JPH01193A - liquid crystal composition - Google Patents
liquid crystal compositionInfo
- Publication number
- JPH01193A JPH01193A JP62-155804A JP15580487A JPH01193A JP H01193 A JPH01193 A JP H01193A JP 15580487 A JP15580487 A JP 15580487A JP H01193 A JPH01193 A JP H01193A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal composition
- compound
- compounds
- phase
- 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.)
- Pending
Links
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は、強誘電性液晶表示素子等に用いられろ液晶組
成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to a liquid crystal composition used in ferroelectric liquid crystal display elements and the like.
「従来技術とその問題点」
近年、強誘電性を示す液晶組成物として各種のものが提
案されている。ところが、配向性、応答性等が良好で、
しかもカイラルスメクティックＣ（Ｓｅ３）相の温度領
域の下限温度が室温以下に在る液晶組成物は、はとんど
存在しない。"Prior Art and its Problems" In recent years, various types of liquid crystal compositions exhibiting ferroelectricity have been proposed. However, the orientation, responsiveness, etc. are good,
Moreover, there are almost no liquid crystal compositions in which the lower limit temperature of the temperature range of the chiral smectic C (Se3) phase is below room temperature.
例えば、Ｇｏｏｄｂｙ等の提案に基づいて、下記（Ａ）
′式、（Ｂ）式、（Ｃ）式で表される化合物Ａ、Ｂ、Ｃ
を混合すると、配向性、応答性等の良好な液晶組成物を
調製できる。（以下の式に添えた（Ｓ）および（Ｒ）の
記号は、その側鎖をなす光学活性基の絶対配置がＳ型あ
るいはＲ型であることを示す。）ところがこれら化合物
Ａ、Ｂ、Ｃからなる液晶組成物の転移温度と配合比の関
係を調べると、ＳＣ＊相を示す温度範囲は最良でも約１
３℃〜５５℃である。For example, based on the proposal of Goodby et al., the following (A)
Compounds A, B, and C represented by formula ', formula (B), and formula (C)
By mixing these, a liquid crystal composition with good alignment, responsiveness, etc. can be prepared. (The symbols (S) and (R) attached to the following formulas indicate that the absolute configuration of the optically active group forming the side chain is S type or R type.) However, these compounds A, B, C Examining the relationship between the transition temperature and compounding ratio of a liquid crystal composition consisting of
The temperature is 3°C to 55°C.
また、下記（Ｄ）式、（Ｅ）式で表される液晶化合物り
、Ｅを混合して得られる液晶組成物のＳｃ”相の温度範
囲は、最良でも約２０℃〜６５℃である。Further, the temperature range of the Sc'' phase of the liquid crystal composition obtained by mixing the liquid crystal compounds represented by the following formulas (D) and (E) and E is approximately 20°C to 65°C at best.
（Ｓ）
（Ｓン
一方、異なる骨格を持つ化合物を混合することによって
Ｓｃ”相の温度範囲を拡大することができるという提案
もなされている。この提案に基づいて上記化合物Ａ−Ｅ
を混合して得られる組成物のＳｃゝ相の温度範囲は、最
良でも約Ｏ〜６３℃である。(S) (S) On the other hand, it has also been proposed that the temperature range of the Sc" phase can be expanded by mixing compounds with different skeletons. Based on this proposal, the above compounds A-E
The temperature range of the Sc phase of the composition obtained by mixing is at best about 0 to 63°C.
このように、従来の強誘電性液晶組成物は、Ｓｃ＊相の
下限温度が十分低くないため、実用上不安があった。As described above, in the conventional ferroelectric liquid crystal compositions, the lower limit temperature of the Sc* phase is not sufficiently low, and therefore, there are concerns regarding practical use.
本発明は上記事情に鑑みてなされたもので、配向性、応
答性等が良好で、しかもＳｃ＊相の下限温度が室温以下
に存在する強誘電性液晶組成物を提供することを目的と
する。The present invention was made in view of the above circumstances, and an object of the present invention is to provide a ferroelectric liquid crystal composition that has good orientation, responsiveness, etc., and has a lower limit temperature of the Sc* phase below room temperature. .
「問題点を解決するための手段」
本発明の液晶組成物は、少なくとも、下記一般式（ｉ）
で表されるピリミジン系化合物Ｉを含有するものである
。"Means for Solving the Problems" The liquid crystal composition of the present invention has at least the following general formula (i):
It contains a pyrimidine compound I represented by:
（但し、（ｒ）式中Ｒ，はＣｎＨｘｎ＋ｒｚ ＲｔはＣ
ｍＨｔｒａ＋ｒで表されるアルキル基、また４≦ｎ≦８
．６≦ｍ≦１４）このような一般式（１）で表される化
合物■の中テモ、ｎ＝６、ｒａ＝ １２のものが最適で
ある。(However, in formula (r), R is CnHxn+rz Rt is C
an alkyl group represented by mHtra+r, and 4≦n≦8
．． 6≦m≦14) The compound represented by the general formula (1) in which n=6 and ra=12 is optimal.
