JPH10338878A - Ferroelectric liquid crystal composition - Google Patents
Ferroelectric liquid crystal compositionInfo
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- JPH10338878A JPH10338878A JP16356797A JP16356797A JPH10338878A JP H10338878 A JPH10338878 A JP H10338878A JP 16356797 A JP16356797 A JP 16356797A JP 16356797 A JP16356797 A JP 16356797A JP H10338878 A JPH10338878 A JP H10338878A
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Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、安定な強誘電性液
晶状態をとり得、例えば液晶テレビ等のデイスプレイ
用、光プリンタ-ヘッド、ライトバルブ等に利用される
オプトエレクトロニクス関連素子として有用な強誘電性
液晶組成物及び光スイッチング素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention provides a stable ferroelectric liquid crystal state, which is useful as an optoelectronics-related element used for displays such as liquid crystal televisions, optical printer heads, light valves, and the like. The present invention relates to a dielectric liquid crystal composition and an optical switching device.
【0002】[0002]
【従来の技術】ネマチック液晶材料を用いた液晶素子に
代わるものとして、強誘電性液晶の光スイッチング現象
を利用した表示方式がN.A.ClarkとS.T.Lagerwallにより
提案された(Applied Phys. Lett., 1980, Vol36, p.89
9)。この強誘電性液晶を利用した素子は双安定性を示
し、しかも、従来の液晶素子に比べて光学的な応答がμ
secのオーダーと速いという優れた特徴を持っている。2. Description of the Related Art As a substitute for a liquid crystal device using a nematic liquid crystal material, a display system utilizing the optical switching phenomenon of a ferroelectric liquid crystal has been proposed by NAClark and STLagerwall (Applied Phys. Lett., 1980, Vol. p.89
9). The device using this ferroelectric liquid crystal shows bistability, and has an optical response μ compared to the conventional liquid crystal device.
It has an excellent feature that it is fast and on the order of sec.
【0003】しかし、この強誘電性液晶材料を実際の素
子として用いるためには、多くの物性及び特性が要求さ
れる。その中でも基本的なものとしては、室温を含む広
い温度範囲でキラルスメクティックC(Sc*)相を示すこ
と、高速応答をすることであるが、この他にも種々の物
性及び特性が要求される。現在、単一の化合物で、これ
らの物性及び特性を満足させることはできず、いくつか
の化合物を混合した強誘電性液晶組成物が検討されてい
る。However, in order to use this ferroelectric liquid crystal material as an actual device, many physical properties and characteristics are required. Among them, the basic ones are to exhibit a chiral smectic C (Sc * ) phase in a wide temperature range including room temperature, and to provide a high-speed response. In addition, various physical properties and characteristics are required. . At present, these properties and properties cannot be satisfied by a single compound, and a ferroelectric liquid crystal composition in which several compounds are mixed is being studied.
【0004】ところで、強誘電性液晶組成物を調製する
には、強誘電性液晶化合物だけを用いて混合する必要は
なく、非キラル化合物であって、スメクティックC(S
c)相を示す液晶化合物或いはこの混合物(ベース液晶
と呼ばれる)に、キラルな化合物を添加することによっ
ても調製できる。By the way, in order to prepare a ferroelectric liquid crystal composition, it is not necessary to mix using only a ferroelectric liquid crystal compound.
c) It can also be prepared by adding a chiral compound to a liquid crystal compound showing a phase or a mixture thereof (called a base liquid crystal).
【0005】近年、室温を含む広い温度範囲でのキラル
スメクティック(Sc*)相の発現、高速応答を有する数
多くの強誘電性液晶組成物が報告されている。しかし、
従来型の強誘電性液晶組成物は、スイッチングのしきい
値電圧が高いため消費電力が大きくなり、液晶素子のコ
ストが高くなって、実用化を阻んでおり、しきい値電圧
を低くすることが重要な課題となっている。[0005] In recent years, many ferroelectric liquid crystal compositions have been reported which exhibit a chiral smectic (Sc * ) phase in a wide temperature range including room temperature and have a high-speed response. But,
The conventional ferroelectric liquid crystal composition has a high switching threshold voltage, which consumes a large amount of power, increases the cost of the liquid crystal element, hinders practical application, and lowers the threshold voltage. Is an important issue.
【0006】しきい値電圧を低くするという試みは、ネ
マチック液晶組成物では、例えばジフルオロシアノ化合
物等が報告(特開平5-286920号公報)されてい
るが、これらの化合物をフェニルピリミジン系の強誘電
性液晶組成物に添加した場合、相系列が乱れたり、キラ
ルスメクティックC(Sc*)相の温度範囲が狭くなる等の
問題が生じ、添加率等使用上の制限が大きい。In an attempt to lower the threshold voltage, for example, difluorocyano compounds and the like have been reported as nematic liquid crystal compositions (Japanese Patent Laid-Open No. 5-286920). When added to the dielectric liquid crystal composition, problems such as disorder of the phase series and narrowing of the temperature range of the chiral smectic C (Sc * ) phase occur, and there are large restrictions on use such as the addition ratio.
【0007】一方、強誘電性液晶組成物中にテトラシア
ノキノジメタン(TCNQ)等の自由度の大きいイオン性物
質を添加する方法は、しきい値電圧を低くするという点
では、極めて有効な方法ではあるけれども、イオン性物
質を加える前の液晶組成物のしきい値が高過ぎる場合に
は、その効果が発現されても実用上なおしきい値電圧が
高くなってしまう(例えば、特開平5-88183号公
報)。このため、イオン性物質等の添加剤を加えずに、
しきい値電圧を低くした液晶組成物が求められている。On the other hand, a method of adding an ionic substance having a high degree of freedom, such as tetracyanoquinodimethane (TCNQ), to a ferroelectric liquid crystal composition is extremely effective in reducing the threshold voltage. However, if the threshold value of the liquid crystal composition before the addition of the ionic substance is too high, the threshold voltage becomes practically high even if the effect is exhibited (for example, see Japanese Unexamined Patent Application Publication No. -88183). For this reason, without adding additives such as ionic substances,
There is a need for a liquid crystal composition with a reduced threshold voltage.
【0008】一般に、高速応答可能な液晶組成物はしき
い値電圧も低いと言われており、現在まで、数多くの高
速応答可能なベース液晶、キラル化合物が報告されてい
るが、これらは必ずしも、しきい値電圧の低いものでは
なかった。In general, it is said that a liquid crystal composition capable of high-speed response also has a low threshold voltage, and a large number of base liquid crystals and chiral compounds capable of high-speed response have been reported to date. The threshold voltage was not low.
【0009】[0009]
【発明が解決しようとする課題】本発明は上記課題を解
決するためになされたもので、本発明の目的は液相(Is
o)-コレステリック相(Ch)-スメクティックA相(S
A)-キラルスメクティックC相(Sc*)の相系列を示し、
Sc*相を示す温度範囲が広く、かつ高速応答性を有し、
しかもしきい値電圧の低い強誘電性液晶組成物を提供す
ることである。SUMMARY OF THE INVENTION The present invention has been made to solve the above problems, and an object of the present invention is to provide a liquid phase (Is
o) -Cholesteric phase (Ch) -Smectic A phase (S
A) shows a phase sequence of chiral smectic C phase (Sc * ),
The temperature range showing the Sc * phase is wide and has high-speed response,
Moreover, it is to provide a ferroelectric liquid crystal composition having a low threshold voltage.
【0010】[0010]
【課題を解決するための手段】本発明は、下記一般式
(I)で表わされる一種以上の化合物と、一般式(II)
で表される一種以上の化合物と、一般式(III)で表わ
される一種以上の化合物と、一般式(IV)又は(IV)で
表わされる一種以上の化合物を含有することからなる第
1の強誘電性液晶組成物、特には前記第1の強誘電性液
晶組成物に、下記一般式(V)で表わされる化合物の少
なくとも1種を含有させた第2の強誘電性液晶組成物、
またさらには、前記第1又は第2の強誘電性液晶組成物
に、下記一般式(VI)〜(VII)で表わされる化合物の
少なくとも1種を含有させることからなる第3の強誘電
性液晶組成物に関するものである。According to the present invention, there is provided a compound represented by the general formula (II):
A first compound comprising at least one compound represented by formula (III), at least one compound represented by formula (III), and at least one compound represented by formula (IV) or (IV) A second ferroelectric liquid crystal composition in which the dielectric liquid crystal composition, particularly the first ferroelectric liquid crystal composition, contains at least one compound represented by the following general formula (V):
Still further, a third ferroelectric liquid crystal comprising at least one compound represented by the following general formulas (VI) to (VII) in the first or second ferroelectric liquid crystal composition: It relates to a composition.
