JPH11343487A - Liquid crystal composition - Google Patents
Liquid crystal compositionInfo
- Publication number
- JPH11343487A JPH11343487A JP14970698A JP14970698A JPH11343487A JP H11343487 A JPH11343487 A JP H11343487A JP 14970698 A JP14970698 A JP 14970698A JP 14970698 A JP14970698 A JP 14970698A JP H11343487 A JPH11343487 A JP H11343487A
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- Prior art keywords
- liquid crystal
- group
- crystal composition
- absorption
- formula
- Prior art date
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Abstract
Description
【０００１】[0001]
【発明の属する利用分野】本発明は液晶表示素子の分野
で有用な二色性色素を含む液晶組成物に関する。The present invention relates to a liquid crystal composition containing a dichroic dye useful in the field of liquid crystal display devices.
【０００２】[0002]
【従来の技術】液晶材料に少量の二色性色素を添加した
組成物は、ゲストホスト（以後ＧＨと称する）と称され
る液晶表示素子に使用される。このＧＨは液晶表示素子
の重要な形式の一つであり、特にカラ−液晶表示素子の
光利用効率を高める方法として着目されている。たとえ
ば、三原色各々のハルマイヤー型ＧＨセルを積層したＧ
Ｈ型液晶表示素子、二色のハルマイヤー型ＧＨセルの間
に偏光板を挿入して積層したＧＨ型液晶表示素子、三原
色各々のＧＨ液晶を二層型または三層型セルで積層した
ＧＨ型液晶表示素子、等の各種ＧＨ型液晶表示素子が注
目されている。近年は特に省エネルギ−や携帯機器に於
ける電池駆動時間の確保の点から反射型の液晶表示素子
が着目されている。反射型の液晶表示素子ではバックラ
イト等の補助光源がないため、光利用効率の高いこれら
ＧＨ型液晶表示素子が有望視されている。2. Description of the Related Art A composition obtained by adding a small amount of dichroic dye to a liquid crystal material is used for a liquid crystal display device called a guest host (hereinafter referred to as GH). This GH is one of the important types of the liquid crystal display element, and is particularly noted as a method for increasing the light use efficiency of the color liquid crystal display element. For example, G in which Halmeier GH cells of each of the three primary colors are stacked
H-type liquid crystal display element, GH-type liquid crystal display element in which a polarizing plate is inserted between two-color Halmier-type GH cells and laminated, GH-type liquid crystal in which three primary color GH liquid crystals are laminated in a two-layer or three-layer cell Various GH type liquid crystal display elements such as liquid crystal display elements have been receiving attention. In recent years, in particular, attention has been paid to a reflection type liquid crystal display device from the viewpoint of energy saving and securing a battery driving time in a portable device. Since a reflection type liquid crystal display element does not have an auxiliary light source such as a backlight, these GH type liquid crystal display elements having high light use efficiency are expected to be promising.
【０００３】一方、ＧＨに使用される二色性色素として
は、これまでアゾ系色素、アントラキノン系色素等で二
色性を有する優れた材料が開発され、これらの材料は多
くの液晶材料中で二色性を示すことが、アレキサンダー
ヴィ． イバシュチェンコ（Ａｌｅｘａｎｄｅｒ
Ｖ． Ｉｖａｓｈｃｈｅｎｋｏ）著、ダイクロイックダ
イズ フォオ リキッドクリスタル ディスプレイズ
（ＤＩＣＨＲＯＩＣ ＤＹＥＳ ｆｏｒ ＬＩＱＵＩＤ
ＣＲＹＳＴＡＬ ＤＩＳＰＬＡＹＳ）第１６５〜３３
７頁、シーアールシープレス（ＣＲＣ Ｐｒｅｓｓ）等
に記載されている。On the other hand, as dichroic dyes used for GH, excellent materials having dichroism such as azo dyes and anthraquinone dyes have been developed, and these materials are used in many liquid crystal materials. To exhibit dichroism, Alexander vie. Alexander Ibashchenko
V. Ivashchenko, Dichroic soy pho liquid crystal displays (DICHROIC DYES for LIQUID)
CRYSTAL DISPLAYS) No. 165-33
7, page C R Press (CRC Press) and the like.
