JPH0211576A - Ester derivative of optically active benzoic acid and allylpyrimidinylphenol - Google Patents
Ester derivative of optically active benzoic acid and allylpyrimidinylphenolInfo
- Publication number
- JPH0211576A JPH0211576A JP16065988A JP16065988A JPH0211576A JP H0211576 A JPH0211576 A JP H0211576A JP 16065988 A JP16065988 A JP 16065988A JP 16065988 A JP16065988 A JP 16065988A JP H0211576 A JPH0211576 A JP H0211576A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- optically active
- formula
- benzoic acid
- allylpyrimidinylphenol
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims description 13
- 150000002148 esters Chemical class 0.000 title claims description 7
- 239000005711 Benzoic acid Substances 0.000 title claims description 6
- 235000010233 benzoic acid Nutrition 0.000 title claims description 6
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004185 ester group Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- -1 phenyl ester Chemical class 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- CGDCHTLRDXXNPE-UHFFFAOYSA-N 2-pyrimidin-2-ylphenol Chemical compound OC1=CC=CC=C1C1=NC=CC=N1 CGDCHTLRDXXNPE-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は光学活性安息香酸とアリルピリミジニルフェノ
ールとのエステル誘導体および、それを含有する液晶組
成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an ester derivative of optically active benzoic acid and allylpyrimidinylphenol, and a liquid crystal composition containing the same.
液晶表示素子は液晶物質の特性である光学異方性および
誘電異カ性を利用したものである。この表示素子には各
種の方式のものがあるが、その代表的なものにＴＮ型（
ねじれネマチック型）の表示セルがある。Liquid crystal display elements utilize optical anisotropy and dielectric anisotropy, which are characteristics of liquid crystal materials. There are various types of display elements, but the representative one is the TN type (
There is a twisted nematic display cell.
この方式のものに用いられる液晶物質としては正の誘電
異カ性を有する液晶組成物が用いられるが、この液晶組
成物としては池の場合と同様に、光、熱、水分、空気等
に対し安定で、かつ室温を含むできるだけ広い温度範囲
で液晶相を示すことが必要である。The liquid crystal material used in this system is a liquid crystal composition with positive dielectric anisotropy, but as in the case of a pond, this liquid crystal composition is sensitive to light, heat, moisture, air, etc. It is necessary to be stable and exhibit a liquid crystal phase over as wide a temperature range as possible, including room temperature.
また近年表示素子の多桁駆動表示が望まれ、従来のＴＮ
型方式では表示品位が劣るため、新たに一連のスーパー
ツイスト型表示素子（ＳＴＮと略す）が、Ｍ、シャフト
（Ｓｃｈａｄｔ） 、Ｆ 、リーンフーツ（Ｌｅｅｎｈ
ｏｕｔｓ ）により提案され（Ａｐｐｌ、 Ｐｈｙｓ。In addition, in recent years, multi-digit drive display of display elements has been desired, and conventional TN
Since the display quality of the mold type method is inferior, a new series of super twist type display elements (abbreviated as STN) has been developed by M, Schadt, F, and Leenh.
proposed by (Appl, Phys.
Ｌｅｔｔ、 ５０．２３６ （１９８７））多桁駆動表
示の中でも品位が優れたものである。Lett, 50.236 (1987)) It has excellent quality among multi-digit drive displays.
ＴＮ型表示素子では、液晶の品質が次の点で問題になる
場合が多い、即ち表示面にいわゆるリバースドメイン（
しま模様）が発生する場合があり、この様な現象を防ぐ
ためには、光学活性物質を添加すればよいことが知られ
ている。In TN type display elements, the quality of the liquid crystal often becomes a problem due to the following points. Namely, the so-called reverse domain (
It is known that in order to prevent this phenomenon, it is sufficient to add an optically active substance.
またＳＴＮ表示方式に望まれる液晶の性質としては、液
晶の広がり、ねじれ、曲がりの弾性率をそれぞれに、に
、に３とし、液晶の軸方向に平行な誘電率をε１１．直
角な方向をε□とするとき、Ｋ ／に１が多きく、Ｋ
２／に１が小さく、Δε（＝ε１１−ε工）／ε工が小
さい値が望まれている。In addition, the properties of the liquid crystal desired for the STN display system are that the elastic modulus of the liquid crystal for spreading, twisting, and bending is set to 3 and 3, respectively, and the dielectric constant parallel to the axial direction of the liquid crystal is set to ε11. When the perpendicular direction is ε□, there are many 1 in K /, and K
It is desired that 1 is small in 2/ and that Δε (=ε11−ε work)/ε work is a small value.