【化7】 Embedded image
【化8】 Embedded image
【化9】 Embedded image
【化10】 Embedded image
【化11】 Embedded image
【化12】 (上記の各式中、R1、R3、R5及びR12は炭素数1〜18
のアルキル又はアルコキシ基を、R2、R4、R6、R11、
R13、R15、R16及びR18は炭素数1〜18のアルキル基
を、R7は炭素数3〜20の直鎖或いは分岐鎖アルキル基
を、R8、R9及びR10はそれぞれ独立に水素、炭素数1〜
15の直鎖或いは分岐鎖アルキル基、炭素数2〜15の
アルケニル基又は炭素数7〜10のアラルキル基を、R
14及びR17は炭素数1〜18のアルキレン基を、Rfは炭
素数1又は2のフルオロアルキル基を、X1は-O-、-OCO-
又は-OCOO-を、X2は-COO-、-O-又は単結合を示し、X3は
-COO-、-OCO-、-CH2O-、-OCH2-、-C≡C-又は単結合を示
し、X4は-COO-、-CH2O-又は-O-を示し、X5は-O-又は-OC
O-を、A及びBはそれぞれ独立にハロゲン、シアノ基又
は含フッ素アルキル基で置換されていてもよい含六員環
を、C*は不斉炭素を、p、qは0又は1を、nは0又は1
を表わす。)Embedded image (In each of the above formulas, R 1 , R 3 , R 5 and R 12 have 1 to 18 carbon atoms.
An alkyl or alkoxy group of R 2 , R 4 , R 6 , R 11 ,
R 13 , R 15 , R 16 and R 18 are an alkyl group having 1 to 18 carbon atoms, R 7 is a linear or branched alkyl group having 3 to 20 carbon atoms, and R 8 , R 9 and R 10 are each Independently hydrogen, carbon number 1
15 linear or branched alkyl groups, alkenyl groups having 2 to 15 carbon atoms or aralkyl groups having 7 to 10 carbon atoms
14 and R 17 are an alkylene group having 1 to 18 carbon atoms, Rf is a fluoroalkyl group having 1 or 2 carbon atoms, X 1 is -O-, -OCO-
Or -OCOO-, X 2 represents -COO-, -O- or a single bond, and X 3 represents
-COO -, - OCO -, - CH 2 O -, - OCH 2 -, - C≡C- or a single bond, X 4 is -COO -, - CH 2 O- or -O- are shown, X 5 is -O- or -OC
O-, A and B each independently represent a halogen-containing, six-membered ring optionally substituted with a cyano group or a fluorine-containing alkyl group, C * represents an asymmetric carbon, p, q represents 0 or 1, n is 0 or 1
Represents )
【0011】また、本発明は上記のいずれかの強誘電性
液晶組成物を構成要素とする光スイッチング素子に関す
るものである。[0011] The present invention also relates to an optical switching element comprising any one of the above ferroelectric liquid crystal compositions.
【0012】[0012]
【発明の実施の形態】本発明の液晶組成物は、前記一般
式(I)、(II)及び(III)成分、及び必要に応じて
用いられる一般式(V)〜(VIII)成分からなるベース
液晶に、光学活性な(IV)又は(IV)を混合した混合物
からなる。BEST MODE FOR CARRYING OUT THE INVENTION The liquid crystal composition of the present invention comprises the above-mentioned components of the general formulas (I), (II) and (III) and, if necessary, the components of the general formulas (V) to (VIII). It is composed of a base liquid crystal mixed with optically active (IV) or (IV).
【0013】ベース液晶における(I)、(II)及び
(III)成分、必要に応じて用いられる(IV)及び
(V)〜(VI)成分の混合比、或いは各成分中のそれぞ
れの化合物の混合比等は、各化合物の性質上、一概に決
定することは困難であるが、概ね次のような混合比の範
囲から選定することができる。The components (I), (II) and (III) in the base liquid crystal, the mixing ratio of the components (IV) and (V) to (VI) used as necessary, or the ratio of each compound in each component The mixing ratio and the like are difficult to determine unconditionally due to the properties of each compound, but can be generally selected from the following range of the mixing ratio.
【0014】一般式(I)、(II)の化合物におけるR1
〜R4のアルキル基又はアルコキシ基の炭素数は、製造上
の見地から、炭素数18以下とされる。R 1 in the compounds of the general formulas (I) and (II)
The number of carbon atoms in the alkyl or alkoxy group to R 4 are, from a manufacturing perspective, is the number 18 or less carbon atoms.
【0015】一般式(III)の化合物のR5、R6のアルキ
ル基又はアルコキシ基の炭素数も製造上の見地から、炭
素数18以下とされる。なお、この化合物で、pが0の
ものは、R5がアルキル基又はアルコキシ基、qが0、Xが
-O-、-OCO-又は-OCOO-のものが望ましく、pが1のもの
は、R5はアルキル基、qが1、Xが-O-であるものがキラ
ルスメクティックC相(Sc*相)の温度範囲の拡大及び室
温でのしきい値電圧の低下等の見地から望ましい。The number of carbon atoms of the alkyl group or alkoxy group of R 5 and R 6 in the compound of the general formula (III) is also set to 18 or less from the viewpoint of production. In this compound, when p is 0, R 5 is an alkyl group or an alkoxy group, q is 0, and X is
-O-, -OCO- or -OCOO- is desirable, and when p is 1, R 5 is an alkyl group, q is 1 and X is -O- is a chiral smectic C phase (Sc * phase). This is desirable from the viewpoints such as the expansion of the temperature range and the decrease in the threshold voltage at room temperature.
【0016】上記一般式(I)〜(III)で表わされる
化合物としては、表1〜表5に掲げるものを例示でき
る。The compounds represented by the above general formulas (I) to (III) include those listed in Tables 1 to 5.
【0017】[0017]
【表1】 [Table 1]
【0018】[0018]
【表2】 [Table 2]
【0019】[0019]
【表3】 [Table 3]
【0020】[0020]
【表4】 [Table 4]
【0021】[0021]
【表5】 [Table 5]
【0022】一般式(I)の化合物と一般式(III)の
化合物とは、I-Ch-SA-Sc*の相系列を示し、かつSc*相
のとる高温域側の温度範囲を広げるという見地から、化
合物(I)/化合物(III)の混合比を98/2〜70/3
0(重量比)の範囲で選定することが好ましい。又、こ
のベース液晶に対して、一般式(II)で表わされる一種
以上の化合物を、組成物全体に対して2〜40重量%と
することが、より効果的に上記目的が達成できるために
望ましい。The compound of the general formula (I) and the compound of the general formula (III) show a phase sequence of I-Ch-SA-Sc * and extend the temperature range of the Sc * phase on the high temperature side. From a viewpoint, the mixing ratio of compound (I) / compound (III) is 98/2 to 70/3.
It is preferable to select within the range of 0 (weight ratio). In order to achieve the above object more effectively, it is preferable that the content of one or more compounds represented by the general formula (II) is 2 to 40% by weight based on the total composition. desirable.
【0023】次に、本発明の強誘電性液晶組成物のカイ
ラル液晶成分である一般式(IV)又は(IV)の化合物に
おいては、Rfは炭素数1又は2のフルオロアルキル基を
示すが、好ましくはトリフルオロメチル基である。Next, in the compound of the general formula (IV) or (IV) which is the chiral liquid crystal component of the ferroelectric liquid crystal composition of the present invention, Rf represents a fluoroalkyl group having 1 or 2 carbon atoms. Preferably it is a trifluoromethyl group.
【0024】また、R7は炭素数3〜20の直鎖又は分岐
鎖アルキル基であるが、特には、炭素数3〜15の直鎖
又は分岐鎖アルキル基が好ましい。これらのうち、分岐
鎖アルキル基であって、不斉炭素を有する基は光学活性
基であるものが好ましい。R 7 is a straight-chain or branched-chain alkyl group having 3 to 20 carbon atoms, and particularly preferably a straight-chain or branched-chain alkyl group having 3 to 15 carbon atoms. Among them, the branched alkyl group having asymmetric carbon is preferably an optically active group.
