JPH111445A - Diacetylene compound, liquid crystal composition containing the same and liquid crystal element using the same - Google Patents
Diacetylene compound, liquid crystal composition containing the same and liquid crystal element using the sameInfo
- Publication number
- JPH111445A JPH111445A JP9156598A JP15659897A JPH111445A JP H111445 A JPH111445 A JP H111445A JP 9156598 A JP9156598 A JP 9156598A JP 15659897 A JP15659897 A JP 15659897A JP H111445 A JPH111445 A JP H111445A
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- Prior art keywords
- liquid crystal
- group
- compound
- phenylene
- independently
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、液晶表示素子の構
成材料あるいは液晶組成物の配合成分として有用なジア
セチレン化合物、それを含む液晶組成物およびそれを用
いた液晶素子に関する。The present invention relates to a diacetylene compound useful as a constituent material of a liquid crystal display device or a compounding component of a liquid crystal composition, a liquid crystal composition containing the same, and a liquid crystal device using the same.
【０００２】[0002]
【従来の技術】近年、液晶表示素子の高性能化は、情報
化社会の進展に伴い不可欠となっている。液晶組成物の
物性の中で、より高速化、あるいは高性能化のために
は、屈折率異方性の大きい材料が必要とされている。し
かしながら、これまで十分大きな屈折率異方性を有する
材料は見出されていない。2. Description of the Related Art In recent years, higher performance of liquid crystal display elements has become indispensable with the progress of the information society. Among the physical properties of the liquid crystal composition, a material having a large refractive index anisotropy is required for higher speed or higher performance. However, a material having a sufficiently large refractive index anisotropy has not been found so far.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、大きい屈折
率異方性を有する化合物、これを用いた液晶組成物およ
びこれを用いた、光シャッタ―や表示素子などに使用で
きる液晶素子を提供することを目的とする。SUMMARY OF THE INVENTION The present invention provides a compound having a large refractive index anisotropy, a liquid crystal composition using the compound, and a liquid crystal device using the compound which can be used for an optical shutter or a display device. The purpose is to do.
【０００４】[0004]
【課題を解決するための手段】上記の課題を解決するた
め、本発明者らは鋭意検討を加えた結果、ある種のジア
セチレン化合物が十分大きな屈折率異方性を有すること
を見出し、本発明を完成するに至った。即ち、本発明
は、下記一般式（１）Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have conducted intensive studies and as a result, have found that a certain diacetylene compound has a sufficiently large refractive index anisotropy. The invention has been completed. That is, the present invention provides the following general formula (1)
【０００５】[0005]
【化３】 Embedded image
【０００６】［式中、ＡおよびＢは、それぞれ独立に、Wherein A and B are each independently:
【０００７】[0007]
【化４】 Embedded image
【０００８】を表し、ｌおよびｍは、それぞれ独立に、
０または１を表し、同時に０を表さない。ＥおよびＧ
は、それぞれ独立に、フッ素原子、メチル基またはメト
キシ基を表し、ｎは０〜４の整数、ｏおよびｐは０〜３
の整数である。Ｒ1およびＲ2は、それぞれ独立に、水素
原子、フッ素原子、トリフルオロメチル基、１から３個
のフッ素原子で置換されていてもよいメトキシ基、１か
