JPH04103555A - Cyclobutane derivative - Google Patents
Cyclobutane derivativeInfo
- Publication number
- JPH04103555A JPH04103555A JP2222201A JP22220190A JPH04103555A JP H04103555 A JPH04103555 A JP H04103555A JP 2222201 A JP2222201 A JP 2222201A JP 22220190 A JP22220190 A JP 22220190A JP H04103555 A JPH04103555 A JP H04103555A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- trans
- crystal compound
- cyclobutane derivative
- formula
- 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.)
- Granted
Links
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title claims abstract 5
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001930 cyclobutanes Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 phosphor compound Chemical class 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
- FFIXAFACUXWNCV-VVPTUSLJSA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC(O)=CC=2)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC(O)=CC=2)CC1 FFIXAFACUXWNCV-VVPTUSLJSA-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
- HNCRCGCAYWISBU-MLRKGSHFSA-N CCC[C@H](CC1)CC[C@@H]1[C@H](CC1)CC[C@@H]1C(C=C1)=CC=C1OCC1CCC1 Chemical compound CCC[C@H](CC1)CC[C@@H]1[C@H](CC1)CC[C@@H]1C(C=C1)=CC=C1OCC1CCC1 HNCRCGCAYWISBU-MLRKGSHFSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 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
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- NGGFJWZLNOBGNO-UHFFFAOYSA-N methylcyclobutane hydrobromide Chemical compound CC1CCC1.Br NGGFJWZLNOBGNO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing 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
- 102220197965 rs144594252 Human genes 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なシクロブタン誘導体液晶化合物および
該化合物を有効成分とする液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel cyclobutane derivative liquid crystal compound and a liquid crystal composition containing the compound as an active ingredient.
（従来の技術）
液晶表示素子は液晶物質が持つ光学異方性及び認電異方
性を利用したものであるが、その表示様式によってＴＮ
型（ねじれネマチックＷ）、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實は貫る。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
てできるだけ広い温度範囲で液晶相を示し、更に表示素
子の種類によって異なる最適な銹電異方性値（Δε）を
有するようにしなければならない。(Prior art) Liquid crystal display elements utilize the optical anisotropy and electrocognitive anisotropy of liquid crystal materials, but due to their display format, TN
It is divided into various types such as type (twisted nematic W), DS type (dynamic scattering type), guest-host type, and DAP type.
The properties of liquid crystal materials suitable for each use are consistent. However, all liquid crystal materials have in common that they must be stable against moisture, air, heat, light, etc., and they must exhibit a liquid crystal phase over as wide a temperature range as possible, centering on room temperature, and they must also be stable against moisture, air, heat, light, etc. It is necessary to have an optimal galvanic anisotropy value (Δε) that varies depending on the type.
しかし現在のところ凰−化合物ではこのような条件を満
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ｔ−使用しているのが現状
である。最近は特に低温（−４０℃程度）から高温（１
００℃以上）Ｋわたって動作する表示素子が要求される
ようになってきているのて、より広い温度範囲ですぐれ
念動作特性を持った液晶組成物が要望されている。However, at present, there is no phosphor compound that satisfies these conditions, and the current situation is to use a liquid crystal composition obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds. Recently, especially from low temperature (about -40℃) to high temperature (1
As display elements that operate over a temperature range of 00° C. or higher are required, there is a need for liquid crystal compositions that have excellent telekinetic properties over a wider temperature range.
（発明が解決しようとする課題〕
本発明の目的は低粘性で高温まで動作する液晶表示素子
に８！！な新規な液晶化合物及び液晶組成物を提供する
ととＫある。(Problems to be Solved by the Invention) An object of the present invention is to provide novel liquid crystal compounds and liquid crystal compositions for use in liquid crystal display elements that have low viscosity and operate at high temperatures.
本発明は一般式
りぎに本発明の化合物の製造法を示すと、４−（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〕フェノールをＮ。The present invention shows a method for producing the compound of the present invention using the general formula: 4-(trans-4-(trans-4-alkylcyclohexyl)cyclohexyl)phenol with N.
Ｎ−ジメチルホルムアミド（以下、ＤＭＦと略す）を溶
媒とし、無水炭酸カリウムと〜−臭化アルキルシクロブ
タンと反応を行い、目的のシクロブタン誘導体液晶化合
物を製造したり
（上式に於いてＲは炭素数１〜１０の直鎖又は側鎖のア
ルキル基を示し、ｎは１〜１０を示す）で表わされるシ
クロブタン誘導体液晶化合物及びこれを少なくとも一種
含有すること′ｆｔ％徴とする液晶組成物である。Using N-dimethylformamide (hereinafter abbreviated as DMF) as a solvent, anhydrous potassium carbonate and ~-alkyl bromide cyclobutane are reacted to produce the desired cyclobutane derivative liquid crystal compound (in the above formula, R is the number of carbon atoms). The present invention relates to a cyclobutane derivative liquid crystal compound represented by 1 to 10 linear or side chain alkyl groups, where n is 1 to 10), and a liquid crystal composition containing at least one type thereof in ft%.
