JP3738525B2 - Poly (phenylene) having ethylene oxide chain in side chain and method for producing the same - Google Patents
Poly (phenylene) having ethylene oxide chain in side chain and method for producing the same Download PDFInfo
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- JP3738525B2 JP3738525B2 JP10161897A JP10161897A JP3738525B2 JP 3738525 B2 JP3738525 B2 JP 3738525B2 JP 10161897 A JP10161897 A JP 10161897A JP 10161897 A JP10161897 A JP 10161897A JP 3738525 B2 JP3738525 B2 JP 3738525B2
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- ethylene oxide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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Description
【０００１】
【発明の属する技術分野】
本発明は、導電性高分子、特に表示材料または電池用途の電極材料として有用である、エチレンオキシド鎖を有する新規なポリ（フェニレン）およびその製造方法に関する。
【０００２】
【従来の技術】
ポリ（フェニレン）は導電性高分子として、特に高分子発光素子への応用が期待されている。この分野では、高分子発光電気化学素子（ＬＥＣ）といわれる素子が最近提案され、その発光効率の高さから着目されている。その構造は両電極間に導電性高分子とイオン伝導性を有するポリエチレンオキシドおよび支持塩からなる高分子膜を挟んだもので、電極からの正負電荷の注入とドーパントとなる支持塩の正負両イオンの移動により、膜中でｐ−ｎ接合が形成されることが動作原理となっていると推定される。電子伝導性を有する導電性高分子にさらにイオン伝導性をも付与することができれば、前記のような複合膜ではなく単一の材料で素子の製造が可能になり、プロセス上大きな利点がある。
【０００３】
また、導電性高分子はしばしばポリマー電池などの電極材料としても利用されている。電極活物質と電解質成分との界面のイオン抵抗が高いこと、あるいは活物質と集電体との電子伝導性が問題であり、電子伝導性とイオン伝導性とを併せ持つ高分子材料はその解決策として期待できる。
【０００４】
しかしながら、電子伝導性とイオン伝導性とを併せ持つ高分子材料については従来ほとんど知られていない。エチレンオキシド鎖を有するポリ（フェニレン）誘導体として、J. Am. Chem. Soc., Vol. 118, pp 7416-7417 (1996)には、ポリ［９，９−ビス（３，６−ジオキサヘプチル）フルオレン−２，７−ジイル］が報告されているが、原料モノマーの製造が煩雑であるという問題があった。
【０００５】
【発明が解決しようとする課題】
かかる状況下、本発明が解決しようとする課題、即ち本発明の目的は、新規なエチレンオキシド鎖を有するポリ（フェニレン）およびその工業的に有利な製造方法を提供することにある。
【０００６】
【課題を解決するための手段】
本発明者らは上記目的を達成するべく鋭意研究を行った結果、安価な原料を用いて温和な条件下に短いステップで容易に新規なエチレンオキシド鎖を有するポリ（フェニレン）が得られることを見出し本発明を完成するに至った。即ち本発明は、下記一般式［１］で表されるエチレンオキシド鎖を有するポリ（フェニレン）、および下記一般式［３］で表わされるジアルコキシベンゼンを酸化重合するエチレンオキシド鎖を有するポリ（フェニレン）の製造方法にかかるものである。
【０００７】
【発明の実施の形態】
以下、本発明を詳細に説明する。
上記一般式［１］においてＲ1は上記一般式［２］で表わされるエチレンオキシド鎖を表わす。一般式［２］におけるＲ3〜Ｒ6は水素原子または炭素数１〜１０の炭化水素基を表わす。炭化水素基としてはアルキル基が好ましく、具体例としてはメチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｉｓｏ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基、オクチル基などが例示される。Ｒ3〜Ｒ6は好ましくは、水素原子またはメチル基であり、最も好ましくは水素原子である。
【０００８】
上記一般式［２］においてＲ7は炭素数１〜１０の炭化水素基を表わす。炭化水素基としてはアルキル基が好ましく、具体例としてはメチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｉｓｏ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基、オクチル基などが例示される。Ｒ7は好ましくは、炭素数１〜５の炭化水素基であり、さらに好ましくはメチル基またはエチル基である。
