JP3044820B2 - Pyrimidine derivatives and ferroelectric liquid crystal compositions containing the same - Google Patents
Pyrimidine derivatives and ferroelectric liquid crystal compositions containing the sameInfo
- Publication number
- JP3044820B2 JP3044820B2 JP3113097A JP11309791A JP3044820B2 JP 3044820 B2 JP3044820 B2 JP 3044820B2 JP 3113097 A JP3113097 A JP 3113097A JP 11309791 A JP11309791 A JP 11309791A JP 3044820 B2 JP3044820 B2 JP 3044820B2
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- liquid crystal
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- 239000000203 mixture Substances 0.000 title claims description 54
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 title claims description 10
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 105
- 239000004973 liquid crystal related substance Substances 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 description 99
- 230000004044 response Effects 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 11
- 239000004990 Smectic liquid crystal Substances 0.000 description 8
- 230000007704 transition Effects 0.000 description 8
- 230000001747 exhibiting effect Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000004043 responsiveness Effects 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- -1 4-pentenyloxy group Chemical group 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- AYQPVPFZWIQERS-VOTSOKGWSA-N (E)-oct-2-en-1-ol Chemical compound CCCCC\C=C\CO AYQPVPFZWIQERS-VOTSOKGWSA-N 0.000 description 1
- CJGNKCBPRSDDEZ-UHFFFAOYSA-N 2-(4-octylphenyl)pyrimidin-5-ol Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=NC=C(O)C=N1 CJGNKCBPRSDDEZ-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- PEKGRXLJRNPBJA-UHFFFAOYSA-N 5-oct-2-enoxy-2-(4-octylphenyl)pyrimidine Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=NC=C(OCC=CCCCCC)C=N1 PEKGRXLJRNPBJA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- AYQPVPFZWIQERS-UHFFFAOYSA-N cis-2-octen-1-ol Natural products CCCCCC=CCO AYQPVPFZWIQERS-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は電気光学的表示材料とし
て有用な強誘電性液晶材料に関し、更に詳しくは、従来
の液晶材料と比較して配向性、応答性等に優れ、液晶表
示素子の材料として有用な化合物、及び該化合物を含有
する強誘電性液晶組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a ferroelectric liquid crystal material useful as an electro-optical display material, and more particularly, to a liquid crystal display device which is superior in orientation and response to conventional liquid crystal materials. The present invention relates to a compound useful as a material and a ferroelectric liquid crystal composition containing the compound.
【０００２】[0002]
【従来の技術】現在、広く用いられている液晶表示素子
は、主にネマチック液晶を利用したＴＮ（ツイスティッ
ド・ネマチック）型、あるいはＳＴＮ（スーパー・ツイ
スティッド・ネマチック）型と呼ばれるものであり、多
くの利点を有しているものの、その応答性はＣＲＴ等の
発光型の表示方式と比較すると格段に遅いという大きな
欠点を有し、その応用に大きな制限があった。その他の
液晶表示方式も多方面から検討されているが、その応答
性の改善は余りなされていないのが実状である。2. Description of the Related Art At present, liquid crystal display elements widely used are referred to as TN (twisted nematic) type or STN (super twisted nematic) type using mainly nematic liquid crystal. Although it has many advantages, it has a major drawback that its response is much slower than a light-emitting display system such as a CRT, and its application is greatly limited. Although other liquid crystal display systems are being studied from various perspectives, the reality is that little improvement has been made in their responsiveness.
【０００３】ところが、最近見いだされた強誘電性キラ
ルスメクチック液晶を利用した液晶表示素子において
は、従来のＴＮ型などの表示素子の１００倍以上の高速
応答が可能となった。さらに双安定性を有するため、電
源を切っても表示の記憶（メモリー効果）が得られるこ
とが明らかになった。このため、大画面高解像度ディス
プレイ、薄型テレビ、光シャッター、プリンターヘッド
等への利用可能性が大きく、現在、その実用化に向けて
活発に開発研究がなされている。However, a recently discovered liquid crystal display device using a ferroelectric chiral smectic liquid crystal has been able to achieve a high-speed response more than 100 times that of a conventional TN type display device. Further, it has been revealed that the display can be stored (memory effect) even when the power is turned off because of the bistability. Therefore, it is highly applicable to large-screen high-resolution displays, thin-screen televisions, optical shutters, printer heads, and the like. Currently, active research and development is being conducted toward practical use.
【０００４】強誘電性液晶の液晶相は、チルト系のキラ
ルスメクチック相に属するが、その中でも最も低粘性の
キラルスメクチックＣ（以下、ＳＣ*と省略する。）相
が実用上望ましい。既に数多くのＳＣ*相を示す液晶化
合物（以下、ＳＣ*化合物と省略する。）が合成され、
検討されているが、強誘電性液晶表示用光スイッチング
素子として用いるのに、十分な性質を有するものは未だ
知られていない。よって、他の液晶化合物と混合してＳ
Ｃ*相を示す液晶組成物（以下、ＳＣ*液晶組成物と省略
する。）として用いられている。このようなＳＣ*液晶
組成物の検討は活発に行われており、現在では、キラル
でないスメクチックＣ（以下、ＳＣと省略する。）相を
示す母体液晶（以下、ＳＣ母体液晶と省略する。）に、
光学活性化合物から成るキラルドーパントを添加する方
法が一般的である。これによって高速応答性、良好な配
向性、広い作動温度範囲等の特性を合わせ持つＳＣ*液
晶組成物が得られるようになってきた。The liquid crystal phase of the ferroelectric liquid crystal belongs to a tilt type chiral smectic phase. Among them, a chiral smectic C (hereinafter abbreviated as SC * ) phase having the lowest viscosity is preferable. Liquid crystal compounds exhibiting many SC * phases (hereinafter abbreviated as SC * compounds) have already been synthesized,
Although it has been studied, an element having sufficient properties for use as an optical switching element for a ferroelectric liquid crystal display has not yet been known. Therefore, by mixing with other liquid crystal compounds, S
It is used as a liquid crystal composition exhibiting a C * phase (hereinafter abbreviated as SC * liquid crystal composition). Such SC * liquid crystal compositions are being actively studied, and at present, a matrix liquid crystal exhibiting a non-chiral smectic C (hereinafter abbreviated as SC) phase (hereinafter abbreviated as an SC matrix liquid crystal). To
A general method is to add a chiral dopant comprising an optically active compound. As a result, an SC * liquid crystal composition having characteristics such as high-speed response, good alignment, and a wide operating temperature range has been obtained.
