JP2980962B2 - Ester compound and liquid crystal composition containing the same - Google Patents
Ester compound and liquid crystal composition containing the sameInfo
- Publication number
- JP2980962B2 JP2980962B2 JP2251803A JP25180390A JP2980962B2 JP 2980962 B2 JP2980962 B2 JP 2980962B2 JP 2251803 A JP2251803 A JP 2251803A JP 25180390 A JP25180390 A JP 25180390A JP 2980962 B2 JP2980962 B2 JP 2980962B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- phase
- crystal composition
- ester compound
- 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.)
- Expired - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 29
- 239000000203 mixture Substances 0.000 title claims description 18
- -1 Ester compound Chemical class 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 28
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 12
- 230000010287 polarization Effects 0.000 description 9
- 230000002269 spontaneous effect Effects 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 230000005621 ferroelectricity Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CMIJBPSBQPUGPK-UHFFFAOYSA-N 2-fluoro-2-methylheptanoic acid Chemical compound CCCCCC(C)(F)C(O)=O CMIJBPSBQPUGPK-UHFFFAOYSA-N 0.000 description 1
- SEGJDCGIQJESDC-UHFFFAOYSA-N 2-methylbutyl 3-phenylprop-2-enoate Chemical compound CCC(C)COC(=O)C=CC1=CC=CC=C1 SEGJDCGIQJESDC-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、安定なサーモトロピックな液晶状態をとり
得、例えば、液晶テレビ等のディスプレイ用、光プリン
ターヘッド、光フーリエ変換素子、ライトバルブ等、液
晶やエレクトロケミクロミズムを利用するオプトエレク
トロニクス関連素子の素材として有用な液晶材料として
利用できる新規なエステル化合物及びこの化合物を含む
液晶組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial application field) The present invention can take a stable thermotropic liquid crystal state, for example, for a display such as a liquid crystal television, an optical printer head, an optical Fourier transform element, a light valve, etc. The present invention relates to a novel ester compound which can be used as a liquid crystal material useful as a material for an optoelectronics device utilizing liquid crystal or electrochemiomics, and a liquid crystal composition containing this compound.
（従来の技術） 現在、液晶化合物が表示材料として種々の機器で応用
され、時計、電卓、小型テレビ等に実用化されている。
これらは、ネマチック液晶材料を主成分としたセルを用
い、TN型あるいはSTN型と呼ばれる表示方式のものが採
用されている。この場合のセルは、液晶化合物の誘電異
方性Δεと電場Ｅとの弱い相互作用（ΔεE2/2）に基づ
く作動であり、電場に対する応答速度が数十msecと遅い
ことが欠点としてあげられている。そのため、テレビに
用いた場合、駆動方式として画素ごとにスイッチング素
子を配置、付加したアクティブマトリクス方式が主とし
て用いられ、大画面化を図る上での障害の一つになって
いる。しかし、1975年R.B.Meyerらによって合成された
４−（４−ｎデシルオキシベンジリデンアミノ）ケイ皮
酸−２−メチルブチルエステル（DOBAMBC）を代表例と
する強誘電性液晶の出現と、それを用いたN.A.Clarkら
の提案した新しい表示方式（Applied Phys.Lett.1980,3
6,899）により、μsecオーダーの高速応答性及び電場を
切っても液晶分子の配向が変わらない特性（メモリー
性）を有する液晶セルが可能となった。これらの材料を
用いた表示素子を使えば、スイッチング素子などを用い
ないマルチプレックス駆動による単純マトリクス方式に
よる液晶ディスプレイが可能となり、アクティブマトリ
クスのものに比べ、生産性やコスト、信頼性さらに大画
面化などの面ではるかに有利なものとなる。(Prior Art) At present, liquid crystal compounds are applied to various devices as display materials, and have been put to practical use in watches, calculators, small televisions, and the like.
