KR800000594B1 - Nematic liquid crystal composition - Google Patents
Nematic liquid crystal composition Download PDFInfo
- Publication number
- KR800000594B1 KR800000594B1 KR7601344A KR760001344A KR800000594B1 KR 800000594 B1 KR800000594 B1 KR 800000594B1 KR 7601344 A KR7601344 A KR 7601344A KR 760001344 A KR760001344 A KR 760001344A KR 800000594 B1 KR800000594 B1 KR 800000594B1
- Authority
- KR
- South Korea
- Prior art keywords
- liquid crystal
- crystal composition
- nematic liquid
- compn
- acid
- Prior art date
Links
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
본 발명은 네마틱 액정조성물, 특히 넓은 온도범위를 갖는 새로운 네마틱 액정조성물에 관한 것이다.The present invention relates to nematic liquid crystal compositions, in particular new nematic liquid crystal compositions having a wide temperature range.
네마틱 액정조성물(차후에는 N-조성물이라 약칭함)은 그것이 가지는 유전이방성에 따라 두 종류로 구분할 수 있다. 그 하나는 음유전성을 갖는 N-액정조성물(차후에는 Nn-액정조성물이라 약칭함)이고 또 다른 하나는 양유전성을 갖는 N-액정조성물(차후에는 Np-액정조성물이라 약칭함)로 되어 있다. N-액정조성물은, 그것에 전계를 걸어 주었을 때 생기는 광학적 변화를 이용해서 광학적 표시 소립자에 응용한다. Nn-액정조성물은, 그것에 전계를 걸어주어서 생기는 이온과 Nn-결정분자집단과의 충돌로 인해서 발생되는 광산란현상 즉 다시 말해서 동적산란현상(DSM)을 이용해서 DSM형 표시소자의 액정재료로서 이동할 수도 있다. 또한 Np-액정조성물은, 그것에 전계를 걸어주어서 생기는 Np-액정분자의 비틀림 또는 기울기의 변화 즉 전계효과현상(mode)(FEM)을 이용해서 FEM형 표시소자의 액정재료로서 사용할 수 있다.Nematic liquid crystal compositions (hereinafter referred to as N-compositions) can be classified into two types according to their dielectric anisotropy. One is an N-liquid crystal composition having a negative dielectric property (hereinafter abbreviated as Nn-liquid crystal composition) and the other is an N-liquid crystal composition having a positive dielectric property (hereinafter abbreviated as Np-liquid crystal composition). The N-liquid crystal composition is applied to an optical display elementary particle by using an optical change generated when an electric field is applied to it. The Nn-liquid crystal composition may move as a liquid crystal material of a DSM type display device by using a light scattering phenomenon, ie, a dynamic scattering phenomenon (DSM), caused by a collision between ions generated by applying an electric field and a group of Nn-crystal molecules. have. In addition, the Np-liquid crystal composition can be used as a liquid crystal material of a FEM type display device by utilizing a change in the torsion or inclination of the Np-liquid crystal molecules caused by applying an electric field thereto, that is, a field effect mode (FEM).
N-액정조성물은 광범위한 온도범위에 있어서, 특히 저온영역에 있어서 광범위한 네마틱 액정상(相)을 가질 수가 있다.The N-liquid crystal composition can have a wide range of nematic liquid crystal phases in a wide temperature range, particularly in a low temperature region.
본 발명의 목적은 네마틱 액정상 온도범위를 갖는 신규의 액정조성물에 관한 것이다.An object of the present invention relates to a novel liquid crystal composition having a nematic liquid crystal phase temperature range.
본 발명의 목적은, 아래와 같은 구조식(Ⅰ)의 p-아미노신나민산-p′-n-알콕시페닐에스테르의 2가지 이상을 혼합시켜서 네마틱 액상조성물을 만드는 것이다.An object of the present invention is to prepare a nematic liquid composition by mixing two or more kinds of p-aminocinnamic acid-p′-n-alkoxyphenyl ester of the following structural formula (I).
윗 구조식에서의In the above structural formula
R은 탄소수 4-8의 직쇄형 알킬기를 나타냄.R represents a straight chain alkyl group having 4-8 carbon atoms.
본 발명의 네마틱 액정조성물은 Np-액정조성물에 있어서 상기와 같은 구조식(Ⅰ)로 표시되는 p-시아노신나민산-p′-n-알콕시페닐에스테르의 2종류 이상을 함유함을 특징으로 한다.The nematic liquid crystal composition of the present invention is characterized by containing two or more kinds of p-cyanocinnamic acid-p'-n-alkoxyphenyl esters represented by the above structural formula (I) in the Np-liquid crystal composition. .