【０００５】[0005]
【発明が解決しようとする課題】一般的にＳＣ相を示す
化合物（以下、ＳＣ化合物と省略する。）はＳＣ*化合
物よりも低粘性であるが、充分といえるものは少ない。
現在のところ、ＳＣ母体液晶を構成するＳＣ化合物は、
例えば、一般式（Ａ）Generally, compounds exhibiting the SC phase (hereinafter abbreviated as SC compounds) have a lower viscosity than the SC * compounds, but few are sufficient.
At present, the SC compound constituting the SC matrix liquid crystal is
For example, the general formula (A)
【０００６】[0006]
【化３】 Embedded image
【０００７】（式中、Ｒa及びＲbはアルキル基、アルコ
キシル基、アルコキシカルボニル基、アルカノイルオキ
シ基、又はアルコキシカルボニルオキシ基を表わし、互
いに同一であっても異なっていてもよいが、同時にアル
キル基を表わすことはない。）で表わされる化合物、あ
るいは一般式（Ｂ）Wherein R a and R b represent an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkanoyloxy group or an alkoxycarbonyloxy group, which may be the same or different, but Or a compound represented by the general formula (B):
【０００８】[0008]
【化４】 Embedded image
【０００９】（式中、Ｒa及びＲbは前記一般式（Ａ）に
おけると同じ意味を表わす。）で表わされる化合物が主
に用いられている。これらのうち、一般式（Ａ）で表わ
される化合物は、分子内にエステル結合が存在するた
め、その粘性は比較的高く、これを主成分とするＳＣ母
体液晶を用いた液晶表示素子において、充分な高速応答
を得ることは困難であった。(Wherein, R a and R b have the same meanings as in the general formula (A)). Among these, the compound represented by the general formula (A) has a relatively high viscosity due to the presence of an ester bond in the molecule, which is sufficient for a liquid crystal display device using an SC matrix liquid crystal containing the compound as a main component. It was difficult to obtain a high-speed response.
【００１０】一方、一般式（Ｂ）で表わされる化合物
は、Ｒa、Ｒbの一方がアルキル基、他方がアルコキシル
基である化合物の場合には比較的低粘性であり、特にＲ
aが直鎖状のアルキル基であり、Ｒbが直鎖状又は分岐状
のアルコキシル基である一般式（Ｃ）On the other hand, the compound represented by the general formula (B) has a relatively low viscosity when one of R a and R b is an alkyl group and the other is an alkoxyl group.
a is a linear alkyl group, and R b is a linear or branched alkoxyl group of the general formula (C)
【００１１】[0011]
【化５】 Embedded image
【００１２】（式中、Ｒcは直鎖状のアルキル基を表わ
し、Ｒdは直鎖状又は分岐状のアルキル基を表わす。）
で表わされる化合物は、ＳＣ母体液晶の主成分として、
現在汎用されている。(In the formula, R c represents a linear alkyl group, and R d represents a linear or branched alkyl group.)
Is a main component of the SC matrix liquid crystal,
Currently widely used.
【００１３】しかしながら、この一般式（Ｃ）で表わさ
れる化合物には、ＳＣ相の上限温度があまり高くないと
いう問題点があった。また、一般的に液晶組成物の特性
改善のために、キラルドーパントとして用いる光学活性
化合物、あるいは応答性改善のために粘度降下剤として
用いる減粘液晶等を母体液晶に添加することがあるが、
これによってＳＣ相の上限温度を下げてしまい、ＳＣ相
の温度範囲を狭くする傾向がある。このため、一般式
（Ｃ）で表わされる化合物を主成分とする液晶組成物に
添加した場合、実用上広い温度範囲で使用可能な液晶組
成物を得ることはかなり困難であった。However, the compound represented by the general formula (C) has a problem that the maximum temperature of the SC phase is not so high. In general, to improve the properties of the liquid crystal composition, an optically active compound used as a chiral dopant, or a thinned liquid crystal used as a viscosity-lowering agent for improving responsiveness may be added to the base liquid crystal.
This tends to lower the upper limit temperature of the SC phase and narrow the temperature range of the SC phase. For this reason, when it is added to a liquid crystal composition containing a compound represented by the general formula (C) as a main component, it has been quite difficult to obtain a liquid crystal composition that can be practically used in a wide temperature range.
【００１４】これとは別に、一般的に液晶組成物の温度
範囲を特に高温域に拡大するために、主として３環式化
合物である高温液晶を添加することが知られているが、
この３環式化合物はいずれも粘性が高く、液晶組成物に
添加した場合にその応答性に悪影響を与えてしまう問題
を有している。Apart from this, it is generally known to add a high temperature liquid crystal, which is mainly a tricyclic compound, in order to extend the temperature range of the liquid crystal composition to a particularly high temperature range.
Each of these tricyclic compounds has a high viscosity and has a problem that when added to a liquid crystal composition, the responsiveness is adversely affected.
【００１５】また、一般式（Ｂ）で表わされる化合物に
おいて、Ｒaが直鎖状のアルコキシル基であり、Ｒbが直
鎖状のアルキル基である一般式（Ｄ）In the compound represented by the general formula (B), R a is a linear alkoxyl group and R b is a linear alkyl group.
【００１６】[0016]
【化６】 Embedded image
【００１７】（式中、Ｒe及びＲfは直鎖状のアルキル基
を表わし、互いに同一であっても異なっていてもよ
い。）で表わされる化合物は、その応答性においては一
般式（Ｃ）で表わされる化合物よりもやや優れている。(Wherein R e and R f each represent a linear alkyl group and may be the same or different from each other), and the compound represented by the general formula (C) ) Is slightly better than the compound represented by
【００１８】しかしながら、この一般式（Ｄ）で表わさ
れる化合物は、ＳＣ相の高温域にスメクチックＡ（以
下、ＳＡと省略する。）相を広い温度範囲で有するもの
の、ネマチック（以下、Ｎと省略する。）相は存在しな
いか、あるいはその温度範囲は非常に狭い。従って、こ
のような化合物を主成分として含有するＳＣ母体液晶
も、ＳＣ相の高温域にＳＡ相を有するものの、Ｎ相は存
在しないか、あるいは存在してもその温度範囲は非常に
狭いものであった。However, the compound represented by the general formula (D) has a smectic A (hereinafter abbreviated as SA) phase in a high temperature range of the SC phase in a wide temperature range, but has a nematic (hereinafter abbreviated as N) phase. No phase is present or its temperature range is very narrow. Therefore, an SC matrix liquid crystal containing such a compound as a main component also has an SA phase in a high temperature region of the SC phase, but does not have an N phase or has a very narrow temperature range even if it exists. there were.