These use cells having a nematic liquid crystal material as a main component, and adopt a display type called a TN type or STN type. Cell in this case is actuated based on a weak interaction between the dielectric anisotropy Δε and the electric field E of the liquid crystal compound (ΔεE 2/2), the response speed to the electric field of several tens of msec and slow cited as disadvantages ing. Therefore, when used in a television, an active matrix system in which switching elements are arranged and added for each pixel is mainly used as a driving system, which is one of the obstacles in achieving a large screen. However, a ferroelectric liquid crystal represented by 4- (4-n-decyloxybenzylideneamino) cinnamic acid-2-methylbutyl ester (DOBAMBC) synthesized by RBMeyer et al. In 1975 was used and used. New display method proposed by NAClark et al. (Applied Phys. Lett. 1980, 3
6,899) has made possible a liquid crystal cell having a high-speed response on the order of μsec and a characteristic (memory property) in which the orientation of liquid crystal molecules does not change even when the electric field is cut off. Using display elements made of these materials enables a simple matrix type liquid crystal display to be driven by multiplexing without using switching elements. It will be much more advantageous in such aspects.
このため、現在まで多くの強誘電性液晶材料が合成さ
れ、提案されてきた。これらの強誘電性液晶材料が表示
材料として用いられるためには、いくつかの物性が要求
されるが、その中でも基本的なものとしては、室温近傍
の広い温度範囲でキラルスメクチックＣ相を示し、大き
な自発分極を有し、化学的に安定しているという点であ
る。しかしながら、初期の強誘電性液晶は、自発分極が
10nC/cm2以下と小さく、また分子内にシッフ塩基をもつ
ものが多かったため、化学的に不安定であった。For this reason, many ferroelectric liquid crystal materials have been synthesized and proposed to date. In order for these ferroelectric liquid crystal materials to be used as display materials, several physical properties are required. Among them, the basic ones show a chiral smectic C phase in a wide temperature range near room temperature, It has a large spontaneous polarization and is chemically stable. However, the initial ferroelectric liquid crystal has a spontaneous polarization.
Since it was as small as 10 nC / cm 2 or less and had many Schiff bases in the molecule, it was chemically unstable.
ところが、最近、化学的に安定なエステル化合物によ
る大きな自発分極の発現が報告されている。例えば、次
式、 の化合物は、78.7〜103.3℃の温度領域でキラルスメク
チックＣ相の、また103.3〜120.8℃の温度領域でコレス
テリック相の液晶となるが、この液晶の83℃における自
発分極は89nC/cm2である（特開昭61−43号公報）。However, recently, the occurrence of large spontaneous polarization by a chemically stable ester compound has been reported. For example, Is a liquid crystal of a chiral smectic C phase in a temperature range of 78.7 to 103.3 ° C. and a cholesteric phase in a temperature range of 103.3 to 120.8 ° C., and the spontaneous polarization of this liquid crystal at 83 ° C. is 89 nC / cm 2 . (JP-A-61-43).
一方、キラルスメクチックＣ相を示す温度を低くする
ために、２環の化合物が合成されている。例えば、次
式、 のビフェニル化合物は、降温時44℃からキラルスメクチ
ックＣ相を示す（特開昭59−118744号公報）。On the other hand, bicyclic compounds have been synthesized to lower the temperature at which the chiral smectic C phase is exhibited. For example, The biphenyl compound exhibits a chiral smectic C phase from 44 ° C. when the temperature is lowered (JP-A-59-118744).
さらに、室温近傍で安定にキラルスメクチックＣ相を
示すフェニルピリミジン系化合物が報告されている。例
えば、次式、 の化合物は、40.7〜82.8℃の温度領域でキラルスメクチ
ックＣ相の、82.8〜89.1℃でスメクチックＡ相の液晶と
なる（特開昭61−200973号公報）。In addition, a phenylpyrimidine-based compound stably showing a chiral smectic C phase at around room temperature has been reported. For example, Is a liquid crystal having a chiral smectic C phase in a temperature range of 40.7 to 82.8 ° C. and a smectic A phase at 82.8 to 89.1 ° C. (JP-A-61-200973).