このピリミジン系化合物■を添加することにより液晶組
成物のＳｃ’″相の温度範囲を低温化することができ、
室温以下でもＳｃ”相を示す液晶組成物を調製すること
ができる。By adding this pyrimidine compound (2), the temperature range of the Sc''' phase of the liquid crystal composition can be lowered,
A liquid crystal composition exhibiting the Sc'' phase even at room temperature or lower can be prepared.
このピリミジン系化合物■と混合される液晶化合物には
、各種のものを利用できるが、液晶組成物には前記化合
物Ａ、Ｈのようなエステル結合を有する液晶化合物を少
なくとも一種類配合することが望ましい。Various types of liquid crystal compounds can be used as the liquid crystal compound to be mixed with the pyrimidine compound (2), but it is preferable that the liquid crystal composition contains at least one type of liquid crystal compound having an ester bond such as the above-mentioned compounds A and H. .
組成物に対するピリミジン系化合物■の配合量は、７０
モル％以下であることが望ましい。化合物Ｉの配合比が
７０モル％を越えると、Ｓｃ”相の上限温度が大幅に低
下して室温の範囲に入ってしまう問題が生じる。The amount of pyrimidine compound (■) in the composition is 70
It is desirable that it is less than mol%. If the blending ratio of Compound I exceeds 70 mol %, a problem arises in that the upper limit temperature of the Sc'' phase decreases significantly and falls within the room temperature range.
「実施例」
次に、実施例に沿って本発明の液晶組成物を更に詳しく
説明する。"Example" Next, the liquid crystal composition of the present invention will be described in more detail with reference to Examples.
（実施例１）
下記（ＩＩ）式で表されるピリミジン系化合物■を、前
記化合物Ａ−Ｅの混合物に添加して、化合物Ｈの添加量
と転移温度の関係を調べた。(Example 1) A pyrimidine compound (2) represented by the following formula (II) was added to the mixture of compounds A to E, and the relationship between the amount of compound H added and the transition temperature was investigated.
化合物Ａ−Ｅの混合物における各成分の配合比は、化合
物Ａ：化合物Ｂ：化合物Ｃ：化合物Ｄ：化合物Ｅ＝２７
： ４０．５ ： ７．５ ＋ ２０ ： ５ （モ
ル比）であった。The blending ratio of each component in the mixture of compounds A-E is Compound A: Compound B: Compound C: Compound D: Compound E = 27
: 40.5 : 7.5 + 20 : 5 (molar ratio).
結果を第１図に示す。The results are shown in Figure 1.
また、比較のために、従来の液晶組成物の配合比と転移
温度の関係を調べた。Furthermore, for comparison, the relationship between the blending ratio and transition temperature of conventional liquid crystal compositions was investigated.
まず比較例１として、前記化合物Ａ 、Ｂ 、Ｃからな
る液晶組成物を調べた。 この際、化合物Ａ、ＢがＡ：
Ｂ・４ ：６ （モル比）の割合で配合された混合物Ｚ
に化合物Ｃを添加して組成物を調製した。First, as Comparative Example 1, a liquid crystal composition consisting of the compounds A, B, and C was investigated. At this time, compounds A and B are A:
B・Mixture Z blended at a ratio of 4:6 (mole ratio)
A composition was prepared by adding Compound C to.
結果を第２図に示す。The results are shown in Figure 2.
次に、比較例２として、前記化合物り、Ｅからなる液晶
組成物を調べた。結果を第３図に示す。Next, as Comparative Example 2, a liquid crystal composition consisting of the above-mentioned compounds E was investigated. The results are shown in Figure 3.
さらに、比較例３として、前記化合物Ａ−Ｅからなる液
晶組成物を調べた。 この際、化合物Ａ。Furthermore, as Comparative Example 3, a liquid crystal composition consisting of the compounds A to E was investigated. At this time, compound A.
Ｂ、ＣがＡ：Ｂ：Ｃ＝３７ ： ５５．５ ： ７．５
（モル比）の割合で配合された混合物Ｙに、化合物
り、ＥがＤ：Ｅ＝８：２ （モル比）の割合で配合さ
れた混合物Ｘを添加して組成物を調製した。結果を第４
図に示す。B and C are A:B:C=37: 55.5: 7.5
A composition was prepared by adding a mixture X, in which the compounds E were blended in a ratio of D:E=8:2 (mole ratio), to a mixture Y, in which the compounds were blended in a ratio of D:E=8:2 (mole ratio). 4th result
As shown in the figure.
