JPS6116789B2 - - Google Patents
Info
- Publication number
- JPS6116789B2 JPS6116789B2 JP13291083A JP13291083A JPS6116789B2 JP S6116789 B2 JPS6116789 B2 JP S6116789B2 JP 13291083 A JP13291083 A JP 13291083A JP 13291083 A JP13291083 A JP 13291083A JP S6116789 B2 JPS6116789 B2 JP S6116789B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- dichroic dye
- formula
- alkyl group
- crystal display
- 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
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000000975 dye Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- 101001082073 Homo sapiens Interferon-induced helicase C domain-containing protein 1 Proteins 0.000 description 1
- 102100027353 Interferon-induced helicase C domain-containing protein 1 Human genes 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Description
本発明は、カラー液晶表示素子用二色性色素に
係り、特にゲスト・ホスト型カラー液晶表示素子
（以下、Ｇ−HLCDと略称する。）に用いられる二
色性色素に関する。
従来、この種の二色性色素としては、アゾ・ア
ゾメチン・アントラキノン系のものが大半で、
様々な構造を有するものが発表されている。これ
等の二色性色素に要求される特性としては、二
色性比（以下、CRと称す。）が大であること、
分子吸光係数が大であること、長寿命であるこ
と、液晶に対する溶解性が大きいこと、などが
ある。
前記アゾ、アゾメチン系色素は、一般にCRは
大であるが、短寿命である。一方、アントラキノ
ン系については、長寿命であるがCRが比較的低
く、又、分子吸光係数もアゾ・アゾメチン系に較
べて小さい。このように、従来の二色性色素に
は、一長一短があり、Ｇ−HLCD用色素として十
分な特性を持つているとは云い難い。特に前記４
つの特性のうち、のCRが大であることが重要
で、CRが大きいほど表示コントラストの良いＧ
−HLCDが得られる。しかしながら、現在のとこ
ろCRが大と云われるアゾ・アゾメチン系色素で
もCR12が最大である。CR値は、高い程よく、
少なくともCR〓13が望まれる。
本発明は、このような点に鑑みなされたもの
で、二色性色素の中心にベリレン骨格、末端にア
ゾ色素を導入した色素を液晶組成物中に添加した
ことを特徴とするものである。この二色性色素
は、下記の一般構造式を有している。
一般式
ここで式中のＡ，Ｂは
Ｘ，Ｙは
The present invention relates to a dichroic dye for color liquid crystal display devices, and particularly to a dichroic dye used in a guest-host type color liquid crystal display device (hereinafter abbreviated as G-HLCD). Traditionally, most dichroic dyes of this type have been azo, azomethine, and anthraquinone.
Products with various structures have been announced. The characteristics required of these dichroic dyes include a high dichroic ratio (hereinafter referred to as CR);
It has a high molecular extinction coefficient, a long life, and high solubility in liquid crystals. The azo and azomethine dyes generally have a high CR, but have a short lifespan. On the other hand, anthraquinone series have a long life, but have a relatively low CR and also have a smaller molecular extinction coefficient than azo/azomethine series. As described above, conventional dichroic dyes have advantages and disadvantages, and it is difficult to say that they have sufficient characteristics as dyes for G-HLCD. Especially the above 4
Among the two characteristics, it is important that the CR is large; the larger the CR, the better the display contrast.
- HLCD is obtained. However, even among the azo/azomethine dyes, which are said to have the highest CR, CR12 is currently the highest. The higher the CR value, the better.
At least CR = 13 is desired. The present invention has been developed in view of these points, and is characterized in that a dichroic dye having a berylene skeleton at the center and an azo dye introduced at the end is added to a liquid crystal composition. This dichroic dye has the following general structural formula. general formula Here, A and B in the formula are X, Y are
【式】（R1，R2はアルキル基あるいは水素
で少なくとも一方がアルキル基）、アルキル基ま
たはアルコキシ基。
この分子構造において、特に重要なことは、ペ
リレン骨格にアゾキシ基[Formula] (R 1 and R 2 are an alkyl group or hydrogen and at least one is an alkyl group), an alkyl group or an alkoxy group. What is particularly important in this molecular structure is the azoxy group in the perylene skeleton.