（発明が解決しようとする課題） しかしながら上記エステル化合物は、キラルスメクチ
ックＣ相の温度範囲が高いという欠点を有している。ま
た、上記ビフェニル化合物はキラルスメクチックＣ相が
モノトロピックであり、不安定である。更に、上記ピリ
ミジン系化合物は応答時間が43℃で1500μsecと遅く、
自発分極がかなり小さいと推定される。(Problems to be Solved by the Invention) However, the above ester compound has a drawback that the temperature range of the chiral smectic C phase is high. The biphenyl compound is unstable because the chiral smectic C phase is monotropic. Furthermore, the pyrimidine-based compound has a slow response time of 1500 μsec at 43 ° C.,
It is estimated that the spontaneous polarization is quite small.
尚、近年、不斉炭素上にフッ素やトリフルオロメチル
基を導入した化合物が数多く報告されている。例えば、
Heppkeらは、不斉炭素上にフッ素を導入した次式、 の化合物がキラルスメクチックＣ相で自発分極が400nC/
cm2以上を示すことを報告している（第12回国際液晶会
議予稿集）。In recent years, many compounds having a fluorine or trifluoromethyl group introduced on an asymmetric carbon have been reported. For example,
Heppke et al. Introduced the following formula in which fluorine was introduced on an asymmetric carbon, Is a chiral smectic C phase with a spontaneous polarization of 400 nC /
cm 2 or more (Report of the 12th International Liquid Crystal Conference).
また、不斉炭素上にトリフルオロメチル基を導入した
次式の化合物、 の化合物は、115.5℃〜93.1℃でキラルスメクチックＣ
相を示し、自発分極も166nC/cm2を示すことを報告され
ている（特開昭64−3154号公報）。Further, a compound of the following formula in which a trifluoromethyl group is introduced on an asymmetric carbon, Is a chiral smectic C at 115.5-93.1 ° C.
Phase and spontaneous polarization are also reported to be 166 nC / cm 2 (JP-A-64-3154).
すなわち、高速応答性を要求される表示装置などの液
晶材料には、大きな自発分極を有すること、低粘性を有
すること、或は室温近傍を含む広い温度範囲でキラルス
メクチックＣ相を示すことなどの物性が要求されるが、
現在までのところこれらの物性を充分に満足する材料は
未だ無いのが実状である。That is, a liquid crystal material such as a display device that requires a high-speed response has a large spontaneous polarization, a low viscosity, or a chiral smectic C phase in a wide temperature range including near room temperature. Physical properties are required,
To date, there is no material that sufficiently satisfies these properties.
本発明は、かかる実状に基づいてなされたものであ
り、本発明の目的は液晶化合物として有用なトリフルオ
ロメチル基を含むエステル化合物及びこれを含む液晶組
成物を提供することにある。The present invention has been made based on such a situation, and an object of the present invention is to provide an ester compound containing a trifluoromethyl group useful as a liquid crystal compound and a liquid crystal composition containing the same.
（課題を解決するための手段） 本発明は、下記の一般式（Ｉ）、 （式中、R1およびR2はアルキル基で、同じものでも異な
っているものでも良い）で表される新規なエステル化合
物及びこれを含む液晶組成物からなるものである。(Means for Solving the Problems) The present invention provides the following general formula (I): Wherein R 1 and R 2 are alkyl groups, which may be the same or different, and a liquid crystal composition containing the same.
上記式（Ｉ）中のR1,R2で示されるアルキル基は実用
的な製造上の見地から、各々炭素数１〜18のものが好ま
しい。The alkyl groups represented by R 1 and R 2 in the above formula (I) each preferably have 1 to 18 carbon atoms from the viewpoint of practical production.
尚、特には、上記式中、R2が結合している炭素が不斉
炭素で、この炭素を中心に光学活性が付与されると、単
独あるいは他の化合物との混合により強誘電性液晶とな
り、好ましいものとなる。In particular, in the above formula, the carbon to which R 2 is bonded is an asymmetric carbon, and when optical activity is imparted around this carbon, it becomes a ferroelectric liquid crystal alone or by mixing with another compound. This is preferable.
上記式（Ｉ）の代表的化合物の例とその理化学的性質
を示すと次の通りである。Examples of typical compounds of the above formula (I) and their physicochemical properties are as follows.