第１図の結果から、ピリミジン系化合物■が添加された
実施例１の液晶組成物にあっては、比較−例１〜３の液
晶組成物よりも、Ｓｃ”相の温度範囲、特に下限温度を
更に低温化できることが判明した。From the results shown in FIG. 1, it can be seen that the liquid crystal composition of Example 1 to which the pyrimidine compound ■ was added had a higher temperature range in the Sc'' phase, especially the lower limit temperature, than the liquid crystal compositions of Comparative Examples 1 to 3. It was found that the temperature could be lowered further.
そして、ピリミジン系化合物■が１０モル％添加された
組成物は、Ｓｃ”相の温度範囲が一１Ｏ〜＋６０℃とか
なり低温化していることが分かる。なお、ピリミジン系
化合物■の配合比が７０モル％を越えると、Ｓｃ”相の
上限温度が大幅に低下して４０℃以下になるので、化合
物Ｈの添加量は７０モル％以下の範囲で設定することが
望ましいと思われる。It can be seen that the temperature range of the Sc" phase in the composition to which 10 mol% of the pyrimidine compound (2) is added is considerably lower, from 110 to +60°C. It should be noted that the blending ratio of the pyrimidine compound (2) is 70°C. If it exceeds mol %, the upper limit temperature of the Sc'' phase will drop significantly to 40° C. or less, so it seems desirable to set the amount of compound H added in the range of 70 mol % or less.
次に、ピリミジン系化合物■の添加量が１０モル％の液
晶組成物を、セル厚が２μｍの液晶セルに注入して、配
向性と応答性を調べた。液晶セルは、インジウム−スズ
酸化物（ＩＴＯ）製透明電極が形成されたガラス基板に
ポリイミドを塗布し！軸方向にラビング処理して作成し
た。Next, a liquid crystal composition containing 10 mol % of the pyrimidine compound (1) was injected into a liquid crystal cell having a cell thickness of 2 μm, and the orientation and response were examined. The liquid crystal cell is made by applying polyimide to a glass substrate on which transparent electrodes made of indium-tin oxide (ITO) are formed! Created by rubbing in the axial direction.
作成した液晶セルを調べたところ、液晶組成物は極めて
良好な配向性を示しており双安定も実現できた。ついで
、±ｌＯｖの方形波の交流電圧を印加して応答速度を調
べたところ、室温下で２００ ’μＳｅＣ以下の高速
応答性を発揮することが確認された。When the prepared liquid crystal cell was examined, the liquid crystal composition showed extremely good alignment and was also able to achieve bistable properties. Then, when a square wave AC voltage of ±lOv was applied to examine the response speed, it was confirmed that a high-speed response of 200' μSeC or less was exhibited at room temperature.
（実施例２〜４）
実施例！で用いたピリミジン系化合物■に代えて、下記
（［［）式、（ＩＶ）式、（Ｖ）式で表されるピリミジ
ン系化合物ｍ 、ＩＶ 、Ｖをそれぞれ用いて液晶組成
物を調製し、実施例１と同様の実験を行った。(Examples 2 to 4) Examples! In place of the pyrimidine compound (1) used in the above, a liquid crystal composition was prepared using pyrimidine compounds m, IV, and V represented by the following formulas ([), (IV), and (V), respectively, An experiment similar to Example 1 was conducted.
その結果、いずれのピリミジン系化合物■〜■を用いた
場合でも、実施例１の場合と同様に、それらを添加する
ことにより、組成物のＳｃ”相の温度範囲の低温化を実
現できた。As a result, no matter which of the pyrimidine compounds (1) to (4) were used, the temperature range of the Sc'' phase of the composition could be lowered by adding them, as in Example 1.
また、いずれの化合物■〜■が添加な組成物も、良好な
配向性および応答性を示した。Furthermore, the compositions in which any of the compounds (1) to (2) were added also exhibited good orientation and responsiveness.
「発明の効果」
以上説明したように、本発明の液晶組成物は、少なくと
も、−服代（１）で表されるピリミジン系化合物を含有
するものなので、Ｓｃ”相の温度範囲の低温化を実現で
きる。"Effects of the Invention" As explained above, since the liquid crystal composition of the present invention contains at least the pyrimidine compound represented by (1), it is possible to lower the temperature range of the Sc'' phase. realizable.
そして、本発明によれば、配向性、応答性等が良好で、
しかもＳｃ”相の下限温度が室温以下に存在する強誘電
性液晶組成物を提供できる。According to the present invention, the orientation, responsiveness, etc. are good,
Moreover, it is possible to provide a ferroelectric liquid crystal composition in which the lower limit temperature of the Sc'' phase exists below room temperature.