【式】を導入し
たことである。
即ち、CR大とするには色素構造が剛直で細長
いことが望まれているが、本発明によると、剛直
性大であるが、やや細長さに劣る中心ペリレン骨
格と、剛直で細長い末端のアゾキシ基が相補うこ
とによつて、構造全体として極めて剛直でしかも
細長いという理想的な構造となる。このような構
造を有する二色性色素は、CRが高いばかりでな
く、他の二色性色素に要求される特性を十分満足
する。
なお、本発明の色素を添加して着色する液晶組
成物としては、ネマテイツク、コレステリツク、
スメクテイツク液晶などがある。
次に本発明の実施例について説明する。
ガラス基板上にインジウム−スズ酸化物からな
る透明導電膜を形成し、二酸化ケイ素で絶縁被覆
した後、更にその上に有機シラン系の水平配向剤
膜を薄くコートし、ラビングによりホモジニアス
配向処理を施こした液晶セルを作成する。
一方、誘電異方性が正のシアノビフエニル系液
晶組成物に、前記二色性色素を１％溶解して液晶
組成物を作り、この液晶組成物を前記液晶セルに
封入してＧ−HLCDとする。
この実施例によつて得られたＧ−HLCDならび
に従来の二色性色素を添加したＧ−HLCDの性能
比較を次の表に示す。なお表中のλ maxは、液
晶組成物中での色素の吸収極大波長を、溶解度は
液晶組成物中での値をそれぞれ示す。耐光寿命は
紫外線照射（通常光の約42倍の照射強度）によつ
て試験したもので、褪色は製造初期から80％変化
するまでの時間、電流値変化は製造初期の３倍に
なるまでの時間を各々示している。This is the introduction of [Formula]. That is, in order to achieve a large CR, it is desired that the dye structure be rigid and elongated, but according to the present invention, a central perylene skeleton that is highly rigid but slightly less slender, and a rigid and elongated terminal azoxy The complementary nature of the groups results in an ideal structure that is extremely rigid and elongated as a whole. A dichroic dye having such a structure not only has a high CR but also fully satisfies the characteristics required of other dichroic dyes. The liquid crystal compositions to be colored by adding the dye of the present invention include nematic, cholesteric,
There are smectic liquid crystals, etc. Next, examples of the present invention will be described. After forming a transparent conductive film made of indium-tin oxide on a glass substrate and insulatingly covering it with silicon dioxide, a thin organic silane-based horizontal alignment agent film is further coated on top of the film, and homogeneous alignment treatment is performed by rubbing. Create a strained liquid crystal cell. On the other hand, a liquid crystal composition is prepared by dissolving 1% of the dichroic dye in a cyanobiphenyl liquid crystal composition having positive dielectric anisotropy, and this liquid crystal composition is sealed in the liquid crystal cell to obtain a G-HLCD. . The following table shows a performance comparison between the G-HLCD obtained in this example and the G-HLCD added with a conventional dichroic dye. In the table, λ max indicates the absorption maximum wavelength of the dye in the liquid crystal composition, and solubility indicates the value in the liquid crystal composition. Light-resistance life was tested using ultraviolet irradiation (approximately 42 times the irradiation intensity of normal light), and fading was determined by the time it took for the color to change by 80% from the initial stage of manufacture, and the change in current value was determined by the time it took for the color to change by 80% from the initial stage of manufacture. Each shows the time.
【表】【table】
【表】
この表から明らからように、本発明に係る二色
性色素は溶解度が比較的高く寿命が長いうえ、し
かもCRが大きいなど優れた特性を兼備えてい
る。[Table] As is clear from this table, the dichroic dye according to the present invention has excellent properties such as relatively high solubility, long life, and high CR.
Claims (1)
の一般構造式を有する化合物であることを特徴と
するカラー液晶表示素子用二色性色素。 一般構造式 但し式中Ａ，Ｂは Ｘ，Ｙは【式】（R1，R2はアルキル基あ るいは水素で少なくとも一方がアルキル基）、ア
ルキル基またはアルコキシ基。 ２ 特許請求の範囲第１項記載において、前記化
合物が下記の分子構造式を有するものであること
を特徴とするカラー液晶表示素子用二色性色素。 ３ 特許請求の範囲第１項記載において、前記化
合物が下記の分子構造式を有するものであること
を特徴とするカラー液晶表示素子用二色性色素。 [Scope of Claims] 1. A dichroic dye for a color liquid crystal display element, characterized in that the dichroic dye added to a liquid crystal composition is a compound having the following general structural formula. General structural formula However, A and B in the formula X and Y are [Formula] (R 1 and R 2 are an alkyl group or hydrogen and at least one is an alkyl group), an alkyl group or an alkoxy group. 2. A dichroic dye for a color liquid crystal display device according to claim 1, wherein the compound has the following molecular structure formula. 3. A dichroic dye for a color liquid crystal display device according to claim 1, wherein the compound has the following molecular structure formula.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13291083A JPS6026084A (en) | 1983-07-22 | 1983-07-22 | Dichromatic coloring matter for color liquid crystal display element |
| US06/616,722 US4607097A (en) | 1983-06-03 | 1984-06-04 | Dichromatic coloring matter for a colored liquid crystal display element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13291083A JPS6026084A (en) | 1983-07-22 | 1983-07-22 | Dichromatic coloring matter for color liquid crystal display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6026084A JPS6026084A (en) | 1985-02-08 |
| JPS6116789B2 true JPS6116789B2 (en) | 1986-05-02 |
Family
ID=15092382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13291083A Granted JPS6026084A (en) | 1983-06-03 | 1983-07-22 | Dichromatic coloring matter for color liquid crystal display element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6026084A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4597891A (en) * | 1984-06-04 | 1986-07-01 | Polaroid Corporation | Liquid crystal compositions and devices and novel compounds |
-
1983
- 1983-07-22 JP JP13291083A patent/JPS6026084A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6026084A (en) | 1985-02-08 |
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