JPH0374350A - Optically active methyladipic acid esters - Google Patents
Optically active methyladipic acid estersInfo
- Publication number
- JPH0374350A JPH0374350A JP21046689A JP21046689A JPH0374350A JP H0374350 A JPH0374350 A JP H0374350A JP 21046689 A JP21046689 A JP 21046689A JP 21046689 A JP21046689 A JP 21046689A JP H0374350 A JPH0374350 A JP H0374350A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- formulas
- tables
- optically active
- 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.)
- Granted
Links
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical class OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 title description 2
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 13
- -1 ester compound Chemical class 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 5
- 230000003098 cholesteric effect Effects 0.000 abstract description 5
- 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 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- GAYWCADKXYCKCG-UHFFFAOYSA-N 5-pyridin-3-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1NC(=S)N=C1C1=CC=CN=C1 GAYWCADKXYCKCG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 2
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- SYEOWUNSTUDKGM-RXMQYKEDSA-N (3r)-3-methylhexanedioic acid Chemical compound OC(=O)C[C@H](C)CCC(O)=O SYEOWUNSTUDKGM-RXMQYKEDSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- SYEOWUNSTUDKGM-YFKPBYRVSA-N 3-methyladipic acid Chemical compound OC(=O)C[C@@H](C)CCC(O)=O SYEOWUNSTUDKGM-YFKPBYRVSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000007787 solid Substances 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- 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、光学活性な、ら旋分子構造を持った化合物及
びそれを含有する（夜晶化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an optically active compound having a helical molecular structure and a night crystal compound containing the same.
なる２１Ｔから選ばれた一つであることを示す）で表さ
れる光学活性メチルアジピン酸のニスデル類を少なくと
も一種含有して１２る液晶組成物。12. A liquid crystal composition containing at least one Nisdel type of optically active methyladipate represented by the formula 12 selected from 21T.
〔従来の技術とその問題点）
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、そのうち現在量も実用化されているのはねじれネマ
チック型（ＴＮ型）、動的散乱型（ＤＳ型）、などであ
る。しかし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、中でもコレステリック・ネマチック相転移
型表示及びホワイト・ティラー型カラー表示などがその
代表的なものである。[Prior art and its problems] Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy that are characteristics of liquid crystal materials, and there are various display methods, but none of them are currently in practical use. The types include twisted nematic type (TN type), dynamic scattering type (DS type), etc. However, recently, other types of liquid crystal display methods have been actively developed, and representative examples include cholesteric-nematic phase transition type display and white-tiller type color display.
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
マチッ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ックのら旋ピッ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、そのら旋ビッヂは短かく、かつ熱、光、空気
、水に安定なものが望まれている。The liquid crystal compositions used in these display elements are each adjusted to have an appropriate cholesteric helical pitch by adding an optically active substance to nematic liquid crystal. It is desired that the molecules of the optically active substance to be added have a twisted, helical structure, the helical bridge is short, and it is stable against heat, light, air, and water.
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、ねしれた分子構造をもつ化合物であ
る。The compound of the present invention has novel optical activity useful for the above-mentioned applications and has a twisted molecular structure.
（問題点を解決する手段）
本発明壮一般式
なる群から選ばれた一つであることを示す）で表わされ
る光学活性メチルアジピン酸のエステル類４ｊよびこれ
を含有してなる液晶組成物である。(Means for Solving the Problems) The optically active methyl adipic acid esters 4j represented by the formula (indicating that it is one selected from the group of general formulas of the present invention) and a liquid crystal composition containing the same. be.
（上式中Ｒは直釦又は枝別れした炭素数１〜１５の〔化
合物の製造法〕
本発明の化合物の製造法は次式の反応式にょってポされ
る。(In the above formula, R is a straight button or a branched carbon number of 1 to 15 [Production method of compound]) The production method of the compound of the present invention is carried out by the following reaction formula.
