JPH0244291B2 - 3 * 44JIKUROROOBISHIKUROHEKISHIRUBENZENJUDOTAI - Google Patents
3 * 44JIKUROROOBISHIKUROHEKISHIRUBENZENJUDOTAIInfo
- Publication number
- JPH0244291B2 JPH0244291B2 JP15613582A JP15613582A JPH0244291B2 JP H0244291 B2 JPH0244291 B2 JP H0244291B2 JP 15613582 A JP15613582 A JP 15613582A JP 15613582 A JP15613582 A JP 15613582A JP H0244291 B2 JPH0244291 B2 JP H0244291B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- liquid crystal
- benzene
- dichloro
- cyclohexyl
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 239000004973 liquid crystal related substance Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 4
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 4
- -1 3, 4-dichloro-1-[trans-4'-(trans- 4′′-pentylcyclohexyl)cyclohexyl] Benzene Chemical compound 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OZLFNAZSDVXEFU-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)cyclohexan-1-one Chemical compound C1CC(CCCCC)CCC1C1CCC(=O)CC1 OZLFNAZSDVXEFU-UHFFFAOYSA-N 0.000 description 1
- CFPZDVAZISWERM-UHFFFAOYSA-N 4-bromo-1,2-dichlorobenzene Chemical compound ClC1=CC=C(Br)C=C1Cl CFPZDVAZISWERM-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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- RMXGWLUCCKWPGK-UHFFFAOYSA-M magnesium;1,2-dichlorobenzene-5-ide;bromide Chemical compound [Mg+2].[Br-].ClC1=CC=[C-]C=C1Cl RMXGWLUCCKWPGK-UHFFFAOYSA-M 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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】
本発明の化合物は正の誘電異方性を示す新規な
液晶物質及びそれを含有する液晶組成物に関す
る。DETAILED DESCRIPTION OF THE INVENTION The compounds of the present invention relate to novel liquid crystal substances exhibiting positive dielectric anisotropy and liquid crystal compositions containing the same.
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があ
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。特に最近は−
20〜80℃という様な広い温度範囲で作動する液晶
表示素子が要求される様になつて来た。この様な
要求を満足させるためには粘度、特に低温での粘
度を低くすることが有力な手段である。しかし一
般的には透明点（Ｎ−Ｉ点）の高いものは粘度が
高く、粘度が低いもの、例えばアルキルフエニル
シクロヘキサン誘導体などは透明点が低い。本発
明の目的は、この様な要求にこたえる高いＮ−Ｉ
点をもち、しかも粘度の低い液晶化合物を提供す
ることにある。 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. Especially recently-
There has been a growing demand for liquid crystal display elements that operate over a wide temperature range of 20 to 80 degrees Celsius. In order to satisfy such requirements, an effective means is to lower the viscosity, especially the viscosity at low temperatures. However, in general, those with a high clearing point (NI point) have a high viscosity, and those with a low viscosity, such as alkylphenylcyclohexane derivatives, have a low clearing point. The purpose of the present invention is to provide a high N-I that meets such requirements.
An object of the present invention is to provide a liquid crystal compound having a dot and a low viscosity.
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３，４−ジクロロ−１−〔トランス
−4′−（トランス−４−アルキルシクロヘキシ
ル）シクロヘキシル〕ベンゼンである。 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.) 3,4-dichloro-1-[trans-4'-(trans-4-alkylcyclohexyl)cyclohexyl]benzene.
本発明の（）式の化合物は広い温度範囲で液
晶相を示し、かつ低粘性なので上記の要求をみた
すべく有効に用いることができる。例えば、３，
４−ジクロロ−１−〔トランス−4′−（トランス−
4″−ペンチルシクロヘキシル）シクロヘキシル〕
ベンゼンは、結晶−ネマチツク点50.4℃、ネマチ
ツク−透明点103.4℃と広いネマチツク液晶相を
示し、広い液晶温度範囲をもつ低粘性な液晶組成
物を構成する一成分として使用される。 The compound of formula () of the present invention exhibits a liquid crystal phase over a wide temperature range and has low viscosity, so it can be effectively used to meet the above requirements. For example, 3,
4-dichloro-1-[trans-4'-(trans-
4″-pentylcyclohexyl)cyclohexyl]
Benzene exhibits a wide nematic liquid crystal phase with a crystal-nematic point of 50.4°C and a nematic-clearing point of 103.4°C, and is used as a component of a low-viscosity liquid crystal composition having a wide liquid crystal temperature range.
