JPH02196756A - Halogenophenyl allylbiphenylcarboxylates - Google Patents
Halogenophenyl allylbiphenylcarboxylatesInfo
- Publication number
- JPH02196756A JPH02196756A JP1016571A JP1657189A JPH02196756A JP H02196756 A JPH02196756 A JP H02196756A JP 1016571 A JP1016571 A JP 1016571A JP 1657189 A JP1657189 A JP 1657189A JP H02196756 A JPH02196756 A JP H02196756A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- expressed
- point
- allyl
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 7
- -1 Allyl biphenylcarboxylic acid Chemical compound 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005821 Claisen rearrangement reaction Methods 0.000 abstract description 2
- 150000001347 alkyl bromides Chemical class 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- FURZYCFZFBYJBT-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-UHFFFAOYSA-N 0.000 description 1
- OFYAEKMIQIIUAT-UHFFFAOYSA-N 4-cyclohexylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1CCCCC1 OFYAEKMIQIIUAT-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規なアリルビフェニルカルボン酸ハロゲノフ
ェニルエステル類、および該化合物を有効成分として含
有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel allylbiphenylcarboxylic acid halogenophenyl esters and liquid crystal compositions containing the compounds as active ingredients.
液晶を利用した表示素子は時計、電卓等に広く使用され
ている。これらの液晶表示素子は液晶物質の光学異方性
および誘電率の異方性（Δεと略記する）を利用したも
のである。液晶相にはネマチック液晶相、スメクチック
液晶相、コレステリンク液晶相があり、そのうちネマチ
ック液晶相を利用したものが最も広く実用化されている
。液晶表示方式には、応用される電気光学効果に対応し
て、ＴＮ（ねじれネマチック）型、ＤＳ（動的散乱）型
、ゲスト・ホスト型、ＤＡＰ型等の表示素子がある。そ
れぞれに使用される液晶物質は自然界のなるべく広い温
度範囲で液晶相を示すものが望ましい、これらの物質と
して既に多くの液晶化合物が知られているが、現在のと
ころ単一の液晶物質でそのような条件を満たす物質はな
く、数種の液晶物質またはさらに非液晶物質を混合して
実用に供している。これらの物質は水分、光、熱、空気
等に対しても安定であることを要求されている。Display elements using liquid crystals are widely used in watches, calculators, etc. These liquid crystal display elements utilize optical anisotropy and dielectric constant anisotropy (abbreviated as Δε) of liquid crystal substances. Liquid crystal phases include a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase, and among these, those utilizing the nematic liquid crystal phase are most widely put into practical use. The liquid crystal display system includes display elements of TN (twisted nematic) type, DS (dynamic scattering) type, guest-host type, DAP type, etc., depending on the applied electro-optical effect. It is desirable that the liquid crystal materials used in each of these materials exhibit a liquid crystal phase over as wide a natural temperature range as possible.Many liquid crystal compounds are already known as these materials, but at present there is no single liquid crystal material that can exhibit such a phase. There is no substance that satisfies these conditions, and several types of liquid crystal substances or even non-liquid crystal substances are mixed and put into practical use. These substances are required to be stable against moisture, light, heat, air, and the like.
前記のような液晶物質等の混合物である液晶組成物はそ
の粘度が低く、しきい値電圧がΔεに較べ低いことが望
まれている。It is desired that the liquid crystal composition, which is a mixture of the above-mentioned liquid crystal substances, has a low viscosity and a threshold voltage lower than Δε.
本発明の目的は上述のような要求を満たす液晶化合物と
して有用な新規化合物および該化合物を含有する液晶組
成物を提供することである。An object of the present invention is to provide a novel compound useful as a liquid crystal compound that satisfies the above-mentioned requirements, and a liquid crystal composition containing the compound.
本発明の第１の発明は、下記一般式（Ｎで表わされるア
リルビフェニルカルボン酸ハロゲノフェニルエステル類
である。The first invention of the present invention is allyl biphenylcarboxylic acid halogenophenyl esters represented by the following general formula (N).
を示し、ｍは０またはｌを示し、ｎは１または２を示し
、ＸはＦまたはＣ２を示す）。, m represents 0 or l, n represents 1 or 2, and X represents F or C2).
本発明の第２の発明は、該化合物を有効成分として含有
する液晶組成物である。A second invention of the present invention is a liquid crystal composition containing the compound as an active ingredient.
本発明の化合物の製造方法としては、例えば下記反応式
によって示される反応によって製造し得る。The compound of the present invention can be produced, for example, by a reaction represented by the following reaction formula.
