JPH02160756A - Octadienyloxycyanobiphenyl compound - Google Patents
Octadienyloxycyanobiphenyl compoundInfo
- Publication number
- JPH02160756A JPH02160756A JP31579888A JP31579888A JPH02160756A JP H02160756 A JPH02160756 A JP H02160756A JP 31579888 A JP31579888 A JP 31579888A JP 31579888 A JP31579888 A JP 31579888A JP H02160756 A JPH02160756 A JP H02160756A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- cyanobiphenyl
- crystal material
- useful
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 15
- -1 4'-Cyanobiphenyl compound Chemical class 0.000 claims description 4
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 24
- 239000000463 material Substances 0.000 abstract description 9
- ZRMIETZFPZGBEB-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzonitrile Chemical group C1=CC(O)=CC=C1C1=CC=C(C#N)C=C1 ZRMIETZFPZGBEB-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 241001164374 Calyx Species 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- YHYGSIBXYYKYFB-VOTSOKGWSA-N (2e)-octa-2,7-dien-1-ol Chemical compound OC\C=C\CCCC=C YHYGSIBXYYKYFB-VOTSOKGWSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 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
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring 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】
本発明は、オクタジェニルオキシシアノビフェニル化合
物に関し、さらに詳しくは、液晶組成物に対する溶解性
に優れ、しかも液晶相を低温度までに広げることのでき
る液晶材料として有用な、４−オクタジエニルオキシ−
４゛−シアノビフェニル化合物に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an octagenyloxycyanobiphenyl compound, and more specifically, it is useful as a liquid crystal material that has excellent solubility in liquid crystal compositions and can extend the liquid crystal phase to low temperatures. , 4-octadienyloxy-
This relates to a 4'-cyanobiphenyl compound.
現在、ＳＴＮ型液晶セルはグリーンまたはブルーモード
より白黒、フルカラー化へ向けて開発が進められており
、それと併行して動画対応への高速応答化の検討が進め
られている。高速応答としては、従来、強誘電性液晶が
研究されているが、ＳＴＮ型液晶セルの層の厚さをより
薄くする事により、高速応答が期待される。その場合、
セルに充填される液晶材料の屈折率の異方性（Δｎ）の
大きな液晶材料が必要となり、その代表例として低粘性
にして高いΔｎを示すアルコキシシアノビフェニル化合
物が提案されたが、まだ不充分でありさらに高いΔｎを
示ししかも溶解性に優れた化合物が望まれていた。Currently, STN type liquid crystal cells are being developed from green or blue mode to monochrome and full color, and at the same time, studies are underway to increase the speed of response to support moving images. As for high-speed response, ferroelectric liquid crystals have been studied so far, but high-speed response is expected by making the layer thickness of the STN liquid crystal cell thinner. In that case,
A liquid crystal material with a large refractive index anisotropy (Δn) is required to fill the cell, and alkoxycyanobiphenyl compounds that have low viscosity and a high Δn have been proposed as a typical example, but it is still insufficient. Therefore, a compound that exhibits even higher Δn and has excellent solubility has been desired.
本発明者等は、上記現状に鑑み、低粘度にして高いΔｎ
を示し、しかも液晶組成物に対する溶解性に優れた化合
物を見出すべく鋭意検討を重ねた結果、次の式（１）で
表される新規な４−オクタジエニルオキシ−４゛−シア
ノビフェニル化合物を液晶に添加することにより、液晶
のΔｎを著しく改良し、しかも溶解性に優れることを見
出した。In view of the above-mentioned current situation, the inventors of the present invention have developed a method that has a low viscosity and a high Δn.
As a result of extensive research to find a compound that exhibits the following properties and has excellent solubility in liquid crystal compositions, we have discovered a novel 4-octadienyloxy-4'-cyanobiphenyl compound represented by the following formula (1). It has been found that by adding it to liquid crystals, the Δn of the liquid crystals is significantly improved and the solubility is excellent.
上記式（Ｉ）で表される化合物は、２．７−オクタジエ
ン−１−オールと４−ヒドロキシ−４°−シアノビフェ
ニルとを反応させることにより製造することができる。The compound represented by the above formula (I) can be produced by reacting 2,7-octadien-1-ol and 4-hydroxy-4°-cyanobiphenyl.