つぎに本発明の化合物の製造法について述べ
る。まず１−ブロモ−３，４−ジクロロベンゼン
と金属マグネシウムを反応させてグリニヤール試
薬とし、これと４−（トランス−4′−アルキルシ
クロヘキシル）シクロヘキサノンと反応させて
３，４−ジクロロ−１−〔4′−（トランス−4″−ア
ルキルシクロヘキシル）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−ジクロロ−１−〔4′−（ト
ランス−4″−アルキルシクロヘキシル）シクロヘ
キセン−1′−イル〕ベンゼンを得る。これをトル
エンに溶かしラネーニツケル存在下、接触還元を
行ない目的の３，４−ジクロロ−１−〔トランス
−4′−（トランス−4″−アルキルシクロヘキシル）
シクロヘキシル〕ベンゼンを得る。 Next, a method for producing the compound of the present invention will be described. First, 1-bromo-3,4-dichlorobenzene and metallic magnesium are reacted to obtain a Grignard reagent, which is then reacted with 4-(trans-4'-alkylcyclohexyl)cyclohexanone to produce 3,4-dichloro-1-[4 '-(trans-4''-alkylcyclohexyl)cyclohexane-1'-ol]benzene. Next, this is dehydrated with potassium hydrogen sulfate to give 3,4-dichloro-1-[4'-(trans-4'') -alkylcyclohexyl)cyclohexen-1'-yl]benzene is obtained. This was dissolved in toluene and subjected to catalytic reduction in the presence of Raneynickel to obtain the desired 3,4-dichloro-1-[trans-4'-(trans-4''-alkylcyclohexyl).
cyclohexyl]benzene is obtained.
以上を化学式で示すと次のようになる。 The above is expressed as a chemical formula as follows.
以下実施例により本発明の化合物について更に
詳細に説明する。 The compounds of the present invention will be explained in more detail with reference to Examples below.
実施例 １
〔３，４−ジクロロ−１−〔トランス−4′−（ト
ランス−4″−ペンチルシクロヘキシル）シクロ
ヘキシル〕ベンゼンの製造〕
マグネシウム切片1.2ｇ（0.049モル）を３つ口
フラスコに入れ、３，４−ジクロロブロモベンゼ
ン11.1ｇ（0.049モル）をテトラヒドロフランに
溶かした溶液30mlを、N2気流中で反応温度を30
〜35℃に保ち、撹拌しながらゆつくり滴下して行
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−ジクロロフエニルマグネシウムブ
ロミドを生ずる。これに４−（トランス−4′−ペ
ンチルシクロヘキシル）シクロヘキサノンの10.0
ｇ（0.040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５〜10℃に保ち
つつなるべく速やかに滴下する。滴下後、35℃ま
で昇温し30分間撹拌し、ついで3N塩酸50mlを加
える。反応液を分液漏斗にとり200mlのトルエン
で３回抽出後、合わせたトルエン層を水で洗液が
中性になるまで洗浄してからトルエンを減圧留去
する。残留した油状物は３，４−ジクロロ−１−
〔4′−（トランス−4″−ペンチルシクロヘキシル）
シクロヘキセン−1′−オール〕ベンゼンである。
これに硫酸水素カリウム６ｇを加えN2気流中160
℃で２時間脱水する。冷却後200mlのトルエンを
加えてから硫酸水素カリウムを別し、トルエン
層を洗液が中性になるまで水洗する。次いでトル
エンを減圧留去し、残る油状物をアセトンで再結
晶して得られるのが３，４−ジクロロ−１−
〔4′−（トランス−4″−ペンチルシクロヘキシル）
シクロヘキセン−1′−イル〕ベンゼンである。こ
のもの1.8ｇをトルエン200mlに溶かしラネーニツ
ケル触媒1.0ｇを加え、常温常圧で接触還元を行
なつた。反応をガスクロマトグラフイーで追跡
し、原料が消失した時点で終了した。触媒を別
後、溶媒を減圧留去し、残留物をトルエンで再結
晶をくり返し目的の３，４−ジクロロ−１−〔ト
ランス−4′−（トランス−4″−ペンチルシクロヘ
キシル）シクロヘキシル〕ベンゼンを得た。収量
0.1ｇ。Ｃ−Ｎ点は50.4℃、Ｎ−Ｉ点は103.4℃で
あつた。Example 1 [Production of 3,4-dichloro-1-[trans-4′-(trans-4″-pentylcyclohexyl)cyclohexyl]benzene] 1.2 g (0.049 mol) of magnesium pieces were placed in a three-necked flask, and , 30 ml of a solution of 11.1 g (0.049 mol) of 4-dichlorobromobenzene dissolved in tetrahydrofuran was heated to a reaction temperature of 30 ml in a N 2 atmosphere.
When kept at ~35°C and slowly added dropwise while stirring, the reaction occurs, and in 3 hours the magnesium dissolves and becomes homogeneous to produce 3,4-dichlorophenylmagnesium bromide. This was followed by 10.0% of 4-(trans-4'-pentylcyclohexyl)cyclohexanone.
g (0.040 mol) dissolved in tetrahydrofuran to make 50 ml was added dropwise as quickly as possible while maintaining the reaction temperature at 5 to 10°C. After dropping, the temperature was raised to 35°C, stirred for 30 minutes, and then 50 ml of 3N hydrochloric acid was added. The reaction solution is placed in a separatory funnel and extracted three times with 200 ml of toluene. The combined toluene layers are washed with water until the washings become neutral, and the toluene is distilled off under reduced pressure. The remaining oil is 3,4-dichloro-1-
[4′-(trans-4″-pentylcyclohexyl)
cyclohexene-1'-ol]benzene.
