JPH07196620A - Method for producing 8-oxyquinoline-aluminum salt - Google Patents
Method for producing 8-oxyquinoline-aluminum saltInfo
- Publication number
- JPH07196620A JPH07196620A JP1222294A JP1222294A JPH07196620A JP H07196620 A JPH07196620 A JP H07196620A JP 1222294 A JP1222294 A JP 1222294A JP 1222294 A JP1222294 A JP 1222294A JP H07196620 A JPH07196620 A JP H07196620A
- Authority
- JP
- Japan
- Prior art keywords
- oxyquinoline
- aluminum
- aluminum salt
- producing
- reaction
- 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.)
- Withdrawn
Links
Landscapes
- Luminescent Compositions (AREA)
Abstract
(57)【要約】
【目的】 中和等の操作が不要であって、しかも濾過等
の操作が容易である８−オキシキノリン−アルミニウム
塩の製造方法を提供すること。
【構成】 ８−ヒドロキシキノリンとアルミニウムアル
コラ−トとを、有機溶媒中で反応させることを特徴とす
る８−オキシキノリン−アルミニウム塩の製造方法。
【効果】 本発明の製造方法によれば、中和等の操作が
不要であって、反応による発熱も少なく、しかも濾過等
の操作が容易であるので、８−オキシキノリン−アルミ
ニウム塩を効率的に製造することができる。(57) [Summary] [Object] To provide a method for producing an 8-oxyquinoline-aluminum salt, which does not require operations such as neutralization and is easy to perform operations such as filtration. A method for producing an 8-oxyquinoline-aluminum salt, which comprises reacting 8-hydroxyquinoline with aluminum alcoholate in an organic solvent. [Effects] According to the production method of the present invention, operations such as neutralization are unnecessary, less heat is generated by the reaction, and operations such as filtration are easy, so that 8-oxyquinoline-aluminum salt can be efficiently used. Can be manufactured.
Description
【０００１】[0001]
【産業上の利用分野】本発明は電界発光素子用材料等と
して有用な８−オキシキノリン−アルミニウム塩の製造
方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an 8-oxyquinoline-aluminum salt which is useful as a material for electroluminescent devices.
【０００２】[0002]
【従来の技術】８−オキシキノリン−アルミニウム塩
は、トリス（８−キノリノ−ル）アルミニウム錯体とも
称され、Ａｌ（Ｃ9 Ｈ6 ＯＮ）3 なる組成式を有する化
合物であり、電界発光素子用材料等として注目されてい
る化合物である（特開平４−２０６２９６号公報、特開
平３−２５５１９０号公報等）。８−オキシキノリンの
金属錯体は、８−オキシキノリン又はそのアルカリ金属
塩と銅、亜鉛、アルミニウム等の金属の塩とを反応させ
ることにより得る方法が通常である（特開昭４９−４３
９８３号公報等）。しかし、このような方法で、８−オ
キシキノリン−アルミニウム塩を得ようとすると、溶媒
として水溶媒を使用し、反応後、アルカリで中和し、析
出した結晶を濾過する必要があるが、ここで析出した結
晶は極めて微細であって、濾過の作業性が悪いという問
題がある。2. Description of the Related Art 8-Oxyquinoline-aluminum salt, also called tris (8-quinolinol) aluminum complex, is a compound having a composition formula of Al (C 9 H 6 ON) 3 and is used for electroluminescence devices. It is a compound attracting attention as a material and the like (JP-A-4-206296, JP-A-3-255190, etc.). The metal complex of 8-oxyquinoline is usually obtained by reacting 8-oxyquinoline or an alkali metal salt thereof with a salt of a metal such as copper, zinc or aluminum (JP-A-49-43).
983, etc.). However, in order to obtain an 8-oxyquinoline-aluminum salt by such a method, it is necessary to use an aqueous solvent as a solvent, neutralize with an alkali after the reaction, and filter the precipitated crystals. The crystals precipitated in 1. are extremely fine, and there is a problem that the workability of filtration is poor.
【０００３】[0003]
【発明が解決しようとする課題】本発明は中和等の操作
が不要であって、しかも濾過等の操作が容易である８−
オキシキノリン−アルミニウム塩の製造方法を提供する
ことを目的とする。The present invention does not require operations such as neutralization and is easy to perform operations such as filtration.8-
An object is to provide a method for producing an oxyquinoline-aluminum salt.
