JPH08802B2 - Optically active compound and smectic liquid crystal composition using the same - Google Patents
Optically active compound and smectic liquid crystal composition using the sameInfo
- Publication number
- JPH08802B2 JPH08802B2 JP61079204A JP7920486A JPH08802B2 JP H08802 B2 JPH08802 B2 JP H08802B2 JP 61079204 A JP61079204 A JP 61079204A JP 7920486 A JP7920486 A JP 7920486A JP H08802 B2 JPH08802 B2 JP H08802B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- ring
- liquid crystal
- optically active
- alkyl group
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 56
- 239000004990 Smectic liquid crystal Substances 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 title claims description 15
- -1 1,4-di-substituted phenylene Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004956 cyclohexylene group Chemical class 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000010287 polarization Effects 0.000 description 12
- 230000002269 spontaneous effect Effects 0.000 description 12
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 6
- 230000004044 response Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002262 Schiff base Substances 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 230000005621 ferroelectricity Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DJNRDDUZOGKMIC-UHFFFAOYSA-N (4-hexoxyphenyl) 4-octoxybenzoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)OC1=CC=C(OCCCCCC)C=C1 DJNRDDUZOGKMIC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004891 communication 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
Landscapes
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、表示素子又は電気光学素子に用いられる光
学活性アミド化合物およびそれを用いた強誘電性スメク
チック液晶組成物に関するものである。TECHNICAL FIELD The present invention relates to an optically active amide compound used in a display device or an electro-optical device, and a ferroelectric smectic liquid crystal composition using the same.
［従来の技術］ 従来、時計電卓等の表示部に用いられているネマチッ
ク液晶を使用した液晶表示素子は、その応答速度が、他
の表示素子たとえば、発光ダイオードよりも非常に遅い
ため、高速の応答が必要とされる分野、たとえば、光通
信、プリンターヘッドへの液晶表示素子への応用は制限
されていた。[Prior Art] A liquid crystal display element using a nematic liquid crystal conventionally used for a display unit of a watch calculator or the like has a response speed which is much slower than that of another display element, for example, a light emitting diode. Applications in areas where response is required, such as optical communication and liquid crystal display devices for printer heads, have been limited.
最近、高速の応答性を示す液晶表示素子として、強誘
電性を示すスメクチック液晶を使用した液晶表示素子が
報告され（例えば、N.A.Clark,S.T.Lagerwall,Appl.Phy
s.Lett.36,899（1980））注目を集めている。Recently, a liquid crystal display device using a smectic liquid crystal exhibiting ferroelectricity has been reported as a liquid crystal display device exhibiting high-speed response (for example, NAClark, STLagerwall, Appl.Phy.
s. Lett. 36 , 899 (1980)) is attracting attention.
強誘電性を示すスメクチック液晶としては、カイラル
スメクチックＣ相と、カイラルスメクチックＨ相があ
り、これらは層状構造を示し、液晶分子が層の積み重ね
方法に対して垂直でなく傾むいている。この傾むき方向
が、層の積み重ね芳香に対して、らせんを巻くように液
晶分子は配列しており、この層と平行で、かつ液晶分子
に垂直な芳香に自発分極が発生し強誘電性を示す。この
らせん構造が強誘電性を示す原因と考えられている。強
誘電性を示す材料は、電界に対して強誘電体としての応
答性を示し、電界の向きに応じて自発分極の向きを反転
させて再配列する。Ferroelectric smectic liquid crystals include a chiral smectic C phase and a chiral smectic H phase, which have a layered structure in which liquid crystal molecules are tilted rather than perpendicular to the layer stacking method. The liquid crystal molecules are arranged so that this tilting direction spirals with respect to the stacked fragrance of the layers, and spontaneous polarization is generated in the fragrance that is parallel to this layer and perpendicular to the liquid crystal molecules, and the ferroelectricity is improved. Show. This helical structure is considered to be the cause of the ferroelectricity. A material exhibiting ferroelectricity exhibits responsiveness as a ferroelectric substance to an electric field, and reorients by inverting the direction of spontaneous polarization according to the direction of the electric field.
このとき、応答性は自発分極が大きく、粘度が低いほ
ど同じ電界強度に対しより高速となることが知られてい
る。また、強誘電性スメクチック液晶を用いた素子はメ
モリー性があり、このメモリー性を利用して高密度の表
示を行なう研究も開発になされている。At this time, it is known that the responsiveness has a large spontaneous polarization, and the lower the viscosity is, the faster the response is for the same electric field strength. In addition, an element using a ferroelectric smectic liquid crystal has a memory property, and research has been conducted to develop a high density display by utilizing this memory property.
［発明の解決しようとする問題点］ 従来、強誘電性スメクチック液晶としては、シツフ塩
基型の下記に示すような化合物が多く研究されてきた。[Problems to be Solved by the Invention] As a ferroelectric smectic liquid crystal, conventionally, a lot of compounds having a Schiff base type as shown below have been studied.
