JPH02110189A - Chiral smectic liquid crystal composition - Google Patents
Chiral smectic liquid crystal compositionInfo
- Publication number
- JPH02110189A JPH02110189A JP1052466A JP5246689A JPH02110189A JP H02110189 A JPH02110189 A JP H02110189A JP 1052466 A JP1052466 A JP 1052466A JP 5246689 A JP5246689 A JP 5246689A JP H02110189 A JPH02110189 A JP H02110189A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- smectic
- phase
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 239000004990 Smectic liquid crystal Substances 0.000 title claims description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 47
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 10
- -1 malonic acid ester Chemical class 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 230000004044 response Effects 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 description 2
- 102100022096 Acid-sensing ion channel 5 Human genes 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 101000901085 Homo sapiens Acid-sensing ion channel 5 Proteins 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- QRAZRBGYBYIGRL-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)phenol Chemical compound C1CC(CCCCC)CCC1C1=CC=C(O)C=C1 QRAZRBGYBYIGRL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 101100247628 Mus musculus Rcl1 gene Proteins 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical group C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical group C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 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
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- UVCBPUQNMGFVAA-UHFFFAOYSA-N dimethyl 2-butylpropanedioate Chemical compound CCCCC(C(=O)OC)C(=O)OC UVCBPUQNMGFVAA-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006284 nylon film Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000008334 thiadiazines Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（イ）産業上の利用分野
この発明はカイラルスメクチックＣ相を呈する液晶組成
物に関する。さらに詳しくは、大容量や広視角の表示に
適した強誘電性液晶表示に用いるカイラルスメクチック
Ｃ相を呈する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (a) Industrial Application Field This invention relates to a liquid crystal composition exhibiting a chiral smectic C phase. More specifically, the present invention relates to a liquid crystal composition exhibiting a chiral smectic C phase for use in ferroelectric liquid crystal displays suitable for large capacity and wide viewing angle displays.
（ロ）従来の技術
現任液晶表示素子では液晶のネマチック相を利用したも
のが主流を占めているが、近年ではこれに加えてスメク
チック相を利用した種々の表示モードの研究も盛んに行
われている。特にカイラルなスメクチックＣ相を利用し
た強誘電性液晶による液晶表示は大容量表示が可能な点
及び視角が広い点から有望視されている。(b) Conventional technology The mainstream of current liquid crystal display devices is those that utilize the nematic phase of liquid crystal, but in recent years, in addition to this, research has been actively conducted on various display modes that utilize the smectic phase. There is. In particular, a liquid crystal display using a ferroelectric liquid crystal using a chiral smectic C phase is considered to be promising because it can display a large capacity and has a wide viewing angle.
（ハ）発明が解決しようとする課題
しかし、強誘電性液晶表示の場合通常のＴＮ（Ｔｗｉｓ
ｔｅｄ Ｎｅｍａｔｉｃ）表示と異なりスメクチックＣ
相でのメモリー特性を利用するため、表示容量が増すに
つれて応答速度の向上が必要となる。例えば、１画面を
１／８０ｓｅｃで書き換え、■ラインの書き換えに４つ
のパルスを印加する駆動法を用いると、応答速度τで表
示可能なライン数りとの関係は、 ４ Ｘ ｒ Ｘ Ｌ
＝ ｌ／６０ｓｅｃとなり、ライン数の多い大容量液
晶表示素子に適用するためには、液晶に著しく高い応答
速度が要求される。(c) Problems to be solved by the invention However, in the case of ferroelectric liquid crystal displays, ordinary TN (Twis)
ted Nematic) Unlike the display, smectic C
Since the memory characteristics of the phase are used, as the display capacity increases, the response speed needs to be improved. For example, if one screen is rewritten in 1/80 sec and a driving method is used in which four pulses are applied to rewrite lines, the relationship between the response speed τ and the number of lines that can be displayed is 4 X r X L
= l/60 sec, and in order to apply it to a large-capacity liquid crystal display element with a large number of lines, the liquid crystal is required to have an extremely high response speed.
従って、従来強誘電性液晶表示に用いる液晶として、ネ
マチック液晶の場合と同様に液晶に望まれる種々の条件
を満足するよう摸数の化合物を混合した液晶組成物が用
いられるが、現時点では未だ応答速度の点で十分満足の
ゆくものは得られていない。Therefore, as in the case of nematic liquid crystals, conventional liquid crystal compositions are used as liquid crystals for ferroelectric liquid crystal displays, in which a large number of compounds are mixed in order to satisfy the various conditions desired for liquid crystals. Not enough speed has been achieved.
また、強誘電性液晶表示に用いる液晶組成物に望まれる
性質は上に述べたような高速応答性の他に次のようなも
のがある。まず当然の事ながら室温付近でスメクチック
Ｃ相を示すことが必要である。また、良好な液晶の配向
を得るためにｒＡＣ（ｉｓｏｔｒｏｐｉｃ−ｓｍｅｃｔ
ｉｃＡ−ｓｍｅｃｔ １ｃｃ）又はＩＮＡＣ（ｉｓｏ
ｔｒｏｐｉｃ−ｎｅｍａＬｉｃ−ｓｍｅｃｔｉｃ人−ｓ
ｍｅｃｔｉｃｃ）相系列を液晶組成物が示すことが望ま
しい。In addition to the above-mentioned high-speed response, desirable properties of a liquid crystal composition used in a ferroelectric liquid crystal display include the following. First of all, as a matter of course, it is necessary to exhibit a smectic C phase near room temperature. In addition, in order to obtain good liquid crystal alignment, rAC (isotropic-smect
icA-smect 1cc) or INAC (iso
tropic-nemaLic-smectic person-s
It is desirable that the liquid crystal composition exhibits a mecticc phase series.
