JPH01121276A - Liquid crystal compound and liquid crystal composition containing said compound - Google Patents
Liquid crystal compound and liquid crystal composition containing said compoundInfo
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- JPH01121276A JPH01121276A JP62277521A JP27752187A JPH01121276A JP H01121276 A JPH01121276 A JP H01121276A JP 62277521 A JP62277521 A JP 62277521A JP 27752187 A JP27752187 A JP 27752187A JP H01121276 A JPH01121276 A JP H01121276A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 62
- 150000001875 compounds Chemical class 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims 22
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 22
- -1 pyrazinecarboxylic acid compound Chemical class 0.000 abstract description 10
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 4
- 150000004820 halides Chemical class 0.000 abstract description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 8
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 7
- 230000010287 polarization Effects 0.000 description 6
- 230000002269 spontaneous effect Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LAEZQMVVQHICOO-NTSWFWBYSA-N (2s,3s)-2-chloro-3-methylpentan-1-ol Chemical compound CC[C@H](C)[C@H](Cl)CO LAEZQMVVQHICOO-NTSWFWBYSA-N 0.000 description 1
- LNJZJDLDXQQJSG-UHFFFAOYSA-N 2-phenylpyrazine Chemical class C1=CC=CC=C1C1=CN=CC=N1 LNJZJDLDXQQJSG-UHFFFAOYSA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 1
- 208000003464 asthenopia Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規な液晶性化合物、該液晶性化合物を少なく
とも１種類含有する液晶組成物及び該液晶組成物を用い
た液晶素子に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel liquid crystal compound, a liquid crystal composition containing at least one kind of the liquid crystal compound, and a liquid crystal element using the liquid crystal composition.
現在、液晶は表示材料として広く用いられているが、そ
うした表示素子のほとんどはネマチック相に属する液晶
材料を用いるところのＴＮ（Ｔｗｉｓｔ＋Ｊ Ｎｅｍａ
ｔｉｃ）型表示方式である。このＴＮ型表示方式は受光
型のため目が疲れない、消費電力が極めて少ないなど優
れた特長を持つものであるが、応答速度が遅いこと、視
る角度によってはコントラストがとれないこと、大画面
で高精細な表示素子をつくるためにはＴＦ Ｔ（Ｔｈｉ
ｎ ｆｉｌｍｔｒａｎｓｉｓｔｏｒ）等の能動素子をつ
け加える必要があることなどの欠点がある。最近は、表
示装置に対して高速応答性が要求されており、こうした
要求に答えるべく液晶材料の改良が試みられてきた。し
かし、他の発光型デイスプレィ（ＣＲＴ、ＥＬ、プラズ
マデイスプレィ等）と比較すると、応答速度は十分でな
く、高精細な表示もできなかった。受光型、低消費電力
といった液晶の特長を生かし、なおかつ発光型デイスプ
レィに匹敵する応答速度と高精細性を確保するためには
ネマチック相を利用するＴＮ型表示方式に代わる新しい
液晶表示方式が必要である。新しい液晶表示方式の中で
上記の優れた特性を持つことが期待されるものとして、
強誘電性液晶の光スイツチング現象を利用した表示方式
（Ｎ、Ａ、Ｃ１ａｒｋ、Ｓ、Ｔ、Ｌａｇｅｒｗａｌｌ
；Ａｐｐｌ、Ｐｈｙｓ、Ｌｅｔｔ、、 ３６ 、 ８
９９ （１９８０） ）がある。強誘電性液晶は１
９７５年にＲ，Ｂ、Ｍｅｙｅｒらによってその存在が発
表されたもので （Ｒ、Ｂ 。Currently, liquid crystals are widely used as display materials, but most of these display elements are TN (Twist + J Nema), which uses liquid crystal materials belonging to the nematic phase.
tic) type display method. This TN type display system has excellent features such as being light-receiving type so it does not cause eye strain and consumes very little power, but it has slow response speed, lack of contrast depending on the viewing angle, and large screen size. In order to create high-definition display elements using TF T (Th
There are disadvantages such as the need to add active elements such as n film transistors. Recently, high-speed response has been required for display devices, and attempts have been made to improve liquid crystal materials in order to meet these demands. However, compared to other light-emitting displays (CRT, EL, plasma displays, etc.), the response speed was not sufficient and high-definition display was not possible. In order to take advantage of the features of liquid crystals, such as light-receiving type and low power consumption, and to ensure response speed and high definition comparable to light-emitting displays, a new liquid crystal display method is needed to replace the TN type display method that uses the nematic phase. be. Among the new liquid crystal display systems that are expected to have the above-mentioned excellent characteristics,
Display method using optical switching phenomenon of ferroelectric liquid crystal (N, A, C1ark, S, T, Lagerwall)
;Appl, Phys, Lett, 36, 8
99 (1980)). Ferroelectric liquid crystal is 1
Its existence was announced in 975 by R.B. Meyer et al. (R.B.