【０００４】[0004]
【課題を解決するための手段】本発明は、８−ヒドロキ
シキノリンとアルミニウムアルコラ−トとを、有機溶媒
中で反応させることを特徴とする８−オキシキノリン−
アルミニウム塩の製造方法である。The present invention is characterized by reacting 8-hydroxyquinoline with aluminum alcoholate in an organic solvent.
It is a method for producing an aluminum salt.
【０００５】アルミウムアルコラ−トとしては、アルミ
ニウムトリメトキシド、アルミニウムトリエトキシド、
アルミニウムトリプロポキシド、アルミニウムトリブト
キシド等が挙げられるが、炭素数が４以下のアルコキシ
ドが好ましい。有機溶媒としては、アルミニウムアルコ
ラ−トと８−ヒドロキシキノリンを溶解しうるものであ
ればよいが、水を含む溶媒は好ましくない。このような
ものとして、ベンゼン、トルエン等の芳香族炭化水素系
溶媒、メタノ−ル、エタノ−ル等のアルコ−ル系溶媒、
アセトン、メチルエチルケトン等のケトン系溶媒やエ−
テル系、エステル系等の各種溶媒が挙げられる。好まし
くは、反応温度で液体で、沸点が１２０℃以下の有機溶
媒である。有機溶媒の使用量は、アルミニウムアルコラ
−トと８−ヒドロキシキノリンを溶解するに足る量であ
れば十分である。Aluminum alloys include aluminum trimethoxide, aluminum triethoxide,
Examples thereof include aluminum tripropoxide and aluminum tributoxide, and alkoxides having 4 or less carbon atoms are preferable. Any organic solvent may be used as long as it can dissolve aluminum alcoholate and 8-hydroxyquinoline, but a solvent containing water is not preferred. As such, aromatic hydrocarbon solvents such as benzene and toluene, alcohol solvents such as methanol and ethanol,
Ketone solvents such as acetone and methyl ethyl ketone, and
There are various solvents such as tellurium-based and ester-based solvents. An organic solvent which is liquid at the reaction temperature and has a boiling point of 120 ° C. or lower is preferable. The amount of the organic solvent used is sufficient as long as it dissolves the aluminum alcoholate and 8-hydroxyquinoline.
【０００６】反応方法は任意であるが、結晶が比較的大
きい８−オキシキノリン−アルミニウム塩を得るために
は、アルミニウムアルコラ−トの有機溶媒溶液に、８−
ヒドロキシキノリンの有機溶媒溶液を滴下するか、逆に
８−ヒドロキシキノリンの有機溶媒溶液に、アルミニウ
ムアルコラ−トの有機溶媒溶液を滴下することが好まし
い。この際の反応温度は室温以上、好ましくは４０℃以
上とすることが好ましいが、高温にすると反応器等の腐
食が生じるので、１００℃以下とすることがよい。８−
ヒドロキシキノリンとアルミニウムアルコラ−トの割合
は、理論量である３：１（モル比）又はその前後とする
ことがよい。８−ヒドロキシキノリンとアルミニウムア
ルコラ−トの反応は、温度、濃度、滴下速度等により変
化するが、急激に反応が生じると微細な結晶が析出しや
すいので、滴下開始後、５〜３０分後に８−オキシキノ
リン−アルミニウム塩の結晶が析出するように上記条件
を調整することがよい。The reaction method is arbitrary, but in order to obtain an 8-oxyquinoline-aluminum salt having relatively large crystals, a solution of aluminum alcoholate in an organic solvent 8
It is preferable to drop the organic solvent solution of hydroxyquinoline or, conversely, the organic solvent solution of aluminum alcoholate to the organic solvent solution of 8-hydroxyquinoline. The reaction temperature at this time is preferably room temperature or higher, preferably 40 ° C. or higher, but if the temperature is raised to high temperature, corrosion of the reactor or the like occurs, so 100 ° C. or lower is preferable. 8-
The ratio of hydroxyquinoline and aluminum alcoholate is preferably the theoretical amount of 3: 1 (molar ratio) or around that. The reaction of 8-hydroxyquinoline and aluminum alcoholate varies depending on the temperature, the concentration, the dropping rate, etc., but if the reaction suddenly occurs, fine crystals tend to precipitate, so 5 to 30 minutes after the start of dropping, It is preferable to adjust the above conditions so that crystals of 8-oxyquinoline-aluminum salt are precipitated.
