JPH0133109B2 - - Google Patents
Info
- Publication number
- JPH0133109B2 JPH0133109B2 JP23859284A JP23859284A JPH0133109B2 JP H0133109 B2 JPH0133109 B2 JP H0133109B2 JP 23859284 A JP23859284 A JP 23859284A JP 23859284 A JP23859284 A JP 23859284A JP H0133109 B2 JPH0133109 B2 JP H0133109B2
- Authority
- JP
- Japan
- Prior art keywords
- indium
- reaction
- diisopropylate
- triisopropylate
- structural formula
- 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
- 229910052738 indium Inorganic materials 0.000 claims description 18
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 16
- QJTLYPUUVWZDEG-UHFFFAOYSA-N C(C)OC(CC(=O)C)=O.[In] Chemical compound C(C)OC(CC(=O)C)=O.[In] QJTLYPUUVWZDEG-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004020 conductor Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000007650 screen-printing Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000002472 indium compounds Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- -1 Indium organic acids Chemical class 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、透明導電体形成に有用なインジウム
モノエチルアセトアセテートジイソプロピレート
およびその製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to indium monoethyl acetoacetate diisopropylate useful for forming a transparent conductor and a method for producing the same.
従来の技術
近年インジウムの酸化物被膜が液晶素子の透明
導電膜に使用されるようになり、インジウムの金
属としての特性を利用すべく、その応用範囲が拡
大してきている。BACKGROUND OF THE INVENTION In recent years, indium oxide films have come to be used as transparent conductive films for liquid crystal devices, and the range of applications has been expanding to take advantage of the properties of indium as a metal.
このような酸化物被膜の形成方法には、化学ス
プレー法、真空蒸着法、スクリーン印刷法等があ
る。化学スプレー法は比較的大面積の形状の被膜
を得るには有利であるが、微細で複雑な形状のも
のをえるにはエツチング処理等の余分な工程が必
要となり経済的に不利である。真空蒸着法は、最
近マスク蒸着法が発達し、エツチング処理は必要
でなくなつたが、バツチ式である為、大量生産に
好適とはいい難い。スクリーン印刷法では、上記
のような問題がなく、目的形状のものを印刷焼成
により容易に得ることができ、しかもエツチング
処理にともなう廃液処理の必要もないという利点
を有する。 Methods for forming such an oxide film include a chemical spray method, a vacuum evaporation method, a screen printing method, and the like. Although the chemical spray method is advantageous in obtaining a film with a relatively large area, it is economically disadvantageous because extra steps such as etching are required to obtain a film with a fine and complex shape. The vacuum evaporation method has recently developed into a mask evaporation method and no longer requires etching, but since it is a batch method, it is not suitable for mass production. The screen printing method has the advantage that it does not have the above-mentioned problems, that it can easily obtain the desired shape by printing and firing, and that there is no need for waste liquid treatment associated with etching treatment.
しかし、従来のインジウム化合物を含む透明導
電性被膜形成用ペーストは、それ自体の安定性が
良くないため、スクリーン印刷時の作業性も悪
く、また、形成された被膜の導電性についてもバ
ラツキが大きいという欠点があつた。 However, conventional pastes for forming transparent conductive films containing indium compounds do not have good stability themselves, resulting in poor workability during screen printing, and the conductivity of the formed films also varies widely. There was a drawback.
すなわち、従来、透明導電体形成用インジウム
化合物としては、オクチル酸インジウム
〔（C7H15CO2）3In〕のような有機酸インジウムや、
インジウムトリスアセチルアセトナート〔In
（acac）3〕が使用されている。 That is, conventional indium compounds for forming transparent conductors include organic acid indium such as indium octylate [(C 7 H 15 CO 2 ) 3 In],
Indium trisacetylacetonate [In
(acac) 3 ] is used.
有機酸インジウムは一般に加水分解しやすく、
またペーストとした場合、ペーストのゲル化を促
進する等、比較的容易に化学変化するという欠点
を持つており、このため、有機酸インジウムを含
有するペーストの寿命が短く、スクリーン印刷時
の作業性を悪くする原因となつている。 Indium organic acids are generally easy to hydrolyze;
In addition, when made into a paste, it has the disadvantage of being relatively easily chemically changed, such as promoting gelation of the paste.For this reason, the life of the paste containing indium organic acid is short, and the workability during screen printing is It is the cause of deterioration.