【0025】R8、R9、R10は、それぞれ独立に水素又は
炭素数1〜15の直鎖或いは分岐鎖アルキル基、炭素数
2〜15のアルケニル基又は炭素数7〜10のアラルキ
ル基であるが、特には、R8、R9、R10は炭素数1〜10
の直鎖又は分岐鎖アルキル基が好ましい。R 8 , R 9 and R 10 are each independently hydrogen or a linear or branched alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. In particular, R 8 , R 9 and R 10 each have 1 to 10 carbon atoms.
Are preferred.
【0026】また、一般式(IV)又は(IV)において、
A及びBとしては、それぞれ独立に置換又は無置換の含
六員環基である。In the general formula (IV) or (IV),
A and B are each independently a substituted or unsubstituted 6-membered ring group.
【0027】本発明の一般式(IV)又は(IV)で表わさ
れる化合物としては、表6に掲げるものを例示できる。The compounds represented by the general formula (IV) or (IV) of the present invention include those listed in Table 6.
【0028】[0028]
【表6】 [Table 6]
【0029】上記一般式(I)、(II)又は(III)を
配合したベース液晶組成物に対して、これらのキラル液
晶成分である一般式(IV)又は(IV)で表わされる化合
物を添加することにより、本発明の第1の強誘電性液晶
組成物とすることができるが、この一般式(IV)又は
(IV)で表わされる化合物の添加量は、ベース液晶組成
物に対して2〜20重量%とすることが好ましい。The compound represented by the general formula (IV) or (IV), which is a chiral liquid crystal component, is added to the base liquid crystal composition containing the above general formula (I), (II) or (III). By doing so, the first ferroelectric liquid crystal composition of the present invention can be obtained. However, the amount of the compound represented by the general formula (IV) or (IV) is 2 to the base liquid crystal composition. It is preferable to set it to 20% by weight.
【0030】次に、一般式(V)の化合物のR11、R12の
アルキル又はアルコキシ基の炭素数は、製造上の見地か
ら炭素数18以下である。この化合物を上記第1の強誘
電性液晶組成物に対して添加することにより、I-Ch-SA-
Sc*の相系列を乱さず、応答速度を遅くせず、しかもし
きい値電圧を大きくすることなく、キラルスメクティッ
クC(Sc*)相の高温域を広がった第2の強誘電性液晶組
成物を得ることができる。この場合、一般式(V)の化
合物は上記第1の強誘電性液晶組成物に対して、5〜6
0重量%加えることが好ましい。Next, the alkyl or alkoxy group of R 11 and R 12 in the compound of the formula (V) has 18 or less carbon atoms from the viewpoint of production. By adding this compound to the first ferroelectric liquid crystal composition, I-Ch-SA-
A second ferroelectric liquid crystal composition having a high temperature range of a chiral smectic C (Sc * ) phase without disturbing the Sc * phase series, reducing the response speed, and increasing the threshold voltage. Can be obtained. In this case, the compound of the general formula (V) is added to the first ferroelectric liquid crystal composition in an amount of 5 to 6%.
It is preferable to add 0% by weight.
【0031】本発明の一般式(V)で表わされる化合物
としては、表7に掲げるものを例示できる。The compounds represented by the general formula (V) of the present invention include those listed in Table 7.
【0032】[0032]
【表7】 [Table 7]
【0033】一般式(VI)の化合物は、R13がアルキル
基を炭素数18以下、R14が炭素数1〜8のアルキレン
基、R15が炭素数1〜6のアルキル基であるものが、応
答速度を速くするという見地から好ましい。また、一般
式(VII)の化合物は、R16のアルキル基の炭素数が18
以下で、R17が炭素数3〜11のアルキレン基、R18が炭
素数1〜10のアルキル基のものが好ましい。The compounds of the general formula (VI) are those wherein R 13 is an alkyl group having 18 or less carbon atoms, R 14 is an alkylene group having 1 to 8 carbon atoms, and R 15 is an alkyl group having 1 to 6 carbon atoms. This is preferable from the viewpoint of increasing the response speed. The compound of the general formula (VII) has an alkyl group of R 16 having 18 carbon atoms.
In the following, it is preferable that R 17 is an alkylene group having 3 to 11 carbon atoms and R 18 is an alkyl group having 1 to 10 carbon atoms.
【0034】これらの一般式(VI)又は(VII)の化合
物は上記第1又は第2の強誘電性液晶組成物に対して添
加することにより、高速応答性及び低いしきい値電圧の
発現した本発明の第3の強誘電性液晶組成物を得ること
ができる。この場合、一般式(VI)又は(VII)の化合
物は、上記第1及び/又は第2の強誘電性液晶組成物に
対して、5〜30重量%加えることが好ましい。By adding these compounds of the general formula (VI) or (VII) to the above-mentioned first or second ferroelectric liquid crystal composition, high-speed response and low threshold voltage were developed. The third ferroelectric liquid crystal composition of the present invention can be obtained. In this case, the compound of the general formula (VI) or (VII) is preferably added in an amount of 5 to 30% by weight based on the first and / or second ferroelectric liquid crystal composition.
【0035】本発明の一般式(VI)又は(VII)で表わ
される化合物としては、表8に掲げるものを例示でき
る。As the compounds represented by the general formula (VI) or (VII) of the present invention, those listed in Table 8 can be exemplified.
【0036】[0036]
【表8】 [Table 8]
【0037】本発明の強誘電性液晶組成物には、上記の
化合物以外にも、一般に液晶組成物の基材として用いら
れている各種の化合物、添加剤を加えることにより、そ
の性質を改良することができる。例えば、一般式(VII
I)のような化合物を混合すると、キラルスメクティッ
クC相(Sc*)相の低温域をさらに広げることができる。The properties of the ferroelectric liquid crystal composition of the present invention are improved by adding various compounds and additives generally used as a base material of the liquid crystal composition, in addition to the above compounds. be able to. For example, the general formula (VII
When a compound such as I) is mixed, the low temperature region of the chiral smectic C phase (Sc * ) phase can be further expanded.
【化13】 (上記式中、R19は炭素数1〜18のアルキル基を示
す。)Embedded image (In the above formula, R 19 represents an alkyl group having 1 to 18 carbon atoms.)
【0038】また、本発明の強誘電性液晶組成物に、例
えば特願平8-163671に記載した一般式(IX)に
示すようなコレステリック相(Ch)、キラルスメクティ
ックC相(Sc*)相のねじれを解消する材料を加えると、
配向状態を良好なものにし、コントラストを向上させる
ことができる。In addition, a cholesteric phase (Ch) and a chiral smectic C phase (Sc * ) phase represented by, for example, the general formula (IX) described in Japanese Patent Application No. 8-163671 are added to the ferroelectric liquid crystal composition of the present invention. Add the material that eliminates the twist of
The alignment state can be improved, and the contrast can be improved.
【化14】 (上記式中、R20は炭素数1〜18のアルキル基を示
す。)Embedded image (In the above formula, R 20 represents an alkyl group having 1 to 18 carbon atoms.)
【0039】さらに、例えば、特開平5-88183号
公報に記載されているようなテトラシアノキノジメタン
(TCNQ)等のイオン性物質を少量加えることによって、
しきい値電圧を低減でき、またキノリン等のイオンを取
り込む物質を少量加えることによって体積固有抵抗値を
大きくすることができ、表示安定性を向上させることが
できる。以下、実施例を用いて本発明を具体的に説明す
る。Further, for example, by adding a small amount of an ionic substance such as tetracyanoquinodimethane (TCNQ) described in JP-A-5-88183,
The threshold voltage can be reduced, and the volume specific resistance can be increased by adding a small amount of a substance that takes in ions such as quinoline, so that display stability can be improved. Hereinafter, the present invention will be described specifically with reference to Examples.
【0040】[0040]
(実施例1)表1に記載した化合物の(I-3)13.6
重量部及び(I-5)12.1重量部、表4に記載した化
合物の(II-3)9.1重量部、表5に記載した化合物の
(III-5)19.7重量部、表7に記載した化合物の
(V-5)12.1重量部、表10に記載した化合物α1
2.1重量部、化合物β9.1重量部、化合物γ12.1
重量部を混合してベース液晶組成物を作製した。(Example 1) (I-3) 13.6 of the compounds described in Table 1
Parts by weight and 12.1 parts by weight of (I-5), 9.1 parts by weight of the compound (II-3) described in Table 4, 19.7 parts by weight of (III-5) of the compound described in Table 5, 12.1 parts by weight of (V-5) of the compound described in Table 7 and Compound α1 described in Table 10
2.1 parts by weight, compound 9.1 parts by weight, compound γ12.1
The base liquid crystal composition was prepared by mixing parts by weight.