【０００９】
上記一般式［２］においてｍは１〜１０の整数である。ｍは好ましくは１〜５であり、より好ましくは１〜３である。
【００１０】
上記一般式［１］においてＲ2は炭素数１〜１０の炭化水素基または一般式［２］で表わされるエチレンオキシド鎖を表わす。炭化水素基としてはアルキル基が好ましく、具体例としてはメチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｉｓｏ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基、オクチル基などが例示される。炭化水素基として好ましくは、炭素数１〜５の炭化水素基であり、さらに好ましくはメチル基またはエチル基である。
【００１１】
上記一般式［１］においてｎは平均の重合度で２以上の数を表わす。ｎは好ましくは３〜１００である。さらに好ましくは、５〜５０である。
【００１２】
本発明のポリ（フェニレン）は、下記一般式［３］で表されるエチレンオキシド鎖を有するジアルコキシベンゼン類を酸化重合することにより製造可能である。
【００１３】
上記一般式［３］で表されるエチレンオキシド鎖を有するジアルコキシベンゼン類は、安価な原料であるハイドロキノンまたはそのモノアルキルエーテルと、エチレンオキシドのハロゲン化物とをアルカリ存在下に反応させて容易に合成することが可能である。ハイドロキノンを原料に用いればベンゼン環の両側にエチレンオキシド鎖を有するポリ（フェニレン）を、ハイドロキノンモノアルキルエーテルからはベンゼン環の片方にエチレンオキシド鎖を有しもう片方にアルコキシ基を有するポリ（フェニレン）を製造することができる。
【００１４】
上記一般式［３］で表されるエチレンオキシド鎖を有するジアルコキシベンゼン類を重合してポリ（フェニレン）を得る際には、遷移金属錯体触媒、なかでもオキソバナジウム（IV）錯体を触媒に用いて、酸化剤、酸および溶媒存在下に酸化重合する方法が選択性および経済性の上で好ましく用いられる。
【００１５】
触媒の具体例としては、ビス（アセチルアセトナト）オキソバナジウム（IV）錯体、ビス（ベンゾイルアセトナト）オキソバナジウム（IV）錯体、ビス（ジベンゾイルメタナト）オキソバナジウム（IV）錯体、ビス（トリフルオロアセチルアセトナト）オキソバナジウム（IV）錯体、ビス（ヘキサフルオロアセチルアセトナト）オキソバナジウム（IV）錯体等のオキソバナジウム錯体が挙げられる。触媒の使用量は原料であるジアルコキシベンゼンに対して通常０．００１〜１０倍のモル比で用いられる。
【００１６】
酸化剤としては重合活性が維持される限り任意のものが使用できるが、好ましくは酸素が用いられる。酸素源として好ましくは酸素ガスまたは空気が用いられ、大気圧または加圧下において反応が行われる。
【００１７】
酸としては通常、プロトン酸および／または酸無水物が用いられる。酸としてはプロトン酸と酸無水物を併用することが好ましい。
【００１８】
プロトン酸としては強酸性のものが好ましく、具体的には硫酸、トリフルオロ酢酸、トリフルオロメタンスルホン酸などが例示される。より好ましくはトリフルオロメタンスルホン酸が用いられる。プロトン酸の使用量は、原料である芳香族化合物に対して通常０．００１〜１０倍のモル比で用いられる。
【００１９】
酸無水物として好ましくは、無水トリフルオロ酢酸または無水トリフルオロメタンスルホン酸が用いられる。酸無水物の使用量は、原料である芳香族化合物に対して通常０．００１〜１０倍のモル比で用いられる。
【００２０】
酸化重合反応は溶媒の非存在下でも行えるが、通常は溶媒の存在下で行われる。溶媒としては重合活性が維持される限り任意のものが使用できるが、好ましくは非プロトン性溶媒が用いられる。具体的には、ベンゼン、トルエン、ジクロロメタン、クロロホルム、ジクロロエタン、クロロベンゼン、ジクロロベンゼン、ニトロメタン、ニトロベンゼン、ベンゾニトリル等が例示される。溶媒の使用量は原料である芳香族化合物に対して、１〜１００倍の重量比で用いられる。
【００２１】
【実施例】
以下に実施例を挙げて本発明をさらに詳細に説明するが、本発明はこれらの実施例によりその範囲を限定されるものではない。
【００２２】
参考例１
下記式［４］で表わされるモノマー、１−（２−（２−メトキシエトキシ）エトキシ−４−メトキシベンゼン（以下ＭＥ２ＰＭと略すことがある。）の合成例である。
【００２３】
参考例２
１−クロロ−２−（２−メトキシエトキシ）エタンに代えて１−クロロ−２−（２−（２−メトキシエトキシ）エトキシ）エタン３．５８ｇ（２０ｍｍｏｌ）を用いた他は参考例１を繰り返すことにより、下記式［５］で表わされるモノマー、１−（２−（２−（２−メトキシエトキシ）エトキシ）エトキシ−４−メトキシベンゼン（以下ＭＥ３ＰＭと略すことがある。）を、１０ｍｍＨｇで沸点が１９０℃の無色液体として３．３５ｇ得た。1Ｈ−および13Ｃ−ＮＭＲスペクトル測定結果から得られた化合物がＭＥ３ＰＭである事が確認された。
参考例３
