JP2719954B2 - Azo-based compound and liquid crystal composition containing the same - Google Patents
Azo-based compound and liquid crystal composition containing the sameInfo
- Publication number
- JP2719954B2 JP2719954B2 JP1091833A JP9183389A JP2719954B2 JP 2719954 B2 JP2719954 B2 JP 2719954B2 JP 1091833 A JP1091833 A JP 1091833A JP 9183389 A JP9183389 A JP 9183389A JP 2719954 B2 JP2719954 B2 JP 2719954B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- alkyl group
- crystal composition
- group
- present
- 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 - Fee Related
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 41
- 239000000203 mixture Substances 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 title description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- -1 azo compound Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000975 dye Substances 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 239000000758 substrate Substances 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000013543 active substance Substances 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
- 239000011521 glass Substances 0.000 description 2
- 239000002904 solvent Substances 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 compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-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
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- JSCFDMNXBTVUTH-UHFFFAOYSA-N 4-[(4-iodophenyl)diazenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=C(I)C=C1 JSCFDMNXBTVUTH-UHFFFAOYSA-N 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
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-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
- 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling 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
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 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
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium 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
- 230000010287 polarization Effects 0.000 description 1
- 229920006122 polyamide resin Polymers 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
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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。Description: TECHNICAL FIELD 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。Conventionally, it has been known that a liquid crystal composition obtained by dissolving a dye compound in a liquid crystal is interposed between two opposing electrodes, and color display is performed using a 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。Dyes used in such a liquid crystal composition need to have properties such as a high dichroic ratio and a high solubility in liquid crystals.
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 the study by the present inventors, it has been found that conventionally known azo compounds do not always satisfy the properties required for the dyes used in the liquid crystal composition 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 exhibiting 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、一層
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。The present inventors have, in view of the conventional techniques as described above, as a result of intensive studies on the development of a dye having more excellent properties, have found a dye with particularly excellent dichroism and good solubility,
The present invention has been completed.
本発明のアゾ系化合物は、下記一般式（Ｉ） は、それぞれハロゲン原子又はアルキル基で置換されて
いてもよい下記（１）、（２）または（３）で示される
二価の基を示し、 R1及びR2は、それぞれ （但し、R3及びR4は、それぞれアルキル基を示す）、 （R5は水素原子又はアルキル基を示し、R6は水素原子、
アルキル基又はアルコキシ基を示す）、 における置換基のアルキル基は、R3、R4又はR5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。The azo compound of the present invention has the following general formula (I) Represents a divalent group represented by the following (1), (2) or (3), each of which may be substituted with a halogen atom or an alkyl group; R 1 and R 2 are each (However, R 3 and R 4 each represent an alkyl group), (R 5 represents a hydrogen atom or an alkyl group, R 6 represents a hydrogen atom,
Represents an alkyl group or an alkoxy group), The alkyl group of the substituent may be bonded to the alkyl group of R 3 , R 4 or R 5 to 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 the azo compound represented by the general formula (I).
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明のアゾ系化合物において、上記一般式（Ｉ）
中、R1およびR2におけるR3、R4、R5及びR6で表わされる
アルキル基としては、例えば炭素数１〜10のアルキル基
があげられる。In the azo compound of the present invention, the above-mentioned general formula (I)
In the above, examples of the alkyl group represented by R 3 , R 4 , R 5 and R 6 in R 1 and R 2 include an alkyl group having 1 to 10 carbon atoms.
R6で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。Examples of the alkoxy group represented by R 6 include an alkoxy group having 1 to 10 carbon atoms.
が置換基としてハロゲン原子又はアルキル基を有する場
合、ハロゲン原子として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、 等があげられる。また の置換基であるアルキル基と、−R2における 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、 等をあげることができる。 Has 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 a lower alkyl group such as a methyl group and an ethyl group. As a specific example of the case of the group, And the like. Also The alkyl group is a substituent, the -R 2 Specific examples of forming a nitrogen-containing aliphatic ring by bonding with an alkyl group of R 3 , R 4 or R 5 which is a substituent of Etc. can be given.