ら５個のフッ素原子で置換されていてもよいエトキシ
基、シアノ基、４−Ｒ−（シクロアルキル）基、４−Ｒ
−（シクロアルケニル基）またはＲ−（Ｏ）ｑ基を表
す。ここに、Ｒは水素原子、フッ素原子、直鎖若しくは
分枝のＣ1〜Ｃ12のアルキル基、直鎖若しくは分枝のＣ2
〜Ｃ12のアルケニル基または直鎖若しくは分枝のＣ2〜
Ｃ12のアルキニル基を表し、ｑは０または１である。ま
た、ＡおよびＢが同時に置換基のない１、４−フェニレ
ン、ｎ≦２のフッ素置換された１、４−フェニレンある
いは置換基のない１、５−ナフタレンの場合は、Ｒ1お
よびＲ2は、少なくとも一方は直鎖のアルキル基、アル
ケニル基、アルコキシ基ではない］で示されるジアセチ
レン化合物、この化合物を少なくとも１種含有する液晶
組成物およびこの化合物を少なくとも１種含む液晶組成
物を一対の電極基板間に挟侍してなることを特徴とする
液晶素子を提供するものである。以下、本発明を詳細に
説明する。Wherein l and m are each independently:
Represents 0 or 1, but does not represent 0 at the same time. E and G
Each independently represents a fluorine atom, a methyl group or a methoxy group, n is an integer of 0 to 4, o and p are 0 to 3
Is an integer. R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, a trifluoromethyl group, a methoxy group optionally substituted with 1 to 3 fluorine atoms, and 1 to 5 fluorine atoms. Ethoxy, cyano, 4-R- (cycloalkyl), 4-R
Represents a-(cycloalkenyl group) or an R- (O) q group. Here, R is a hydrogen atom, a fluorine atom, a linear or branched C 1 -C 12 alkyl group, a linear or branched C 2
C 2 alkenyl group or a linear or branched -C 12 ~
Represents a C 12 alkynyl group, and q is 0 or 1. When A and B are 1,4-phenylene having no substituent at the same time, 1,4-phenylene substituted with n ≦ 2 or 1,4-naphthalene having no substituent, R 1 and R 2 are , At least one of which is not a linear alkyl group, alkenyl group or alkoxy group], a liquid crystal composition containing at least one such compound, and a liquid crystal composition containing at least one such compound. It is intended to provide a liquid crystal element characterized by being sandwiched between electrode substrates. Hereinafter, the present invention will be described in detail.
【０００９】[0009]
【発明の実施の形態】本発明のジアセチレン化合物
（１）は、例えば下記一般式（２）BEST MODE FOR CARRYING OUT THE INVENTION The diacetylene compound (1) of the present invention has, for example, the following general formula (2)
【００１０】[0010]
【化５】 Embedded image
【００１１】［式中、ｌ、ＡおよびＲ1は、前記と同じ
意味を表す。］で示される化合物および下記一般式
（３）[Wherein, 1, A and R 1 have the same meanings as described above. And a compound represented by the following general formula (3)
【００１２】[0012]
【化６】 Embedded image
【００１３】［式中、ｍ、ＢおよびＲ2は、前記と同じ
意味を表す。］で示される化合物塩化銅（Ｉ）触媒、ヒ
ドロキシアミン塩酸塩およびエチルアミン等の塩基性触
媒の存在下で反応させることにより合成することができ
る。Wherein m, B and R 2 have the same meaning as described above. The compound can be synthesized by reacting in the presence of a basic catalyst such as a copper (I) chloride catalyst, hydroxyamine hydrochloride and ethylamine.
【００１４】ここで、原料の一般式（２）および一般式
（３）で示される化合物は、例えば、特開平８−１３３
９９６号公報等に記載の製法に準じて合成できる。Here, the compounds represented by the general formulas (2) and (3) as raw materials are described, for example, in JP-A-8-133.
It can be synthesized according to the production method described in, for example, JP-A-996.
