JPH041000B2 - - Google Patents
Info
- Publication number
- JPH041000B2 JPH041000B2 JP3560683A JP3560683A JPH041000B2 JP H041000 B2 JPH041000 B2 JP H041000B2 JP 3560683 A JP3560683 A JP 3560683A JP 3560683 A JP3560683 A JP 3560683A JP H041000 B2 JPH041000 B2 JP H041000B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- dihydrocholesterol
- cholesterol
- fluorobenzoic acid
- 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
Links
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 10
- 239000004973 liquid crystal related substance Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 claims description 7
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims description 7
- 235000012000 cholesterol Nutrition 0.000 claims description 5
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000001840 cholesterol esters Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 7
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- MCSXGHLTXBACQB-UHFFFAOYSA-N [10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 4-nitrobenzoate Chemical compound C1CC2(C)C3CCC4(C)C(C(C)CCCC(C)C)CCC4C3CC=C2CC1OC(=O)C1=CC=C([N+]([O-])=O)C=C1 MCSXGHLTXBACQB-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) 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
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Liquid Crystal (AREA)
Description
本発明は光学活性なら旋分子構造を持つた化合
物及びそれを含有する液晶組成物に関する。
液晶表示素子は液晶物質の特性である光学異方
性及び誘電異方性を利用したもので各種の表示方
式のものがあるが、そのうち現在最も実用化され
ているのはねじれネマチツク型（TN型）、動的
散乱型（DS型）などである。最近は他の方式の
液晶表示方法の開発も盛んに行なわれ、中でもコ
レステリツク・ネマチツク相転移型表示及びホワ
イト・テイラー型カラー表示などがその代表的な
ものである。これらの表示素子に用いられる液晶
組成物はいずれもネマチツク液晶に光学活性物質
などを添加して、それぞれに適したコレステリツ
クのら旋ピツチをもつ様に調節される。添加する
光学活性物質の分子はねじれたら旋構造をもち、
そのら旋ピツチは短かく、かつ熱、光、空気、水
に安定なものが望まれている。本発明の化合物は
以上の様な用途に使用して有用な新規な光学活性
を有し、ねじれた分子構造をもつ化合物である。
即ち本発明は一般式
（上式中
The present invention relates to an optically active compound having a rotary molecular structure and a liquid crystal composition containing the same. Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy that are the characteristics of liquid crystal materials, and there are various display methods, but the currently most practically used type is the twisted nematic type (TN type). ), dynamic scattering type (DS type), etc. Recently, other types of liquid crystal display methods have been actively developed, and representative examples include cholesteric-nematic phase transition type display and White-Taylor type color display. The liquid crystal compositions used in these display devices are each adjusted to have an appropriate cholesteric helical pitch by adding an optically active substance to a nematic liquid crystal. The molecules of the optically active substance added have a twisted helical structure,
It is desired that the spiral pitch be short and stable against heat, light, air, and water. The compound of the present invention has a novel optical activity useful for the above-mentioned applications, and has a twisted molecular structure. That is, the present invention is based on the general formula (In the above formula
【式】は【ceremony
【式】 又は【formula】 or
【式】を示す）
で表わされる４−フルオロ安息香酸のジヒドロコ
レステロール又はコレステロールのエステル及び
それを含有する液晶組成物である。
本発明の化合物はら旋分子構造をもち、高温ま
でコレステリツク液晶相を示し、これをネマチツ
ク液晶に少量添加してコレステリツク・ネマチツ
ク相転移型表示素子用又はホワイト・テーラー型
表示素子用の液晶組成物を得ることが出来る。こ
の化合物をネマチツク液晶に10重量％添加して測
定して得られるら旋ピツチの値から得られるこの
化合物自体のら旋ピツチは2μm程度である。又、
この化合物をTN型表示素子用のネマチツク液晶
組成物に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）の発生を少くして、その性能
を改善することが出来る。
つぎに本発明による化合物の製造法について述
べると、市販の４−フルオロ安息香酸クロリドと
ジヒドロコレステロール又はコレステロールとを
ピリジンの存在下で反応させて、目的の４−フル
オロ安息香酸のジヒドロコレステロール又はコレ
ステロールのエステルを製造することができる。
化学式で示すと
（上式中It is an ester of dihydrocholesterol or cholesterol of 4-fluorobenzoic acid represented by the following formula and a liquid crystal composition containing the same. The compound of the present invention has a helical molecular structure and exhibits a cholesteric liquid crystal phase up to high temperatures, and by adding a small amount to a nematic liquid crystal, a liquid crystal composition for a cholesteric-nematic phase transition type display element or a White-Taylor type display element can be prepared. You can get it. The helical pitch of this compound itself, obtained from the helical pitch value obtained by adding 10% by weight of this compound to a nematic liquid crystal and measuring it, is about 2 μm. or,