（ただし、上式中、Ｒは炭素数１−１５の二重結合を有
する直鎖ないしは技分かれしたアルキル基（ｍ、ｎ、Ｘ
は前記と同じ）
すなわち、４−アリルオキシビフェニル−４１−カルボ
ン酸エチルエステルをジエチルアニリン中で加熱するこ
とにより、クライゼン転位反応をして３−アリル−４−
ヒドロキシビフェニル−４１−カルボン酸エチルエステ
ルとする０次いで、アセトン溶媒中無水炭酸カリウムの
存在下で臭化アルキルと反応させ、３−アリル−４−ア
ルコキシビフェニル−４１−カルボン酸エチルエステル
を製造する。これを水酸化カリウムで加水分解してビフ
ェニルカルボン酸誘導体を製造する０次いでこれを塩化
チオニルと反応させて酸クロリドとし、さらに４−ハロ
ゲノフェノール誘導体とピリジンの存在下に反応させ、
目的の３−アリル−４−アルコキシビフェニル−４１−
カルボン酸ハロゲノフェニルエステル類を製造し得る。(However, in the above formula, R is a straight chain or branched alkyl group having a double bond of 1 to 15 carbon atoms (m, n,
is the same as above) That is, by heating 4-allyloxybiphenyl-41-carboxylic acid ethyl ester in diethylaniline, a Claisen rearrangement reaction is performed to form 3-allyl-4-
Hydroxybiphenyl-41-carboxylic acid ethyl ester is then reacted with an alkyl bromide in the presence of anhydrous potassium carbonate in an acetone solvent to produce 3-allyl-4-alkoxybiphenyl-41-carboxylic acid ethyl ester. This is hydrolyzed with potassium hydroxide to produce a biphenylcarboxylic acid derivative. This is then reacted with thionyl chloride to form an acid chloride, and further reacted with a 4-halogenophenol derivative in the presence of pyridine.
Target 3-allyl-4-alkoxybiphenyl-41-
Carboxylic acid halogenophenyl esters can be produced.
また、本発明の液晶組成物は、前記の式に示す本発明の
化合物を少なくとも一成分含有することを特徴とする。Further, the liquid crystal composition of the present invention is characterized in that it contains at least one component of the compound of the present invention represented by the above formula.
本発明の液晶組成物の成分にできる本発明の化合物以外
の他の成分としては、例えばエステル系、シッフ塩基系
、ビフェニル系、フェニルシクロヘキサン系、複素環系
等の化合物を挙げることができる。Other components other than the compound of the present invention that can be used as components of the liquid crystal composition of the present invention include, for example, ester-based, Schiff base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based compounds.
本発明の化合物は、広い温度範囲でネマチック液晶相を
示し、かつ液晶から液体になる温度（Ｎ−１点）が高い
、また、液晶組成物に少量添加することにより、液晶組
成物の液晶−液体点（Ｎ−１点）を上昇させることがで
きる。また、粘度もそれほど高めることはない。The compound of the present invention exhibits a nematic liquid crystal phase over a wide temperature range, and has a high temperature (N-1 point) at which the liquid crystal changes from liquid crystal to liquid. The liquid point (N-1 point) can be raised. Moreover, the viscosity does not increase so much.
本発明の化合物は、アリルビフェニルカルボン酸ハロゲ
ノフェニルエステル類と称しているが、一般式（Ｉ）お
よび実施例１で明らかなようにハロゲノビフェニリルエ
ステルも含んでいる。Although the compounds of the present invention are referred to as allylbiphenylcarboxylic acid halogenophenyl esters, as is clear from general formula (I) and Example 1, they also contain halogenobiphenyl esters.
本発明の化合物は、多くの液晶化合物、すなわちエステ
ル系、シッフ塩基系、ビフェニル系、フェニルシクロヘ
キサン系、複素環系等との相溶性がよく、本発明の化合
物を液晶化合物に少量添加することによって低粘性にし
、Δε（＝ε１１−ε上、すなわち液晶軸方向に平行な
誘電率ε１１と直角な誘電率ε土との差）に較べ、しき
い値電圧（以下、■−いと略記する）が低く、Δｎ（Ｅ
−ｎｌｌ−ｎ上、すなわち液晶軸方向に平行な屈折率と
直角な屈折率との差）を小さくすることができる。The compound of the present invention has good compatibility with many liquid crystal compounds, such as ester type, Schiff base type, biphenyl type, phenylcyclohexane type, heterocyclic type, etc., and by adding a small amount of the compound of the present invention to the liquid crystal compound. The viscosity is low, and the threshold voltage (hereinafter abbreviated as ■-) is lower than Δε (=ε11−ε, that is, the difference between the dielectric constant ε11 parallel to the liquid crystal axis direction and the dielectric constant ε perpendicular to the liquid crystal axis direction). low, Δn(E
-nll-n, that is, the difference between the refractive index parallel to the liquid crystal axis direction and the refractive index perpendicular to the liquid crystal axis direction).