【0041】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Aを
得た。この液晶組成物Aの降温時の相転移温度(℃)を
表11に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition A of the present invention. Table 11 shows the phase transition temperature (° C.) of the liquid crystal composition A when the temperature was lowered.
【0042】[0042]
【表11】 [Table 11]
【0043】このように、本発明の液晶組成物は、I-Ch
-SA-Sc*-Crの相系列を示すことが確認された。As described above, the liquid crystal composition of the present invention has
It was confirmed to show a phase series of -SA-Sc * -Cr.
【0044】次に、液晶組成物Aをポリイミドを塗布し
たラビング処理済の透明電極付きガラスからなる厚さ2
μmのセルに注入し、Sc*相で電界を印加し、クロスニコ
ルの偏光顕微鏡下で観察したところ、明瞭なスイッチン
グ動作が観測された。また、25℃で10V/μmの矩形
波を印加し、その時の透過光量の変化をフォトダイオー
ドで観察したところ、10%から90%へ変化するのに
要する時間(t10-90)を測定したところ、60μsecで
あった。さらに、32μsecのパルス幅のパルスを印加
したときの25℃でのしきい値電圧が11.5Vで、十分
に低かった。Next, the liquid crystal composition A is made of a rubbed glass having a transparent electrode coated with polyimide and having a thickness of 2 mm.
When injected into a μm cell, an electric field was applied in the Sc * phase, and observed under a crossed Nicols polarizing microscope, a clear switching operation was observed. When a rectangular wave of 10 V / μm was applied at 25 ° C., and the change in the amount of transmitted light at that time was observed with a photodiode, the time required to change from 10% to 90% (t 10-90 ) was measured. However, it was 60 μsec. Furthermore, the threshold voltage at 25 ° C. when a pulse having a pulse width of 32 μsec was applied was 11.5 V, which was sufficiently low.
【0045】(比較例1)実施例1に示すベース液晶組
成物から、化合物(III-5)を抜き、他の化合物の混合
比を同一にしたベース液晶組成物を作製した。Comparative Example 1 From the base liquid crystal composition shown in Example 1, the compound (III-5) was removed, and a base liquid crystal composition having the same mixing ratio of other compounds was prepared.
【0046】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、液晶組成物aを得た。こ
の液晶組成物aの降温時の相転移温度(℃)を表12に
示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition a. Table 12 shows the phase transition temperature (° C.) of the liquid crystal composition a when the temperature was lowered.
【0047】[0047]
【表12】 [Table 12]
【0048】また、実施例1と同様の操作に従い、液晶
組成物aをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、50μsecと速くなったが、実施例1の液晶組成物
Aに対して、TACが44℃に低下した。さらに、32μs
ecのパルス幅のパルスを印加したときの25℃でのしき
い値電圧が、18.8Vとなった。このように実施例1の
液晶組成物Aから一般式(III)で表される化合物成分
を抜くと、TACが低下し、しきい値電圧が高くなること
が分かる。Further, according to the same operation as in Example 1, the liquid crystal composition a was injected into the cell, and the amount of transmitted light was 10% to 90%.
When the time (t 10-90 ) required to change to へ was measured, it was as fast as 50 μsec, but the TAC was lowered to 44 ° C. with respect to the liquid crystal composition A of Example 1. In addition, 32 μs
The threshold voltage at 25 ° C. when a pulse having a pulse width of ec was applied was 18.8 V. Thus, when the compound component represented by the general formula (III) is removed from the liquid crystal composition A of Example 1, the TAC decreases and the threshold voltage increases.
【0049】(実施例2)表Iに示した化合物のうち、
表Iに記載の化合物(I-3)15.3重量部、(I-
5)13.6重量部、表3に記載の化合物(I-35)1
3.6重量部、表4に記載の化合物(II-3)10.2重
量部、表5に記載の化合物(III-5)10.0重量部、
表7に記載の化合物(V-2)10.2重量部、(V-
5)13.6重量部、表8に記載の化合物α13.6重量
部を混合してベース液晶組成物を作製した。Example 2 Among the compounds shown in Table I,
15.3 parts by weight of the compound (I-3) described in Table I,
5) 13.6 parts by weight of compound (I-35) 1 shown in Table 3
3.6 parts by weight, 10.2 parts by weight of the compound (II-3) shown in Table 4, 10.0 parts by weight of the compound (III-5) shown in Table 5
10.2 parts by weight of the compound (V-2) shown in Table 7 and (V-
5) 13.6 parts by weight and 13.6 parts by weight of the compound α shown in Table 8 were mixed to prepare a base liquid crystal composition.
【0050】このベース液晶組成物94.0重量部に対
して、表6に記載の化合物(IV-1)2.0重量部、(IV
-1)4.1重量部を混合して、本発明の液晶組成物Bを
得た。この液晶組成物Bの降温時の相転移温度(℃)を
表13に示す。With respect to 94.0 parts by weight of the base liquid crystal composition, 2.0 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 4.1 parts by weight were mixed to obtain a liquid crystal composition B of the present invention. Table 13 shows the phase transition temperature (° C.) of the liquid crystal composition B when the temperature was lowered.
【0051】[0051]
【表13】 [Table 13]
【0052】このように、本発明の他の例である液晶組
成物Bも、I-Ch-SA-Sc*-Crの相系列を示すことを確認し
た。As described above, it was confirmed that the liquid crystal composition B, which is another example of the present invention, also shows a phase sequence of I-Ch-SA-Sc * -Cr.
【0053】また、実施例1と同様の操作に従い、液晶
組成物Bをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、37μsecであった。さらに、32μsecのパルス幅
のパルスを印加したときの25℃でのしきい値電圧が
7.9Vで、十分に低かった。Further, according to the same operation as in Example 1, the liquid crystal composition B was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to へ was 37 μsec. Further, the threshold voltage at 25 ° C. when a pulse having a pulse width of 32 μsec was applied was 7.9 V, which was sufficiently low.
【0054】(比較例2)実施例2に示すベース液晶組
成物から、化合物(II-3)を抜き、他の化合物の混合
比を同一にしたベース液晶組成物を作製した。Comparative Example 2 Compound (II-3) was removed from the base liquid crystal composition shown in Example 2 to prepare a base liquid crystal composition having the same mixing ratio of other compounds.
【0055】このベース液晶組成物94.0重量部に対
して、表IVに記載の化合物(IV-1)2.0重量部、(IV
-1)4.1重量部を混合して、比較例の液晶組成物bを
得た。この液晶組成物bの降温時の相転移温度(℃)を
表14に示す。Based on 94.0 parts by weight of the base liquid crystal composition, 2.0 parts by weight of the compound (IV-1) shown in Table IV and (IV)
-1) 4.1 parts by weight were mixed to obtain a liquid crystal composition b of a comparative example. Table 14 shows the phase transition temperature (° C.) of the liquid crystal composition b when the temperature was lowered.
【0056】[0056]
【表14】 [Table 14]
【0057】また、実施例1と同様の操作に従い、液晶
組成物bをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、実施例2に対して、40μsecと同程度であった。
しかし、32μsecのパルス幅のパルスを印加したとき
の25℃でのしきい値電圧は、10.9Vとなった。この
ように実施例2の液晶組成物Bから一般式(II)で表さ
れる化合物成分を抜くと、しきい値電圧が高くなること
が分かる。Further, according to the same operation as in Example 1, the liquid crystal composition b was injected into the cell, and the transmitted light amount was 10% to 90%.
The time (t 10-90 ) required to change to へ was measured and was about 40 μsec compared to Example 2.
However, the threshold voltage at 25 ° C. when a pulse having a pulse width of 32 μsec was applied was 10.9 V. Thus, it can be seen that when the compound component represented by the general formula (II) is removed from the liquid crystal composition B of Example 2, the threshold voltage increases.