【００１９】一方、キラルドーパントとして少量添加し
た場合に充分大きい自発分極を誘起できるような光学活
性化合物、あるいは上記のような減粘液晶などを液晶組
成物に添加すると、液晶組成物のＳＡ相の温度範囲を拡
大し、Ｎ相の温度範囲を狭くするか、あるいは消失させ
る傾向の強いものが多く、それらを添加して得られるＳ
Ｃ*液晶組成物では、ＳＣ*相の高温域にＳＡ相のみを有
し、Ｎ*相を示さないものが多かった。On the other hand, when an optically active compound capable of inducing a sufficiently large spontaneous polarization when added in a small amount as a chiral dopant, or a thinned liquid crystal as described above is added to a liquid crystal composition, the SA phase of the liquid crystal composition is reduced. In many cases, the temperature range is widened and the temperature range of the N phase is narrowed or tends to disappear.
The C * liquid crystal composition having a SA phase only to a high temperature range of SC * phase, in many cases does not exhibit the N * phase.
【００２０】ところが、現在一般的に行われている配向
方法では、ＳＣ*相の高温域にＳＡ相及びＮ*相を示すよ
うな相系列を有し、かつＮ*相における螺旋のピッチが
充分長い場合に良好な配向が得られ、他の相系列の場合
には配向性が劣るのが実状である。However, the orientation method currently generally used has a phase series showing the SA phase and the N * phase in the high temperature region of the SC * phase, and the helical pitch in the N * phase is sufficient. In reality, a good orientation is obtained when the length is long, and the orientation is inferior in the case of another phase series.
【００２１】以上述べたように、一般式（Ｃ）あるいは
一般式（Ｄ）で表わされる化合物を主成分とするＳＣ母
体液晶を用いて、高温域まで広い温度範囲を有し、高速
応答が可能で、かつ配向性に優れた強誘電性ＳＣ*液晶
組成物を得ることはかなり困難であった。As described above, a wide temperature range up to a high temperature range and high-speed response are possible by using an SC matrix liquid crystal containing a compound represented by the general formula (C) or (D) as a main component. However, it was quite difficult to obtain a ferroelectric SC * liquid crystal composition having excellent alignment properties.
【００２２】本発明が解決しようとする課題は、低粘性
で、ＳＣ相の上限温度がより高く、ＳＡ相を示す傾向が
より弱く、Ｎ相を示す傾向がより強い化合物を提供する
ことであり、また、その化合物を含有し、高温域まで広
い温度範囲を有し、高速応答が可能で、かつ配向性に優
れた強誘電性液晶組成物を提供することにある。The problem to be solved by the present invention is to provide a compound having a low viscosity, a higher maximum temperature of the SC phase, a weaker tendency to exhibit the SA phase and a stronger tendency to exhibit the N phase. Another object of the present invention is to provide a ferroelectric liquid crystal composition containing the compound, having a wide temperature range up to a high temperature range, capable of high-speed response, and having excellent orientation.
【００２３】[0023]
【課題を解決するための手段】本発明は上記課題を解決
するために、一般式（Ｉ）According to the present invention, there is provided a compound represented by the general formula (I):
【００２４】[0024]
【化７】 Embedded image
【００２５】（式中、Ｒ1は炭素原子数７〜１２の直鎖
状のアルキル基を表わすが、好ましくは炭素原子数７〜
１０の直鎖状のアルキル基を表わし、Ｒ2は炭素原子数
３〜７の直鎖状のアルキル基を表わすが、好ましくは炭
素原子数３〜５の直鎖状のアルキル基を表わし、また二
重結合はトランス配置を表わす。）で表わされる化合物
を提供する。(In the formula, R 1 represents a straight-chain alkyl group having 7 to 12 carbon atoms, preferably 7 to 12 carbon atoms.)
Represents a linear alkyl group of 10; R 2 represents a linear alkyl group having 3 to 7 carbon atoms, preferably a linear alkyl group having 3 to 5 carbon atoms; The double bond represents the trans configuration. ) Is provided.
【００２６】本発明の一般式（Ｉ）で表わされる化合物
の特徴は、２位に二重結合を有する炭素原子数６〜１０
のアルケニルオキシ基を有する点である。側鎖にアルケ
ニル基あるいはアルケニルオキシ基を有する化合物自体
は既に知られており、例えば、特開昭６１−８３１３６
号公報には、４−ペンテニルオキシ基を有する式The feature of the compound represented by the general formula (I) of the present invention is that the compound having 6 to 10 carbon atoms having a double bond at the 2-position.
Having an alkenyloxy group of Compounds having an alkenyl group or an alkenyloxy group in the side chain are already known, for example, see JP-A-61-83136.
Discloses a compound having a 4-pentenyloxy group.
【００２７】[0027]
【化８】 Embedded image
【００２８】の化合物が示されており、この化合物の相
転移温度は、３６．５℃（Ｃｒ→Ｎ）、５５．９℃（Ｎ
−Ｉ）であった。また、特開昭６１−２９１５３６号公
報にはクロチルオキシ基を有する式The compound has a phase transition temperature of 36.5 ° C. (Cr → N) and 55.9 ° C. (N
-I). JP-A-61-291536 discloses a compound having a crotyloxy group.
【００２９】[0029]
【化９】 Embedded image
【００３０】の化合物が示されており、この化合物の相
転移温度は、５４℃（Ｃｒ→Ｎ）、６１℃（Ｎ−Ｉ）で
あった。これらの化合物は一般式（Ｃ）で表わされる化
合物の類似構造を有し、本発明の一般式（Ｉ）で表わさ
れる化合物とも比較的類似した構造を有しているが、根
本的に異なる点は、これらの化合物はネマチック液晶材
料用として開発されたものであり、側鎖、特にアルケニ
ルオキシ基が短いためにネマチック相のみを示し、ＳＣ
相は示さない点にある。The compound has the phase transition temperature of 54 ° C. (Cr → N) and 61 ° C. (NI). These compounds have a structure similar to that of the compound represented by the general formula (C), and have a structure relatively similar to the compound represented by the general formula (I) of the present invention. These compounds have been developed for nematic liquid crystal materials and exhibit only a nematic phase due to short side chains, especially alkenyloxy groups, and SC
The phases are not shown.
【００３１】一般に、ネマチック液晶化合物の側鎖を長
くしていくと、スメクチック相を発現しやすくなるのは
よく知られたことである。しかしながら、スメクチック
相には前記ＳＡ相からスメクチックＬ（ＳＬ）相まで多
くの相が存在し、その中のどの相を示すか予想すること
は難しく、前記特開昭６１−８３１３６号公報や特開昭
６１−２９１５３６号公報からも予想されるものではな
く、また、このＳＣ化合物を含有するＳＣ*液晶組成物
の優れた効果も予想できるものではない。In general, it is well known that the longer the side chain of a nematic liquid crystal compound, the easier it is to develop a smectic phase. However, there are many phases in the smectic phase from the SA phase to the smectic L (SL) phase, and it is difficult to predict which phase is present, and it is difficult to predict which phase is shown in JP-A-61-83136. It is not expected from JP-A-61-291536, nor is the excellent effect of the SC * liquid crystal composition containing this SC compound expected.
