JPS64384B2 - - Google Patents
Info
- Publication number
- JPS64384B2 JPS64384B2 JP6195881A JP6195881A JPS64384B2 JP S64384 B2 JPS64384 B2 JP S64384B2 JP 6195881 A JP6195881 A JP 6195881A JP 6195881 A JP6195881 A JP 6195881A JP S64384 B2 JPS64384 B2 JP S64384B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- trans
- type
- carboxylic 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
- -1 carboxylic acid ester derivative of pentafluorophenol Chemical class 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 3
- 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 2
- OQIHEFMTIUJJET-HDRKRICHSA-N CC[C@H]1CC[C@@H](CC1)[C@H]1CC[C@@H](CC1)C(O)=O Chemical compound CC[C@H]1CC[C@@H](CC1)[C@H]1CC[C@@H](CC1)C(O)=O OQIHEFMTIUJJET-HDRKRICHSA-N 0.000 description 2
- 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
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MHZPFSMZADJIER-UHFFFAOYSA-N 2-cyclohexylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1CCCCC1 MHZPFSMZADJIER-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
- 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
本発明は小さな正の誘電異方性を有し、かつ低
粘性の新規な有機化合物に関する。
液晶表示素子は液晶物質が持つ光学異方性及び
誘電異方性を利用したものであるが、その表示様
式によつてTN型（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
各種の方式に分けられ、夫々の使用に適する液晶
物質の性質は異なる。しかしいずれの液晶物質も
水分、空気、熱、光等に安定であることが必要で
あることは共通しており、又、室温を中心として
出来るだけ広い温度範囲で液晶相を示すものが求
められている。しかし現在のところ単一化合物で
はこの様な条件を満たす物質はなく、数種の液晶
化合物や非液晶化合物を混合して得られる液晶組
成物を使用しているのが現状である。
本発明の目的はこの様な要求をある程度みたし
た、液晶組成物の一成分として有用な、低粘度
で、広い温度範囲で液晶相を示す新規な有機化合
物を提供することにある。
即ち、本発明は一般式
（上式中、Ｚは
The present invention relates to novel organic compounds having small positive dielectric anisotropy and low viscosity. Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and depending on the display format, there are TN type (twisted nematic type), DS type (dynamic scattering type), and guest type. There are various types such as host type and DAP type, and the properties of the liquid crystal materials suitable for each type of use are different. However, all liquid crystal materials have in common that they need to be stable against moisture, air, heat, light, etc., and they are also required to exhibit a liquid crystal phase over as wide a temperature range as possible, centered around room temperature. ing. However, at present, there is no single compound that satisfies these conditions, and the current situation is to use liquid crystal compositions obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds. It is an object of the present invention to provide a novel organic compound that satisfies these demands to some extent and is useful as a component of a liquid crystal composition, has a low viscosity, and exhibits a liquid crystal phase over a wide temperature range. That is, the present invention is based on the general formula (In the above formula, Z is
【式】【formula】
【式】【formula】
【式】【formula】
【式】又は[Formula] or
【式】を示し、Ｒは炭素数１
〜15のアルキル基又はアルコキシ基を示す）
で表わされるペンタフルオロフエノールのカルボ
ン酸エステルである。
本発明の（）式の化合物はΔεが＋１程度で、
あるものはスメクチツク液晶であり、あるものは
非液晶化合物であるが、中でもＺが
It is a carboxylic acid ester of pentafluorophenol represented by the following formula: where R represents an alkyl group or an alkoxy group having 1 to 15 carbon atoms. The compound of formula () of the present invention has a Δε of about +1,
Some are smectic liquid crystals, and some are non-liquid crystal compounds, among which Z is
トランス―４―（トランス―4′―エチルシクロ
ヘキシル）シクロヘキサンカルボン酸2.4ｇ
（0.01モル）と塩化チオニル10mlをフラスコに入
れ70℃３時間加温すると反応が進行して均一にな
る。減圧にして過剰の塩化チオニルを留去すると
油状の酸クロリドが残る。
一方、ペンタフルオロフエノール1.84ｇをピリ
ジン10mlにとかしておき、これに先の酸クロリド
を加え一晩放置する。それにトルエン100mlを加
えて溶解して水にあける。トルエン層を分液し、
