JPH02286653A - Azo compound and liquid crystal composition containing the same - Google Patents
Azo compound and liquid crystal composition containing the sameInfo
- Publication number
- JPH02286653A JPH02286653A JP1104559A JP10455989A JPH02286653A JP H02286653 A JPH02286653 A JP H02286653A JP 1104559 A JP1104559 A JP 1104559A JP 10455989 A JP10455989 A JP 10455989A JP H02286653 A JPH02286653 A JP H02286653A
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- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- formulas
- tables
- compound
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 45
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- -1 Azo compound Chemical class 0.000 title claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000000126 substance Substances 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052763 palladium Inorganic materials 0.000 abstract description 2
- 229910007161 Si(CH3)3 Inorganic materials 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 12
- 239000004988 Nematic liquid crystal Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-NQMVMOMDSA-N (+)-Borneol Natural products C1C[C@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-NQMVMOMDSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical class C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001344 alkene derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- NEHNMFOYXAPHSD-UHFFFAOYSA-N beta-citronellal Natural products O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なアゾ系化合物及び該アゾ系化合物を含
有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel azo compound and a liquid crystal composition containing the azo compound.
従来から、液晶に色素化合物を溶解してなる液晶組成物
を、対向する２枚の電極間に介在させ、色素化合物と液
晶とのゲスト−ホスト効果を利用してカラー表示を行う
ことが知られている。It has been known that a liquid crystal composition made by dissolving a dye compound in liquid crystal is interposed between two opposing electrodes, and color display is performed by utilizing the guest-host effect between the dye compound and the liquid crystal. ing.
そのような液晶組成物に使用される色素は、特に、二色
性比が高いこと、液晶に対して高い溶解性を有すること
等の性質を有することが必要である。The dye used in such a liquid crystal composition is particularly required to have properties such as a high dichroic ratio and high solubility in the liquid crystal.
しかしながら、本発明者等の検討によれば、従来公知の
アゾ系化合物は、必ずしも前記のような液晶組成物で使
用する色素に要求されるような性質を満足するものでは
ないことが分かった。However, according to studies conducted by the present inventors, it has been found that conventionally known azo compounds do not necessarily satisfy the properties required of dyes used in liquid crystal compositions as described above.
したがって、本発明の目的は、高い二色性比と液晶に対
して高い溶解性を示す新規なアゾ系化合物、及びそれを
用いた液晶組成物を提供することにある。Therefore, an object of the present invention is to provide a novel azo compound that exhibits a high dichroic ratio and high solubility in liquid crystals, and a liquid crystal composition using the same.
本発明者等は、上記のような従来の技術に鑑み、−層優
れた特性を有する色素の開発について鋭意検討した結果
、二色性が特に優れ、溶解性も良好な色素を見出し、本
発明を完成するに至った。In view of the above-mentioned conventional technology, the inventors of the present invention have conducted extensive studies on the development of dyes with excellent layer characteristics, and have discovered a dye with particularly excellent dichroism and good solubility, and have developed the present invention. I was able to complete it.
本発明のアゾ系化合物は、下記一般式（１）（Σ は、
それぞれり１）ハロゲン原子もしくはアルキル基で置換
されていてもよいフェニレン基、＜２）
１３）
で示される二価の基を示し、Ｒ１はアルキル基アルコキ
シ基を示し、Ｒ２は、それぞれアルキル基を示す）、
／
アルキル基を示し、Ｒ６は水素原子、アルキル基キル基
と結合して含窒素脂肪族環を形成してもよい〕
で表わされる。The azo compound of the present invention has the following general formula (1) (Σ is
Each 1) a phenylene group optionally substituted with a halogen atom or an alkyl group, <2)
13) Represents a divalent group represented by R1 represents an alkyl group, alkoxy group, R2 represents an alkyl group), / represents an alkyl group, and R6 represents a hydrogen atom, an alkyl group bonded to a kyl group, may form a nitrogen-containing aliphatic ring].
また、本発明の液晶組成物は、上記一般式（Ｉ）で表わ
されるアゾ系化合物を含有することを特徴とする。Further, the liquid crystal composition of the present invention is characterized by containing an azo compound represented by the above general formula (I).
