JPH0216737B2 - - Google Patents
Info
- Publication number
- JPH0216737B2 JPH0216737B2 JP16910082A JP16910082A JPH0216737B2 JP H0216737 B2 JPH0216737 B2 JP H0216737B2 JP 16910082 A JP16910082 A JP 16910082A JP 16910082 A JP16910082 A JP 16910082A JP H0216737 B2 JPH0216737 B2 JP H0216737B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- difluoro
- type
- added
- heptane
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims description 17
- -1 3,4-difluoro-4'-substituted biphenyl Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YMQPKONILWWJQG-UHFFFAOYSA-N 4-bromo-1,2-difluorobenzene Chemical compound FC1=CC=C(Br)C=C1F YMQPKONILWWJQG-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 238000001816 cooling Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XRPVQXPWEVJKTN-UHFFFAOYSA-N 1-hexyl-4-phenylbenzene Chemical group C1=CC(CCCCCC)=CC=C1C1=CC=CC=C1 XRPVQXPWEVJKTN-UHFFFAOYSA-N 0.000 description 1
- PKOWPSHVZJGPOJ-UHFFFAOYSA-N 4-octylcyclohexan-1-one Chemical compound CCCCCCCCC1CCC(=O)CC1 PKOWPSHVZJGPOJ-UHFFFAOYSA-N 0.000 description 1
- UISZWYORHKBZTP-UHFFFAOYSA-N 7-methoxy-n,n-dimethyl-1h-indazole-3-carboxamide Chemical compound COC1=CC=CC2=C1NN=C2C(=O)N(C)C UISZWYORHKBZTP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】
本発明は正の誘電異方性を示す新規な液晶物質
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel liquid crystal materials exhibiting positive dielectric anisotropy.
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、数値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。 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 materials used exhibit a liquid crystal phase over a wide temperature range, and also contain moisture 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 situation is to obtain compounds that can be put to practical use by mixing numerical liquid crystal compounds and non-liquid crystal compounds.
最近低温（−20℃位）から高温（80℃位）まで
動作するような液晶組成物が求められてきてい
る。特に低温側における粘度の低いものについて
の要求が大きい。 Recently, there has been a demand for liquid crystal compositions that can operate from low temperatures (approximately -20°C) to high temperatures (approximately 80°C). In particular, there is a strong demand for products with low viscosity at low temperatures.
本発明の化合物は、特に低温度における液晶表
示の改善のために有効に用いることができるもの
である。 The compound of the present invention can be effectively used for improving liquid crystal display, especially at low temperatures.
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又
はアルコキシ基を示す）
で表わされる３，４−ジフルオロ−4′−置換ビフ
エニルである。 That is, the present invention is based on the general formula (In the above formula, R represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms.) It is a 3,4-difluoro-4'-substituted biphenyl represented by:
本発明の化合物の一つである３，４−ジフルオ
ロ−4′−オクチルビフエニルはm.p.25.1〜26.1℃
Ｎ−Ｉ点−19.5℃のモノトロピツク液晶化合物で
あり、低粘性なため液晶組成物の一成分として使
用することにより、ネマチツク液晶温度範囲を低
温側に拡げかつ低粘性な液晶組成物を得ることが
できる。 3,4-difluoro-4'-octylbiphenyl, one of the compounds of the present invention, has a mp of 25.1 to 26.1℃.
It is a monotropic liquid crystal compound with an N-I point of -19.5°C and has low viscosity, so by using it as a component of a liquid crystal composition, it is possible to expand the nematic liquid crystal temperature range to the lower temperature side and obtain a liquid crystal composition with low viscosity. can.
つぎに本発明の製造法について述べる。 Next, the manufacturing method of the present invention will be described.
まず３，４−ジフルオロブロモベンゼンを金属
マグネシウムと反応させ３，４−ジフルオロフエ
ニルマグネシウムブロミドとし、これを４−置換
シクロヘキサンと反応させて３，４−ジフルオロ
ー（4′−置換シクロヘキサン−1′−オール）ベン
ゼンとする。次にこれを硫酸水素カリウムで脱水
して３，４−ジフルオロ−（4′−置換シクロヘキ
セン−1′−イル）ベンゼンとする。これをクロラ
ニルで脱水素して３，４−ジフルオロ−4′置換ビ
フエニルを得る。 First, 3,4-difluorobromobenzene is reacted with metallic magnesium to form 3,4-difluorophenylmagnesium bromide, which is then reacted with 4-substituted cyclohexane to produce 3,4-difluoro(4'-substituted cyclohexane-1'- All) benzene. This is then dehydrated with potassium hydrogen sulfate to give 3,4-difluoro-(4'-substituted cyclohexen-1'-yl)benzene. This is dehydrogenated with chloranil to obtain 3,4-difluoro-4'-substituted biphenyl.