ｐ−デシルオキシベンジリデン−ｐ′−アミノ−２−
メチルブチル−桂皮酸エステル（DOBAMBC） しかし、このようなシツフ塩基型化合物は加水分解し
やすいため、水分によって分解しやすい問題点があっ
た。 p-decyloxybenzylidene-p'-amino-2-
Methylbutyl-cinnamic acid ester (DOBAMBC) However, since such a Schiff base type compound is easily hydrolyzed, there is a problem that it is easily decomposed by water.
また、カイラルスメクチックＣ相を示すエステル型化
合物として、下記に一般式（II）で示すような化合物も
知られていた。Further, as an ester type compound exhibiting a chiral smectic C phase, a compound represented by the following general formula (II) has been known.
（G.W.Gray等 Mol.Cryst.Liq.Cryst.,1976,37189−21
1） （Ｒは、炭素数５〜10の直鎖状アルキル基） しかしながら、このエステル化合物は水分には耐える
もののその自発分極の値が小さいという問題点を有して
いた。(GW Gray et al. Mol.Cryst.Liq.Cryst., 1976, 37 189-21
1) (R is a straight-chain alkyl group having 5 to 10 carbon atoms) However, this ester compound has a problem that its spontaneous polarization value is small although it withstands moisture.
さらに最近、自発分極の大きな化合物として、DOBA−
１−MBCと略称される下記の構造の化合物が吉野等（K.Y
OSHINO等、J.J.A.P.,1984,23 L 175−177）によって報
告されている。More recently, as a compound with large spontaneous polarization, DOBA-
The compound of the following structure, abbreviated as 1-MBC, is
OSHINO et al., JJAP, 1984, 23 L 175-177).
しかし、この化合物もシツフ塩基型であるため水分に
よって分解しやすい欠点を有している。 However, since this compound is also a Schiff base type, it has a drawback that it is easily decomposed by water.
［問題を解決するための手段］ 本発明は前述の問題点を解決するためになされたもの
であり、一般式 （式中、Z,Z′は単結合、−COO−、−OCO−、−CH2CH2
−、−OCH2−又は−CH2O−をあらわし、Ｒは炭素数１〜
12のアルキル基もしくはアルコキシ基、シアノ基又はハ
ロゲン原子をあらわし、環Ａ及び環Ｂは1,4−ジ置換フ
ェニレンもしくはトランス1,4−ジ置換シクロヘキシレ
ンをあらわし、ｎは０又は１をあらわし、Ｘは をあらわし、＊は光学活性中をあらわし、Ｒ′は炭素数
２〜12のアルキル基または Ｒ″は水素原子または炭素数１〜20のアルキル若しくは
アルコキシ基をあらわす）で示される光学活性アミド化
合物であり、この一般式（Ｉ）で示される光学活性アミ
ド化合物を少なくとも１種含有する強誘電性スメクチッ
ク液晶組成物である。[Means for Solving the Problem] The present invention has been made to solve the above-described problems, and has the general formula (Wherein, Z, Z 'represents a single bond, -COO -, - OCO -, - CH 2 CH 2
Represents —, —OCH 2 — or —CH 2 O—, and R represents 1 to 1 carbon atoms.
12 represents an alkyl group or an alkoxy group, a cyano group or a halogen atom, ring A and ring B represent 1,4-di-substituted phenylene or trans 1,4-di-substituted cyclohexylene, and n represents 0 or 1. X is Represents an optically active compound, and R ′ represents an alkyl group having 2 to 12 carbon atoms or R ″ represents a hydrogen atom or an alkyl or alkoxy group having 1 to 20 carbon atoms) and is a ferroelectric containing at least one optically active amide compound represented by the general formula (I). Smectic liquid crystal composition.
一般式（Ｉ）の化合物において、Ｚ及びＺ′は単結
合、−COO−、−OCO−、−CH2CH2−、−OCH2−又は−CH
2O−をあらわすが、一般に単結合である場合には粘度が
低く、−COO−である場合にはスメクチックＣ相を示す
上限温度（Ts）が高いので、単結合又は−COO−が好ま
しい。In the compound of general formula (I), Z and Z ′ are a single bond, —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 — or —CH.
Represents 2 O-, a single bond or -COO- is preferable because it generally has a low viscosity when it is a single bond and a high maximum temperature (Ts) showing a smectic C phase when it is -COO-.
また、ｎ＝１の場合には、Ｚ、Ｚ′の両方が−COO−
であると粘度が高くなるので、その場合には少なくとも
一方は単結合であることが好ましい。When n = 1, both Z and Z'are -COO-
Since the viscosity becomes high, it is preferable that at least one of them is a single bond.