発明が解決しようとする問題点
本発明は、従来の透明導電体形成用インジウム
化合物の欠点を解消し、すなわち化学的安定性に
すぐれ、かつスクリーン印刷操作の容易なインジ
ウム化合物を提供し、かつ、その製造方法を提供
するものである。Problems to be Solved by the Invention The present invention eliminates the drawbacks of conventional indium compounds for forming transparent conductors, that is, provides an indium compound with excellent chemical stability and easy screen printing operation, and The present invention provides a method for manufacturing the same.
問題を解決するための手段
上記問題点は、下記構造式(1)：
で示されるインジウムモノエチルアセトアセテー
トジイソプロピレートにより解消される。Means to solve the problem The above problem is solved by the following structural formula (1): It is solved by indium monoethyl acetoacetate diisopropylate shown in
また、上記インジウムモノエチルアセトアセテ
ートジイソプロピレートは、下記構造式(2)：
で示されるインジウムトリイソプロピレートと、
下記構造式(3)：
で示されるアセト酢酸エチルとを反応させること
を特徴とする本発明方法によつて製造される。 In addition, the above indium monoethyl acetoacetate diisopropylate has the following structural formula (2): Indium triisopropylate represented by
Structural formula (3) below: It is produced by the method of the present invention, which is characterized by reacting with ethyl acetoacetate represented by:
作用および実施例
本発明にかかるインジウムモノエチルアセトア
セテートジイソプロピレートは、良好な化学的安
定性と、有機溶媒に対する良好な溶解性を有して
いる。このためインジウムモノエチルアセトアセ
テートジイソプロピレートを、例えばベンゼン、
又は酢酸エチルなどの有機溶媒に高濃度で均一に
溶解させることができ、得られたペーストは、透
明導電体、例えば皮膜などの形成用に使用するこ
とができる。Effects and Examples Indium monoethylacetoacetate diisopropylate according to the present invention has good chemical stability and good solubility in organic solvents. For this purpose, indium monoethyl acetoacetate diisopropylate, for example benzene,
Alternatively, it can be uniformly dissolved at a high concentration in an organic solvent such as ethyl acetate, and the resulting paste can be used for forming a transparent conductor, such as a film.
本発明方法においては、インジウムトリイソプ
ロピレート１モル部に対しアセト酢酸エチル１モ
ル部が反応し、１モル部のインジウムモノエチル
アセトアセテートジイソプロピレートが得られ
る。この反応において、所望量のインジウムトリ
イソプロピレートを有機溶媒に溶解し、この溶液
に、所定量のアセト酢酸エチルを滴下混合しても
よい。或は、インジウムトリイソプロピレート
と、アセト酢酸エチルとの所定量を、別々に有機
溶媒に溶解しておき、これら両溶液を混合しても
よい。 In the method of the present invention, 1 mole part of indium triisopropylate is reacted with 1 mole part of ethyl acetoacetate to obtain 1 mole part of indium monoethyl acetoacetate diisopropylate. In this reaction, a desired amount of indium triisopropylate may be dissolved in an organic solvent, and a predetermined amount of ethyl acetoacetate may be added dropwise to this solution. Alternatively, predetermined amounts of indium triisopropylate and ethyl acetoacetate may be dissolved separately in an organic solvent, and these two solutions may be mixed.
上記いづれの反応操作においても、反応系を、
所定温度に保持しながら反応が完了するまで撹拌
する。反応が完了したならば反応系から有機溶媒
と、生成したイソプロピルアルコールとを常圧、
又は、減圧下に蒸留して除去して、目的の化合物
を得る。 In any of the above reaction operations, the reaction system is
Stir while maintaining the specified temperature until the reaction is complete. Once the reaction is complete, the organic solvent and the produced isopropyl alcohol are removed from the reaction system under normal pressure.
Alternatively, the target compound is obtained by distilling and removing under reduced pressure.
上記の反応において、反応温度に格別の限定は
ないが一般に室温以上100℃以下の温度が好まし
い。反応温度を100℃より高くしても格別の効果
はなく、却つて経済的に不利となる。上記の反応
温度範囲内では、反応時間は数分ないし数時間で
ある。 In the above reaction, the reaction temperature is not particularly limited, but generally a temperature of room temperature or higher and 100°C or lower is preferred. Even if the reaction temperature is made higher than 100°C, there is no particular effect and it becomes economically disadvantageous. Within the above reaction temperature range, the reaction time is from several minutes to several hours.