【０００４】しかしながら、二色性色素の吸収スペクト
ル形状と吸光係数は、ＧＨ方式でカラ−表示を行う際に
大きな影響を与える。 すなわち、表示可能な色調を増
やし演色性を確保するためには各原色を独立に制御する
必要があり、吸収波長の重複の少ない色素を組み合わせ
る必要がある。吸収波長の重複により各原色は完全に独
立に制御出来ず、表現できる色の範囲は狭まり、また余
計な吸収によって光利用効率も低下していた。吸収波長
の重複を避けるためには各色の吸収ピ−ク波長の選定も
重要であるが、一般的に色素の吸収ピークは幅広いた
め、吸収ピ−ク波長の選定だけではどうしても幾分かの
重複部分が発生する。そこで、吸収スペクトル形状は重
複部分を減らすために光吸収ピークの波長幅が少しでも
狭い色素が特に有用である。また、十分なコントラスト
を確保するために、二色性色素の吸光係数は大きいほど
好ましい。すなわち、吸光係数の大きな二色性色素は、
わずかな使用量で鮮明な液晶表示素子を提供することが
できるが、吸光係数の小さな二色性色素を使用した場
合、ある一定のコントラストを出すために多くの量の色
素を使用せねばならず、経済的であるとはいえない。従
来のキノン系色素では光吸収の波長幅は比較的狭いもの
の、吸光係数は比較的小さく、アゾ系色素では吸光係数
は比較的大きいものの、光吸収ピークの波長幅は比較的
広い。従来の液晶組成物の中に含まる二色性色素では、
大きな吸光係数と光吸収ピークの波長幅が狭いという特
性を同時に兼ね備えたものは見出せていないのが現状で
ある。However, the shape of the absorption spectrum and the absorption coefficient of the dichroic dye have a significant effect when performing color display by the GH method. That is, in order to increase the displayable color tone and secure the color rendering properties, it is necessary to control each primary color independently, and it is necessary to combine dyes with less overlap of absorption wavelengths. Due to the overlap of absorption wavelengths, each primary color could not be controlled completely independently, the range of colors that could be expressed was narrowed, and light absorption efficiency was reduced due to extra absorption. Although it is important to select the absorption peak wavelength of each color in order to avoid the overlap of the absorption wavelengths, the absorption peak of the dye is generally broad, so that the selection of the absorption peak wavelengths will inevitably result in some overlap. Part occurs. Therefore, a dye having a light absorption peak having a slightly narrower wavelength width is particularly useful for reducing the overlapping portion in the absorption spectrum shape. Further, in order to ensure sufficient contrast, the larger the absorption coefficient of the dichroic dye, the more preferable. That is, a dichroic dye having a large absorption coefficient is
Although a clear liquid crystal display device can be provided with a small amount of use, when a dichroic dye having a small extinction coefficient is used, a large amount of the dye must be used to obtain a certain contrast. It is not economical. Conventional quinone dyes have a relatively narrow wavelength band of light absorption, but have a relatively small extinction coefficient, and azo dyes have a relatively large extinction coefficient, but have a relatively wide wavelength band of light absorption peak. In dichroic dyes contained in conventional liquid crystal compositions,
At present, it has not been found that a material having both a large extinction coefficient and a characteristic that the wavelength width of a light absorption peak is narrow is present.
【０００５】[0005]
【発明が解決しようとする課題】本発明の目的は、吸光
係数が大きく、かつ光吸収ピ−クの波長幅が狭く、同時
に二色性を示す色素を含む液晶組成物を得ることであ
る。SUMMARY OF THE INVENTION It is an object of the present invention to provide a liquid crystal composition containing a dye having a large absorption coefficient, a narrow wavelength band of light absorption peak, and simultaneously exhibiting dichroism.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、上記の課
題を解決すべく鋭意検討を続けた結果、ある種のベンゾ
ジフラノン系化合物が吸光係数が大きく、かつ吸収半値
幅が小さく、同時に二色比を示すことを見出し、本発明