【００１５】一般式（１）の具体例を下記に示す。上式
において、Ｒ1、Ｒ2としてはそれぞれ独立に、フッ素置
換されていてもよいメチル、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、ウンデシル、ドデシル、エテニル、プロペ
ニル、ブテニル、ペンテニル、ヘキセニル、ヘプテニ
ル、オクテニル、ノネニル、デセニル、ウンデセニル、
ドデセニル、プロピニル、ブチニル、ペンチニル、ヘキ
シニル、ヘプチニル、オクチニル、ノニニル、デシニ
ル、ドデシニル、メトキシ、エトキシ、プロポキシ、ブ
トキシ、ペンチルオキシ、ヘキシルオキシ、オクチルオ
キシ、ノニルオキシ、デシルオキシ、ウンデシルオキ
シ、ドデシルオキシ、ビニルオキシ、プロペニルオキ
シ、ブテニルオキシ、ペンテニルオキシ、ヘキセニルオ
キシ、ヘプテニルオキシ、オクテニルオキシ、ノネニル
オキシ、デセニルオキシ、プロピオニルオキシ、ブチニ
ルオキシ、ペンチニルオキシ、ヘキシニルオキシ、ヘプ
チニルオキシ、オクチニルオキシ、ノニニルオキシ、デ
シニルオキシ、ドデシニルオキシ、Specific examples of the general formula (1) are shown below. In the above formula, R 1 and R 2 each independently may be fluorine-substituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, ethenyl, propenyl, Butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl,
Dodecenyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, noninyl, decynyl, dodecinyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, vinyloxy, Propenyloxy, butenyloxy, pentenyloxy, hexenyloxy, heptenyloxy, octenyloxy, nonenyloxy, decenyloxy, propionyloxy, butynyloxy, pentynyloxy, hexynyloxy, heptynyloxy, octynyloxy, noninyloxy, decynyloxy, dodecynyloxy,
【００１６】エテニル、プロペニル、ブテニル、ペンテ
ニル、ヘキセニル、ヘプテニル、オクテニル、ノネニ
ル、デセニル、ウンデセニル、ドデセニル、メトキシメ
チル、エトキシメチル、プロポキシメチル、ブトキシメ
チル、ペンチルオキシメチル、ヘキシルオキシメチル、
ヘプチルオキシメチル、オクチルオキシメチル、ノニル
オキシメチル、デシルオキシメチル、メトキシエチル、
エトキシエチル、プロポキシエチル、ブトキシエチル、
ペンチルオキシエチル、ヘキシルオキシエチル、ヘプチ
ルオキシエチル、オクチルオキシエチル、ノニルオキシ
エチル、デシルオキシエチル、メトキシプロピル、エト
キシプロピル、プロポキシプロピル、ブトキシプロピ
ル、ペンチルオキシプロピル、ヘキシルオキシプロピ
ル、ヘプチルオキシプロピル、オクチルオキシプロピ
ル、ノニルオキシプロピル、デシルオキシプロピル、メ
トキシブチル、エトキシブチル、プロポキシブチル、ブ
トキシブチル、ペンチルオキシブチル、ヘキシルオキシ
ブチル、ヘプチルオキシブチル、オクチルオキシブチ
ル、ノニルオキシブチル、デシルオキシブチル、メトキ
シペンチル、エトキシペンチル、プロポキシペンチル、
ブトキシペンチル、ペンチルオキシペンチル、ヘキシル
オキシペンチル、ヘプチルオキシペンチル、ヘプチルオ
キシペンチル、オクチルオキシペンチル、ノニルオキシ
ペンチル、デシルオキシペンチルEthenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentyloxymethyl, hexyloxymethyl,
Heptyloxymethyl, octyloxymethyl, nonyloxymethyl, decyloxymethyl, methoxyethyl,
Ethoxyethyl, propoxyethyl, butoxyethyl,