以上を化学式で示すと、次のようになる。 The chemical formula for the above is as follows.
以下、実施例により本発明の化合物の製造法及
び使用例について詳細に説明する。 Hereinafter, the manufacturing method and usage examples of the compound of the present invention will be explained in detail with reference to Examples.
実施例 １
〔３，４−ジフルオロ−4′−オクチルビフエニ
ルの製造〕
削り状マグネシウム1.2ｇ（0.049モル）を３つ
口フラスコに入れ、３，４−ジフルオロブロモベ
ンゼン9.5ｇ（0.049モル）をテトラヒドロフラン
に溶かした液25mlを、N2気流中反応温度を35℃
程に保ちながらゆつくりと滴下していくと反応し
て３時間でマグネシウムは溶けて均一になり３，
４−ジフルオロフエニルマグネシウムプロミドを
生じる。これに４−オクチルシクロヘキサノン
8.2ｇ（0.039モル）をテトラヒドロフランに溶か
して50mlとしたものを、反応温度を20℃以下に保
ちつつ速かに滴下する。滴下後１時間還流させつ
いで3N−塩酸100mlを加える。反応液をｎ−ヘプ
タン100mlで３回抽出し、合わせた油槽を洗液が
中性になるまで水洗し、ｎ−ヘプタンを減圧留去
する。残留した油状物は３，４−ジフルオロ−
（４−オクチルシクロヘキシル−1′−オール）ベ
ンゼンであり、これに硫酸水素カリウム４ｇを加
え、N2気流中160℃で２時間脱水する。冷却後ｎ
−ヘプタン200mlを加え硫酸水素カリウムを別
し、ヘプタン層を洗液が中性になるまで水洗し、
溶媒を減圧留去する。残留物をｎ−ヘプタンとエ
タノールの混合溶媒から再結晶して得られたのが
３，４−ジフルオロ（4′−オクチルシクロヘキセ
ン−1′−イル）ベンゼンであり、このもの4.0ｇ
（0.013モル）をキシレン100mlに溶かしクロラニ
ル6.5ｇ（0.026モル）を加え20時間還流する。冷
却後トルエン50mlを加えアルカリ洗浄を行ない水
洗を施こした後、溶媒を留去する。ｎ−ヘプタン
で再結晶を行ない、目的の３，４−ジフルオロー
4′−オクチルビフエニルを得た。収量0.5ｇ。Example 1 [Production of 3,4-difluoro-4'-octylbiphenyl] 1.2 g (0.049 mol) of magnesium turnings was placed in a three-necked flask, and 9.5 g (0.049 mol) of 3,4-difluorobromobenzene was added. 25ml of the solution dissolved in tetrahydrofuran was heated to a reaction temperature of 35°C in a N2 stream.
If you drop it slowly while keeping it at a moderate temperature, it will react and the magnesium will dissolve and become homogeneous in 3 hours.
This yields 4-difluorophenylmagnesium bromide. In this, 4-octylcyclohexanone
8.2 g (0.039 mol) was dissolved in tetrahydrofuran to make 50 ml, and the solution was quickly added dropwise while keeping the reaction temperature below 20°C. After the dropwise addition, the mixture was refluxed for 1 hour, and then 100 ml of 3N hydrochloric acid was added. The reaction solution was extracted three times with 100 ml of n-heptane, the combined oil bath was washed with water until the washing solution became neutral, and the n-heptane was distilled off under reduced pressure. The remaining oil is 3,4-difluoro-
(4-octylcyclohexyl-1'-ol)benzene, to which 4 g of potassium hydrogen sulfate was added and dehydrated at 160° C. for 2 hours in a N 2 stream. After cooling n
- Add 200ml of heptane, separate the potassium hydrogen sulfate, wash the heptane layer with water until the washing solution becomes neutral,
The solvent is removed under reduced pressure. The residue was recrystallized from a mixed solvent of n-heptane and ethanol, and 4.0 g of 3,4-difluoro(4'-octylcyclohexen-1'-yl)benzene was obtained.
