JPH0219158B2 - - Google Patents
Info
- Publication number
- JPH0219158B2 JPH0219158B2 JP17844280A JP17844280A JPH0219158B2 JP H0219158 B2 JPH0219158 B2 JP H0219158B2 JP 17844280 A JP17844280 A JP 17844280A JP 17844280 A JP17844280 A JP 17844280A JP H0219158 B2 JPH0219158 B2 JP H0219158B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal composition
- alkyl group
- voltage
- carbon atoms
- 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 54
- 239000000203 mixture Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- BNIKCZNNRBDPAY-UHFFFAOYSA-N 2-(4-nitrophenyl)-1,3-dioxane Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1OCCCO1 BNIKCZNNRBDPAY-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 2
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 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
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- DBMHLMFFXUIZPL-UHFFFAOYSA-N [O-][N+](=O)C1=CC=CC=C1C1OCCCO1 Chemical compound [O-][N+](=O)C1=CC=CC=C1C1OCCCO1 DBMHLMFFXUIZPL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Landscapes
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Liquid Crystal Substances (AREA)
Description
本発明は液晶組成物に係わり、さらに詳しくは
1.5V程度の低電圧で動作可能なTN型液晶表示体
に適した液晶組成物に関する。
液晶材料を利用した電気光学的表示素子には従
来様々な表示原理が応用され実用化されている。
なかでも、２枚の基板間で液晶層の配列方向を連
続的にねじれ構造をもたせた、いわゆるTN型液
晶表示体は実用性が高く、腕時計、電卓などの表
示素子として主流を占めている。
現在、腕時計などに用いられている液晶表示体
は、そのほとんどが3Vの直流電圧で駆動されて
いるが、表示体の薄型化への技術革新を考えた場
合不都合な点が多い。というのは、3V駆動させ
るには現在使用されている1.5Vの電池を２個使
用するか、または１個の電池を使用して昇圧回路
を設けるなどしなければいけない。
一方、液晶表示体が1.5V程度の低電圧で駆動
できれば、昇圧回路が不要となり、その結果昇圧
回路およびそれに関連する部分がなくなり、表示
体の薄型化に有利となる。またコストの低減も図
れるなど利点が多い。
液晶表示体を1.5V駆動させるために、液晶表
示素子の構成面から工夫を施す手段として、液晶
分子長軸の基板面に対する配向傾斜角（チルト
角）を大きくして駆動電圧の低下を実現したいわ
ゆるチルト方式がある。しかし、この方式では液
晶素子の液晶層の厚みが不均一になり、色むらが
生じやすく、表示品質の低下をまねく欠点があ
る。
本発明においては、こうした表示素子の構成面
の改善には限度があるととらえ、液晶材料自体の
改良を検討した。
本発明の目的は、TN型液晶表示体に適する液
晶組成物を提供することである。さらに他の目的
は1.5V程度の低電圧で動作可能な液晶組成物を
提供することである。
本発明の液晶組成物は、
一般式が
（但し、R1は炭素数３〜５の直鎖アルキル基
を示し、R2は炭素数１、２のアルキル基又は４
の直鎖アルキル基を示す。）で表わされる化合物
の58.6〜61.7wt％と、
一般式が
（但しR3は炭素数２のアルキル基又は４の直
鎖アルキル基を示す。）で表わされる化合物の
24.6〜26.2wt％と、
化学式が
で表わされる化合物の6.8〜7.1wt％と、
化学式が
で表わされる化合物の５〜10wt％とからなるこ
とを特徴とする。
一般式が
で表わされる化合物が58.6wt％未満では、温度特
性が充分でなく、61.7wt％をこえると、誘電異方
性を小さくする。
また、一般式が
で表わされる化合物が24.6wt％未満では、誘電異
方性を充分大きくすることができず、26.2wt％を
こえると温度特性を悪くする。
さらに、化学式が
で表わされる化合物が6.8wt％未満では、温度範
囲が充分ではなく、7.1wt％をこえると温度特性
を悪くする。
ついで、化学式が
で表わされる化合物が5wt％未満では、低電圧駆
動のための駆動電圧を下げることができず、
10wt％をこえると液晶組成物の液晶性を低下さ
せる。
上記液晶組成物に使用する、２−（Ｐ−ニトロ
フエニル）−１，３−ジオキサンは市販の１，３
−プロパンジオールとＰ−シアノベンズアルデヒ
ドをスルホサリチル酸の存在下、ベンゼン中で反
応させることにより容易に製造できる。
液晶表示体の駆動電圧は液晶のしきい値電圧
Vthに基づいて決められるが、Vthは液晶材料の誘
電異方性や弾性的性質によつて決定されることは
周知である。上記２−（Ｐ−ニトロフエニル）−
１，３−ジオキサンは非液晶化合物であるが、他
の液晶化合物と容易に混合する。そして液晶分子
間に介在すると液晶分子間の相互作用が変化し、
液晶相としての弾性的性質が変化する。この結果
駆動電圧を低下させることが考察できる。２−
（Ｐ−ニトロフエニル）−１，３−ジオキサンの液
晶材料はすべてのネマチツク液晶化合物と混合し
て用いられる。その代表的なものを以下に示す。
（但し上式中Ｒは直鎖アルキル基を示す。）
以下実施例に従い本発明の態様を詳述する。
実施例 １
市販の１，３−プロパンジオール4.3ｇと、Ｐ
−ニトロベンズアルデヒド6.9ｇと、スルホサリ
チル酸0.044ｇをベンゼン10ml中で24時間還流下
に加熱した。反応後室温まで冷却し、0.1Nの水
酸化ナトリウムを加え、エーテル抽出をした。エ
ーテル溶液を飽和亜硫酸水素ナトリウム水溶液、
及び水で洗浄した。エーテル溶液を無水硫酸ナト
リウムで乾燥した後、エーテルを留去した。残留
物をエタノールと水の混合溶媒で再結晶し、係わ
る２−（Ｐ−ニトロフエニル）−１，３−ジオキサ
ンを製取した。
mp 104℃
実施例 ２
The present invention relates to a liquid crystal composition, and more particularly, to a liquid crystal composition.
This invention relates to a liquid crystal composition suitable for a TN type liquid crystal display that can operate at a low voltage of about 1.5V. Conventionally, various display principles have been applied and put into practical use in electro-optical display elements using liquid crystal materials.