【００３２】本発明の一般式（Ｉ）で表わされる化合物
は、例えば、以下のようにして容易に製造することがで
きる。即ち、一般式（ＩＩＩ）The compound represented by the general formula (I) of the present invention can be easily produced, for example, as follows. That is, the general formula (III)
【００３３】[0033]
【化１０】 Embedded image
【００３４】（式中、Ｒ1は一般式（Ｉ）におけると同
じ意味を表わす。）で表わされる化合物を塩基存在下
に、一般式（ＩＶ）(Wherein R 1 has the same meaning as in formula (I)) in the presence of a base and a compound of formula (IV)
【００３５】[0035]
【化１１】 Embedded image
【００３６】（式中、Ｒ2は一般式（Ｉ）におけると同
じ意味を表わし、二重結合はトランス配置を表わし、Ｘ
は塩素、臭素又はヨウ素を表わす。）で表わされる化合
物と反応させることにより得ることができる。(Wherein R 2 has the same meaning as in formula (I), the double bond represents a trans configuration, and X
Represents chlorine, bromine or iodine. )).
【００３７】ここで一般式（ＩＩＩ）で表わされる化合
物は、一般式（Ｃ）で表わされる化合物の合成中間体と
してよく知られた化合物であり、一般式（ＩＶ）で表わ
される化合物は、対応する一般式（Ｖ）The compound represented by the general formula (III) is a compound well known as a synthetic intermediate of the compound represented by the general formula (C), and the compound represented by the general formula (IV) General formula (V)
【００３８】[0038]
【化１２】 Embedded image
【００３９】（式中、Ｒ2は一般式（Ｉ）におけると同
じ意味を表わし、二重結合はトランス配置を表わす。）
で表わされる化合物をハロゲン化することにより容易に
得ることができる。(Wherein, R 2 has the same meaning as in formula (I), and the double bond represents a trans configuration.)
Can be easily obtained by halogenating the compound represented by
【００４０】ここで、一般式（Ｖ）で表わされる化合物
は、Ｒ2が炭素原子数３〜５のアルキル基である化合物
については市販されており入手が可能である。その他の
化合物についても対応するアルキニルアルコールを半還
元することにより容易に得ることができる。The compound represented by the general formula (V) is commercially available and can be obtained when R 2 is an alkyl group having 3 to 5 carbon atoms. Other compounds can be easily obtained by half-reducing the corresponding alkynyl alcohol.
【００４１】斯くして得られる一般式（Ｉ）で表わされ
る化合物の代表的なものの例を第１表に示す。Table 1 shows typical examples of the compounds represented by the general formula (I) thus obtained.
【００４２】[0042]
【表１】 [Table 1]
【００４３】（表中、Ｃｒは結晶相を、Ｉは等方性液体
相をそれぞれ表わす。）第１表から明らかなように、一
般式（Ｉ）で表わされる化合物は高い温度域までＳＣ相
を示す。また、一般式（Ｄ）で表わされる化合物におい
て、第１表中のNo.1の化合物と側鎖の炭素原子数が等し
い式（ａ）(In the table, Cr represents the crystal phase, and I represents the isotropic liquid phase.) As is clear from Table 1, the compound represented by the general formula (I) shows the SC phase up to a high temperature range. Is shown. In the compound represented by the general formula (D), the compound represented by the formula (a) having the same number of carbon atoms in the side chain as the compound No. 1 in Table 1
【００４４】[0044]
【化１３】 Embedded image
【００４５】の化合物の相転移温度は、３８．７℃（Ｃ
ｒ→ＳＣ）、５７．５℃（ＳＣ−ＳＡ）、８３．４℃
（ＳＡ−Ｉ）であった。このように、式（ａ）の化合物
ではＳＡ相の温度範囲が約２６℃と広いのに対して、第
１表中のＮｏ．１の化合物では、約１１℃と狭くなって
おり、ＳＡ相を狭くする傾向が強くなっていることがわ
かる。また、ＳＣ相の上限温度は式（ａ）の化合物では
５７．５℃であるのに対し、第１表中のＮｏ．１の化合
物では６９．４℃と約１２℃も上昇しており、これは液
晶組成物を調製する上で、非常に好ましい性質である。The phase transition temperature of the compound was 38.7 ° C. (C
r → SC), 57.5 ° C. (SC-SA), 83.4 ° C.
(SA-I). As described above, in the compound of the formula (a), the temperature range of the SA phase is as wide as about 26 ° C. In the case of the compound No. 1, it is as narrow as about 11 ° C., which indicates that the tendency to narrow the SA phase is strong. The maximum temperature of the SC phase is 57.5 ° C. for the compound of the formula (a), whereas the maximum temperature of the compound of formula (a) is No. 1 in Table 1. In the case of the compound (1), the temperature rose to 69.4 ° C., which is about 12 ° C., which is a very preferable property in preparing a liquid crystal composition.
【００４６】本発明は、また、一般式（Ｉ）で表わされ
る化合物を含有する液晶組成物を提供する。本発明の液
晶組成物は、（１）一般式（Ｉ）で表わされる化合物の
少なくとも１種を含有するＳＣ相を示す母体液晶及び
（２）光学活性化合物から成るキラルドーパントを含有
するＳＣ*液晶組成物であり、特に等方性液体（Ｉ）相
からの冷却時に、Ｎ*相及びＳＡ相を経てＳＣ*相に相転
移する相系列を有するものであり、配向性に優れ、また
広い温度範囲で使用可能で、低粘性の液晶組成物であ
る。 本発明の一般式（Ｉ）で表わされる化合物は、そ
のものが低粘性であり、ＳＣ相の上限温度が高く、ＳＡ
相を狭くする傾向が強いといった性質を有するため、こ
の化合物を含有する液晶組成物に、ＳＡ相を拡大し、Ｎ
相を消失させる傾向を示すキラルドーパントや減粘液晶
化合物を添加しても、上記のような優れた特性を示す液
晶組成物を容易に調製することができる。The present invention also provides a liquid crystal composition containing the compound represented by the general formula (I). The liquid crystal composition of the present invention comprises (1) a host liquid crystal exhibiting an SC phase containing at least one compound represented by the general formula (I) and (2) an SC * liquid crystal containing a chiral dopant composed of an optically active compound. A composition having a phase sequence that undergoes a phase transition to an SC * phase via an N * phase and an SA phase, particularly when cooled from an isotropic liquid (I) phase, has excellent orientation, and has a wide temperature range. It is a liquid crystal composition that can be used in a range and has low viscosity. The compound represented by the general formula (I) of the present invention has a low viscosity itself, a high maximum temperature of the SC phase, and a high SA.