この発明は、かかる状況下なされたものであり、ことに
、応答速度が高いカイラルスメクチック液晶組成物を提
供しようとするものであり、さらに常温付近でスメクチ
ックＣ相を示し所望の液晶相系列を示すスメクチック液
晶組成物を提供しようとするものである。The present invention was made under such circumstances, and particularly aims to provide a chiral smectic liquid crystal composition that has a high response speed, and further exhibits a smectic C phase at around room temperature and exhibits a desired liquid crystal phase series. The present invention aims to provide a smectic liquid crystal composition.
（ニ）課題を解決するための手段
この発明の発明者らは、上記観点から鋭意研究を行なっ
た結果、スメクチックＣ相を呈する液晶化合物中に、式
（Ａ）で示される化合物を少量添加することにより、高
速応答性を示すと共に、先に述べたような強誘電性液晶
表示に用いる液晶組成物に望まれる性質を満足するカイ
ラルスメクチック液晶組成物を得ることができる事実を
見出し、この発明に到達した。(d) Means for Solving the Problems As a result of intensive research from the above viewpoint, the inventors of this invention added a small amount of the compound represented by formula (A) to a liquid crystal compound exhibiting a smectic C phase. We have discovered that by doing so, it is possible to obtain a chiral smectic liquid crystal composition that not only exhibits high-speed response but also satisfies the properties desired for a liquid crystal composition used in a ferroelectric liquid crystal display as described above, and based on this invention. Reached.
かくしてこの発明によれば、スメクチックＣ相を呈する
液晶化合物に、下式（Ａ）：
（式中、Ｒ，とＲ２は、同−又は異なって、直鎖状又は
分岐状で炭素数１〜１２のアルキル基を示す。Thus, according to the present invention, a liquid crystal compound exhibiting a smectic C phase has the following formula (A): represents an alkyl group.
＊はそのＣが光学活性炭素原子であることを示す）で表
わされる化合物の少なくとも１種を添加してなるカイラ
ルスメクチック液晶組成物が提供される。A chiral smectic liquid crystal composition containing at least one compound represented by *indicates that C is an optically active carbon atom is provided.
この発明で用いる上記式（Ａ）化合物はそれ自体文献未
記載の新規化合物である。The compound of formula (A) used in this invention is itself a novel compound that has not been described in any literature.
なお、式（Ａ）ならびに後述の式中で使用する用語、“
直鎖状又は分枝状で炭素数１〜Ｌ２のアルキル基”とは
、メチル、エチル、プロピル、ｉ−プロピル、ブチル、
ｉ−ブチル、ｔ−ブチル、ペンチル、２−メチルブチル
、２．２−ジメチルプロピル、ヘキシル、２又は３−メ
チルペンチル、２．２−ジメチルブチル、４−メチルブ
チル、６−メチルオクチル、ｎ−ヘプチル、２，２−ジ
メチルペンチル、３．３−ジメチルペンチル、２，４−
ジメチルペンチル、ｎ−オクチル、２．２．３．３−テ
トラメチルブチル、ノニル、デシル、ウンデシル、ドデ
シルなどが含まれる。これらのアルキル基中で炭素鎖に
不斉炭素が含まれていてもよい。Note that the terms used in formula (A) and the formulas described below, “
"Light chain or branched alkyl group having 1 to L2 carbon atoms" refers to methyl, ethyl, propyl, i-propyl, butyl,
i-butyl, t-butyl, pentyl, 2-methylbutyl, 2.2-dimethylpropyl, hexyl, 2 or 3-methylpentyl, 2.2-dimethylbutyl, 4-methylbutyl, 6-methyloctyl, n-heptyl, 2,2-dimethylpentyl, 3,3-dimethylpentyl, 2,4-
Dimethylpentyl, n-octyl, 2.2.3.3-tetramethylbutyl, nonyl, decyl, undecyl, dodecyl, and the like. The carbon chain of these alkyl groups may contain an asymmetric carbon.
また、“直鎖状又は分岐状で炭素数１〜１２のアルコキ
シ基”とは、上記のアルキル基で置換されたアルコキシ
基が含まれる。さらに、アルコキシカルボニル基は、こ
のようなアルコキシ基が結合したカルボニル基が含まれ
る。なお、式（Ａ）の化合物には、シス体とトランス体
とがあるが、いずれもこの発明に用いることができる。Furthermore, the term "linear or branched alkoxy group having 1 to 12 carbon atoms" includes an alkoxy group substituted with the above alkyl group. Furthermore, the alkoxycarbonyl group includes a carbonyl group to which such an alkoxy group is bonded. The compound of formula (A) has a cis form and a trans form, both of which can be used in the present invention.