環Ａ及び環Ｂは1,4−ジ置換フェニレンもしくはトラ
ンス−1,4−ジ置換シクロヘキシレンをあらわすが、一
般にトランス−1,4−ジ置換シクロヘキシレンの方が1,4
−ジ置換フェニレンよりも粘度が低く、分子量の大きい
化合物は粘度が高いので、ｎ＝１の場合には、環Ａ、環
Ｂの少なくとも一方はトランス−1,4−ジ置換シクロヘ
キシレンであることが好ましいが、ｎ＝０の場合には分
子量が大きくないので、1,4−ジ置換フェニレン、トラ
ンス−1,4−ジ置換シクロヘキシレンのいずれであって
もよい。Ring A and ring B represent 1,4-di-substituted phenylene or trans-1,4-di-substituted cyclohexylene, but trans-1,4-di-substituted cyclohexylene is generally 1,4
-A compound having a lower viscosity and a higher molecular weight than di-substituted phenylene has a high viscosity. Therefore, when n = 1, at least one of ring A and ring B is trans-1,4-di-substituted cyclohexylene. Is preferable, but when n = 0, the molecular weight is not large, and therefore either 1,4-di-substituted phenylene or trans-1,4-di-substituted cyclohexylene may be used.
又、Ｒは炭素数は１〜12のアルキル基、炭素数は１〜
12のアルコキシ基、シアノ基又はハロゲン原子をあらわ
すが、シアノ基の場合には粘度が高く、またハロゲン原
子の場合にはTsが低いのでアルキル基又はアルコキシ基
であることが好ましい。また、アルキル基、アルコキシ
基の場合、その炭素数が少ない場合には融点が高く、多
すぎる場合にはその粘度が高いので１〜12であるが、好
ましくは２〜８が良い。又、直鎖状でも分岐状でも良い
が、一般に直鎖状のものの方が、他の液晶性を示す化合
物と混合した場合にそのスメクチックＣ相を示す液晶上
限温度が高いので好ましい。R is an alkyl group having 1 to 12 carbon atoms, and 1 to 12 carbon atoms.
12 represents an alkoxy group, a cyano group, or a halogen atom. In the case of a cyano group, the viscosity is high, and in the case of a halogen atom, Ts is low, so an alkyl group or an alkoxy group is preferable. In the case of an alkyl group or an alkoxy group, the melting point is high when the carbon number is small, and the viscosity is high when the carbon number is too large, and therefore it is 1 to 12, but preferably 2 to 8. In addition, it may be linear or branched, but in general, a linear one is preferable because it has a higher liquid crystal upper limit temperature showing a smectic C phase when mixed with another compound having liquid crystallinity.
同様な理由により、もしＲ′が であり、Ｒ″がアルキル基かアルコキシ基の場合、Ｒ″
は炭素数が１〜12の直鎖状であることが好ましく、特に
は炭素数２〜８が好ましい。For the same reason, if R'is And R ″ is an alkyl group or an alkoxy group, R ″
Is preferably a straight chain having 1 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms.
従って、本発明の好ましい態様は以下に示すＡとＢで
ある。Therefore, the preferred embodiments of the present invention are A and B shown below.
（Ａ）一般式（Ｉ）において、Ｒが炭素数１〜12の直鎖
状アルキル基をあらわし、環Ａがトランス−1,4−ジ置
換シクロヘキシレンをあらわし、環Ｂが1,4−ジ置換フ
ェニレンをあらわし、Ｚが単結合をあらわし、Ｚ′が単
結合又は−COO−をあらわし、ｎが１をあらわすところ
の光学活性アミド化合物。(A) In the general formula (I), R represents a linear alkyl group having 1 to 12 carbon atoms, ring A represents trans-1,4-di-substituted cyclohexylene, and ring B represents 1,4-di An optically active amide compound in which substituted phenylene is represented, Z is a single bond, Z ′ is a single bond or —COO—, and n is 1.
（Ｂ）一般式（Ｉ）において、Ｒが炭素数１〜12の直鎖
状アルキル基又は直鎖状アルコキシ基をあらわし、環Ａ
が1,4−ジ置換フェニレンをあらわし、Ｚが単結合又は
−COO−をあらわし、ｎが０をあらわすところの光学活
性アミド化合物。(B) In the general formula (I), R represents a linear alkyl group or a linear alkoxy group having 1 to 12 carbon atoms, and a ring A
Represents an 1,4-disubstituted phenylene, Z represents a single bond or —COO—, and n represents 0, an optically active amide compound.
なお、一般式（Ｉ）で示される化合物の旋光性は、左
旋性であるか右旋性であるかを問わない。The optical rotatory power of the compound represented by the general formula (I) may be levorotatory or dextrorotatory.
これらの好ましい態様の光学活性アミド化合物は、低
い粘度を示し、スメクチックＣ相の上限温度（Ts）をほ
とんど低下させなく、前記光学活性エステル化合物より
も一般に高い自発分極を示す。これらの中でも、特にＺ
及びＺ′が単結合の光学活性アミド化合物が好ましい。The optically active amide compound of these preferred embodiments exhibits low viscosity, hardly lowers the maximum temperature (Ts) of the smectic C phase, and generally exhibits higher spontaneous polarization than the optically active ester compound. Among these, especially Z
And an optically active amide compound in which Z'is a single bond is preferable.