Since the compound has the property of having a strong tendency to narrow the phase, the liquid crystal composition containing this compound expands the SA phase,
Even when a chiral dopant or a thinned liquid crystal compound which tends to lose a phase is added, a liquid crystal composition exhibiting the above-described excellent characteristics can be easily prepared.
【００４７】このような優れた特性を充分に示すために
は、本発明の一般式（Ｉ）で表わされる化合物を、ＳＣ
母体液晶中に５重量％以上含有することが好ましい。ま
た、液晶組成物の融点を降下させて、温度範囲を低温域
に拡大するためには、液晶分子の骨格や側鎖の形状の異
なった他種のＳＣ化合物を加える必要があるので、一般
式（Ｉ）で表わされる化合物の含有量は、５〜５０重量
％の範囲であることが好ましい。In order to sufficiently exhibit such excellent properties, the compound represented by the general formula (I) of the present invention must be
The content is preferably 5% by weight or more in the base liquid crystal. In addition, in order to lower the melting point of the liquid crystal composition and expand the temperature range to a lower temperature range, it is necessary to add another type of SC compound having a different skeleton or side chain shape of the liquid crystal molecule. The content of the compound represented by (I) is preferably in the range of 5 to 50% by weight.
【００４８】本発明の一般式（Ｉ）で表わされる化合物
とともに母体液晶の構成成分として用いるのに適当なＳ
Ｃ化合物としては、前述の一般式（Ｃ）と同様の骨格を
有する一般式（ＩＩ）The compound of formula (I) of the present invention together with the compound represented by the formula (I)
As the C compound, a compound represented by the general formula (II) having a skeleton similar to that of the aforementioned general formula (C)
【００４９】[0049]
【化１４】 Embedded image
【００５０】（式中、Ｒ3は炭素原子数６〜１２の直鎖
状のアルキル基を表わし、Ｒ4は炭素原子数６〜１２の
直鎖状又は分岐状のアルキル基、又は直鎖状のアルケニ
ル基を表わす。）で表わされる化合物が特に好適であ
る。(Wherein, R 3 represents a linear alkyl group having 6 to 12 carbon atoms, and R 4 represents a linear or branched alkyl group having 6 to 12 carbon atoms, or a linear alkyl group having 6 to 12 carbon atoms. The compound represented by the following formula: is particularly preferred.
【００５１】ここで、一般式（ＩＩ）で表わされる化合
物の代表的なものの例を、第２表及び第３表に示す。Here, typical examples of the compound represented by the general formula (II) are shown in Tables 2 and 3.
【００５２】[0052]
【表２】 [Table 2]
【００５３】[0053]
【表３】 [Table 3]
【００５４】この一般式（ＩＩ）で表わされる化合物及
び本発明の一般式（Ｉ）で表わされる化合物を含有する
ＳＣ*液晶組成物もまた、等方性液体（Ｉ）相からの冷
却時に、Ｎ*相及びＳＡ相を経てＳＣ*相に相転移する相
系列を有し、配向性に優れ、広い温度範囲で使用可能
で、低粘性の液晶組成物である。The SC * liquid crystal composition containing the compound represented by the general formula (II) and the compound represented by the general formula (I) of the present invention also shows the following properties upon cooling from the isotropic liquid (I) phase: The liquid crystal composition has a phase sequence of undergoing a phase transition to an SC * phase through an N * phase and an SA phase, has excellent orientation, can be used in a wide temperature range, and has a low viscosity.
【００５５】一般式（Ｉ）及び一般式（ＩＩ）で表わさ
れる化合物を含有する母体液晶の応答性を改善するため
に添加することができる減粘液晶としては、一般式
（Ｅ）As the viscosity-reduced liquid crystal which can be added to improve the responsiveness of the base liquid crystal containing the compounds represented by the general formulas (I) and (II), the general formula (E)
【００５６】[0056]
【化１５】 Embedded image
【００５７】（式中、Ｒe及びＲfは一般式（Ｄ）におけ
ると同じ意味を表わし、シクロヘキサン環はトランス配
置である。）で表わされる化合物や、一般式（Ｆ）Wherein R e and R f have the same meanings as in the general formula (D), and the cyclohexane ring has a trans configuration, and the compound represented by the general formula (F)
【００５８】[0058]
【化１６】 Embedded image
【００５９】（式中、Ｒe及びＲfは一般式（Ｄ）におけ
ると同じ意味を表わす。）で表わされる化合物をあげる
ことができる。後述の実施例にも示すように、一般式
（Ｉ）で表わされる化合物及び一般式（ＩＩ）で表わさ
れる化合物を含有するＳＣ母体液晶（Ｈ−１）を調製し
た。(Wherein, R e and R f have the same meanings as in formula (D)). As shown in the examples described below, SC parent liquid crystals (H-1) containing the compound represented by the general formula (I) and the compound represented by the general formula (II) were prepared.
【００６０】なお、ＳＣ母体液晶（Ｈ−１）は、The SC base liquid crystal (H-1)
【００６１】[0061]
【化１７】 Embedded image
【００６２】から成るものである。このＳＣ母体液晶
（Ｈ−１）８４重量％、及び式（Ｐ）[0062] 84% by weight of the SC base liquid crystal (H-1) and the formula (P)
【００６３】[0063]
【化１８】 Embedded image
【００６４】（式中、Ｐｒはプロピル基を表わす。）の
化合物から成るキラルドーパント１６重量％から成るＳ
Ｃ*液晶組成物（Ｍ−１）は、６７℃以下でＳＣ*相を示
し、７１．５℃以下でＳＡ相を示し、７６℃以下でＮ*
相を示し、それ以上の温度で等方性液体（Ｉ）相となっ
た。(Wherein Pr represents a propyl group).
The C * liquid crystal composition (M-1) exhibits an SC * phase at 67 ° C or lower, an SA phase at 71.5 ° C or lower, and an N * at 76 ° C or lower .
Phase above which it became an isotropic liquid (I) phase.
