JPH0443897B2 - - Google Patents
Info
- Publication number
- JPH0443897B2 JPH0443897B2 JP58048438A JP4843883A JPH0443897B2 JP H0443897 B2 JPH0443897 B2 JP H0443897B2 JP 58048438 A JP58048438 A JP 58048438A JP 4843883 A JP4843883 A JP 4843883A JP H0443897 B2 JPH0443897 B2 JP H0443897B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- trans
- viscosity
- crystal composition
- 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 29
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 alcohol ester Chemical class 0.000 description 4
- 239000000463 material 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JXPGQFKJNKWDKP-KTSLABGISA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 JXPGQFKJNKWDKP-KTSLABGISA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- CIOXTSWQGUAVPU-UHFFFAOYSA-N 2,2,2-trifluoroethyl cyclohexanecarboxylate Chemical compound FC(F)(F)COC(=O)C1CCCCC1 CIOXTSWQGUAVPU-UHFFFAOYSA-N 0.000 description 1
- QKEBUASRTJNJJS-UHFFFAOYSA-N 4-[4-(4-pentylcyclohexyl)phenyl]benzonitrile Chemical group C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 QKEBUASRTJNJJS-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
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001035 drying 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
本発明は低粘性な新規液晶性物質及びそれを含
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。本発明の
化合物はその様な場合液晶組成物の一成分として
加えることにより、その粘度を低くするのに有用
な液晶性化合物である。
即ち本発明は一般式
（上式中Ｒは水素又は炭素数１〜15のアルキル基
を示し、
The present invention relates to a new low-viscosity liquid crystal substance and 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 a result, 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, has tended to become significantly slower. The compound of the present invention is a liquid crystalline compound useful for lowering the viscosity of a liquid crystal composition by adding it as a component in such a case. That is, the present invention is based on the general formula (In the above formula, R represents hydrogen or an alkyl group having 1 to 15 carbon atoms,
【式】および[expression] and
【式】は それぞれ【ceremony Each
【式】又は[Formula] or
【式】を示
す）
で表わされるカルボン酸とトリフルオロエタノー
ルのエステル及びそれを含有する液晶組成物であ
る。
本発明の化合物はスメクチツク液晶相を示すも
のと、示さないものとあるが、いずれも低粘度で
あり、これを液晶組成物の成分として加える事に
よりその液晶組成物の粘度を下げることができ
る。またしきい値電圧も下げることが出来る。又
水分、熱、光、空気に対する安定性も良好であ
る。
つぎに本発明の化合物の製造方法を示す。まず
最終目的物に対応するカルボン酸を塩化チオニル
で酸クロリドとし、ついでピリジン存在下最終目
的物に対応するトリフルオロメチルアルキルアル
コールと反応して目的のカルボン酸のトリフルオ
ロメチルアルキルアルコールのエステルを得る。
以上を化学式で示すと、
（上式中Ｒ、An ester of a carboxylic acid and trifluoroethanol represented by the following formula, and a liquid crystal composition containing the same. The compounds of the present invention may or may not exhibit a smectic liquid crystal phase, but both have low viscosity, and by adding them as a component of a liquid crystal composition, the viscosity of the liquid crystal composition can be lowered. It is also possible to lower the threshold voltage. It also has good stability against moisture, heat, light, and air. Next, a method for producing the compound of the present invention will be described. First, the carboxylic acid corresponding to the final target product is converted into an acid chloride with thionyl chloride, and then reacted with trifluoromethylalkyl alcohol corresponding to the final target product in the presence of pyridine to obtain the trifluoromethylalkyl alcohol ester of the target carboxylic acid. . If the above is expressed as a chemical formula, (R in the above formula,
トランス−４−（トランス−４−プロピルシク
ロヘキシル）シクロヘキサンカルボン酸2.5ｇを
塩化チオニル20ml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。
残つた油状物は酸クロリドである。一方２，２，
２−トリフルオロエタノール２ｇをピリジン20ml
に溶か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−（トラン
ス−４−プロピルシクロヘキシル）シクロヘキサ
ンカルボン酸−２，２，２−トリフルオロエチル
エステルを製造した。収量１ｇ、収率43％。
そのＣ−Ｓ点（スメクチツク点）は33.3℃、Ｓ
−Ｉ点（透明点）は38.7℃、粘度は10cpと極めて
低い値であつた。
実施例 ２〜５
実施例１と同様な方法で実施例１におけるトラ
ンス−４−（トランス−４−プロピルシクロヘキ
シル）シクロヘキサンカルボン酸の代りに目的物
に対応するカルボン酸を使用して第１表の実施例
２〜５の化合物を製造した。それらの物性値を実
施例１のそれと共に第１表に示す。
2.5 g of trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid are heated to 80 DEG C. with 20 ml of thionyl chloride. The reaction solution became homogeneous in 2 hours, and the reaction was continued for an additional 1.5 hours. Excess thionyl chloride is distilled off under reduced pressure.
The oil that remains is the acid chloride. On the other hand, 2, 2,
2-trifluoroethanol 2g to pyridine 20ml
After adding the acid chloride to the solution, add 100 ml of toluene and leave it 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 produce the desired trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid-2,2,2-trifluoroethyl ester. Yield 1g, yield 43%. Its C-S point (smectic point) is 33.3℃, S
The -I point (clearing point) was 38.7°C, and the viscosity was extremely low at 10 cp. Examples 2 to 5 In the same manner as in Example 1, using the carboxylic acid corresponding to the target product in place of trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid in Example 1, the preparations shown in Table 1 were carried out. Compounds of Examples 2-5 were prepared. Their physical property values are shown in Table 1 together with those of Example 1.