（Ｈ，５ｃｈａｄｔ、 Ｆ、Ｌｃｅｎｈｏｕｔｓ；
５ｏｃｉｅｔｙ ｆｏｒ Ｉｎｆｏｒ−ｎａｔｉｏｎ
Ｄｉｓｐｌａｙ Ｉｎｔｅｒｎａｔｉｏｎａｌ
５ｙｎｐｏｓｉｕｌ。(H, 5chadt, F, Lcenhouts;
5ociety for Infor-nation
Display International
5ynposiul.
Ｄｉｇｅｓｔ ｏｆ Ｔｅｃｈｎｉｃａｌ Ｐａ
ｐｅｒｓ Ｖｏｌ、 ＸＶＩＩＩ ； ＮｅｗＯ
ｒｌｅａｎｓ、 Ｌｏｕｉｓｉａｎａ、 Ｈａｙ
１２− １４． （１９８７） ３２７−本発明の
目的は、液晶に求められる基本特性である、光、熱、水
分、空気等に対し安定で、室温を含むできるだけ広い温
度範囲で液晶相を示す液晶成分であって、前記ＴＮ表示
素子のリバースドメインの発生を防ぐのに好適な光学活
性物質であり、なおＳＴＮ表示方式においてら、Ｋ３／
に１を大きく、Ｋ ２ ／ Ｋ １ を小さく、Δε／
ε工を小さくするのに有効な光学活性を有する新規な化
合物および、これを添加した液晶組成物を提供すること
である。Digest of Technical Pa
pers Vol, XVIII; NewO
rleans, Louisiana, Hay
12-14. (1987) 327-The object of the present invention is to provide a liquid crystal component that is stable against light, heat, moisture, air, etc. and exhibits a liquid crystal phase over as wide a temperature range as possible, including room temperature, which is the basic property required of a liquid crystal. , is an optically active substance suitable for preventing the occurrence of reverse domains in the TN display element, and in the STN display system, K3/
1 is increased, K 2 / K 1 is decreased, Δε/
It is an object of the present invention to provide a novel compound having optical activity effective for reducing ε, and a liquid crystal composition containing the same.
本発明は一敗式（Ｉ）で表わされる光学活性安息香酸と
アリルピリミジニルフェノールとのエステル誘導体であ
る。The present invention is an ester derivative of optically active benzoic acid and allylpyrimidinylphenol represented by the formula (I).
（上式中、１は０または１、ｍは１または２、Ｒは水素
原子または炭素数１〜１０の直鎖よたは枝分れしたアル
キル基を示す。）
本発明はまた、前記光学活性安、９、香酸とアリルピリ
ミジニルフェノールとのエステル誘導体を少なくとも一
種含有してなる液晶組成物である。(In the above formula, 1 is 0 or 1, m is 1 or 2, and R is a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms.) This is a liquid crystal composition containing at least one type of ester derivative of activated ammonium 9, aromatic acid and allylpyrimidinylphenol.
本発明の化合物は、ら旋分子構造をもち、あるものはコ
レステリック液晶相、または光学活性スメクチック液晶
相を示し、また液晶とならないものもあるが、これをネ
マチック液晶組成物に少量添加して、コレステリック・
ネマチック相転移型表示素子用またはホワイト・テーラ
−型表示素子用の液晶組成物を得ることができる。The compounds of the present invention have a helical molecular structure, and some exhibit a cholesteric liquid crystal phase or an optically active smectic liquid crystal phase, while others do not form liquid crystals, but by adding a small amount of this to a nematic liquid crystal composition, Cholesteric
A liquid crystal composition for use in nematic phase change type display elements or White-Taylor type display elements can be obtained.
この化合物をネマチック液晶に１％添加して、測定して
得られるら旋ピッチの値から得られる、この化合物自体
のら旋ピッチは２０〜２５μｍ程度である。The helical pitch of this compound itself, which is obtained from the helical pitch value obtained by adding 1% of this compound to a nematic liquid crystal and measuring it, is about 20 to 25 μm.
また、この化合物はＴＮ型表示素子用のネマチック液晶
組成物に０．１〜５％位添加すると表示面のしま模様（
いわゆるリバースドメイン）の発生を少なくして、その
性能を改善することができる。In addition, when this compound is added to a nematic liquid crystal composition for a TN type display element in an amount of about 0.1 to 5%, a striped pattern on the display surface (
The performance can be improved by reducing the occurrence of so-called reverse domains.
また近年開発された大型の液晶素子であるＳＴＮ型液晶
表示素子においても、この素子に用いる液晶の成分とし
て有効である。It is also effective as a component of the liquid crystal used in STN type liquid crystal display elements, which are large liquid crystal elements developed in recent years.
