JP2573038B2 - Alkynyl oxytran compounds - Google Patents
Alkynyl oxytran compoundsInfo
- Publication number
- JP2573038B2 JP2573038B2 JP23299788A JP23299788A JP2573038B2 JP 2573038 B2 JP2573038 B2 JP 2573038B2 JP 23299788 A JP23299788 A JP 23299788A JP 23299788 A JP23299788 A JP 23299788A JP 2573038 B2 JP2573038 B2 JP 2573038B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- alkynyl
- compounds
- oxytran
- 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
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- 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トラン化
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
に有用なアルキニルオキシトラン化合物に関するもので
ある。Description: TECHNICAL FIELD The present invention relates to a tolan compound useful as an electro-optical display material. More specifically, the present invention is useful for increasing the anisotropy of the refractive index of a liquid crystal material by mixing it with an STN type liquid crystal material. Alkynyl oxitrane compounds.
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を示すトラン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. Conventionally, ferroelectric liquid crystal has been studied as a high-speed response, but a high-speed response is expected by making the thickness of the STN-type liquid crystal cell thinner. In this case, a liquid crystal material having a large refractive index anisotropy (Δn) of the liquid crystal material to be filled in the cell is required. As a typical example, a trans compound having a low viscosity and a high Δn has been proposed, but is still insufficient. And a compound exhibiting 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キニルオキシトラ
ン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 exhibiting n, it was found that the addition of a novel alkynyloxytran compound represented by the following general formula (I) to a liquid crystal significantly improved the Δn of the liquid crystal. .
（式中、Ｒは炭素原子数３〜18のアルキニル基を示し、
Ｒ′は炭素原子数１〜18のアルキル基を示す。） 本発明になる上記一般式（Ｉ）で表される化合物にお
いて、Ｒで示されるアルキニル基としては、例えば、１
−プロピニル、１−ブチニル、２−ブチニル、１−ペン
チニル、２−ペンチニル、１−ヘキシニル、４−ヘプチ
ニル、６−オクチニル、６−ノニニル、７−ノニニル、
８−ウンデシニル、10−トリデシニル、12−ペンタデシ
ニル等があげられ、Ｒ′で示されるアルキル基として
は、例えば、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、ドデシル、テトラデシル、ヘキサデシル、オクタデ
シル等があげられる。 (Wherein, R represents an alkynyl group having 3 to 18 carbon atoms,
R 'represents an alkyl group having 1 to 18 carbon atoms. In the compound represented by the above general formula (I) according to the present invention, the alkynyl group represented by R includes, for example, 1
-Propynyl, 1-butynyl, 2-butynyl, 1-pentynyl, 2-pentynyl, 1-hexynyl, 4-heptynyl, 6-octynyl, 6-noninyl, 7-noninyl,
8-undecynyl, 10-tridecynyl, 12-pentadecynyl and the like, and examples of the alkyl group represented by R ′ include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, Tetradecyl, hexadecyl, octadecyl and the like can be mentioned.
また、上記一般式（Ｉ）で表される化合物は、Ｒ−CH
2−CHで表されるアルコールと４−アルキル−４′−ヒ
ドロキシトランとを反応させることにより製造すること
ができる。Further, the compound represented by the above general formula (I) is a compound represented by R-CH
It can be produced by reacting an alcohol represented by 2- CH with 4-alkyl-4'-hydroxytolan.
かくして得られる本発明のアルキニルオキシトラン化
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、液晶化合物として周知のアルキルトラン化合
物を得るための中間体として有用である。The alkynyloxytran compound of the present invention thus obtained 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
Because of their excellent reactivity, they are useful as various synthetic intermediates, and particularly useful as intermediates for obtaining alkyltran compounds known as liquid crystal compounds.
