JPS64936B2 - - Google Patents
Info
- Publication number
- JPS64936B2 JPS64936B2 JP1933781A JP1933781A JPS64936B2 JP S64936 B2 JPS64936 B2 JP S64936B2 JP 1933781 A JP1933781 A JP 1933781A JP 1933781 A JP1933781 A JP 1933781A JP S64936 B2 JPS64936 B2 JP S64936B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- present
- compounds
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QSJNKJGPJVOGPK-UHFFFAOYSA-N 4-(4-fluorophenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(F)C=C1 QSJNKJGPJVOGPK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-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
- -1 alkyl bromide ethyl ether Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000010992 reflux Methods 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
本発明は液晶組成物の成分として有用な新規な
有機化合物に関し、更に詳しくは液晶化合物との
相溶性がよく、かつ減粘効果を有する化合物に関
する。
液晶表示素子は液晶物質が有する光学異方性及
び誘電異方性を利用したものであるが、その表示
方式にはTN型，DS型，ゲスト・ホスト型，
DAP型，ホワイト・テイラー型など各種の方式
があり、それぞれの方式により使用される液晶物
質に要求される性質も異る。例えば表示素子の種
類によつて、液晶物質として誘電異方性△εが正
のものを必要としたり、負のものを必要とした
り、或はその中間的な値のものが適したりする。
しかしいずれにしても使用される液晶物質はでき
るだけ広い温度範囲で液晶相を示し、又水分，
熱，空気，光などに対して安定である必要があ
る。現在のところ単一化合物でこの様な条件をす
べて満たすものはなく、数種の液晶化合物や非液
晶化合物を混合して一応実用に耐えるものを得て
いるのが現状である。
一般に任意の△ε値を持つ液晶化合物は△ε値
が正のものと負のものを適宜混合することによつ
て得られるが、その場合△ε値の絶対値の大きな
もの同志では混合しにくく結晶が出易いので、△
ε値の絶対値の小さな化合物、しかも低粘度で相
溶性がよい化合物が実用的な液晶組成物を構成す
る成分として望まれている。
本発明の化合物はそれ自体は非液晶化合物であ
るが、液晶組成物の構成成分として使用して上記
の様な要望をある程度みたす化合物である。
即ち、本発明は一般式
（上式中Ｒは炭素数１〜10を有するアルキル基
を示す）
で表わされる４―（β―アルコキシエトキシ）―
4′―フルオロビフエニルである。
本発明の化合物は液晶相は示さないが誘電異方
性値は＋２程度と小さいにもかかわらず、液晶組
物に加えることにより、その粘度をある程度低下
させ、その上しきい値電圧をも降下させる効果が
ある。
つぎに本発明の化合物の製造方法について述べ
ると４―フルオロ―4′―ヒドロキシビフエニルと
アルキル臭化エチルエーテルをエチレングリコー
ルモノメチルエーテル中で水酸化ナトリウムと共
に反応して製造できる。化学式で示すと
以下実施例（製造例及び応用例）により本発明
の化合物について更に詳細に説明する。
実施例 １〜４
〔４―（β―アルコキシエトキシ）―4′―フル
オロビフエニル（（）式でＲがCH3，C2H5，
C3H7，C4H9のもの）の製造〕
４―フルオロ―4′―ヒドロキシビフエニル2.0
ｇ（0.0106モル）をエチレングリコールモノメチ
ルエーテル30mlに溶解し、これに2N水酸化ナト
リウム水溶液６mlを加えて振りまぜ均一液を得
る。次にアルキル臭化エチルエーテルを0.016モ
ル加えて３時間マントルヒーターで加熱還流す
る。反応後、室温まで冷却し、50mlの水にあけ、
トルエン150mlで抽出する。トルエン層を6N塩酸
で、ついに2N水酸化ナトリウム水溶液で洗浄し
た後更に中性になるまで水洗してから無水硫酸ナ
トリウムで乾燥後減圧にしてトルエンを留去す
る。残つた油状物をエタノールで再結晶すると目
的物である４―（β―アルコキシエトキシ）―
4′―フルオロビフエニルが得られる。その収率及
び物性値を第１表に示す。
The present invention relates to a novel organic compound useful as a component of a liquid crystal composition, and more particularly to a compound that has good compatibility with a liquid crystal compound and has a viscosity-reducing effect. Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and their display methods include TN type, DS type, guest-host type,
There are various types such as DAP type and White-Taylor type, and each type requires different properties of the liquid crystal material used. For example, depending on the type of display element, a liquid crystal material with a positive dielectric anisotropy Δε may be required, a material with a negative dielectric anisotropy may be required, or a material with an intermediate value may be suitable.