式（Ａ）の化合物は、例えば、光学活性エピクロルヒド
リンとフェノール類を塩基の存在下で反応させて式（■
）：
（上式中、Ｒ，とＲ１は、式（Ａ）中の定義と同一の意
味を示しＲ７はメチル、エチルなどの低級アルキル基を
示す）のマロン酸エステルを塩基の存在下反応すること
により得ろことができる。The compound of formula (A) can be prepared, for example, by reacting optically active epichlorohydrin and phenols in the presence of a base to obtain the compound of formula (■
): (In the above formula, R, and R1 have the same meaning as defined in formula (A), and R7 represents a lower alkyl group such as methyl or ethyl) is reacted with a malonic acid ester in the presence of a base. You can gain a lot by doing this.
この発明におけるスメクチックＣ相を呈する液晶化合物
としては、当該分野で知られた種々のスメクチック液晶
を用いることができる。その具体例としては、下式＜ｍ
＞、ＣＪ）及び（Ｖ）で示される化合物が挙げられる。As the liquid crystal compound exhibiting the smectic C phase in this invention, various smectic liquid crystals known in the art can be used. As a specific example, the following formula <m
>, CJ) and (V).
Ｒ２−ＣＨ（ＣＯＯＲ７）ｓ
・・・・・・（ｎ）
（式中、Ａ及びＢは、それぞれ、単結合又は−ＣＯＯ−
１−ＯＣＯ−１−ＣＨ＝ＣＨ−ＣＯＯ−１−０ＣＯ−Ｃ
Ｈ＝ＣＨ−１−〇−１−Ｓ−１−ｏｃｏｏ〜もしくは−
Ｃ〇−の基を示す。Ｄ及びＥはそれぞれ、単結合又は−
ＣＯＯ−１−０ＣＯ−１−ＣＨ＝Ｎ−１Ｎ−ＣＨ−１−
ＣＩ（＝ＣＨ−１−Ｃ＝Ｃ−１−ＣＨ＝ＣＨ（−ＣＯＯ
−１−０ＣＯ−ＣＨ・Ｃｌ−１−ＣＨ，ＣＨ，−１−０
ＣＨ，−、−ＣＨ，０−１−ＣＯＳ−らしくは−ＳＣ〇
−の基を示す。R2-CH(COOR7)s ......(n) (wherein A and B are each a single bond or -COO-
1-OCO-1-CH=CH-COO-1-0CO-C
H=CH-1-〇-1-S-1-ocoo~or-
Indicates C〇- group. D and E are each a single bond or -
COO-1-0CO-1-CH=N-1N-CH-1-
CI(=CH-1-C=C-1-CH=CH(-COO
-1-0CO-CH・Cl-1-CH,CH,-1-0
CH,-, -CH,0-1-COS--like represents a -SC〇- group.
■、■およ依すよ、それぞれ独立して、ベンゼン環、ピ
リジン環、ピリミジン環、ピラジン環、ピリダジン環、
ピペラジン環、シクロヘキサン環、ビラン環、ジオキサ
シクロヘキサン環、チアピラン環、ノヂアン環、チアジ
アジン環、ビシクロ［２，２，２］オクタン環、テトラ
ジン環等の六員環を示し、これらの六員環中の水素原子
は、フッ素原子、塩素原子、臭素原子、シアノ基、ニト
ロ基、低級アルキル基、低級アルコキシ基又は重水素（
Ｄ）で置換されていてもよい。Ｒ８及びＲ，はそれぞれ
独立して、直鎖状又は分岐状で炭素数１〜１２のアルキ
ルもしくはアルコキン基を示す。ｐは１又は２の整数を
示す。）
もちろん、これらは２種以上混合して用いることができ
る。■、■It depends, each independently a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring,
Indicates a six-membered ring such as a piperazine ring, a cyclohexane ring, a biran ring, a dioxacyclohexane ring, a thiapyran ring, a nodian ring, a thiadiazine ring, a bicyclo[2,2,2]octane ring, and a tetrazine ring. The hydrogen atom is a fluorine atom, chlorine atom, bromine atom, cyano group, nitro group, lower alkyl group, lower alkoxy group, or deuterium (
D) may be substituted. R8 and R each independently represent a linear or branched alkyl or alkokyne group having 1 to 12 carbon atoms. p represents an integer of 1 or 2. ) Of course, two or more of these can be used in combination.
上記のようなスメクチック液晶化合物のうち、下式（Ｂ
）：
（式中、Ｒ１は直鎖状又は分岐状で炭素数１〜１２のア
ルキル基又はアルコキシ基、Ｒ４は直鎖状又は分枝状で
炭素数１〜１２のアルキル基を示す）の化合物は分子軸
に垂直な方向に双極子モーメントを持っているため、得
られるカイラルスメクチック液晶組成物の熱安定性を向
上し、スメクチックＣ相の温度安定性を充分に確保する
ので好ましい。Among the above smectic liquid crystal compounds, the following formula (B
): (wherein R1 is a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, R4 is a linear or branched alkyl group having 1 to 12 carbon atoms) has a dipole moment in the direction perpendicular to the molecular axis, which improves the thermal stability of the obtained chiral smectic liquid crystal composition and sufficiently ensures the temperature stability of the smectic C phase, which is preferable.