(0.013 mol) was dissolved in 100 ml of xylene, 6.5 g (0.026 mol) of chloranil was added, and the mixture was refluxed for 20 hours. After cooling, 50 ml of toluene was added to perform alkaline washing, followed by water washing, and then the solvent was distilled off. Recrystallize with n-heptane to obtain the desired 3,4-difluoro
4'-octylbiphenyl was obtained. Yield 0.5g.
その融点は25.1〜26.1℃、Ｎ−Ｉ点は−19.5℃
であつた。 Its melting point is 25.1-26.1℃, N-I point is -19.5℃
It was hot.
実施例 ２、３ 実施例１と同様の方法で次の化合物を得た。Examples 2 and 3 The following compound was obtained in the same manner as in Example 1.
３，４−ジフルオロ−4′−ヘキシルビフエニル
m.p. 2.0〜2.8℃
３，４−ジフルオロ−4′−ペンチルオキシビフエ
ニル
m.p. 16.0〜22.6℃
実施例 ４（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％
トランス−４−ペンチル−（4″−ジアノビフエニ
ル）シクロヘキサン 15％
なる液晶組成物のネマチツク温度範囲は−10〜
72.1℃であり、20℃における粘度は28cp、透明電
極を施した厚さ10μｍのTNセルに封入したしき
い値電圧は1.7V飽和電圧は2.1Vであつた。3,4-difluoro-4'-hexylbiphenyl mp 2.0-2.8℃ 3,4-difluoro-4'-pentyloxybiphenyl mp 16.0-22.6℃ Example 4 (Usage example) Trans-4-propyl-(4 ′-cyanophenyl)
Cyclohexane 24% trans-4-pentyl-(4'-cyanophenyl)
Cyclohexane 36% trans-4-heptyl-(4'-cyanophenyl)
The nematic temperature range of a liquid crystal composition consisting of 25% cyclohexane and 15% trans-4-pentyl-(4″-dianobiphenyl)cyclohexane is from −10 to
The temperature was 72.1°C, the viscosity at 20°C was 28 cp, the threshold voltage was 1.7V, and the saturation voltage was 2.1V when sealed in a 10 μm thick TN cell with a transparent electrode.
このもの90部に本発明の３，４−ジフルオロー
4′−ヘキシルビフエニル10部を加えた液晶組成物
のネマチツク透明点は57.1℃と低下したものの20
℃における粘度を27cpに低減でき、上記セルに
封入したしきい値電圧は1.46V、飽和電圧は
2.00Vと駆動電圧をおさえることができた。 3,4-difluoro of the present invention is added to 90 parts of this product.
Although the nematic clearing point of the liquid crystal composition containing 10 parts of 4'-hexylbiphenyl decreased to 57.1°C, it remained at 20°C.
The viscosity at °C can be reduced to 27cp, the threshold voltage sealed in the above cell is 1.46V, and the saturation voltage is
I was able to keep the drive voltage down to 2.00V.
Claims (1)
はアルコキシ基を示す）で表わされる３，４−ジ
フルオロ−4′−置換ビフエニル。 ２ 一般技 （上式中Ｒは炭素数１〜15を有するアルキル基又
はアルコキシ基を示す）で表わされる３，４−ジ
フルオロ−4′−置換ビフエニルを少なくとも一種
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 represents an alkyl group or an alkoxy group having 1 to 15 carbon atoms.) 3,4-difluoro-4'-substituted biphenyl. 2 General skills (In the above formula, R represents an alkyl group or an alkoxy group having 1 to 15 carbon atoms.) A liquid crystal composition containing at least one type of 3,4-difluoro-4'-substituted biphenyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16910082A JPS5959636A (en) | 1982-09-28 | 1982-09-28 | 3,4-difluoro-4'-substituted biphenyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16910082A JPS5959636A (en) | 1982-09-28 | 1982-09-28 | 3,4-difluoro-4'-substituted biphenyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5959636A JPS5959636A (en) | 1984-04-05 |
| JPH0216737B2 true JPH0216737B2 (en) | 1990-04-18 |
Family
ID=15880305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16910082A Granted JPS5959636A (en) | 1982-09-28 | 1982-09-28 | 3,4-difluoro-4'-substituted biphenyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5959636A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61207347A (en) * | 1985-03-12 | 1986-09-13 | Chisso Corp | Cyclohexane derivative |
| JPH07100790B2 (en) * | 1986-09-01 | 1995-11-01 | チッソ株式会社 | Nematic liquid crystal composition |
-
1982
- 1982-09-28 JP JP16910082A patent/JPS5959636A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5959636A (en) | 1984-04-05 |
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