一般式（Ｉ）で示される化合物は、強誘電性スメクチ
ック液晶表示素子又は電気光学素子に使用されるには、
所望の温度範囲でカイラルスメクチックＣ相を有するよ
うに、他の強誘電性スメクチック液晶、スメクチック液
晶あるいは他の光学活性物質と適宜混合し、強誘電性ス
メクチック液晶組成物として使用する。更にらせんピッ
チを調整したり、カラー表示を行なうために、ネマチッ
ク液晶，非液晶，二色性染料等を添加してもよい。本発
明の強誘電性を示すスメクチック液晶組成物中の一般式
（Ｉ）で示される化合物の含有量は、多過ぎる場合には
その強誘電性スメクチック上限温度を低下させる傾向に
あり、少なすぎる場合にはその自発分極を大きくする効
果が小さいので、１〜90Wt％とされ、好ましくは２〜50
Wt％が良い。The compound represented by the general formula (I) is used for a ferroelectric smectic liquid crystal display device or an electro-optical device,
It is used as a ferroelectric smectic liquid crystal composition by appropriately mixing it with another ferroelectric smectic liquid crystal, a smectic liquid crystal or another optically active substance so that it has a chiral smectic C phase in a desired temperature range. Further, nematic liquid crystal, non-liquid crystal, dichroic dye or the like may be added for adjusting the spiral pitch or for displaying color. When the content of the compound represented by the general formula (I) in the ferroelectric smectic liquid crystal composition of the present invention is too large, the ferroelectric smectic maximum temperature tends to be lowered, and when it is too small. Has a small effect of increasing its spontaneous polarization, it is set to 1 to 90 Wt%, preferably 2 to 50 Wt.
Wt% is good.
本発明の一般式（Ｉ）の化合物と混合して、強誘電性
スメクチック液晶組成物として使用される相手の化合物
としては、例えば、以下のようなものがある。Examples of the counterpart compound used as a ferroelectric smectic liquid crystal composition by mixing with the compound of the general formula (I) of the present invention include the following.
以下の例でＲ＊は光学活性を示すアルキル基又はアル
コキシ基を示し、Ｒは本発明のＲとは関係がなく、直鎖
状または分岐したアルキル基又はアルコキシ基を示し、
一つの化合物に同一のＲ＊、Ｒが示されていてもそれら
は同一の基とは限らない。In the examples below, R * represents an optically active alkyl group or alkoxy group, R has no relation to R of the present invention, and represents a linear or branched alkyl group or alkoxy group,
Even if the same R * and R are shown in one compound, they are not necessarily the same group.
これらの外、公知の種々の液晶又は非液晶の液晶添加
物が併用でき、例えば以下のようなものがある。 In addition to these, various known liquid crystal or non-liquid crystal liquid crystal additives can be used in combination.
及びこれらのベンゼン環、シクロヘキサン環等の水素
原子の一部をハロゲン、シアノ基、メチル基等に置換し
た化合物。 And compounds obtained by substituting a part of hydrogen atoms of these benzene ring, cyclohexane ring and the like with halogen, cyano group, methyl group and the like.
この例としては、以下のような誘電率異方性が負の化
合物等の化合物がある。なお、以下の例においては、Ｒ
は本発明のＲとは関係がなく、直鎖状または分岐した炭
素数１〜12のアルキル基を示し、一の化合物に同一のＲ
が示されていてもそれら同一の基とは限らない。Examples of this are compounds such as the following compounds having a negative dielectric anisotropy. In the following example, R
Is a linear or branched alkyl group having 1 to 12 carbon atoms, which is not related to R of the present invention, and is the same R in one compound.
Are not necessarily the same groups.
二色性染料としては、トリスアゾ系，アントラキノン
系など、いわゆるゲストホスト型液晶表示素子に使用さ
れる染料が挙げられる。 Examples of the dichroic dye include dyes used in so-called guest-host type liquid crystal display devices such as trisazo type and anthraquinone type.
強誘電性液晶表示素子、又は電気光学素子は、液晶層
を挟持するように配置し、少なくとも一枚が透明である
複数の全面又は一部に電極を有する基到と、前記液晶層
を囲むように前記電極基板間に形成したシール部材とか
ら成る。該液晶表示素子において前記基板間の厚みは、
0.5〜20μｍが好ましい。また、前記基板には、各々に
平行の配向制御処理がなされても良い。この配列制御の
手段として、配向制御膜を電極基板上に一部又は全面に
塗布してもよい。該配向制御膜としては、ポリイミド等
の、その屈折率が1.5以上の高分子材料が好ましい。更
に偏光子が少なくとも１枚、液晶素子に付設されている
ことが好ましい。該電極基板は少なくとも２枚必要であ
るが、さらに多数枚を積み重ねて使用しても良い。A ferroelectric liquid crystal display element or an electro-optical element is arranged so as to sandwich a liquid crystal layer, and at least one transparent electrode has a plurality of entire surfaces or a portion having electrodes on the whole surface and a portion surrounding the liquid crystal layer. And a sealing member formed between the electrode substrates. In the liquid crystal display element, the thickness between the substrates is
0.5 to 20 μm is preferable. Further, the substrates may be subjected to alignment control processing parallel to each of them. As a means for controlling the arrangement, an orientation control film may be applied on a part or the whole surface of the electrode substrate. As the orientation control film, a polymer material such as polyimide having a refractive index of 1.5 or more is preferable. Furthermore, at least one polarizer is preferably attached to the liquid crystal element. At least two electrode substrates are required, but a larger number of electrode substrates may be stacked and used.