【0058】(実施例3)表Iに示した化合物のうち、
表1に記載の化合物(I-3)15.3重量部、(I-
5)13.6重量部、(I-35)13.6重量部、表4
に記載の化合物(II-3)10.2重量部、表5に記載の
化合物(III-5)4.9重量部、(III-8)4.9重量
部、表7に記載の化合物(V-2)10.2重量部、(V
-5)13.6重量部、表8に記載した化合物α13.6
重量部を混合してベース液晶組成物を作製した。Example 3 Of the compounds shown in Table I,
15.3 parts by weight of the compound (I-3) shown in Table 1 and (I-
5) 13.6 parts by weight, (I-35) 13.6 parts by weight, Table 4
10.2 parts by weight of the compound (II-3) described in Table 1, 4.9 parts by weight of the compound (III-5) described in Table 5, 4.9 parts by weight of (III-8), and the compound described in Table 7 ( V-2) 10.2 parts by weight, (V
-5) 13.6 parts by weight, compound α13.6 described in Table 8
The base liquid crystal composition was prepared by mixing parts by weight.
【0059】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Cを
得た。この液晶組成物Cの降温時の相転移温度(℃)を
表15に示す。Based on 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition C of the present invention. Table 15 shows the phase transition temperature (° C.) of the liquid crystal composition C when the temperature was lowered.
【0060】[0060]
【表15】 [Table 15]
【0061】このような本発明の液晶組成物も、I-Ch-S
A-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition according to the present invention also has I-Ch-S
It was confirmed to show a phase series of A-Sc * -Cr.
【0062】また、実施例1と同様の操作に従い、液晶
組成物Cをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、38μsecであった。さらに、32μsecのパルス幅
のパルスを印加したときの25℃でのしきい値電圧が
8.6Vで、十分に低かった。Further, according to the same operation as in Example 1, the liquid crystal composition C was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time required to change to (t 10-90 ) was measured and was 38 μsec. Further, the threshold voltage at 25 ° C. when a pulse having a pulse width of 32 μsec was applied was 8.6 V, which was sufficiently low.
【0063】(実施例4)表1に記載の化合物(I-
3)15.9重量部、(I-5)14.1重量部、表3に
記載の化合物(I-35)14.1重量部、表4に記載の
化合物(II-3)10.5重量部、表5に記載の化合物
(III-7)6.5重量部、表7に記載の化合物(V-2)
10.5重量部、(V-5)14.1重量部、表10に記
載の化合物α14.1重量部を混合してベース液晶組成
物を作製した。Example 4 Compounds (I-
3) 15.9 parts by weight, 14.1 parts by weight of (I-5), 14.1 parts by weight of compound (I-35) described in Table 3, and 10.5 parts of compound (II-3) described in Table 4 Parts by weight, 6.5 parts by weight of the compound (III-7) shown in Table 5, and the compound (V-2) shown in Table 7
A base liquid crystal composition was prepared by mixing 10.5 parts by weight, 14.1 parts by weight of (V-5), and 14.1 parts by weight of the compound α shown in Table 10.
【0064】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Dを
得た。この液晶組成物Dの降温時の相転移温度(℃)を
表16に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition D of the present invention. Table 16 shows the phase transition temperature (° C.) of the liquid crystal composition D when the temperature was lowered.
【0065】[0065]
【表16】 [Table 16]
【0066】このような本発明の液晶組成物も、I-Ch-S
A-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition according to the present invention is also provided with I-Ch-S
It was confirmed to show a phase series of A-Sc * -Cr.
【0067】また、実施例1と同様の操作に従い、液晶
組成物Dをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、43μsecであった。さらに、32μsecのパルス幅
のパルスを印加したときの25℃でのしきい値電圧が
7.2Vで、十分に低かった。Further, according to the same operation as in Example 1, the liquid crystal composition D was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to was measured was 43 μsec. Further, the threshold voltage at 25 ° C. when a pulse having a pulse width of 32 μsec was applied was 7.2 V, which was sufficiently low.
【0068】(実施例5)表Iに示した化合物のうち、
表1に記載の化合物(I-3)15.3重量部、(I-
5)13.6重量部、表3に記載の化合物(I-35)1
3.6重量部、表4に記載の化合物(II-12)10.2
重量部、表5に記載の化合物(III-5)10.0重量
部、表7に記載の化合物(V-2)10.2重量部、(V
-5)13.6重量部、表10に記載の化合物α13.6
重量部を混合してベース液晶組成物を作製した。Example 5 Among the compounds shown in Table I,
15.3 parts by weight of the compound (I-3) shown in Table 1 and (I-
5) 13.6 parts by weight of compound (I-35) 1 shown in Table 3
3.6 parts by weight, compound (II-12) 10.2 described in Table 4
Parts by weight, 10.0 parts by weight of the compound (III-5) shown in Table 5, 10.2 parts by weight of the compound (V-2) shown in Table 7,
-5) 13.6 parts by weight, compound α13.6 described in Table 10
The base liquid crystal composition was prepared by mixing parts by weight.
【0069】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Eを
得た。この液晶組成物Eの降温時の相転移温度(℃)を
表17に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition E of the present invention. Table 17 shows the phase transition temperature (° C.) of the liquid crystal composition E when the temperature was lowered.
【0070】[0070]
【表17】 [Table 17]
【0071】このような本発明の液晶組成物も、I-Ch-S
A-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition of the present invention also has the I-Ch-S
It was confirmed to show a phase series of A-Sc * -Cr.
【0072】また、実施例1と同様の操作に従い、液晶
組成物Eをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、46μsecであった。さらに、32μsecのパルス幅
のパルスを印加したときの25℃でのしきい値電圧が
3.4Vで、十分に低かった。Further, according to the same operation as in Example 1, the liquid crystal composition E was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to was measured and found to be 46 μsec. Further, the threshold voltage at 25 ° C. when a pulse having a pulse width of 32 μsec was applied was 3.4 V, which was sufficiently low.
【0073】(実施例6)表1に記載の化合物(I-
9)14.6重量部、(I-13)12.2重量部、表2
に記載した化合物(I-18)13.9重量部、(I-1
9)9.1重量部、(I-21)17.0重量部、表4に
記載の化合物(II-1)9.1重量部、(II-2)9.1重
量部、(II-10)9.1重量部、表5に記載の化合物
(III-6)6.0重量部を混合して、ベース液晶組成物
を作製した。Example 6 Compounds (I-
9) 14.6 parts by weight, (I-13) 12.2 parts by weight, Table 2
13.9 parts by weight of the compound (I-18) described in (I-1)
9) 9.1 parts by weight, (I-21) 17.0 parts by weight, 9.1 parts by weight of compound (II-1) described in Table 4, 9.1 parts by weight of (II-2), (II- 10) 9.1 parts by weight and 6.0 parts by weight of the compound (III-6) shown in Table 5 were mixed to prepare a base liquid crystal composition.
【0074】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Fを
得た。この液晶組成物Fの降温時の相転移温度(℃)を
表18に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition F of the present invention. Table 18 shows the phase transition temperature (° C.) of the liquid crystal composition F when the temperature was lowered.
【0075】[0075]
【表18】 [Table 18]
【0076】このような本発明の液晶組成物も、I-Ch-S
A-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition according to the present invention also has I-Ch-S
It was confirmed to show a phase series of A-Sc * -Cr.
【0077】また、実施例1と同様の操作に従い、液晶
組成物Fをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、52μsecであった。さらに、32μsecのパルス幅
のパルス波を印加したときの25℃でのしきい値電圧が
6.5Vで、十分に低かった。Further, according to the same operation as in Example 1, the liquid crystal composition F was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to was measured was 52 μsec. Furthermore, the threshold voltage at 25 ° C. when a pulse wave having a pulse width of 32 μsec was applied was 6.5 V, which was sufficiently low.
【0078】(実施例7)表1に記載の化合物(I-
9)14.6重量部、(I-13)12.2重量部、表2
に記載の化合物(I-18)13.9重量部、(I-1
9)9.1重量部、(I-21)17.0重量部、表4に
記載の化合物(II-1)9.1重量部、(II-2)9.1重
量部、(II-10)9.1重量部、表5に記載の化合物
(III-5)6.0重量部を混合して、ベース液晶組成物
を作製した。Example 7 Compounds (I-
9) 14.6 parts by weight, (I-13) 12.2 parts by weight, Table 2
13.9 parts by weight of compound (I-18) described in (I-1)
9) 9.1 parts by weight, (I-21) 17.0 parts by weight, 9.1 parts by weight of compound (II-1) described in Table 4, 9.1 parts by weight of (II-2), (II- 10) 9.1 parts by weight and 6.0 parts by weight of the compound (III-5) shown in Table 5 were mixed to prepare a base liquid crystal composition.