かくして得られる本発明のオクタジェニルオキシシアノ
ビフェニル化合物はＳＴＮ型液晶材料に混合することに
よって液晶材料の屈折率の異方性を大きくするのに有用
なばかりでなく、溶解性に優れるため、各種の合成中間
体として有用であり、さらに液晶相を低温度まで広げ、
正の誘電異方性を有する液晶として有用である。The octagenyloxycyanobiphenyl compound of the present invention obtained in this way is not only useful for increasing the anisotropy of the refractive index of the liquid crystal material by mixing it with the STN type liquid crystal material, but also has excellent solubility, so it can be used for various purposes. It is useful as a synthetic intermediate for
It is useful as a liquid crystal with positive dielectric anisotropy.
以下、実施例によって本発明を更に詳細に説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
２．７−オクタレニン−１−オール０．４２ ｇ （
０，００３３モル）、４−ヒドロキシ−４″〜シアノビ
フェニル０．５９ ｇ （０，００３モル）、トリフェ
ニルホスフィン０．９４ｇを乾燥テトラヒドロフラン１
０１ｄに溶解し、ここにアゾジカルボン酸ジエチルエス
テル０．７３ｇを同量の乾燥テトラヒドロフランと共に
約１０分で滴下した。室温で３時間半撹拌した後、ｎ
−ヘキサン／エチルエーテル（９／１）１５ｄおよびシ
リカゲルＩｇを用いて、生成したトリフェニルホスフィ
ンオキシトの抽出をおこない、ろ過、ろ液の脱溶媒をお
こなった。残留物をｎ−ヘキサン／エチルエーテル（９
／１）を展開溶媒としてシリカゲルカラムにより精製し
て白色結晶０．７ｇを得た。Example 1 2.7-octarenin-1-ol 0.42 g (
0,0033 mol), 0.59 g (0,003 mol) of 4-hydroxy-4''~cyanobiphenyl, and 0.94 g of triphenylphosphine in dry tetrahydrofuran 1
01d, and 0.73 g of azodicarboxylic acid diethyl ester was added dropwise thereto over about 10 minutes together with the same amount of dry tetrahydrofuran. After stirring at room temperature for 3 and a half hours, n
The generated triphenylphosphine oxyto was extracted using -hexane/ethyl ether (9/1) 15d and silica gel Ig, followed by filtration and desolvation of the filtrate. The residue was dissolved in n-hexane/ethyl ether (9
/1) was purified using a silica gel column as a developing solvent to obtain 0.7 g of white crystals.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
２９２０ｃｒ’（ｓ） 、 ２２２５ｃ＋ａ−’（ｓ
） 、 １６０２ｃｍ−’（ｓ） 、１４９０ｃｍ
−’（ｓ） 、１２４５ｃｍ−’（ｓ） 、１１８０ｃ
ｍ−’（ｓ）、８１２ｃｍ−’ （ｓ）
この化合物を二枚のガラス板間にはさみ、偏光顕微鏡に
よる相形態観察およびＤＳＣ熱量変化の測定を行なった
結果、以下の相転移を確認した。2920cr'(s), 2225c+a-'(s
), 1602cm-'(s), 1490cm
-'(s), 1245cm-'(s), 1180c
m-' (s), 812 cm-' (s) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope and the DSC calorific value change was measured. As a result, the following phase transition was confirmed.
本発明化合物とＭ４Ｑする次の式で表される４−オクチ
ルオキシ−４°−シアノビフェニル化合物の相形態観察
を同様にして行なった結果、以下の相転移を確認した。Observation of the phase morphology of the 4-octyloxy-4°-cyanobiphenyl compound represented by the following formula in M4Q with the compound of the present invention was conducted in the same manner, and the following phase transition was confirmed.
Ｃｒｙ 辷：萼Ｓ 辷＝萼Ｎ 辷＝萼１ ｓ。Cry Calyx: Calyx S Calyx N Calyx N Calyx 1 s.
５４．５ ６７ ８０’Ｃ
上の結果から明らかなように、本発明になるオクタジェ
ニルオキシシアノビフェニル化合物は、液晶相を低温度
まで広げることができ、液晶材料として有用な化合物で
ある。54.5 67 80'C As is clear from the above results, the octagenyloxycyanobiphenyl compound of the present invention can extend the liquid crystal phase to low temperatures, and is a compound useful as a liquid crystal material.