本発明方法の反応に用いられる溶媒は、インジ
ウムトリイソプロピレート、アセト酢酸エチル、
およびインジウムモノエチルアセトアセテートジ
イソプロピレートに対し、化学的反応性に乏し
く、しかし、溶解性にすぐれているものであれ
ば、格別の限定はないが、一般に、ベンゼン、ト
ルエン、キシレンなどから選ばれる少くとも１種
からなるものが好ましい。 The solvent used in the reaction of the method of the present invention is indium triisopropylate, ethyl acetoacetate,
There is no particular limitation, as long as it has poor chemical reactivity with indium monoethyl acetoacetate diisopropylate but has excellent solubility, but it is generally selected from benzene, toluene, xylene, etc. Preferably, it consists of at least one type.
前述のように、反応完了後、反応系から有機溶
媒およびイソプロピルアルコールが常圧、又は減
圧下で蒸留除去される。使用した溶媒の沸点が、
インジウムモノエチルアセトアセテートジイソプ
ロピレートの分解点以上である場合、上記蒸留除
去操作を減圧下において、上記目的化合物の分解
点より低い温度で行うことが好ましい。 As mentioned above, after the reaction is completed, the organic solvent and isopropyl alcohol are distilled off from the reaction system under normal pressure or reduced pressure. The boiling point of the solvent used is
When the temperature is higher than the decomposition point of indium monoethyl acetoacetate diisopropylate, the distillation removal operation is preferably carried out under reduced pressure at a temperature lower than the decomposition point of the target compound.
本発明のインジウムモノエチルアセトアセテー
トジイソプロピレートは、有機溶媒に溶解し易く
高濃度のペーストが容易に得られるので、このペ
ーストは、特に液晶素子の透明導電性皮膜形成用
に好適である。 The indium monoethyl acetoacetate diisopropylate of the present invention is easily dissolved in an organic solvent and a highly concentrated paste can be easily obtained, so this paste is particularly suitable for forming a transparent conductive film of a liquid crystal element.
このような透明導電性皮膜形成用ペーストを得
るには、本発明のインジウムモノエチルアセトア
セテートジイソプロピレートを、２〜20重量％の
濃度で、有機溶媒、例えばベンゼン、酢酸エチ
ル、又はメチルエチルケトンなどに溶解すればよ
い。このとき、抵抗値調整剤として、スズの有機
錯化合物、例えばジブチルスズアセテートを、イ
ンジウムに対するスズの原子比が５〜30％になる
ように、上記ペーストに添加すれば、より抵抗値
の低い透明導電性皮膜、例えば電極が得られる。 To obtain such a paste for forming a transparent conductive film, indium monoethyl acetoacetate diisopropylate of the present invention is dissolved in an organic solvent such as benzene, ethyl acetate, or methyl ethyl ketone at a concentration of 2 to 20% by weight. Just dissolve it. At this time, if an organic complex compound of tin, such as dibutyltin acetate, is added to the above paste as a resistance value adjusting agent so that the atomic ratio of tin to indium is 5 to 30%, it is possible to conduct a transparent conductive material with a lower resistance value. A transparent film, such as an electrode, is obtained.
実施例 １
500mlの四つ口フラスコに撹はん機、温度計、
滴下ロート、および乾燥管付き冷却管をとりつ
け、このフラスコ中にインジウムトリイソプロピ
レート35.05ｇ（120ミリモル）、およびベンゼン
300mlを入れ、室温で撹はんしながら、滴下ロー
トよりアセト酢酸エチル15.62ｇ（120ミリモル）
を５分間で滴下した。滴下終了後、反応混合物を
80℃に加熱して30分間還流し、その後、不溶分を
ろ去し、ベンゼンと生成したイソプロピルアルコ
ールを留出させて、ろ液を減圧下に濃縮し、残渣
としてインジウムモノエチルアセトアセテートジ
イソプロピレート42.15ｇ（収率97.0％）を得た。
この生成物のNMRの測定結果は次のようであつ
た。Example 1 A 500ml four-necked flask with a stirrer, thermometer,
A dropping funnel and a cooling tube with a drying tube were installed, and 35.05 g (120 mmol) of indium triisopropylate and benzene were placed in this flask.