Pentyloxyethyl, hexyloxyethyl, heptyloxyethyl, octyloxyethyl, nonyloxyethyl, decyloxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, pentyloxypropyl, hexyloxypropyl, heptyloxypropyl, octyloxy Propyl, nonyloxypropyl, decyloxypropyl, methoxybutyl, ethoxybutyl, propoxybutyl, butoxybutyl, pentyloxybutyl, hexyloxybutyl, heptyloxybutyl, octyloxybutyl, nonyloxybutyl, decyloxybutyl, methoxypentyl, ethoxy Pentyl, propoxy pentyl,
Butoxypentyl, pentyloxypentyl, hexyloxypentyl, heptyloxypentyl, heptyloxypentyl, octyloxypentyl, nonyloxypentyl, decyloxypentyl
【００１７】２−メチルプロピル、２−メチルブチル、
３−メチルブチル、３−メチルペンチル、２−メチルプ
ロピルオキシ、２−メチルブチルオキシ、３−メチルブ
チルオキシ、３−メチルペンチルオキシ、2-methylpropyl, 2-methylbutyl,
3-methylbutyl, 3-methylpentyl, 2-methylpropyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 3-methylpentyloxy,
【００１８】４―メチルシクロヘキシル、４―エチルシ
クロヘキシル、４―プロピルシクロヘキシル、４―ブチ
ルシクロヘキシル、４―ペンチルシクロヘキシル、４―
ヘキシルシクロヘキシル、４―ヘキシルシクロヘキシ
ル、４―オクチルシクロヘキシル、４―ノニルシクロヘ
キシル、４―デシルシクロヘキシル、４―プロピルシク
ロヘキセニル、４―ペンチルシクロヘキセニル、水素原
子、フッ素原子、トリフロロメチル基、トリフロロメト
キシ基、シアノ基等が挙げられる。4-methylcyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, 4-butylcyclohexyl, 4-pentylcyclohexyl, 4-
Hexylcyclohexyl, 4-hexylcyclohexyl, 4-octylcyclohexyl, 4-nonylcyclohexyl, 4-decylcyclohexyl, 4-propylcyclohexenyl, 4-pentylcyclohexenyl, hydrogen atom, fluorine atom, trifluoromethyl group, trifluoromethoxy group And a cyano group.
【００１９】また、一般式（１）におけるＡ、Ｂとして
は、それぞれ独立に１，４―フェニレン、１，４―（２
―フルオロ）フェニレン、１，４―（３―フルオロ）フ
ェニレン、１，４―（２，５―ジフルオロ）フェニレ
ン、１，４―（３，６―ジフルオロ）フェニレン、１，
４―（２，６―ジフルオロ）フェニレン、１，４―
（３、５―ジフルオロ）フェニレン、２，５―ピリミジ
ンジイル、５，２―ピリミジンジイル、２，５−ピリジ
ンジイル、５，２−ピリジンジイル、１，５−ナフタレ
ン、１，５−（２−フルオロ）ナフタレン、１，５−
（３−フルオロ）ナフタレン、１，５−（４−フルオ
ロ）ナフタレン、１，５−（２、３−ジフルオロ）ナフ
タレン、等が挙げられる。A and B in the general formula (1) are each independently 1,4-phenylene and 1,4- (2
-Fluoro) phenylene, 1,4- (3-fluoro) phenylene, 1,4- (2,5-difluoro) phenylene, 1,4- (3,6-difluoro) phenylene, 1,
4- (2,6-difluoro) phenylene, 1,4-
(3,5-difluoro) phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl, 5,2-pyridinediyl, 1,5-naphthalene, 1,5- (2- Fluoro) naphthalene, 1,5-
(3-Fluoro) naphthalene, 1,5- (4-fluoro) naphthalene, 1,5- (2,3-difluoro) naphthalene, and the like.
【００２０】さらに、具体的な化合物例を以下に記す
が、本発明はこれらの化合物に限定されるものではな
い。Furthermore, specific examples of the compounds are described below, but the present invention is not limited to these compounds.