However, in any case, the liquid crystal material used exhibits a liquid crystal phase over a wide temperature range, and
It must be stable against heat, air, light, etc. At present, there is no single compound that satisfies all of these conditions, and the current state of affairs is to mix several types of liquid crystal compounds and non-liquid crystal compounds to obtain compounds that can withstand practical use. In general, liquid crystal compounds with arbitrary △ε values can be obtained by appropriately mixing those with positive △ε values and those with negative Δε values, but in this case, it is difficult to mix compounds with large absolute values of △ε values. Because crystals tend to come out, △
A compound having a small absolute value of ε value, low viscosity, and good compatibility is desired as a component constituting a practical liquid crystal composition. Although the compound of the present invention is itself a non-liquid crystal compound, it is a compound that satisfies the above-mentioned demands to some extent when used as a constituent component of a liquid crystal composition. That is, the present invention is based on the general formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) 4-(β-alkoxyethoxy)-
4'-Fluorobiphenyl. Although the compound of the present invention does not exhibit a liquid crystal phase but has a small dielectric anisotropy value of about +2, by adding it to a liquid crystal composite, it can reduce its viscosity to a certain extent and also lower its threshold voltage. It has the effect of Next, the method for producing the compound of the present invention will be described. It can be produced by reacting 4-fluoro-4'-hydroxybiphenyl and alkyl bromide ethyl ether with sodium hydroxide in ethylene glycol monomethyl ether. Shown as a chemical formula The compounds of the present invention will be explained in more detail below using Examples (manufacturing examples and application examples). Examples 1 to 4 [4-(β-alkoxyethoxy)-4′-fluorobiphenyl (in the formula (), R is CH 3 , C 2 H 5 ,
Production of C 3 H 7 , C 4 H 9 ) 4-fluoro-4'-hydroxybiphenyl 2.0
Dissolve g (0.0106 mol) in 30 ml of ethylene glycol monomethyl ether, add 6 ml of 2N aqueous sodium hydroxide solution, and shake to obtain a homogeneous solution. Next, 0.016 mol of alkyl bromide ethyl ether was added, and the mixture was heated under reflux using a mantle heater for 3 hours. After the reaction, cool to room temperature, pour into 50ml of water,
Extract with 150ml of toluene. The toluene layer is washed with 6N hydrochloric acid and finally with 2N aqueous sodium hydroxide solution, further washed with water until neutral, dried over anhydrous sodium sulfate, and then the toluene is distilled off under reduced pressure. When the remaining oil is recrystallized with ethanol, the target product 4-(β-alkoxyethoxy)-
4′-fluorobiphenyl is obtained. The yield and physical property values are shown in Table 1.
【表】
尚、以上の各化合物について赤外線吸収スペク
トル及びNMRスペクトルを測定してその構造を
確認した。
実施例５ （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 25部
トランス―４―ペンチル―（4′―シアノフエニ
ル）シクロヘキサン 35部
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部
トランス―４―ペンチル―（4″―シアノビフエ
ニル）シクロヘキサン 15部
からなる液晶組成物Ａのネマチツク温度―６〜＋
70℃，20℃での粘度は28cp，△εは＋10.1，しき
い値電圧は1.65V，飽和電圧は2.25Vである。こ
の液晶組成物85部に対し本発明の化合物である４
―（β―ブトキシエトキシ）―4′―フルオロビフ
エニル15部を加えて得られる液晶組成物のネマチ
ツク温度範囲は−10〜＋54.5℃，20℃の粘度は
26.5cp，△εは9.9，しきい値電圧は1.40V，飽和
電圧は1.95Vとなり、本発明の化合物を添加する
ことにより液晶組成物の粘度及びしきい値電圧，
飽和電圧を下げることができた。[Table] Infrared absorption spectra and NMR spectra of each of the above compounds were measured to confirm their structures. Example 5 (Application example) Trans-4-propyl-(4'-cyanophenyl)cyclohexane 25 parts trans-4-pentyl-(4'-cyanophenyl)cyclohexane 35 parts trans-4-heptyl-(4'-cyanophenyl)cyclohexane Nematic temperature of liquid crystal composition A consisting of 25 parts trans-4-pentyl-(4″-cyanobiphenyl)cyclohexane 15 parts −6 to +
The viscosity at 70℃ and 20℃ is 28cp, △ε is +10.1, threshold voltage is 1.65V, and saturation voltage is 2.25V. 4 parts of the compound of the present invention for 85 parts of this liquid crystal composition.
The nematic temperature range of the liquid crystal composition obtained by adding 15 parts of -(β-butoxyethoxy)-4'-fluorobiphenyl is -10 to +54.5℃, and the viscosity at 20℃ is
26.5 cp, △ε is 9.9, threshold voltage is 1.40 V, and saturation voltage is 1.95 V. By adding the compound of the present invention, the viscosity and threshold voltage of the liquid crystal composition,
We were able to lower the saturation voltage.
Claims (1)
を示す） で表わされる４―（β―アルコキシエトキシ）―
4′―フルオロビフエニル。[Claims] 1. General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) 4-(β-alkoxyethoxy)-
4′-Fluorobiphenyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1933781A JPS57134431A (en) | 1981-02-12 | 1981-02-12 | 4-(beta-alkoxyethoxy)-4'-fluorobiphenyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1933781A JPS57134431A (en) | 1981-02-12 | 1981-02-12 | 4-(beta-alkoxyethoxy)-4'-fluorobiphenyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57134431A JPS57134431A (en) | 1982-08-19 |
| JPS64936B2 true JPS64936B2 (en) | 1989-01-10 |
Family
ID=11996582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1933781A Granted JPS57134431A (en) | 1981-02-12 | 1981-02-12 | 4-(beta-alkoxyethoxy)-4'-fluorobiphenyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57134431A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0333634U (en) * | 1989-08-11 | 1991-04-03 | ||
| JPH0614500U (en) * | 1992-02-07 | 1994-02-25 | 栄次郎 三賀 | Ejector for bathtub |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109575948B (en) * | 2017-09-28 | 2022-06-17 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN109575945B (en) * | 2017-09-28 | 2022-06-17 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
-
1981
- 1981-02-12 JP JP1933781A patent/JPS57134431A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0333634U (en) * | 1989-08-11 | 1991-04-03 | ||
| JPH0614500U (en) * | 1992-02-07 | 1994-02-25 | 栄次郎 三賀 | Ejector for bathtub |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57134431A (en) | 1982-08-19 |
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