【０００７】反応開始後、攪拌を行い、しばらくすると
黄色の結晶が急激に析出し、通常、約１時間以内で反応
が終了する。反応終了後、反応混合物を冷却して、８−
オキシキノリン−アルミニウム塩の結晶を殆ど析出さ
せ、これを分離することが有利である。析出量は有機溶
媒の種類、量等により異なるが９５％以上が析出するよ
うに冷却することが望ましい。好ましくは、３０℃以
下、より好ましくは１０℃以下に冷却する。After the reaction is started, stirring is carried out, and after a while, yellow crystals are rapidly precipitated, and the reaction is usually completed within about 1 hour. After completion of the reaction, the reaction mixture is cooled to 8-
It is advantageous to precipitate most of the oxyquinoline-aluminum salt crystals and separate them. The amount of precipitation varies depending on the kind and amount of the organic solvent, but it is desirable to cool so that 95% or more is precipitated. It is preferably cooled to 30 ° C or lower, more preferably 10 ° C or lower.
【０００８】これを濾過、遠心分離等により分離する。
この際、溶媒で洗浄すれば純度が上がる。洗浄溶媒とし
て反応で使用した有機溶媒を使用すれば溶媒の回収を効
率的に行うことができる。また、純度が不十分のとき
は、再結晶等により精製する。これを乾燥して８−オキ
シキノリン−アルミニウム塩を得る。This is separated by filtration, centrifugation or the like.
At this time, the purity is increased by washing with a solvent. If the organic solvent used in the reaction is used as the washing solvent, the solvent can be efficiently recovered. If the purity is insufficient, the product is purified by recrystallization or the like. This is dried to obtain an 8-oxyquinoline-aluminum salt.
【０００９】[0009]
実施例１ アルミニウムトリイソプロポキシド２０．４ｇをベンゼ
ン３００ｍｌに添加し、７０℃に加温して溶解させたの
ち、８−ヒドロキシキノリン４３．６ｇのベンゼン溶液
を１０分間で滴下した。７０℃で攪拌を続けたところ、
滴下終了後約１５分で黄色結晶が急激に析出し、更に１
５分間反応を続けた。反応終了後、１５℃に冷却し、更
に結晶を析出させ、濾過し、ベンゼンによる洗浄を２回
行った。液相は４００．２ｇであり、ベンゼン９３．３
重量％、イソプロパノ−ル５．８重量％を含んでいた。
濾過、洗浄で得られた固体は乾燥したのち、元素分析し
た。結果は次のとおり。 淡黄緑色固体（粉体） ４３．３ｇ、モル収率 ９４．
２％ 元素分析（％） Ｃ：７０．２，Ｈ：４．２，Ｎ：８．
８，Ａｌ：６．５，Ｆｅ：１０ｐｐｍExample 1 20.4 g of aluminum triisopropoxide was added to 300 ml of benzene and heated to 70 ° C. to dissolve it, and then a solution of 43.6 g of 8-hydroxyquinoline in benzene was added dropwise over 10 minutes. When stirring was continued at 70 ° C,
Approximately 15 minutes after the completion of dropping, yellow crystals were rapidly precipitated,
The reaction was continued for 5 minutes. After completion of the reaction, the mixture was cooled to 15 ° C., crystals were further precipitated, filtered, and washed with benzene twice. The liquid phase was 400.2 g, and benzene 93.3
% By weight and 5.8% by weight of isopropanol.
The solid obtained by filtration and washing was dried and then subjected to elemental analysis. The results are as follows. Light yellow-green solid (powder) 43.3 g, molar yield 94.
2% Elemental analysis (%) C: 70.2, H: 4.2, N: 8.
