JPH02191241A - Chlorine-containing optically active biphenyl compound - Google Patents
Chlorine-containing optically active biphenyl compoundInfo
- Publication number
- JPH02191241A JPH02191241A JP943289A JP943289A JPH02191241A JP H02191241 A JPH02191241 A JP H02191241A JP 943289 A JP943289 A JP 943289A JP 943289 A JP943289 A JP 943289A JP H02191241 A JPH02191241 A JP H02191241A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- chlorine
- liquid crystal
- compound
- formula
- 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
- -1 biphenyl compound Chemical class 0.000 title claims abstract description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 235000010290 biphenyl Nutrition 0.000 title claims abstract description 9
- 239000004305 biphenyl Substances 0.000 title claims abstract description 9
- 239000000460 chlorine Substances 0.000 title claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 title claims abstract description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 15
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 10
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 8
- 230000005684 electric field Effects 0.000 abstract description 8
- 230000004044 response Effects 0.000 abstract description 6
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- CLDPEKVZZMSSGL-VEDVMXKPSA-N (4r)-6-chloro-4-methyloctan-1-ol Chemical compound CCC(Cl)C[C@H](C)CCCO CLDPEKVZZMSSGL-VEDVMXKPSA-N 0.000 abstract 1
- PHBQSOODLMGROT-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1 PHBQSOODLMGROT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- WNAFVJVEADYQAI-UHFFFAOYSA-N methyl 2-phenylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=CC=C1 WNAFVJVEADYQAI-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UTIMESSLYFMSPO-UHFFFAOYSA-N 2-methylbutyl 3-[4-[(4-decoxyphenyl)methylideneamino]phenyl]prop-2-enoate Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C=NC1=CC=C(C=CC(=O)OCC(C)CC)C=C1 UTIMESSLYFMSPO-UHFFFAOYSA-N 0.000 description 1
- YNBBQLUKHHSKPW-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 YNBBQLUKHHSKPW-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- DHKUDXSEVBBTEA-UHFFFAOYSA-N methyl 3-hydroxy-4-phenylbenzoate Chemical compound OC1=CC(C(=O)OC)=CC=C1C1=CC=CC=C1 DHKUDXSEVBBTEA-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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〕
本発明は塩素含有光学活性ビフェニル化合物に関し、詳
しくは、強誘電性スメクチック液晶の電界への応答を利
用した、電気光学素子として有用な液晶化合物である、
塩素含有光学活性ビフェニル化合物に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a chlorine-containing optically active biphenyl compound, and more specifically, to a liquid crystal compound useful as an electro-optical device that utilizes the response of a ferroelectric smectic liquid crystal to an electric field. is,
This invention relates to a chlorine-containing optically active biphenyl compound.
液晶は、種々の電気光学素子として応用され、時計や電
卓等の表示に実用化されてきている。現在量も実用化さ
れている液晶表示素子は、ねじれネマチック液晶やコレ
ステリック液晶の誘電的配列効果を利用したものが大部
分である。しかし、期待されている画素数の多い表示素
子への応用に当たっては応答性の点や、駆動マージンが
取れないことによるコントラスト、視角特性等の点で問
題になっている。そのため、各画素毎にスイッチング素
子を形成するＭＯＳパネルやＴＰＴパネルの研究開発が
盛んに行われている。Liquid crystals have been applied as various electro-optical elements and have been put to practical use in displays such as watches and calculators. Most of the liquid crystal display elements currently in practical use utilize the dielectric alignment effect of twisted nematic liquid crystals and cholesteric liquid crystals. However, when applied to display elements with a large number of pixels, which are expected to have a large number of pixels, there are problems in terms of responsiveness, contrast due to the inability to secure a driving margin, viewing angle characteristics, etc. Therefore, research and development of MOS panels and TPT panels in which a switching element is formed for each pixel is actively being conducted.
米国特許第４３６７９２４号には、かかる液晶素子の欠
点を除去するスメクチック相を用いた新しい表示原理に
よる液晶素子が開示されている。US Pat. No. 4,367,924 discloses a liquid crystal device based on a new display principle using a smectic phase that eliminates the drawbacks of such a liquid crystal device.