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明のアゾ系化合物において、上記一般式（Ｉ）中、
Ｒ１て表わされるアルキル基及びＲ２におけるＲ３ 、
Ｒ４、Ｒ５及びＲ６て表わされるアルキル基としては、
例えば炭素数１〜ＩＯのアルキル基があげられる。Ｒ１
て表わされるアルコキシ基及びＲ２におけるＲ６て表わ
されるアルコキシ基としては、例えば、炭素数１〜１０
のアルコキシ基があげられる。In the azo compound of the present invention, in the general formula (I),
an alkyl group represented by R1 and R3 in R2,
As the alkyl group represented by R4, R5 and R6,
For example, an alkyl group having 1 to 10 carbon atoms may be mentioned. R1
Examples of the alkoxy group represented by R2 and the alkoxy group represented by R6 in R2 include those having 1 to 10 carbon atoms.
Examples include alkoxy groups.
が置換基としてハロゲン原子又はアルキル基を有するフ
ェニレン基である場合、ハロゲン原子としでは塩素原子
又はフッ素原子があげられ、アルキル基としては、メチ
ル基、エチル基等の低級アルキル基があげられ、例えば
、アルキル置換フェニレン基の場合についての具体例と
しては、アルキル基と、
Ｒ２における
ＣＨ。When is a phenylene group having a halogen atom or an alkyl group as a substituent, examples of the halogen atom include a chlorine atom or a fluorine atom, and examples of the alkyl group include lower alkyl groups such as a methyl group and an ethyl group. , alkyl-substituted phenylene group, an alkyl group, and CH in R2.
／
／
Ｎ
又は−Ｎ
の置換基であるＲ３、Ｒ４又はＲ５のアルキル基とが結
合して含窒素脂肪族環を形成する具体例としては、
ＣＨ３
等をあげることができる。/ / As a specific example of the alkyl group of R3, R4 or R5 which is a substituent of N or -N bonding to form a nitrogen-containing aliphatic ring, CH3 etc. can be mentioned.
前記一般式（Ｉ）で示される化合物は、例えば、次の方
法により合成することができる。The compound represented by the general formula (I) can be synthesized, for example, by the following method.
（上記の■〜■の反応式におけるＲ１ 、（Ｅ）Ｒ２は
、それぞれ前記一般式（Ｉ）におけると同意義を示し、
Ｘは臭素原子、ヨウ素原子などのハロゲン原子を示す）
上記■および■の反応は、ジエチルアミン、トリエチル
アミン、トリーｎ−ブチルアミン等の存在下、ジクロロ
ビス（トリフェニルホスフィン）パラジウム、酢酸パラ
ジウム等のパラジウム系触媒を用い、必要に応じ、ベン
ゼン、トルエン、クロロベンゼン、オルトジクロロベン
ゼン等の溶媒を使用して０〜１５０℃、好ましくは２０
〜１００℃の温度条件下で実施することができる。(R1 and (E)R2 in the above reaction formulas ■ to ■ each have the same meaning as in the general formula (I),
(X represents a halogen atom such as a bromine atom or an iodine atom) The reactions in (1) and (2) above are carried out using a palladium-based catalyst such as dichlorobis(triphenylphosphine)palladium or palladium acetate in the presence of diethylamine, triethylamine, tri-n-butylamine, etc. and, if necessary, a solvent such as benzene, toluene, chlorobenzene, orthodichlorobenzene, at 0 to 150°C, preferably at 20°C.
It can be carried out under temperature conditions of ~100°C.
上記■および■の反応は、Ｎ−メチルピロリドン、Ｎ、
Ｎ−ジメチルホルムアミド、ジオキサン、テ］・ラヒド
ロフラン、メタノール、エタノール、イソプロパツール
等の溶媒中、水の存在下又は不存在下、水酸化ナトリウ
ム、水酸化カリウム等のアルカリで０〜７０℃、好まし
くは１０〜４０℃の温度条件下で処理することにより実
施することができる。The reactions of (1) and (2) above involve N-methylpyrrolidone, N,
In a solvent such as N-dimethylformamide, dioxane, te]-rahydrofuran, methanol, ethanol, isopropanol, etc., in the presence or absence of water, with an alkali such as sodium hydroxide or potassium hydroxide, preferably at 0 to 70°C. This can be carried out by processing at a temperature of 10 to 40°C.