Among these, the so-called TN type liquid crystal display, in which the liquid crystal layer has a continuously twisted structure between two substrates, is highly practical and is the mainstream display element for watches, calculators, etc. Currently, most liquid crystal displays used in watches and other devices are driven by 3V DC voltage, but this has many disadvantages when considering technological innovations to make displays thinner. This is because in order to drive 3V, it is necessary to use two 1.5V batteries, which are currently in use, or to use one battery and install a booster circuit. On the other hand, if a liquid crystal display can be driven at a low voltage of about 1.5V, a booster circuit is not required, and as a result, the booster circuit and its related parts are eliminated, which is advantageous for making the display thinner. It also has many advantages, including cost reduction. In order to drive the liquid crystal display at 1.5V, we improved the structure of the liquid crystal display element by increasing the tilt angle of the long axis of the liquid crystal molecules with respect to the substrate surface, thereby reducing the driving voltage. There is a so-called tilt method. However, this method has the drawback that the thickness of the liquid crystal layer of the liquid crystal element becomes non-uniform, color unevenness tends to occur, and the display quality deteriorates. In the present invention, we considered that there is a limit to the improvement of the structure of such a display element, and therefore investigated improvements to the liquid crystal material itself. An object of the present invention is to provide a liquid crystal composition suitable for a TN type liquid crystal display. Still another object is to provide a liquid crystal composition that can operate at a low voltage of about 1.5V. The liquid crystal composition of the present invention has the general formula: (However, R 1 represents a straight-chain alkyl group having 3 to 5 carbon atoms, and R 2 represents an alkyl group having 1 or 2 carbon atoms or a 4-carbon alkyl group.
represents a straight-chain alkyl group. ) and the general formula is (However, R 3 represents an alkyl group having 2 carbon atoms or a straight chain alkyl group having 4 carbon atoms.)
The chemical formula is 24.6-26.2wt%. 6.8-7.1wt% of the compound represented by and the chemical formula is It is characterized by consisting of 5 to 10 wt% of the compound represented by The general formula is If the amount of the compound represented by is less than 58.6 wt%, the temperature characteristics will not be sufficient, and if it exceeds 61.7 wt%, the dielectric anisotropy will be reduced. Also, the general formula is If the amount of the compound represented by is less than 24.6 wt%, the dielectric anisotropy cannot be sufficiently increased, and if it exceeds 26.2 wt%, the temperature characteristics will deteriorate. Additionally, the chemical formula is If the amount of the compound represented by is less than 6.8 wt%, the temperature range will not be sufficient, and if it exceeds 7.1 wt%, the temperature characteristics will deteriorate. Then, the chemical formula is If the compound represented by is less than 5wt%, the driving voltage for low voltage driving cannot be lowered,
If it exceeds 10wt%, the liquid crystallinity of the liquid crystal composition will be reduced. The 2-(P-nitrophenyl)-1,3-dioxane used in the liquid crystal composition is a commercially available 1,3-dioxane.