ハイドロキノン１１．０ｇ（０．１ｍｏｌ）、２−クロロエチルエーテル２３．９ｇ（０．２２ｍｏｌ）、塩化ベンジルトリエチルアンモニウム４．５６ｇ（０．０２ｍｏｌ）、トルエン１２０ｍｌ、およびジメチルスルホキシド４０ｍｌを用いて、参考例１と同様の反応を行い、下記式［５］で表わされるモノマー、１，４−ビス（２−エトキシエトキシ）ベンゼン（以下ＢＥ２Ｐと略すことがある。）を、２．５ｍｍＨｇで沸点が１４０℃の無色液体として４．４３ｇ得た。1Ｈ−および13Ｃ−ＮＭＲスペクトル測定結果から得られた化合物がＢＥ２Ｐである事が確認された。
実施例１
マグネチックスターラ、酸素導入管および還流冷却器を備えた５０ｍｌフラスコ中に，ビス（アセチルアセトナト）オキソバナジウム（以下ＶＯ（ａｃａｃ）2と略すことがある。）０．２１ｇ（０．８ｍｍｏｌ）とＭＥ２ＰＭ ２．２６ｇ（１０ｍｍｏｌ）を入れ、１，２−ジクロロエタン２０ｍｌを加え撹拌溶解した。これにトリフルオロメタンスルホン酸０．２ｍｌと無水トリフルオロ酢酸４．０ｍｌを順次加えた。酸素ガスを吹き込みながら５０℃で１２０時間撹拌を続けた。反応終了後反応混合物を濃塩酸１ｍｌを含むメタノール２００ｍｌ中に注ぎ込んだ。沈澱物を濾取し、５０℃で５時間減圧乾燥して、０．５９ｇのポリ（２−メトキシ−５−（２−（２−メトキシエトキシ）エトキシ）−１，４−フェニレン）が褐色粉末として得られた。ＩＲスペクトルデータを図１に示す。
【００２６】
実施例２
ＭＥ２ＰＭに代えてＭＥ３ＰＭ ２．７０ｇを用いて実施例１を繰り返した結果、０．１８ｇのポリ（２−メトキシ−５−（２−（２−（２−メトキシエトキシ）エトキシ）エトキシ）−１，４−フェニレン）が褐色粉末として得られた。ＩＲスペクトルデータを図１に示す。
【００２７】
実施例３
ＭＥ２ＰＭに代えてＢＥ２Ｐ １．２７ｇを用い、ＶＯ（ａｃａｃ）2を１３３ｍｇ、トリフルオロメタンスルホン酸を０．１ｍｌ、無水トリフルオロ酢酸を１．５ｍｌとして実施例１と同様の酸化重合を４０℃で５２時間行った結果、０．４２ｇのポリ（２，５−ビス（２−エトキシエトキシ）−１，４−フェニレン）が褐色粉末として得られた。
【００２８】
【発明の効果】
本発明により導電性高分子、特に表示材料または電池用途の電極材料として有用なエチレンオキシド鎖を有するポリ（フェニレン）、およびそれを安価な原料を用いて温和な条件下に短いステップで容易に製造する方法が提供される。
【図面の簡単な説明】
【図１】図１は実施例１および実施例２で得られたポリマーのＩＲスペクトルデータである。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel poly (phenylene) having an ethylene oxide chain, which is useful as a conductive polymer, particularly as an electrode material for display materials or battery applications, and a method for producing the same.
[0002]
[Prior art]
Poly (phenylene) is expected to be applied to a polymer light emitting device as a conductive polymer. In this field, an element called a polymer light-emitting electrochemical element (LEC) has recently been proposed, and has attracted attention because of its high luminous efficiency. The structure consists of a conductive polymer, a polymer membrane composed of polyethylene oxide and supporting salt having ion conductivity between both electrodes, positive and negative charges injected from the electrode and positive and negative ions of the supporting salt as a dopant. It is presumed that the operation principle is that a pn junction is formed in the film by the movement of. If ionic conductivity can be further imparted to the conductive polymer having electron conductivity, the device can be manufactured with a single material instead of the composite film as described above, which has a great advantage in terms of process.