本発明の光学活性安息香酸とアリルピリミジニルフェノ
ールのエステルｇ ４体の製造法としては、例えば次式
の反応によって製造することができる。As a method for producing the ester g4 of optically active benzoic acid and allylpyrimidinylphenol of the present invention, it can be produced, for example, by the reaction of the following formula.
アニリン
ピ リ ジ ン
（但しｊ 、ｍ、Ｒは前記に同じ）
すなわち、１−アリルオキシ−４−ピリミジニルベンゼ
ン誘導体をＮ、Ｎ−ジエチルアニリン中で煮沸還流して
、２−アリルピリミジニルフェノール誘導体を製造した
。Anilinepyridine (where j, m, and R are the same as above) That is, a 1-allyloxy-4-pyrimidinylbenzene derivative was boiled and refluxed in N,N-diethylaniline to produce a 2-allylpyrimidinylphenol derivative. .
この２−アリルピリミジニルフェノール誘導体に目的物
に対応する光学活性安息香酸クロリドととリジン存在下
に反応を行い、目的とする化合物を製造した。This 2-allylpyrimidinylphenol derivative was reacted with optically active benzoic acid chloride corresponding to the target compound in the presence of lysine to produce the target compound.
以下、実施例により、本発明の化合物の製造法および使
用例について更に詳細に説明するが、本発明は、この実
施例によって何等限定されるものではない。EXAMPLES Hereinafter, the production method and usage examples of the compounds of 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.
（１）＋２−アリル−４−（５−エチル−２−ピリミジ
ニル）フェノールの製造）
１−アリルオキシ−４−（５−エチル−２−ピリミジニ
ル）ベンゼン ２４ｇ （０，１モル）をＮ、Ｎ−ジエ
チルアニリン４０山１に溶かし、８時間窒素雰囲気下に
還流した。(1) Production of +2-allyl-4-(5-ethyl-2-pyrimidinyl)phenol) 24 g (0.1 mol) of 1-allyloxy-4-(5-ethyl-2-pyrimidinyl)benzene was added to N,N- The mixture was dissolved in 40 parts of diethylaniline and refluxed under nitrogen atmosphere for 8 hours.
放冷後５００ ｍｌの６Ｎ塩酸に反応液を加えた。After cooling, the reaction solution was added to 500 ml of 6N hydrochloric acid.
−晩放置後、析出した沈澱物をｊ戸別し、少量の水でよ
く洗い、減圧にて乾燥した。- After standing overnight, the precipitate was separated, thoroughly washed with a small amount of water, and dried under reduced pressure.
このものが２−アリル−４−（５−エチル−２ピリミジ
ニル）フェノールの塩酸塩である。このものをそのまま
、つぎの反応に用いた。This is 2-allyl-4-(5-ethyl-2pyrimidinyl)phenol hydrochloride. This product was used as it was in the next reaction.
（２＞（ｓ−（＋）−４−（２−メチルブチル）ビフェ
ニリル−４′ −カルボン酸 ２−アリル−４−（５−
エチル−２−ピリミジニル）フェニルエステルの製造）
＋Ｓ−（＋）−４−（２−メチルブチル）ビフェニリル
−４′ −カルボン酸クロリド２．９ｇ（０，０１モル
）を、２−アリル−４−（５−エチル−２−ピリミジニ
ル）フェノール２．４ｇ（０，０１モル）をピリミジン
２０ｍ１に溶かしたものに加え、トルエン１００ ｍｌ
を加えよく撹拌した。−晩放置後、反応物を水１００ｍ
１に性態し、トルエン層を分取して、２Ｎ水酸化ナトリ
ウムで洗い、ついで中性になるまで水でトルエン層を洗
った。(2>(s-(+)-4-(2-methylbutyl)biphenylyl-4'-carboxylic acid 2-allyl-4-(5-
2.9 g (0.01 mol) of S-(+)-4-(2-methylbutyl)biphenylyl-4'-carboxylic acid chloride was mixed with 2-allyl-4-( Add 2.4 g (0.01 mol) of 5-ethyl-2-pyrimidinyl phenol dissolved in 20 ml of pyrimidine, and add 100 ml of toluene.
was added and stirred well. -After standing overnight, add the reactant to 100ml of water.
1, the toluene layer was separated, washed with 2N sodium hydroxide, and then washed with water until neutral.