It can be easily produced by reacting -propanediol and P-cyanobenzaldehyde in benzene in the presence of sulfosalicylic acid. The driving voltage of the liquid crystal display is the threshold voltage of the liquid crystal.
It is determined based on V th , and it is well known that V th is determined by the dielectric anisotropy and elastic properties of the liquid crystal material. The above 2-(P-nitrophenyl)-
Although 1,3-dioxane is a non-liquid crystal compound, it easily mixes with other liquid crystal compounds. When the liquid crystal molecules intervene, the interaction between the liquid crystal molecules changes,
The elastic properties of the liquid crystal phase change. As a result, it can be considered that the drive voltage is lowered. 2-
The (P-nitrophenyl)-1,3-dioxane liquid crystal material is used in admixture with all nematic liquid crystal compounds. Typical examples are shown below. (However, in the above formula, R represents a straight-chain alkyl group.) Hereinafter, embodiments of the present invention will be described in detail according to Examples. Example 1 4.3 g of commercially available 1,3-propanediol and P
- 6.9 g of nitrobenzaldehyde and 0.044 g of sulfosalicylic acid were heated under reflux in 10 ml of benzene for 24 hours. After the reaction, the mixture was cooled to room temperature, 0.1N sodium hydroxide was added, and the mixture was extracted with ether. ether solution to saturated sodium bisulfite aqueous solution,
and washed with water. After drying the ether solution over anhydrous sodium sulfate, the ether was distilled off. The residue was recrystallized from a mixed solvent of ethanol and water to obtain the related 2-(P-nitrophenyl)-1,3-dioxane. mp 104℃ Example 2
【表】【table】
【表】
表１に示す液晶組成物を形成し、厚さ8μmの
TN型液晶セルに封入して、20℃における電圧Vs
コントラスト特性を調べたところ第１図に示すよ
うなデータを得た。図において実線で示す特性a1
は上記液晶組成物の電圧Vsコントラスト特性で
あり、点線で示す特性ｂは上記表中の２−（Ｐ−
ニトロフエニル）−１，３−ジオキサンを添加す
る前の液晶組成物母体系の電圧Vsコントラスト
特性を示したものである。従つて、第１図より明
らかなように本発明による２−（Ｐ−ニトロフエ
ニル）−１，３−ジオキサンを含む液晶組成物は
1.5V程度の定電圧駆動が可能である。
実施例 ３[Table] The liquid crystal composition shown in Table 1 was formed, and a thickness of 8 μm was formed.
When sealed in a TN type liquid crystal cell, the voltage V s at 20℃
When the contrast characteristics were investigated, data as shown in FIG. 1 was obtained. Characteristic a 1 shown by the solid line in the figure
is the voltage V s contrast characteristic of the above liquid crystal composition, and the characteristic b shown by the dotted line is 2-(P-
2 shows the voltage Vs contrast characteristics of the liquid crystal composition matrix before adding (nitrophenyl)-1,3-dioxane. Therefore, as is clear from FIG. 1, the liquid crystal composition containing 2-(P-nitrophenyl)-1,3-dioxane according to the present invention is
Constant voltage drive of around 1.5V is possible. Example 3
【表】【table】
【表】
表２に示す液晶組成物を形成し、実施例２と同
様に特性を調べたところ第１図の一点破線で示す
特性a2を得た。従つて、上記表２に示す液晶組成
物は1.5V程度の駆動電圧で十分に動作できる。
このように本発明による、駆動電圧の低下に有
効な成分である２−（Ｐ−ニトロフエニル）−１，
３−ジオキサンを含む液晶組成物は、低電圧駆動
のTN型液晶表示体の液晶組成物として優れる。
本発明によれば、
で表わされる所定の化合物と、液晶表示は何等関
係のない非液晶化合物
[Table] A liquid crystal composition shown in Table 2 was formed and its properties were investigated in the same manner as in Example 2, and the property a2 shown by the dotted line in FIG. 1 was obtained. Therefore, the liquid crystal composition shown in Table 2 above can operate satisfactorily with a driving voltage of about 1.5V. As described above, according to the present invention, 2-(P-nitrophenyl)-1, which is an effective component for lowering the driving voltage,
A liquid crystal composition containing 3-dioxane is excellent as a liquid crystal composition for a TN type liquid crystal display driven at a low voltage. According to the invention, The specified compound represented by is a non-liquid crystal compound that has no relation to liquid crystal display.