を完成するに至った。すなわち、本発明は、下記一般式
（Ｉ）The present inventors have made intensive studies to solve the above-mentioned problems. As a result, some benzodifuranone-based compounds have a large absorption coefficient and a small absorption half-value width, and They have found that they show a color ratio, and have completed the present invention. That is, the present invention provides the following general formula (I)
【０００７】[0007]
【化２】 Embedded image
【０００８】［式中、ＡおよびＢは、それぞれ独立して
水素原子若しくは少なくとも１つの基で置換されていて
もよい、ベンゼン、ナフタレン、ビフェニル、チオフェ
ン、ベンゾチオフェン、チアゾール、ベンゾチアゾール
またはベンゾイソチアゾールを表し、ｎは０または１の
整数を表す。］で示される二色性色素を少なくとも１つ
含むことを特徴とする液晶組成物に関するものである。Wherein A and B are each independently a hydrogen atom or at least one group which may be substituted with benzene, naphthalene, biphenyl, thiophene, benzothiophene, thiazole, benzothiazole or benzoisothiazole. And n represents an integer of 0 or 1. And a liquid crystal composition comprising at least one dichroic dye represented by the formula:
【０００９】[0009]
【発明の実施の形態】本発明において、一般式（Ｉ）に
おけるＡおよびＢ上の置換基の中、置換されていてもよ
い基としては、水酸基、置換されていてもよい、Ｃ１〜
Ｃ１２アルキル基、Ｃ１〜Ｃ１２アルコキシ基、Ｃ１〜
Ｃ１２アルコキシＣ１〜Ｃ１２アルキル基、Ｃ１〜Ｃ１
２アルキルカルボニル基、Ｃ１〜Ｃ１２アルコキシカル
ボニルＣ１〜Ｃ１２アルキル基、フェニルアルキル基若
しくはＣ１〜Ｃ１２アルコキシＣ１〜Ｃ１２アルコキシ
カルボニルＣ１〜Ｃ１２アルキル基、あるいは−Ｏ−Ｒ
1−Ｑ（ここで、Ｒ1はメチレン基またはＣ１〜Ｃ１２ア
ルキルカルボニルオキシ基で置換されていてもよい直鎖
若しくは分枝のＣ２〜Ｃ６アルキレン基を表し、Ｑは置
換されていてもよい、５員環または６員環の飽和若しく
は不飽和の残基を表す。）、ハロゲン原子、ニトロ基、
アミノ基、アシルアミノ基、Ｃ１〜Ｃ１２アルキルアミ
ノ基、ジＣ１〜Ｃ１２アルキルアミノ基、アシル基、ア
シロキシ基、置換されていてもよいアルケニル基、等が
挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, general formula (I)
May be substituted among the substituents on A and B in
Groups include a hydroxyl group and an optionally substituted C1
C12 alkyl group, C1-C12 alkoxy group, C1-
C12 alkoxy C1-C12 alkyl group, C1-C1
2 alkylcarbonyl groups, C1-C12 alkoxycar
Bonyl C1-C12 alkyl group, phenylalkyl group
Or C1-C12 alkoxy C1-C12 alkoxy
A carbonyl C1-C12 alkyl group, or -OR
1−Q (where R1Is a methylene group or C1-C12
Straight chain which may be substituted by alkylcarbonyloxy group
Or Q represents a branched C2-C6 alkylene group;
5-membered or 6-membered saturated or optionally substituted
Represents an unsaturated residue. ), Halogen atom, nitro group,
Amino group, acylamino group, C1-C12 alkylamino
Groups, di-C1-C12 alkylamino groups, acyl groups,
A siloxy group, an optionally substituted alkenyl group, etc.
No.
【００１０】また、上記のＱの５員環または６員環の飽
和残基としては、テトラヒドロフリル基、テトラヒドチ
エニル基、テトラヒドロピラニル基、ピペリジル基、ピ
ロリジル基、ピペラジル基、モルホニル基、ヘキサヒド
ロアゼピニル基、シクロヘキシル基等が挙げられ、Ｑの
５員環または６員環の不飽和残基としては。フリル基、
チエニル基、ピロリル基、ピリジル基、ピラニル基、チ
アゾリル基、オキサゾリル基、ピラゾリル基、ピラジル
基、イミダゾリル基、チアジアゾリル基、s-トリアジニ
ル基、ベンゾフラニル基、ベンゾチエニル基、インドリ
ル基、ベンズオキサゾリル基、ベンゾイミダゾリル基、
ベンゾチアゾリル基、シクロヘキセニレン基、等が挙げ
られる。The saturated residue of the 5- or 6-membered ring of Q includes a tetrahydrofuryl group, a tetrahydrothienyl group, a tetrahydropyranyl group, a piperidyl group, a pyrrolidyl group, a piperazyl group, a morphonyl group, Examples thereof include a hydroazepinyl group and a cyclohexyl group, and examples of the 5- or 6-membered unsaturated residue of Q include an unsaturated residue. Furyl group,
Thienyl, pyrrolyl, pyridyl, pyranyl, thiazolyl, oxazolyl, pyrazolyl, pyrazyl, imidazolyl, thiadiazolyl, s-triazinyl, benzofuranyl, benzothienyl, indolyl, benzoxazolyl , A benzimidazolyl group,
Examples include a benzothiazolyl group and a cyclohexenylene group.