本発明の化合物は例えば以下に示す経路により合成す
ることができる。The compound of the present invention can be synthesized, for example, by the route shown below.
（式中Ｚ、Ｚ′、Ｒ、環Ａ、環Ｂ、ｎおよびＸは前記意
味をもつ） 即ち、カルボン酸（III）に塩化チオニル、オキシ塩
化リン等の塩素化剤を作用させて酸塩化物（IV）とし、
これをピリジン等の塩基性物質の存在下に光学活性二級
アミンと反応させ、抽出、再結晶、カラムクロマトグラ
フィー等一連の精製処理を施すことにより、純粋な
（Ｉ）を合成することができる。 (In the formula, Z, Z ', R, ring A, ring B, n and X have the above-mentioned meanings) That is, carboxylic acid (III) is treated with a chlorinating agent such as thionyl chloride or phosphorus oxychloride to form an acid salt. Thing (IV),
Pure (I) can be synthesized by reacting this with an optically active secondary amine in the presence of a basic substance such as pyridine and subjecting it to a series of purification treatments such as extraction, recrystallization and column chromatography. .
［実施例］ 次に、本発明を実施例により具体的に説明する。[Examples] Next, the present invention will be specifically described with reference to Examples.
実施例１ の化合物2.82g（0.01モル）を塩化チオニル10ml、四塩
化炭素10mlと共に還流温度にて４時間加熱したのち、エ
バポレーターにより低沸点物を除去して、 の化合物を黄色の抽状物質として得た。これをトルエン
15mlを加え、え、 の化合物1.35g（0.01モル）、ピリジン4ml、トルエン20
mlの混合物に10℃以下にて滴加した。滴加後６時間かく
はんし、20％塩酸100mlにあけトルエンにて抽出した。
トルエン層を水洗後、無水硫酸マグネシウムにて乾燥
し、エバポレーターにより溶媒を留去した。残った褐色
抽状物質をエタノール30mlと共に加熱し不溶物を除去し
た。エタノールを留去後クーゲルロア蒸溜装置を用いて
220℃〜230℃/0.1mmHgの留分を集め、トルエンを展開溶
媒としたアルミナのカラムクロマトグラフィーにかけ更
にヘキサン30mlより再結晶し目的とする の化合物を得た。収量2.9g（0.0072モル）、収率72％、
融点74.0℃ ［α］D 25＝＋128゜（Ｃ＝0.68,CHCl3,l＝10mm） この化合物のIRスペクトルを第１図に示す。Example 1 2.82 g (0.01 mol) of the compound of 2 was heated with 10 ml of thionyl chloride and 10 ml of carbon tetrachloride at a reflux temperature for 4 hours, and low-boiling substances were removed by an evaporator. Was obtained as a yellow solid. This is toluene
Add 15 ml, Compound of 1.35g (0.01mol), pyridine 4ml, toluene 20
To the mixture of ml was added dropwise below 10 ° C. After the dropwise addition, the mixture was stirred for 6 hours, poured into 100 ml of 20% hydrochloric acid and extracted with toluene.
The toluene layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off with an evaporator. The remaining brown extract was heated with 30 ml of ethanol to remove insoluble matter. After distilling off ethanol, use the Kugelrohr distiller
The fraction of 220 ℃ -230 ℃ / 0.1mmHg is collected, subjected to alumina column chromatography with toluene as a developing solvent, and recrystallized from 30ml of hexane. Was obtained. Yield 2.9g (0.0072mol), Yield 72%,
Melting point 74.0 ° C. [α] D 25 = + 128 ° (C = 0.68, CHCl 3 , l = 10 mm) The IR spectrum of this compound is shown in FIG.
この化合物の1H NMRスペクトルは以下のとおりであっ
た。The 1 H NMR spectrum of this compound was as follows.
実施例２ 実施例１において の化合物に代えて の化合物3.50g（0.01モル）を用いて同実施例と同様の
処理を施すことにより、目的とする の化合物を得た。収量3.0g（0.0064モル）、収率64％、
融点136.6℃ ［α］D 25＝＋110.6゜（Ｃ＝0.92,CHCl3,l＝10mm） この化合物のIRスペクトルを第２図に示す。 Example 2 In Example 1 Instead of the compound 3.50g (0.01mol) of the compound of Was obtained. Yield 3.0g (0.0064mol), Yield 64%,
Melting point 136.6 ° C. [α] D 25 = + 110.6 ° (C = 0.92, CHCl 3 , l = 10 mm) The IR spectrum of this compound is shown in FIG.