すなわち、
光学活性３
メヂルアジピン酸を塩化
チオニルで酸塩化物とし、ついでアルコール類をピリジ
ン存在下反応をして目的の光学活性３−メチルアジピン
酸のエステル類を製造した。That is, optically active 3-methyladipic acid was converted into an acid chloride with thionyl chloride, and then an alcohol was reacted in the presence of pyridine to produce the desired esters of optically active 3-methyladipate.
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・スメクチック液晶を示し、又液晶となら
ないものもあるか、これをネマチック液晶に少量添加し
てコレステリック・ネマヂック相転移表示素子用又はホ
ワイト・テーラ−型表示素子用の液晶組成物を得ること
が出来る。The compounds of the present invention have a helical molecular structure, and some exhibit cholesteric/smectic liquid crystals, while others do not form liquid crystals, or they can be added to nematic liquid crystals in small amounts for use in cholesteric/nematic phase transition display elements or A liquid crystal composition for 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。又、この化合物
をＴＮ型表示素子用のネマチッ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
生を少なくして、その性能を改善することか出来る。The helical pitch of this compound itself, 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. Furthermore, when this compound is added to a nematic liquid crystal composition for a TN type display element, it is possible to reduce the occurrence of striped patterns (so-called reverse domains) on the display surface and improve its performance.
以下実施例により本化合物につき更に詳細に説明する。The present compound will be explained in more detail with reference to Examples below.
実施例１
ビス−４−（＋−ランス−４−プロピルシクロヘキシル
）フェニル（Ｒ） −（＋）−３−メチルアジペートの
製造
（式中Ｒ−Ｃｓ ）ｌ ７ 、−０−−ニド（）今示す
。）市販の（Ｒ） −（＋）−３−メチルアジピン酸１
．６ｇと大過剰の塩化チオニルをマントルヒーター上で
還流を３時間行った。過剰の塩化チオニルを減圧で完全
に留去した。残った油状物が酸塩化物である。別の反応
容器に４−（トランス−４−プロピルシクロヘキシル）
フェノール４１ｇをピリジン２０ｍｆｔにとかしておく
。これに酸塩化物を加えて室温で攪拌して反応させた。Example 1 Preparation of bis-4-(+-lance-4-propylcyclohexyl)phenyl (R)-(+)-3-methyladipate (in the formula R-Cs)l7, -0--nido()now show. ) Commercially available (R)-(+)-3-methyladipic acid 1
．． A large excess of 6 g of thionyl chloride was refluxed on a mantle heater for 3 hours. Excess thionyl chloride was completely distilled off under reduced pressure. The oil that remains is the acid chloride. 4-(trans-4-propylcyclohexyl) in a separate reaction vessel.
Dissolve 41 g of phenol in 20 mft of pyridine. Acid chloride was added to this, and the mixture was stirred and reacted at room temperature.
更にトルエン５０ｍＪ２を加えよく混合して一晩放置し
てから水１００ｍＡにあけ、トルエン２５０ｍｊｌを加
えて抽出する。トルエン層を６Ｎ塩酸で、ついで２Ｎ苛
性ソーダ水溶液て洗浄した後、中性になるまて水洗する
。Further, 50 mJ2 of toluene was added, mixed well, left overnight, poured into 100 mA of water, and extracted with 250 mJl of toluene. The toluene layer was washed with 6N hydrochloric acid, then with 2N aqueous sodium hydroxide solution, and then washed with water until neutral.
トルエン層を無水硫酸ナトリウムで乾燥後、トエンを減
圧で留去し、残った結晶物をエタノールで再結晶して目
的のビス−４−（ｈランス−４−）゛ロヒ。After drying the toluene layer over anhydrous sodium sulfate, the toene was distilled off under reduced pressure, and the remaining crystalline material was recrystallized from ethanol to obtain the desired bis-4-(h-lance-4-) compound.
ルシクロヘキシル）フェニル（Ｒ） −（＋）−３−メ
チルアジピン酸・を製造した。cyclohexyl)phenyl(R)-(+)-3-methyladipic acid.