[0003]
Conductive polymers are also often used as electrode materials for polymer batteries and the like. High ionic resistance at the interface between the electrode active material and the electrolyte component, or the electronic conductivity between the active material and the current collector is a problem, and polymer materials that combine both electron conductivity and ionic conductivity are the solution. As expected.
[0004]
However, little is known about polymer materials having both electron conductivity and ion conductivity. As a poly (phenylene) derivative having an ethylene oxide chain, J. Am. Chem. Soc., Vol. 118, pp 7416-7417 (1996) includes poly [9,9-bis (3,6-dioxaheptyl). Fluorene-2,7-diyl] has been reported, but there was a problem that the production of the raw material monomer was complicated.
[0005]
[Problems to be solved by the invention]
Under such circumstances, a problem to be solved by the present invention, that is, an object of the present invention is to provide a poly (phenylene) having a novel ethylene oxide chain and an industrially advantageous production method thereof.
[0006]
[Means for Solving the Problems]
As a result of intensive studies to achieve the above object, the present inventors have found that poly (phenylene) having a novel ethylene oxide chain can be easily obtained in a short step under mild conditions using an inexpensive raw material. The present invention has been completed. That is, the present invention relates to poly (phenylene) having an ethylene oxide chain represented by the following general formula [1] and poly (phenylene) having an ethylene oxide chain that oxidatively polymerizes dialkoxybenzene represented by the following general formula [3]. It relates to the manufacturing method.
[0007]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
In the general formula [1], R 1 represents an ethylene oxide chain represented by the general formula [2]. R < 3 > -R < 6 > in General formula [2] represents a hydrogen atom or a C1-C10 hydrocarbon group. The hydrocarbon group is preferably an alkyl group, and specific examples include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. And an octyl group. R 3 to R 6 are preferably a hydrogen atom or a methyl group, and most preferably a hydrogen atom.
