JPH02117989A - Ferroelectric liquid crystal composition - Google Patents

Ferroelectric liquid crystal composition

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Publication number
JPH02117989A
JPH02117989A JP27175088A JP27175088A JPH02117989A JP H02117989 A JPH02117989 A JP H02117989A JP 27175088 A JP27175088 A JP 27175088A JP 27175088 A JP27175088 A JP 27175088A JP H02117989 A JPH02117989 A JP H02117989A
Authority
JP
Japan
Prior art keywords
liquid crystal
formulas
tables
crystal composition
compounds
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
Application number
JP27175088A
Other languages
Japanese (ja)
Inventor
Toshihiro Shibata
俊博 柴田
Masaki Kimura
正樹 木村
Norio Kurosawa
則夫 黒沢
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Adeka Corp
Original Assignee
Adeka Argus Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Adeka Argus Chemical Co Ltd filed Critical Adeka Argus Chemical Co Ltd
Priority to JP27175088A priority Critical patent/JPH02117989A/en
Publication of JPH02117989A publication Critical patent/JPH02117989A/en
Pending legal-status Critical Current

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Abstract

PURPOSE:To provide a novel ferroelectric chiral smectic liquid crystal composition composed of a specific optically active compound, a specific phenylpyrimidine compound, etc., and having quick response and high spontaneous polarization. CONSTITUTION:The objective composition is composed of (A) one or more kinds of optically active compounds of formula I [R1 is asymmetric C, (halogen- substituted) 1-18C alkyl or alkoxy] and (B) one or more kinds of compounds selected from the compounds of formulas II-V [R2, R4 to R6, R8 and R9 are asymmetric C, (halogen-substituted) 1-18C alkyl or alkoxy; R3 and R7 are 1-18C alkyl; groups of formula VI and formula VII are (substituted) benzene, pyridine, pyrimidine, pyrazine or pyridazine; m and n are 1 or 2; m+n=3; * represents asymmetric C].

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は新規な液晶組成物に関し、更に詳しくは、高速
応答する新規な強誘電性カイラルスメクチック液晶組成
物に関する。
DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel liquid crystal composition, and more particularly to a novel ferroelectric chiral smectic liquid crystal composition with high-speed response.

〔従来の技術及びその問題点〕[Conventional technology and its problems]

液晶は、種々の電気光学素子として応用され、時計や電
卓等の表示に実用化されてきている。現在、液晶表示素
子としては、ねじれネマチック液晶型(TN型液晶)表
示方式やコレステリック液晶の誘電的配列効果を利用し
たものが最も広範に使用されている。このTN型液晶表
示方式は駆動電圧が低い、消費電力が少ないなど、多く
の利点をもっている。しかし、応答速度に関しては、ま
だ陰極管、エレクトロルミネッセンス、プラズマデイス
プレィ等の発光型表示素子方式に劣っている。ねじれ角
を180@から270°にした新しいTN型液晶表示素
子も開発されているが、応答速度はやはり劣っている。
Liquid crystals have been applied as various electro-optical elements and have been put to practical use in displays such as watches and calculators. Currently, the most widely used liquid crystal display devices are twisted nematic liquid crystal (TN liquid crystal) display systems and devices that utilize the dielectric alignment effect of cholesteric liquid crystal. This TN type liquid crystal display system has many advantages such as low driving voltage and low power consumption. However, in terms of response speed, it is still inferior to light-emitting display element systems such as cathode tubes, electroluminescence, and plasma displays. A new TN type liquid crystal display element with a twist angle of 180° to 270° has also been developed, but its response speed is still inferior.

このように種々の改善の努力は実施されているが、実現
には至っていない。
Although various efforts for improvement have been made as described above, they have not yet been realized.

しかしながら最近、盛んに研究が進められている強誘電
性液晶を用いる新しい表示方式では、著しい応答速度の
改善の可能性がある(C1arkら:Applied 
Phys、 Lett、、36.899 (1980)
) 、この方式は、強誘電性を示すカイラルスメクチッ
クC相(以下、SmC“と略称する)等のカイラルスメ
クチック相を利用する方法である。
However, a new display method using ferroelectric liquid crystals, which has been actively researched recently, has the potential to significantly improve response speed (C1ark et al.: Applied
Phys, Lett, 36.899 (1980)
), this method utilizes a chiral smectic phase such as a chiral smectic C phase (hereinafter abbreviated as "SmC") that exhibits ferroelectricity.