又、光学的に活性な分子からなるスメクチックＣ８相あ
るいはＨ相を示す液晶化合物は、一般に電気双極子密度
Ｐを有し、強誘電的であることが知られている。これら
のカイラルスメクチック液晶には電気双極子が存在する
ので誘電異方性によるよりも電場の作用を強く受け、こ
の作用力はＰの極性が電場と平行な方向を向くという性
質があるので、印可した電場の方向を反転させることに
より分子の方向を制御することができる。そしてこの分
子の平均的な長軸方向の変化を２枚の偏光板を用いて検
出することにより、電気光学素子として利用できる。Furthermore, liquid crystal compounds exhibiting a smectic C8 phase or H phase composed of optically active molecules generally have an electric dipole density P and are known to be ferroelectric. Since these chiral smectic liquid crystals have electric dipoles, they are more strongly affected by the electric field than by dielectric anisotropy, and this acting force has the property that the polarity of P is oriented in a direction parallel to the electric field, so it cannot be applied. By reversing the direction of the electric field, the direction of the molecules can be controlled. By detecting the change in the average long axis direction of this molecule using two polarizing plates, it can be used as an electro-optical element.
このスメクチックＣ１相またはＨ相の電界への応答を利
用した電気光学素子は、その自発分極と電界の及ぼす作
用力が、誘電異方性によるものより３〜４桁大きいので
、ＴＮ型液晶素子に比べ優れた高速応答性を有し、かつ
、適当な配向制御を行うことによって記憶機能を持たす
ことが可能であり、高速光学シャッターまたは表示情報
量の多いデイスプレー等への応用が期待されるものであ
る。Electro-optical devices that utilize the response of this smectic C1 phase or H phase to an electric field have a spontaneous polarization and an action force exerted by the electric field that is 3 to 4 orders of magnitude larger than that due to dielectric anisotropy, so they are suitable for TN-type liquid crystal devices. It has superior high-speed response compared to others, and can have a memory function by performing appropriate orientation control, and is expected to be applied to high-speed optical shutters and displays with a large amount of displayed information. It is.
このような強誘電性を有するカイラルスメクチック液晶
材料については、これまでも種々の化合物が合成され、
またその性質についても研究されている。Various compounds have been synthesized for chiral smectic liquid crystal materials having ferroelectric properties.
Its properties are also being studied.
このような考えに基づき、例えば、光学活性な２−メチ
ルブチル−ｐ−（ｐ−ｎ−デシロキシベンジリデンアミ
ノ）シンナメート（ＤＯＢＡＭＢＣ）化合物を強誘電性
液晶組成物の一成分として使用することが提案された。Based on this idea, it has been proposed, for example, to use an optically active 2-methylbutyl-p-(p-n-decyloxybenzylideneamino)cinnamate (DOBAMBC) compound as a component of a ferroelectric liquid crystal composition. Ta.
しかしながら、この化合物は、液晶性を示す温度が６０
°Ｃ以上と高い温度であるため、使用に際して温度的制
限を受けていた。However, this compound exhibits liquid crystallinity at a temperature of 60
Because the temperature is as high as °C or higher, there were temperature restrictions when using it.
室温付近を中心に、広い温度範囲にわたって強誘電性を
示し、しかも応答時間の短い液晶組成物が求められてい
た。There has been a need for a liquid crystal composition that exhibits ferroelectricity over a wide temperature range, centered around room temperature, and has a short response time.
本発明者等は、上記現状に鑑み、該表示素子用液晶組成
物の使用可能な温度範囲が適切な光学活性化合物を見出
すべく鋭意検討を重ねた結果、次の一般式（Ｉ）で表さ
れる新規な塩素含有光学活性ビフェニル化合物が上記の
目的に使用するのに極めて好適な化合物であることを見
出した。In view of the above-mentioned current situation, the present inventors have conducted intensive studies to find an optically active compound that has an appropriate temperature range in which the liquid crystal composition for display devices can be used. It has been found that a novel chlorine-containing optically active biphenyl compound is an extremely suitable compound for use for the above purpose.
（式中、Ｒ＋、Ｒｔはそれぞれ独立して、置換基を有し
てもよい炭素原子数１〜１８のアルキル基ま素原子また
は炭素原子数１〜１０のアルキル基を示し、ｍは２〜５
を示し、ｎは１〜３を示し、＊は不斉炭素原子を示す。(In the formula, R+ and Rt each independently represent an alkyl group having 1 to 18 carbon atoms, which may have a substituent, or an alkyl group having 1 to 10 carbon atoms, and m is 2 to 10 carbon atoms.) 5
, n represents 1 to 3, and * represents an asymmetric carbon atom.