[0008]
In the general formula [2], R 7 represents a hydrocarbon group having 1 to 10 carbon atoms. The hydrocarbon group is preferably an alkyl group, and specific examples include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. And an octyl group. R 7 is preferably a hydrocarbon group having 1 to 5 carbon atoms, more preferably a methyl group or an ethyl group.
[0009]
In the said General formula [2], m is an integer of 1-10. m is preferably 1 to 5, and more preferably 1 to 3.
[0010]
In the general formula [1], R 2 represents a hydrocarbon group having 1 to 10 carbon atoms or an ethylene oxide chain represented by the general formula [2]. The hydrocarbon group is preferably an alkyl group, and specific examples include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. And an octyl group. The hydrocarbon group is preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably a methyl group or an ethyl group.
[0011]
In the general formula [1], n represents an average degree of polymerization and represents a number of 2 or more. n is preferably 3 to 100. More preferably, it is 5-50.
[0012]
The poly (phenylene) of the present invention can be produced by oxidative polymerization of dialkoxybenzenes having an ethylene oxide chain represented by the following general formula [3].
[0013]
Dialkoxybenzenes having an ethylene oxide chain represented by the general formula [3] are easily synthesized by reacting an inexpensive raw material hydroquinone or a monoalkyl ether thereof with a halide of ethylene oxide in the presence of an alkali. It is possible. If hydroquinone is used as a raw material, poly (phenylene) having ethylene oxide chains on both sides of the benzene ring is produced. From hydroquinone monoalkyl ether, poly (phenylene) having ethylene oxide chains on one side of the benzene ring and alkoxy groups on the other side is produced. can do.
[0014]
When poly (phenylene) is obtained by polymerizing a dialkoxybenzene having an ethylene oxide chain represented by the above general formula [3], a transition metal complex catalyst, especially an oxovanadium (IV) complex is used as a catalyst. In view of selectivity and economy, a method of oxidative polymerization in the presence of an oxidizing agent, an acid and a solvent is preferably used.
[0015]
Specific examples of the catalyst include bis (acetylacetonato) oxovanadium (IV) complex, bis (benzoylacetonato) oxovanadium (IV) complex, bis (dibenzoylmethanato) oxovanadium (IV) complex, bis (trifluoro And oxovanadium complexes such as acetylacetonato) oxovanadium (IV) complex and bis (hexafluoroacetylacetonato) oxovanadium (IV) complex. The amount of the catalyst used is usually 0.001 to 10 times the molar ratio of dialkoxybenzene which is a raw material.
[0016]
Any oxidizing agent can be used as long as the polymerization activity is maintained, but oxygen is preferably used. Oxygen gas or air is preferably used as the oxygen source, and the reaction is performed at atmospheric pressure or under pressure.
[0017]
As the acid, a protonic acid and / or an acid anhydride is usually used. As the acid, it is preferable to use a protonic acid and an acid anhydride in combination.
[0018]
As the protic acid, a strongly acidic acid is preferable, and specifically, sulfuric acid, trifluoroacetic acid, trifluoromethanesulfonic acid and the like are exemplified. More preferably, trifluoromethanesulfonic acid is used. The amount of the protonic acid used is usually 0.001 to 10 times the molar ratio of the aromatic compound as the raw material.
[0019]
Preferably, trifluoroacetic anhydride or trifluoromethanesulfonic anhydride is used as the acid anhydride. The usage-amount of an acid anhydride is normally used by the molar ratio of 0.001-10 times with respect to the aromatic compound which is a raw material.
[0020]
Although the oxidative polymerization reaction can be carried out in the absence of a solvent, it is usually carried out in the presence of a solvent. Any solvent can be used as long as the polymerization activity is maintained, but an aprotic solvent is preferably used. Specific examples include benzene, toluene, dichloromethane, chloroform, dichloroethane, chlorobenzene, dichlorobenzene, nitromethane, nitrobenzene, and benzonitrile. The amount of the solvent used is 1 to 100 times the weight ratio of the aromatic compound as the raw material.
