composition for TND obtained by adding cyanphenol ester of alkyloxybenzoic acid to p-alkyl-p'-alkyloxyazoxybenzene.
(7)p及びp′位にアルキル基又はアルキルオキシ基
を持つフェニル安息香酸とp及びp“位にアルキル基又
はアルキルオキシ基を持つp−ベンゾイルオキシ安息香
酸フェニルとよりなる非シアノ系TND用液晶組成物。(7) For non-cyano TNDs consisting of phenylbenzoic acid having an alkyl group or alkyloxy group at the p and p' positions and phenyl p-benzoyloxybenzoate having an alkyl group or an alkyloxy group at the p and p' positions liquid crystal composition.
以上の各分類に属する液晶組成物に対して化合物(II
)を0.1〜3重量係添加すればRTD消去効果が極め
て顕著に現れる。For liquid crystal compositions belonging to each of the above categories, compounds (II
) is added in a weight ratio of 0.1 to 3, the RTD elimination effect becomes extremely noticeable.
これ以上を添加することは一般に不必要であり、基本と
なる液晶組成物の種類によっては過剰の添加によりかえ
って液晶表示パネルが全体的に淡い濁りを生じたり、低
温での長時間放置により化合物(II)が析出するなど
の好ましくない結果となる。It is generally unnecessary to add more than this, and depending on the type of the basic liquid crystal composition, adding too much may cause the liquid crystal display panel to become slightly cloudy, or if left for a long time at low temperatures, the compound ( This results in unfavorable results such as precipitation of II).
化合物(II)の最適添加量はその他製造しようとする
TNDパネルの液晶層の厚み及び電極ガラスのガラスの
表面特性により変動する。The optimum amount of compound (II) to be added varies depending on the thickness of the liquid crystal layer of the TND panel to be manufactured and the surface characteristics of the electrode glass.
液晶層の厚みを比較的厚くしたい場合には化合物(■)
の添加量は上記範囲の下限の方向で実験的に求めるのが
よく、反対に液晶層の比較的薄いTNDパネルを製造す
る場合には、上記範囲の上限の方向で実験的に求めるの
がよい。If you want to make the liquid crystal layer relatively thick, use a compound (■)
It is best to experimentally determine the amount of addition toward the lower limit of the above range.On the contrary, when manufacturing a TND panel with a relatively thin liquid crystal layer, it is better to experimentally determine the amount toward the upper limit of the above range. .
又電極ガラスの表面特性は、電極ガラスの製造方法即ち
蒸着物質の鍾類、蒸着方法、蒸着条件、表面処理方法、
熱履歴等によって微妙に変動し、かつ表面特性と液晶の
配向の関係も理論的に解明されていないので、実験的に
化合物(II)の最適添加量を決定するのがよい。In addition, the surface characteristics of the electrode glass depend on the manufacturing method of the electrode glass, that is, the type of vapor deposition material, the vapor deposition method, the vapor deposition conditions, the surface treatment method,
Since it varies slightly depending on thermal history and the like, and the relationship between surface properties and liquid crystal orientation has not been theoretically elucidated, it is best to determine the optimum amount of compound (II) to be added experimentally.
しかし普通のTNDパネルは通常数ミクロンないし20
ミクロン程度の厚さの液晶層を作るように製造されるの
で、上記濃度範囲の化合物(II)を添加する事により
RTD消去効果が顕著に現われ、実用上の目的は充分達
成出来る。However, ordinary TND panels are usually several microns to 20
Since the liquid crystal layer is manufactured to have a thickness on the order of microns, by adding compound (II) in the above concentration range, the RTD erasing effect is remarkable, and the practical purpose can be fully achieved.
以下に実施例により本発明になる化合物の製造法及び本
化合物を含有する液晶組成物の例並びにその効果につい
て更に詳しく説明する。EXAMPLES Below, the method for producing the compound of the present invention, examples of liquid crystal compositions containing the compound, and their effects will be explained in more detail with reference to Examples.
実施例 1 化合物(n)の製造 反応は3段で行なわれるので、3段に分けて説明する。Example 1 Production of compound (n) Since the reaction is carried out in three stages, the explanation will be divided into three stages.
第1段 2−メチル−1−ブロモブタンの製造市販の活
性アミルアルコール((ハ)2−メチル−ブタノール−
1)70gを300Uの三ツロフラスコに入れ一10℃
に冷し、市販の3臭化燐79gを満願ろ斗から1.5時
間かかつて満願した。1st stage Production of 2-methyl-1-bromobutane Commercially available activated amyl alcohol ((iii) 2-methyl-butanol-
1) Put 70g into a 300U Mitsuro flask and heat at -10°C.
I cooled it down to about 100 ml, and poured 79 g of commercially available phosphorus tribromide into a funnel for 1.5 hours.