【式】とをそれぞれ所定量
添加することにより、1.5V駆動の実現をさせる
ことができた。
また、この化合物を使用することにより、従来
の液晶化合物間の相溶性の悪いものであつても、
相溶性を改善することができ、使用できる液晶化
合物の幅を拡大させる働きも有している。
また、上記実施例に示した液晶組成物は一例で
あり、実施例以外の公知液晶化合物、例えば正の
誘電異方性を有する液晶系と共に液晶組成物を調
整すれば特性の優れた低電圧駆動のTN液晶組成
物ができるのは明確であることにおいて、本発明
は決して本実施例に限定されるものではない。By adding a predetermined amount of each of [Formula] and [Formula], it was possible to realize 1.5V drive. In addition, by using this compound, even if conventional liquid crystal compounds have poor compatibility,
It can improve compatibility and also has the function of expanding the range of usable liquid crystal compounds. Furthermore, the liquid crystal composition shown in the above example is just an example, and if the liquid crystal composition is adjusted with a known liquid crystal compound other than the example, for example, a liquid crystal system having positive dielectric anisotropy, low voltage drive with excellent characteristics can be achieved. It is clear that the TN liquid crystal composition can be made, but the present invention is by no means limited to this example.
第１図は本発明によつて提供される液晶組成物
の電圧Vsコントラスト特性を示す図であり、実
線a1は２−（Ｐ−ニトロフエニル）−１，３−ジオ
キサンを5wt％含有する液晶組成物の、また一点
破線a2は２−（Ｐ−ニトロフエニル）−１，３−ジ
オキサンを10wt％含有する液晶組成物の、また
点線ｂは前記化合物を除いた液晶組成物母体系の
それぞれ電圧Vsコントラスト特性である。
FIG. 1 is a diagram showing the voltage V s contrast characteristics of the liquid crystal composition provided by the present invention, where the solid line a 1 indicates the liquid crystal composition containing 5 wt% of 2-(P-nitrophenyl)-1,3-dioxane. The dotted line a2 represents the voltage of the liquid crystal composition containing 10 wt% of 2-(P-nitrophenyl)-1,3-dioxane, and the dotted line b represents the voltage of the liquid crystal composition matrix excluding the above compound. V s contrast characteristics.
Claims (1)
を示し、R2は炭素数１、２のアルキル基又は４
の直鎖アルキル基を示す。）で表わされる化合物
の58.6〜61.7wt％と、 一般式が （但しR3は炭素数２のアルキル基又は４の直
鎖アルキル基を示す。）で表わされる化合物の
24.6〜26.2wt％と、 化学式が で表わされる化合物の6.8〜7.1wt％と、 化学式が で表わされる化合物の５〜10wt％とからなるこ
とを特徴とする液晶組成物。[Claims] 1. The general formula is (However, R 1 represents a straight-chain alkyl group having 3 to 5 carbon atoms, and R 2 represents an alkyl group having 1 or 2 carbon atoms or a 4-carbon alkyl group.
represents a straight-chain alkyl group. ) and the general formula is (However, R 3 represents an alkyl group having 2 carbon atoms or a straight chain alkyl group having 4 carbon atoms.)
The chemical formula is 24.6-26.2wt%. 6.8-7.1wt% of the compound represented by and the chemical formula is A liquid crystal composition comprising 5 to 10 wt% of a compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17844280A JPS57102980A (en) | 1980-12-17 | 1980-12-17 | Liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17844280A JPS57102980A (en) | 1980-12-17 | 1980-12-17 | Liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57102980A JPS57102980A (en) | 1982-06-26 |
| JPH0219158B2 true JPH0219158B2 (en) | 1990-04-27 |
Family
ID=16048586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17844280A Granted JPS57102980A (en) | 1980-12-17 | 1980-12-17 | Liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57102980A (en) |
-
1980
- 1980-12-17 JP JP17844280A patent/JPS57102980A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57102980A (en) | 1982-06-26 |
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