JPH0320378B2 - - Google Patents
Info
- Publication number
- JPH0320378B2 JPH0320378B2 JP58015247A JP1524783A JPH0320378B2 JP H0320378 B2 JPH0320378 B2 JP H0320378B2 JP 58015247 A JP58015247 A JP 58015247A JP 1524783 A JP1524783 A JP 1524783A JP H0320378 B2 JPH0320378 B2 JP H0320378B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- trans
- represent
- viscosity
- 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 - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ZQWPRMPSCMSAJU-UHFFFAOYSA-N methyl cyclohexanecarboxylate Chemical compound COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- -1 trans-4-[4-(trans-4- Pentylcyclohexyl)phenyl]cyclohexanecarboxylic acid methyl ester Chemical compound 0.000 description 2
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
- GLVQBAYHWDUEQI-YKFMMLSNSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(O)=O)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(O)=O)C=C1 GLVQBAYHWDUEQI-YKFMMLSNSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 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
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
本発明は広い温度範囲で液晶相を示す、低粘性
な新規液晶物質及びそれを含有する液晶組成物に
関する。
液晶を使用した表示素子は時計、電卓などに広
く使用される様になつて来た。この液晶表示素子
は液晶物質の光学異方性及び誘電異方性という性
質を利用したものであるが、液晶相にはネマチツ
ク液晶相、スメクチツク液晶相、コレステリツク
液晶相があり、そのうちネマチツク液晶を利用し
たものが最も広く実用化されている。即ちそれら
にはTN（ねじれネマチツク）型、DS型（動的散
乱型）、ゲスト・ホスト型、DAP型などがあり、
それぞれに使用される液晶物質に要求される性質
は異る。しかし、いずれにしても、これら表示素
子に使用される液晶物質は自然界のなるべく広い
範囲で液晶相を示すものが望ましいが、現在のと
ころ単一物質でその様な条件をみたす様な物質は
なく、数種の液晶物質又は非液晶物質を混合して
一応実用に耐える様な物を得ているのが現状であ
る。又、これらの物質は水分、光、熱、空気等に
対しても安定でなければならないのは勿論であ
り、更に表示素子を駆動させる必要なしきい電
圧、飽和電圧がなるべく低いこと、又応答速度を
早くするためには粘度が出来るだけ低いことが望
ましい。ところで液晶温度範囲を高温の方に広く
するためには高融点の液晶物質を成分として使用
する必要があるが、一般に高融点の液晶物質は粘
度が高く、従つてそれを含む液晶組成物も粘度が
高くなるので、高温、例えば80℃位まで使用出来
る様な液晶表示素子の応答速度、特に低温でのそ
れは著るしくおそくなる傾向にあつた。しかるに
本発明者らは高い液晶温度範囲をもちながら低粘
度の液晶物質を見つけ本発明に到つた。
即ち本発明は一般式
（上式中Ｒ、R′は炭素数１〜10のアルキル基
を示し、
The present invention relates to a new low-viscosity liquid crystal substance that exhibits a liquid crystal phase over a wide temperature range, and to a liquid crystal composition containing the same. Display elements using liquid crystals have come to be widely used in watches, calculators, etc. This liquid crystal display element utilizes the properties of optical anisotropy and dielectric anisotropy of liquid crystal materials, and there are three liquid crystal phases: nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase, among which nematic liquid crystal is used. The one that has been put into practical use is the most widely used. That is, they include TN (twisted nematic) type, DS (dynamic scattering type), guest-host type, DAP type, etc.
The properties required of the liquid crystal materials used for each type are different. However, in any case, it is desirable that the liquid crystal substances used in these display elements exhibit a liquid crystal phase over as wide a range as possible in nature, but there is currently no single substance that satisfies such conditions. Currently, materials that can be put to practical use are obtained by mixing several types of liquid crystal substances or non-liquid crystal substances. In addition, these materials must of course be stable against moisture, light, heat, air, etc., and the threshold voltage and saturation voltage necessary to drive the display element must be as low as possible, and the response speed must be as low as possible. In order to speed up the process, it is desirable that the viscosity be as low as possible. By the way, in order to widen the liquid crystal temperature range toward higher temperatures, it is necessary to use a liquid crystal substance with a high melting point as a component, but liquid crystal substances with a high melting point generally have a high viscosity, and therefore the liquid crystal composition containing it also has a high viscosity. As the temperature increases, the response speed of liquid crystal display elements that can be used at high temperatures, for example, up to about 80° C., particularly at low temperatures, tends to become significantly slower. However, the present inventors found a liquid crystal material with a high liquid crystal temperature range and low viscosity, and arrived at the present invention. That is, the present invention is based on the general formula (In the above formula, R and R' represent an alkyl group having 1 to 10 carbon atoms,