Ｍｅ３＋ｅｒ ｅｔ ａｌ、、Ｊ、Ｐｈｙｓ、（Ｐａｒ
ｉｓ） ３６ 、 Ｌ −６９（１９７５））、液晶の
構造上からカイラルスメクチックＣ相（ＳｍＣ”相）、
あるいはカイラルスメクチックＨ相（ＳｍＨ”相）に属
する。その後さらにカイラルスメクチックＩ相（ＳｍＩ
”相）、カイラルスメクチックＦ相（ＳｍＦ’相）、カ
イラルスメクチックＣ相（Ｓ ｍ Ｇ ”相）、カイラ
ルスメクチックＪ相（ＳｍＪ”相）、カイラルスメクチ
ックに相（ＳｍＫ”相）が強誘電性を示す液晶相として
明らかとなった。強誘電性液晶性化合物としては後記表
１に示したものが知られている（Ｐｈ、Ｍａｒｔｉｎｏ
ｔ−Ｌａｇａｒｄｅ、Ｊ、Ｐｈｙｓ、 （Ｐａｒｉｓ）
ｌユ、Ｃ５−１２９（１９７６）等）。Me3+er et al., J. Phys. (Par
is) 36, L-69 (1975)), chiral smectic C phase (SmC" phase) from the structure of liquid crystal,
Or it belongs to the chiral smectic H phase (SmH” phase). Then, it further belongs to the chiral smectic I phase (SmI
``phase), chiral smectic F phase (SmF' phase), chiral smectic C phase (SmG'' phase), chiral smectic J phase (SmJ'' phase), and chiral smectic phase (SmK'' phase) exhibit ferroelectricity. This was revealed as a liquid crystal phase. As ferroelectric liquid crystal compounds, those shown in Table 1 below are known (Ph, Martino
t-Lagarde, J. Phys, (Paris)
IU, C5-129 (1976), etc.).
（発明が解決しようとする問題点〕
ところが、これらの強誘電性液晶性化合物は、それぞれ
カイラルスメクチック相の温度範囲が高い、自発分極が
小さい、閾値特性が悪い等の欠点を持っており、必ずし
も満足すべきものではない。(Problems to be Solved by the Invention) However, these ferroelectric liquid crystal compounds each have drawbacks such as a high chiral smectic phase temperature range, small spontaneous polarization, and poor threshold characteristics. It's not something to be satisfied with.
本発明者らは、強誘電性液晶の光スイツチング現象を利
用した表示方式に利用することに適した液晶物質の開発
を主たる目的として種々の化合物を検討した結果、本発
明に到達した。The present inventors have arrived at the present invention as a result of studying various compounds with the main purpose of developing a liquid crystal material suitable for use in a display system utilizing the optical switching phenomenon of ferroelectric liquid crystal.
〔問題点を解決するための手段及び作用〕本発明は、一
般式（Ｉ）
Ｒ＋ Ｘ＋ Ｚ−Ｘ２ Ｒ２（Ｉ）（但し、式中
、Ｒ１は炭素数１〜１８のアルキル基、Ｒ２はハロゲン
化アルキル基を示し、ｘｌはで表わされる液晶性化合物
、該液晶性化合物を含有する液晶組成物および該液晶組
成物を用いた液晶素子を提供するものである。[Means and effects for solving the problems] The present invention is based on the general formula (I) R+ The present invention provides a liquid crystal compound represented by the following formula, where xl represents an alkyl group, a liquid crystal composition containing the liquid crystal compound, and a liquid crystal element using the liquid crystal composition.
本発明において一般式（Ｉ）で表わされる液晶性化合物
と他の液晶化合物、例えばスメクチック相あるいはカイ
ラルスメクチック相を示す液晶化合物と混合して得られ
る強誘電性カイラルスメクチック液晶組成物は、Ｎ、Ａ
、Ｃ１ａｒｋらによって示されたような表示素子に使用
する場合に、電界応答に対する優れた閾値特性を与える
。このため、該強誘電性カイラルスメクチック液晶組成
物を、単純マトリックス電極にて駆動するデイスプレィ
に使用した場合には、クロストークを防止し良好なコン
トラストを与えることが可能であり、特に高精細・大画
面表示素子として使用するのに適している。In the present invention, the ferroelectric chiral smectic liquid crystal composition obtained by mixing the liquid crystal compound represented by the general formula (I) with another liquid crystal compound, such as a liquid crystal compound exhibiting a smectic phase or a chiral smectic phase, is composed of N, A
, provides excellent threshold characteristics for electric field response when used in display devices such as those shown by C1ark et al. Therefore, when the ferroelectric chiral smectic liquid crystal composition is used in a display driven by a simple matrix electrode, it is possible to prevent crosstalk and provide good contrast, especially in high-definition and large-scale displays. Suitable for use as a screen display element.
さらに、本発明の液晶性化合物を少なくとも１種類配合
成分として含有するネマチック液晶組成物は、ツィステ
ッドネマチック（ＴＮ）型液晶素子中に使用する場合に
リバースドメインの発生を防止することができ、また閾
値特性を改善することができ好ましい。Furthermore, the nematic liquid crystal composition containing at least one liquid crystal compound of the present invention as a compounding component can prevent the occurrence of reverse domains when used in a twisted nematic (TN) type liquid crystal element, and This is preferable because the threshold characteristics can be improved.