満願終了5分後に室温に戻し、更に40℃30分加熱し
てから減圧黒部し、140 mmHgで55〜68℃の
部分を採った。Five minutes after the completion of application, the temperature was returned to room temperature, and after further heating at 40°C for 30 minutes, the black part was vacuumed, and the part at 55 to 68°C was taken at 140 mmHg.
この部分を塩化カルシウム、次いで無水炭酸カリ粉末で
処理してのち再び減圧黒部し140mmHgで67〜7
0℃の部分を採った。This part was treated with calcium chloride and then with anhydrous potassium carbonate powder, and then vacuumed again to 67 to 7
The part at 0°C was taken.
収量は60gであり理論値に対する収率は50%であっ
た。The yield was 60 g, which was 50% of the theoretical value.
第2段 P−(,2−メチル−ブトキシ)安息香酸の製
造
11の三ツロフラスコに、か性カリ37g、水52m1
エタノール364m1を入れ、市販のp−ヒドロキシ安
息香酸45gを加えて撹拌溶解させた。2nd stage: Production of P-(,2-methyl-butoxy)benzoic acid In the 11 three-turn flask, 37 g of caustic potassium and 52 ml of water were added.
364 ml of ethanol was added, and 45 g of commercially available p-hydroxybenzoic acid was added and dissolved with stirring.
これに第1段の反応で得られ2−メチル−1−ブロモブ
タン60gを加えて10時間還流加熱後、湯浴上で溶媒
を常圧で溜去し、更に副生するエステルを加水分解する
ため10%のか性カリ水溶液100m1を加え還流加熱
した。To this was added 60 g of 2-methyl-1-bromobutane obtained in the first stage reaction, and after heating under reflux for 10 hours, the solvent was distilled off at normal pressure on a hot water bath, and the by-produced ester was further hydrolyzed. 100 ml of a 10% caustic potassium aqueous solution was added and heated under reflux.
次いで塩酸で酸性にして析出して来る酸を濾過して集め
、これをベンゼン11に加熱溶解してのち室温に戻し、
析出するp−ヒドロキシ安息香酸を除去した。Next, acidify with hydrochloric acid, collect the precipitated acid by filtration, dissolve it in benzene 11 by heating, and then return to room temperature.
The precipitated p-hydroxybenzoic acid was removed.
ベンゼン溶液を約200m1になる寸で濃縮して、析出
するp−(2−メチル−ブトキシ)安息香酸を必要最小
量(約100rrLl)のベンゼンに再溶解後再結晶さ
せて融点110〜112.5℃の無色の結晶15gを得
た。Concentrate the benzene solution to about 200ml, redissolve the precipitated p-(2-methyl-butoxy)benzoic acid in the minimum necessary amount (about 100rrLl) of benzene, and recrystallize it to obtain a solution with a melting point of 110 to 112.5. 15 g of colorless crystals were obtained.
元素分析値
酬算値(C12H16O3として)実験値C69,2%
69.3%
H7,7% 7.7%
0 23.1%
第3段 化合物(II)の製造
第2段で得たp−(2−メチルブトキシ)安息香酸9.
1gに塩化チオニル16gを加え1時間還流加熱した後
、過剰の塩化チオニルを減圧溜去した。Elemental analysis value compensation value (as C12H16O3) Experimental value C69.2%
69.3% H7.7% 7.7% 0 23.1% Third stage Production of compound (II) p-(2-methylbutoxy)benzoic acid obtained in the second stage9.
After adding 16 g of thionyl chloride to 1 g and heating under reflux for 1 hour, excess thionyl chloride was distilled off under reduced pressure.
これにベンゼン16gを加え、更に市販のp−シアノフ
ェノール6gをピリジン15rlニ溶解した溶液を加え
1時間還流加熱後、氷を加え冷却し、ベンゼン100r
Iljと水10゛0rrLlを加えて分液F斗に移して
稀塩酸、稀か性ソーダ水溶液、飽和食塩水で洗滌した後
、ベンゼンを溜去して残る固体をエタノールから再結晶
して8gの化合物(II)即ち(d)−p−(2−メチ
ル−ブトキシ)安息香酸p′−シアノフェニルエステル
の無色の結晶を得た。16 g of benzene was added to this, and a solution of 6 g of commercially available p-cyanophenol dissolved in 15 rl of pyridine was added, and after heating under reflux for 1 hour, ice was added and cooled.
Add Ilj and 10゛0rrLl of water, transfer to a separating funnel, wash with dilute hydrochloric acid, dilute aqueous soda solution, and saturated saline, distill off the benzene, and recrystallize the remaining solid from ethanol to give 8 g. Colorless crystals of compound (II), ie (d)-p-(2-methyl-butoxy)benzoic acid p'-cyanophenyl ester, were obtained.