また、本発明のアゾ系化合物は、各種の液晶に混合し、
液晶組成物として使用される。Further, the azo compound of the present invention can be mixed with various liquid crystals,
Used as a liquid crystal composition.
本発明の液晶組成物において、液晶としてはネマチック
液晶、コレステリック液晶、スメクチック液晶のいずれ
を使用することもできる。In the liquid crystal composition of the present invention, any of nematic liquid crystal, cholesteric liquid crystal, and smectic liquid crystal can be used as the liquid crystal.
本発明で用いるネマチック液晶としては、動作温度範囲
でネマチック状態を示すものであれば、かなり広い範囲
で選択することができる。また、このようなネマチック
液晶に、後述の旋光性物質を加えることにより、コレス
テリック状態をとらせることができる。ネマチック液晶
の例としては、下記第１表に示される物質、あるいはこ
れ等の誘導体があげられる。The nematic liquid crystal used in the present invention can be selected from a wide range as long as it exhibits a nematic state within the operating temperature range. Further, by adding an optically active substance to be described later to such a nematic liquid crystal, it can be made to take a cholesteric state. Examples of nematic liquid crystals include the substances shown in Table 1 below, or derivatives thereof.
第
表
（続き）
（続き）
上記第１表中 Ｒｌ はアルキル基又はアルコキシ基を
表わし、Ｒはアルキル基を表わし、Ｘ′はアルキル基、
アルコキシ基、ニトロ基、シアノ基又はハロゲン原子を
表わす。Table (Continued) (Continued) In Table 1 above, Rl represents an alkyl group or an alkoxy group, R represents an alkyl group, X' represents an alkyl group,
Represents an alkoxy group, nitro group, cyano group or halogen atom.
本発明の液晶組成物で用いるホスト液晶物質としては、
第１表に示される液晶又はそれ等の混合物のいずれでも
よいが、例えば、メルク社からＺＬＩ−１１３２という
商品名で販売されている液晶及びＺＬＩ−１５６５とい
う商品名で販売されている液晶、又はＢｒ１ｔｉｓｈ
Ｄｒｕｇ Ｈｏｕｓｅ社からＥ−７という商品名で販売
されている液晶が使用される。The host liquid crystal substance used in the liquid crystal composition of the present invention includes:
Any of the liquid crystals shown in Table 1 or a mixture thereof may be used, such as the liquid crystal sold by Merck under the trade name ZLI-1132 and the liquid crystal sold under the trade name ZLI-1565, or Br1tish
A liquid crystal sold by Drug House under the trade name E-7 is used.
また、このようなネマチック液晶に、以下の旋光性物質
を加えることにより、コレステリック状態をとらせるこ
とができる。Moreover, by adding the following optically active substance to such a nematic liquid crystal, it can be made to take a cholesteric state.
本発明の液晶組成物に用いる旋光性物質としては、カイ
ラルネマチック化合物、例えば、２−メチルブチル基、
３−メチルブトキシ基、３−メチルペンチル基、３−メ
チルペントキシ基、４−メチルヘキシル基、４−メチル
へキトキシ基等の光学活性基をネマチック液晶に導入し
た化合物が挙げられる。また、特開昭５１−４５５４８
号公報に示されるｇ−メントール、ｄ−ボルネオール等
のアルコール誘導体、ｄ−ショウノウ、３−メチルシク
ロヘキサン等のケトン誘導体、ｄ−シトロネル酸、ｐ−
ショウノウ酸等のカルボン酸誘導体、ｄ−シトロネラー
ル等のアルデヒド誘導体、ｄ−リノネン等のアルケン誘
導体、その他のアミン、アミド、ニトリル誘導体等の光
学活性物質を使用することができる。As the optically active substance used in the liquid crystal composition of the present invention, chiral nematic compounds such as 2-methylbutyl group,
Examples include compounds in which optically active groups such as 3-methylbutoxy, 3-methylpentyl, 3-methylpentoxy, 4-methylhexyl, and 4-methylhexyl groups are introduced into nematic liquid crystals. Also, JP-A-51-45548
Alcohol derivatives such as g-menthol and d-borneol, ketone derivatives such as d-camphor and 3-methylcyclohexane, d-citronel acid, p-
Optically active substances such as carboxylic acid derivatives such as camphoric acid, aldehyde derivatives such as d-citronellal, alkene derivatives such as d-linonene, and other amine, amide, and nitrile derivatives can be used.