さらに式（Ｂ）の化合物と、下式（Ｃ）：（式中、Ｒ１
は直鎖状又は分岐状で炭素数１〜１２のアルキル基又は
アルコキン基、Ｒ６は直鎖状又は分枝状で炭素数１〜１
２のアルコキシ基又はそのアルコキシ基を育するアルコ
キシカルボニル基を示し、Ｘは−ＣＯＯ−１−〇Ｃ〇−
又は単結合を示す。ｍとｎはそれぞれ１又は２の整数で
ある）で表わされる化合物の１１．又は２種以上とを組
合せたスメクチック液晶化合物を用いた場合には、上記
した熱安定性の点がさらに向上すると共に、室温でスメ
クチックＣ相を呈するカイラルスメクチック液晶組成物
が得られるのでより好ましい。この際の式（Ｂ）と（Ｃ
）の化合物の混合比は、通常［０：１〜【：３（重量比
）とするのが適している。Furthermore, a compound of formula (B) and the following formula (C): (wherein R1
is a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, and R6 is a linear or branched alkyl group or alkyl group having 1 to 12 carbon atoms.
2 represents an alkoxy group or an alkoxycarbonyl group that grows the alkoxy group, and X is -COO-1-〇C〇-
Or indicates a single bond. 11. of the compound represented by m and n are each an integer of 1 or 2). Alternatively, it is more preferable to use a smectic liquid crystal compound in combination of two or more types, since the above-mentioned thermal stability is further improved and a chiral smectic liquid crystal composition exhibiting a smectic C phase at room temperature can be obtained. In this case, formula (B) and (C
) The mixing ratio of the compounds (weight ratio) is usually [0:1 to [:3 (weight ratio)].
スメクチックＣ相を呈する液晶化合物に前記した式（Ａ
）の光学活性化合物を混合することにより、この発明の
カイラルスメクチック液晶組成物が得られる。この際の
式（Ａ）の化合物の混合量は、液晶組成物中、０．５〜
２０重量％とするのが適しており、１〜１０重量％とす
るのが好ましい。０．５重量％未満では、スメクチック
液晶化合物の応答性の向上効果が不充分であり、２０重
量％を越えるとスメクチックＣＦｇの熱安定性が不充分
となる点で適さない。A liquid crystal compound exhibiting a smectic C phase has the formula (A
) The chiral smectic liquid crystal composition of the present invention can be obtained by mixing the optically active compounds. At this time, the amount of the compound of formula (A) mixed in the liquid crystal composition is from 0.5 to
A suitable amount is 20% by weight, preferably 1 to 10% by weight. If it is less than 0.5% by weight, the effect of improving the responsiveness of the smectic liquid crystal compound is insufficient, and if it exceeds 20% by weight, the thermal stability of the smectic CFg becomes insufficient, which is not suitable.
なお、この発明のカイラルスメクチック液晶組成物中に
は、ピッチ調整用カイラル化合物、大きなＰｓを有する
化合物等の種々の添加剤が、この発明の効果が阻害され
ない限り、含有されていてもよい。The chiral smectic liquid crystal composition of the present invention may contain various additives such as a pitch-adjusting chiral compound and a compound having a large Ps, as long as the effects of the present invention are not impaired.
（ホ）作用
式（Ａ）の化合物は２つの光学活性炭素を有し、これら
の光学活性炭素が剛直な５員環構造の中に組み込まれて
いるため、分子の自由回転を抑制する事ができ、スメク
チック相を呈する液晶化合物と混合すれば液晶組成物と
しての自発分極が増加し応答速度は大きく向上するもの
と考えられる。(e) The compound of the working formula (A) has two optically active carbons, and these optically active carbons are incorporated into a rigid five-membered ring structure, so the free rotation of the molecule can be suppressed. It is thought that if it is mixed with a liquid crystal compound exhibiting a smectic phase, the spontaneous polarization of the liquid crystal composition will increase and the response speed will be greatly improved.
そして組合せるスメクチック液晶化合物や混合割合を選
択することにより室温付近でスメクチックＣ相を呈し、
またＩＡＣやＩＮＡＣ等の相系列を有する応答速度の速
い液晶組成物が得られることとなる。By selecting the smectic liquid crystal compounds to be combined and the mixing ratio, a smectic C phase is exhibited near room temperature.
Moreover, a liquid crystal composition having a phase series such as IAC or INAC and having a fast response speed can be obtained.
（以下余白）
（へ）実施例
以下実施例により本発明のカイラルスメクチックＣ相を
何する液晶組成物につき詳細に説明するが、これにより
この発明は限定されるものではない。(The following is a blank space) (F) Examples A liquid crystal composition having a chiral smectic C phase according to the present invention will be explained in detail by Examples, but the present invention is not limited thereby.
なお、以下の各実施例において、本発明の光学活性化合
物（Ａ）のＲ，Ｓ表示は下記の化学式の位置番号に基づ
いて行った。In addition, in each of the following Examples, R and S of the optically active compound (A) of the present invention were indicated based on the position number of the following chemical formula.