本発明の化合物は小さい正の誘電異方性値を示し、液晶
温度範囲が広く、特に高い液晶−透明点（Ｓｍ−Ｉ点）
を持っていて、なおかつ低粘性の化合物であり、更に熱
、空気、水分、光等に安定であるため、低温から高温ま
で広い温度範囲で動作する液晶組成物を得るのに極めて
有用な化合物である。The compounds of the present invention exhibit small positive dielectric anisotropy values, a wide liquid crystal temperature range, and a particularly high liquid crystal clearing point (Sm-I point).
It is a compound with low viscosity and is stable against heat, air, moisture, light, etc., so it is an extremely useful compound for obtaining liquid crystal compositions that operate in a wide temperature range from low to high temperatures. be.
（Ｉ）
（Ｒ％！ｌは前記に同じ）
（本発明の効果〕
本発明の化合物は他の多くの液晶化合物、すなワチエス
テル系、シッフ塩基系、ビフェニル系、フェニルシクロ
ヘキサン系、複素環系等の液晶化合物との相溶性がよく
、本発明の化合物を液晶組成物に加えることによシ、Δ
ｎは小さく保持でき、Ｎ−Ｉ点を上昇させることができ
るために、高温度でも動作可能々液晶表示素子に用いる
液晶組成物に好適な化合物である。(I) (R%!l is the same as above) (Effects of the present invention) The compound of the present invention can be applied to many other liquid crystal compounds, such as Watier ester type, Schiff base type, biphenyl type, phenylcyclohexane type, and heterocyclic type. It has good compatibility with liquid crystal compounds such as, and by adding the compound of the present invention to a liquid crystal composition,
Since n can be kept small and the N-I point can be raised, it is a compound suitable for liquid crystal compositions used in liquid crystal display elements that can operate even at high temperatures.
以下、実施例により本発明の化合物の製造法及び使用例
について更に詳細に説明するが、本発明はこの実施例に
よって何等限定されるものではない。EXAMPLES Hereinafter, the production method and usage examples of the compounds of the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例１
１−シクロブチルメチルオキシ−４−〔トランス−４−
プロピルシクロヘキシル−トランス−４−シクロヘキシ
ル〕ベンゼン（（Ｉ） 式テＲ−Ｃ４Ｈ＠−ｎ ｔ＝
ｌのもの）の製造
４−〔トランス−４−（トランス−４−プロピルシクロ
ヘキシル）シクロヘキシル〕フェノール８、Ｏｆ （０
，０１％＃）に２００ｍＯＤＭＦ’を加え、これに無水
炭酸カリウム５ｏｒｔ加えた。攪拌しながら臭化メチル
シクロブタン４５１ （（ＬＯ３モル）を加え、８０℃
で１２時間反反応性った。Example 1 1-Cyclobutylmethyloxy-4-[trans-4-
Propylcyclohexyl-trans-4-cyclohexyl]benzene ((I) Formula TeR-C4H@-nt=
Preparation of 4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]phenol 8, Of (0
, 01% #) was added with 200 mODMF', and to this was added 5 ort of anhydrous potassium carbonate. While stirring, add 451 methylcyclobutane bromide ((LO3 mol)) and heat at 80°C.
It remained unreactive for 12 hours.
反応終了後、反応液に水を加え、析出した油状物をトル
エンで抽出した。トルエン層＝ｉ２Ｎ水酸化ナトリウム
て洗い、ついで中性になるまで水でトルエン層を洗った
。After the reaction was completed, water was added to the reaction solution, and the precipitated oil was extracted with toluene. The toluene layer was washed with i2N sodium hydroxide, and then the toluene layer was washed with water until it became neutral.
無水硫酸ナトリウムでトルエン層を乾燥後、トルエンを
減圧にして留去した。残った結晶をアセトンで再結晶を
行った。結晶−スメクチック点（Ｃ−８ｍ点）５８℃、
スメクチック−透明点（ＳＩＯ−Ｉ点）１９０°Ｃであ
った。収量１．５ｇ（収量４３％）であった。このもの
が目的物であることｔ−ＮＭＲスペクトル、元素分析で
確認した。After drying the toluene layer with anhydrous sodium sulfate, toluene was distilled off under reduced pressure. The remaining crystals were recrystallized with acetone. Crystal-smectic point (C-8m point) 58°C,
The smectic clearing point (SIO-I point) was 190°C. The yield was 1.5 g (yield 43%). It was confirmed by t-NMR spectrum and elemental analysis that this product was the target product.