実施例３ 実施例２において の化合物に代えて式（＋）−ｎ−C6H13−CH（CH3）−NH
−CH3の化合物1.43g（0.01モル）を用いて、同実施例と
同様の処理を施すことにより目的とする の化合物を得た。収量2.5g（0.0053モル）、収率53％、
融点80.8℃、 ［α］D 25＝＋23.1゜（Ｃ＝0.81,CHCl3,l＝10mm） この化合物のIRスペクトルを第３図に示す。Example 3 In Example 2 Equation (+) instead of the compound - n-C 6 H 13 -CH (CH 3) -NH
By using 1.43 g (0.01 mol) of the compound of --CH 3 and performing the same treatment as in the same example, Was obtained. Yield 2.5g (0.0053mol), yield 53%,
Melting point 80.8 ° C., [α] D 25 = + 23.1 ° (C = 0.81, CHCl 3 , l = 10 mm) The IR spectrum of this compound is shown in FIG.
実施例４ 実施例２において の化合物に代えて（＋）−α−ピペリコン0.99g（0.01
モル）を用いて同実施例と同様の処理を施すことにより
目的とする の化合物を得た。収量2.9g（0.0067モル）、収率67％。Example 4 In Example 2 (+)-Α-pipericone 0.99g (0.01
Mol) is used to carry out the same treatment as in the above-mentioned Example to obtain the objective. Was obtained. Yield 2.9 g (0.0067 mol), yield 67%.
実施例５ 実施例３において の化合物に代えて の化合物3.26g（0.01モル）を用いて同実施例と同様の
処理を施すことにより目的とする の化合物を得た。収量3.4g（0.0075モル）、収率75％、
融点39.5℃、 ［α］D 25＝＋14.6゜（Ｃ＝0.96,CHCl3,l＝10mm）、 この化合物のIRスペクトルを第４図に示す。Example 5 In Example 3 Instead of the compound 3.26g (0.01mol) of the compound of Was obtained. Yield 3.4g (0.0075mol), Yield 75%,
Melting point: 39.5 ° C., [α] D 25 = + 14.6 ° (C = 0.96, CHCl 3 , l = 10 mm). IR spectrum of this compound is shown in FIG.
実施例６ 実施例５の式（＋）−ｎ−C6H13−CH（CH3）−NH−CH
3の化合物に代えて、 の化合物1.35g（0.01モル）を用いて、実施例５と同様
の処理を施すことにより、目的とする の化合物を得た。収量2.7g（0.0061モル）、収率61％、
融点78.1℃、 ［α］D 25＝＋117.5゜（Ｃ＝0.88,CHCl3,l＝10mm）、 この化合物のIRスペクトルを第５図に示す。Formula Example 6 Example 5 (+) - n-C 6 H 13 -CH (CH 3) -NH-CH
Instead of the compound of 3 , Using 1.35 g (0.01 mol) of the compound of Example 1, the same treatment as in Example 5 was carried out to obtain the desired compound. Was obtained. Yield 2.7g (0.0061mol), Yield 61%,
Melting point 78.1 ° C., [α] D 25 = + 117.5 ° (C = 0.88, CHCl 3 , l = 10 mm). IR spectrum of this compound is shown in FIG.
上記実施例と同様にして、対応するカルボン酸と、光
学活性二級アミンとから、以下の式で示される光学活性
アミド化合物を得ることができる。An optically active amide compound represented by the following formula can be obtained from a corresponding carboxylic acid and an optically active secondary amine in the same manner as in the above Examples.
実施例７ 実施例１、２、３および６の化合物を４−ｎ−オクチ
ルオキシ安息香酸４−ｎ−ヘキシルオキシフェニル（以
下、母体液晶と称す）に5.0wt％混合し（以下、それぞ
れ混合物１、２、３および６と称す）、それらの自発分
極および強誘電性スメクチック相を示す上限温度（Ts）
を測定した。自発分極の測定は試料を、３μｍのスペー
サーをはさみ電極面積が1cm2であるセルに封入し、Ts−
10℃において20Hz、10Vの三角波を印加するMiyasato等
の方法に従い、行なった。（K.Miyasato等、Japan、J.A
ppl.Phys.,22,L 661（1983））また、Tsの測定はホット
ステージ（メトラー社製FP51）付の偏光顕微鏡下の観察
により行なった。 Example 7 The compounds of Examples 1, 2, 3 and 6 were mixed with 4-n-hexyloxyphenyl 4-n-octyloxybenzoate (hereinafter, referred to as a host liquid crystal) at 5.0 wt% (hereinafter, each mixture 1 2, 3, and 6), their spontaneous polarization and the maximum temperature (Ts) at which they exhibit a ferroelectric smectic phase.
Was measured. To measure the spontaneous polarization, enclose the sample in a cell with a 3 μm spacer and an electrode area of 1 cm 2 , and apply Ts-
It was performed according to the method of Miyasato et al. Applying a triangular wave of 20 Hz and 10 V at 10 ° C. (K. Miyasato et al., Japan, JA
Ppl.Phys., 22 , L 661 (1983)) Further, Ts was measured by observation under a polarizing microscope equipped with a hot stage (FP51 manufactured by METTLER CORPORATION).