上記のような本発明の液晶性化合物を含有する強誘電性
カイラルスメクチック液晶組成物は、例えば、下表−１
で示されるような強屈電性液晶化合物と組合せにより得
ることができる。このような場合においては、一般式（
１’）で示される本発明の液晶性化合物を少なくとも１
種類以上含有し、得られる液晶組成物のｏ、ｉ〜５０重
量％、特に１〜２０重量％となる割合で使用することが
好ましい。The ferroelectric chiral smectic liquid crystal composition containing the liquid crystal compound of the present invention as described above is, for example, as shown in Table 1 below.
It can be obtained in combination with a ferroelectric liquid crystal compound as shown in . In such cases, the general formula (
At least one of the liquid crystalline compounds of the present invention represented by 1')
It is preferable to contain at least one kind of these materials and use them in a proportion of o, i to 50% by weight, particularly 1 to 20% by weight of the resulting liquid crystal composition.
表１
結晶薄ユニＳａ＋Ｃ： ” ： ＳｍＡ ＝＝ｉ等方相
ｒＨ。Table 1 Crystal thin UniSa+C: ”: SmA ==i isotropic phase rH.
ＣＯＯＣＨ２ＣＨＣ２ＨＩ。COOCH2CHC2HI.
４．４′−７ゾキシシンナミツクアシツドービス（２−
メチルブチル）エステルまた下式１）〜５）で示される
ようなそれ自体はカイラルでないスメクチック液晶に配
合することにより強話電性液晶として使用可能な組成物
が得られる。4.4'-7Zoxycinnamic acid bis(2-
By blending the methylbutyl ester with a smectic liquid crystal which itself is not chiral, such as those represented by the following formulas 1) to 5), a composition usable as a strong electroconductive liquid crystal can be obtained.
この場合、一般式（Ｉ）で示される本発明の液晶性化合
物を得られる液晶組成物の０．１〜９９重量％、特に１
〜９０重量％となる割合で使用することが好ましい。In this case, 0.1 to 99% by weight, especially 1% by weight of the liquid crystal composition from which the liquid crystal compound of the present invention represented by general formula (I) is obtained.
It is preferable to use it in a proportion of 90% by weight.
４．４′−デシルオキシアゾキシベンゼンＣｒｙｓｔ、
７７’Ｃ，ＳｍＣ１２０’ＣＮ １２３．’Ｏｒ
ｓｏ。4.4'-decyloxyazoxybenzene Cryst,
77'C, SmC120'CN 123. 'Or
So.
Ｃｒｙｓｔ、坏四。５ｌｌｌＣ４ＳｍＡ Ｍ Ｉｓｏ
。Cryst, Kyoji. 5lllC4SmA M Iso
.
２−（４′−オクチルオキシフェニル）−５−ノニルピ
リミジンＣｒｙｓｔ、 ３３’Ｏ５ｆｌｌＧ ８０
Ｔ３ ＳｍＡ ？５’Ｃ！ Ｉｓｏ。2-(4'-octyloxyphenyl)-5-nonylpyrimidine Cryst, 33'O5fllG 80
T3 SmA? 5'C! Iso.
４′−ペンチルオキシフェニル−４−オクチルオキシベ
ンゾエートＣｒｙｓｔ、 ５８Ｔ３ ＳｍＣｆ１４”
ｃ ！１ｍＡ ｆ１８”ｏ ＮムＩｓｏ。4'-Pentyloxyphenyl-4-octyloxybenzoate Cryst, 58T3 SmCf14"
c! 1mA f18”o Nmu Iso.
ここで、記号は、それぞれ以下の相を示す。Here, the symbols indicate the following phases, respectively.
Ｃｒｙｓｔ、 ：結晶相、ＳｍＡ ：スメクチツクＡ
相。Crystal: Crystal phase, SmA: Smectic A
phase.
５ｆｆｌＢ：スメクチックＢ相、 ５ｆｆｉＣ：スメク
チックＣ相。5fflB: smectic B phase, 5ffiC: smectic C phase.
Ｎ ：ネマチック相、 Ｉｓｏ、 ：等吉相。N: Nematic phase, Iso,: Tokichi phase.
また、前記したように一般式（１）で示される本発明の
液晶性化合物は、ネマチック液晶に添加することにより
、ＴＮ型セルにおけるリバースドメインの発生を防止す
ることに有効である。この場合、式（Ｉ）の液晶性化合
物をネマチック液晶に添加することにより得られる液晶
組成物の０゜０１〜１０重量％の割合で式（ｊ）の液晶
性化合物を使用することが好ましい。Further, as described above, the liquid crystal compound of the present invention represented by the general formula (1) is effective in preventing the occurrence of reverse domains in a TN cell by adding it to a nematic liquid crystal. In this case, it is preferable to use the liquid crystal compound of formula (J) in an amount of 0.01 to 10% by weight of the liquid crystal composition obtained by adding the liquid crystal compound of formula (I) to the nematic liquid crystal.