更に、本発明で用いるスメクチック液晶としては、スメ
クチックＡ液晶、スメクチックカイラルＣ液晶があげら
れる。Further, examples of the smectic liquid crystal used in the present invention include smectic A liquid crystal and smectic chiral C liquid crystal.
本発明の液晶組成物を使用して液晶表示を行うための素
子としては、公知の液晶表示用素子を使用することがで
きる。即ち、一般に少なくとも一方が透明な二枚のガラ
ス基板上に任意のパターンの透明電極を設け、電極面が
対向するように適当なスペーサーを介して、二枚のガラ
ス基板が平行になるように素子を構成したものが用いら
れる。As an element for performing liquid crystal display using the liquid crystal composition of the present invention, a known liquid crystal display element can be used. That is, generally, transparent electrodes in an arbitrary pattern are provided on two glass substrates, at least one of which is transparent, and the device is placed so that the two glass substrates are parallel to each other with a suitable spacer interposed so that the electrode surfaces face each other. A configuration consisting of the following is used.
この場合、スペーサーにより素子のギャップが決められ
る。素子ギャップとしては１〜１００ ａｎ、特に２〜
５０帆が実用的見地から好ましい。In this case, the spacer determines the gap between the elements. The element gap is 1 to 100 an, especially 2 to 100 an
50 sails is preferred from a practical standpoint.
以下、本発明を実施例により更に具体的に説明するが、
本発明はこれ等実施例により限定されるものではない。Hereinafter, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to these examples.
なお、二色性を示すオーダー・パラメーターについて簡
単に説明すれば、色素化合物のオーダー・パラメーター
（Ｓ）は、実験的には次式（１）から求められる。In addition, to briefly explain the order parameter indicating dichroism, the order parameter (S) of the dye compound can be experimentally determined from the following formula (1).
Ａ／−Ａ±
（Ｓ）−（１）
２Ａ土十Ａ／
ここでＡ〆及びＡ土は、それぞれ液晶の配向方向に対し
て平行及び垂直に偏光した光に対する色素の吸光度であ
る。A/-A± (S)-(1) 2A soil 1 A/ Here, A〆 and A soil are the absorbances of the dye for light polarized parallel and perpendicular to the alignment direction of the liquid crystal, respectively.
オーダー・パラメーター（Ｓ）は、具体的にはゲスト・
ホスト型液晶素子の表示コントラストを示す値であり、
この値が理論上１に近付くほど、白ぬけ部分の残色度が
減少し、明るくコントラストの大きい鮮明な表示が可能
となる。Specifically, the order parameter (S) is
This is a value that indicates the display contrast of a host type liquid crystal element.
Theoretically, as this value approaches 1, the degree of residual color in white areas decreases, allowing for brighter, clearer display with greater contrast.
（ｎ） 実施例１ の合成 下記化合物１００ ｍｇ。(n) Example 1 synthesis of 100 mg of the following compound.
ヨウ化第１銅６■、下記構造式で示される化合物８ｍｇ
（ｎ） Ｈ＋＋Ｃｓ ＜Σｃ＝ｃｕ
及びトリエチルアミン８０ｍｇを、オルトジクロルベン
ゼン３０−に加え、窒素を流しつつ５０℃に加熱した。6 ml of cuprous iodide, 8 mg of a compound represented by the following structural formula (n) H++Cs <Σc=cu, and 80 mg of triethylamine were added to 30- orthodichlorobenzene and heated to 50° C. while flowing nitrogen.