この表示方式に基づき、例えば光学活性なアルキルフェ
ニルピリミジン化合物(特開昭61−24576号)、
あるいは光学活性なアルコキシフェニルピリミジン化合
物(特開昭61−200972号)等が提案された。し
かしながら、これらのフェニルピリミジン化合物を用い
た液晶組成物は応答速度はある程度改善されたもののま
だ充分ではなく、さらに改善がのぞまれていた。
Based on this display method, for example, optically active alkylphenylpyrimidine compounds (JP-A-61-24576),
Alternatively, optically active alkoxyphenylpyrimidine compounds (JP-A-61-200972) have been proposed. However, although the response speed of liquid crystal compositions using these phenylpyrimidine compounds has been improved to some extent, it is still not sufficient, and further improvements have been desired.

〔問題点を解決するための手段〕[Means for solving problems]

本発明者らは、上記現状に鑑み、応答速度に優れ、しか
も自発分極の大きい液晶組成物を見出すべく鋭意検討を
重ねた結果、次の一般式(1)で表されるシトロネリッ
ク酸誘導体を用いた液晶組成物が上記の目的に使用する
のに極めて好適な組成物であることを見出し、本発明に
到達した。
In view of the above-mentioned current situation, the present inventors have conducted intensive studies to find a liquid crystal composition with excellent response speed and large spontaneous polarization. The present inventors have discovered that a liquid crystal composition prepared by the inventors of the present invention is an extremely suitable composition for use for the above purpose, and have arrived at the present invention.

即ち、本発明は、次の一般式(1)で表される光学活性
化合物から選ばれた少なくとも一種と、次の一般式(I
I)〜(V)で表される化合物の中から選ばれた少なく
とも一種からなる強誘電性液晶組成物を提供するもので
ある。
That is, the present invention provides at least one type of optically active compound represented by the following general formula (1) and the following general formula (I
The present invention provides a ferroelectric liquid crystal composition comprising at least one selected from the compounds represented by I) to (V).

(式中R3、R2、R4、R3、R4、R1およびR1
はそれぞれ独立して、不斉炭素原子及び/又は/Sロゲ
ケン換基を有してもよい炭素原子数1〜18のアJレキ
ル基又はアルコキシ基を示し、R1およびR7は炭素原
原子数1〜18のアルキル基を示し、環(×Σおよび(
YΣはそれぞれ独立して、置換基を有してもよいベンゼ
ン環、ピリジン環、ピリミジン環、ピラジン環またはピ
リダジン環を示し、mおよびnはそれぞれl又は2を示
し、m+n=3を示し、*は不斉炭素原子を示す。) 次に、−能代(1)〜(V)で表される各化合物をさら
に詳細に説明する。
(In the formula R3, R2, R4, R3, R4, R1 and R1
each independently represents an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 18 carbon atoms, which may have an asymmetric carbon atom and/or an /S Roggeken substituent, and R1 and R7 each have 1 carbon atom. ~18 alkyl groups, rings (×Σ and (
YΣ each independently represents a benzene ring, pyridine ring, pyrimidine ring, pyrazine ring or pyridazine ring which may have a substituent, m and n each represent l or 2, m + n = 3, * indicates an asymmetric carbon atom. ) Next, each of the compounds represented by -Noshiro (1) to (V) will be explained in more detail.

R1−R1で示される炭素原子数1〜18のアルキル基
としては、メチル、エチル、プロピル、ブチル、ペンチ
ル、ヘキシル、ヘプチル、オクチル、ノニル、デシル、
ウンデシル、ドデシル、テトラデシル、ヘキサデシル、
オクタデシル基等があげられ、炭素原子数1〜18のア
ルコキシ基としては、上記のアルキル基から誘導される
アルコキシ基があげられる。
The alkyl group having 1 to 18 carbon atoms represented by R1-R1 includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl,
undecyl, dodecyl, tetradecyl, hexadecyl,
Examples of the alkoxy group having 1 to 18 carbon atoms include an octadecyl group, and examples of the alkoxy group having 1 to 18 carbon atoms include alkoxy groups derived from the alkyl groups mentioned above.

前記−能代(1)で表される光学活性化合物とは、例え
ば、次のような化合物があげられる。
Examples of the optically active compound represented by -Noshiro (1) include the following compounds.

CH。CH.

CH。CH.

C)lz また、前記−能代(II)で表されるフェニルピリミジ
ン化合物としては、例えば、次のような化合物があげら
れる。
C) lz Examples of the phenylpyrimidine compound represented by -Noshiro (II) include the following compounds.