【式】【formula】
【式】はそれぞれ[Formula] is each
【式】又は[Formula] or
【式】を示す。但し、[Formula] is shown. however,
【式】【formula】
【式】共に[formula] together
【式】のときはWhen [expression]
【式】も【Formula】also
【式】である）で表わされ
る三環カルボン酸エステル誘導体及びそれを含有
する液晶組成物である。
本発明の化合物は高い液晶−透明点を有し、低
粘性であり、これを組成物の成分として加えるこ
とによりその液晶組成物の粘度を高くせずに透明
点を上げることが出来る。又水分、熱、光等に対
する安定性も良好である。
次に本発明の化合物の製造法を示す。
それぞれに対応するカルボン酸に塩化チオニル
を作用させて、酸クロリドとし、ついでアルキル
アルコールとピリジン存在下反応して目的物を製
造することが出来る。以上を化学式で示すと、
（Ｒ、R′は前記に同じ）
又、カルボン酸とアルコールを酸触媒の存在下
で反応させても得ることができる。
以下実施例により本発明の化合物につき更に詳
細に説明する。
実施例１ 〔トランス−４−〔４−（トランス−４
−ペンチルシクロヘキシル）フエニル〕シクロ
ヘキサンカルボン酸メチルエステル（（）式
でＲ＝C5H11、R′＝CH3、A tricyclic carboxylic acid ester derivative represented by the following formula and a liquid crystal composition containing the same. The compound of the present invention has a high liquid crystal clearing point and low viscosity, and by adding it as a component of the composition, the clearing point can be raised without increasing the viscosity of the liquid crystal composition. It also has good stability against moisture, heat, light, etc. Next, a method for producing the compound of the present invention will be described. The desired product can be produced by reacting the corresponding carboxylic acid with thionyl chloride to form an acid chloride, and then reacting with an alkyl alcohol in the presence of pyridine. If the above is expressed as a chemical formula, (R and R' are the same as above) It can also be obtained by reacting a carboxylic acid and an alcohol in the presence of an acid catalyst. The compounds of the present invention will be explained in more detail with reference to Examples below. Example 1 [trans-4-[4-(trans-4
-pentylcyclohexyl)phenyl]cyclohexanecarboxylic acid methyl ester (in the formula (), R=C 5 H 11 , R′=CH 3 ,
【式】【formula】
【式】【formula】
【式】のもの）の製造〕
トランス−４−〔４−（トランス−４−ペンチル
シクロヘキシル）フエニル〕シクロヘキサンカル
ボン酸3.6ｇを塩化チオニル10mlと共に80℃に加
熱する。反応液は２時間で均一になり、更に1.5
時間反応をつづける。過剰の塩化チオニルを減圧
にて留去する。残つた油状物は酸塩化物である。
一方メタノール10mlをピリジン20mlと混合してお
いたものに酸塩化物を加えた後にトルエン100ml
を加え、一晩放置する。分液漏斗でそのトルエン
層を、まず6N塩酸で、ついで2N苛性ソーダ溶液
で、最後に水で中性になるまで洗浄する。それを
無水硫酸ナトリウムで乾燥後、トルエン層を減圧
で留去する。残つた油状物をエタノールで再結晶
して目的のトランス−４−〔４−（トランス−４−
ペンチルシクロヘキシル）フエニル〕シクロヘキ
サンカルボン酸メチルエステルを得た。収量1.8
ｇ、収率49％。このもののＣ−Ｓ点は約37℃、Ｓ
−Ｎ点は142.1℃、Ｎ−Ｉ点は160.7℃であつた。
同様にしてトランス−４−〔４−（トランス−４
−ペンチルシクロヘキシル）フエニル〕シクロヘ
キサンカルボン酸の代りにそれぞれに対応する三
環カルボン酸を使用し、又メタノール又はその代
りにエチルアルコールを使用して他の（）式の
三環カルボン酸エステル誘導体を製造した。その
物性値を実施例１のそれと共に第１表に示す。Preparation of [Formula]] 3.6 g of trans-4-[4-(trans-4-pentylcyclohexyl)phenyl]cyclohexanecarboxylic acid is heated to 80°C with 10 ml of thionyl chloride. The reaction solution became homogeneous in 2 hours, and further
Continue the time reaction. Excess thionyl chloride is distilled off under reduced pressure. The oil that remains is the acid chloride.
On the other hand, add acid chloride to a mixture of 10 ml of methanol and 20 ml of pyridine, then add 10 ml of toluene.
Add and leave overnight. Wash the toluene layer in a separatory funnel first with 6N hydrochloric acid, then with 2N caustic soda solution, and finally with water until neutral. After drying it over anhydrous sodium sulfate, the toluene layer was distilled off under reduced pressure. The remaining oil was recrystallized from ethanol to obtain the desired trans-4-[4-(trans-4-
Pentylcyclohexyl)phenyl]cyclohexanecarboxylic acid methyl ester was obtained. Yield 1.8
g, yield 49%. The C-S point of this product is approximately 37℃, S
-N point was 142.1°C, and N-I point was 160.7°C. Similarly, trans-4-[4-(trans-4
-Pentylcyclohexyl)phenyl] Using the corresponding tricyclic carboxylic acid in place of cyclohexanecarboxylic acid, and using methanol or ethyl alcohol in place of it, produce other tricyclic carboxylic acid ester derivatives of formula (). did. The physical property values are shown in Table 1 together with those of Example 1.