【００１１】上記の一般式（Ｉ）におけるＡおよびＢ上
の置換基において、ハロゲン原子は、フッ素原子、塩素
原子、臭素原子および沃素原子を意味し、アシルアミノ
基としては、アセチルアミノ基等が挙げられ、アシロキ
シ基としては、下記一般式In the substituents on A and B in the general formula (I), the halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the acylamino group includes an acetylamino group and the like. And an acyloxy group represented by the following general formula
【００１２】[0012]
【化３】 Embedded image
【００１３】［式中、Ｔは、Ｃ１〜Ｃ４アルキル基、フ
ェニル基、フェノキシ基またはＣ１〜Ｃ４アルコキシ基
を表す。］で示される基、等が挙げられる。[Wherein T represents a C1-C4 alkyl group, a phenyl group, a phenoxy group or a C1-C4 alkoxy group. And the like, and the like.
【００１４】本発明で用いられる一般式（Ｉ）で示され
る二色性色素の具体例を次に示す。Specific examples of the dichroic dye represented by formula (I) used in the present invention are shown below.
【００１５】[0015]
【化４】 （Ｅ−１）Embedded image (E-1)
【００１６】[0016]
【化５】 （Ｅ−２）Embedded image (E-2)
【００１７】[0017]
【化６】 （Ｅ−３）Embedded image (E-3)
【００１８】[0018]
【化７】 （Ｅ−４）Embedded image (E-4)
【００１９】[0019]
【化８】 （Ｅ−５）Embedded image (E-5)
【００２０】尚、一般式（Ｉ）で示される化合物は、特
開平３−７２５７１号公報、特開平８−４８８９３号公
報、英国公開特許第２２９９８１１号明細書等に記載の
方法またはこれらに準ずる方法にて製造できる。The compound represented by the general formula (I) can be prepared by a method described in JP-A-3-72571, JP-A-8-48893, British Patent No. 2298911, or a method analogous thereto. It can be manufactured at
【００２１】本発明において、一般式（Ｉ）で示される
二色性色素を少なくとも１つ含む液晶組成物は、液晶性
物質を含有し液晶相を示す。In the present invention, the liquid crystal composition containing at least one dichroic dye represented by the general formula (I) contains a liquid crystal substance and exhibits a liquid crystal phase.
【００２２】液晶相の種類としてはネマチック相、コレ
ステリック相、スメクティック相、ディスコティック
相、等の公知の相を使用することができるが、ＧＨに使
用するためにはネマチック相、コレステリック相、スメ
クティック相が好ましく、ネマチック相が特に好まし
い。これらの相は含有する液晶性物質によってほぼ決ま
るが、少量の添加物により相が変化する場合も有る。こ
のような例としては少量の旋光性物質によってコレステ
リック相が現れる場合が挙げられる。また本発明の液晶
組成物の誘電率異方性は正でも負でもよく、目的の液晶
表示素子の形式に合わせて選択することができる。Known types of liquid crystal phases such as a nematic phase, a cholesteric phase, a smectic phase, and a discotic phase can be used. For use in GH, a nematic phase, a cholesteric phase, and a smectic phase are used. Are preferred, and a nematic phase is particularly preferred. These phases are substantially determined by the contained liquid crystalline substance, but the phases may be changed by a small amount of additives. An example of this is the case where a cholesteric phase appears due to a small amount of the optically active substance. The dielectric anisotropy of the liquid crystal composition of the present invention may be either positive or negative, and can be selected according to the type of the target liquid crystal display device.