Nα6 Nα8 Nα 10 また、前記−能代(I[)で表されるフェニルピリミジ
ルフェニル化合物としては、例えば、次のような化合物
があげられる。
Nα6 Nα8 Nα 10 Examples of the phenylpyrimidylphenyl compound represented by -Noshiro (I[) include the following compounds.

Nα15 さらに、前記−能代(It、’)で表されるフェニルピ
リミジン化合物としては、例えば、次のような化合物が
あげられる。
Nα15 Furthermore, examples of the phenylpyrimidine compound represented by -Noshiro (It,') include the following compounds.

さらに、前記−能代(V)で表される二環性ビフェニル
化合物としては、例えば、次のような化合物があげられ
る。
Furthermore, examples of the bicyclic biphenyl compound represented by -Noshiro (V) include the following compounds.

〔実施例〕〔Example〕

以下、本発明を実施例によって説明する。しかしながら
、本発明は以下の実施例によって制限を受けるものでは
ない。
Hereinafter, the present invention will be explained by examples. However, the present invention is not limited by the following examples.

実施例 1 次の四種のフェニルピリミジン化合物を次の割合で混合
した母液晶組成物Aを90%に対して、次の化学式で表
されるカイラルな化合物10%をCR。
Example 1 90% of mother liquid crystal composition A, which is a mixture of the following four types of phenylpyrimidine compounds in the following proportions, was CR mixed with 10% of a chiral compound represented by the following chemical formula.

混合した液晶組成物は、7.2〜42.0°Cの間でエ
ナンチオドロピンクなSmC”相を示した。
The mixed liquid crystal composition exhibited an enantiodropink SmC'' phase between 7.2 and 42.0°C.

また、この液晶組成物を、配向剤としてポリイミドを塗
布し、その表面をラビングすることにより平行配向処理
を施したガラス透明電極を備えた厚さ2μmのセルに注
入して液晶表示素子とし、±15Vの電界(60セ短形
波交流)を印加したところ、明瞭な透過光強度の変化が
観察された。
Further, this liquid crystal composition was injected into a 2 μm thick cell equipped with a glass transparent electrode that had been subjected to a parallel alignment process by applying polyimide as an aligning agent and rubbing its surface to obtain a liquid crystal display element. When an electric field of 15 V (60 cm rectangular wave alternating current) was applied, a clear change in the transmitted light intensity was observed.

また三角波法を用いて自発分極(Ps)を測定したとこ
ろ、0.3 nC/cm”であった、また降゛温時Sm
C”相への相転移温度(Tc)より10°C低い測定温
度(T)Tc−T=10°Cでの応答速度(τ)は40
0 g secであった。
In addition, when the spontaneous polarization (Ps) was measured using the triangular wave method, it was found to be 0.3 nC/cm.
The response speed (τ) at a measurement temperature (T) that is 10°C lower than the phase transition temperature (Tc) to C” phase (Tc - T = 10°C) is 40
It was 0 g sec.

実施例2 実施例1と同じ母液晶組成物Aを90%に対して、次の
化学式で表される光学活性な化合物10%を混合した液
晶組成物を実施例1と同様にして測定したところ、7.
0〜45.6°Cの間でエナンチオトロピックなSmC
”相を示し、自発分極(Ps)は0.2nC/cm” 
、 Tc−T=10°Cの応答速度(τ)は540μs
ecであった一 実施例3 実施例1と同じ母液晶組成物Aを90%に対して、次の
化学式で表される光学活性な化合物10CH3 %を混合した液晶組成物を実施例1と同様にして測定し
たところ、7.5〜49.7°Cの間でエナンチオトロ
ピックなSmC”相を示し、自発分極(Ps)は0.4
nC/cm” 、 Tc−T=10°Cの応答速度(τ
)は900 μsecであった。
Example 2 A liquid crystal composition prepared by mixing 90% of the same base liquid crystal composition A as in Example 1 with 10% of an optically active compound represented by the following chemical formula was measured in the same manner as in Example 1. ,7.
Enantiotropic SmC between 0 and 45.6°C
"Shows phase, spontaneous polarization (Ps) is 0.2nC/cm"
, the response speed (τ) at Tc-T=10°C is 540 μs
Example 3 A liquid crystal composition in which 90% of the same mother liquid crystal composition A as in Example 1 was mixed with 10CH3% of an optically active compound represented by the following chemical formula was prepared in the same manner as in Example 1. When measured at
nC/cm", response speed of Tc-T=10°C (τ
) was 900 μsec.