8, Al: 6.5, Fe: 10 ppm
【００１０】実施例２ アルミニウムトリイソプロポキシド１０．２ｇをイソプ
ロパノ−ル３００ｍｌに添加し、６０℃に加温して溶解
させたのち室温まで攪拌放冷した。一部アルミニウムト
リイソプロポキシドが微細結晶として析出するが、この
懸濁液に８−ヒドロキシキノリン２１．８ｇを加えて室
温下に攪拌を継続すると、時間経過と共に黄色固体が析
出してきた。２時間後に反応物を濾過し、イソプロパノ
−ルによる洗浄を２回行ったのち、乾燥して黄色固体
（粉末）２１．０ｇを得た。Example 2 10.2 g of aluminum triisopropoxide was added to 300 ml of isopropanol, heated to 60 ° C. to dissolve it, and then cooled to room temperature with stirring. A part of aluminum triisopropoxide was precipitated as fine crystals, and when 21.8 g of 8-hydroxyquinoline was added to this suspension and stirring was continued at room temperature, a yellow solid began to precipitate with the passage of time. After 2 hours, the reaction product was filtered, washed with isopropanol twice, and then dried to obtain 21.0 g of a yellow solid (powder).
【００１１】[0011]
【発明の効果】本発明の製造方法によれば、中和等の操
作が不要であって、反応による発熱も少なく、しかも濾
過等の操作が容易であるので、８−オキシキノリン−ア
ルミニウム塩を効率的に製造することができる。EFFECTS OF THE INVENTION According to the production method of the present invention, operations such as neutralization are not required, heat generated by the reaction is small, and operations such as filtration are easy. It can be manufactured efficiently.
Claims (2)
アルコラ−トとを、有機溶媒中で反応させることを特徴
とする８−オキシキノリン−アルミニウム塩の製造方
法。1. A method for producing an 8-oxyquinoline-aluminum salt, which comprises reacting 8-hydroxyquinoline with aluminum alcoholate in an organic solvent.
アルコラ−トとを、有機溶媒中、４０℃以上に加温して
反応させたのち、３０℃以下に冷却して８−オキシキノ
リン−アルミニウム塩の結晶を析出させることを特徴と
する８−オキシキノリン−アルミニウム塩の製造方法。2. 8-Hydroxyquinoline and aluminum alcoholate are reacted in an organic solvent by heating to 40 ° C. or higher and then cooled to 30 ° C. or lower to obtain 8-oxyquinoline-aluminum salt. A method for producing an 8-oxyquinoline-aluminum salt, which comprises precipitating crystals.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1222294A JPH07196620A (en) | 1994-01-10 | 1994-01-10 | Method for producing 8-oxyquinoline-aluminum salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1222294A JPH07196620A (en) | 1994-01-10 | 1994-01-10 | Method for producing 8-oxyquinoline-aluminum salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07196620A true JPH07196620A (en) | 1995-08-01 |
Family
ID=11799358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1222294A Withdrawn JPH07196620A (en) | 1994-01-10 | 1994-01-10 | Method for producing 8-oxyquinoline-aluminum salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07196620A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001025211A1 (en) * | 1999-10-06 | 2001-04-12 | 3M Innovative Properties Company | Method of making metal 8-quinolinolato complexes |
| WO2010118661A1 (en) * | 2009-04-13 | 2010-10-21 | 北京阿格蕾雅科技发展有限公司 | Method for preparation metal compounds of 8-hydroxyquinoline or derivatives |
| CN103183699A (en) * | 2011-12-27 | 2013-07-03 | 北京有色金属研究总院 | Electroluminescent material, preparation method for same, and luminescent device prepared from electroluminescent material |
-
1994
- 1994-01-10 JP JP1222294A patent/JPH07196620A/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001025211A1 (en) * | 1999-10-06 | 2001-04-12 | 3M Innovative Properties Company | Method of making metal 8-quinolinolato complexes |
| US6362339B1 (en) | 1999-10-06 | 2002-03-26 | 3M Innovative Properties Company | Method of making metal 8-quinolinolato complexes |
| WO2010118661A1 (en) * | 2009-04-13 | 2010-10-21 | 北京阿格蕾雅科技发展有限公司 | Method for preparation metal compounds of 8-hydroxyquinoline or derivatives |
| CN103183699A (en) * | 2011-12-27 | 2013-07-03 | 北京有色金属研究总院 | Electroluminescent material, preparation method for same, and luminescent device prepared from electroluminescent material |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Withdrawal of application because of no request for examination |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20010403 |