【００２３】安定な液晶相を広い温度範囲で発現させる
ために、本発明の液晶組成物中の液晶性物質の含有量
は、通常、８０重量％以上が好ましく、９０重量％以上
がさらに好ましく、９５重量％以上が特に好ましい。ま
た、液晶性物質は単一の化合物でも複数の化合物の混合
物でも使用することができるが、安定な液晶相を広い温
度範囲で発現させるために一般に複数の化合物を混合し
て使用することが好ましい。具体的な液晶性物質として
は、液晶デバイスハンドブック；日本学術振興会第１４
２委員会編（１９８９年）第１５２〜１９２頁、同第７
１５〜７２２頁等に記載されたようなネマティック相あ
るいはスメクティック相を示すビフェニル系、フェニル
シクロヘキサン系、フェニルピリミジン系、シクロヘキ
シルシクロヘキサン系、等の各種の化合物または混合物
を使用することができる。また、好ましい化合物として
は、下記表１に例示されるものが使用できる。In order to develop a stable liquid crystal phase over a wide temperature range, the content of the liquid crystal substance in the liquid crystal composition of the present invention is usually preferably 80% by weight or more, more preferably 90% by weight or more. Particularly preferred is 95% by weight or more. In addition, the liquid crystal substance can be used as a single compound or a mixture of a plurality of compounds, but it is generally preferable to use a mixture of a plurality of compounds in order to develop a stable liquid crystal phase in a wide temperature range. . As a specific liquid crystalline substance, see Liquid Crystal Device Handbook;
2 Committee (1989), pp. 152-192, 7
Various compounds or mixtures such as biphenyl-based, phenylcyclohexane-based, phenylpyrimidine-based, and cyclohexylcyclohexane-based compounds that exhibit a nematic phase or a smectic phase as described on pages 15 to 722 and the like can be used. Further, as preferred compounds, those exemplified in Table 1 below can be used.
【００２４】[0024]
【化９】 Embedded image
【００２５】［式中、ＶおよびＷは、それぞれ、アルキ
ル基、アルコキシ基、アルコキシアルキル基、アルキル
フェニル基、アルコキシアルキルフェニル基、アルコキ
シフェニル基、アルキルシクロヘキシル基、アルコキシ
アルキルシクロヘキシル基、アルキルシクロヘキシルフ
ェニル基、シアノフェニル基、シアノ基、ハロゲン原
子、フルオロメチル基、フルオロメトキシ基、アルキル
フェニルアルキル基、アルコキシフェニルアルキル基、
アルキルシクロヘキシルアルキル基、アルコキシアルコ
キシヘキシルアルキル基、アルコキシフェニルアルキル
基、またはアルキルシクロヘキシルフェニルアルキル基
を表し、これらのアルキル鎖およびアルコキシ鎖中に光
学活性中心を有しても良い。またＶおよびＷ中のフェニ
ル基またはフェノキシ基は、シアノ基、フッ素原子、塩
素原子、等のハロゲン原子でさらに置換されてもよい。
また、上記各構造式中のフェニル基は、１個〜４個のフ
ッ素原子、塩素原子、等のハロゲン原子、シアノ基でさ
らに置換されてもよい。Ｕは水素原子、ハロゲン原子ま
たはシアノ基を表す。］[Wherein, V and W are an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkylphenyl group, an alkoxyalkylphenyl group, an alkoxyphenyl group, an alkylcyclohexyl group, an alkoxyalkylcyclohexyl group, an alkylcyclohexylphenyl group, respectively] , Cyanophenyl group, cyano group, halogen atom, fluoromethyl group, fluoromethoxy group, alkylphenylalkyl group, alkoxyphenylalkyl group,
Represents an alkylcyclohexylalkyl group, an alkoxyalkoxyhexylalkyl group, an alkoxyphenylalkyl group, or an alkylcyclohexylphenylalkyl group, and these alkyl chains and alkoxy chains may have an optically active center. Further, the phenyl group or phenoxy group in V and W may be further substituted with a halogen atom such as a cyano group, a fluorine atom and a chlorine atom.
Further, the phenyl group in each of the above structural formulas may be further substituted with one to four halogen atoms such as a fluorine atom and a chlorine atom, and a cyano group. U represents a hydrogen atom, a halogen atom or a cyano group. ]
【００２６】また、従来のシアノ基を含有した液晶化合
物の替わりに、−Ｆ，−ＣＦ3、−ＯＣＦ3、などのフッ
素原子またはフッ素原子含有基などの置換基を有するい
わいるフッ素系液晶性物質が薄膜トランジスタ方式液晶
ディスプレイ（ＴＦＴ・ＬＣＤ）に好ましいとされてお
り、これらのフッ素系液晶性物質も本発明の液晶組成物
に用いることができる。In addition, instead of the conventional liquid crystal compound containing a cyano group, a fluorine-based liquid crystal compound having a substituent such as a fluorine atom such as —F, —CF 3 , or —OCF 3 or a group containing a fluorine atom. The substance is considered to be preferable for a thin film transistor type liquid crystal display (TFT / LCD), and these fluorine-based liquid crystal substances can also be used in the liquid crystal composition of the present invention.
