JPS61143370A - Squarylium compound - Google Patents
Squarylium compoundInfo
- Publication number
- JPS61143370A JPS61143370A JP26419284A JP26419284A JPS61143370A JP S61143370 A JPS61143370 A JP S61143370A JP 26419284 A JP26419284 A JP 26419284A JP 26419284 A JP26419284 A JP 26419284A JP S61143370 A JPS61143370 A JP S61143370A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- compound shown
- compound
- squarylium 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.)
- Pending
Links
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- Pyrane Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なスクアリリウム化合物に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel squarylium compound.
近年、拡大投射レーザー書き込み液晶ディスプレイ（以
下、液晶ディスプレイと記す）Ｋよる表示が提案されて
いる（日むエレクトロニクス、／９ｔ０年？月グ日号、
ｐ、 ＋θ−６４ｔ）。In recent years, a display using an enlarged projection laser-written liquid crystal display (hereinafter referred to as liquid crystal display) has been proposed (Japan Electronics, /9t0?Monday issue,
p, +θ-64t).
この液晶ディスプレイは、二枚のガラス基板の間に液晶
を注入し、かつガラス基板と液晶との間にレーザー光吸
収層を挿入した液晶セルに、レーザー光を照射して該吸
収層に熱を吸収させ、そしてその吸収熱による液晶の相
転移を起こさせることにより、液晶セルへの書き込みを
行ない、この液晶セルに別の光を蟲てて投射拡大表示す
るものである。This liquid crystal display consists of a liquid crystal cell in which liquid crystal is injected between two glass substrates and a laser light absorption layer is inserted between the glass substrate and the liquid crystal. Laser light is irradiated to heat the absorption layer. By absorbing the heat and causing a phase transition in the liquid crystal due to the absorbed heat, writing is performed on the liquid crystal cell, and another light is projected onto the liquid crystal cell to perform enlarged display.
また、このような液晶ナイスプレイにおいて、液晶セル
に用いる液晶に対して、さらにレーザー光発振波長付近
に吸収を有する化合物を加えた液晶組成物を使用し、こ
れにレーザー光を照射すると該化合物が直接レーザー光
を吸収する４ｔ／り）。In addition, in such a liquid crystal nice play, a liquid crystal composition is used in which a compound having absorption near the laser beam oscillation wavelength is added to the liquid crystal used in the liquid crystal cell, and when the compound is irradiated with laser light, the compound is removed. (4t/litre) that directly absorbs laser light.
一方、下記構造式〔Ａ〕で表わされるスクアリリウム化
合物は、ごθθ〜／１）００ｎのレーザー光発振波長付
近に吸収を有し、上記液晶ディ／（フレイとけ違って、
液晶を使用しない電子感光材料、光デイスク用記録材料
あるｂは赤外線カットフィルターに有用性が期待されて
いる（特開昭！Ｊ”−，２／７ｊｔｊＦ号公報）。On the other hand, the squarylium compound represented by the following structural formula [A] has absorption near the laser light oscillation wavelength of θθ~/1)00n, and unlike the liquid crystal di/(Fray),
Electrophotosensitive materials that do not use liquid crystals and recording materials for optical discs are expected to be useful as infrared cut filters (Japanese Patent Application Laid-Open No. 2003-120000-2/7jtjF).
上記〔Ａ〕のスクアリリウム化合物を、前記液晶ディス
プレイに用因るためには、該化合物が液晶との溶解性が
劣るという問題があった。In order to use the above squarylium compound [A] in the liquid crystal display, there is a problem that the compound has poor solubility with the liquid crystal.
本発明は、レーザー光発振波長付近に吸収を有し、かつ
液晶に対して良好な溶解性を有するスクアリリウム化合
物の提供を目的とする。An object of the present invention is to provide a squarylium compound that has absorption near the laser beam oscillation wavelength and has good solubility in liquid crystals.