【００６５】このＳＣ*液晶組成物（Ｍ−１）の室温に
おける電気光学的応答速度は３６μ秒と非常に高速であ
った。また、ＳＣ母体液晶（Ｈ−１）において、一般式
（Ｉ）で表わされる化合物に代えて、一般式（Ｄ）で表
わされる化合物を用い、同様の組成比でＳＣ母体液晶
（Ｈ−２）を調製した。このＳＣ母体液晶（Ｈ−２）
は、The electro-optical response speed of this SC * liquid crystal composition (M-1) at room temperature was as high as 36 μsec. In the SC parent liquid crystal (H-1), a compound represented by the general formula (D) is used in place of the compound represented by the general formula (I), and the SC parent liquid crystal (H-2) Was prepared. This SC matrix liquid crystal (H-2)
Is
【００６６】[0066]
【化１９】 Embedded image
【００６７】から成るものである。ＳＣ母体液晶（Ｈ−
２）８４重量％、及び上記の組成のキラルドーパント１
６重量％から成るＳＣ*液晶組成物（Ｍ−２）を調製し
たところ、６６℃以下でＳＣ*相を示し、７２．５℃以
下でＳＡ相を示し、７５．５℃以下でＮ*相を示した。
また、電気光学的応答速度は５２μ秒であった。Is composed of SC matrix liquid crystal (H-
2) 84% by weight and chiral dopant 1 having the above composition
When an SC * liquid crystal composition (M-2) consisting of 6% by weight was prepared, an SC * phase was shown at 66 ° C or lower, an SA phase was shown at 72.5 ° C or lower, and an N * phase was shown at 75.5 ° C or lower. showed that.
The electro-optical response speed was 52 μsec.
【００６８】このように、一般式（Ｄ）で表わされる化
合物に代えて、一般式（Ｉ）で表わされる化合物をＳＣ
母体液晶中にわずか１０重量％含有することにより、Ｓ
Ｃ*相の上限温度は１℃高くなり、ＳＡ相の温度範囲は
２℃狭くなり、Ｎ*相の温度範囲は１．５℃拡大するこ
とができた。Thus, instead of the compound represented by the general formula (D), the compound represented by the general formula (I)
By containing only 10% by weight in the base liquid crystal, S
The upper limit temperature of the C * phase was raised by 1 ° C., the temperature range of the SA phase was narrowed by 2 ° C., and the temperature range of the N * phase could be expanded by 1.5 ° C.
【００６９】このことから、一般式（Ｉ）で表わされる
化合物を含有する液晶組成物は、ＳＡ相を示す傾向が強
く、Ｎ相を消失させる傾向にあるキラルドーパントを、
あるいは上記一般式（Ｅ）あるいは一般式（Ｆ）で表わ
される減粘液晶を添加しても、Ｉ−Ｎ*−ＳＡ−ＳＣ*相
の好ましい相系列と、広い温度範囲かつ高い上限温度を
有することが理解できる。From the above, the liquid crystal composition containing the compound represented by the general formula (I) has a strong tendency to show an SA phase and a chiral dopant which tends to eliminate an N phase.
Alternatively, even when the thinned liquid crystal represented by the general formula (E) or the general formula (F) is added, a preferable phase series of an IN * -SA-SC * phase and a wide temperature range and a high maximum temperature are obtained. I can understand.
【００７０】また、一般式（Ｉ）で表わされる化合物
は、一般式（Ｄ）で表わされる化合物より粘性が低いの
で、その応答性は格段に改善され、非常に効果のあるこ
とが理解できる。Further, since the compound represented by the general formula (I) has lower viscosity than the compound represented by the general formula (D), it can be understood that the responsiveness is remarkably improved and is very effective.
【００７１】[0071]
【実施例】以下に実施例をあげて本発明を具体的に説明
するが、本発明の主旨および適用範囲はこれらの実施例
によって制限されるものではない。EXAMPLES The present invention will be described in detail below with reference to examples, but the gist and scope of the present invention are not limited by these examples.
【００７２】本実施例において、相転移温度の測定は温
度調節ステージを備えた偏光顕微鏡及び示差走査熱量計
（ＤＳＣ）を併用して行った。また、組成物中における
「％」はすべて「重量％」を表わすものとする。In this example, the measurement of the phase transition temperature was carried out by using a polarizing microscope equipped with a temperature control stage and a differential scanning calorimeter (DSC). In addition, all “%” in the composition represent “% by weight”.
【００７３】また、化合物の構造は核磁気共鳴スペクト
ル（ＮＭＲ）及び赤外吸収スペクトル（ＩＲ）により確
認した。なお、ＮＭＲにおけるＣＤＣｌ3は溶媒を表わ
し、ｓは一重線を、ｄは二重線を、ｔは三重線を、ｍは
多重線を表わす。また、ＩＲにおけるＮｕｊｏｌは流動
パラフィン中の懸濁状態における測定を表わす。 （実施例１） ２−（４−オクチルフェニル）−５−
（２−オクテニルオキシ）ピリミジン（第１表中のNo.1
の化合物）の合成 ２−（４−オクチルフェニル）−５−ヒドロキシピリミ
ジン１００ｍｇを、Ｎ，Ｎ−ジメチルホルムアミド（Ｄ
ＭＦ）１０ｍｌに溶解した。この溶液に室温でｔ−ブト
キシカリウム４１ｍｇを加え、３０分間攪拌した。この
混合物に、２−オクテノールより合成した１−ブロモ−
２−オクテン７０ｍｇをＤＭＦ２ｍｌに溶解して、この
溶液を室温で５分間で滴下し、さらに６時間攪拌した。
反応終了後、エーテルを加え、有機層を希塩酸、水、次
いで飽和食塩水で洗滌し、無水硫酸ナトリウムで乾燥し
た後、溶媒を留去して、粗生成物１０２ｇを得た。この
粗生成物をカラムクロマトグラフィー（シリカゲル、ヘ
キサン／酢酸エチル＝１０／１）を用いて精製して、２
−（４−オクチルフェニル）−５−（２−オクテニルオ
キシ）ピリミジンの白色結晶８５ｇを得た。さらにこれ
をエタノールから再結晶させて、精製物を得た。この精
製物の相転移温度を第１表に示した。The structure of the compound was confirmed by a nuclear magnetic resonance spectrum (NMR) and an infrared absorption spectrum (IR). CDCl 3 in NMR represents a solvent, s represents a singlet, d represents a doublet, t represents a triplet, and m represents a multiplet. Nujol in IR represents measurement in a suspended state in liquid paraffin. (Example 1) 2- (4-octylphenyl) -5
(2-octenyloxy) pyrimidine (No. 1 in Table 1)
Synthesis of 2- (4-octylphenyl) -5-hydroxypyrimidine in 100 mg of N, N-dimethylformamide (D
MF) dissolved in 10 ml. To this solution, 41 mg of potassium t-butoxide was added at room temperature, and the mixture was stirred for 30 minutes. 1-bromo-synthesized from 2-octenol was added to this mixture.