【００２１】[0021]
【化７】 Embedded image
【００２２】[0022]
【化８】 Embedded image
【００２３】[0023]
【化９】 Embedded image
【００２４】[0024]
【化１０】 Embedded image
【００２５】[0025]
【化１１】 Embedded image
【００２６】[0026]
【化１２】 Embedded image
【００２７】[0027]
【化１３】 Embedded image
【００２８】[0028]
【化１４】 Embedded image
【００２９】[0029]
【化１５】 Embedded image
【００３０】[0030]
【化１６】 Embedded image
【００３１】[0031]
【化１７】 Embedded image
【００３２】[0032]
【化１８】 Embedded image
【００３３】本発明の液晶組成物とは、一般式（１）で
示されるジアセチレン化合物を少なくとも１種を配合成
分として含有する液晶組成物である。混合する他の成分
は特に限定されるものではないが、液晶相を示す化合物
あるいは組成物であることが好ましい。また、ジアセチ
レン化合物（１）は、得られる液晶組成物の０．１〜９
９．９重量％、好ましくは１〜９９重量％含有される。The liquid crystal composition of the present invention is a liquid crystal composition containing at least one diacetylene compound represented by the general formula (1) as a compounding component. The other components to be mixed are not particularly limited, but are preferably a compound or a composition exhibiting a liquid crystal phase. The diacetylene compound (1) is used in an amount of 0.1 to 9 in the obtained liquid crystal composition.
9.9% by weight, preferably 1-99% by weight.
【００３４】また、本発明の上記の組成物には、捩れ剤
として、カイラル化合物が一種もしくは複数種含まれて
いても良い。本発明の液晶組成物に用いられるカイラル
化合物は、特に限定されないが、好ましくは以下に示す
化合物を例示することができる。The composition of the present invention may contain one or more chiral compounds as a twisting agent. The chiral compound used in the liquid crystal composition of the present invention is not particularly limited, but preferably includes the following compounds.
【００３５】[0035]
【化１９】 Embedded image
【００３６】[0036]
【実施例】以下実施例により、本発明に関してより詳細
に述べるが、本発明はこれらに限定されるものではな
い。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【００３７】実施例１ 撹拌装置、温度計を装着したフラスコ内に、４−シアノ
フェニルアセチレンを３．５６ｇ、メタノール１３２．
０ｇ、塩化銅（Ｉ）０．８ｇ、ＮＨ2ＯＨ・ＨＣｌを
２．５ｇ、水８．０ｇ、７０％のエチルアミン１０５．
０ｇを加えた。その後、トルエンに溶かした１−ブロモ
１−ペンチン４４．０ｇを室温で滴下し、２０時間室
温で撹拌した。その後、濾過し水で洗浄した。濾液を濃
縮後、酢酸エチルで抽出し、２８％アンモニア水、水で
順次洗浄し、シリカゲルクロマトグラフィにてアニチリ
ドを除去した後、濃縮し濃縮物をシリカゲルクロマトグ
ラフィーにて分離し、メタノールで再結晶を繰り返して
目的とする下記化合物（１−１）を１．６６ｇ得た。Example 1 A flask equipped with a stirrer and a thermometer was charged with 3.56 g of 4-cyanophenylacetylene and methanol.
0 g, copper (I) chloride 0.8 g, NH 2 OH · HCl 2.5 g, water 8.0 g, 70% ethylamine 105.
0 g was added. Thereafter, 44.0 g of 1-bromo 1-pentyne dissolved in toluene was added dropwise at room temperature, and the mixture was stirred at room temperature for 20 hours. Thereafter, the mixture was filtered and washed with water. The filtrate was concentrated, extracted with ethyl acetate, washed sequentially with 28% aqueous ammonia and water, and after removing anitilide by silica gel chromatography, concentrated. The concentrate was separated by silica gel chromatography, and recrystallized from methanol. By repeating this, 1.66 g of the following compound (1-1) was obtained.
【００３８】[0038]
【化２０】 Embedded image
【００３９】上記化合物（１―１）を、メルク社製液晶
組成物Ｅ７（Δｎ＝０．２１）に１５重量％混合して液
晶組成物を調製した。この液晶組成物のΔｎをアッベの
屈折計を用いて測定（測定条件；５８９ｎｍで、２０℃
で）し、外挿して化合物（１−１）のΔｎを求めた。Δ
ｎ値は以下の式により求めた。The above compound (1-1) was mixed with 15% by weight of a liquid crystal composition E7 (Δn = 0.21) manufactured by Merck to prepare a liquid crystal composition. The Δn of the liquid crystal composition was measured using an Abbe refractometer (measurement conditions: 589 nm, 20 ° C.).