一般式（Ｉ）で示される液晶性化合物は、例えば下記一
般式（Ｉｆ）〜（Ｖ）
（但し、これらの式中、Ｒ１は炭素数１〜１８のアルキ
ル基、Ｒ２はハロゲン化アルキル基を示−〇−Ｃ−Ｏ−
１および単結合を示し、Ｘ２は■
として、合成することができる。すなわち、一般式（Ｉ
＋ ）または（ＩＩＩ ）で表わされるピラジンカルボ
ン酸化合物をハロゲン化して、酸ハロゲン化物となし、
これに一般式Ｒ２−ＯＨあるいはＲ，−０Ｈ（但し、Ｒ
１は炭素数１〜１８のアルキル基を示し、Ｒ２はハロゲ
ン化アルキル基を示す。）で示されるアルコール化合物
を反応せしめてエステル化する方法；あるいは一般式（
ＴＶ）または（Ｖ）で表わされるヒドロキシピラジン化
合物に、
のアルキル基を示し、Ｒ２はハロゲン化アルキル基を示
す。）で示される酸塩化物を反応せしめてエステル化す
る方法：もしくはＲ，ＯＴ、（但し、Ｒ３は炭素数１〜
１８のアルキル基、Ｔｓはトシル基を示す。）で示され
る化合物等を反応させてエーテル化する方法；または一
般式（Ｖ）で表わされるヒドロキシピラジン化合物を塩
素化し、下記一般式（１）
（但し、式中、Ｒ２はハロゲン化アルキル基、表わされ
るクロロピラジン化合物としたのち、ＲＩ ＭｇＢｒ
（但し、Ｒ１は炭素数１〜１８のアルキル基を示す。）
で示される化合物を反応せしめてアルキル化する方法に
より合成される。The liquid crystalline compound represented by the general formula (I) is, for example, the following general formulas (If) to (V) (in these formulas, R1 is an alkyl group having 1 to 18 carbon atoms, and R2 is a halogenated alkyl group). Show-〇-C-O-
1 and a single bond, and X2 can be synthesized as . That is, the general formula (I
+ ) or (III) by halogenating the pyrazinecarboxylic acid compound to form an acid halide,
To this, the general formula R2-OH or R,-0H (however, R
1 represents an alkyl group having 1 to 18 carbon atoms, and R2 represents a halogenated alkyl group. ) A method of reacting and esterifying an alcohol compound represented by the general formula (
TV) or (V) represents an alkyl group, and R2 represents a halogenated alkyl group. ) A method of reacting and esterifying an acid chloride: or R, OT, (wherein R3 has 1 to 1 carbon atoms)
The alkyl group of 18, Ts, represents a tosyl group. ); Alternatively, a hydroxypyrazine compound represented by the general formula (V) is chlorinated to form the following general formula (1) (wherein, R2 is a halogenated alkyl group, After making the chloropyrazine compound represented, RI MgBr
(However, R1 represents an alkyl group having 1 to 18 carbon atoms.)
It is synthesized by a method of reacting and alkylating the compound shown in
なお、一般式（ｎ ） （ｍ ） （ｒＶ ）
（ｖ ）および（Ｖｌ）で示される化合物は特開昭５９
−１４４７７１号、特開昭６２−７２号多分報および特
願昭６１−２６１７６７号明細書に記載された方法を用
いることにより得られるものである。In addition, the general formula (n) (m) (rV)
The compounds represented by (v) and (Vl) are
-144771, Japanese Patent Application Laid-Open No. 62-72, and Japanese Patent Application No. 61-261767.
なお、上記したハロゲン化アルキル基（Ｒ２）を有する
酸塩化物およびアルコール化合物は、例えばアラニン、
α−アミノ−ｎ−ブチリック酸、バリン、ロイシン、イ
ソロイシン、ノルバリン、ノルロイシンなどの光学活性
あるいはラセミのα−アミノ酸などから誘導できる。例
えば、前記α−アミノ酸を、ハロゲン化水素存在化で亜
硝酸ナトリウムと反応させることによって対応する酸塩
化物を得ることができる。さらに、この酸塩化物あるい
はそのエステル化合物を、リチウムアルミニウムハイド
ライドなどで還元することにより、対応したアルコール
化合物を得ることができる。In addition, the above-mentioned acid chlorides and alcohol compounds having a halogenated alkyl group (R2) include, for example, alanine,
It can be derived from optically active or racemic α-amino acids such as α-amino-n-butyric acid, valine, leucine, isoleucine, norvaline, and norleucine. For example, the corresponding acid chloride can be obtained by reacting the α-amino acid with sodium nitrite in the presence of hydrogen halide. Furthermore, the corresponding alcohol compound can be obtained by reducing this acid chloride or its ester compound with lithium aluminum hydride or the like.
このようにして得られる本発明の液晶性化合物の例とし
ては、下記の化合物があげられる。Examples of the liquid crystalline compound of the present invention obtained in this manner include the following compounds.