Add 300 ml of ethyl acetoacetate and add 15.62 g (120 mmol) of ethyl acetoacetate from the dropping funnel while stirring at room temperature.
was added dropwise over 5 minutes. After the addition is complete, the reaction mixture is
Heating to 80°C and refluxing for 30 minutes, then filtering off insoluble matter, distilling off benzene and the generated isopropyl alcohol, and concentrating the filtrate under reduced pressure to leave a residue of indium monoethyl acetoacetate diisopropylene. 42.15 g (yield 97.0%) of the product was obtained.
The NMR measurement results of this product were as follows.
1HNMR（CDCl3）δ（ppm）
0.9−1.6 （br、15H）
1.88 （ｓ、3H）
3.8−4.4 （ｍ、4H）
4.91 （ｓ、1H）
また、この生成物のインジウム含量をキレート滴
定により測定したところ31.9％（理論値31.70％）
であり、また、その赤外特性吸収は、
キレートＣ＝Ｏ構造：1625cm-1、および
キレートＣ＝Ｃ構造：1519cm-1
であつた。 1 HNMR (CDCl 3 ) δ (ppm) 0.9−1.6 (br, 15H) 1.88 (s, 3H) 3.8−4.4 (m, 4H) 4.91 (s, 1H) In addition, the indium content of this product was determined by chelate titration. Measured: 31.9% (theoretical value: 31.70%)
The infrared characteristic absorption was as follows: Chelate C=O structure: 1625 cm -1 and Chelate C=C structure: 1519 cm -1 .
実施例 ２
実施例１と同様の操作を行つた。但し、インジ
ウムトリイソプロピレートとアセト酢酸エチルと
を、別々にそれぞれ150mlのベンゼンに溶解し、
フラスコ中で、両溶液を混合して、反応させた。Example 2 The same operation as in Example 1 was performed. However, indium triisopropylate and ethyl acetoacetate are each dissolved separately in 150 ml of benzene,
Both solutions were mixed and reacted in a flask.
得られた生成物の収率は96.5％であり、この生
成物は実施例１記載と同様のNMR測定結果およ
びインジウム含有率を示した。 The yield of the product obtained was 96.5%, and the product showed the same NMR measurement results and indium content as described in Example 1.
発明の効果
本発明のインジウムモノエチルアセトアセテー
トジイソプロピレートは、良好な安定性と有機溶
媒溶解性を示すので、透明導電性皮膜形成用に有
用なものである。また本発明方法によりインジウ
ムモノエチルアセトアセテートジイソプロピレー
トが良好な収率をもつて得られる。Effects of the Invention The indium monoethylacetoacetate diisopropylate of the present invention exhibits good stability and solubility in organic solvents, and is therefore useful for forming transparent conductive films. Furthermore, indium monoethyl acetoacetate diisopropylate can be obtained in good yield by the method of the present invention.
Claims (1)
トジイソプロピレート。 ２ 下記構造式(2)： で示されるインジウムトリイソプロピレートと、
下記構造式(3)： で示されるアセト酢酸エチルとを反応させること
を特徴とする、下記構造式(1) で示されるインジウムモノエチルアセトアセテー
トジイソプロピレートの製造方法。 ３ 前記インジウムトリイソプロピレートとアセ
ト酢酸エチルとの反応が室温から100℃までの温
度で行われる、特許請求の範囲第２項記載の方
法。[Claims] 1. Structural formula (1) below: Indium monoethyl acetoacetate diisopropylate. 2 Structural formula (2) below: Indium triisopropylate represented by
Structural formula (3) below: The following structural formula (1) is characterized by reacting with ethyl acetoacetate represented by A method for producing indium monoethyl acetoacetate diisopropylate shown in 3. The method of claim 2, wherein the reaction of the indium triisopropylate and ethyl acetoacetate is carried out at a temperature from room temperature to 100°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23859284A JPS61118389A (en) | 1984-11-14 | 1984-11-14 | Indium monoethylacetoaceteate diisopropylate and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23859284A JPS61118389A (en) | 1984-11-14 | 1984-11-14 | Indium monoethylacetoaceteate diisopropylate and preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61118389A JPS61118389A (en) | 1986-06-05 |
| JPH0133109B2 true JPH0133109B2 (en) | 1989-07-11 |
Family
ID=17032488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23859284A Granted JPS61118389A (en) | 1984-11-14 | 1984-11-14 | Indium monoethylacetoaceteate diisopropylate and preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61118389A (en) |
-
1984
- 1984-11-14 JP JP23859284A patent/JPS61118389A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61118389A (en) | 1986-06-05 |
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