実施例4 次の四種の液晶化合物を次の割合で混合した液晶組成物
について、実施例1と同様にして測定したところ、47
.5”C以下で安定なSmC”相を示し、Tc−T=1
0”Cで応答速度r =310 gsec 、自発分極
Ps= 2.4 nC/cmzを示した。
Example 4 A liquid crystal composition prepared by mixing the following four types of liquid crystal compounds in the following proportions was measured in the same manner as in Example 1.
.. Shows stable SmC” phase below 5”C, Tc-T=1
At 0''C, response speed r = 310 gsec and spontaneous polarization Ps = 2.4 nC/cmz were exhibited.

実施例5 次の四種の液晶化合物を次の割合で混合した液晶組成物
について、実施例1と同様にして測定したところ、56
.4°C以下で安定な5IIIC“相を示し、Tc−T
 = 10°Cで応答速度r −370p secを示
した。
Example 5 A liquid crystal composition prepared by mixing the following four types of liquid crystal compounds in the following proportions was measured in the same manner as in Example 1.
.. It exhibits a stable 5IIIC phase below 4°C, and Tc-T
It showed a response speed of r -370 p sec at = 10°C.

実施例6 次の四種の液晶化合物を次の割合で混合した液晶組成物
について1.実施例1と同様にして測定しCH。
Example 6 Regarding a liquid crystal composition in which the following four types of liquid crystal compounds were mixed in the following proportions, 1. CH was measured in the same manner as in Example 1.

たところ、50,9°C以下で安定な5rnC”相を示
し、Tc−T=10″Cで応答速度r =330 gs
ec 、自発分極Ps= 4.8 nC/cm” 、T
c−T=40°Cでr −520psec 。
As a result, it showed a stable 5rnC'' phase below 50.9°C, and the response speed r = 330 gs at Tc-T = 10''C.
ec, spontaneous polarization Ps=4.8 nC/cm”, T
r -520 psec at c-T = 40°C.

自発分極Ps = 7.7 nC7cm2を示した。Spontaneous polarization Ps = 7.7 nC7cm2 was exhibited.

実施例7 次の六種の液晶化合物を次の割合で混合した液晶組成物
について、実施例1と同様にして測定したところ、58
.5°Cからo ’c以下まで安定にSmC”相を示し
、Tc−T=10’Cで応答速度r −330psec
、自発分極 Ps= 2.2 nC/c+n” 5Tc
−T=40’Cでτ−790 usec 、自発分極 
Ps= 5.1 nC/cn+”を示した。またこの組
成物はり−バースドメインが全く観察されず、極めて良
好な配向を示した。
Example 7 A liquid crystal composition prepared by mixing the following six types of liquid crystal compounds in the following proportions was measured in the same manner as in Example 1.
.. Stably exhibits SmC'' phase from 5°C to below o'c, response speed r -330 psec at Tc-T=10'C
, spontaneous polarization Ps= 2.2 nC/c+n” 5Tc
-790 usec at T=40'C, spontaneous polarization
Ps=5.1 nC/cn+''. Furthermore, no beam-verse domains were observed in this composition, indicating extremely good orientation.

実施例日 次の六種の液晶化合物を次の割合で混合した液晶組成物
について、実施例1と同様にして測定しCH3 CHl  24% たところ、63.3°Cから0°C以下まで安定にSm
C”相を示し、Tc−T = 10°Cで応答速度r 
=450 psec、自発分極 Ps= 3.2nC/
cm” 、Tc−T=40°Cでτ−620 usec
 、自発分極 Ps= 6 、OnC/cmzを示した
A liquid crystal composition prepared by mixing the six types of liquid crystal compounds listed below in the following proportions was measured in the same manner as in Example 1 and found to be stable from 63.3°C to below 0°C. niSm
C" phase, response speed r at Tc-T = 10°C
=450 psec, spontaneous polarization Ps=3.2nC/
cm”, τ-620 usec at Tc-T=40°C
, spontaneous polarization Ps=6, OnC/cmz.

比較例1 次の五種の液晶化合物を次の割合で混合した液晶組成物
について、実施例1と同様にして測定しCH310% だところ、6.5〜48.7’CT: SmC”相を示
シ、Tc−T=10°Cで応答速度r =990 us
ec 、自発分極Ps=Qを示した。
Comparative Example 1 A liquid crystal composition prepared by mixing the following five types of liquid crystal compounds in the following proportions was measured in the same manner as in Example 1, and the CH310% was found to be 6.5 to 48.7'CT: SmC'' phase. Indication, response speed r = 990 us at Tc-T = 10°C
ec, showed spontaneous polarization Ps=Q.