前記一般式（Ｉ）で示される化合物は、例えば、次の
Ａ法又はＢ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 A or Method B.
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Ａ法及びＢ法は共に、ジエチルアミン、トリエチ
ルアミン、トリ−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20〜1
00℃の温度条件下で実施することができる。 R 2 has the same meaning as in the general formula (I), and X represents a halogen atom such as a bromine atom or an iodine atom.) In both the methods A and B, diethylamine, triethylamine, tri-n-butylamine In the presence of, for example, dichlorobis (triphenylphosphine) palladium, using a palladium catalyst such as palladium acetate, if necessary, using a solvent such as benzene, toluene, chlorobenzene, ortho dichlorobenzene, 0 to 150 ℃, preferably 20-1
It can be carried out under a temperature condition of 00 ° C.
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。The azo compound of the present invention is mixed with various liquid crystals and 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 a nematic liquid crystal, a cholesteric liquid crystal and a 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 in a fairly wide range as long as it exhibits a nematic state in an operating temperature range. Further, a cholesteric state can be obtained by adding an optically rotatory substance described later to such a nematic liquid crystal. Examples of the nematic liquid crystal include the substances shown in Table 1 below and derivatives thereof.
上記第１表中、Ｒ′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。 In the above Table 1, R 'represents an alkyl group or an alkoxy group, R represents an alkyl group, X' represents an alkyl group,
Represents an alkoxy group, a nitro group, a cyano group or a 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、トルク社から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British 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 may be any of the liquid crystals shown in Table 1 or a mixture thereof.For example, liquid crystals sold under the trade name ZLI-1132 by Torque and The liquid crystal sold under the trade name ZLI-1565 or the liquid crystal sold under the trade name E-7 from British Drug House 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。Further, a cholesteric state can be obtained by adding the following optically active substance to such a nematic liquid crystal.
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
チルヘキトキシ基等の光学活性基をネマチック液晶に導
入した化合物がげられる。また、特開昭51−45546号公
報に示されるｌ−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、ｌ−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 optical rotatory substance used in the liquid crystal composition of the present invention, a chiral nematic compound such as a 2-methylbutyl group, a 3-methylbutoxy group, a 3-methylpentyl group,
Compounds in which optically active groups such as -methylpentoxy group, 4-methylhexyl group and 4-methylhexoxy group are introduced into nematic liquid crystal are obtained. Also, alcohol derivatives such as l-menthol and d-borneol, ketone derivatives such as d-camphor and 3-methylcyclohexane, and carboxyls such as d-citronellic acid and 1-camphoric acid described in JP-A-51-45546. Optically active substances such as acid derivatives, aldehyde derivatives such as d-citronellal, alkene derivatives such as d-linonene, and other amines, amides, 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, the smectic liquid crystal used in the present invention includes a smectic A liquid crystal and a 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。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１〜100μｍ、特に
２〜50μｍが実用的見地から好ましい。As a device for performing liquid crystal display using the liquid crystal composition of the present invention, a known liquid crystal display device can be used. That is, generally, a transparent electrode of an arbitrary pattern is provided on two glass substrates, at least one of which is transparent. Is used. In this case, the gap of the element is determined by the spacer. The element gap is preferably 1 to 100 μm, particularly preferably 2 to 50 μm from a practical viewpoint.
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 described more specifically with reference to examples, but 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。The order parameter indicating dichroism will be briefly described. The order parameter (S) of the dye compound is experimentally obtained from the following equation (1).
ここでＡ及びＡ⊥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。 Here, A and A⊥ are the absorbances of the dye with respect to 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。The order parameter (S) is, specifically, a value indicating the display contrast of the guest-host type liquid crystal element. As this value approaches 1 theoretically, the residual color degree of the white portion decreases, and the contrast becomes brighter. And a clear display with a large size can be realized.