実施例２（使用例）
トランス−４−プロピル−（４′−シアノフェニル）シ
クロヘキサン ２８ｘｉ％トランスー４−ペ
ンチル−（４′−シアノフェニル）シクロヘキサン
４２Ｘ量％トランスー４−へブチル−（４′−
シアノ７二二ル）シクロヘキサン ３ｏｌ量
％なる組成の液晶組成物のネマチック−透明点は５２℃
である。この液晶組成物をセル厚１０ｐｔＮ０ＴＮセル
（ねじれネマチックセル）に封入したもＯの動作しきい
電圧は１．５３Ｖ、飽和電圧は２．１２Ｖであつ九。又
粘度は２０℃で２３ｅｐ。Example 2 (use example) trans-4-propyl-(4'-cyanophenyl)cyclohexane 28xi% trans-4-pentyl-(4'-cyanophenyl)cyclohexane
42X amount% trans-4-hebutyl-(4'-
The nematic clearing point of a liquid crystal composition with a composition of 3 ol % of cyano(72)cyclohexane is 52°C.
It is. When this liquid crystal composition was sealed in a 10 pt N0TN cell (twisted nematic cell), the operating threshold voltage was 1.53V and the saturation voltage was 2.12V. Also, the viscosity is 23ep at 20°C.
ΔｎｔｉＯ，１１９であつ念。ΔntiO, 119.
この液晶組成物９０部に実施例１で展進した４−シクロ
ブチルメトキシ−〔トランス−４−（）ランス−４−プ
ロピルシクロヘキシル）シクロヘキシル〕ベンゼン１０
部を加えた液晶混合物のネマチック−透明点は５８℃に
上昇し、ΔＣは８．８に低下し、しきい電圧はＬ６３Ｖ
、飽和電圧は２、．２８Ｖと上昇しているが、粘度は２
４ｅｐとわずか上昇しただけでありｌ！Ｉは０．１２０
と殆んど変らず、大巾にネマチック液晶温度範囲を高温
側に上昇させることができた。To 90 parts of this liquid crystal composition was added 10 parts of the 4-cyclobutylmethoxy-[trans-4-()trans-4-propylcyclohexyl)cyclohexyl]benzene developed in Example 1.
The nematic-clearing point of the liquid-crystal mixture with the addition of 30% rises to 58°C, ΔC drops to 8.8, and the threshold voltage is L63V.
, the saturation voltage is 2, . Although it has increased to 28V, the viscosity is 2
There was only a slight increase of 4ep! I is 0.120
The temperature range of the nematic liquid crystal could be significantly raised to the high temperature side, with almost no change.
以上that's all
Claims (2)
を示し、ｎは１〜１０を示す） で表わされるシクロブタン誘導体液晶化合物。(1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the above formula, R represents a straight chain or side chain alkyl group having 1 to 10 carbon atoms, and n represents 1 to 10.) A cyclobutane derivative liquid crystal compound.
少なくとも一種含有することを特徴とする液晶組成物。(2) A liquid crystal composition containing at least one cyclobutane derivative liquid crystal compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2222201A JP2829436B2 (en) | 1990-08-23 | 1990-08-23 | Cyclobutane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2222201A JP2829436B2 (en) | 1990-08-23 | 1990-08-23 | Cyclobutane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04103555A true JPH04103555A (en) | 1992-04-06 |
| JP2829436B2 JP2829436B2 (en) | 1998-11-25 |
Family
ID=16778723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2222201A Expired - Lifetime JP2829436B2 (en) | 1990-08-23 | 1990-08-23 | Cyclobutane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2829436B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000109840A (en) * | 1998-09-29 | 2000-04-18 | Merck Patent Gmbh | Liquid crystal compound and liquid crystal medium |
| US7462427B2 (en) | 2001-09-14 | 2008-12-09 | Qinetiq Limited | Liquid crystal compounds with branched or cyclic end groups |
-
1990
- 1990-08-23 JP JP2222201A patent/JP2829436B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000109840A (en) * | 1998-09-29 | 2000-04-18 | Merck Patent Gmbh | Liquid crystal compound and liquid crystal medium |
| US7462427B2 (en) | 2001-09-14 | 2008-12-09 | Qinetiq Limited | Liquid crystal compounds with branched or cyclic end groups |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2829436B2 (en) | 1998-11-25 |
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