JP2691766B2 - Alkenoxy cyanobiphenyl compound - Google Patents
Alkenoxy cyanobiphenyl compoundInfo
- Publication number
- JP2691766B2 JP2691766B2 JP1052725A JP5272589A JP2691766B2 JP 2691766 B2 JP2691766 B2 JP 2691766B2 JP 1052725 A JP1052725 A JP 1052725A JP 5272589 A JP5272589 A JP 5272589A JP 2691766 B2 JP2691766 B2 JP 2691766B2
- Authority
- JP
- Japan
- Prior art keywords
- alkenoxy
- liquid crystal
- compound
- methyl
- cyanobiphenyl 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】 本発明は、電気光学的表示材料として有用なアルケノ
キシシアノビフェニル化合物に関し、さらに詳しくは、
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に有用なアルケノキシシアノビ
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 alkenoxycyanobiphenyl compound useful as an electro-optical display material, and more specifically,
The present invention relates to an alkenoxy cyanobiphenyl compound useful for increasing the anisotropy of the refractive index of a liquid crystal material by mixing it with an STN type liquid crystal material.
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を示すシアノビフェニル化合物が提案さ
れたがまだ不十分であり、さらに高いΔｎを示す化合物
が望まれていた。At present, STN-type liquid crystal cells are being developed toward black-and-white and full-color modes from green or blue mode, and at the same time, studies are underway on high-speed response to moving image support. As a high-speed response, ferroelectric liquid crystals have been studied, but a high-speed response can be expected by making the thickness of the STN-type liquid crystal cell thinner. In that case,
A liquid crystal material having a large anisotropy (Δn) in the refractive index of the liquid crystal material filled in the cell is required. As a representative example, a cyanobiphenyl compound having low viscosity and high Δn has been proposed, but it is still insufficient. However, a compound having a higher Δn has been desired.
本発明者等は、上記現状に鑑み、低粘度にして高いΔ
ｎを示す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）で表される新規なアルケノキシシアノビ
フェニル化合物を液晶に添加することにより、液晶のΔ
ｎを著しく改良することを見出した。In view of the above-mentioned situation, the present inventors have set a low viscosity and a high Δ
As a result of intensive studies to find a compound showing n, the addition of a novel alkenoxycyanobiphenyl compound represented by the following general formula (I)
It has been found that n is significantly improved.
（式中、Ｒは３−メチル−２−ブテニルオキシ基または
３−メチル−３−ブテニルオキシ基を示し。） また、上記一般式（Ｉ）で表される化合物は、Ｒ−OH
で表されるアルケニルアルコールと４−シアノ−４′−
ヒドロキシ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。 (In the formula, R represents a 3-methyl-2-butenyloxy group or a 3-methyl-3-butenyloxy group.) Further, the compound represented by the general formula (I) is R-OH.
Alkenyl alcohol and 4-cyano-4'-
It can be produced by reacting with hydroxybiphenyl.
かくして得られる本発明のアルケノキシヒアノビフェ
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に有用なばかりで
なく、反応性に優れるため、各種の合成中間体として有
用であり、特に、液晶中間体として有用である。The thus-obtained alkenoxy hyanobiphenyl compound of the present invention 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 reactivity, so It is useful as a synthetic intermediate, and particularly useful as a liquid crystal intermediate.
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 described in more detail with reference to examples.