また、不飽和二重結合を有することにより、５ＴＮ（ス
ーパートウイステッドネマチック）型標示方式に対して
、有利に利用することができる。Moreover, since it has an unsaturated double bond, it can be advantageously used in a 5TN (super twisted nematic) type display system.
〔実施例］
以下、実施例によって本発明をさらに具体的に説明する
が、本発明はこの実施例によって何ら限定されるもので
はない。[Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例１
３−アリル−４−ペンチルオキシビフェニリル＝４１−
カルボン酸−４−フルオロ−４１−ビフェニリルエステ
ルの製造
（（Ｉ）式において、Ｒ＝Ｃ，Ｈ，、−１ｍ＝Ｏ１ｎ＝
２、Ｘ＝Ｆ）
３−アリル−４−アリルオキシビフェニル−４力ルボン
酸エチルエステル１７ｇをＮ、 Ｎ−ジエチルアニリン
１００ｍｊｉ！に溶かし、８時間窒素雰囲気下還流した
。放冷後、反応液を６Ｎ塩酸５００ｍｆに入れた。析出
した結晶を濾過し、水でよく洗い、乾燥した。この結晶
をアセトン１１、無水炭酸ナトリウムとともによく撹拌
しながら、臭化ペンチル２０ｇを加え、さらに２４時間
還流した。沈殿物を濾別し、アセトンを留去した。残っ
た油状物をトルエン３００ｍ１に溶かし、２Ｎ水酸化ナ
トリウムで洗浄後、水で中性になるまで洗った。トルエ
ン層を無水硫酸ナトリウムで乾燥後、トルエンを減圧に
て留去し、残った油状物を水酸化カリウム３０ｇを水２
００ｍｆｆ１に溶かし、エタノール５００ｍｆｆ１を加
えたものと反応を行なった。５時間還流後冷却し、６Ｎ
塩酸７００ｍ１に加えて得られた沈澱物を濾過復水でよ
く洗い、乾燥し、３−アリル−４−ペンチルオキシビフ
ェニル−４”−カルボン酸ヲ得ｆ、：、。Example 1 3-allyl-4-pentyloxybiphenylyl = 41-
Production of carboxylic acid-4-fluoro-41-biphenylyl ester (in formula (I), R=C,H,, -1m=O1n=
2, The mixture was dissolved in water and refluxed under nitrogen atmosphere for 8 hours. After cooling, the reaction solution was poured into 500 mf of 6N hydrochloric acid. The precipitated crystals were filtered, thoroughly washed with water, and dried. While thoroughly stirring the crystals with 11 acetone and anhydrous sodium carbonate, 20 g of pentyl bromide was added, and the mixture was further refluxed for 24 hours. The precipitate was filtered off, and the acetone was distilled off. The remaining oil was dissolved in 300 ml of toluene, washed with 2N sodium hydroxide, and then with water until neutral. After drying the toluene layer over anhydrous sodium sulfate, the toluene was distilled off under reduced pressure, and the remaining oil was mixed with 30 g of potassium hydroxide and 2
The mixture was dissolved in 00 mff1 and reacted with 500 mff1 of ethanol. After refluxing for 5 hours, cool and add 6N
The precipitate obtained by adding to 700 ml of hydrochloric acid was thoroughly washed with filtered condensate water and dried to obtain 3-allyl-4-pentyloxybiphenyl-4''-carboxylic acid.
このようにして製造した３−アリル−４−ペンチルオキ
シビフェニル−４１−カルボン酸６．４ｇと大過剰の塩
化チオニルをマントルヒータ上で４時間還流下に加熱し
た。次いで水流ポンプで減圧にして、過剰の塩化チオニ
ルを留去し、残った結晶物として酸クロリドを得た。6.4 g of 3-allyl-4-pentyloxybiphenyl-41-carboxylic acid thus produced and a large excess of thionyl chloride were heated under reflux on a mantle heater for 4 hours. Then, the pressure was reduced using a water jet pump to distill off excess thionyl chloride to obtain acid chloride as the remaining crystalline product.