〔発明の効果〕〔Effect of the invention〕

上記の各実施例に例示されるように、本発明によって、
優れた強誘電性液晶組成物を提供することができる。
As exemplified in each of the above embodiments, according to the present invention,
An excellent ferroelectric liquid crystal composition can be provided.

Claims (1)

【特許請求の範囲】 次の一般式( I )で表される光学活性化合物から選ば
れた少なくとも一種と、次の一般式(II)〜(V)で表
される化合物の中から選ばれた少なくとも一種からなる
強誘電性液晶組成物。 ▲数式、化学式、表等があります▼( I ) ▲数式、化学式、表等があります▼(II) ▲数式、化学式、表等があります▼(III) ▲数式、化学式、表等があります▼(IV) ▲数式、化学式、表等があります▼(V) (式中R_1、R_2、R_4、R_5、R_6、R_
8、およびR_9はそれぞれ独立して、不斉炭素原子及
び/又はハロゲン置換基を有してもよい炭素原子数1〜
18のアルキル基又はアルコキシ基を示し、R_3およ
びR_7は炭素原子数1〜18のアルキル基を示し、環
▲数式、化学式、表等があります▼および▲数式、化学
式、表等があります▼はそれぞれ独立して、置換基を有
してもよいベンゼン環、ピリジン環、ピリミジン環、ピ
ラジン環またはピリダジン環を示し、mおよびnはそれ
ぞれ1又は2を示し、m+n=3を示し、*は不斉炭素
原子を示す。)
[Scope of Claims] At least one type of optically active compound represented by the following general formula (I) and one selected from among the compounds represented by the following general formulas (II) to (V) A ferroelectric liquid crystal composition comprising at least one type. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼( IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) (In the formula, R_1, R_2, R_4, R_5, R_6, R_
8, and R_9 each independently have 1 to 1 carbon atoms, which may have an asymmetric carbon atom and/or a halogen substituent.
18 alkyl group or alkoxy group, R_3 and R_7 represent an alkyl group having 1 to 18 carbon atoms, and the rings ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and ▲There are mathematical formulas, chemical formulas, tables, etc.▼ are respectively Independently represents a benzene ring, pyridine ring, pyrimidine ring, pyrazine ring or pyridazine ring which may have a substituent, m and n each represent 1 or 2, m+n=3, * represents asymmetric Indicates a carbon atom. )
JP27175088A 1988-10-27 1988-10-27 Ferroelectric liquid crystal composition Pending JPH02117989A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP27175088A JPH02117989A (en) 1988-10-27 1988-10-27 Ferroelectric liquid crystal composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP27175088A JPH02117989A (en) 1988-10-27 1988-10-27 Ferroelectric liquid crystal composition

Publications (1)

Publication Number Publication Date
JPH02117989A true JPH02117989A (en) 1990-05-02

Family

ID=17504313

Family Applications (1)

Application Number Title Priority Date Filing Date
JP27175088A Pending JPH02117989A (en) 1988-10-27 1988-10-27 Ferroelectric liquid crystal composition

Country Status (1)

Country Link
JP (1) JPH02117989A (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61291679A (en) * 1985-06-18 1986-12-22 Chisso Corp Ferroelectric chiral smectic liquid crystal composition
JPS6337186A (en) * 1986-08-01 1988-02-17 Matsushita Electric Ind Co Ltd Liquid crystal composition
JPS63253074A (en) * 1987-04-08 1988-10-20 Adeka Argus Chem Co Ltd Pyrimidine compound
JPS63256688A (en) * 1987-04-13 1988-10-24 Matsushita Electric Ind Co Ltd Liquid crystal composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61291679A (en) * 1985-06-18 1986-12-22 Chisso Corp Ferroelectric chiral smectic liquid crystal composition
JPS6337186A (en) * 1986-08-01 1988-02-17 Matsushita Electric Ind Co Ltd Liquid crystal composition
JPS63253074A (en) * 1987-04-08 1988-10-20 Adeka Argus Chem Co Ltd Pyrimidine compound
JPS63256688A (en) * 1987-04-13 1988-10-24 Matsushita Electric Ind Co Ltd Liquid crystal composition

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