본 발명의 네마틱 액정조성물로 쓰이는 p-시아노신나민산-p′-n-알콕시에스테르의 구체적인 화합물로는 다음과 같은 것들이 있다.Specific compounds of the p-cyanocinnamic acid-p'-n-alkoxy ester used as the nematic liquid crystal composition of the present invention include the following compounds.
위의 구조식(Ⅰ)로 표기한 p-시아노신나민산-p′-n-알콕시페닐에스테르는 그 자체가 새로운 Np-액정화합물이지만 이 화합물은, 일반적으로 상응하는 p-n-알콕시페놀과 p-시아노신나민산 클로라이드를 피리딘, 트리에틸아민등의 탈염화수소제를 사용하여 축합시켜서 쉽게 만들 수 있다. 이 반응은 아래와 같이 나타낼 수 있다.The p-cyanocinnamic acid-p'-n-alkoxyphenyl ester represented by the above structural formula (I) is itself a new Np-liquid crystal compound, but this compound is generally a corresponding pn-alkoxyphenol and p-sia Nosinnamic acid chloride can be easily made by condensation using dehydrochlorination agents such as pyridine and triethylamine. This reaction can be expressed as follows.
윗 식에서의 R은 구조식(Ⅰ)의 R과 같다.R in the above formula is the same as R in Structural Formula (I).
원료인 p-시아노신나민산 클로라이드는, 예를들면 p-사이노벤즈알데히드와 마론산을 피리딘 및 피페리딘등의 존재하에 가열 교반하여 p-시아노신나민산을 합성하고 그것을 염화치오닐을 사용하여 염소화시키므로서 쉽게 만들 수 있다.For example, p-cyanocinnamic acid chloride as a raw material is heated and stirred with p-cyanobenzaldehyde and maronic acid in the presence of pyridine and piperidine to synthesize p-cyanocinnamic acid, which is then used with thionyl chloride. It can be easily made by chlorination.
다음에는 합성예를 들어서 구체적인 제조법을 설명하려 한다.Next, a specific example will be described using a synthesis example.
[합성예]Synthesis Example
p-시아노벤즈알데히드 0.2몰과 마론산 0.3몰을 실온에서 80ml인 피리딘에 용해시키고 그 용액에 피페리딘 30적(滴)을 가하여 약 100℃에서 4시간동안 가열 교반한다. 반응이 끝난 후에 용액을 묽은 염산(250ml 염산/250g 물)에 천천히 넣어서 생성되는 백색 침전을 여과 분별회수하고 묽은 염산과 물로 세척한 후에 빙초산을 사용하여 재결정시키면 p-시아노 신나민산을 얻을 수 있다. 또한 p-시아노 신나민산 0.1몰에 염화치오닐 0.3몰을 넣어서 약 80℃에서 3시간 가열 교반하고 반응 종료후에 잔존하는 염화치오닐을 감압하에 제거하여 p-시아노신나민산 클로라이드를 만들 수 있다.0.2 moles of p-cyanobenzaldehyde and 0.3 moles of maronic acid are dissolved in 80 ml of pyridine at room temperature, and 30 drops of piperidine is added to the solution, followed by heating and stirring at about 100 ° C. for 4 hours. After completion of the reaction, the solution was slowly added to dilute hydrochloric acid (250ml hydrochloric acid / 250g water) to filter out the white precipitate, filtered off, washed with dilute hydrochloric acid and water, and recrystallized with glacial acetic acid to obtain p-cyano cinnamic acid. . In addition, 0.1 mol of p-cyano cinnamic acid is added with 0.3 mol of thionyl chloride, and the mixture is heated and stirred at about 80 ° C. for 3 hours. After the completion of the reaction, the remaining thionyl chloride can be removed under reduced pressure to form p-cyanocinnamic acid chloride. .