Add 6 g of potassium hydrogen sulfate to this and add 160 g of potassium hydrogen sulfate in a N2 gas stream.
Dehydrate at ℃ for 2 hours. After cooling, add 200 ml of toluene, separate the potassium hydrogen sulfate, and wash the toluene layer with water until the washing liquid becomes neutral. Next, toluene was distilled off under reduced pressure, and the remaining oil was recrystallized from acetone to obtain 3,4-dichloro-1-
[4′-(trans-4″-pentylcyclohexyl)
cyclohexen-1'-yl]benzene. 1.8 g of this product was dissolved in 200 ml of toluene, 1.0 g of Raney nickel catalyst was added, and catalytic reduction was carried out at room temperature and pressure. The reaction was followed by gas chromatography and was terminated when the raw materials disappeared. After separating the catalyst, the solvent was distilled off under reduced pressure, and the residue was repeatedly recrystallized from toluene to obtain the desired 3,4-dichloro-1-[trans-4′-(trans-4″-pentylcyclohexyl)cyclohexyl]benzene. Obtained.Yield
0.1g. The C-N point was 50.4°C, and the N-I point was 103.4°C.
他の置換基のものについても実施例１と同様の
方法で製造できる。 Those with other substituents can also be produced in the same manner as in Example 1.
実施例 ２
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％
なる液晶組成物のネマチツク温度範囲は−３℃〜
52℃である。△εは＋11.8、しきい電圧は．5V、
飽和電圧は2.0V、20℃での粘度は23cpである。Example 2 Trans-4-propyl-(4'-cyanophenyl)
Cyclohexane 28% trans-4-pentyl-(4'-cyanophenyl)
Cyclohexane 42% trans-4-heptyl-(4'-cyanophenyl)
The nematic temperature range of a liquid crystal composition made of 30% cyclohexane is -3℃~
It is 52℃. △ε is +11.8, threshold voltage is. 5V,
The saturation voltage is 2.0V and the viscosity at 20°C is 23cp.
この液晶組成物90部に本発明の実施例１で示し
た、３，４−ジクロロ−１−〔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
キシル〕ベンゼン10部を加えた液晶組成物のネマ
チツク液晶温度範囲は−３〜55.1℃に広がり粘度
は20℃で27cp、△εは10.6、しきい電圧は1.5V、
飽和電圧は2.0Vであつた。粘度をあまり上げず
にネマチツク温度範囲を広げることができ、駆動
電圧も高くなつていない。 A liquid crystal composition in which 10 parts of 3,4-dichloro-1-[trans-4'-(trans-4''-pentylcyclohexyl)cyclohexyl]benzene shown in Example 1 of the present invention was added to 90 parts of this liquid crystal composition. The nematic liquid crystal temperature range of the material is -3~55.1℃, the viscosity is 27cp at 20℃, △ε is 10.6, the threshold voltage is 1.5V,
The saturation voltage was 2.0V. The nematic temperature range can be expanded without significantly increasing the viscosity, and the driving voltage does not increase.
Claims (1)
示す） で表わされる３，４−シクロロ−１−〔トランス
−4′−（トランス−4″−アルキルシクロヘキシル）
シクロヘキシル〕ベンゼン。 ２ 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３，４−ジクロロ−１−〔トランス
−4′−（トランス−4″−アルキルシクロヘキシル）
シクロヘキシル〕ベンゼン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 having 1 to 10 carbon atoms) 3,4-cyclo-1-[trans-4'-(trans-4''-alkylcyclohexyl)
cyclohexyl]benzene. 2 General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) 3,4-dichloro-1-[trans-4'-(trans-4''-alkylcyclohexyl)
A liquid crystal composition containing at least one type of benzene (cyclohexyl).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15613582A JPH0244291B2 (en) | 1982-09-08 | 1982-09-08 | 3 * 44JIKUROROOBISHIKUROHEKISHIRUBENZENJUDOTAI |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15613582A JPH0244291B2 (en) | 1982-09-08 | 1982-09-08 | 3 * 44JIKUROROOBISHIKUROHEKISHIRUBENZENJUDOTAI |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5944332A JPS5944332A (en) | 1984-03-12 |
| JPH0244291B2 true JPH0244291B2 (en) | 1990-10-03 |
Family
ID=15621083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15613582A Expired - Lifetime JPH0244291B2 (en) | 1982-09-08 | 1982-09-08 | 3 * 44JIKUROROOBISHIKUROHEKISHIRUBENZENJUDOTAI |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0244291B2 (en) |
-
1982
- 1982-09-08 JP JP15613582A patent/JPH0244291B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5944332A (en) | 1984-03-12 |
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| JPS597122A (en) | 4-substituted-(trans-4'-(trans-4"-(trans-4'''-alkylcyclohexyl) cyclohexyl)cyclohexyl)benzene | |
| JPS5916853A (en) | Ester derivative of 4-(trans-4'-(trans-4"-alkylcyclohexyl) cyclohexyl)phenol |