70 mg of 2-octene was dissolved in 2 ml of DMF, and this solution was added dropwise at room temperature for 5 minutes, and further stirred for 6 hours.
After completion of the reaction, ether was added, the organic layer was washed with dilute hydrochloric acid, water, and then with saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off to obtain 102 g of a crude product. This crude product was purified by column chromatography (silica gel, hexane / ethyl acetate = 10/1) to give 2
85 g of white crystals of-(4-octylphenyl) -5- (2-octenyloxy) pyrimidine were obtained. This was further recrystallized from ethanol to obtain a purified product. Table 1 shows the phase transition temperature of this purified product.
【００７４】また、ＮＭＲ及びＩＲで測定した結果は、
以下の通りであった。 ＮＭＲ（ＣＤＣｌ3）：δ＝０．８６（ｔ，６Ｈ）、
１．０７−１．８７（ｍ，１８Ｈ）、１．８７−２．２
３（ｍ，２Ｈ）、２．６３（ｔ，２Ｈ）、４．５６
（ｄ，２Ｈ）、５．４７−６．１０（ｍ，２Ｈ）、７．
２６（ｄ，２Ｈ）、８．４３（ｓ，２Ｈ） ＩＲ（Ｎｕｊｏｌ）：１５８０、１５５０、１２８０、
１０００、９７０、９２０、８５０、７９０ｃｍ-1 （実施例２〜４）実施例１と同様にして、第１表中のＮ
ｏ．２〜Ｎｏ．４の化合物を合成した。各化合物の相転
移温度は第１表に示した。 （実施例５） ＳＣ*液晶組成物の調製 第１表中のＮｏ．１の化合物、及び一般式（ＩＩ）で表
わされる化合物を含有する以下の組成のＳＣ母体液晶
（Ｈ−１）を調製した。The results measured by NMR and IR are as follows:
It was as follows. NMR (CDCl 3 ): δ = 0.86 (t, 6H),
1.07-1.87 (m, 18H), 1.87-2.2
3 (m, 2H), 2.63 (t, 2H), 4.56
(D, 2H), 5.47-6.10 (m, 2H), 7.
26 (d, 2H), 8.43 (s, 2H) IR (Nujol): 1580, 1550, 1280,
1000, 970, 920, 850, 790 cm -1 (Examples 2 to 4) In the same manner as in Example 1, N
o. 2-No. Compound 4 was synthesized. The phase transition temperature of each compound is shown in Table 1. (Example 5) SC * Preparation of liquid crystal composition An SC parent liquid crystal (H-1) containing the compound of Formula 1 and the compound represented by the general formula (II) and having the following composition was prepared.
【００７５】[0075]
【化２０】 Embedded image
【００７６】次に、この母体液晶（Ｈ−１）８４％、及
び以下の組成のキラルドーパント（Ｐ）Next, 84% of the base liquid crystal (H-1) and a chiral dopant (P) having the following composition
【００７７】[0077]
【化２１】 Embedded image
【００７８】１６％から成るＳＣ*液晶組成物（Ｍ−
１）を調製した。この液晶組成物は６７℃以下でＳＣ*
相を示し、７１．５℃以下でＳＡ相を示し、７６．０℃
以下でＮ*相を示した。 （比較例１）ＳＣ母体液晶（Ｈ−１）において、一般式
（Ｉ）の化合物に代えて一般式（Ｄ）の化合物を同量用
いたＳＣ母体液晶（Ｈ−２）SC * liquid crystal composition (M-
1) was prepared. This liquid crystal composition has a SC *
71.5 ° C. or less, showing SA phase at 71.5 ° C.
The N * phase is shown below. (Comparative Example 1) SC mother liquid crystal (H-2) using the same amount of the compound of general formula (D) in place of the compound of general formula (I) in SC mother liquid crystal (H-1)
【００７９】[0079]
【化２２】 Embedded image
【００８０】を調製した。このＳＣ母体液晶（Ｈ−２）
８４％、及びキラルドーパント（Ｐ）１６％から成るＳ
Ｃ*液晶組成物（Ｍ−２）を調製した。この液晶組成物
は６６℃以下でＳＣ*相を示し、７２．５℃以下でＳＡ
相を示し、７５．５℃以下でＮ*相を示した。 （実施例６） 液晶表示素子の作成 まず、ＩＴＯ蒸着ガラス板（電極面積７０mm2）にポリ
イミド形成溶液を塗布し、ポリイミド被膜を作成した
（基板Ａ）。同様にして、グラスファイバーのスペーサ
ーを混合した上記のポリイミド形成溶液を用いてスペー
サーを含んだポリイミド被膜を作成した（基板Ｂ）。基
板Ａ及び基板Ｂをナイロン布でラビング処理を施した。
一方の基板に熱硬化型エポキシ接着剤を塗布して、基板
Ａ及び基板Ｂをそのラビング方向が互いに平行かつ逆向
きになるように重ね合わせ、加熱硬化させ、セルを作成
した。Was prepared. This SC matrix liquid crystal (H-2)
S consisting of 84% and 16% of a chiral dopant (P)
A C * liquid crystal composition (M-2) was prepared. This liquid crystal composition exhibited an SC * phase at 66 ° C. or lower, and exhibited an SA * phase at 72.5 ° C. or lower.
Phase and showed an N * phase below 75.5 ° C. Example 6 Preparation of Liquid Crystal Display Element First, a polyimide forming solution was applied to an ITO vapor-deposited glass plate (electrode area: 70 mm 2 ) to form a polyimide film (substrate A). Similarly, a polyimide coating containing spacers was prepared using the above-mentioned polyimide forming solution mixed with glass fiber spacers (substrate B). The substrate A and the substrate B were rubbed with a nylon cloth.
A thermosetting epoxy adhesive was applied to one of the substrates, the substrates A and B were overlapped so that their rubbing directions were parallel and opposite to each other, and were heated and cured to form a cell.
【００８１】こうして得られたセルに、実施例１で得ら
れたＳＣ＊液晶組成物（Ｍ−１）を加熱して等方性液体
（Ｉ）相とした状態で注入し、次いで徐冷を行い、Ｎ*
相、ＳＡ相、ついでＳＣ*相を配向させ、液晶表示素子
を得た。配向状態は非常に良好であった。このセルのセ
ル厚を測定したところ、約２．０μｍであった。The SC * liquid crystal composition (M-1) obtained in Example 1 was injected into the cell thus obtained in a state where the SC * liquid crystal composition (M-1) was converted into an isotropic liquid (I) phase, and then slowly cooled. Done, N *
The phase, SA phase, and then SC * phase were oriented to obtain a liquid crystal display device. The orientation state was very good. When the cell thickness of this cell was measured, it was about 2.0 μm.