このものは融点88.2〜89℃で、又クロロホルム溶
液中での施光度〔α〕20=6.2°であった。This product had a melting point of 88.2 to 89°C and a light intensity [α]20=6.2° in a chloroform solution.
又元素分析値は次の通りであった。The elemental analysis values were as follows.
計算値(C19H19N103として) 実験値C7
3,8% 73.6%
H6,2% 6.2%
N 4.5% 4.6%0
15.5%
又、その紫外線吸収スペクトル及び、赤外線吸収スペク
トルを第1図及び第2図に示す。Calculated value (as C19H19N103) Experimental value C7
3.8% 73.6% H6.2% 6.2% N 4.5% 4.6%0
15.5% Further, its ultraviolet absorption spectrum and infrared absorption spectrum are shown in FIGS. 1 and 2.
実施例 2
化合物(II)の液晶組成物としての効果実験(その1
)
4−ジアノ−4′−n−ペン 39%(重量・・・以
チルビフェニル 下回様)4−シ
アノ−4’−n−ヘプ 23%
チルヒ゛フェニル
4−シアノ−4′−n−ペン 9%
チルオキシビフェニル
4−シアノ−4’−n−ヘプ 85%
チルオキシビフェニル
4−シアノ−4’−オクチル 12.5%オキシビフェ
ニル
4−シアノ−4′−n−ペン 8%
チルターフェニル
以上の組成よりなる液晶混合物を調製し、これを液晶組
成物A、とする。Example 2 Effect experiment of compound (II) as a liquid crystal composition (Part 1)
) 4-diano-4'-n-pene 39% (weight... below tylbiphenyl) 4-cyano-4'-n-hep 23% tylphenyl 4-cyano-4'-n-pene 9 % Tyloxybiphenyl 4-cyano-4'-n-hep 85% Tyloxybiphenyl 4-cyano-4'-octyl 12.5% Oxybiphenyl 4-cyano-4'-n-pene 8% Tilterphenyl or higher A liquid crystal mixture having the following composition is prepared and is referred to as liquid crystal composition A.
液晶組成物A、に実施例1で得られた化合物(■)を1
重量係加えたものを液晶組成物Bとする。1 of the compound (■) obtained in Example 1 was added to liquid crystal composition A.
The product with the weight factor added is called liquid crystal composition B.
12±2μmの空隙を有する空の液晶セルを16ケ用意
した。Sixteen empty liquid crystal cells having a gap of 12±2 μm were prepared.
電極は■酸化インジウムを綿布で一定方向に摩擦したも
の■酸化錫を綿布で一定方向に摩擦したもの■酸化イン
ジウムの上に酸化硅素を蒸着し綿布で一定方向に摩擦し
たもの及び■酸化インジウムの上に酸化硅素を傾斜蒸着
したものの4種類各4ヶづつである。The electrodes are: - indium oxide rubbed in a certain direction with a cotton cloth - tin oxide rubbed in a certain direction with a cotton cloth - silicon oxide deposited on indium oxide and rubbed in a certain direction with a cotton cloth, and - indium oxide. There are 4 of each type with silicon oxide deposited on top.
4種類の液晶セル各2ヶづつ計8ヶに液晶組成物Bを注
入する。Liquid crystal composition B was injected into 8 cells, 2 of each of 4 types of liquid crystal cells.
いずれも注入当初はRTDが生成するが、間もなくこれ
が自然に解消し、均一配向が得られた。In both cases, RTD was generated at the beginning of implantation, but this soon resolved itself and uniform orientation was obtained.
外部より力を加えて液晶層を乱して生ずるRTDも自然
に解消した。RTD, which occurs when the liquid crystal layer is disturbed by applying external force, was also naturally resolved.
当初の配向の不均一が極めて著るしい場合でも、多くて
も1時間、通常は数分以内で完全に解消する。Even if the original orientation non-uniformity is very severe, it will completely resolve within an hour at most, and usually within a few minutes.
加熱により、この解消は促進されるが、通常のTNDパ
ネル製造工程の所要時間内に、自らの傾向によって、均
一配向を取るので一般には特別な加熱操作は必要としな
い。Heating accelerates this resolution, but in general, no special heating operation is required since the uniform orientation is achieved by its own tendency within the time required for the normal TND panel manufacturing process.
以上に反し化合物(II)を添加しない液晶組成物Aを
4種類の液晶セル各2ヶに注入したもの8ケはすべてR
TDを生じた。Contrary to the above, all 8 liquid crystal cells in which liquid crystal composition A without compound (II) was injected into two each of four types of liquid crystal cells were R.
TD occurred.
比較的均一な配向をしたもの(RTDの小さいもの)も
外部より力を加えて液晶層を乱すとRTDが拡大し、一
且このようになると均一配向になることは不可能であっ
た。Even if the liquid crystal layer is relatively uniformly aligned (low RTD), if an external force is applied to disturb the liquid crystal layer, the RTD will expand, and once this happens, it is impossible to achieve uniform alignment.