【0079】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Gを
得た。この液晶組成物Gの降温時の相転移温度(℃)を
表19に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition G of the present invention. Table 19 shows the phase transition temperature (° C.) of the liquid crystal composition G when the temperature was lowered.
【0080】[0080]
【表19】 [Table 19]
【0081】このような本発明の液晶組成物も、I-Ch-
SA-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition of the present invention also comprises I-Ch-
It was confirmed to show a phase series of SA-Sc * -Cr.
【0082】また、実施例1の項で述べたのと同様の操
作に従い、液晶組成物Gをセルに注入し、透過光量が1
0%から90%へ変化するのに必要な時間(t10-90)
を測定したところ、49μsecであった。さらに、32
μsecのパルス幅のパルス波を印加したときの25℃で
のしきい値電圧が6.0Vで、十分に低かった。Further, according to the same operation as described in the section of Example 1, the liquid crystal composition G was injected into the cell, and the amount of transmitted light was 1
Time required to change from 0% to 90% ( t10-90 )
Was 49 μsec. In addition, 32
The threshold voltage at 25 ° C. when a pulse wave having a pulse width of μsec was applied was 6.0 V, which was sufficiently low.
【0083】(実施例8)表1に記載の化合物(I-
9)14.9重量部、(I-13)12.4重量部、表2
に記載の化合物(I-18)14.2重量部、(I-1
9)9.3重量部、(I-21)17.4重量部、表4に
記載の化合物(II-1)9.3重量部、(II-2)9.3重
量部、(II-10)9.3重量部、表5に記載の化合物
(III-13)4.0重量部を混合して、ベース液晶組成
物を作製した。Example 8 Compounds (I-
9) 14.9 parts by weight, (I-13) 12.4 parts by weight, Table 2
14.2 parts by weight of the compound (I-18) described in (I-1)
9) 9.3 parts by weight, (I-21) 17.4 parts by weight, 9.3 parts by weight of the compound (II-1) described in Table 4, 9.3 parts by weight of (II-2), (II- 10) 9.3 parts by weight and 4.0 parts by weight of the compound (III-13) shown in Table 5 were mixed to prepare a base liquid crystal composition.
【0084】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Hを
得た。この液晶組成物Hの降温時の相転移温度(℃)を
表20に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition H of the present invention. Table 20 shows the phase transition temperature (° C.) of the liquid crystal composition H when the temperature was lowered.
【0085】[0085]
【表20】 [Table 20]
【0086】このような液晶組成物も、I-Ch-SA-Sc*-C
rの相系列を示すことが確認された。[0086] Such a liquid crystal composition is also represented by I-Ch-SA-Sc * -C
It was confirmed to show the phase sequence of r.
【0087】また、実施例1と同様の操作に従い、液晶
組成物Hをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、48μsecであった。さらに、32μsecのパルス幅
のパルスを印加したときの25℃でのしきい値電圧が
5.3Vで、十分に低かった。Further, in accordance with the same operation as in Example 1, the liquid crystal composition H was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to へ was 48 μsec. Further, the threshold voltage at 25 ° C. when a pulse having a pulse width of 32 μsec was applied was 5.3 V, which was sufficiently low.
【0088】(実施例9)表1に記載の化合物(I-
9)14.6重量部、(I-13)12.2重量部、表2
に記載の化合物(I-18)13.9重量部、(I-1
9)9.1重量部、(I-21)17.0重量部、表4に
記載の化合物(II-1)9.1重量部、(II-2)9.1重
量部、(II-10)9.1重量部、表5に記載の化合物
(III-3)6.0重量部を混合して、ベース液晶組成物
を作製した。Example 9 Compounds (I-
9) 14.6 parts by weight, (I-13) 12.2 parts by weight, Table 2
13.9 parts by weight of compound (I-18) described in (I-1)
9) 9.1 parts by weight, (I-21) 17.0 parts by weight, 9.1 parts by weight of compound (II-1) described in Table 4, 9.1 parts by weight of (II-2), (II- 10) 9.1 parts by weight and 6.0 parts by weight of the compound (III-3) shown in Table 5 were mixed to prepare a base liquid crystal composition.
【0089】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Iを
得た。この液晶組成物Iの降温時の相転移温度(℃)を
表21に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition I of the present invention. Table 21 shows the phase transition temperature (° C.) of the liquid crystal composition I when the temperature was lowered.
【0090】[0090]
【表21】 [Table 21]
【0091】このような液晶組成物も、I-Ch-SA-Sc*-C
rの相系列を示すことが確認された。[0091] Such a liquid crystal composition is also represented by I-Ch-SA-Sc * -C
It was confirmed to show the phase sequence of r.
【0092】また、実施例1と同様の操作に従い、液晶
組成物Iをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、48μsecであった。さらに、32μsecのパルス幅
のパルス波を印加したときの25℃でのしきい値電圧が
4.9Vで、十分に低かった。Further, in accordance with the same operation as in Example 1, the liquid crystal composition I was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to へ was 48 μsec. Furthermore, the threshold voltage at 25 ° C. when a pulse wave having a pulse width of 32 μsec was applied was 4.9 V, which was sufficiently low.
【0093】(実施例10)表1に記載の化合物(I-
9)12.9重量部、(I-13)10.8重量部、表2
に記載の化合物(I-18)12.3重量部、(I-1
9)8.0重量部、(I-21)15.0重量部、表4に
記載の化合物(II-1)8.0重量部、(II-2)8.0重
量部、(II-10)8.0重量部、表5に記載の化合物
(III-3)6.0重量部、表7に記載の化合物(V-5)
10.0重量部を混合してベース液晶組成物を作製し
た。Example 10 Compounds (I-
9) 12.9 parts by weight, (I-13) 10.8 parts by weight, Table 2
12.3 parts by weight of the compound (I-18) described in (I-1)
9) 8.0 parts by weight, 15.0 parts by weight of (I-21), 8.0 parts by weight of the compound (II-1) described in Table 4, 8.0 parts by weight of (II-2), (II- 10) 8.0 parts by weight, 6.0 parts by weight of the compound (III-3) described in Table 5, and the compound (V-5) described in Table 7
10.0 parts by weight were mixed to prepare a base liquid crystal composition.
【0094】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Jを
得た。この液晶組成物Jの降温時の相転移温度(℃)を
表22に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition J of the present invention. Table 22 shows the phase transition temperature (° C.) of the liquid crystal composition J when the temperature was lowered.
【0095】[0095]
【表22】 [Table 22]
【0096】このような本発明の液晶組成物も、I-Ch-
SA-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition of the present invention also comprises I-Ch-
It was confirmed to show a phase series of SA-Sc * -Cr.
【0097】また、実施例1と同様の操作に従い、液晶
組成物Jをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、43μsecであった。さらに、32μsecのパルス幅
のパルス波を印加したときの25℃でのしきい値電圧が
4.9Vであり、実施例9に記載の液晶組成物IよりTA
C、応答速度が向上し、しきい値電圧は変わらなかっ
た。Further, according to the same operation as in Example 1, the liquid crystal composition J was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to was measured was 43 μsec. Further, the threshold voltage at 25 ° C. when a pulse wave having a pulse width of 32 μsec was applied was 4.9 V, and the liquid crystal composition I described in Example 9 had a threshold voltage of TA.
C, the response speed improved, and the threshold voltage did not change.
【0098】このように本発明の第1の液晶組成物に対
して、一般式(V)で表される化合物を混合することに
よって、応答速度、しきい値電圧を損ねることなく、キ
ラルスメクチックC(Sc*)相の温度域を広げることが
できるという優れた特性を有している。As described above, by mixing the compound represented by the general formula (V) with the first liquid crystal composition of the present invention, the chiral smectic C can be obtained without impairing the response speed and the threshold voltage. It has an excellent property that the temperature range of the (Sc * ) phase can be expanded.