この後、無水流酸ナトリウムて゛トルエン層を乾燥後、
トルエンを減圧にして留去した。残った油状物をエタノ
ールで再結晶し、目的のＭＳ−（＋）４−（２−メチル
ブチル）ビフエニ・ゾル−４′カルボン酸 ２−アリル
−４−（５−エチル２−ピリミジニル）フェニルエステ
ルを製造した。After this, after drying the toluene layer with anhydrous sodium sulfate,
Toluene was distilled off under reduced pressure. The remaining oil was recrystallized from ethanol to obtain the desired MS-(+)4-(2-methylbutyl)bipheni sol-4'carboxylic acid 2-allyl-4-(5-ethyl 2-pyrimidinyl) phenyl ester. Manufactured.
このもののＴｃ、［ｃ（結晶からコレステリック液晶へ
の転位点）は１０１．０〜１０２．ＯｏＣｌ（９０℃で
結晶の転位が［察された。）、Ｔ （コレステリッ
ク液晶から等方性液体Ｃ−１
（透明点）＋１６４．５”Ｃ５収量は２．５＋ｒ、収率
は５０％であった。The Tc and [c (transition point from crystal to cholesteric liquid crystal) of this product are 101.0 to 102. OoCl (crystal dislocation was detected at 90°C), T (isotropic liquid C-1 (clearing point) from cholesteric liquid crystal +164.5"C5 yield was 2.5+r, yield was 50%). Ta.
同様にして、Ｓ−（±）−４−（２−メチルブチル）ビ
フェニリル−４′−カルボン酸クロリドの代りに対応す
る種々の光学活性芳香族カルボン酸クロリドを、２−ア
クリル−４−（５−エチル２−ピリミジニル）フェノー
ルの代りに対応する２−アリル−４−（５−置換−２−
ピリミジニル）フェノールを用いることにより、種々の
エステル化合物が製造できることは明らかである。Similarly, in place of S-(±)-4-(2-methylbutyl)biphenylyl-4'-carboxylic acid chloride, various corresponding optically active aromatic carboxylic acid chlorides were substituted with 2-acryl-4-(5- Corresponding 2-allyl-4-(5-substituted-2-ethyl-2-pyrimidinyl)phenol
It is clear that various ester compounds can be prepared by using (pyrimidinyl)phenol.
（応用例１）
オクタデシル−トリーエトキシシランで垂直配向処理を
したセル厚１０．５μｍのセルに、液晶組成′！ＩＪＧ
Ｒ−６３（チッソ■市販品）９０部と、本発明の前記実
施例のＳ−（＋）−４−（２−メチルブチル）ビフェニ
リル−４′ −カルボン酸２−アリル−４−（５−エチ
ル−２−ピリミジニル）フェニルエステル １０部から
なる液晶組成物を密封することにより、コレステリック
−ネマチック相転移表示素子が得られ、その作動しきい
値電圧は１２．ＯＶであった。(Application example 1) A liquid crystal composition of 10.5 μm thick cell that was vertically aligned with octadecyl-triethoxysilane! IJG
90 parts of R-63 (commercially available from Chisso Corporation) and 2-allyl-4-(5-ethyl S-(+)-4-(2-methylbutyl)biphenylyl-4'-carboxylate of the above-mentioned example of the present invention). By sealing a liquid crystal composition consisting of 10 parts of -2-pyrimidinyl) phenyl ester, a cholesteric-nematic phase change display element is obtained, the operating threshold voltage of which is 12. It was OV.
（応用例２）
市販のＴＮ用液晶組成物、フェニルシクロヘキサン系液
晶組成物（メルク社製、商品記号８１１３２）９９部に
、本発明の前記の実施例で製造したＳ−（＋）−４−＜
２−メチルブチル）ビフェニリル−４′−カルボン酸
２−アリル−４（５−エチル−２−ピリミジニル）フェ
ニルエステル １部を加えた液晶組成物を使用したＴＮ
セルは、この化合物を添加しないで製造したＴＮセルに
比較して、リバースドメインが大巾に減少していること
が肉眼により観察された。(Application Example 2) S-(+)-4- produced in the above embodiment of the present invention was added to 99 parts of a commercially available liquid crystal composition for TN, phenylcyclohexane-based liquid crystal composition (manufactured by Merck & Co., Ltd., product code 81132). <
2-Methylbutyl)biphenylyl-4'-carboxylic acid
TN using a liquid crystal composition containing 1 part of 2-allyl-4(5-ethyl-2-pyrimidinyl) phenyl ester
It was visually observed that the reverse domain of the cells was significantly reduced compared to TN cells produced without the addition of this compound.