本発明は、下記一般式〔Ｉ〕
（式中、Ｒはアルキル基、アルコキシ基、またはハロゲ
ン原子を示す）で表わされるスクアリリウム化合物を要
旨とする。The gist of the present invention is a squarylium compound represented by the following general formula [I] (wherein R represents an alkyl group, an alkoxy group, or a halogen atom).
前記一般式［Ｉ）で表わされる本発明のスクアリリウム
化合物にお込て、Ｒは、メチル基、エチル基、プロピル
基、ブチル基、ペンチル基、ヘキシル基、ヘゲチル基、
オクチル基等のアルキル基；メトキシ基、エトキシ基、
グロボキシ基、ブトキシ基、ぺ／トキシ基、オクトキシ
基等のアルコキシ基：７ツ累原子、塩素原子、臭素原子
等のハロゲン原子を示す。In the squarylium compound of the present invention represented by the general formula [I], R is a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a hegetyl group,
Alkyl groups such as octyl groups; methoxy groups, ethoxy groups,
Alkoxy groups such as globoxy group, butoxy group, pe/toxy group, octoxy group: Indicates a halogen atom such as a heptad atom, a chlorine atom, a bromine atom, etc.
前記一般式ＣＩ］で表わされる仕置９１Ｊけ、例えは下
記構造式〔■〕
（式中、Ｒは前記一般式［１）Ｋおけると同一の意義を
Ｍする。）で表わされる化合物と、３，４ｔ−ジヒドロ
キシ−３−シクロブテン−／、２−ジオンとを＃媒中で
反応させることによって製造することができる。The structure 91J represented by the above general formula [CI] is, for example, the following structural formula [■] (wherein, R has the same meaning as in the above general formula [1) K]. ) and 3,4t-dihydroxy-3-cyclobutene-/,2-dione in a medium.
前記一般式〔■〕で示される本発明のスクアリリウム化
合物は、レーザー光発振波長付近に吸収を有しており、
かつ、液晶に対する溶解性もと
良好であるので、液晶＃混合し、液晶組成物として、前
記ｉ晶ディスプレイに用いることかできる。The squarylium compound of the present invention represented by the general formula [■] has absorption near the laser beam oscillation wavelength,
In addition, since it has good solubility in liquid crystals, it can be mixed with liquid crystals and used as a liquid crystal composition in the i-crystal display.
そして、さらに、この本発明のスクアリリウム化合物は
、電子感光材料、光デイスク用記録材料あるいは赤外線
カットフィルターとしても用いることができる。Furthermore, the squarylium compound of the present invention can also be used as an electrophotosensitive material, a recording material for an optical disk, or an infrared cut filter.
次に本発明を実施例によって、さらに具体的に説明する
。Next, the present invention will be explained in more detail with reference to Examples.
実施例／ ３、タージヒド四キシー３−シクロブテン−／。 Example/ 3. Terdihyde tetraxy 3-cyclobutene-/.
コーシオンＯ１λ３２にｎ−ブチルアルコール／！−を
加え、約１００’Ｃに加熱して溶解した。Cosion O1λ32 with n-butyl alcohol/! - was added and heated to about 100'C to dissolve.
この溶液にキノリン／殺、ヨウ化−ノーメチル−４ｔ、
ｔ−シーｐ−ｎ−ペンチルフェニルビリリウム２８．２
６９およびベンゼン／ ０ 、ｐを奈加し１．９！〜１
０！℃で約３時間撹拌した。ただし、撹拌中にベンゼン
１０ｄ１ブチルアルコール乙−を分割添加しながら生ず
る水を共沸的に留去した。冷却後、ｎ−へキサンを加え
結晶を析出させた。得られた結晶をカラムクロマトグラ
フィーによシ精製して下記構造式
で示されるスクアリリウム化合物（下記第７表のＡ７の
化合物）を得た。本化合物はコｇ ｔｒ、。To this solution, quinoline/killed, iodide-nomethyl-4t,
t-Cp-n-pentylphenylvirylium 28.2
69 and benzene/0, p is 1.9! ~1
0! The mixture was stirred at ℃ for about 3 hours. However, while stirring, 10 d of benzene and 1 butyl alcohol were added in portions, and the resulting water was azeotropically distilled off. After cooling, n-hexane was added to precipitate crystals. The obtained crystals were purified by column chromatography to obtain a squarylium compound represented by the following structural formula (compound A7 in Table 7 below). This compound is cogtr.