実施例１ ４−シアノ−４′−（３″−メチル−２″−ブテニルオ
キシ）ビフェニルの合成 ３−メチル−２−ブテン−１−オール1.14g、４−シ
アノ−４′−ヒドロキシビフェニル2.34gおよびトリフ
ェニルホスフィン3.77gを乾燥エチルエーテル30mlに溶
解し、ここにアゾジカルボン酸ジイソプロピル2.91gを
同量の乾燥エチルエーテルとともに滴下した。室温で３
時間撹拌し、析出したトリフェニルホスフィンオキシド
をろ別した後、ろ液を脱溶媒した。残留物をｎ−ヘキサ
ン／エチルエーテル（93/7）を展開溶媒としてシリカゲ
ルカラムにより精製した後、メタノール／エタノール
（8/1）で再結晶して融点79.0℃の目的物0.7gを得た。Example 1 Synthesis of 4-cyano-4 '-(3 "-methyl-2" -butenyloxy) biphenyl 3-Methyl-2-buten-1-ol (1.14 g), 4-cyano-4'-hydroxybiphenyl (2.34 g) and triphenylphosphine (3.77 g) were dissolved in dry ethyl ether (30 ml), and diisopropyl azodicarboxylate (2.91 g) was added thereto. Dropwise with a quantity of dry ethyl ether. 3 at room temperature
After stirring for hours, the precipitated triphenylphosphine oxide was filtered off, and the filtrate was desolvated. The residue was purified by a silica gel column using n-hexane / ethyl ether (93/7) as a developing solvent and then recrystallized from methanol / ethanol (8/1) to obtain 0.7 g of the desired product having a melting point of 79.0 ° C.
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 spectroscopy, the obtained product had the following characteristic absorption and was confirmed to be the desired product.
2900cm-1、2230cm-1、1600cm-1、1495cm-1、 1245cm-1、1000cm-1、825cm-1、570cm-1、 535cm-1 実施例２ ４−シアノ−４′−（３″−メチル−３−ブテニルオキ
シ）ビフェニルの合成 ３−メチル−３−ブテン−１−オール1.14g、４−シ
アノ−４′−ヒドロキシビフェニル2.34gおよびトリフ
ェニルホスフィン3.77gを乾燥テトラヒドロフラン30ml
に溶解し、ここにアドジカルボン酸ジイソプロピル2.91
gを同量の乾燥テトラヒドロフランの溶液を滴下した。
室温で３時間撹拌した後、析出したトリフェニルホスフ
ィンオキシドをエチルエーテルで抽出してろ別した。ろ
液を脱溶媒し、残渣を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精製した。
さらにメタノール/n−ヘキサン（1/1）で再結晶して融
点45.5℃の目的物2.4gを得た。 2900cm -1, 2230cm -1, 1600cm -1 , 1495cm -1, 1245cm -1, 1000cm -1, 825cm -1, 570cm -1, 535cm -1 Example 2 4-Cyano-4 '- (3 "- methyl Synthesis of -3-butenyloxy) biphenyl 3-methyl-3-buten-1-ol 1.14 g, 4-cyano-4'-hydroxybiphenyl 2.34 g and triphenylphosphine 3.77 g were dried on tetrahydrofuran 30 ml.
Dissolved in diisopropyl addicarboxylate 2.91
A solution of dry tetrahydrofuran in the same amount as g was added dropwise.
After stirring at room temperature for 3 hours, the precipitated triphenylphosphine oxide was extracted with ethyl ether and filtered. The filtrate was desolvated, and the residue was purified by a silica gel column using n-hexane / ethyl ether (9/1) as a developing solvent.
Recrystallization from methanol / n-hexane (1/1) gave 2.4 g of the desired product having a melting point of 45.5 ° C.
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 spectroscopy, the obtained product had the following characteristic absorption and was confirmed to be the desired product.
2925cm-1、2225cm-1、1605cm-1、1250cm-1、 1185cm-1、1040cm-1、830cm-1、570cm-1、 535cm-1 参考例 本発明になる新規なアルケノ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、次の組成になる1:1:1を混合した
母液晶に20％のアルケ ノキシシアノビフェニル化合物を混合して、25℃におけ
るそれぞれのΔｎの変化を測定し、その結果を次に示し
た。 2925cm -1, 2225cm -1, 1605cm -1 , 1250cm -1, 1185cm -1, 1040cm -1, 830cm -1, 570cm -1, the novel alkenoxy cyanobiphenyl compounds would 535cm -1 Example present invention In order to see that the Δn of the liquid crystal is improved by adding it to the liquid crystal, a mother liquid crystal mixed with 1: 1: 1 having the following composition has a 20% The changes in Δn at 25 ° C. were measured by mixing the noxycyanobiphenyl compounds, and the results are shown below.