５−（２−フルオロ−２−メチルヘプタノイルオキシ）
−２−（４−ヘキシルオキシビフェニル）ピリミジン IR（KBr,cm-1）： 2920,2850,1770,1600,1420,1220,11201 H−NMR（δ値ppm,CDCl3中,TMS基準）： 8.60〜8.80（d,2H）、8.38〜8.60（d,2H）、 7.70〜7.83（d,2H）、7.53〜7.70（d,2H）、 6.93〜7.10（d,2H）、4.06（t,2H） 0.73〜2.43（m,22H） 尚、一般式（Ｉ）で示す化合物中のR1およびR2のアル
キル基の炭素鎖の長さは、その化合物が液晶状態を取り
得る温度域、あるいはその化合物の自発分極などの物性
に影響を持つものであり、目的によって適宜選定され得
るものである。この化合物は単独で用いることは勿論、
他の液晶材料と混合して用いることができることは言う
までもない。5- (2-fluoro-2-methylheptanoyloxy)
-2- (4-hexyloxybiphenyl) pyrimidine IR (KBr, cm -1 ): 2920,2850,1770,1600,1420,1220,1120 1 H-NMR (δ value ppm, in CDCl 3 , based on TMS): 8.60 to 8.80 (d, 2H), 8.38 to 8.60 (d, 2H), 7.70 to 7.83 (d, 2H), 7.53 to 7.70 (d, 2H), 6.93 to 7.10 (d, 2H), 4.06 (t, 2H 0.73 to 2.43 (m, 22H) The length of the carbon chain of the alkyl group of R 1 and R 2 in the compound represented by the general formula (I) is determined in a temperature range where the compound can take a liquid crystal state, It affects physical properties such as spontaneous polarization of the compound, and can be appropriately selected depending on the purpose. This compound can be used alone, of course.
It goes without saying that it can be used in combination with another liquid crystal material.
上記一般式（Ｉ）の本発明の化合物は一般に次の方法
によって得られる。The compounds of the present invention of the above general formula (I) are generally obtained by the following method.
ここで上記反応式に用いた化合物（Ａ）は、次式に従
って合成することができる。 Here, the compound (A) used in the above reaction formula can be synthesized according to the following formula.
また、上記反応式において用いた（１）式の化合物は
次のようにして（３）式の化合物より誘導することがで
きる。 The compound of the formula (1) used in the above reaction formula can be derived from the compound of the formula (3) as follows.
即ち、光学活性（３）式の２−メチル−1,2−エポキ
シアルカンにアミン−フッ化水素錯体または四フッ化ケ
イ素を作用させ、光学活性な（２）式の２−フルオロ−
２−メチル−１−アルカノールを得る（特開昭64−0560
58号公報）。これに過マンガン酸カリウムなどの酸化剤
を作用させて（１）式の化合物を得ることができる。 That is, an amine-hydrogen fluoride complex or silicon tetrafluoride is allowed to act on 2-methyl-1,2-epoxyalkane of the optically active formula (3), and the optically active 2-fluoro- (2) of the formula (2) is reacted.
2-methyl-1-alkanol is obtained (JP-A-64-0560).
No. 58). An oxidizing agent such as potassium permanganate is allowed to act on this to obtain the compound of the formula (1).
（実施例） 次に本発明を実施例により具体的に説明する。(Examples) Next, the present invention will be specifically described with reference to examples.