第１図は実施例Ｉの液晶組成物の転移温度と配合比の関
係を示す相図、第２図ないし第４図はそれぞれ比較例１
〜３の液晶組成物の転移温度と配合比の関係を示す相図
である。Figure 1 is a phase diagram showing the relationship between the transition temperature and compounding ratio of the liquid crystal composition of Example I, and Figures 2 to 4 are each of Comparative Example 1.
FIG. 3 is a phase diagram showing the relationship between transition temperature and compounding ratio of liquid crystal compositions No. 3 to 3. FIG.
Claims (1)
ミジン系化合物を含有することを特徴とする液晶組成物
。 ▲数式、化学式、表等があります▼−−−−−（ I ） （但し、（ I ）式中Ｒ＿１はＣ＿ｎＨ＿２＿ｎ＿＋＿
１、Ｒ＿２はＣ＿ｍＨ＿２＿ｍ＿＋＿１で表されるアル
キル基、また４≦ｎ≦８、６≦ｍ≦１４）（２）上記液
晶組成物をなす他の成分として、エステル結合を有する
液晶化合物が添加されたこと特徴とする特許請求の範囲
第１項記載の液晶組成物。 （３）上記一般式（ I ）で表されるピリミジン系化合
物の配合比が７０モル％以下であることを特徴とする特
許請求の範囲第１項および第２項記載の液晶組成物。 （４）上記一般式（ I ）中ｎが６、ｍが１２であるこ
とを特徴とする特許請求の範囲第１項ないし第３項記載
の液晶組成物。[Scope of Claims] (1) A liquid crystal composition containing at least a pyrimidine compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼−−−−−(I) (However, in the formula (I), R_1 is C_nH_2_n_+_
1. R_2 is an alkyl group represented by C_mH_2_m_+_1, and 4≦n≦8, 6≦m≦14) (2) A liquid crystal compound having an ester bond is added as another component forming the liquid crystal composition. A liquid crystal composition according to claim 1, characterized in that: (3) The liquid crystal composition according to claims 1 and 2, wherein the blending ratio of the pyrimidine compound represented by the general formula (I) is 70 mol% or less. (4) The liquid crystal composition according to any one of claims 1 to 3, wherein n is 6 and m is 12 in the general formula (I).
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62155804A JPS64193A (en) | 1987-06-23 | 1987-06-23 | Liquid crystal composition |
| US07/170,916 US4824597A (en) | 1987-06-23 | 1988-03-17 | Liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62155804A JPS64193A (en) | 1987-06-23 | 1987-06-23 | Liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01193A true JPH01193A (en) | 1989-01-05 |
| JPS64193A JPS64193A (en) | 1989-01-05 |
Family
ID=15613813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62155804A Pending JPS64193A (en) | 1987-06-23 | 1987-06-23 | Liquid crystal composition |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4824597A (en) |
| JP (1) | JPS64193A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4780240A (en) * | 1985-08-02 | 1988-10-25 | Chisso Corporation | Liquid crystal composition |
| US4906074A (en) * | 1987-09-28 | 1990-03-06 | Semiconductor Energy Laboratory Co., Ltd. | FLC liquid crystal electro-optical device having microdomains within pixels |
| JPH01106874A (en) * | 1987-10-21 | 1989-04-24 | Chisso Corp | Optically active phenylpyrimidine compound and liquid crystal composition |
| JP2691405B2 (en) * | 1987-11-06 | 1997-12-17 | チッソ株式会社 | Ferroelectric liquid crystal composition |
| JP2534283B2 (en) * | 1987-11-26 | 1996-09-11 | チッソ株式会社 | Ferroelectric liquid crystal composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986000087A1 (en) * | 1984-06-07 | 1986-01-03 | Seiko Instruments & Electronics Ltd. | Liquid crystal compound |
| DE3500909A1 (en) * | 1985-01-12 | 1986-07-17 | Merck Patent Gmbh, 6100 Darmstadt | PYRIMIDINE |
| DE3515374C2 (en) * | 1985-04-27 | 1998-02-26 | Hoechst Ag | Chiral tilted smectic liquid crystalline phases and their use in electro-optical display elements |
| DE3515373A1 (en) * | 1985-04-27 | 1986-11-06 | Merck Patent Gmbh, 6100 Darmstadt | NITROGENIC HETEROCYCLES |
| JPH0764829B2 (en) * | 1985-05-27 | 1995-07-12 | 帝国化学産業株式会社 | Liquid crystal compound |
| JPH07113112B2 (en) * | 1985-06-18 | 1995-12-06 | チッソ株式会社 | Ferroelectric chiral smectic liquid crystal composition |
| JPS62209190A (en) * | 1986-03-10 | 1987-09-14 | Alps Electric Co Ltd | Liquid crystal composition |
-
1987
- 1987-06-23 JP JP62155804A patent/JPS64193A/en active Pending
-
1988
- 1988-03-17 US US07/170,916 patent/US4824597A/en not_active Expired - Lifetime
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