別のフラスコに４−フルオロ−４Ｉ−ヒドロキシビフェ
ニル４ｇをピリジン２０ｍ１に溶解した溶液を準備し、
これにさきに製造した酸クロリドを加え、さらにトルエ
ン１００ｍｆを加え、よく撹拌した。In another flask, prepare a solution of 4 g of 4-fluoro-4I-hydroxybiphenyl dissolved in 20 ml of pyridine,
The acid chloride prepared earlier was added to this, and 100 mf of toluene was added, followed by thorough stirring.
一晩放置してから、水５００ｍｊ！中にあけ、トルエン
５０ｍｆを加えて抽出した。トルエン層を６Ｎ塩酸で、
次いで２Ｎ苛性ソーダ水溶液で洗浄した後、中性になる
まで水洗した。After leaving it overnight, add 500mj of water! It was poured into the container, and 50 mf of toluene was added for extraction. The toluene layer was treated with 6N hydrochloric acid,
Next, it was washed with a 2N aqueous sodium hydroxide solution, and then washed with water until it became neutral.
次いで、無水硫酸ナトリウムで乾燥後、トルエンを減圧
で留去し、残った油状物を活性アルミナのカラムを用い
て、トルエン溶媒でクロマト処理を行なった。溶出した
トルエン溶液を減圧にて、トルエンを留去し、残った油
状物をエタノールで再結晶を行なって、目的とする３−
アリル−４−ペンチルオキシビフェニリル−４１−カル
ボン酸−４−フルオロ−４１−ビフェニリルエステルを
得た。収量は１．５ｇ（収率３０％）、結晶−スメクチ
ック液晶転移点（Ｃ−３）は１２３．９°Ｃ、スメクチ
ック−ネマチック液晶転移点（Ｓ−Ｎ）は１５２．９°
Ｃ、ネマチック液晶−透明点（Ｎ−１）は２２０．０℃
であった。Next, after drying over anhydrous sodium sulfate, toluene was distilled off under reduced pressure, and the remaining oil was chromatographed using a toluene solvent using an activated alumina column. The toluene was distilled off from the eluted toluene solution under reduced pressure, and the remaining oil was recrystallized with ethanol to obtain the desired 3-
Allyl-4-pentyloxybiphenylyl-41-carboxylic acid-4-fluoro-41-biphenylyl ester was obtained. Yield: 1.5g (yield 30%), crystalline-smectic liquid crystal transition point (C-3): 123.9°C, smectic-nematic liquid crystal transition point (S-N): 152.9°
C, Nematic liquid crystal - Clearing point (N-1) is 220.0℃
Met.
実施例２〜３
実施例１において、３−アリル−４−ペンチルオキシビ
フェニル−４１−カルボン酸の代わりに種々の３−アリ
ル−４−アルコキシ、またはアルキル、ビフェニル−４
９−カルボン酸を、また４−フルオロ−４°−ヒドロキ
シビフェニルの代わりに各種のハロゲノフェノールを用
いて、目的のエステル誘導体を製造した結果を第１表に
実施例１の結果とともに示した。Examples 2 to 3 In Example 1, various 3-allyl-4-alkoxy, or alkyl, biphenyl-4
Table 1 shows the results of producing the desired ester derivatives using 9-carboxylic acid and various halogenophenols instead of 4-fluoro-4°-hydroxybiphenyl, together with the results of Example 1.
第
表
実施例４
（Ａ）
トランス−４−プロとルー（４−シアノフェニル）シク
ロヘキサン ３０重量％トランス−４−ペン
チル−（４−シアノフェニル）シクロヘキサン
４０ｆｔＩ％トランスー４−へブチル−（４−シア
ノフェニル）シクロヘキサン ３０重景％な
る組成の液晶組成物（Ａ）のＮ−１点は５２．１℃、Δ
εは＋１０．７．２０℃における粘度は２１゜７ｃＰで
あり、光学異方性値（Δｎ）は０．１１９である。Table Example 4 (A) trans-4-pro-(4-cyanophenyl)cyclohexane 30% by weight trans-4-pentyl-(4-cyanophenyl)cyclohexane
The N-1 point of liquid crystal composition (A) with a composition of 40ftI% trans-4-hebutyl-(4-cyanophenyl)cyclohexane and 30ftI% is 52.1°C and Δ
ε is +10.7. The viscosity at 20° C. is 21°7 cP, and the optical anisotropy value (Δn) is 0.119.