Ｃａ Ｈ，、ｏ４発
「
Ｉ
Ｃ＋ｏＨ２＋Ｏ＋、＞ＱＣＣＨＣＨ３
八゛
へＩ
Ｃ＋２Ｈ２ｓ＄、） ＯＣＣＨ（ＣＨ２） ｓ ＣＨ
３１′Ｘ
Ｃ１ａＨ２ｅＯ号毎ＱＣＣＨＣＨＣＣＨ３）２Ａ”
以下、実施例により本発明について更に詳細に説明する
が、本発明はこれらの実施例に限定されるものではない
。Ca H,, o4 ``I C+oH2+O+,>QCCHCH3 8゛I C+2H2s$,) OCCH(CH2) s CH
31'
釆」１生上
［５−（Ｐ−デシルオキシフェニル）−２−（（２Ｓ、
３Ｓ）−２−クロロ−３−メチルペンタノイルオキシ）
ピラジンの合成］
ｐ−デシルオキシフェニルグリオキザール水和物と、グ
リシンアミド塩酸塩とを縮合して得た５−（ｐ−デシル
オキシフェニル）−２−ヒドロキシピラジン１．５ｇ、
ピリジン０．３６ｇをテトラヒドロフラン１０ｍ１中に
入れ、攪拌下に（２Ｓ、３Ｓ）−３−メチル−２−クロ
ルペンタン酸クロライド０．７８ｇとテトラヒドロフラ
ン１０ｍ１の混合液を２０℃で滴下した。２０℃で１時
間攪拌し、５０℃で１時間攪拌した。冷却後、生成した
固体を炉別し、溶液を濃縮した。得られた残留物ヲトル
エン１５０ｍ１で抽出し、トルエン層を水１００ｍ１で
２回洗浄したのち、トルエンを留去して粗生成物２．０
ｇを得た。この粗生成物をシリカゲル８０ｇを使用し、
クロマトグラフィーを行ない、トルエンで展開し０．９
８の生成物を得た。1 fresh [5-(P-decyloxyphenyl)-2-((2S,
3S)-2-chloro-3-methylpentanoyloxy)
Synthesis of pyrazine] 1.5 g of 5-(p-decyloxyphenyl)-2-hydroxypyrazine obtained by condensing p-decyloxyphenylglyoxal hydrate and glycinamide hydrochloride,
0.36 g of pyridine was placed in 10 ml of tetrahydrofuran, and a mixed solution of 0.78 g of (2S, 3S)-3-methyl-2-chloropentanoic acid chloride and 10 ml of tetrahydrofuran was added dropwise at 20°C while stirring. The mixture was stirred at 20°C for 1 hour, and then at 50°C for 1 hour. After cooling, the solid produced was separated in the furnace and the solution was concentrated. The obtained residue was extracted with 150 ml of toluene, the toluene layer was washed twice with 100 ml of water, and the toluene was distilled off to give a crude product of 2.0 ml.
I got g. Using 80 g of silica gel, this crude product was
Perform chromatography and develop with toluene to obtain 0.9
8 products were obtained.
Ｉ Ｒ（υＣｍ−’） ： １ ７６０ （Ｃ
＝０）元素分析値： Ｃ２８Ｈ３７Ｎ２０３ Ｃ１とし
て計算値：Ｃ６７，７３、Ｈ８，０９、
Ｈ６，０８。I R(υCm-'): 1 760 (C
=0) Elemental analysis value: C28H37N203 Calculated value as C1: C67.73, H8.09, H6.08.
実測値：Ｃ６７，８０、ＨＢ、２Ｂ、 Ｎ５．８Ｂ 。Actual value: C67, 80, HB, 2B, N5.8B.
火五■ユ
［５−（ｐ−デシルオキシフェニル）ピラジン−２−カ
ルボン酸（２Ｓ、３Ｓ）−２−クロル−３−メチルペン
チルエステルの合成コ
５−（ｐ−デシルオキシフェニル）ピラジン−２−カル
ボン酸クロライド２．０ｇと（２Ｓ、３Ｓ）−２−クロ
ル−３−メチルペンタノール０゜７３ｇをトルエン１０
０ｍ１中に入れ、攪拌下ピリジン０．４２ｇとトルエン
１０ｍ１の溶液を滴下した。１５〜２５℃条件下で２時
間攪拌したのち、生成した沈殿物を炉別し、炉液を２０
０ｍ１の水で３回洗浄した。硫酸マグネシウムで乾燥し
、トルエンを留去して１．６ｇの粗生成物を得た。シリ
カゲル８０ｇを用いカラムクロマトグラフィーを行ない
トルエンで溶出して精製し、１．１ｇの生成物を得た。Synthesis of 5-(p-decyloxyphenyl)pyrazine-2-carboxylic acid (2S,3S)-2-chloro-3-methylpentyl ester 5-(p-decyloxyphenyl)pyrazine-2 -2.0 g of carboxylic acid chloride and 0.73 g of (2S,3S)-2-chloro-3-methylpentanol were mixed with 10 g of toluene.
A solution of 0.42 g of pyridine and 10 ml of toluene was added dropwise while stirring. After stirring for 2 hours at 15-25°C, the generated precipitate was separated from the furnace, and the furnace liquid was heated to 20°C.