実施例１ ５−（２−フルオロ−２−メチルヘプタノイルオキ
シ）−２−（４−ヘキシルオキシビフェニル）ピリミジ
ン ５−（２−フルオロ−２−メチルヘブタノイルオキシ）
−２−（４−ヘキシルオキシビフェニル）ピリミジンの
合成５−ヒドロキシ−２−（４−ヘキシルオキシビフェ
ニル）ピリミジン600mg（1.7mmol）、（−）−２−フル
オロ−２−メチルヘプタン酸280mg（1.7mmol）、N,N−
ジシクロヘキシルカルボジイミド350mg（1.7mmol）およ
び４−ジメチルアミノピリジン20mg（0.17mmol）を乾燥
ジクロロメタン20mlに溶解し、室温で一晩攪拌した。反
応終了後、析出した固体を濾別し、濾液を１規定塩酸水
溶液、水で洗浄後、無水硫酸マグネシウムで乾燥した。Example 1 5- (2-fluoro-2-methylheptanoyloxy) -2- (4-hexyloxybiphenyl) pyrimidine 5- (2-fluoro-2-methylheptanoyloxy)
Synthesis of 2- (4-hexyloxybiphenyl) pyrimidine 600 mg (1.7 mmol) of 5-hydroxy-2- (4-hexyloxybiphenyl) pyrimidine, 280 mg (1.7 mmol) of (−)-2-fluoro-2-methylheptanoic acid ), N, N-
350 mg (1.7 mmol) of dicyclohexylcarbodiimide and 20 mg (0.17 mmol) of 4-dimethylaminopyridine were dissolved in 20 ml of dry dichloromethane and stirred at room temperature overnight. After completion of the reaction, the precipitated solid was separated by filtration, and the filtrate was washed with a 1N aqueous hydrochloric acid solution and water, and dried over anhydrous magnesium sulfate.
硫酸マグネシウムを濾別後濃縮し、残査をトルエンを
展開溶媒に用いたシリカゲルクロマトグラフィーによっ
て精製し、エタノールから再結晶して白色固体180mgを
得た。この化合物は、前述の理化学的性質を有してい
た。The magnesium sulfate was filtered off and concentrated, and the residue was purified by silica gel chromatography using toluene as a developing solvent, and recrystallized from ethanol to obtain 180 mg of a white solid. This compound had the above-mentioned physicochemical properties.
液晶性の評価 上記化合物を、ポリイミドを塗布しラビング処理を施
した透明電極付きガラスからなる厚さ３μのセルに注入
し、ホットステージで温度制御をしながら、偏光顕微鏡
観察を行った。温度変化は、１分間に２℃の割合で行っ
た。Evaluation of Liquid Crystallinity The above compound was injected into a 3 μm thick cell made of glass with a transparent electrode coated with polyimide and subjected to rubbing treatment, and observed with a polarizing microscope while controlling the temperature with a hot stage. The temperature was changed at a rate of 2 ° C. per minute.
降温過程では、126.7℃で等方性液体から同定不能な
高次のスメクチック相になり、83.7℃で結晶になった。
昇温過程では、86.2℃で結晶から同定不能な高次のスメ
クチック相になった。During the cooling process, the liquid became a non-identifiable higher smectic phase from an isotropic liquid at 126.7 ° C, and became a crystal at 83.7 ° C.
During the heating process, a high-order smectic phase that could not be identified from the crystal was formed at 86.2 ° C.
実施例２ 液晶組成物の作成 液晶組成物として、スメクチックＣ相を示すが強誘電
性ではないフェニルピリミジン系液晶組成物を用いた。Example 2 Preparation of a liquid crystal composition As a liquid crystal composition, a phenylpyrimidine-based liquid crystal composition exhibiting a smectic C phase but having no ferroelectricity was used.
この組成物の物性は以下に示す通りである。 The physical properties of this composition are as shown below.
上記組成物に実施例１の次式、 で表される化合物を6wt％添加したところ、以下に示す
相転移挙動を示した。 The following formula of Example 1 is applied to the above composition, When the compound represented by the formula (1) was added at 6 wt%, the following phase transition behavior was exhibited.
また、この組成物の応答速度は、100μsec（10Vpp/μ
ｍ、25℃）であった。 The response speed of this composition was 100 μsec (10 Vpp / μ
m, 25 ° C).
比較例 比較化合物を用いた組成物の作成 液晶組成物として、スメクチックＣ相を示すが強誘電
性ではないフェニルピリミジン系液晶組成物を用いた。Comparative Example Preparation of Composition Using Comparative Compound As a liquid crystal composition, a phenylpyrimidine-based liquid crystal composition exhibiting a smectic C phase but having no ferroelectricity was used.
この組成物の物性は以下に示す通りである。 The physical properties of this composition are as shown below.