この化合物の固体−スメクチ・ンク（Ｃ−５ｍ”） ｉ
ま１２（１，４〜１２１．３℃、スメクチ・ンクー透明
点（Ｓｍ”Ｉ）は １４００℃であった。収量ｔ、ａｇ
（収率４９％）。２５℃でのピッチは２３．３μｍであ
った。The solid state of this compound - smectin (C-5m") i
12 (1.4 - 121.3℃, Smectinku clearing point (Sm"I) was 1400℃. Yield t, ag
(Yield 49%). The pitch at 25°C was 23.3 μm.
実施例２〜４
実ｔｉ 例１における４−（）ランス−４−プロピルシ
クロヘキシル）フェノールの代りに種々のアルコールを
用いて（Ｒ） −（＋）−３−メチルアジピン酸のエス
テル類を製造した。Examples 2 to 4 Practical esters of (R)-(+)-3-methyladipic acid were produced using various alcohols in place of 4-()lans-4-propylcyclohexyl)phenol in Example 1. .
その物性値を実施例１の結果と共に第１表にポす。The physical property values are listed in Table 1 along with the results of Example 1.
応用例
オクタデシル−トリーエトキシシランて垂直配向処理を
したセル厚１０５μｍのセルに、ＧＲ−６３なる液晶組
成物（ビフェニル系組成物、ヂッソ■市販品）９０部と
本発明実施例１のビス−４−（トランス４−プロピルシ
クロヘキシル）フェニル（Ｒ） −Ｈ３−メヂルアジベ
ート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＋２．ＯＶであった。Application Example 90 parts of a liquid crystal composition called GR-63 (biphenyl composition, commercially available from Jisso) and Bis-4 of Example 1 of the present invention were placed in a cell having a cell thickness of 105 μm that had been vertically aligned using octadecyl-triethoxysilane. A cholesteric-nematic phase transition display element is obtained by sealing a liquid crystal composition consisting of 10 parts of -(trans-4-propylcyclohexyl)phenyl(R)-H3-medyladibate, and its operating threshold voltage is +2. It was OV.
以 上that's all
Claims (2)
キル基またはアルコキシ基であり、▲数式、化学式、表
等があります▼は▲数式、化学式、表等があります▼ ▲数式、化学式、表等があります▼ なる群から選ばれた一つであることを示す）で表される
光学活性メチルアジピン酸のエステル化合物。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the above formula, R is a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ is an optically active methyl adipic acid ester compound represented by ▲ has mathematical formulas, chemical formulas, tables, etc. ▼ ▲ has mathematical formulas, chemical formulas, tables, etc. ▼ indicates one selected from the group.
キル基またはアルコキシ基であり、▲数式、化学式、表
等があります▼は▲数式、化学式、表等があります▼ ▲数式、化学式、表等があります▼ なる群から選ばれた一つであることを示す）で表される
光学活性メチルアジピン酸のエステル類を少なくとも一
種含有してなる液晶組成物。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the above formula, R is a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A liquid crystal composition containing one type of liquid crystal composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21046689A JP2767294B2 (en) | 1989-08-15 | 1989-08-15 | Esters of optically active methyladipic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21046689A JP2767294B2 (en) | 1989-08-15 | 1989-08-15 | Esters of optically active methyladipic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0374350A true JPH0374350A (en) | 1991-03-28 |
| JP2767294B2 JP2767294B2 (en) | 1998-06-18 |
Family
ID=16589804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21046689A Expired - Lifetime JP2767294B2 (en) | 1989-08-15 | 1989-08-15 | Esters of optically active methyladipic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2767294B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015044794A (en) * | 2013-07-30 | 2015-03-12 | 株式会社半導体エネルギー研究所 | Organic compound, liquid crystal composition, liquid crystal element, and liquid crystal display device |
-
1989
- 1989-08-15 JP JP21046689A patent/JP2767294B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015044794A (en) * | 2013-07-30 | 2015-03-12 | 株式会社半導体エネルギー研究所 | Organic compound, liquid crystal composition, liquid crystal element, and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2767294B2 (en) | 1998-06-18 |
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