【表】【table】
【表】
実施例７（使用例）
トランス−４−プロピル−（4′−シアノフエニ
ル）シクロヘキサン 28％
トランス−４−ペンチル−（4′−シアノフエニ
ル）シクロヘキサン 42％
トランス−４−ヘプチル−（4′−シアノフエニ
ル）シクロヘキサン 30％
なる組成の液晶組成物のＮ−Ｉ点は52℃である。
この液晶組成物をセル厚10μmのTNセル（ねじ
れネマチツクセル）に封入したものの動作しきい
電圧は1.53V、飽和電圧は2.12Vであつた。又粘
度は20℃で23cpであつた。
この液晶組成物95部に実施例１で製造したトラ
ンス−４−〔４−（トランス−４−ペンチルシクロ
ヘキシル）フエニル〕シクロヘキサンカルボン酸
メチルエステルを５部加えたもののＮ−Ｉ点は57
℃になつた。しきい電圧は1.55V、飽和電圧は
2.14Vであつた。又粘度は20℃で23cpであつた。[Table] Example 7 (Usage example) Trans-4-propyl-(4'-cyanophenyl)cyclohexane 28% Trans-4-pentyl-(4'-cyanophenyl)cyclohexane 42% Trans-4-heptyl-(4'- The N-I point of a liquid crystal composition having a composition of 30% cyanophenylcyclohexane is 52°C.
When this liquid crystal composition was sealed in a TN cell (twisted nematic cell) with a cell thickness of 10 μm, the operating threshold voltage was 1.53V and the saturation voltage was 2.12V. The viscosity was 23 cp at 20°C. When 5 parts of trans-4-[4-(trans-4-pentylcyclohexyl)phenyl]cyclohexanecarboxylic acid methyl ester prepared in Example 1 was added to 95 parts of this liquid crystal composition, the N-I point was 57.
It has become ℃. Threshold voltage is 1.55V, saturation voltage is
It was 2.14V. The viscosity was 23 cp at 20°C.
Claims (1)
を示し、【式】【式】 【式】はそれぞれ【式】又は 【式】を示す。但し【式】 【式】共に【式】のときは 【式】も【式】である。） で表わされる三環カルボン酸エステル誘導体。 ２ 一般式 （上式中Ｒ、R′は炭素数１〜10のアルキル基
を示し、【式】【式】 【式】はそれぞれ【式】又は 【式】を示す。但し【式】 【式】共に【式】のときは 【式】も【式】である。） で表わされる三環カルボン酸エステル誘導体を少
くとも一種含有することを特徴とする液晶組成
物。[Claims] 1. General formula (In the above formula, R and R' represent an alkyl group having 1 to 10 carbon atoms, and [Formula], [Formula], and [Formula] each represent [Formula] or [Formula]. However, [Formula] and [Formula] both represent [Formula] and [Formula]. When [formula] is [formula], [formula] is also [formula].) A tricyclic carboxylic acid ester derivative represented by. 2 General formula (In the above formula, R and R' represent an alkyl group having 1 to 10 carbon atoms, and [Formula], [Formula], and [Formula] each represent [Formula] or [Formula]. However, [Formula] and [Formula] both represent [Formula] and [Formula]. When [formula] is [formula], [formula] is also [formula].) A liquid crystal composition characterized by containing at least one tricyclic carboxylic acid ester derivative represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1524783A JPS59141540A (en) | 1983-02-01 | 1983-02-01 | Tricyclic carboxylic acid ester derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1524783A JPS59141540A (en) | 1983-02-01 | 1983-02-01 | Tricyclic carboxylic acid ester derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59141540A JPS59141540A (en) | 1984-08-14 |
| JPH0320378B2 true JPH0320378B2 (en) | 1991-03-19 |
Family
ID=11883523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1524783A Granted JPS59141540A (en) | 1983-02-01 | 1983-02-01 | Tricyclic carboxylic acid ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59141540A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0168701B1 (en) * | 1984-07-14 | 1988-11-02 | MERCK PATENT GmbH | Tercyclohexyles |
| JPS62106061A (en) * | 1985-11-01 | 1987-05-16 | Dainippon Ink & Chem Inc | Optically active benzoic acid ester derivative |
| EP0253501A3 (en) * | 1986-07-16 | 1990-04-04 | Imperial Chemical Industries Plc | N-disubstituted cycloalkylmethyl amines useful as fungicides |
| MXPA05011536A (en) * | 2003-04-30 | 2006-01-23 | Inst For Pharm Discovery Inc | Phenyl substituted carboxylic acids. |
| CA2670736A1 (en) | 2006-11-29 | 2008-06-05 | Abbott Laboratories | Inhibitors of diacylglycerol o-acyltransferase type 1 enzyme |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58189124A (en) * | 1982-03-30 | 1983-11-04 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Hydroterphenyl compound |
-
1983
- 1983-02-01 JP JP1524783A patent/JPS59141540A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58189124A (en) * | 1982-03-30 | 1983-11-04 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Hydroterphenyl compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59141540A (en) | 1984-08-14 |
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