) And extrapolated to determine Δn of compound (1-1). Δ
The n value was determined by the following equation.
【数１】Δｎ＝（ｂ−０．８５×ａ）／０．１５Δn = (b−0.85 × a) /0.15
【００４０】上式で、ａはＥ７のΔｎ、ｂはＥ７と化合
物（１−１）を混合した組成物のΔｎである。上式によ
り求めた化合物（１−１）のΔｎは０．３１であった。In the above formula, a is Δn of E7, and b is Δn of a composition obtained by mixing E7 and compound (1-1). The Δn of the compound (1-1) determined by the above formula was 0.31.
【００４１】[0041]
【発明の効果】本発明の化合物あるいは本発明の化合物
を用いた液晶組成物は屈折率異方性が大きく、たとえば
ＳＴＮ（超ねじれネマティック）型液晶素子やＰＤＬＣ
（ポリマ―分散型液晶）、ＰＮＬＣ（ポリマーネットワ
ーク液晶）、ＰＳＣＴ（ポリマー安定化コレステリック
テクスチャ液晶）型液晶素子や、反射型ゲストホスト型
液晶素子に代表される液晶素子を構成する材料として特
に有用である。The compound of the present invention or a liquid crystal composition using the compound of the present invention has a large refractive index anisotropy, for example, an STN (super twisted nematic) type liquid crystal element or PDLC.
(Polymer-dispersed liquid crystal), PNLC (Polymer Network Liquid Crystal), PSCT (Polymer Stabilized Cholesteric Textured Liquid Crystal), and reflective guest-host type liquid crystal devices. is there.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｃ 43/205 Ｃ０７Ｃ 43/205 Ｃ 43/225 43/225 Ｃ 255/50 255/50 255/52 255/52 255/54 255/54 Ｃ０９Ｋ 19/18 Ｃ０９Ｋ 19/18 Ｇ０２Ｆ 1/13 ５００ Ｇ０２Ｆ 1/13 ５００ (72)発明者 南井 正好 大阪府高槻市塚原２丁目10番１号 住友化 学工業株式会社内──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code FI C07C 43/205 C07C 43/205 C 43/225 43/225 C 255/50 255/50 255/52 255/52 255/54 255 / 54 C09K 19/18 C09K 19/18 G02F 1/13 500 G02F 1/13 500 (72) Inventor Masayoshi Minami 2-10-1, Tsukahara, Takatsuki-shi, Osaka Sumitomo Chemical Co., Ltd.
Claims (3)
表し、同時に０を表さない。ＥおよびＧは、それぞれ独
立に、フッ素原子、メチル基またはメトキシ基を表し、
ｎは０〜４の整数、ｏおよびｐは０〜３の整数である。
Ｒ1およびＲ2は、それぞれ独立に、水素原子、フッ素原
子、トリフルオロメチル基、１から３個のフッ素原子で
置換されていてもよいメトキシ基、１から５個のフッ素
原子で置換されていてもよいエトキシ基、シアノ基、４
−Ｒ−（シクロアルキル）基、４−Ｒ−（シクロアルケ
ニル基）またはＲ−（Ｏ）ｑ基を表す。ここに、Ｒは水
素原子、フッ素原子、直鎖若しくは分枝のＣ1〜Ｃ12の
アルキル基、直鎖若しくは分枝のＣ2〜Ｃ12のアルケニ
ル基または直鎖若しくは分枝のＣ2〜Ｃ12のアルキニル
基を表し、ｑは０または１である。また、ＡおよびＢが
同時に置換基のない１、４−フェニレン、ｎ≦２のフッ
素置換された１、４−フェニレンあるいは置換基のない
１、５−ナフタレンの場合は、Ｒ1およびＲ2は、少なく
とも一方は直鎖のアルキル基、アルケニル基、アルコキ
シ基ではない］で示されるジアセチレン化合物。(1) The following general formula (1): Wherein A and B are each independently: And l and m each independently represent 0 or 1, and do not represent 0 at the same time. E and G each independently represent a fluorine atom, a methyl group or a methoxy group;
n is an integer of 0 to 4, and o and p are integers of 0 to 3.