【００２７】本発明の液晶組成物に含まれる化合物の純
度は色素の種類や合成方法により若干異なるが、通常９
０〜１００％の範囲が使用でき、好ましくは９８〜１０
０％の範囲が、さらに好ましくは９９〜１００％の範囲
が、特に好ましく９９．５〜１００％の範囲が使用され
る。The purity of the compound contained in the liquid crystal composition of the present invention is slightly different depending on the kind of the dye and the synthesis method.
A range of 0 to 100% can be used, preferably 98 to 10%.
A range of 0%, more preferably a range of 99 to 100%, particularly preferably a range of 99.5 to 100% is used.
【００２８】本発明の液晶組成物の作製方法としては、
成分である二色性色素、液晶性物質等を混合することに
より得られる。混合の方法には公知の方法が用いられ
る。例えば、液晶性物質を加熱して等方性液体に融解さ
せ、これに一般式（Ｉ）で示される二色性色素を混合し
て溶解する方法等が挙げられる。The method for producing the liquid crystal composition of the present invention includes:
It can be obtained by mixing dichroic dyes, liquid crystal substances and the like as components. A known method is used for the mixing method. For example, there is a method in which a liquid crystalline substance is heated to be melted into an isotropic liquid, and a dichroic dye represented by the general formula (I) is mixed and dissolved therein.
【００２９】[0029]
【実施例】以下本発明の実施例を示すが、本発明はこれ
らによって限定されるものではない。 実施例 （二色比の測定）二色比（Ｒ）の測定は、一般式（Ｉ）
で示される二色性色素を含む液晶組成物を測定セルに注
入し、この測定セルの偏光吸収スペクトルを測定するこ
とにより行った。測定セルは２枚の石英製基板により作
成した。各石英製基板の片面にはポリイミド配向膜（日
立化成製、ＬＸ１４００）を約２０ｎｍ塗布し加熱を行
った後、一方向に布でラビング処理した。この石英製基
板を２枚配向膜面を内側にして貼り合わせた。この時、
周辺部にスペ−サを含む接着剤を塗布し、これを硬化さ
せることにより２枚の石英製基板の間隔が１７〜２４μ
ｍの液晶セルとした。この時、２枚の石英製基板のラビ
ング方向が互いに平行の関係となるように貼り合わせた
測定セルに本発明の液晶組成物を注入して測定を行っ
た。EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited by these. Example (Measurement of dichroic ratio) The dichroic ratio (R) is measured by the general formula (I)
Was carried out by injecting a liquid crystal composition containing a dichroic dye into a measurement cell, and measuring the polarization absorption spectrum of the measurement cell. The measurement cell was made of two quartz substrates. One side of each quartz substrate was coated with a polyimide alignment film (manufactured by Hitachi Chemical Co., LX1400) of about 20 nm, heated, and then rubbed in one direction with a cloth. Two quartz substrates were bonded together with the alignment film surface inside. At this time,
An adhesive containing a spacer is applied to the peripheral portion, and the adhesive is cured so that the distance between the two quartz substrates is 17 to 24 μm.
m liquid crystal cell. At this time, the measurement was performed by injecting the liquid crystal composition of the present invention into a measurement cell bonded so that the rubbing directions of the two quartz substrates were parallel to each other.
【００３０】ここで二色比とは特定の波長における、測
定セルのラビング方向に平行な偏光方向に平行な方向に
偏光した光に対する吸光度（Ａ1）と、測定セルのラビ
ング方向に垂直な方向の偏光した光に対する吸光度（Ａ
2）を測定し、以下の数１で示される数式により求めた
ものであり、測定セルのラビング方向に平行な方向に変
更した光に対する偏光吸収スペクトルのピーク波長での
値を用いた。吸光度の値としては、一般式（Ｉ）で示さ
れる二色性色素を含まない同様の液晶組成物を注入した
測定セルによる吸収を差し引いて、含まれる一般式
（Ｉ）で示される二色性色素そのものの吸収を用いた。Here, the dichroic ratio is the absorbance (A 1 ) at a specific wavelength with respect to light polarized in a direction parallel to the polarization direction parallel to the rubbing direction of the measurement cell, and a direction perpendicular to the rubbing direction of the measurement cell. Absorbance for polarized light (A
2 ) was measured, and the value was obtained by the mathematical formula shown in the following Expression 1, and the value at the peak wavelength of the polarized light absorption spectrum with respect to the light changed in the direction parallel to the rubbing direction of the measurement cell was used. The value of the absorbance is obtained by subtracting the absorption by a measurement cell into which a similar liquid crystal composition containing no dichroic dye represented by the general formula (I) is injected, and including the dichroism represented by the general formula (I) The absorption of the dye itself was used.