Washed three times with 0 ml of water. After drying over magnesium sulfate and distilling off the toluene, 1.6 g of crude product was obtained. The product was purified by column chromatography using 80 g of silica gel and eluted with toluene to obtain 1.1 g of product.
Ｉ Ｒ（Ｖｅｍ−’）： １７４０ （Ｃ＝Ｏ）元
素分析値： Ｃ２，Ｈ３９Ｎ２ｏ３Ｃ１として計算値：
Ｃ６Ｂ、２６、ＨＢ、２Ｂ、
Ｎ５．９０ 。I R(Vem-'): 1740 (C=O) elemental analysis value: Calculated value as C2,H39N2o3C1:
C6B, 26, HB, 2B, N5.90.
実測値：Ｃｅｓ、ｏｓ、Ｈ８，１２、 Ｎ５．７０ 。Actual measurements: Ces, os, H8, 12, N5.70.
え１凰１ニユ
実施例１と同様にして、下表１に示す実施例３〜６の液
晶性化合物を得た。In the same manner as in Example 1, liquid crystalline compounds of Examples 3 to 6 shown in Table 1 below were obtained.
実施例１〜６で得た液晶性化合物を、その主要部構造お
よび相転移温度とともに表１に示す。The liquid crystalline compounds obtained in Examples 1 to 6 are shown in Table 1 along with their main structures and phase transition temperatures.
表中、Ｃｒｙｓｔ、は結晶状態、Ｉｓｏ、は等方性液体
、ＳｍＡはスメクチックＡ相、 ＳｍＣ”はカイラルス
メクチックＣ相、そして、Ｓｍ３は相未同定のスメクチ
ック相を、それぞれ表わす。In the table, Cryst represents a crystalline state, Iso represents an isotropic liquid, SmA represents a smectic A phase, SmC'' represents a chiral smectic C phase, and Sm3 represents an unidentified smectic phase.
及五■ユ
実施例１で製造した液晶性化合物を配合成分とする液晶
組成物Ａを調製した。また比較例として実施例１の液晶
性化合物を含有しない液晶組成物Ｂも調製した。各々の
液晶組成物の組成と相転穆温度を示す。A liquid crystal composition A containing the liquid crystal compound produced in Example 1 as a compounding component was prepared. Further, as a comparative example, a liquid crystal composition B not containing the liquid crystal compound of Example 1 was also prepared. The composition and phase transition temperature of each liquid crystal composition are shown.
〈液晶組成物Ａ〉 Ｃｒｙｓｔ、←ＳｍＣ”←Ｓｎ＋Ａ←ｃｈ、←Ｉｓｏ。<Liquid crystal composition A> Cryst, ←SmC”←Sn+A←ch, ←Iso.
く液晶組成物Ｂ〉
Ｃｒｙｓｔ、←ＳｍＣ”←ＳｍＡ ４−Ｃｈ、←Ｉｓｏ
。Liquid crystal composition B> Cryst, ←SmC”←SmA 4-Ch, ←Iso
.
次に液晶組成物Ａ、Ｂ各々の自発分極および応答速度の
測定結果を示す。Next, measurement results of spontaneous polarization and response speed of each of liquid crystal compositions A and B will be shown.
く液晶組成物Ａ〉
温度（ｔ： ） ２５ ３５ ４５
自発分極（ｒ＋ｆ：７ｃｍ”） １８．５ １４．
０ ７．９応答速度（ｍｓｅｃ） ０．１６０
０．０７５ ０．０３８く液晶組成物Ｂ〉
温度（’ｅ） ２５ ３５自発分極（ｎ
Ｃ／ｃｍ’） ２．５ １．９応答速度（ｍｓｅｃ
） １．２８ ０．６９０自発分極は、Ｋ、ミャ
サト外「三角波による強誘電性液晶の自発分極の直接測
定法」 （日本応用物理学会誌ｌユ、１０号、Ｌ （６
６１）１９８３、（“Ｄｉｒｅｃｔ Ｍｅｔｈｏｄ ｗ
ｉｔｈ Ｔｒｉａｎｇｕｌａｒ Ｗａｖｅｓｆｏｒ Ｍ
ｅａｓｕｒｉｎｇ ５ｐｏｎｔａｎｅｏｕｓ Ｐｏ１ａ
ｒｉｚａｔｉｏｎ ＩｎＦｅｒｒｏｅｌｅｃｔｒｉｃ
Ｌｌｑｕｌｄ Ｃｒｙｓｔａｌ” 、 ａｓ ｄｅｓｃ
ｒｉｂａｄｂｙに、Ｍｉｙａｓａｔｏ ｅｔ ａｌ、（
Ｊａｐ、Ｊ、Ａｐｐｌ、Ｐｈｙｓ、２２．Ｎｏ。Liquid crystal composition A> Temperature (t: ) 25 35 45
Spontaneous polarization (r+f: 7cm”) 18.5 14.