ただし、Ｒ３およびＲ２の少なくとも一方は上記の光学
活性基を示す。）上記−軟式（Ｉ）で表される塩素含有
光学活性ビフェニル化合物についてさらに詳述する。However, at least one of R3 and R2 represents the above optically active group. ) The chlorine-containing optically active biphenyl compound represented by the above soft formula (I) will be described in further detail.
Ｒで示される炭素原子数１〜１８のアルキル基としては
、メチル、エチル、プロピル、ブチル、ペンチル、ヘキ
シル、ヘプチル、オクチル、ノニル、デシル、ラウリル
、ミリスチル、バルミチル、ステアリル等があげられる
。Examples of the alkyl group having 1 to 18 carbon atoms represented by R include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, lauryl, myristyl, valmityl, stearyl, and the like.
本発明の化合物は、光学活性基を有することから、強誘
電性液晶組成物の一成分として使用することができる。Since the compound of the present invention has an optically active group, it can be used as a component of a ferroelectric liquid crystal composition.
以下、本発明を実施例によって説明する。しかしながら
、本発明は以下の実施例によって制限を受けるものでは
ない。Hereinafter, the present invention will be explained by examples. However, the present invention is not limited by the following examples.
実施例 １
−４−ビフェニルカルボン メチルエステルのＡ４′−
ヒドロキシ−４−ビフェニルカルボン酸メチル０．９６
ｇ、 （Ｒ）−６−クロロ−４−メチルオクタツール
０．７０ｇ、 トリフェニルホスフィン１．２１ｇお
よびアゾジカルボン酸エチル０．８０ｇをエチルエチル
１０１ｄに溶解させ、室温で３時間攪拌した。Example 1 A4'- of -4-biphenylcarbon methyl ester
Methyl hydroxy-4-biphenylcarboxylate 0.96
0.70 g of (R)-6-chloro-4-methyloctatool, 1.21 g of triphenylphosphine and 0.80 g of ethyl azodicarboxylate were dissolved in ethyl ethyl 101d and stirred at room temperature for 3 hours.
析出したトリフェニルホスフィンオキシトをろ側稜、ろ
液を脱溶媒した。脱溶媒後残渣をｎ−ヘキサン／酢酸エ
チル（９３／７）を展開溶媒とじてシリカゲルカラムで
精製し、（Ｒ）−４”−（６”−クロロ４”−メチルオ
クチルオキシ）−４−ビフェニルカルボン酸メチルエス
テルの白色固体１．０７ ｇ ヲ得り。The precipitated triphenylphosphine oxyto was removed from the filter side, and the filtrate was desolvated. After removing the solvent, the residue was purified with a silica gel column using n-hexane/ethyl acetate (93/7) as the developing solvent to obtain (R)-4"-(6"-chloro4"-methyloctyloxy)-4-biphenyl. 1.07 g of a white solid of carboxylic acid methyl ester was obtained.