【００３１】[0031]
【数１】Ｒ＝Ａ1／Ａ2 ## EQU1 ## R = A 1 / A 2
【００３２】特に、液晶セルの偏光方向に垂直な方向の
偏光の吸収スペクトルのピ−ク波長での値を用いた。吸
光度の値としては、液晶セル基材による吸収を差し引い
て、液晶組成物そのものの吸収を用いた。液晶セルは２
枚の石英製基板により作製した。石英製基板にはポリイ
ミド配向膜（日立化成製、ＬＸ１４００）を約２０ｎｍ
塗布し加熱してイミド化を行った後、一方向にラビング
した。この石英製基板を２枚配向膜面を内側にして貼り
合わせた。この時、周辺部にスペ−サを含む接着剤を塗
布し、これを硬化させることにより２枚の石英製基板の
間隔が１７〜２４μmの液晶セルとした。この時、２枚
の石英製基板のラビング方向が互いに平行の関係となる
ように貼り合わせた。この測定セルに本発明の液晶組成
物を注入して測定を行った。その結果、表１に示すよう
にＥ−１〜Ｅ−５の化合物は、何れも二色性を有してい
た。In particular, the value at the peak wavelength of the absorption spectrum of the polarized light in the direction perpendicular to the polarization direction of the liquid crystal cell was used. As the value of the absorbance, the absorption of the liquid crystal composition itself was used by subtracting the absorption by the liquid crystal cell substrate. The liquid crystal cell is 2
It was manufactured using two quartz substrates. A quartz substrate is coated with a polyimide alignment film (LX1400, manufactured by Hitachi Chemical) at about 20 nm.
After applying and heating to perform imidization, rubbing was performed in one direction. Two quartz substrates were bonded together with the alignment film surface inside. At this time, an adhesive containing a spacer was applied to the peripheral portion and cured to form a liquid crystal cell in which the distance between the two quartz substrates was 17 to 24 μm. At this time, the two quartz substrates were bonded so that the rubbing directions were parallel to each other. The measurement was performed by injecting the liquid crystal composition of the present invention into this measurement cell. As a result, as shown in Table 1, all of the compounds E-1 to E-5 had dichroism.
【００３３】[0033]
【表１】 [Table 1]
【００３４】（吸光係数と吸収半値幅の測定）吸光係数
は下記数２で示される数式より求めた。ここでＭは二色
性色素の分子量、Ｒは二色性色素の二色比、Ａ2は前記
の意味を表わす。ｆは液晶組成物Ｅ7の比重、ｅは液晶
組成物Ｅ７中での二色性色素の濃度（％）、ｄはセル厚
（μｍ）を意味する。なお%は重量%を意味する。(Measurement of Absorption Coefficient and Absorption Half Width) The extinction coefficient was determined by the following equation (2). Here, M is the molecular weight of the dichroic dye, R is the dichroic ratio of the dichroic dye, and A 2 has the above-mentioned meaning. f denotes the specific gravity of the liquid crystal composition E7, e denotes the concentration (%) of the dichroic dye in the liquid crystal composition E7, and d denotes the cell thickness (μm). In addition,% means weight%.
【００３５】[0035]
【数２】吸光係数＝（Ｍ×（Ｒ＋１）2×Ａ２×1000）
／（４×ｆ×Ｒ2×ｅ×ｄ）## EQU2 ## Absorption coefficient = (M × (R + 1) 2 × A2 × 1000)
/ (4 × f × R 2 × e × d)
【００３６】吸収半値幅は、液晶セルの偏光方向に垂直
な方向の偏光の吸収スペクトルにのある特定の吸収ピ−
クについて、その吸収ピ−クの半分の高さを示す左右二
つ波長Ｗ1およびＷ2から下記数３で示される数式により
算出される。また、吸収スペクトル上における吸収半値
幅について図１に具体的に示す。The absorption half width is a specific absorption peak in the absorption spectrum of polarized light in a direction perpendicular to the polarization direction of the liquid crystal cell.
The peak is calculated from the two left and right wavelengths W 1 and W 2 indicating half the height of the absorption peak by the following equation (3). FIG. 1 specifically shows the half bandwidth at the absorption spectrum.