実施例１ 下記化合物69mg、 ヨウ化第１銅6mg、４′−ヨウド−４−ジメチルアミノ
アゾベンゼン45mg及びトリエチルアミン150mgを、オル
トジクロルベンゼン30mlに加え、窒素を流しつつ50℃に
加熱した。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3.3mg及びトリフェニルホスフィ
ン2.2mg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、上記目的のア
ゾ化合物45mgを得た。融点は249〜250℃であった。Example 1 69 mg of the following compound, 6 mg of cuprous iodide, 45 mg of 4'-iodo-4-dimethylaminoazobenzene and 150 mg of triethylamine were added to 30 ml of orthodichlorobenzene and heated to 50 ° C. while flowing nitrogen. To this, 3.3 mg of dichlorobis (triphenylphosphine) palladium and 2.2 mg of triphenylphosphine were added, 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 45 mg of the desired azo compound. Melting point was 249-250 ° C.
得られた本発明のアゾ化合物（色素）を、前述の混合
液晶ZLI−1565（メルク社商品名）に添加し、70℃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、上記ア
ゾ化合物（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 is added to the above-mentioned mixed liquid crystal ZLI-1565 (trade name of Merck) and heated to 70 ° C. or more, and the liquid crystal may be in an isotropic liquid state. After stirring, the process of standing and cooling was repeated to dissolve the azo compound (dye) to prepare a liquid crystal composition.
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10μｍ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態をとり、
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 has a transparent electrode, a polyamide resin is applied to the surface in contact with the liquid crystal, and is hardened and rubbed. The device was sealed in a device having a gap between substrates of 10 μm. In the element subjected to the above alignment treatment, when no voltage is applied, the liquid crystal takes a homogeneous alignment state,
The dye molecules had the same orientation according to the host liquid crystal.
このようにして作成したゲスト・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、これ等
各偏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 the light polarized parallel to the orientation direction of the liquid crystal molecules and the light polarized vertically, and the maximum absorption of the dye for each of these polarizations was measured. The wavelength was determined. In determining the absorbance of the dye, correction was made for the absorption by the host liquid crystal and the glass substrate and the reflection loss of the device.
また、各偏光に対するＡ及びＡ⊥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。The value of the order parameter (S) was calculated from the above equation (1) using A and A 及 び for each polarized light.
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 of 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 the maximum absorption wavelength were measured, and the results are shown in Table 2.
〔発明の効果〕 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。 [Effects of the Invention] The novel azo compound of the present invention exhibits a high dichroic ratio and high solubility for liquid crystals, and the liquid crystal composition of the present invention obtained using the compound exhibits good color display. It can be carried out.
───────────────────────────────────────────────────── 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 Ｇ０２Ｆ 1/13 ５００ Ｇ０２Ｆ 1/13 ５００ ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification number Agency reference number FI Technical display location G02F 1/13 500 G02F 1/13 500
Claims (2)
いてもよい下記（１）、（２）または（３）で示される
二価の基を示し、 R1及びR2は、それぞれ （但し、R3及びR4は、それぞれアルキル基を示す）、 （R5は水素原子又はアルキル基を示し、R6は水素原子、
アルキル基又はアルコキシ基を示す）、 における置換基のアルキル基は、R3、R4又はR5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. The following general formula Represents a divalent group represented by the following (1), (2) or (3), each of which may be substituted with a halogen atom or an alkyl group; R 1 and R 2 are each (However, R 3 and R 4 each represent an alkyl group), (R 5 represents a hydrogen atom or an alkyl group, R 6 represents a hydrogen atom,
Represents an alkyl group or an alkoxy group), And the alkyl group of the substituent may be bonded to an alkyl group of R 3 , R 4 or R 5 to form a nitrogen-containing aliphatic ring.]
され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 comprising the azo compound represented by the general formula (I) according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1091833A JP2719954B2 (en) | 1989-04-13 | 1989-04-13 | Azo-based compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1091833A JP2719954B2 (en) | 1989-04-13 | 1989-04-13 | Azo-based compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02270851A JPH02270851A (en) | 1990-11-05 |
| JP2719954B2 true JP2719954B2 (en) | 1998-02-25 |
Family
ID=14037598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1091833A Expired - Fee Related JP2719954B2 (en) | 1989-04-13 | 1989-04-13 | Azo-based compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2719954B2 (en) |
-
1989
- 1989-04-13 JP JP1091833A patent/JP2719954B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02270851A (en) | 1990-11-05 |
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