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−ｎ−プロピル−４′−（２−ブチニルオキシ）トラ
ンの合成 ４−ｎ−プロピル−４′−ヒドロキシトラン1.00g、
２−ブチン−１−オール0.36gおよびトリフェニルホス
フィン1.22gをエーテル10に溶解し、ここにアゾジカル
ボン酸ジエチルエステル0.81gを滴下した。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
／ジエチルエーテル（8/2）を展開溶媒としてシリカゲ
ルカラムにより精製した後、ｎ−ヘキサンで再結晶して
融点85.7℃の白色結晶0.67gを得た。Example 1 Synthesis of 4-n-propyl-4 '-(2-butynyloxy) tolan 1.00 g of 4-n-propyl-4'-hydroxytolan,
0.36 g of 2-butyn-1-ol and 1.22 g of triphenylphosphine were dissolved in ether 10, and 0.81 g of diethyl azodicarboxylate was added dropwise thereto. After stirring at room temperature for 3 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 / diethyl ether (8/2) as a developing solvent, and recrystallized from n-hexane to obtain 0.67 g of white crystals having a melting point of 85.7 ° 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.
2975cm-1、1600cm-1、1575cm-1、1570cm-1、 1260cm-1、1050cm-1、840cm-1 実施例２ ４−ｎ−プロピル−４′−（２−ペンチニルオキシ）ト
ランの合成 ２−ブチン−１−オールに代えて２−ペンチン−１−
オールを用いる他は実施例１と同様に操作し、融点67.8
℃の白色結晶の生成物0.62gを得た。 2975cm -1, 1600cm -1, 1575cm -1 , 1570cm -1, 1260cm -1, 1050cm -1, 840cm -1 Example 2 4-n-propyl-4 '- (2-pentynyloxy) Tran Synthesis of 2-pentyn-1- instead of 2-butyn-1-ol
The same operation as in Example 1 was carried out except using oar, melting point 67.8.
0.62 g of the product as white crystals at ℃ was obtained.
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.
2975cm-1、1600cm-1、1575cm-1、1570cm-1、 1260cm-1、1050cm-1、840cm-1 参考例 本発明になる新規なアルキニルオキシトラン化合物を
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、次の蘇生になる1:1:1の混合物に10％の
トラン化合物を混合し て、それぞれのΔｎの変化を測定し、その結果を次に示
した。 2975cm -1, 1600cm -1, 1575cm -1 , 1570cm -1, 1260cm -1, 1050cm -1, by adding a new alkynyloxy tolans becomes 840 cm -1 Reference Example present invention to a liquid crystal, the liquid crystal of Δn Mix with 10% tolane compound in 1: 1: 1 mixture to be the next resuscitation to see improving Then, the change of each Δn was measured, and the results are shown below.
上の結果から明らかなように、本発明になる新規なア
ルキニルオキシトラン化合物は、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 alkynyloxytran compound according to the present invention has an effect of increasing the value of Δn of the mother liquid crystal.
Claims (1)
キシトラン化合物。 （式中、Ｒは炭素原子数３〜18のアルキニル基を示し、
Ｒ′は炭素原子数１〜18のアルキル基を示す。）1. An alkynyl oxitrane compound represented by the following general formula (I). (Wherein, R represents an alkynyl group having 3 to 18 carbon atoms,
R 'represents an alkyl group having 1 to 18 carbon atoms. )
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23299788A JP2573038B2 (en) | 1988-09-16 | 1988-09-16 | Alkynyl oxytran compounds |
| US07/397,036 US5047169A (en) | 1988-09-16 | 1989-08-21 | Tolane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23299788A JP2573038B2 (en) | 1988-09-16 | 1988-09-16 | Alkynyl oxytran compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0283346A JPH0283346A (en) | 1990-03-23 |
| JP2573038B2 true JP2573038B2 (en) | 1997-01-16 |
Family
ID=16948185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23299788A Expired - Lifetime JP2573038B2 (en) | 1988-09-16 | 1988-09-16 | Alkynyl oxytran compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2573038B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047169A (en) * | 1988-09-16 | 1991-09-10 | Adeka Argus Chemical Co., Ltd. | Tolane compound |
| US6149997A (en) * | 1992-01-30 | 2000-11-21 | Baxter International Inc. | Multilayer coextruded material for medical grade products and products made therefrom |
-
1988
- 1988-09-16 JP JP23299788A patent/JP2573038B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0283346A (en) | 1990-03-23 |
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Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
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| EXPY | Cancellation because of completion of term |