【００３７】[0037]
【数３】吸収半値幅＝｜Ｗ1−Ｗ2｜[Formula 3] Absorption half width = | W 1 −W 2 |
【００３８】本発明の一般式（Ｉ）に含まれるＥ−５で
示される化合物と、比較化合物Ｇ−１およびＧ−２に関
する測定結果を表２に示す。Table 2 shows the measurement results of the compound represented by E-5 in the general formula (I) of the present invention and the comparative compounds G-1 and G-2.
【００３９】[0039]
【化１０】 （Ｇ−１）Embedded image (G-1)
【００４０】[0040]
【化１１】 （Ｇ−２）Embedded image (G-2)
【００４１】[0041]
【表２】 [Table 2]
【００４２】表２から、本発明で用いられる二色性色素
は、大きな吸光係数と小さな吸収半値幅の２つの特性を
同時に有することがわかった。From Table 2, it was found that the dichroic dye used in the present invention had two characteristics of a large extinction coefficient and a small absorption half width at the same time.
【００４３】[0043]
【発明の効果】本発明の液晶組成物は、吸光係数が大き
くかつ吸収半値幅が小さいため、これを使用した液晶表
示素子は多彩で鮮明な色調を表示でき、工業的価値が大
きい。The liquid crystal composition of the present invention has a large extinction coefficient and a small absorption half width, so that a liquid crystal display device using the liquid crystal composition can display various and clear color tones and is of great industrial value.
【図１】図１はＥ−５と液晶組成物Ｅ７（メルク社製）
との混合物を注入した液晶セルの偏光吸収スペクトル、
図中において １：測定セルのラビング方向に平行な方向に偏光した光
に対する吸収スペクトル ２：測定セルのラビング方向に垂直な方向に偏光した光
に対する吸収スペクトル ３：Ｗ1 ４：Ｗ2 ５：吸収半値幅 ６：吸収ピーク を意味する。FIG. 1 shows E-5 and liquid crystal composition E7 (manufactured by Merck).
Polarization absorption spectrum of a liquid crystal cell into which a mixture of
In FIG 1: the absorption spectrum 2 for light polarized in a direction parallel to the rubbing direction of the measuring cell: absorption spectra 3 for light polarized in a direction perpendicular to the rubbing direction of the measuring cell: W 1 4: W 2 5: absorption Half width 6: means absorption peak.
Claims (1)
くは少なくとも１つの基で置換されていてもよい、ベン
ゼン、ナフタレン、ビフェニル、チオフェン、ベンゾチ
オフェン、チアゾール、ベンゾチアゾールまたはベンゾ
イソチアゾールを表し、ｎは０または１の整数を表
す。］で示される二色性色素を少なくとも１つ含むこと
を特徴とする液晶組成物。1. A compound represented by the following general formula (I): [Wherein, A and B each independently represent a benzene, naphthalene, biphenyl, thiophene, benzothiophene, thiazole, benzothiazole or benzoisothiazole which may be substituted with a hydrogen atom or at least one group, n represents an integer of 0 or 1. ] A liquid crystal composition comprising at least one dichroic dye represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14970698A JP4338059B2 (en) | 1998-05-29 | 1998-05-29 | Liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14970698A JP4338059B2 (en) | 1998-05-29 | 1998-05-29 | Liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11343487A true JPH11343487A (en) | 1999-12-14 |
| JP4338059B2 JP4338059B2 (en) | 2009-09-30 |
Family
ID=15481044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14970698A Expired - Lifetime JP4338059B2 (en) | 1998-05-29 | 1998-05-29 | Liquid crystal composition |
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| Country | Link |
|---|---|
| JP (1) | JP4338059B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007266411A (en) * | 2006-03-29 | 2007-10-11 | Nippon Kayaku Co Ltd | Field effect transistor |
| JP2013531106A (en) * | 2010-07-09 | 2013-08-01 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Semiconducting polymer |
| CN104781367B (en) * | 2012-11-07 | 2017-04-26 | 巴斯夫欧洲公司 | Polymers based on naphthodiones |
-
1998
- 1998-05-29 JP JP14970698A patent/JP4338059B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007266411A (en) * | 2006-03-29 | 2007-10-11 | Nippon Kayaku Co Ltd | Field effect transistor |
| JP2013531106A (en) * | 2010-07-09 | 2013-08-01 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Semiconducting polymer |
| US9287504B2 (en) | 2010-07-09 | 2016-03-15 | Merck Patent Gmbh | Semiconducting polymers |
| CN104781367B (en) * | 2012-11-07 | 2017-04-26 | 巴斯夫欧洲公司 | Polymers based on naphthodiones |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4338059B2 (en) | 2009-09-30 |
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