〜２’４９．０℃の融点を示し、クロロホルム溶液中で
の可視部吸収スペクトルの極大吸収波長は／ ！ Ｏｎ
ｍ及びりθθｎｍであった。It shows a melting point of ~2'49.0℃, and the maximum absorption wavelength of the visible absorption spectrum in a chloroform solution is /! On
m and θθnm.
上述の如くして得られたスクアリリウム化合物を、シア
ノオクチルビフェニル（スメクチック相を有するビフェ
ニル系液晶〕にｏ、ｒ重量ノく一セントの割合で添加し
、１０℃以上に加熱撹拌して等方性液体となった状態で
溶解させ、液晶組成物を製造した。この状態で得られた
液晶組成物の吸収スペクトルを測定した所、／６−ｎｍ
及びり／コｎｍ Ｉｃ極大ピークを示し、ｒｊＯｎｍを
発振波長とするＧａＡＩＡθ半導体レーザーの発振波長
に近い値を示した。The squarylium compound obtained as described above was added to cyanooctylbiphenyl (biphenyl liquid crystal having a smectic phase) at a ratio of 1/1 cent by weight, and heated to 10°C or higher and stirred to make it isotropic. A liquid crystal composition was produced by dissolving it in a liquid state.When the absorption spectrum of the liquid crystal composition obtained in this state was measured, it was /6-nm.
It showed a maximum peak of Ic and a value close to the oscillation wavelength of a GaAIA theta semiconductor laser whose oscillation wavelength is rjOnm.
このようＫして調整した上記液晶組成物を、透ＢＡ電極
を有し液晶組成物と接する面を垂直配向処理剤（オクタ
デシルジメチルＣ３−（トリメトキシシリル） ７”
ｏ ヒル〕アンモニウムクロライド）で垂直配向処理を
施した上下２収のガラス基板からなる素子（基板間ギャ
ップ：りμｍ）に封入した。この素子に／ ｊ Ｏｎｍ
に発振波長を有するＧａＡＩＡａ半導体レーザーを照射
し、７０μｍのスポットで記録した。このスポット部分
は温度が上昇し、規則正しく垂直配向していた液晶組成
物が等方性液体状態に変化した。The liquid crystal composition thus prepared was treated with a vertical alignment treatment agent (octadecyldimethyl C3-(trimethoxysilyl) 7") on the surface having the transparent BA electrode and in contact with the liquid crystal composition.
It was sealed in an element (gap between substrates: 1 μm) consisting of two glass substrates, upper and lower, which had been subjected to vertical alignment treatment using ammonium chloride (Hill). To this element / j Onm
A GaAIAa semiconductor laser having an oscillation wavelength was irradiated with a 70 μm spot and recorded. The temperature of this spot increased, and the liquid crystal composition, which had been regularly and vertically aligned, changed to an isotropic liquid state.
レーザー光の照射を中止し、冷却後、この素子にハロゲ
ンラング光を透適させてスクリーン上に／１）１７倍に
拡大した投影図を映写するとレーザー光で記録して、液
晶分子の配列が乱れた部分はスクリーン上に黒く投影さ
れ、コントラストの良好な表示が得られた。After the laser light irradiation is stopped and the device is cooled, a halogen Lang light is transmitted through the device and a projection image magnified 17 times is projected on the screen.The laser light records the projection image and the alignment of the liquid crystal molecules is recorded. The disturbed areas were projected black on the screen, resulting in a display with good contrast.