【0099】(実施例11)表1に記載の化合物(I-
3)13.5重量部、(I-5)12.0重量部、表3に
記載の化合物(I-35)12.0重量部、表4に記載の
化合物(II-3)9.0重量部、表5に記載の化合物(II
I-5)8.8重量部、表7に記載の化合物(V-2)9.
0重量部、(V-5)12.0重量部、表8に記載の化合
物(VI-2)12.0重量部、表10に記載の化合物α1
2.0重量部を混合してベース液晶組成物を作製した。Example 11 Compounds (I-
3) 13.5 parts by weight, 12.0 parts by weight of (I-5), 12.0 parts by weight of compound (I-35) shown in Table 3, and 9.0 of compound (II-3) shown in Table 4 Parts by weight of the compound (II
I-5) 8.8 parts by weight, compound (V-2) described in Table 7 9.
0 parts by weight, 12.0 parts by weight of (V-5), 12.0 parts by weight of compound (VI-2) shown in Table 8, and compound α1 shown in Table 10
2.0 parts by weight were mixed to prepare a base liquid crystal composition.
【0100】このベース液晶組成物94.0重量部に対
して、表6に記載の化合物(IV-1)2.0重量部、(IV
-1)4.1重量部を混合して、本発明の液晶組成物Kを
得た。この液晶組成物Kの降温時の相転移温度(℃)を
表23に示す。With respect to 94.0 parts by weight of the base liquid crystal composition, 2.0 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 4.1 parts by weight were mixed to obtain a liquid crystal composition K of the present invention. Table 23 shows the phase transition temperature (° C.) of the liquid crystal composition K when the temperature was lowered.
【0101】[0101]
【表23】 [Table 23]
【0102】このような本発明の液晶組成物も、I-Ch-
SA-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition of the present invention also comprises I-Ch-
It was confirmed to show a phase series of SA-Sc * -Cr.
【0103】また、実施例1と同様の操作に従い、液晶
組成物Kをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、38μsecであった。さらに、32μsecのパルス幅
のパルスを印加したときの25℃でのしきい値電圧が
6.2Vとなり、実施例2に記載の液晶組成物Bよりしき
い値電圧が低くなった。Further, according to the same operation as in Example 1, the liquid crystal composition K was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time required to change to (t 10-90 ) was measured and was 38 μsec. Further, when a pulse having a pulse width of 32 μsec was applied, the threshold voltage at 25 ° C. was 6.2 V, which was lower than that of the liquid crystal composition B described in Example 2.
【0104】このように、本発明の第2の液晶組成物に
対して一般式(VI)の化合物を加えることによって、応
答速度、しきい値電圧を改善できるとういう優れた特性
を有している。As described above, by adding the compound of the general formula (VI) to the second liquid crystal composition of the present invention, the second liquid crystal composition has an excellent characteristic that the response speed and the threshold voltage can be improved. I have.
【0105】(実施例12)表1に記載の化合物(I-
9)14.1重量部、(I-13)11.8重量部、表2
に記載の化合物(I-18)13.5重量部、(I-1
9)8.8重量部、(I-21)16.5重量部、表4に
記載の化合物(II-1)8.8重量部、(II-2)8.8重
量部、(II-10)8.8重量部、表5に記載の化合物
(III-13)3.8重量部、表9に記載の化合物(VII-
2)5.0重量部を混合して、ベース液晶組成物を作製
した。Example 12 The compounds (I-
9) 14.1 parts by weight, (I-13) 11.8 parts by weight, Table 2
13.5 parts by weight of the compound (I-18) described in (I-1)
9) 8.8 parts by weight, 16.5 parts by weight of (I-21), 8.8 parts by weight of the compound (II-1) described in Table 4, 8.8 parts by weight of (II-2), (II- 10) 8.8 parts by weight, 3.8 parts by weight of the compound (III-13) shown in Table 5, and the compound (VII-
2) 5.0 parts by weight were mixed to prepare a base liquid crystal composition.
【0106】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)2.6重量部、(IV
-1)5.4重量部を混合して、本発明の液晶組成物Lを
得た。この液晶組成物Lの降温時の相転移温度(℃)を
表24に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 2.6 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 5.4 parts by weight were mixed to obtain a liquid crystal composition L of the present invention. Table 24 shows the phase transition temperature (° C.) of the liquid crystal composition L when the temperature was lowered.
【0107】[0107]
【表24】 [Table 24]
【0108】このような本発明の液晶組成物も、I-Ch-
SA-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition of the present invention also comprises I-Ch-
It was confirmed to show a phase series of SA-Sc * -Cr.
【0109】また、実施例1と同様の操作に従い、液晶
組成物Lをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、44μsecであった。さらに、32μsecのパルス幅
のパルス波を印加したときの25℃でのしきい値電圧が
4.4Vとなり、実施例8記載の液晶組成物Hより応答速
度が速く、しきい値電圧が低くなった。Further, according to the same operation as in Example 1, the liquid crystal composition L was injected into the cell, and the transmitted light amount was 10% to 90%.
The time (t 10-90 ) required to change to was measured was 44 μsec. Further, the threshold voltage at 25 ° C. when a pulse wave having a pulse width of 32 μsec was applied was 4.4 V, and the response speed was faster and the threshold voltage was lower than that of the liquid crystal composition H described in Example 8. Was.
【0110】このように、本発明の第1又は第2の液晶
組成物に対して、一般式(VII)の化合物を加えること
によって、さらに応答速度、しきい値電圧を改善できる
という優れた特性を有している。As described above, by adding the compound of the general formula (VII) to the first or second liquid crystal composition of the present invention, an excellent characteristic that the response speed and the threshold voltage can be further improved. have.
【0111】(実施例13)表1に記載の化合物(I-
9)14.6重量部、(I-13)12.2重量部、表2
に記載の化合物(I-18)13.9重量部、(I-1
9)9.1重量部、(I-21)17.0重量部、表4に
記載の化合物(II-1)9.1重量部、(II-2)9.1重
量部、(II-10)9.1重量部、表5に記載の化合物
(III-3)6.0重量部を混合して、ベース液晶組成物
を作製した。(Example 13) Compounds (I-
9) 14.6 parts by weight, (I-13) 12.2 parts by weight, Table 2
13.9 parts by weight of compound (I-18) described in (I-1)
9) 9.1 parts by weight, (I-21) 17.0 parts by weight, 9.1 parts by weight of compound (II-1) described in Table 4, 9.1 parts by weight of (II-2), (II- 10) 9.1 parts by weight and 6.0 parts by weight of the compound (III-3) shown in Table 5 were mixed to prepare a base liquid crystal composition.
【0112】このベース液晶組成物92.0重量部に対
して、表6に記載の化合物(IV-1)4.0重量部、(IV
-1)4.0重量部を混合して、本発明の液晶組成物Mを
得た。この液晶組成物Mの降温時の相転移温度(℃)を
表25に示す。With respect to 92.0 parts by weight of the base liquid crystal composition, 4.0 parts by weight of the compound (IV-1) shown in Table 6 and (IV)
-1) 4.0 parts by weight were mixed to obtain a liquid crystal composition M of the present invention. Table 25 shows the phase transition temperature (° C.) of the liquid crystal composition M when the temperature was lowered.
【0113】[0113]
【表25】 [Table 25]
【0114】このような本発明の液晶組成物も、I-Ch-
SA-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition of the present invention also comprises I-Ch-
It was confirmed to show a phase series of SA-Sc * -Cr.
【0115】また、実施例1と同様の操作に従い、液晶
組成物Mをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、48μsecであった。さらに、32μsecのパルス幅
のパルス波を印加したときの25℃でのしきい値電圧が
5.0Vで、十分に低かった。Further, according to the same operation as in Example 1, the liquid crystal composition M was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to へ was 48 μsec. Further, the threshold voltage at 25 ° C. when a pulse wave having a pulse width of 32 μsec was applied was 5.0 V, which was sufficiently low.
【0116】(実施例14)実施例13記載の液晶組成
物M99.5重量部に対して、テトラシアノキノジメタ
ン(TCNQ)0.5重量部を添加して、本発明の液晶組成
物Nを得た。この液晶組成物Nの降温時の相転移温度
(℃)を表26に示す。(Example 14) To 99.5 parts by weight of the liquid crystal composition M described in Example 13, 0.5 part by weight of tetracyanoquinodimethane (TCNQ) was added to form a liquid crystal composition N of the present invention. I got Table 26 shows the phase transition temperature (° C.) of the liquid crystal composition N when the temperature was lowered.