その結果を表−１に示す。表−１からわかるように、
自発分極の大きさは、従来研究されている強誘電製液晶
化合物 （DOBAMBC）が単品で3.7nC/cm2であり、エステル型化合
物 が単品で1.8nC/cm2であるのに対し、実施例１、２、３
および６の化合物は5.0wt％に稀釈した混合物であって
も、更に大きな自発分極を有している。また混合物１、
２、３および６はいずれも実用上十分に高いTsを有して
いる。The results are shown in Table-1. As you can see from Table-1,
The magnitude of spontaneous polarization depends on the ferroelectric liquid crystal compound that has been studied in the past. (DOBAMBC) alone is 3.7 nC / cm 2 and is an ester type compound Is 1.8 nC / cm 2 as a single product, while Examples 1, 2 , 3
The compounds of 6 and 6 have a larger spontaneous polarization even in a mixture diluted to 5.0 wt%. Also mixture 1,
All of 2, 3 and 6 have sufficiently high Ts for practical use.
実施例８ 実施例７で用いた混合物２およびDOBAMBCをサンプル
管に入れ、温度80℃、温度90％の雰囲気抽に20時間放置
し、この前後でのTsの変化を調べた。 Example 8 The mixture 2 and DOBAMBC used in Example 7 were put in a sample tube and left in an atmosphere extraction at a temperature of 80 ° C. and a temperature of 90% for 20 hours, and the change in Ts before and after this was examined.
DOBAMBCはシツフ塩基型化合物であるため加水分解を
おこしやすくTsが93.0℃から76.1℃16.9℃も低下したの
に対し、混合物２は64.6℃から64.3℃へと0.3℃しか低
下せず実用上問題がないことがわかった。Since DOBAMBC is a Schiff base type compound, it is easily hydrolyzed and Ts is lowered from 93.0 ℃ to 76.1 ℃ 16.9 ℃, while Mixture 2 is decreased from 64.6 ℃ to 64.3 ℃ only by 0.3 ℃, which is a practical problem. I knew it wasn't.
比較例 実施例１において、 の化合物に代えて の化合物1.21g（0.01モル）を用いて同実施例と同様の
処理を施すことにより の化合物を得た。収量2.7g（0.007モル）、収率70％、
融点167.6℃、［α］D 25＝＋36.1゜（Ｃ＝0.78,HCHl3,l
＝10mm）。Comparative Example In Example 1, Instead of the compound 1.21g (0.01mol) of the compound of Was obtained. Yield 2.7g (0.007mol), Yield 70%,
Melting point 167.6 ° C, [α] D 25 = + 36.1 ° (C = 0.78, HCHl 3 , l
= 10 mm).
この化合物は、実施例１の化合物よりも融点が93.6℃
も高く相溶性に乏しい化合物であった。This compound has a melting point of 93.6 ° C. more than the compound of Example 1.
It was also a compound with high compatibility and poor compatibility.
［発明の効果］ 本発明は自発分極が大きく、かつ化学的に安定な一般
式（Ｉ）で示される光学活性アミド化合物、および該化
合物を少なくとも１種を含有する強誘電性スメクチック
液晶組成物を提供することにより、信頼性に優れた、高
速応答が可能な表示素子又は電気光学素子を構成し得る
ような優れた効果を有する。EFFECTS OF THE INVENTION The present invention provides an optically active amide compound represented by the general formula (I), which has large spontaneous polarization and is chemically stable, and a ferroelectric smectic liquid crystal composition containing at least one compound. By providing, it has an excellent effect that a display element or an electro-optical element having excellent reliability and capable of high-speed response can be configured.
第１図乃至５図は，夫々本発明の実施例１、２、３、５
及び６の化合物のIRスペクトル図である。 第６図は、比較例の化合物のIRスペクトル図である。1 to 5 show Embodiments 1, 2, 3, and 5 of the present invention, respectively.
It is an IR spectrum figure of the compound of 6 and. FIG. 6 is an IR spectrum diagram of the compound of Comparative Example.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０９Ｋ 19/54 Ｂ 9279−4Ｈ Ｇ０２Ｆ 1/13 ５００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Office reference number FI technical display location C09K 19/54 B 9279-4H G02F 1/13 500
Claims (6)
−、−OCH2−又は−CH2O−をあらわし、Ｒは炭素数１〜
12のアルキル基もしくはアルコキシ基、シアノ基又はハ
ロゲン原子をあらわし、環Ａ及び環Ｂは1,4−ジ置換フ
ェニレンもしくはトランス−1,4−ジ置換シクロヘキシ
レンをあらわし、ｎは０又は１をあらわし、 をあらわし、＊は光学活性中心をあらわし、Ｒ′は炭素
数２〜12のアルキル基または Ｒ″は水素原子または炭素数１〜20のアルキル基若しく
はアルコキシ基をあらわす）で示される光学活性アミド
化合物。1. A general formula (Wherein, Z, Z 'represents a single bond, -COO -, - OCO -, - CH 2 CH 2
Represents —, —OCH 2 — or —CH 2 O—, and R represents 1 to 1 carbon atoms.