融点１０２．８〜１０３．３°Ｃ
■ Ｒ：
２９２５ｃｍ−’（ｓ）
１５２５ｃｍ−’（ｗ）
１４３０ｃｍ−’（ｗ）
１２００ｃｍ−’（ｍ）
８２５ｃｍ−’（ｍ）
実施例２
１７１５ｃｍ−’（ｓ）
１４９５ｃｍ−’ （ｗ）
１３９５ｃ＋ａ−’（ｗ）
１１１０ｃｍ−’（ｍ）
７７０ｃｍ−’（ｍ）
１６００ｃｍ−’（ｍ）
１４５５ｃｍ−’（ｗ）
１２８５ｃ＋ｎ−’（ｓ）
１０３０ｃｍ−’ （ｗ）
ビフェニルカルボン
一゛シルエステルの入
実施例１で得られたビフェニルカルボン酸メチルエステ
ルを水酸化カリウム／エチルアルコール水溶液でけん化
した後、１０％塩酸を用いて中和して（Ｒ）−４′−（
６”−クロロ−４”−メチルオクチルオキシ）−４−ビ
フェニルカルボン酸を得た。このビフェニルカルボン酸
０．４０ｇ、デシルアルコール０．１９ｇ、アゾジカル
ボン酸ジエチル０．２２ｇおよびトリフェニルホスフィ
ン０．３４ｇをエチルエーテル５ｄに溶解させ、室温で
３時間撹拌した。実施例１と同様の処理を行なった後、
ｎ−ヘキサン／酢酸エチル（９５１５）を展開溶媒とし
てシリカゲルカラムで精製して、（Ｒ）−４’−（６”
−クロロ−４″メチルオクチルオキシ）−４−ビフェニ
ルカルボン酸デシルエステルの無色液体０．３１ｇを得
た。Melting point 102.8-103.3°C ■ R: 2925cm-'(s) 1525cm-'(w) 1430cm-'(w) 1200cm-'(m) 825cm-'(m) Example 2 1715cm-'( s) 1495cm-' (w) 1395c+a-' (w) 1110cm-' (m) 770cm-' (m) 1600cm-' (m) 1455cm-' (w) 1285c+n-' (s) 1030cm-' (w) Addition of biphenylcarboxylic acid methyl ester The biphenylcarboxylic acid methyl ester obtained in Example 1 was saponified with a potassium hydroxide/ethyl alcohol aqueous solution, and then neutralized with 10% hydrochloric acid to (R)-4'- (
6''-chloro-4''-methyloctyloxy)-4-biphenylcarboxylic acid was obtained. 0.40 g of this biphenylcarboxylic acid, 0.19 g of decyl alcohol, 0.22 g of diethyl azodicarboxylate and 0.34 g of triphenylphosphine were dissolved in ethyl ether 5d and stirred at room temperature for 3 hours. After performing the same treatment as in Example 1,
It was purified with a silica gel column using n-hexane/ethyl acetate (9515) as a developing solvent to obtain (R)-4'-(6"
0.31 g of colorless liquid of -chloro-4''methyloctyloxy)-4-biphenylcarboxylic acid decyl ester was obtained.
Ｉ Ｒ：
２９２５ｃｍ−’（ｓ） 、１７１５ｃｍ−’（ｓ）
、１６０５ｃｍ−’（ｍ）、１５２５ｃｍ−’（ｗ）
、１４９５ｃ「’（ｗ） 、１４６０ｃ＋＋＋−’（ｗ
）、１３８０ｃｍ−’（ｗ） 、１２７５ｃｍ−’（ｓ
） 、１２４５ｃｍ−’（ｍ）、１１９０ｃｍ−’（ｍ
） 、１１１０ｃｎ＋−’（ｍ） 、１０３５ｃｍ−’
（ｗ）、８３０ｃｍ−’ （ｍ）、７７５ｃ＋＋＋−’
（ｎ＋）この化合物を二枚のガラス板間にはさみ、偏
光顕微鏡による相形態観察を行なった結果、以下の相転
移を確認した。IR: 2925cm-'(s), 1715cm-'(s)
, 1605cm-'(m), 1525cm-'(w)
, 1495c "'(w) , 1460c+++-'(w
), 1380cm-'(w), 1275cm-'(s
), 1245cm-'(m), 1190cm-'(m
), 1110cn+-' (m), 1035cm-'
(w), 830cm-' (m), 775c+++-'
(n+) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
実施例３
４−ビフェニルカルボン オクチルエスールのＡ戒
Ｉ Ｒ：
２９４０ｃｍ”’（ｓ） 、１７１５ｃ＋ｍ−’（ｓ
） 、１６０５ｃｍ−’（ｍ） 、１５２５ｃｍ−
’（ｗ） 、１５００ｃｍ−’（ｗ） 、１４７０
ｃｍ−’（ｗ） 、１３８５ｃｍ−’（ｗ） 、１
２７５ｃｍ−’（ｓ） 、１２５０ｃｍ−’（ｍ）
、１１９０ｃ＋＋＋−’（ｍ） 、１１１５ｃｍ−
’（ｍ） 、１０３１０３Ｏ’（ｗ） 、８３０ｃ
ｍ−’ （ｍ） 、 ７７５ｃｍ−’ （ｍ）この化
合物を二枚のガラス板間にはさみ、偏光顕微鏡による相
形態観察を行なった結果、以下の相転移を確認した。Example 3 A commandment I of 4-biphenylcarbon octyl esul R: 2940cm''(s), 1715c+m-'(s
), 1605cm-'(m), 1525cm-