【0117】[0117]
【表26】 [Table 26]
【0118】このような本発明の液晶組成物は、I-Ch-
SA-Sc*-Crの相系列を示すことが確認された。Such a liquid crystal composition of the present invention has I-Ch-
It was confirmed to show a phase series of SA-Sc * -Cr.
【0119】また、実施例1と同様の操作に従い、液晶
組成物Nをセルに注入し、透過光量が10%から90%
へ変化するのに必要な時間(t10-90)を測定したとこ
ろ、40μsecであった。さらに、32μsecのパルス幅
のパルス波を印加したときの25℃でのしきい値電圧が
4.5Vとなり、実施例13記載の液晶組成物Mより応答
速度が速く、しきい値電圧が低下した。Further, according to the same operation as in Example 1, the liquid crystal composition N was injected into the cell, and the amount of transmitted light was 10% to 90%.
The time (t 10-90 ) required to change to was measured and found to be 40 μsec. Further, the threshold voltage at 25 ° C. when a pulse wave having a pulse width of 32 μsec was applied was 4.5 V, and the response speed was faster than that of the liquid crystal composition M described in Example 13 and the threshold voltage was lowered. .
【0120】このように、TCNQを少量添加することによ
って、応答速度、しきい値電圧をさらに改良することが
できる。Thus, by adding a small amount of TCNQ, the response speed and the threshold voltage can be further improved.
【0121】[0121]
【発明の効果】以上説明してきたように、本発明の強誘
電性液晶組成物は、液相-コレステリック相-スメクチッ
クA相-キラルスメクチックC相の相系列を示し、キラ
ルスメクチックC相を示す温度範囲が広く、かつ高速応
答性、低しきい値電圧という優れた特性を備えている。
従って、本発明の強誘電性液晶組成物は、デイスプレイ
装置、光プリンタ-ヘッド、ライトバルブ等の光スイッ
チング素子用の素材として優れており、極めて有効なも
のである。As described above, the ferroelectric liquid crystal composition of the present invention exhibits a liquid-cholesteric phase-smectic A phase-chiral smectic C phase sequence and a temperature at which the chiral smectic C phase is exhibited. It has excellent characteristics such as a wide range, high-speed response, and low threshold voltage.
Therefore, the ferroelectric liquid crystal composition of the present invention is excellent and extremely effective as a material for an optical switching element such as a display device, an optical printer-head, and a light valve.
【表9】 [Table 9]
【表10】 [Table 10]
───────────────────────────────────────────────────── フロントページの続き (72)発明者 松井 順子 埼玉県戸田市新曽南三丁目17番35号 株式 会社ジャパンエナジ−内 (72)発明者 吉沢 篤 埼玉県戸田市新曽南三丁目17番35号 株式 会社ジャパンエナジ−内 ──────────────────────────────────────────────────の Continuing on the front page (72) Inventor Junko Matsui 3--17-35 Niisonanami, Toda City, Saitama Prefecture Japan Energy Co., Ltd. No. Japan Energy Co., Ltd.
Claims (4)
少なくとも1種と、一般式(II)で表わされる化合物の
少なくとも1種と、一般式(III)で表わされる化合物
の少なくとも1種と、一般式(IV)又は(IV)で表わさ
れる化合物の少なくとも1種とを含有させることを特徴
とする強誘電性液晶組成物。 【化1】 (上記式中、R1は炭素数1〜18のアルキル又はアルコ
キシ基を、R2は炭素数1〜18のアルキル基を表す。) 【化2】 (上記式中、R3は炭素数1〜18のアルキル又はアルコ
キシ基を、R4は炭素数1〜18のアルキル基を表す。) 【化3】 (上記式中、R5は炭素数1〜18のアルキル又はアルコ
キシ基を、R6は炭素数1〜18のアルキル基を、X1は-O
-、-OCO-、-OCOO-を表し、p及びqは0又は1を表す。) 【化4】 (上記式中、Rfは炭素数1又は2のフルオロアルキル基
を表し、R7は炭素数3〜20の直鎖又は分岐鎖アルキル
基を表し、R8、R9及びR10はそれぞれ独立に水素、炭素
数1〜15の直鎖若しくは分岐鎖のアルキル基、炭素数
2〜15のアルケニル基又は炭素数7〜10のアラルキ
ル基を表し、X2は-COO-、-O-又は単結合を表し、X3は-C
OO-、-OCO-、-CH2O-、-OCH2-、-C≡C-又は単結合を表
し、X4は-COO-、-CH2O-又は-O-を表し、X5は-O-又は-OC
O-を表し、C*は不斉炭素を表し、A及びBはそれぞれ独
立にハロゲン、シアノ基、又は含フッ素アルキル基で置
換されていてもよい含六員環を表し、nは0又は1を表
す。)At least one compound represented by the following general formula (I), at least one compound represented by the general formula (II), and at least one compound represented by the general formula (III) And at least one compound represented by the general formula (IV) or (IV). Embedded image (In the above formula, R 1 represents an alkyl or alkoxy group having 1 to 18 carbon atoms, and R 2 represents an alkyl group having 1 to 18 carbon atoms.) (In the above formula, R 3 represents an alkyl or alkoxy group having 1 to 18 carbon atoms, and R 4 represents an alkyl group having 1 to 18 carbon atoms.) (Wherein, R 5 represents an alkyl or alkoxy group having 1 to 18 carbon atoms, R 6 represents an alkyl group having 1 to 18 carbon atoms, and X 1 represents —O
-, -OCO-, -OCOO-, and p and q represent 0 or 1. ) (In the above formula, Rf represents a fluoroalkyl group having 1 or 2 carbon atoms, R 7 represents a linear or branched alkyl group having 3 to 20 carbon atoms, and R 8 , R 9 and R 10 each independently represent Represents hydrogen, a linear or branched alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, and X 2 represents -COO-, -O- or a single bond. And X 3 is -C
OO -, - OCO -, - CH 2 O -, - OCH 2 -, - C≡C- or a single bond, X 4 is -COO -, - CH 2 O- or represents -O-, X 5 Is -O- or -OC
Represents O-, C * represents an asymmetric carbon, A and B each independently represent a halogen-containing, cyano group, or a 6-membered ring optionally substituted by a fluorine-containing alkyl group, and n represents 0 or 1 Represents )
に、下記一般式(V)で表わされる化合物の少なくとも
1種を含有させることを特徴とする強誘電性液晶組成
物。 【化5】 (上記式中、R11は炭素数1〜18のアルキル基を、R12
は炭素数1〜18のアルキル又はアルコキシ基を表
す。)2. A ferroelectric liquid crystal composition according to claim 1, comprising at least one compound represented by the following general formula (V). Embedded image (In the formula, R 11 is an alkyl group having 1 to 18 carbon atoms, R 12
Represents an alkyl or alkoxy group having 1 to 18 carbon atoms. )
晶組成物に、下記一般式(VI)〜(VII)で表される化
合物の少なくとも1種を含有させることを特徴とする強
誘電性液晶組成物。 【化6】 (上記式中、R13、R15、R16及びR18は炭素数1〜18の
アルキル基を、R14及びR17は炭素数1〜18のアルキレ
ン基を表す。)3. The ferroelectric liquid crystal composition according to claim 1 or 2, wherein at least one of the compounds represented by the following general formulas (VI) to (VII) is contained. Ferroelectric liquid crystal composition. Embedded image (In the above formula, R 13 , R 15 , R 16 and R 18 represent an alkyl group having 1 to 18 carbon atoms, and R 14 and R 17 represent an alkylene group having 1 to 18 carbon atoms.)
性液晶組成物を構成要素とする光スイッチング素子。4. An optical switching element comprising the ferroelectric liquid crystal composition according to claim 1 as a component.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16356797A JPH10338878A (en) | 1997-06-06 | 1997-06-06 | Ferroelectric liquid crystal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16356797A JPH10338878A (en) | 1997-06-06 | 1997-06-06 | Ferroelectric liquid crystal composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH10338878A true JPH10338878A (en) | 1998-12-22 |
Family
ID=15776371
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16356797A Pending JPH10338878A (en) | 1997-06-06 | 1997-06-06 | Ferroelectric liquid crystal composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH10338878A (en) |
-
1997
- 1997-06-06 JP JP16356797A patent/JPH10338878A/en active Pending
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