이상에 기술한 바와같이 해서 만든 p-시아노신나민산 클로라이드 0.02몰과 p-n-부틸옥시페놀 0.02몰을 50ml의 벤젠에 넣고 여기에 50ml의 피리딘을 서서히 적가하고, 적가완료후 약 60℃에서 3시간동안 교반 가열한다. 반응종료후 반응혼합물에 100ml의 벤젠을 가하고 그후에 묽은염산, 수산화나트륨 수용액 및 물로서 세척하여 유기층을 무수황산나트륨에서 건조시킨다. 황산나트륨을 걸러낸 다음 벤젠을 감압하에 제거시키고 잔류물을 에타놀로 재결정시켜서 p-시아노신나민산-p′-n-부틸옥시페닐에스테르(화합물 Ⅰ)을 만든다.0.02 mole of p-cyanosuccinic acid chloride and 0.02 mole of pn-butyloxyphenol prepared as described above are added to 50 ml of benzene, and 50 ml of pyridine is slowly added dropwise thereto, followed by 3 hours at about 60 ° C. While stirring is heated. After completion of the reaction, 100 ml of benzene was added to the reaction mixture, which was then washed with dilute hydrochloric acid, aqueous sodium hydroxide solution and water, and the organic layer was dried over anhydrous sodium sulfate. Sodium sulfate was filtered off, benzene was removed under reduced pressure and the residue was recrystallized from ethanol to give p-cyanosuccinamic acid-p'-n-butyloxyphenylester (Compound I).
상술한 제조방법에 있어서의 p-n-부틸옥시페놀 대신에 p-n-펜틸옥시페놀이나 p-n-헥실옥시페놀이나 p-n-헵틸옥시페놀 또는 p-n-옥틸옥시페놀을 사용하고, 그밖의 방법은 상술한 바와같이 하여 상응하는 p-시아노신나민산-p′-n-알콕시페놀에스테르를 만들 수도 있다.Pn-pentyloxyphenol, pn-hexyloxyphenol, pn-heptyloxyphenol, or pn-octyloxyphenol is used in place of pn-butyloxyphenol in the above-mentioned production method, and other methods are as described above. The corresponding p-cyanocinnamic acid-p'-n-alkoxyphenol ester can also be made.
이와같이 해서 합성한 p-시아노신나민산-p′-n-알콕시페닐에스테르는 적외선 스펙트럼, 개스크로마토그람 및 질량스펙트럼에 의해 목적의 화합물인가를 확인할 수 있다.The p-cyanocinnamic acid-p'-n-alkoxyphenyl ester thus synthesized can be confirmed to be the target compound by infrared spectrum, gas chromatogram and mass spectrum.
전술한 화합물(1)-(5)는 Np-액정화합물이지만 각 화합물의 고체-네마틱 액정상 전이점(KN점) 및 네마틱 액정-등방성 액체상 전이점(NI점)을 제1표에 기록한다.Compounds (1)-(5) described above are Np-liquid crystal compounds, but the solid-nematic liquid crystal phase transition point (KN point) and the nematic liquid crystal-isotropic liquid phase transition point (NI point) of each compound are recorded in the first table. do.
[제1표][Table 1]
본 발명의 네마틱 액정조성물로는 구조식(Ⅰ)로 표시되는 화합물을 2종류 또는 3종류 또는 그 이상을 혼합시켜 사용할 수 있다. 이때의 각 성분의 혼합비는 제한은 없고 어떤 범위의 혼합비도 좋음을 알아 냈다.As the nematic liquid crystal composition of the present invention, the compound represented by Structural Formula (I) may be used by mixing two or three or more kinds thereof. There was no restriction in the mixing ratio of each component at this time, and it was found that the mixing ratio of any range was good.
본 발명의 네마틱 액정조성물을 만드는데는, 각 성분을 평량하여 질소가스하에서 180℃정도로 가열하여 등방성 액체로 하여 10분간 교반 혼합하는 것이 좋다. 또는 각 성분을 혼합시킨 뒤에 가열 교반해서 등방성 액체로 만들어도 좋다.In order to make the nematic liquid crystal composition of the present invention, it is preferable that each component is weighed and heated to about 180 ° C. under nitrogen gas, and stirred and mixed for 10 minutes as an isotropic liquid. Alternatively, the components may be mixed with heat and stirred to form an isotropic liquid.
본 발명의 Np-액정조성물의 네마틱 액정상 온도는 약 60°-140℃와 같이 광범위하게 변할 수 있고 특히 저온에서 광범위함을 특징으로 한다. 이렇게 해서 구조식(Ⅰ)화합물을 혼합해서 만든 Np-액정조성물의 네마틱 액정상 온도범위는 그 액정조성물을 구성하는 각 성분 자체의 네마틱 액정상 온도범위 보다도 넓고 또한 저온에서 더욱 넓다는 특징이 있다. 본 발명의 Np-액정조성물은 FEM형 표시소자의 액정재료소서 유용함을 알아냈다.The nematic liquid crystal phase temperature of the Np-liquid crystal composition of the present invention may vary widely, such as about 60 ° -140 ° C., and is characterized in particular by low temperatures. In this way, the nematic liquid crystal phase temperature range of the Np-liquid crystal composition obtained by mixing the compound of formula (I) is wider than the nematic liquid crystal phase temperature range of each component constituting the liquid crystal composition and is wider at low temperature. . The Np-liquid crystal composition of the present invention was found to be useful as a liquid crystal material of a FEM type display device.