When this compound is added to a nematic liquid crystal composition for a TN display element, it is possible to reduce the occurrence of striped patterns (so-called reverse domains) on the display surface and improve its performance. Next, the method for producing the compound according to the present invention will be described. Commercially available 4-fluorobenzoic acid chloride and dihydrocholesterol or cholesterol are reacted in the presence of pyridine to produce the desired dihydrocholesterol or cholesterol of 4-fluorobenzoic acid. Esters can be produced. Shown as a chemical formula (In the above formula
ジヒドロコレステロール3.9gをピリジン30mlに
溶解し、これに４−フルオロ安息香酸クロリド
1.6gを加えて室温で撹拌して反応させた。更にト
ルエン50mlを加えよく混合して一晩放置してから
水100mlにあけ、トルエン50mlを加えて抽出した。
トルエン層を6N塩酸で、ついで2N荷性ソーダ水
溶液で洗浄した後、中性になるまで水洗した。次
いで無水硫酸ナトリウムを用いて乾燥後、トルエ
ンを減圧で留去し、残つた結晶物をアセトン−ト
ルエンの混合溶媒で再結晶させ目的のジヒドロコ
レステリル−４−フルオロベンゾアートを3.5g
（収率66％）得た。このもののＣ−Ch点は135.8〜
137.2℃、Ch−Ｉ点は147.6℃であつた。
実施例 ２
〔コレステリル−４−フルオロベンゾアートの
製造〕
実施例１におけるジヒドロコレステロールの代
りにコレステロール3.9gを使用した他は実施例１
に準じて操作を行ないコレステリル−４−フルオ
ロベンゾアートを3.2g（収率60％）得た。このも
ののＣ−Ch点は153.4〜155.1℃、Ch−Ｉ点は
169.2℃であつた。
実施例 ３（使用例）
オクタデシル−トリ−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、GR−63な
る液晶組成物（チツソ(株)市販品 ネマチツク液晶
で、組成は下記(A)の通り）90重量部と本発明の実
施例１によるジヒドロコレステリル−４−フルオ
ロベンゾアート10重量部からなる液晶組成物を密
封したコレステリツク−ネマチツク相転移表示素
子の作動しきい値電圧は10.0Vであつた。
Dissolve 3.9 g of dihydrocholesterol in 30 ml of pyridine, and add 4-fluorobenzoic acid chloride to this.
1.6 g was added and stirred at room temperature to react. Furthermore, 50 ml of toluene was added, mixed well, and left overnight, then poured into 100 ml of water, and extracted with 50 ml of toluene.
The toluene layer was washed with 6N hydrochloric acid, then with a 2N aqueous sodium chloride solution, and then with water until neutral. After drying over anhydrous sodium sulfate, toluene was distilled off under reduced pressure, and the remaining crystals were recrystallized with a mixed solvent of acetone and toluene to obtain 3.5 g of dihydrocholesteryl-4-fluorobenzoate.
(yield 66%). The C-Ch point of this is 135.8 ~
The temperature was 137.2°C, and the Ch-I point was 147.6°C. Example 2 [Production of cholesteryl-4-fluorobenzoate] Example 1 except that 3.9 g of cholesterol was used instead of dihydrocholesterol in Example 1.
3.2 g (yield: 60%) of cholesteryl-4-fluorobenzoate was obtained. The C-Ch point of this product is 153.4-155.1℃, and the Ch-I point is
It was 169.2℃. Example 3 (Example of use) A liquid crystal composition called GR-63 (commercial product of Chitsuso Co., Ltd., nematic liquid crystal, with the following composition (A )) and 10 parts by weight of dihydrocholesteryl-4-fluorobenzoate according to Example 1 of the present invention, the operating threshold voltage of the cholesteric-nematic phase change display element is 10.0V. It was hot.
Claims (1)
レステロール又はコレステロールのエステルによ
る光学活性物質。 ２ 一般式 （上式中【式】は【式】 又は【式】を示す） で表わされる４−フルオロ安息香酸のジヒドロコ
レステロール又はコレステロールのエステルによ
る光学活性物質を少くとも１成分含むことを特徴
とする液晶組成物。[Claims] 1. General formula (In the above formula, [formula] represents [formula] or [formula]) An optically active substance made of dihydrocholesterol or cholesterol ester of 4-fluorobenzoic acid. 2 General formula (In the above formula, [Formula] represents [Formula] or [Formula]) A liquid crystal composition characterized by containing at least one optically active substance consisting of dihydrocholesterol of 4-fluorobenzoic acid or an ester of cholesterol. thing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3560683A JPS59161399A (en) | 1983-03-04 | 1983-03-04 | Optically active substance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3560683A JPS59161399A (en) | 1983-03-04 | 1983-03-04 | Optically active substance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59161399A JPS59161399A (en) | 1984-09-12 |
| JPH041000B2 true JPH041000B2 (en) | 1992-01-09 |
Family
ID=12446483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3560683A Granted JPS59161399A (en) | 1983-03-04 | 1983-03-04 | Optically active substance |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59161399A (en) |
-
1983
- 1983-03-04 JP JP3560683A patent/JPS59161399A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59161399A (en) | 1984-09-12 |
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