0 7.9 Response speed (msec) 0.160
0.075 0.038 Liquid crystal composition B> Temperature ('e) 25 35 Spontaneous polarization (n
C/cm') 2.5 1.9 Response speed (msec
) 1.28 0.690 Spontaneous polarization is K. Myasato et al. "Direct measurement method of spontaneous polarization of ferroelectric liquid crystal using triangular wave" (Journal of Applied Physics Society of Japan, No. 10, L (6
61) 1983, (“Direct Method w
ith Triangular Waves for M
easuring 5pontaneous Po1a
rization InFerroelectric
Llquld Crystal”, as desc
ribadby, Miyasato et al.
Jap, J., Appl, Phys., 22. No.
１０、Ｌ６６１ （１９Ｂ３）））により測定した。10, L661 (19B3))).
また応答速度については、電極を覆うポリイミド被膜に
ラビング処理を施した一対の電極基板問に上記液晶組成
物を挟持し、液晶層厚を２μｍとして、ピーク・トウ・
ピーク電圧として２０Ｖの電圧印加により直交ニコル下
での光学的な応答を検知して応答速度を測定した。Regarding the response speed, the above liquid crystal composition was sandwiched between a pair of electrode substrates on which the polyimide film covering the electrodes had been subjected to a rubbing treatment, and the liquid crystal layer thickness was set to 2 μm.
The response speed was measured by detecting the optical response under crossed Nicols by applying a voltage of 20 V as a peak voltage.
また、前記液晶組成物Ａの応答速度を測定したセルで、
２５℃におけるピーク・トウ・ピーク電圧２０Ｖの電圧
印加時のコントラスト（直交ニコル下）は１３であり、
良好なスイッチング状態が観察された。In addition, in the cell in which the response speed of the liquid crystal composition A was measured,
The contrast (under crossed Nicols) when a voltage of 20 V peak-to-peak voltage is applied at 25° C. is 13,
Good switching conditions were observed.
叉】Ｃ１互
透明電極としてＩ Ｔ Ｏ（Ｉｎｄｉｕｍ Ｔｉｎ ０
ｘｉｄｅ）膜を形成したガラス基板上にポリイミド被膜
を設け、。] ITO (Indium Tin 0
xide) A polyimide film is provided on the glass substrate on which the film is formed.
ラビングにより配向処理を行りた後、ラビング処理軸が
直交するようにしてセルを作製した（セル間隙：８μｍ
）。上記セルにネマチック液晶組成物［リクソンＧＲ−
６３：チッソ（株）製ビフェニル系液晶混合物］を注入
し、ＴＮ（ツィステッドネマチック）型セルとした。こ
のセルを偏光顕微鏡で観察したところリバースドメイン
（しま模様）が生じていることがわかフた。After alignment treatment was performed by rubbing, cells were fabricated with the rubbing axes perpendicular to each other (cell gap: 8 μm).
). A nematic liquid crystal composition [Rixon GR-
63: Biphenyl-based liquid crystal mixture manufactured by Chisso Corporation] was injected to form a TN (twisted nematic) type cell. When this cell was observed using a polarizing microscope, it was found that a reverse domain (striped pattern) was formed.
前記リクソンＧＲ−６３（９９重量部）に対して、本発
明の実施例６の液晶性化合物（１重量部）を加えた液晶
混合物を用い、上記と同様にしてＴＮセルとして、観察
したところ、リバースドメインはみられず、均一性のよ
いネマチック相となっていた。このことから、本発明の
液晶性化合物はリバースドメインの防止に有効であるこ
とがわかった。Using a liquid crystal mixture obtained by adding the liquid crystal compound of Example 6 of the present invention (1 part by weight) to the Rixon GR-63 (99 parts by weight), a TN cell was prepared in the same manner as above and observed. No reverse domain was observed, and a nematic phase with good uniformity was observed. From this, it was found that the liquid crystalline compound of the present invention is effective in preventing reverse domains.
上述したように本発明によれば一般式（Ｉ）で示される
フェニルピラジン誘導体型の液晶性化合物が提供され、
これを配合することにより優れた応答速度および閾値特
性を有する強誘電性カイラルスメクチック液晶組成物な
らびにリバースドメインの発生を防止したネマチック液
晶組成物が得られる。As described above, according to the present invention, a phenylpyrazine derivative-type liquid crystal compound represented by the general formula (I) is provided,
By blending this, a ferroelectric chiral smectic liquid crystal composition with excellent response speed and threshold characteristics and a nematic liquid crystal composition in which the generation of reverse domains is prevented can be obtained.