ベンジルトリエチルアンモニウムクロリド００４ｇとの
混合物を６０℃で撹拌させながら水酸化ナトリウム水溶
液（ＮａＯＨＯ，４５９、水１５村）を２０分かけて滴
下し、さらに１時間還流を行った。反応溶液を室温まで
冷却し、エーテル抽出を２回行い、飽和食塩水で１回洗
浄して減圧上溶媒を留去した。While stirring the mixture with 004 g of benzyltriethylammonium chloride at 60° C., an aqueous sodium hydroxide solution (NaOHO, 459, water: 15 mm) was added dropwise over 20 minutes, and the mixture was further refluxed for 1 hour. The reaction solution was cooled to room temperature, extracted with ether twice, washed once with saturated brine, and the solvent was distilled off under reduced pressure.
残渣をシリカゲルクロマトグラフィで精製し、下記化学
式（八゛）で示される（Ｓ）−２，３−エポキシプロビ
ル−４−（トランス−４−ｎ−ペンチルシクロヘキシル
）フェニルエーテル１．８９を得た。The residue was purified by silica gel chromatography to obtain 1.89 of (S)-2,3-epoxypropyl-4-(trans-4-n-pentylcyclohexyl)phenyl ether represented by the following chemical formula (8).
実施例１−ユ
Ｒ−（−）−エピクロルヒドリン（化学純度９８．５％
以上、光学純度９９％以上） ５．５５９と、下記化学
式で示される４−（トランス−４−ｎ−ペンチルシクロ
ヘキシル）フェノール２，４６９、
この化合物（Ａ′）の物理的特性を下記に示す。Example 1 - UR-(-)-epichlorohydrin (chemical purity 98.5%
(optical purity of 99% or more) 5.559 and 4-(trans-4-n-pentylcyclohexyl)phenol 2,469 represented by the following chemical formula. The physical properties of this compound (A') are shown below.
［α］Ｐ ＋４．４４’ （ｃ＝１．３６． ＣＩ
（２Ｃ１ｔ）（以下余白）
ＮＭＲ（ＣＤＣ１３）
δ： ０．４５〜２．５０ （２１Ｈ，ｍ）２．５０〜
３．００ （２Ｈ，ｌ１１）３．１５”３．５０ （Ｌ
Ｈ，ｍ）
３．７０〜４．３０ （２Ｈ，ｍ）
６．７９ （２Ｈ，ｄ、 Ｊ＝９．０Ｈｚ）
７．０９ （２Ｈ，ｄ、 Ｊ ＝９．０Ｈｚ
）次に、鉱油で懸濁させた５０重量％水素化ナトリウム
２２４＊ｇを乾燥エーテルで２回洗浄後、乾燥テトラヒ
ドロフランＬＯｘＱを加えた。この懸濁液を４０℃で撹
拌しなからｎ−ブチルマロン酸ジメチル１３゜ｚｇを滴
下して５分間撹拌した後、上記で得られた（ Ｓ ）−
２，３−エポキシプロピル−４−（トランス−４−ｎ−
ペンチルシクロヘキシル）フェニルエーテル（Ａ’）１
．４１ｇを滴下し、２０時間還流撹拌した。反応液を室
温に戻してから４Ｎ塩酸をＩ）Ｈ＝１になるまで滴下し
た後、エーテル抽出を２回行い、飽和食塩水で１回洗浄
して減圧上溶媒を留去した。残渣をシリカゲルクロマト
グラフィで分離精製し、下記化学式で示される光学活性
化合物、（２Ｓ、４Ｓ）体（ＡＩ）及び（２Ｒ，４Ｓ）
体（Ａ、）のγ−ラクトン誘導体をそれぞれ５０ｍｇ及
び４０靭を得た。[α]P +4.44' (c=1.36. CI
(2C1t) (blank below) NMR (CDC13) δ: 0.45~2.50 (21H, m) 2.50~
3.00 (2H, l11) 3.15"3.50 (L
H, m) 3.70-4.30 (2H, m) 6.79 (2H, d, J=9.0Hz)
7.09 (2H, d, J = 9.0Hz
) Next, 224*g of 50% by weight sodium hydride suspended in mineral oil was washed twice with dry ether, and then dry tetrahydrofuran LOxQ was added. While stirring this suspension at 40°C, 13゜g of dimethyl n-butylmalonate was added dropwise, and after stirring for 5 minutes, the above-obtained (S)-
2,3-epoxypropyl-4-(trans-4-n-
Pentylcyclohexyl) phenyl ether (A') 1
．． 41 g was added dropwise and stirred under reflux for 20 hours. After returning the reaction solution to room temperature, 4N hydrochloric acid was added dropwise until I)H=1, followed by ether extraction twice, washing once with saturated brine, and the solvent was distilled off under reduced pressure. The residue was separated and purified by silica gel chromatography to obtain optically active compounds represented by the following chemical formulas, (2S,4S) body (AI) and (2R,4S) body.
50 mg and 40 g of the γ-lactone derivative of body (A,) were obtained, respectively.
光学活性化合物、（２Ｓ、４Ｓ）体の化学式、物理的特
性及び元素分析結果を下記に示す。The optically active compound, the chemical formula, physical properties, and elemental analysis results of the (2S, 4S) body are shown below.