上の結果から明らかなように、本発明になる新規なア
ルケノキシ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 novel alkenoxy cyanobiphenyl compound according to the present invention has an effect of increasing the Δn value of the mother liquid crystals.
フロントページの続き (56)参考文献 特開 平２−69428（ＪＰ，Ａ) 特開 昭63−280741（ＪＰ，Ａ) 特開 昭63−273648（ＪＰ，Ａ) 特開 昭61−145154（ＪＰ，Ａ) 特開 昭62−286943（ＪＰ，Ａ) 特開 昭63−310859（ＪＰ，Ａ) Ｊ．Ｐｏｌｘｍ．Ｓｃｉ．，Ｐａｒｔ Ａ：Ｐｏｌｙｍ．Ｃｈｅｍ．，25〔９〕 （1987） Ｐ．2425−2445Continuation of front page (56) Reference JP-A-2-69428 (JP, A) JP-A-63-280741 (JP, A) JP-A-63-273648 (JP, A) JP-A-61-145154 (JP , A) JP 62-286943 (JP, A) JP 63-310859 (JP, A) J. Polxm. Sci. , Part A: Polym. Chem. , 25 [9] (1987) P. 2425-2445
Claims (1)
シアノビフェニル化合物。 （式中、Ｒは３−メチル−２−ブテニルオキシ基または
３−メチル−３−ブテニルオキシ基を示す。）1. An alkenoxy cyanobiphenyl compound represented by the following general formula (I). (In the formula, R represents a 3-methyl-2-butenyloxy group or a 3-methyl-3-butenyloxy group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1052725A JP2691766B2 (en) | 1989-03-03 | 1989-03-03 | Alkenoxy cyanobiphenyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1052725A JP2691766B2 (en) | 1989-03-03 | 1989-03-03 | Alkenoxy cyanobiphenyl compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02231460A JPH02231460A (en) | 1990-09-13 |
| JP2691766B2 true JP2691766B2 (en) | 1997-12-17 |
Family
ID=12922899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1052725A Expired - Lifetime JP2691766B2 (en) | 1989-03-03 | 1989-03-03 | Alkenoxy cyanobiphenyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2691766B2 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61145154A (en) * | 1984-12-20 | 1986-07-02 | Asahi Glass Co Ltd | Liquid crystal compound and composition |
| JPS62286943A (en) * | 1986-06-06 | 1987-12-12 | Dainippon Ink & Chem Inc | 4'-substituted biphenyl crotyl ether derivative |
| JPH0791258B2 (en) * | 1987-06-10 | 1995-10-04 | 旭電化工業株式会社 | Optically active cyanobiphenyl compound |
| JPS63273648A (en) * | 1987-04-30 | 1988-11-10 | Kuraray Co Ltd | Production of side-chain-type polymer liquid crystal |
| JP2543700B2 (en) * | 1987-05-14 | 1996-10-16 | 東レ・ダウコーニング・シリコーン株式会社 | Liquid crystalline organopolysiloxane and method for producing the same |
| JPH0269428A (en) * | 1988-09-06 | 1990-03-08 | Idemitsu Kosan Co Ltd | Liquid crystal compound and liquid crystal polymer |
-
1989
- 1989-03-03 JP JP1052725A patent/JP2691766B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Ｊ．Ｐｏｌｘｍ．Ｓｃｉ．，ＰａｒｔＡ：Ｐｏｌｙｍ．Ｃｈｅｍ．，２５〔９〕 （１９８７） Ｐ．２４２５−２４４５ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02231460A (en) | 1990-09-13 |
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