Claims (1)
式中、Ｒ＿１は炭素数１〜１８のアルキル基、Ｒ＿２は
ハロゲン化アルキル基を示し、Ｘ＿１は−Ｏ−、▲数式
、化学式、表等があります▼、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼または 単結合を示し、Ｘ＿２は▲数式、化学式、表等がありま
す▼、または▲数式、化学式、表等があります▼を示す
。Ｚは▲数式、化学式、表等があります▼または▲数式
、化学式、表等があります▼を示す。）で表わされる液
晶性化合物。 ２、前記一般式（ I ）で示される液晶性化合物におい
て、Ｒ＿２が一般式（ I ａ） ▲数式、化学式、表等があります▼（ I ａ） （但し、式中、Ｒ＿３は直鎖状または分岐状アルキル基
を示し、Ｃ＾＊は不斉炭素原子を示す。ｎは０または１
を示す。） で表わされることを特徴とする特許請求の範囲第１項記
載の液晶性化合物。 ３、一般式（ I ） Ｒ＿１−Ｘ＿１−Ｚ−Ｘ＿２−Ｒ＿２（ I ）（但し、
式中、Ｒ＿１は炭素数１〜１８のアルキル基、Ｒ＿２は
ハロゲン化アルキル基を示し、Ｘ＿１は−Ｏ−、▲数式
、化学式、表等があります▼、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼または 単結合を示し、Ｘ＿２は▲数式、化学式、表等がありま
す▼、または▲数式、化学式、表等があります▼を示す
。Ｚは▲数式、化学式、表等があります▼または▲数式
、化学式、表等があります▼を示す。）で表わされる液
晶性化合物を少なくとも１種含有する液晶組成物。 ４、一般式（ I ） Ｒ＿１−Ｘ＿１−Ｚ−Ｘ＿２−Ｒ＿２（ I ）（但し、
式中、Ｒ＿１は炭素数１〜１８のアルキル基、Ｒ＿２は
ハロゲン化アルキル基を示し、Ｘ＿１は−Ｏ−、▲数式
、化学式、表等があります▼、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼または 単結合を示し、Ｘ＿２は▲数式、化学式、表等がありま
す▼、または▲数式、化学式、表等があります▼を示す
。Ｚは▲数式、化学式、表等があります▼または▲数式
、化学式、表等があります▼を示す。）で表わされる液
晶性化合物を少なくとも１種類含有する液晶組成物を用
いることを特徴とする液晶素子。[Claims] 1. General formula (I) R_1-X_1-Z-X_2-R_2(I) (However,
In the formula, R_1 is an alkyl group having 1 to 18 carbon atoms, R_2 is a halogenated alkyl group, and X_1 is -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ , ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or indicates a single bond, and X_2 indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. Z indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. ) is a liquid crystalline compound represented by 2. In the liquid crystal compound represented by the above general formula (I), R_2 is the general formula (Ia) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(Ia) (However, in the formula, R_3 is a linear or Represents a branched alkyl group, C^* represents an asymmetric carbon atom, n is 0 or 1
shows. ) The liquid crystalline compound according to claim 1, characterized in that it is represented by: 3. General formula (I) R_1-X_1-Z-X_2-R_2(I) (However,
In the formula, R_1 is an alkyl group having 1 to 18 carbon atoms, R_2 is a halogenated alkyl group, and X_1 is -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ , ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or indicates a single bond, and X_2 indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. Z indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. ) A liquid crystal composition containing at least one liquid crystal compound represented by: 4. General formula (I) R_1-X_1-Z-X_2-R_2(I) (However,
In the formula, R_1 is an alkyl group having 1 to 18 carbon atoms, R_2 is a halogenated alkyl group, and X_1 is -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ , ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or indicates a single bond, and X_2 indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. Z indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. ) A liquid crystal element using a liquid crystal composition containing at least one type of liquid crystal compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62277521A JPH01121276A (en) | 1987-11-04 | 1987-11-04 | Liquid crystal compound and liquid crystal composition containing said compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62277521A JPH01121276A (en) | 1987-11-04 | 1987-11-04 | Liquid crystal compound and liquid crystal composition containing said compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01121276A true JPH01121276A (en) | 1989-05-12 |
Family
ID=17584748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62277521A Pending JPH01121276A (en) | 1987-11-04 | 1987-11-04 | Liquid crystal compound and liquid crystal composition containing said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01121276A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5277619A (en) * | 1991-11-08 | 1994-01-11 | Yazaki Corporation | Waterproof connector |
| US5356312A (en) * | 1991-12-09 | 1994-10-18 | Yazaki Corporation | Connector waterproofing stopper |
| US5395266A (en) * | 1991-12-16 | 1995-03-07 | Yazaki Corporation | Water-proofing plug for connector |
| JP2007200639A (en) * | 2006-01-25 | 2007-08-09 | Mitsubishi Cable Ind Ltd | Electrical connector |
| US8177573B2 (en) | 2009-03-05 | 2012-05-15 | Yazaki Corporation | Waterproof plug and wiring harness having the same |
-
1987
- 1987-11-04 JP JP62277521A patent/JPH01121276A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5277619A (en) * | 1991-11-08 | 1994-01-11 | Yazaki Corporation | Waterproof connector |
| US5356312A (en) * | 1991-12-09 | 1994-10-18 | Yazaki Corporation | Connector waterproofing stopper |
| US5395266A (en) * | 1991-12-16 | 1995-03-07 | Yazaki Corporation | Water-proofing plug for connector |
| JP2007200639A (en) * | 2006-01-25 | 2007-08-09 | Mitsubishi Cable Ind Ltd | Electrical connector |
| US8177573B2 (en) | 2009-03-05 | 2012-05-15 | Yazaki Corporation | Waterproof plug and wiring harness having the same |
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