上記組成物に比較化合物の次式、 で表せる化合物を6wt％添加したところ、以下に示す相
転移挙動を示した。 In the above composition, the following formula of a comparative compound, When 6 wt% of a compound represented by the following formula was added, the following phase transition behavior was exhibited.
また、この組成物の応答速度は、61μsec（10Vpp/μ
ｍ、25℃）であった。 The response speed of this composition was 61 μsec (10 Vpp / μ
m, 25 ° C).
このように、骨格部をビフェニルに変えた化合物は、
組成物にした場合コレステリック相を示さなくなり配向
などの問題から好ましくないことが分かる。Thus, a compound in which the skeleton is changed to biphenyl,
It can be seen that the composition does not show a cholesteric phase and is not preferable due to problems such as orientation.
（発明の効果） 本発明の化合物は、安定なサーモトロピックの液晶状
態を取り得る等、オプトエレクトロニクス関連素子の素
材として極めて優れた効果を奏するものである。(Effects of the Invention) The compound of the present invention exhibits an extremely excellent effect as a material for optoelectronics-related devices, such as being able to take a stable thermotropic liquid crystal state.
従って本発明は、例えば、液晶テレビなどのディスプ
レイ用、プリンターヘッド、光フーリエ変換素子、ライ
トバルブ等、液晶やエレクトロケミクロミズムを利用す
るオプトエレクトロニクス関連素子の素材として有用な
液晶材料といえる。Therefore, the present invention can be said to be a liquid crystal material useful as a material for an optoelectronics-related element utilizing liquid crystal or electrochemism, such as for a display such as a liquid crystal television, a printer head, an optical Fourier transform element, and a light valve.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 平井 利弘 埼玉県戸田市新曽南３丁目17番35号 日 本鉱業株式会社内 (56)参考文献 特開 昭61−200973（ＪＰ，Ａ) 特開 平３−151368（ＪＰ，Ａ) Ｚ．Ｎａｔｒｕｆｏｒｓｃｈ．，Ｂ： Ｃｈｅｍ．Ｓｃｉ．，44（９）ｐ1127− 1131（1989) (58)調査した分野(Int.Cl.6，ＤＢ名) C07D 239/34 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Toshihiro Hirai 3-17-35 Nishinaminami, Toda City, Saitama Japan Inside Mining Co., Ltd. (56) References JP-A-61-200973 (JP, A) JP-A Hei 3-151368 (JP, A) Natruforsch. , B: Chem. Sci. (58) Fields investigated (Int. Cl. 6 , DB name) C07D 239/34 CA (STN) REGISTRY (STN)
Claims (3)
っているものでも良い）で表される新規なエステル化合
物。1. The following general formula: (Wherein, R 1 and R 2 are alkyl groups, which may be the same or different).
活性を有する請求項１記載の新規なエステル化合物。2. The novel ester compound according to claim 1, wherein the compound represented by the general formula (I) has optical activity.
含有することを特徴とする液晶組成物。3. A liquid crystal composition comprising the ester compound according to claim 1 or 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2251803A JP2980962B2 (en) | 1990-09-25 | 1990-09-25 | Ester compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2251803A JP2980962B2 (en) | 1990-09-25 | 1990-09-25 | Ester compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04134072A JPH04134072A (en) | 1992-05-07 |
| JP2980962B2 true JP2980962B2 (en) | 1999-11-22 |
Family
ID=17228159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2251803A Expired - Lifetime JP2980962B2 (en) | 1990-09-25 | 1990-09-25 | Ester compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2980962B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59209855D1 (en) * | 1991-11-08 | 2000-09-07 | Rolic Ag Zug | Fatty acid esters containing a pyrimidine ring as components of liquid crystalline mixtures |
-
1990
- 1990-09-25 JP JP2251803A patent/JP2980962B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Ｚ．Ｎａｔｒｕｆｏｒｓｃｈ．，Ｂ：Ｃｈｅｍ．Ｓｃｉ．，４４（９）ｐ１１２７−１１３１（１９８９） |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04134072A (en) | 1992-05-07 |
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