相転移温度： Ｃ−一→Ｉ
ＣａＥ＆’ ＋３３．４５° （ｃ ＝０．６５８．
ＣＨｔＣ！、）Ｎ Ｍ Ｒ（ＣＤ Ｃｌ ３ ）
δ： ０．８８〜１．９８ （３０Ｈ，ｍ）２．３８〜
２．６７ （３Ｈ，ｍ）
４．０７〜４．１３ （２Ｈ，ｍ）
４．６７〜４．７３ （ＬＨ，ｉ）
６．８３ （２Ｈ，ｄ、 Ｊ ＝８．３Ｈｚ）７
．１２ （２Ｈ，ｄ、 Ｊ＝８．３Ｈｚ）Ｉ Ｒ
（ＫＢｒ） １７６２ｃｍ−（以下余白）
元素分ＦＲ（ＣｔｓＨｉｏＯｓとして）Ｈ
理論値（％）７７．９５ １０．０？実測ＩＣ％）
７７．９１ １０．１２光学活性化合物、（２Ｒ，
４Ｓ）体の化学式及び物理的特性を下記に示す。Phase transition temperature: C-1 → I CaE&' +33.45° (c = 0.658.
CHtC! ,)NMR(CDCl3)δ: 0.88~1.98 (30H, m)2.38~
2.67 (3H, m) 4.07~4.13 (2H, m) 4.67~4.73 (LH, i) 6.83 (2H, d, J = 8.3Hz) 7
．． 12 (2H, d, J=8.3Hz) I R
(KBr) 1762cm- (blank below) Elemental content FR (as CtsHioOs) H Theoretical value (%) 77.95 10.0? Actual IC%)
77.91 10.12 Optically active compound, (2R,
The chemical formula and physical properties of the 4S) body are shown below.
相転移温度ＩＣ−１
［ｆｆ ］Ｐ ＋ ２０．３７° （、Ｃ＝１．０５
． ＣＩ（、Ｃ１りＮＭＲ（ＣＤＣＩ、）
δ： ０．７０〜２．９５ （３３Ｈ，１ｌｌ）４．０
０〜４．２５ （２Ｈ，ｉ）
４．５０〜４．９５ （ＬＨ，ｍ）
６．７７ （２Ｈ，ｄ、 Ｊ＝８．４Ｈｚ）
？、Ｌｌ （２Ｈ，ｄ、 Ｊ＝１１．４Ｈｚ
）Ｉ Ｒ（Ｋ Ｂ ｒ） １７６２ｃｍ−実施例
１−ｂ
５０％水素化ナトリウム１６３ｍ９の乾燥１．２−ジメ
トキシエタン懸濁液に、ジメチル−ｎ−へブチルマロネ
ート７１６１９の１．２−ジメトキシエタン溶液を加え
、撹拌下に５分間反応させた後、（Ｓ）−２，３−エポ
キシプロピル−４−（トランス−４〜ｎ−ベンチルンク
ロヘキシル）フェニルエーテル９４Ｑｘｇの１．２−ジ
メトキシエタン溶液を加え、２時間半加熱撹拌した。Phase transition temperature IC-1 [ff]P + 20.37° (, C=1.05
．． CI (, C1 NMR (CDCI,) δ: 0.70-2.95 (33H, 1ll) 4.0
0~4.25 (2H, i) 4.50~4.95 (LH, m) 6.77 (2H, d, J=8.4Hz)
? , Ll (2H, d, J=11.4Hz
) I R(K B r) 1762 cm - Example 1-b 163 m9 of 50% sodium hydride in a suspension of 71619 dimethyl-n-hebutyl malonate in dry 1,2-dimethoxyethane. After adding the solution and reacting for 5 minutes with stirring, a solution of 94Q x g of (S)-2,3-epoxypropyl-4-(trans-4-n-bentoline chlorohexyl) phenyl ether in 1,2-dimethoxyethane was added, and the mixture was heated and stirred for 2 and a half hours.
反応液を塩酸酸性とした後、エーテル抽出し、溶媒留去
後、シリカゲルカラムクロマトグラフィーで精製し、次
の化学式（Ａ３）で示される光学活性化合物（２Ｓ、４
Ｓ）本のみのγ−ラクトン誘導体を得た。After making the reaction solution acidic with hydrochloric acid, it was extracted with ether, the solvent was distilled off, and purified by silica gel column chromatography to obtain an optically active compound (2S, 4
S) Only γ-lactone derivatives were obtained.
上記光学活性化合物（Ａ、）の物理的特性を下３己１こ
示す。The physical properties of the optically active compound (A) are shown below.