12 represents an alkyl group or an alkoxy group, a cyano group or a halogen atom, ring A and ring B represent 1,4-di-substituted phenylene or trans-1,4-di-substituted cyclohexylene, and n represents 0 or 1. , , * Represents an optically active center, R ′ represents an alkyl group having 2 to 12 carbon atoms or R ″ represents a hydrogen atom or an alkyl group or an alkoxy group having 1 to 20 carbon atoms) and is an optically active amide compound.
キル基であり、環Ａがトランス−1,4−ジ置換シクロヘ
キシレンをあらわし、環Ｂが1,4−ジ置換フェニレンを
あわらし、Ｚが単結合をあらわし、Ｚ′が単結合をあら
わし、ｎが１をあらわすところの特許請求の範囲第１項
記載の化合物。2. In general formula (I), R is a linear alkyl group, ring A represents trans-1,4-disubstituted cyclohexylene, and ring B represents 1,4-disubstituted phenylene. The compound according to claim 1, wherein Z represents a single bond, Z ′ represents a single bond, and n represents 1.
キル基であり、環Ａがトランス−1,4−ジ置換シクロヘ
キシレンをあらわし、環Ｂが1,4−ジ置換フェニレンを
あらわし、Ｚが単結合をあらわし、Ｚ′が−COO−をあ
らわし、ｎが１をあらわすところの特許請求の範囲第１
項記載の化合物。3. In the general formula (I), R is a linear alkyl group, ring A represents trans-1,4-disubstituted cyclohexylene, and ring B represents 1,4-disubstituted phenylene. In the claims, Z represents a single bond, Z ′ represents —COO—, and n represents 1.
The compound according to the item.
あり、環Ａが1,4−ジ置換フェニレンをあらわし、Ｚが
単結合をあらわし、ｎが０をあらわすところの特許請求
の範囲第１項記載の化合物。4. A patent in which R in the general formula (I) is a linear group, ring A represents 1,4-disubstituted phenylene, Z represents a single bond, and n represents 0. A compound according to claim 1.
あり、環Ａが1,4−ジ置換フェニレンをあらわし、Ｚが
−COO−をあらわし、ｎが０をあらわすところの特許請
求の範囲第１項記載の化合物。5. In general formula (I), R is a linear group, ring A represents 1,4-disubstituted phenylene, Z represents --COO--, and n represents 0. The compound according to claim 1.
−、−OCH2−又は−CH2O−をあらわし、Ｒは炭素数１〜
12のアルキル基もしくはアルコキシ基、シアノ基又はハ
ロゲン原子をあらわし、環Ａ及び環Ｂは1,4−ジ置換フ
ェニレンもしくはトランス−1,4−ジ置換シクロヘキシ
レンをあらわし、ｎは０又は１をあらわし、 をあらわし、＊は光学活性中心をあらわし、Ｒ′は炭素
数２〜12のアルキル基または Ｒ″は水素原子または炭素数１〜20のアルキル基若しく
はアルコキシ基をあらわす）で示される光学活性アミド
化合物を少なくとも１種含有する強誘電性スメクチック
液晶組成物。6. A general formula (Wherein, Z, Z 'represents a single bond, -COO -, - OCO -, - CH 2 CH 2
Represents —, —OCH 2 — or —CH 2 O—, and R represents 1 to 1 carbon atoms.
12 represents an alkyl group or an alkoxy group, a cyano group or a halogen atom, ring A and ring B represent 1,4-di-substituted phenylene or trans-1,4-di-substituted cyclohexylene, and n represents 0 or 1. , , * Represents an optically active center, R ′ represents an alkyl group having 2 to 12 carbon atoms or R ″ represents a hydrogen atom or an alkyl group or an alkoxy group having 1 to 20 carbon atoms), and is a ferroelectric smectic liquid crystal composition containing at least one optically active amide compound.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7669385 | 1985-04-12 | ||
| JP60-76693 | 1985-04-12 |
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| Publication Number | Publication Date |
|---|---|
| JPS6230749A JPS6230749A (en) | 1987-02-09 |
| JPH08802B2 true JPH08802B2 (en) | 1996-01-10 |
Family
ID=13612555
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|---|---|---|---|
| JP61079204A Expired - Lifetime JPH08802B2 (en) | 1985-04-12 | 1986-04-08 | Optically active compound and smectic liquid crystal composition using the same |
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| Country | Link |
|---|---|
| JP (1) | JPH08802B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9243750B2 (en) | 2007-02-02 | 2016-01-26 | Federal-Mogul Corporation | Multi-use container for engine maintenance kit |
-
1986
- 1986-04-08 JP JP61079204A patent/JPH08802B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6230749A (en) | 1987-02-09 |
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