液晶セルとして酸化ケイ素をコーティングし、ラビング
処理した酸化スズ透明電極を有する基板を対向させて組
立てた、電極間距離が１０ａｍのものを用意し、上記の
液晶混合物（Ａ）を封入して２０°Ｃで、その特性を測
定したところ、■いは１．６５であった。A liquid crystal cell was prepared by assembling substrates coated with silicon oxide and having rubbed tin oxide transparent electrodes with a distance between the electrodes of 10 am, and the above liquid crystal mixture (A) was sealed in the cell at 20°. When the characteristics of C were measured, the value of ■ was 1.65.
この液晶組成物（Ａ）９０重量％に本発明の実施例１で
製造した３−アリル−４−ペンチルオキシビフェニリル
−４１−カルボン酸−４−フルオロ−４１−ビフェニリ
ルエステル１０重量％を溶解した組成物のＮ−１点は６
５．４°Ｃ１Δεは＋１１．０．２０℃における粘度は
２２．１ｃＰであり、Δｎは０．１１０であった。10% by weight of 3-allyl-4-pentyloxybiphenylyl-41-carboxylic acid-4-fluoro-41-biphenylyl ester produced in Example 1 of the present invention was dissolved in 90% by weight of this liquid crystal composition (A). The N-1 point of the composition is 6
5.4°C1Δε was +11.0. The viscosity at 20°C was 22.1 cP, and Δn was 0.110.
そして、該組成物を用いて前述と同じ液晶セルに封入し
たものの特性については、■いカ月、６０Ｖであり、粘
度をそれほど上昇させずに、Ｎ−１点を大幅に高くする
ことができた。The properties of the composition sealed in the same liquid crystal cell as described above were 60V for two months, and the N-1 point could be significantly increased without increasing the viscosity much. .
本発明の化合物は、広い温度範囲でネマチック液晶相を
示し、かつ高いＮ−Ｉ点を示し、液晶組成物に少量添加
することにより、粘度をそれほど高めることなく、液晶
組成物のＮｉ点を上昇させることができる。また本発明
の化合物は、多くの液晶化合物、すなわちエステル系、
シッフ塩基系、ピフェニル系、フェニルシクロヘキサン
系、複素環系等との相溶性が良好であり、本発明の化合
物を液晶組成物に少量含有させることにより低粘性にし
、Δεに較べてＶｔｈが低く、△ｎを小さくすることが
できる。The compound of the present invention exhibits a nematic liquid crystal phase in a wide temperature range and a high N-I point, and by adding a small amount to a liquid crystal composition, the Ni point of the liquid crystal composition can be increased without significantly increasing the viscosity. can be done. In addition, the compound of the present invention can be used for many liquid crystal compounds, such as esters,
It has good compatibility with Schiff base systems, piphenyl systems, phenylcyclohexane systems, heterocyclic systems, etc., and by containing a small amount of the compound of the present invention in a liquid crystal composition, it has low viscosity, and Vth is low compared to Δε. Δn can be made small.
本発明の化合物は、不飽和二重結合を有しているので、
ＳＴＮ （スーパートウイステッドネマチック）型標示
素子に有利に応用できる。Since the compound of the present invention has an unsaturated double bond,
It can be advantageously applied to STN (super twisted nematic) type indicating elements.
Claims (1)
カルボン酸ハロゲノフェニルエステル類。 ▲数式、化学式、表等があります▼・・・（ I ） （ただし、上式中、Ｒは炭素数１〜１５の二重結合を有
する直鎖ないしは枝分かれしたアルキル基を示し、ｍは
０または１を示し、ｎは１または２を示し、ＸはＦまた
はＣｌを示す）。 ２、請求項１、記載のアリルビフェニルカルボン酸ハロ
ゲノフェニルエステル類を有効成分として含有する液晶
組成物。[Claims] 1. Allyl biphenylcarboxylic acid halogenophenyl esters represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (However, in the above formula, R represents a straight chain or branched alkyl group having a double bond of 1 to 15 carbon atoms, and m is 0 or 1, n represents 1 or 2, and X represents F or Cl). 2. A liquid crystal composition containing the allylbiphenylcarboxylic acid halogenophenyl ester according to claim 1 as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1016571A JPH02196756A (en) | 1989-01-26 | 1989-01-26 | Halogenophenyl allylbiphenylcarboxylates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1016571A JPH02196756A (en) | 1989-01-26 | 1989-01-26 | Halogenophenyl allylbiphenylcarboxylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02196756A true JPH02196756A (en) | 1990-08-03 |
Family
ID=11919979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1016571A Pending JPH02196756A (en) | 1989-01-26 | 1989-01-26 | Halogenophenyl allylbiphenylcarboxylates |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02196756A (en) |
-
1989
- 1989-01-26 JP JP1016571A patent/JPH02196756A/en active Pending
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