【表】
実施例 ６（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 24％
トランス−４−ペンチル−（4′−シアノフエニル）
シクロヘキサン 36％
トランス−４−ヘプチル−（4′−シアノフエニル）
シクロヘキサン 25％
４−シアノ−4′−（トランス−４−ペンチルシク
ロヘキシル）ビフエニル 15％
なる組成の液晶組成物のＮ−Ｉ点は72℃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1.83V、飽和電圧は2.53Vであつた。又粘
度は20℃で28cpであつた。この液晶組成物90部
に、実施例１で製造したトランス−４−（トラン
ス−４−プロピルシクロヘキシル）シクロヘキサ
ンカルボン酸−２，２，２−トリフルオロエチル
エステル10部を加えた液晶組成物のＮ−Ｉ点は66
℃であり、しきい電圧は1.50V、飽和電圧は
2.10Vに下がり、又粘度も20℃で24cpに下がつ
た。
実施例 ７（使用例）
実施例６で母晶液として用いたものと同一組成
の液晶組成物90部に、実施例２で製造した４−
（トランス−４−プロピルシクロヘキシル）安息
香酸−２，２，２−トリフルオロエチルエステル
10部を加えた。
かくして得られた液晶組成物のＮ−Ｉ点は64.6
℃であり、しきい電圧は1.39V、飽和電圧は
2.01Vであり、粘度は20℃で24.5cpであつた。
実施例 ８（使用例）
実施例６で母晶液として用いたものと同一組成
の液晶組成物90部に、実施例４で製造した4′−ペ
ンチル−ビフエニリル−４−カルボン酸−２，
２，２−トリフルオロエチルエステル10部を加え
た。
かくして得られた液晶組成物のＮ−Ｉ点は63.2
℃、しきい電圧は1.28V、飽和電圧は1.98Vであ
り、粘度は20℃で25.6cpであつた。[Table] Example 6 (Usage example) Trans-4-propyl-(4'-cyanophenyl)
Cyclohexane 24% trans-4-pentyl-(4'-cyanophenyl)
Cyclohexane 36% trans-4-heptyl-(4'-cyanophenyl)
The N-I point of a liquid crystal composition having a composition of 25% cyclohexane and 15% 4-cyano-4'-(trans-4-pentylcyclohexyl)biphenyl is 72°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 1.83V and the saturation voltage was 2.53V. The viscosity was 28 cp at 20°C. A liquid crystal composition prepared by adding 10 parts of trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid-2,2,2-trifluoroethyl ester prepared in Example 1 to 90 parts of this liquid crystal composition. -I point is 66
℃, the threshold voltage is 1.50V, and the saturation voltage is
The voltage decreased to 2.10V, and the viscosity also decreased to 24cp at 20℃. Example 7 (Example of use) 4-4 produced in Example 2 was added to 90 parts of a liquid crystal composition having the same composition as that used as the mother crystal liquid in Example 6.
(trans-4-propylcyclohexyl)benzoic acid-2,2,2-trifluoroethyl ester
Added 10 parts. The N-I point of the liquid crystal composition thus obtained is 64.6.
℃, the threshold voltage is 1.39V, and the saturation voltage is
The voltage was 2.01V, and the viscosity was 24.5 cp at 20°C. Example 8 (Usage example) 4'-pentyl-biphenylyl-4-carboxylic acid-2, produced in Example 4, was added to 90 parts of a liquid crystal composition having the same composition as that used as the mother crystal liquid in Example 6.
10 parts of 2,2-trifluoroethyl ester were added. The N-I point of the liquid crystal composition thus obtained is 63.2.
℃, the threshold voltage was 1.28V, the saturation voltage was 1.98V, and the viscosity was 25.6cp at 20℃.
Claims (1)
を示し、【式】および【式】は それぞれ【式】又は【式】を示 す） で表わされるカルボン酸とトリフルオロエタノー
ルのエステル。 ２ 一般式 （上式中Ｒは水素又は炭素数１〜15のアルキル基
を示し、【式】および【式】は それぞれ【式】又は【式】を示 す） で表わされるカルボン酸とトリフルオロエタノー
ルのエステルを少くとも一種含有することを特徴
とする液晶組成物用の粘度低下剤。[Claims] 1. General formula (In the above formula, R represents hydrogen or an alkyl group having 1 to 15 carbon atoms, and [Formula] and [Formula] represent [Formula] or [Formula], respectively.) An ester of a carboxylic acid and trifluoroethanol represented by the following. 2 General formula (In the above formula, R represents hydrogen or an alkyl group having 1 to 15 carbon atoms, and [Formula] and [Formula] represent [Formula] or [Formula], respectively.) An ester of carboxylic acid and trifluoroethanol represented by A viscosity reducing agent for a liquid crystal composition, characterized in that it contains at least one type of viscosity reducing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58048438A JPS59175454A (en) | 1983-03-23 | 1983-03-23 | Ester of fluorinated alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58048438A JPS59175454A (en) | 1983-03-23 | 1983-03-23 | Ester of fluorinated alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59175454A JPS59175454A (en) | 1984-10-04 |
| JPH0443897B2 true JPH0443897B2 (en) | 1992-07-20 |
Family
ID=12803352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58048438A Granted JPS59175454A (en) | 1983-03-23 | 1983-03-23 | Ester of fluorinated alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59175454A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993003113A1 (en) * | 1991-08-03 | 1993-02-18 | MERCK Patent Gesellschaft mit beschränkter Haftung | Liquid-crystal compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58154532A (en) * | 1982-02-20 | 1983-09-14 | 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 | Bicyclohexyl derivative |
-
1983
- 1983-03-23 JP JP58048438A patent/JPS59175454A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58154532A (en) * | 1982-02-20 | 1983-09-14 | 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 | Bicyclohexyl derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59175454A (en) | 1984-10-04 |
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