R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, a trifluoromethyl group, a methoxy group optionally substituted with 1 to 3 fluorine atoms, and 1 to 5 fluorine atoms. Ethoxy group, cyano group, 4
-R- (cycloalkyl) group, 4-R- (cycloalkenyl group) or R- (O) q group. Here, R represents a hydrogen atom, a fluorine atom, a linear or alkyl radical of C 1 -C 12 branched, C 2 ~ alkenyl group or a linear or branched C 2 -C 12 linear or branched Represents a C 12 alkynyl group, and q is 0 or 1. When A and B are 1,4-phenylene having no substituent at the same time, 1,4-phenylene substituted with n ≦ 2 or 1,4-naphthalene having no substituent, R 1 and R 2 are , At least one of which is not a linear alkyl, alkenyl, or alkoxy group].
化合物を少なくとも１種含有することを特徴とする液晶
組成物。2. A liquid crystal composition comprising at least one compound represented by the general formula (1) according to claim 1.
板間に挟侍してなることを特徴とする液晶素子。3. A liquid crystal device comprising the liquid crystal composition according to claim 2 sandwiched between a pair of electrode substrates.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9156598A JPH111445A (en) | 1997-06-13 | 1997-06-13 | Diacetylene compound, liquid crystal composition containing the same and liquid crystal element using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9156598A JPH111445A (en) | 1997-06-13 | 1997-06-13 | Diacetylene compound, liquid crystal composition containing the same and liquid crystal element using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH111445A true JPH111445A (en) | 1999-01-06 |
Family
ID=15631263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9156598A Pending JPH111445A (en) | 1997-06-13 | 1997-06-13 | Diacetylene compound, liquid crystal composition containing the same and liquid crystal element using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH111445A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002030016A (en) * | 2000-07-21 | 2002-01-29 | Sumitomo Chem Co Ltd | Di- or triacetylene compound having side chain, liquid crystal composition containing the same, and liquid crystal element by using the same |
| JP2002105008A (en) * | 2000-09-28 | 2002-04-10 | Dainippon Ink & Chem Inc | Method for refining liquid-crystalline compound |
| WO2010001172A1 (en) * | 2008-07-03 | 2010-01-07 | Datalase Ltd | Filters |
| US9139774B2 (en) | 2011-02-15 | 2015-09-22 | Tokyo Institute Of Technology | Diacetylene derivative and liquid crystalline polymer having diacetylene structure |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002030016A (en) * | 2000-07-21 | 2002-01-29 | Sumitomo Chem Co Ltd | Di- or triacetylene compound having side chain, liquid crystal composition containing the same, and liquid crystal element by using the same |
| JP4576678B2 (en) * | 2000-07-21 | 2010-11-10 | 住友化学株式会社 | Di- or triacetylene compound having a side chain, liquid crystal composition containing the same, and liquid crystal device using the same |
| JP2002105008A (en) * | 2000-09-28 | 2002-04-10 | Dainippon Ink & Chem Inc | Method for refining liquid-crystalline compound |
| WO2010001172A1 (en) * | 2008-07-03 | 2010-01-07 | Datalase Ltd | Filters |
| US8420282B2 (en) | 2008-07-03 | 2013-04-16 | Datalase Ltd | Filters |
| US9139774B2 (en) | 2011-02-15 | 2015-09-22 | Tokyo Institute Of Technology | Diacetylene derivative and liquid crystalline polymer having diacetylene structure |
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