１１０℃
相転移温度：Ｃ−１
［ｆＺ］Ｐ ＋２７，６１°ＣＣ＝０．０４． ＣＩ（
、ＣＩｌ）ＮＭＲ（ＣＤＣ１，）
δ： ０．８８−１．９８ （３６Ｈ，ａ＋）２、ｌＯ
〜２．８３ （３Ｈ，ｍ）
３．９６−４．１６ （２Ｈ，ｌ）
４．８７〜４．７３ （ＩＨ，ｍ）
６．７５ （２Ｈ，ｄ、 Ｊ ＝８．３Ｈｚ
）７．１０ （２Ｈ，ｄ、 Ｊ ＝８．３Ｈ
ｚ）Ｉ Ｒ（ＫＢｒ） １７６５ｃｍカイラルス
メクチック液晶組成物の調製実施例２
第１表に示す組成のカイラルスメクチックＣ相を有する
液晶組成物を作製した。相転移温度ら併せて示す。110°C Phase transition temperature: C-1 [fZ]P +27,61°CC=0.04. CI(
, CIl) NMR (CDC1,) δ: 0.88-1.98 (36H, a+)2, 1O
~2.83 (3H, m) 3.96-4.16 (2H, l) 4.87 ~ 4.73 (IH, m) 6.75 (2H, d, J = 8.3Hz
) 7.10 (2H, d, J = 8.3H
z) I R (KBr) 1765 cm Preparation of chiral smectic liquid crystal composition Example 2 A liquid crystal composition having a chiral smectic C phase having the composition shown in Table 1 was prepared. The phase transition temperature is also shown.
組成物！及び２共に室温付近でスメクチックＣ田を示し
、組成物ｌはＩＡＣ相系列を、組成物２はｒＮＡｃ相系
列を示す。Composition! and 2 both exhibit a smectic C phase near room temperature, composition 1 exhibits an IAC phase series, and composition 2 exhibits an rNAc phase series.
なお、ネマチック（Ｎ）相、スメクチックＡ（ＳＡ）相
、スメクチックＣ（Ｓｃ）相等の液晶相の同定はホット
ステージ付偏光顕微鏡による組織観察及び既知液晶化合
物の液晶相との相溶性を確認するための二成分系の相図
作成によって行なった。In addition, the identification of liquid crystal phases such as nematic (N) phase, smectic A (SA) phase, and smectic C (Sc) phase is performed by observing the structure using a polarizing microscope with a hot stage and by confirming the compatibility with the liquid crystal phase of known liquid crystal compounds. This was done by constructing a phase diagram of a two-component system.
また、同表中の化合物のうち、２Ｍ４．２ＭＳ、４Ｍ６
．６Ｍ８はそれぞれ光学活性の２−メチル−ブチル基、
３−メチル−ペンチル基、４−メチル−ヘキシル基、６
−メチル−オクチル基を示す。Also, among the compounds in the same table, 2M4.2MS, 4M6
．． 6M8 is an optically active 2-methyl-butyl group,
3-methyl-pentyl group, 4-methyl-hexyl group, 6
-Methyl-octyl group.
実施例３
実施例２で調製した液晶組成物を用いて液晶表示装置を
作製した。２枚のガラス基板上にＩＴＯ膜を形成し、ナ
イロン膜を塗布しラビングする。Example 3 A liquid crystal display device was manufactured using the liquid crystal composition prepared in Example 2. An ITO film is formed on two glass substrates, and a nylon film is applied and rubbed.
次にこの２枚のガラス基板をラビング方向が同一・にな
るようにしてセル厚２μ曙で張り合わせる。このセルに
第１表に示す液晶組成物１．２を注入した。この液晶素
子を２枚の直交する偏光子の間に設置し、電界を印加し
、透過光強度の変化を観察した。Ｖｐ−ｐ＝２０Ｖの電
界を２５℃で印加した時の透過光強度の変化より求めた
応答速度を第１表中に併せて示した。Next, these two glass substrates are pasted together so that the rubbing directions are the same and the cell thickness is 2 μm. Liquid crystal composition 1.2 shown in Table 1 was injected into this cell. This liquid crystal element was placed between two orthogonal polarizers, an electric field was applied, and changes in transmitted light intensity were observed. Table 1 also shows the response speed determined from the change in transmitted light intensity when an electric field of Vp-p=20V was applied at 25°C.
このようにカイラルスメクチックＣ相を呈する液晶組成
物を用いた液晶表示装置においては第１表に示すように
良好な配向性と高速応答性が得られた。In the liquid crystal display device using the liquid crystal composition exhibiting the chiral smectic C phase, as shown in Table 1, good alignment and high-speed response were obtained.
実施例４
実施例！−１の４−（トランス−４−ｎ−ベンチルンク
ロヘキシル）フェノールのｎ−ペンチル基を、下記第２
表のＲＩで示される置換基の１つで置換して調製された
フェノール類と、同表のＲ２で示される置換基の１つで
置換して調製されたマロン酸エステルとを用いる以外は
、実施例１−２Ｌ及び実施例１−ｂと同様にして、化合
物Ａ４〜Ａ１１を調製した。これらの化合物の物理的特
性を併せて第２表に示した。Example 4 Example! -1, the n-pentyl group of 4-(trans-4-n-bentrunechlorohexyl)phenol is replaced with the following
Except for using a phenol prepared by substitution with one of the substituents shown by RI in the table and a malonic acid ester prepared by substituting with one of the substituents shown by R2 in the same table, Compounds A4 to A11 were prepared in the same manner as in Example 1-2L and Example 1-b. The physical properties of these compounds are also shown in Table 2.
実施例５
カイラルスメクチックＣ相を示す種々の液晶組成物を、
第３表に示す各組成でそれぞれ調製した。Example 5 Various liquid crystal compositions exhibiting chiral smectic C phase were
Each composition shown in Table 3 was prepared.
同表には各液晶組成物について、相転移温度及び実施例
３と同様にして測定された応答速度を合わせて示した。The table also shows the phase transition temperature and response speed measured in the same manner as in Example 3 for each liquid crystal composition.