'(w), 1500cm-'(w), 1470
cm-'(w), 1385cm-'(w), 1
275cm-'(s), 1250cm-'(m)
, 1190c+++-' (m) , 1115cm-
'(m), 103103O'(w), 830c
m-' (m), 775 cm-' (m) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
（Ｒ）−４’−（６”−クロロ−３″−メチルへキシル
オキシ）ビフェニルカルボン酸０．３０ｇ、オクタツー
ル０．２０ｇ、アブジカルボン酸ジエチル０．２１ｇお
よびトリフェニルホスフィン０．３１ｇをエチルエーテ
ル５−に溶解させ、室温で２時間攪拌した。実施例１と
同様の処理を行なった後、ｎ−ヘキサン／酢酸エチル（
９３／７）を展開溶媒としてシリカゲルカラム精製し、
（Ｒ）−４’−（６”−クロロ−３”−メチルへキシル
オキシ）ビフェニルカルボン酸オクチルエステルの無色
液体０．２７ｇを得た。0.30 g of (R)-4'-(6''-chloro-3''-methylhexyloxy)biphenylcarboxylic acid, 0.20 g of octatool, 0.21 g of diethyl abdicarboxylate and 0.31 g of triphenylphosphine were dissolved in ethyl ether. 5- and stirred at room temperature for 2 hours. After carrying out the same treatment as in Example 1, n-hexane/ethyl acetate (
93/7) was purified using a silica gel column as a developing solvent,
0.27 g of a colorless liquid of (R)-4'-(6''-chloro-3''-methylhexyloxy)biphenylcarboxylic acid octyl ester was obtained.
実施例４
６−クロロ−４−メチルノニルエスールのム４′−オク
チルオキシ−４−ビフェニルカルボン酸０．３３ｇ、（
Ｒ）−６−クロロ−４−メチルノニルアルコ−ル０．１
２ｇ、アゾジカルボン酸ジエチル０．２１ｇおよびトリ
フェニルホスフィン０．３１ｇをエチルエーテル５ａｄ
ｌに溶解させ、室温で３時間攪拌した。実施°例１と同
様の処理を行なった後、ｎ−ヘキサン／エチルエーテル
（９５１５）を展開溶媒としてシリカゲルカラム精製し
、（Ｒ）−４”オクチルオキシ−４−ビフェニルカルボ
ン酸−６−クロロ−４−メチルノニルエステルの白色固
体０．２５ｇを得た。Example 4 0.33 g of 6-chloro-4-methylnonyl esul 4'-octyloxy-4-biphenylcarboxylic acid, (
R)-6-chloro-4-methylnonyl alcohol 0.1
2g, diethyl azodicarboxylate 0.21g and triphenylphosphine 0.31g in ethyl ether 5ad
1 and stirred at room temperature for 3 hours. After carrying out the same treatment as in Example 1, purification was carried out on a silica gel column using n-hexane/ethyl ether (9515) as a developing solvent to obtain (R)-4''octyloxy-4-biphenylcarboxylic acid-6-chloro- 0.25 g of a white solid of 4-methylnonyl ester was obtained.
■ Ｒ：
２９５０ｃａｉ−’（ｓ） 、１７１５ｃａ＋−’（ｓ
） 、１６１０ｃｍ−’（ｍ）、１５３０ｃｍ−’（ｗ
） 、１５００ｃ＋ｗ−’（ｗ） 、１４７０ｃｍ＋−
’（ｗ）、１３８５ｃｍ−’（ｗ） 、 １２７５ｃ
ｍ−’（ｓ） 、 １２５０ｃｍ−’（ｍ） 、１
１９５ｃｍ−’（ｍ） 、 １１１５ｃｍ−’（ｗ＋
） 、 １０４１０４Ｏ’（ｗ） 、８３５ｃｍ−
’ （ｍ）、７８０ｃｍ−’ （ｍ）この化合物を二枚
のガラス板間にはさみ、偏光顕微鏡による相形態観察を
行なった結果、以下の相転移を確認した。■ R: 2950cai-'(s), 1715ca+-'(s
), 1610cm-'(m), 1530cm-'(w
), 1500c+w-'(w), 1470cm+-
'(w), 1385cm-'(w), 1275c
m-'(s), 1250cm-'(m), 1
195cm-'(m), 1115cm-'(w+
), 104104O'(w), 835cm-
' (m), 780 cm-' (m) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
参考例
次の一般式で示される４種の化合物を混合して母液晶組
成物を作成した。Reference Example A mother liquid crystal composition was prepared by mixing four types of compounds represented by the following general formula.