参考例
本発明になる新規なオクタジェニルオキシシアノビフェ
ニル化合物を液晶に添加することにより、液晶のΔｎを
改良することを見るために、次の三種のエステル系化合
物の１：１：１混合液晶組成物のΔｎおよびこの組成物
にさらに本発明化合物を２０％混合した液晶組成物のΔ
ｎを測定し、その結果を次に示した。Reference Example In order to demonstrate that Δn of a liquid crystal can be improved by adding the novel octagenyloxycyanobiphenyl compound of the present invention to a liquid crystal, a 1:1:1 mixed liquid crystal of the following three types of ester compounds was prepared. Δn of the composition and Δ of a liquid crystal composition obtained by further mixing 20% of the compound of the present invention with this composition.
n was measured and the results are shown below.
上の結果から明らかなように、本発明になる４−オクタ
ジエニルオキシ−４°−シアノビフェニル化合物は、母
液晶のΔｎの値を大きくする効果が見られる。As is clear from the above results, the 4-octadienyloxy-4°-cyanobiphenyl compound of the present invention has the effect of increasing the value of Δn of the mother liquid crystal.
Claims (1)
４’−シアノビフェニル化合物。 ▲数式、化学式、表等があります▼（ I ）[Claims] 4-octadienyloxy- represented by the following formula (I)
4'-Cyanobiphenyl compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31579888A JPH02160756A (en) | 1988-12-14 | 1988-12-14 | Octadienyloxycyanobiphenyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31579888A JPH02160756A (en) | 1988-12-14 | 1988-12-14 | Octadienyloxycyanobiphenyl compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02160756A true JPH02160756A (en) | 1990-06-20 |
Family
ID=18069681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31579888A Pending JPH02160756A (en) | 1988-12-14 | 1988-12-14 | Octadienyloxycyanobiphenyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02160756A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0563982A2 (en) * | 1992-04-03 | 1993-10-06 | Chisso Corporation | Polycyclic diene derivatives |
-
1988
- 1988-12-14 JP JP31579888A patent/JPH02160756A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0563982A2 (en) * | 1992-04-03 | 1993-10-06 | Chisso Corporation | Polycyclic diene derivatives |
| EP0563982A3 (en) * | 1992-04-03 | 1994-01-19 | Chisso Corp | |
| US5449810A (en) * | 1992-04-03 | 1995-09-12 | Chisso Corporation | Diene derivative |
| US5609791A (en) * | 1992-04-03 | 1997-03-11 | Chisso Corporation | Diene derivative |
| US5662830A (en) * | 1992-04-03 | 1997-09-02 | Chisso Corporation | Diene derivative |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4228029A (en) | Liquid crystalline compositions | |
| JPS6144863B2 (en) | ||
| JPS63165371A (en) | Pyrimidine compound | |
| JPH02160756A (en) | Octadienyloxycyanobiphenyl compound | |
| US4980083A (en) | Optically active compound and liquid crystal composition containing the same | |
| JP2739082B2 (en) | Isopentenyl oxytran compound | |
| JP2573038B2 (en) | Alkynyl oxytran compounds | |
| JPS6019756A (en) | Propiol nitrile compound | |
| JPH02207056A (en) | Alkoxytolan compound | |
| JPS6388165A (en) | Liquid crystal | |
| JPH02231460A (en) | Alkenoxycyanobiphenyl compound | |
| JPH0311039A (en) | Novel aromatic arboxylic acid ester compound | |
| JP2853710B2 (en) | Method for producing phenylcyclohexylcyclohexanone derivative | |
| JPS6168447A (en) | Phenoxyacetic acid ester derivative | |
| JP4023887B2 (en) | Ester compound and liquid crystal composition containing the same | |
| JPS6032722A (en) | 6,6'-disubstituted-2,2'-binaphthyl | |
| JP2748025B2 (en) | Alkynyloxyphenylcyclohexane compound | |
| JPS6341446A (en) | Novel liquid crystal compound and liquid crystal composition | |
| EP0430205A2 (en) | Liquid cristal display device | |
| JPS60197637A (en) | Beta-(4-substituted phenyl)propionic acid phenyl ester derivative | |
| JPH02142751A (en) | Optically active ester compound and liquid crystal composition containing the same | |
| JPS60202830A (en) | Novel phenylalkylacetylene based nematic liquid crystal compound | |
| JPS6383191A (en) | Liquid crystal material | |
| JPH0311029A (en) | Alkoxy-alpha-methylallylbenzenes | |
| JPH03178967A (en) | Pyrimidine derivative |