実施例 3
化合物(II)の効果実験(その2)
p−メトキシベンジリデン−p’−n −31%ブチル
アニリン
、−エトキシベンジリデン−p’−n−21%ブチルア
ニリン
p−メトキシベンジリデン−p’ −n −36%へブ
チルアニリン
p−ブトキシベンジリデン−p′−シア 12係ノア
ニリン
以上の組成よりなる液晶混合物を調製し、これを液晶組
成物Cとする。Example 3 Effect experiment of compound (II) (part 2) p-methoxybenzylidene-p'-n -31% butylaniline, -ethoxybenzylidene-p'-n-21% butylaniline p-methoxybenzylidene-p' - A liquid crystal mixture having a composition of n -36% hebutylaniline p-butoxybenzylidene-p'-sia 12-chain noaniline or higher is prepared, and this is designated as liquid crystal composition C.
又、これに実施例1で得られた化合物(■)を0.5%
加えたものを液晶組成物りとする。In addition, 0.5% of the compound (■) obtained in Example 1 was added to this.
The added material is called a liquid crystal composition.
実施例2で使用したと全く同様の液晶セル4種類16ケ
を用いて、実施例2に於ける液晶組成物Bを液晶組成物
りに置き換え、液晶組成物Aを液晶組成物Cに置き換え
た以外は全く同様の実験を打なった結果、組成物りでは
組成物Bと、組成物Cでは組成物A、と全く同様な結果
が得られた。Using 16 liquid crystal cells of four types completely similar to those used in Example 2, liquid crystal composition B in Example 2 was replaced with liquid crystal composition R, and liquid crystal composition A was replaced with liquid crystal composition C. As a result of carrying out the same experiment except for the above, the composition B gave the same results as the composition C, and the composition C gave the same results as the composition A.
尚以上の実施例ではすべて右旋回の化合物(II)につ
いてのみ記したが、(+)活性アミルアルコールを出発
原料とすれば左施性の化合物(■)が得られ、左施主の
化合物(II)は飾光性が逆である以外のすべて性質が
右旋回の化合物(■)と同一であること、及びRT、D
を消去する効果もある事は当業者の容易に類推出来ると
ころである。In the above examples, only the right-handed compound (II) was described, but if (+) activated amyl alcohol is used as a starting material, a left-handed compound (■) can be obtained, and a left-handed compound (■) can be obtained. II) has the same properties as the right-handed compound (■) except that the decorative properties are reversed, and RT, D
Those skilled in the art can easily infer that it also has the effect of erasing .
勿論左施性の化合物(■)では右旋回の化合物(II)
とは逆方向に均一に捩り方向をそろえる。Of course, in the left-handed compound (■), the right-handed compound (II)
Align the twist direction uniformly in the opposite direction.
以上の様に本発明の光学活性なp−(2−メチル−ブト
キシ)安息香酸p′−シアノフェニルエステルを使用す
れば極めて経済的に従来知られているT N D用液晶
の欠点を改良出来る。As described above, by using the optically active p-(2-methyl-butoxy)benzoic acid p'-cyanophenyl ester of the present invention, it is possible to improve the disadvantages of conventionally known TND liquid crystals in an extremely economical manner. .
第1図は化合物(■)の紫外線吸収スペクトル、第2図
は化合物(II)の赤外線吸収スペクトルである。Figure 1 shows the ultraviolet absorption spectrum of compound (■), and Figure 2 shows the infrared absorption spectrum of compound (II).
Claims (1)
ノフェニルエステルの光学活性体。1 Optically active form of p-(2-methyl-butoxy)benzoic acid p'-cyanophenyl ester.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP228776A JPS5811431B2 (en) | 1976-01-10 | 1976-01-10 | optically active ester |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP228776A JPS5811431B2 (en) | 1976-01-10 | 1976-01-10 | optically active ester |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5287138A JPS5287138A (en) | 1977-07-20 |
JPS5811431B2 true JPS5811431B2 (en) | 1983-03-02 |
Family
ID=11525148
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP228776A Expired JPS5811431B2 (en) | 1976-01-10 | 1976-01-10 | optically active ester |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5811431B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH022251Y2 (en) * | 1984-12-27 | 1990-01-19 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0610170B2 (en) * | 1984-12-26 | 1994-02-09 | チッソ株式会社 | Novel optically active compound and liquid crystal composition |
-
1976
- 1976-01-10 JP JP228776A patent/JPS5811431B2/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH022251Y2 (en) * | 1984-12-27 | 1990-01-19 |
Also Published As
Publication number | Publication date |
---|---|
JPS5287138A (en) | 1977-07-20 |
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