【００８２】このセルに電界強度１０Ｖp-p／μｍの矩
形波を印加してその電気光学的応答速度を測定したとこ
ろ、２５℃で３６μ秒と高速応答を確認できた。このと
きの自発分極は１５．５ｎＣ／ｃｍ2、チルト角は２
８．６゜であった。コントラストは非常に良好であっ
た。 （比較例２）実施例６と同様にして作成したセルに、比
較例１で得られたＳＣ*液晶組成物（Ｍ−２）を用い
て、同様にして液晶表示素子を作成した。When a rectangular wave having an electric field strength of 10 V pp / μm was applied to this cell and its electro-optical response speed was measured, a high-speed response of 36 μsec at 25 ° C. was confirmed. The spontaneous polarization at this time was 15.5 nC / cm 2 , and the tilt angle was 2
It was 8.6 ゜. The contrast was very good. (Comparative Example 2) A liquid crystal display device was formed in the same manner as in Example 6, except that the SC * liquid crystal composition (M-2) obtained in Comparative Example 1 was used.
【００８３】実施例６と同様にして測定した電気光学的
応答速度は、２５℃で５２μ秒であり、ＳＣ*液晶組成
物（Ｍ−１）を用いた場合に比べて遅くなった。また、
このときの自発分極は１５．３ｎＣ／ｃｍ2であり、チ
ルト角は２６．２゜であった。（実施例７）以下の組成
から成るＳＣ母体液晶（Ｈ−３）を調製した。The electro-optical response speed measured in the same manner as in Example 6 was 52 μsec at 25 ° C., which was lower than that in the case where the SC * liquid crystal composition (M-1) was used. Also,
At this time, the spontaneous polarization was 15.3 nC / cm 2 , and the tilt angle was 26.2 °. Example 7 An SC matrix liquid crystal (H-3) having the following composition was prepared.
【００８４】[0084]
【化２３】 Embedded image
【００８５】この液晶組成物は６７．０℃以下でＳＣ相
を、７３．５℃以下でＳＡ相を、８５．５℃以下でＮ相
を示した。またその融点は約−２３℃であった。このＳ
Ｃ母体液晶（Ｈ−３）９０％、及びＳＡ相を拡大させ、
Ｎ相を消失させる傾向を有する一般式（Ｑ）The liquid crystal composition exhibited an SC phase at 67.0 ° C. or lower, an SA phase at 73.5 ° C. or lower, and an N phase at 85.5 ° C. or lower. Its melting point was about -23 ° C. This S
90% of C-base liquid crystal (H-3) and SA phase are expanded,
General formula (Q) having a tendency to eliminate the N phase
【００８６】[0086]
【化２４】 Embedded image
【００８７】の化合物１０％から成るＳＣ*液晶組成物
（Ｍ−３）を調製した。この液晶組成物は６３．５℃以
下でＳＣ*相を、７５．５℃以下でＳＡ相を、７７．０
℃以下でＮ*相を示した。またその融点は−２５℃以下
であった。An SC * liquid crystal composition (M-3) consisting of 10% of the above compound was prepared. This liquid crystal composition has an SC * phase at 63.5 ° C. or lower, an SA phase at 75.5 ° C. or lower, and 77.0 ° C.
It showed an N * phase below ℃. Its melting point was -25 ° C or lower.
【００８８】実施例６と同様にして、液晶表示素子を作
成し、その電気光学的応答速度を測定したところ、２５
℃で３０μ秒と非常に高速であった。また、その配向性
は非常に良好であり、コントラストも良好であった。A liquid crystal display device was prepared in the same manner as in Example 6, and its electro-optical response speed was measured.
It was very fast at 30 ° C. at 30 ° C. The orientation was very good, and the contrast was also good.
【００８９】[0089]
【発明の効果】本発明の一般式（Ｉ）で表わされる化合
物を含有する強誘電性液晶組成物は、広い温度範囲でＳ
Ｃ*相を示し、室温で５０μ秒以下という高速応答が可
能である。According to the present invention, the ferroelectric liquid crystal composition containing the compound represented by the general formula (I) can be used in a wide temperature range.
It shows a C * phase, and a high-speed response of 50 μsec or less at room temperature is possible.
【００９０】また、配向性に優れ、良好なコントラスト
を得ることができ、表示用光スイッチング素子の材料と
して極めて有用である。Further, it has excellent orientation and can obtain good contrast, and is extremely useful as a material for a light switching element for display.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C07D 239/34 C09K 19/34 C09K 19/42 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────の Continued on the front page (58) Field surveyed (Int. Cl. 7 , DB name) C07D 239/34 C09K 19/34 C09K 19/42 CA (STN) REGISTRY (STN)
Claims (4)
基を表わし、Ｒ2は炭素原子数３〜７の直鎖状のアルキ
ル基を表わし、二重結合はトランス配置を表わす。）で
表わされる化合物。1. A compound of the general formula (I) (Wherein, R 1 represents a linear alkyl group having 7 to 12 carbon atoms, R 2 represents a linear alkyl group having 3 to 7 carbon atoms, and the double bond represents a trans configuration. )).
を含有する母体液晶及び（２）光学活性化合物から成る
キラルドーパントを含有する強誘電性液晶組成物。2. A ferroelectric liquid crystal composition comprising (1) a base liquid crystal containing a compound represented by the general formula (I) and (2) a chiral dopant comprising an optically active compound.
基を表わし、Ｒ4は炭素原子数６〜１２の直鎖状又は分
岐状のアルキル基、又は直鎖状のアルケニル基を表わ
す。）で表わされる化合物を含有することを特徴とする
請求項２記載の強誘電性液晶組成物。3. A compound of the general formula (II) (Wherein, R 3 represents a linear alkyl group having 6 to 12 carbon atoms, and R 4 represents a linear or branched alkyl group having 6 to 12 carbon atoms, or a linear alkenyl group) The ferroelectric liquid crystal composition according to claim 2, comprising a compound represented by the following formula:
物を構成要素とする液晶表示素子。4. A liquid crystal display device comprising the ferroelectric liquid crystal composition according to claim 2 as a constituent element.
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|---|---|---|---|
| JP3113097A JP3044820B2 (en) | 1991-05-17 | 1991-05-17 | Pyrimidine derivatives and ferroelectric liquid crystal compositions containing the same |
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|---|---|---|---|
| JP3113097A JP3044820B2 (en) | 1991-05-17 | 1991-05-17 | Pyrimidine derivatives and ferroelectric liquid crystal compositions containing the same |
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| JPH04342572A JPH04342572A (en) | 1992-11-30 |
| JP3044820B2 true JP3044820B2 (en) | 2000-05-22 |
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