実施例λ
実施例／において使用したヨウ化−コーメチルー＜ｔ、
ｔ−シーｐ−ｎ−ペンチルフェニルビリリウムのかわり
に、ヨウ化−２−メチルータ、６−ジーブチルフェニル
ピリリウム八り！２を使用すること以外は実施例／の方
法に従って、下記構造式
で示されるスクアリリウム化合物（下記第１表の＆乙の
化合物）を得た。本化合物はおｔｒ、。Example λ Iodide-comethyl-<t, used in Example/
Instead of t-p-n-pentylphenylpyrylium, 2-methyl-iodide and 6-dibutylphenylpyrylium are used! A squarylium compound represented by the following structural formula (compounds &B in Table 1 below) was obtained according to the method in Example 2 except for using No. 2. This compound is tr.
〜−グ３．θ℃の融点を示し、クロロホルム溶液中での
可視部吸収スペクトルの極大吸収波長はＦ 、ｔ Ｏｎ
ｍ及びりθＯｎ＋ｎであった。~-g3. It shows the melting point of θ℃, and the maximum absorption wavelength of the visible absorption spectrum in chloroform solution is F, t On
m and θOn+n.
この化合物をシアノオクチルビフェニルとシアノノニル
ビフェニルの／対／の混合物ＫＯ，ｊ重景パーセント添
加し、１０℃以上に加熱して等方性液体となった状態で
良くかき混ぜて溶解させ、液晶組成物を製造した。この
状態で得られた液晶組成物の吸収スペクトルはｆ ｄ
２ ｎｍ及び９ ／ 、２ ｎｍ ＶＣ極大ピークを示
した。This compound is added to a mixture of cyanooctylbiphenyl and cyanononylbiphenyl in an amount of KO,j weight percent, heated to 10° C. or higher to become an isotropic liquid, stir well to dissolve, and form a liquid crystal composition. was manufactured. The absorption spectrum of the liquid crystal composition obtained in this state is f d
It showed a VC maximum peak of 2 nm and 9/2 nm.
得られた液晶組成物を使用し、実施例／の方法に従って
表示を行うと、コントラストの良好な結果が得られた。When the obtained liquid crystal composition was used for display according to the method of Example, results with good contrast were obtained.
実施例３
実施例／及び実施例２の方法に従って合成した本発明の
スクアリリウム化合物の例を第１表にクロロホルム溶液
中での極太吸収波長とともに示す。Example 3 Examples of the squarylium compounds of the present invention synthesized according to the methods of Examples/Example 2 are shown in Table 1 along with the thickest absorption wavelengths in chloroform solutions.
Claims (1)
ン原子を示す）で表わされるスクアリリウム化合物。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼……[I] (In the formula, R represents an alkyl group, an alkoxy group, or a halogen atom) Squarylium compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26419284A JPS61143370A (en) | 1984-12-14 | 1984-12-14 | Squarylium compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26419284A JPS61143370A (en) | 1984-12-14 | 1984-12-14 | Squarylium compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61143370A true JPS61143370A (en) | 1986-07-01 |
Family
ID=17399753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26419284A Pending JPS61143370A (en) | 1984-12-14 | 1984-12-14 | Squarylium compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61143370A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5275917A (en) * | 1991-07-09 | 1994-01-04 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US5470683A (en) * | 1993-07-28 | 1995-11-28 | Brother Kogyo Kabushiki Kaisha | Photosensitive microcapsule toner |
| US6171759B1 (en) | 1992-05-14 | 2001-01-09 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
-
1984
- 1984-12-14 JP JP26419284A patent/JPS61143370A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5275917A (en) * | 1991-07-09 | 1994-01-04 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US6171759B1 (en) | 1992-05-14 | 2001-01-09 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US5470683A (en) * | 1993-07-28 | 1995-11-28 | Brother Kogyo Kabushiki Kaisha | Photosensitive microcapsule toner |
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