（以下余白）
（ト）発明の効果
この発明によれば、大容量、広視角の強誘電性液晶表示
に適した高速応答性を有するカイラルスメクチック液晶
組成物が得られる。さらに加え、常温付近でスメクチッ
クＣ相を示し理想的な液晶用系列を示す液晶組成物を得
ることができる。(Hereinafter in the margins) (g) Effects of the Invention According to the present invention, a chiral smectic liquid crystal composition having high-speed response suitable for a large-capacity, wide-viewing-angle ferroelectric liquid crystal display can be obtained. In addition, it is possible to obtain a liquid crystal composition that exhibits a smectic C phase at around room temperature and exhibits an ideal liquid crystal series.
Claims (1)
）： ▲数式、化学式、表等があります▼……（Ａ） （式中、Ｒ＿１とＲ＿２は、同一又は異なって、直鎖状
又は分枝状で炭素数１〜１２のアルキル基を示す。 ＊はそのＣが光学活性炭素原子であることを示す）で表
わされる化合物の少なくとも１種を添加してなるカイラ
ルスメクチック液晶組成物。 ２、スメクチックＣ相を呈する液晶化合物が、下式（Ｂ
）： ▲数式、化学式、表等があります▼……（Ｂ） （式中、Ｒ＿３は直鎖状又は分枝状で炭素数１〜１２の
アルキル基又はアルコキシ基、Ｒ＿４は直鎖状又は分枝
状で炭素数１〜１２のアルキル基を示す）で表わされる
化合物の１種又は２種以上からなる請求項１記載の液晶
組成物。 ３、スメクチックＣ相を呈する液晶化合物が前記式（Ｂ
）で表わされる化合物の１種又は２種以上と、下式（Ｃ
）： ▲数式、化学式、表等があります▼……（Ｃ） （式中、Ｒ＿５は直鎖状又は分枝状で炭素数１〜１２の
アルキル基又はアルコキシ基、Ｒ＿６は直鎖状又は分枝
状で炭素数１〜１２のアルコキシ基又はそのアルコキシ
基を有するアルコキシカルボニル基を示し、Ｘは−ＣＯ
Ｏ−、−ＯＣＯ−又は単結合を示す。ｍとｎはそれぞれ
１又は２の整数である。） で表わされる化合物の１種又は２種以上とからなる請求
項２記載の液晶組成物。 ４、請求項１〜３のいずれかに記載のカイラルスメクチ
ック液晶組成物を用いてなる液晶表示装置。[Scope of Claims] 1. A liquid crystal compound exhibiting a smectic C phase has the following formula (A
): ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(A) (In the formula, R_1 and R_2 are the same or different and represent a linear or branched alkyl group having 1 to 12 carbon atoms. A chiral smectic liquid crystal composition containing at least one compound represented by *indicates that C is an optically active carbon atom. 2. A liquid crystal compound exhibiting a smectic C phase has the following formula (B
): ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(B) (In the formula, R_3 is a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, and R_4 is a linear or branched alkyl group or an alkoxy group having 1 to 12 carbon atoms. 2. The liquid crystal composition according to claim 1, comprising one or more compounds represented by the formula (branched alkyl group having 1 to 12 carbon atoms). 3. A liquid crystal compound exhibiting a smectic C phase has the formula (B
) and one or more compounds represented by the following formula (C
): ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(C) (In the formula, R_5 is a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, and R_6 is a linear or branched alkyl group or an alkoxy group having 1 to 12 carbon atoms. It represents a branched alkoxy group having 1 to 12 carbon atoms or an alkoxycarbonyl group having an alkoxy group, and X is -CO
Indicates O-, -OCO- or a single bond. m and n are each an integer of 1 or 2. ) The liquid crystal composition according to claim 2, comprising one or more compounds represented by: 4. A liquid crystal display device using the chiral smectic liquid crystal composition according to any one of claims 1 to 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1052466A JPH0742460B2 (en) | 1988-03-04 | 1989-03-03 | Chiral smectic liquid crystal composition |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63-51818 | 1988-03-04 | ||
| JP5181888 | 1988-03-04 | ||
| JP1052466A JPH0742460B2 (en) | 1988-03-04 | 1989-03-03 | Chiral smectic liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02110189A true JPH02110189A (en) | 1990-04-23 |
| JPH0742460B2 JPH0742460B2 (en) | 1995-05-10 |
Family
ID=26392394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1052466A Expired - Lifetime JPH0742460B2 (en) | 1988-03-04 | 1989-03-03 | Chiral smectic liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0742460B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05165031A (en) * | 1991-12-11 | 1993-06-29 | Sharp Corp | Liquid crystal display device |
| JPH05173144A (en) * | 1991-12-25 | 1993-07-13 | Sharp Corp | Liquid crystal display device |
-
1989
- 1989-03-03 JP JP1052466A patent/JPH0742460B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05165031A (en) * | 1991-12-11 | 1993-06-29 | Sharp Corp | Liquid crystal display device |
| JPH05173144A (en) * | 1991-12-25 | 1993-07-13 | Sharp Corp | Liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0742460B2 (en) | 1995-05-10 |
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