このなかに、ジクロロビス（トリフェニルホスフィン）
パラジウム３ＩＩ１ｇ及びトリフェニルホスフィン３
ｍｇを加え、更に、５０℃にて３時間加熱撹拌した。オ
ルトジクロルベンゼンを減圧下に留去し、残渣をシリカ
ゲルを担体とし、クロロホルムを分離溶媒とするカラム
クロマトグラフィーにて分離精製して、上記目的の化合
物９０ｍｇを得た。融点は１６６〜１６７°Ｃであった
。Among these, dichlorobis(triphenylphosphine)
Palladium 3II 1g and triphenylphosphine 3
mg was added thereto, and the mixture was further heated and stirred at 50°C for 3 hours. Orthodichlorobenzene was distilled off under reduced pressure, and the residue was separated and purified by column chromatography using silica gel as a carrier and chloroform as a separation solvent to obtain 90 mg of the desired compound. The melting point was 166-167°C.
得られた本発明のアゾ系化合物（色素）を、前述の混合
液晶ＺＬＩ−１５６５（メルク社商品名）に添加し、７
０℃以上に加熱して、液晶が等方性液体になった状態で
よくかきまぜた後、放置冷却する工程を繰り返して行い
、上記化合物（色素）を溶解して、液晶組成物を調製し
た。The obtained azo compound (dye) of the present invention was added to the above-mentioned mixed liquid crystal ZLI-1565 (trade name of Merck & Co., Ltd.), and 7
A liquid crystal composition was prepared by heating to 0° C. or higher, stirring well in a state in which the liquid crystal became an isotropic liquid, and then leaving to cool. The above compound (dye) was dissolved and a liquid crystal composition was prepared.
このようにして得られた本発明の液晶組成物を、透明電
極を有し、液晶と接する面にポリアミド系樹脂を塗布硬
化後ラビングしてホモジニアス配向処理を施した上下二
枚のガラス基板からなる基板間ギャップｌＯ如の素子に
封入した。上記配向処理を施した素子内では、電圧無印
加のとき、上記液晶はホモジニアス配向状憇をとり、色
素分子もホスト液晶にしたがって同様の配向をとるもの
であった。The liquid crystal composition of the present invention thus obtained is made up of two glass substrates, an upper and lower glass substrate, each having a transparent electrode and a homogeneous alignment treatment performed by coating a polyamide resin on the surface in contact with the liquid crystal, curing the composition, and then rubbing it. It was sealed in a device with an inter-substrate gap of lO. In the device subjected to the above alignment treatment, when no voltage was applied, the liquid crystal assumed a homogeneous alignment, and the dye molecules also assumed a similar alignment according to the host liquid crystal.
このようにして作製したゲスト・ホスト素子の吸収スペ
クトルの測定を、液晶分子の配向方向に対して平行に偏
光した光及び垂直に偏光した光の各々を用いて行い、こ
れ等各個光に対する色素の最大吸収波長を求めた。色素
の吸光度を求めるにあたっては、ホスト液晶及びガラス
基板による吸収と、素子の反射損失に関して補正を行っ
た。The absorption spectrum of the guest-host device thus prepared was measured using light polarized parallel to and perpendicular to the alignment direction of the liquid crystal molecules, and The maximum absorption wavelength was determined. In determining the absorbance of the dye, corrections were made for absorption by the host liquid crystal and glass substrate and reflection loss of the element.
また、各偏光に対するＡ／及びＡ工を用い、前記式（１
）から、オーダー・パラメーター（Ｓ）の値を算出した
。In addition, using A/ and A factor for each polarized light, the above formula (1
), the value of the order parameter (S) was calculated.
以上の結果を後記第２表のＮｏ、 １に示す。The above results are shown in No. 1 in Table 2 below.
実施例２
実施例１と同様な操作により、下記第２表に示す化合物
を製造した。そのオーダー・パラメーター（Ｓ）及び最
大吸収波長を測定し、あわせて第２表にその結果を示す
。Example 2 In the same manner as in Example 1, the compounds shown in Table 2 below were produced. The order parameter (S) and maximum absorption wavelength were measured, and the results are also shown in Table 2.
本発明の新規なアゾ系化合物は、高い二色性比及び液晶
に対して高い溶解性を示し、それを用いて得られる本発
明の液晶組成物は、良好なカラー表示を行うことができ
る。The novel azo compound of the present invention exhibits a high dichroic ratio and high solubility in liquid crystal, and the liquid crystal composition of the present invention obtained using the same can provide good color display.