本発明のエステル誘導体は池の液晶化合物と配合して、
光、熱、水分、空気等に対し安定で、室温を含む広い温
度範囲で液晶相を示し、ＴＮ表示素子に配合して、リバ
ースドメインの発生を防ぐのに好適な光学活性物質であ
り、ＳＴＮ表示方式においても、Ｋ３／に１を大きく、
Ｋ２／に１を小さく、Δε／ε□を小さくするのに有効
な液晶成分である。The ester derivative of the present invention is blended with Ike's liquid crystal compound,
It is an optically active substance that is stable against light, heat, moisture, air, etc., exhibits a liquid crystal phase over a wide temperature range including room temperature, and is suitable for blending into TN display elements to prevent the occurrence of reverse domains. Also in the display method, increase 1 to K3/,
It is a liquid crystal component that is effective in reducing K2/1 and Δε/ε□.
手続補正書（自制 昭和６３年７月２２日Procedural amendment (self-restraint) July 22, 1986
Claims (1)
原子または炭素数１〜１０の 直鎖または枝分れしたアルキル基を示 す。） で表わされる光学活性安息香酸とアリルピリミジニルフ
ェノールとのエステル誘導体。 ２、請求項１記載の光学活性安息香酸とアリルピリミジ
ニルフェノールとのエステル誘導体を少なくとも一種含
有してなる液晶組成物。[Claims] 1. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are included ▼ ... (I) (In the above formula, l is 0 or 1, m is 1 or 2, and R is a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms.) An ester derivative of optically active benzoic acid and allylpyrimidinylphenol represented by: 2. A liquid crystal composition containing at least one ester derivative of optically active benzoic acid and allylpyrimidinylphenol according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16065988A JPH0211576A (en) | 1988-06-30 | 1988-06-30 | Ester derivative of optically active benzoic acid and allylpyrimidinylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16065988A JPH0211576A (en) | 1988-06-30 | 1988-06-30 | Ester derivative of optically active benzoic acid and allylpyrimidinylphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0211576A true JPH0211576A (en) | 1990-01-16 |
Family
ID=15719715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16065988A Pending JPH0211576A (en) | 1988-06-30 | 1988-06-30 | Ester derivative of optically active benzoic acid and allylpyrimidinylphenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0211576A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7059018B2 (en) | 2001-12-06 | 2006-06-13 | Sugatsune Kogyo Co., Ltd. | Hinge with catch |
-
1988
- 1988-06-30 JP JP16065988A patent/JPH0211576A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7059018B2 (en) | 2001-12-06 | 2006-06-13 | Sugatsune Kogyo Co., Ltd. | Hinge with catch |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4754051A (en) | Optically active tolan derivative | |
| JPS61267540A (en) | Novel optically active compound and liquid crystal composition | |
| EP0439190B1 (en) | Component for liquid crystal composition and liquid crystal composition containing the same | |
| US4913838A (en) | Liquid crystal compound with a 4-(optically active alkyl)-3-cyanophenyl group | |
| JPH0416454B2 (en) | ||
| JPS6210045A (en) | Liquid crystal compound and liquid crystal composition | |
| US4943385A (en) | Thioether compound and liquid crystal composition | |
| JPH0211576A (en) | Ester derivative of optically active benzoic acid and allylpyrimidinylphenol | |
| JPS6032748A (en) | Liquid crystal compound | |
| JPH0578548B2 (en) | ||
| JPH01193254A (en) | Ester derivative of allylpyrimidinylphenol | |
| JPH01301650A (en) | Alpha-methylallylphenyl ester derivative of optically active benzoic acid | |
| JPH02200677A (en) | Ester derivative of allylbiphenylcarboxylic acid with fluoropyrimidinylphenols | |
| JPH01275569A (en) | Ester derivative of allylfluoropyrimidinylphenols and liquid crystal thereof | |
| JPS62123153A (en) | Biphenol derivative and liquid crystal composition and optical switching element containing same | |
| JPH05140042A (en) | Unsaturated esters | |
| JPH0320243A (en) | Ester compound | |
| JPH02196756A (en) | Halogenophenyl allylbiphenylcarboxylates | |
| JPS61249953A (en) | Ferroelectric compound and liquid crystal composition | |
| JPS6136251A (en) | Ester derivative of 3-halogeno-4-cyanophenol | |
| JPH02218646A (en) | Liquid crystal ester compound | |
| JPH02212477A (en) | Alkenyl ester derivative of fluorine-substituted phenylpyrimidine | |
| JPH01132548A (en) | Optically active benzoic acid 2-allyphenyl esters | |
| JPH0386845A (en) | High-temperature liquid crystal ester compound | |
| JPH01265077A (en) | 2-allyl-4-pyrimidinyl-6-fluorophenyl esters of optically active benzoic acid |