この母液晶組成物は下記の相転移を与える。This mother liquid crystal composition provides the following phase transition.
この母液晶組成物９０部に実施例２および実施例４で合
成された本発明化合物をそれぞれ１０部添加した液晶組
成物は下記の物性を有する。A liquid crystal composition obtained by adding 10 parts each of the compounds of the present invention synthesized in Example 2 and Example 4 to 90 parts of this mother liquid crystal composition has the following physical properties.
ｍＡ
なお、上記の液晶組成物を配向膜としてポリイミドを塗
布し、その表面をラビングすることにより平行配向処理
を施したガラス透明電極を備えた厚さ２μｍのセルに注
入して液晶表示素子とし、±１５Ｖの電界（６０Ｈｚ矩
形波交流）を印加した時の２０°Ｃにおける応答速度（
Ｐｓ）および三角波法を用いて自発分極（τ）を測定し
たところ以下の値が得られた。mA Note that the above liquid crystal composition was applied as an alignment film with polyimide, and the surface was injected into a 2 μm thick cell equipped with a glass transparent electrode subjected to a parallel alignment treatment by rubbing to obtain a liquid crystal display element. Response speed at 20°C when an electric field of ±15V (60Hz square wave AC) is applied (
When the spontaneous polarization (τ) was measured using Ps) and the triangular wave method, the following values were obtained.
以上の結果から明らかなごとく、本発明になる塩素含有
光学活性ビフェニル化合物を少量添加することにより、
Ｓａ＋Ｃ”相を有する母液晶のＳａｃ’″相に自発分極
を付与し、カイラルスメクチックＣ相とすることができ
る。As is clear from the above results, by adding a small amount of the chlorine-containing optically active biphenyl compound of the present invention,
Spontaneous polarization can be imparted to the Sac''' phase of the mother liquid crystal having the Sa+C'' phase to form a chiral smectic C phase.
したがって、本発明になる塩素含有光学活性ビフェニル
化合物は強誘電性液晶組成物の一成分として用いるのに
有用である。Therefore, the chlorine-containing optically active biphenyl compound of the present invention is useful as a component of a ferroelectric liquid crystal composition.
Claims (1)
ニル化合物。 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒ＿１、Ｒ＿２はそれぞれ独立して、置換基を
有してもよい炭素原子数１〜１８のアルキル基または基
▲数式、化学式、表等があります▼を示し、Ｒ＿３は水
素原子または炭素原子数１〜１０のアルキル基を示し、
ｍは２〜５を示し、ｎは１〜３を示し、＊は不斉炭素原
子を示す。ただし、Ｒ＿１およびＲ＿２の少なくとも一
方は上記の光学活性基を示す。）[Claims] A chlorine-containing optically active biphenyl compound represented by the following general formula (I). ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, R_1 and R_2 are each independently an alkyl group or group having 1 to 18 carbon atoms which may have a substituent ▲ Numerical formulas, chemical formulas, There are tables, etc. ▼, R_3 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms,
m represents 2 to 5, n represents 1 to 3, and * represents an asymmetric carbon atom. However, at least one of R_1 and R_2 represents the above optically active group. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP943289A JP2764596B2 (en) | 1989-01-18 | 1989-01-18 | Chlorine-containing optically active biphenyl compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP943289A JP2764596B2 (en) | 1989-01-18 | 1989-01-18 | Chlorine-containing optically active biphenyl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02191241A true JPH02191241A (en) | 1990-07-27 |
| JP2764596B2 JP2764596B2 (en) | 1998-06-11 |
Family
ID=11720168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP943289A Expired - Fee Related JP2764596B2 (en) | 1989-01-18 | 1989-01-18 | Chlorine-containing optically active biphenyl compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2764596B2 (en) |
-
1989
- 1989-01-18 JP JP943289A patent/JP2764596B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2764596B2 (en) | 1998-06-11 |
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