Claims (2)
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▼及び▲数
式、化学式、表等があります▼は、それぞれ、（１）ハ
ロゲン原子もしくはアルキル基で置換されていてもよい
フェニレン基、式 ▲数式、化学式、表等があります▼（２）または▲数式
、化学式、表等があります▼（３） で示される二価の基を示し、Ｒ＾１はアルキル基又はア
ルコキシ基を示し、Ｒ＾２は、それぞれ▲数式、化学式
、表等があります▼（但し、Ｒ＾３及びＲ＾４は、それ
ぞれアルキル基を示す）、 ▲数式、化学式、表等があります▼（Ｒ＾５は水素原子
又は アルキル基を示し、Ｒ＾６は水素原子、アルキル基又は
アルコキシ基を示す）、▲数式、化学式、表等がありま
す▼又は ▲数式、化学式、表等があります▼を示し、更に、▲数
式、化学式、表等があります▼における置 換基のアルキル基は、Ｒ＾３、Ｒ＾４又はＲ＾５のアル
キル基と結合して含窒素脂肪族環を形成してもよい〕 で表わされるアゾ系化合物。(1) General formula below (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ are respectively (1) halogen atoms or Indicates a phenylene group that may be substituted with an alkyl group, a divalent group represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (3), R^1 represents an alkyl group or an alkoxy group, R^2 each has a ▲ mathematical formula, chemical formula, table, etc. ▼ (However, R^3 and R^4 each represent an alkyl group), ▲ Numerical formula, There are chemical formulas, tables, etc. ▼ (R^5 indicates a hydrogen atom or an alkyl group, R^6 indicates a hydrogen atom, alkyl group, or alkoxy group), ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Numerical formulas, There are chemical formulas, tables, etc. ▼, and furthermore, the alkyl group of the substituent in ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼ is a nitrogen-containing may form an aliphatic ring].
るアゾ系化合物を含有することを特徴とする液晶組成物
。(2) A liquid crystal composition containing an azo compound represented by the general formula (I) according to claim (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1104559A JP2719955B2 (en) | 1989-04-26 | 1989-04-26 | Azo-based compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1104559A JP2719955B2 (en) | 1989-04-26 | 1989-04-26 | Azo-based compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02286653A true JPH02286653A (en) | 1990-11-26 |
| JP2719955B2 JP2719955B2 (en) | 1998-02-25 |
Family
ID=14383818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1104559A Expired - Fee Related JP2719955B2 (en) | 1989-04-26 | 1989-04-26 | Azo-based compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2719955B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010047775A (en) * | 2004-12-31 | 2010-03-04 | Ind Technol Res Inst | Dichroic dye, dye composition thereof, microencapsulated liquid crystal composition including dichroic dye, liquid crystal composition and liquid crystal display device |
| WO2017002792A1 (en) * | 2015-07-02 | 2017-01-05 | Dic株式会社 | Liquid crystal composition and liquid crystal display element using same |
| JP2017025125A (en) * | 2015-07-15 | 2017-02-02 | 三菱化学株式会社 | Novel azo-based dichroic dye, and liquid crystal composition and liquid crystal element comprising the azo-based dichroic dye |
-
1989
- 1989-04-26 JP JP1104559A patent/JP2719955B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010047775A (en) * | 2004-12-31 | 2010-03-04 | Ind Technol Res Inst | Dichroic dye, dye composition thereof, microencapsulated liquid crystal composition including dichroic dye, liquid crystal composition and liquid crystal display device |
| WO2017002792A1 (en) * | 2015-07-02 | 2017-01-05 | Dic株式会社 | Liquid crystal composition and liquid crystal display element using same |
| JPWO2017002792A1 (en) * | 2015-07-02 | 2017-06-29 | Dic株式会社 | Liquid crystal composition and liquid crystal display device using the same |
| CN107636115A (en) * | 2015-07-02 | 2018-01-26 | Dic株式会社 | Liquid-crystal composition and use its liquid crystal display cells |
| JP2017025125A (en) * | 2015-07-15 | 2017-02-02 | 三菱化学株式会社 | Novel azo-based dichroic dye, and liquid crystal composition and liquid crystal element comprising the azo-based dichroic dye |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2719955B2 (en) | 1998-02-25 |
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