6N塩酸、ついで2N苛性ソーダ溶液洗浄後水で中
性になるまで洗浄する。無水硫酸ナトリウムで乾
燥後トルエンを減圧にて留去すると結晶物が残
り、これをエタノールで再結晶すれば目的物であ
るトランス―４―（トランス―4′―エチルシクロ
ヘキシル）シクロヘキサンカルボン酸ペンタフル
オロフエニルエステルが2.3ｇ（収率57％）得ら
れた。このものはスメクチツク液晶（Sm）でＣ
―Sm点（融点）は64.5℃、Sm―Ｉ点（透明点）
は112.6℃であつた。
実施例 ２〜10
実施例１におけるトランス―４―（トランス―
4′―エチルシクロヘキシル）シクロヘキサンカル
ボン酸2.4ｇ（0.01モル）の代りに、それぞれ目
的物に対応するカルボン酸0.01モルを使用する以
外は全く同様にして第１表に示すペンタフルオロ
フエノールのカルボン酸エステルを製造した。そ
の収率、物性値等を第１表に示す。
Trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid 2.4g
(0.01 mol) and 10 ml of thionyl chloride are placed in a flask and heated at 70°C for 3 hours. The reaction progresses and becomes homogeneous. Excess thionyl chloride is distilled off under reduced pressure, leaving an oily acid chloride. On the other hand, dissolve 1.84 g of pentafluorophenol in 10 ml of pyridine, add the acid chloride mentioned above, and leave it overnight. Add 100ml of toluene to it, dissolve it, and pour it into water. Separate the toluene layer,
Wash with 6N hydrochloric acid, then 2N caustic soda solution, and then with water until neutral. After drying over anhydrous sodium sulfate, toluene is distilled off under reduced pressure to leave a crystalline substance, which is recrystallized from ethanol to obtain the target product, trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid pentafluorophore. 2.3 g (yield 57%) of enyl ester was obtained. This one is a smectic liquid crystal (Sm) and C
-Sm point (melting point) is 64.5℃, Sm-I point (clearing point)
The temperature was 112.6℃. Examples 2 to 10 Transformer-4- (trans-
Carboxylic acid esters of pentafluorophenol shown in Table 1 were prepared in exactly the same manner except that 0.01 mol of the corresponding carboxylic acid was used instead of 2.4 g (0.01 mol) of 4'-ethylcyclohexyl)cyclohexanecarboxylic acid. was manufactured. The yield, physical property values, etc. are shown in Table 1.
【表】
実施例11 （応用例）
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ネマチツク液晶温度範囲
は−３〜52℃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。Δεは＋10.5である。
上記の液晶組成物85部に本発明の実施例２の化
合物であるトランス―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
ペンタフルオロフエニルエステル7.5部及び実施
例４の化合物であるトランス―４―（トランス―
4′―ペンチルシクロヘキシル）シクロヘキサンカ
ルボン酸ペンタフルオロフエニルエステル7.5部
を加えた液晶組成物のネマチツク液晶温度範囲は
−３〜58.6℃になり、しきい電圧は1.60V、飽和
電圧は2.30Vで、粘度は20℃で25cp、Δεは＋10.0
であつた。このように本発明の化合物を加えるこ
とにより粘度をほとんど上昇させることなく、ネ
マチツク温度範囲を広げることができた。[Table] Example 11 (Application example) Trans-4-propyl-(4'-cyanophenyl)cyclohexane 28% Trans-4-pentyl-(4'-cyanophenyl)cyclohexane 42% Trans-4-heptyl-(4'- The nematic liquid crystal temperature range of a liquid crystal composition having a composition of 30% (cyanophenyl)cyclohexane is -3 to 52°C. This liquid crystal composition has a cell thickness of
When sealed in a 10 μm TN cell (twisted nematic cell), the operating threshold voltage was 1.53V and the saturation voltage was 2.12V. The viscosity was 23 cp at 20°C. Δε is +10.5. 85 parts of the above liquid crystal composition, 7.5 parts of trans-4-(trans-4'-propylcyclohexyl)cyclohexanecarboxylic acid pentafluorophenyl ester, which is the compound of Example 2 of the present invention, and trans, which is the compound of Example 4. -4- (trans-
The nematic liquid crystal temperature range of the liquid crystal composition containing 7.5 parts of 4'-pentylcyclohexyl)cyclohexanecarboxylic acid pentafluorophenyl ester is -3 to 58.6°C, the threshold voltage is 1.60V, the saturation voltage is 2.30V, Viscosity is 25cp at 20℃, Δε is +10.0
It was hot. By adding the compound of the present invention in this way, the nematic temperature range could be expanded without increasing the viscosity.