다음에 실시예를 통하여 본 발명을 좀더 상세히 설명한다.Next, the present invention will be described in more detail with reference to the following Examples.
[실시예]EXAMPLE
화합물(1)과 화합물(2)를 같은 량으로 해서 180℃에서 가열하여 등방성 액체로 하고 그후에 교반 혼합하여 그 네마틱 액정상 온도범위가 91.5-142℃가 되는 Np-액정조성물을 만든다. 이와같이 p-시아노신나민산-p′-n-알콕시페닐에스테르의 2종류 이상을 혼합해서 Np-액정조성물을 만든다. 이와같이 해서 만든 Np-액정조성물의 네마틱 액정상 온도범위를 제2표에 기록한다. 제2표 중의 KN점 및 NI점은 제1표와 같은 의미를 갖는다.Compound (1) and compound (2) in the same amount are heated at 180 캜 to form an isotropic liquid and then stirred and mixed to form an Np-liquid crystal composition having a nematic liquid crystal phase temperature range of 91.5-142 캜. In this way, two or more kinds of p-cyanocinnamic acid-p'-n-alkoxyphenyl esters are mixed to form an Np-liquid crystal composition. The nematic liquid crystal phase temperature range of the Np-liquid crystal composition thus produced is recorded in the second table. The KN point and NI point in 2nd table have the same meaning as the 1st table | surface.
[제2표][Table 2]
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR7601344A KR800000594B1 (en) | 1976-06-01 | 1976-06-01 | Nematic liquid crystal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR7601344A KR800000594B1 (en) | 1976-06-01 | 1976-06-01 | Nematic liquid crystal composition |
Publications (1)
Publication Number | Publication Date |
---|---|
KR800000594B1 true KR800000594B1 (en) | 1980-06-30 |
Family
ID=19202326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR7601344A KR800000594B1 (en) | 1976-06-01 | 1976-06-01 | Nematic liquid crystal composition |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR800000594B1 (en) |
-
1976
- 1976-06-01 KR KR7601344A patent/KR800000594B1/en active
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6306271B2 (en) | Liquid crystal compound having difluoromethoxy crosslink, composition and application thereof | |
KR800000594B1 (en) | Nematic liquid crystal composition | |
US4058475A (en) | Liquid crystal compositions containing cyanocinnamic acid esters | |
JPS6019756A (en) | Propiol nitrile compound | |
JPS60136555A (en) | Ester of 4-isothiocyanatophenol | |
KR800000595B1 (en) | Nematic liquid crystal composition | |
JPH0239497B2 (en) | 44 * TORANSUU4 ** ARUKIRUSHIKUROHEKISHIRU * ANSOKUKOSAN2 * 44JIHAROGENOFUENIRUESUTERU | |
JPS63284147A (en) | Liquid crystal substance, its production and liquid crystal composition containing said substance | |
JPH0680612A (en) | Optically inactive liquid crystal compound | |
JPH039895B2 (en) | ||
JPH0150693B2 (en) | ||
JPS60222458A (en) | P-substituted phenylisothiocyanate | |
US5210267A (en) | Optically-active aliphatic β-halogen substituted carboxylic acid 4'-(4-alkoxybenzyloxy)biphenyl thioester compounds and process for the preparation thereof | |
JPS58126840A (en) | 4-(trans-4'-alkylcyclohexyl)benzoic acid 3-halogeno-phenyl ester | |
JPS58126838A (en) | 4-(trans-4'-alkylcyclohexyl)benzoic acid 3-chloro-4-halogenophenyl ester | |
JPH0150691B2 (en) | ||
US4058476A (en) | Liquid crystalline isonitriles | |
JPS59172452A (en) | Optically active substance having negative dielectric anisotropic value | |
JP4208292B2 (en) | Alkoxyethyltolane compounds | |
JPS6136256A (en) | Liquid crystal compound and liquid crystal composition | |
JPS5921651A (en) | Ester derivative of 4'-fluorophenyl 2-chloro-4- hydroxybenzoate | |
JPH01245089A (en) | Liquid crystal material | |
JPS6023476A (en) | 4-(substituted carbonyloxy)biphenylyl-4'-carboxylic acid alkyl ester | |
JPS60188358A (en) | Propyne nitrile derivative | |
JPS6110533A (en) | Liquid crystal esters and their composition |