Claims (1)
ン酸エステル。 ２ 一般式 （上式中、Ｒは炭素数１〜15のアルキル基を示
す） で表わされる特許請求の範囲第１項記載のペンタ
フルオロフエノールのカルボン酸エステル誘導
体。[Claims] 1. General formula (In the above formula, Z represents [Formula] [Formula] [Formula] [Formula] [Formula] or [Formula], and R represents an alkyl group or an alkoxy group having 1 to 15 carbon atoms.) Carboxylic acid ester of phenol. 2 General formula (In the above formula, R represents an alkyl group having 1 to 15 carbon atoms.) The carboxylic acid ester derivative of pentafluorophenol according to claim 1, which is represented by the following formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6195881A JPS57176931A (en) | 1981-04-24 | 1981-04-24 | Carboxylic acid pentafluorophenol ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6195881A JPS57176931A (en) | 1981-04-24 | 1981-04-24 | Carboxylic acid pentafluorophenol ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57176931A JPS57176931A (en) | 1982-10-30 |
| JPS64384B2 true JPS64384B2 (en) | 1989-01-06 |
Family
ID=13186201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6195881A Granted JPS57176931A (en) | 1981-04-24 | 1981-04-24 | Carboxylic acid pentafluorophenol ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57176931A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2383040B (en) * | 2001-11-21 | 2006-03-01 | Merck Patent Gmbh | Multiblock compounds comprising hydrocarbon blocks & fluorocarbon, siloxane, or oligo-/poly-(oxaalkylene) block and their use in liquid crystal materials |
-
1981
- 1981-04-24 JP JP6195881A patent/JPS57176931A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57176931A (en) | 1982-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6388156A (en) | Novel 4-cyclohexylbenzoic acid compound | |
| JPS6144863B2 (en) | ||
| JPS6366825B2 (en) | ||
| JPS6325572B2 (en) | ||
| JPH0150694B2 (en) | ||
| JPS64384B2 (en) | ||
| JPS634817B2 (en) | ||
| JPH0320378B2 (en) | ||
| JPS64942B2 (en) | ||
| JPH0150693B2 (en) | ||
| JPH0518814B2 (en) | ||
| JPH0210819B2 (en) | ||
| JPH0239497B2 (en) | 44 * TORANSUU4 ** ARUKIRUSHIKUROHEKISHIRU * ANSOKUKOSAN2 * 44JIHAROGENOFUENIRUESUTERU | |
| JPH0150691B2 (en) | ||
| JPH0131499B2 (en) | ||
| JPH039895B2 (en) | ||
| JPH0247455B2 (en) | 44ARUFUA * ARUFUA * ARUFUAATORIFURUOROMECHIRUANSOKUKOSANN44 * TORANSUU4 ** ARUKIRUSHIKUROHEKISHIRU * FUENIRUESUTERU | |
| JPH0210820B2 (en) | ||
| JPH037653B2 (en) | ||
| JPH0229055B2 (en) | JISHIKUROHEKISHIRUBENZENJUDOTAI | |
| JPS6353179B2 (en) | ||
| JPS58121247A (en) | 3-chloro-4-halogenophenyl trans-4-(4'-substituted phenyl) cyclohexanecarboxylate | |
| JPH0528217B2 (en) | ||
| JPS64386B2 (en) | ||
| JPH0247979B2 (en) | FURUOROBIFUENIRUNOESUTERUJUDOTAI |