[0021]
【Example】
The present invention will be described in more detail with reference to the following examples, but the scope of the present invention is not limited by these examples.
[0022]
Reference example 1
This is a synthesis example of a monomer represented by the following formula [4], 1- (2- (2-methoxyethoxy) ethoxy-4-methoxybenzene (hereinafter sometimes abbreviated as ME2PM).
[0023]
Reference example 2
Reference Example 1 was repeated except that 3.58 g (20 mmol) of 1-chloro-2- (2- (2-methoxyethoxy) ethoxy) ethane was used instead of 1-chloro-2- (2-methoxyethoxy) ethane. Thus, the monomer represented by the following formula [5], 1- (2- (2- (2-methoxyethoxy) ethoxy) ethoxy-4-methoxybenzene (hereinafter sometimes abbreviated as ME3PM), has a boiling point at 10 mmHg. Was obtained as a colorless liquid at 190 ° C. It was confirmed that the compound obtained from 1 H- and 13 C-NMR spectrum measurement results was ME3PM.
Reference example 3
Reference example using 11.0 g (0.1 mol) of hydroquinone, 23.9 g (0.22 mol) of 2-chloroethyl ether, 4.56 g (0.02 mol) of benzyltriethylammonium chloride, 120 ml of toluene, and 40 ml of dimethyl sulfoxide 1 and a monomer represented by the following formula [5], 1,4-bis (2-ethoxyethoxy) benzene (hereinafter sometimes abbreviated as BE2P), has a boiling point of 140 ° C. at 2.5 mmHg. As a colorless liquid, 4.43 g was obtained. It was confirmed that the compound obtained from the 1 H- and 13 C-NMR spectrum measurement results was BE2P.
Example 1
In a 50 ml flask equipped with a magnetic stirrer, an oxygen introduction tube and a reflux condenser, 0.21 g (0.8 mmol) of bis (acetylacetonato) oxovanadium (hereinafter sometimes abbreviated as VO (acac) 2 ) 2.26 g (10 mmol) of ME2PM was added, 20 ml of 1,2-dichloroethane was added and dissolved by stirring. To this, 0.2 ml of trifluoromethanesulfonic acid and 4.0 ml of trifluoroacetic anhydride were sequentially added. Stirring was continued at 50 ° C. for 120 hours while blowing oxygen gas. After completion of the reaction, the reaction mixture was poured into 200 ml of methanol containing 1 ml of concentrated hydrochloric acid. The precipitate was collected by filtration and dried under reduced pressure at 50 ° C. for 5 hours to give 0.59 g of poly (2-methoxy-5- (2- (2-methoxyethoxy) ethoxy) -1,4-phenylene) as a brown powder. As obtained. IR spectrum data is shown in FIG.
[0026]
Example 2
Example 1 was repeated using 2.70 g of ME3PM instead of ME2PM, resulting in 0.18 g of poly (2-methoxy-5- (2- (2- (2-methoxyethoxy) ethoxy) ethoxy) -1, 4-phenylene) was obtained as a brown powder. IR spectrum data is shown in FIG.
[0027]
Example 3
1.27 g of BE2P was used in place of ME2PM, 133 mg of VO (acac) 2 , 0.1 ml of trifluoromethanesulfonic acid, and 1.5 ml of trifluoroacetic anhydride, and the same oxidative polymerization as in Example 1 at 40 ° C. As a result of time, 0.42 g of poly (2,5-bis (2-ethoxyethoxy) -1,4-phenylene) was obtained as a brown powder.
[0028]
【The invention's effect】
According to the present invention, a conductive polymer, particularly poly (phenylene) having an ethylene oxide chain useful as a display material or an electrode material for battery applications, and its easy production in a short step under mild conditions using an inexpensive raw material A method is provided.
[Brief description of the drawings]
FIG. 1 is IR spectrum data of the polymers obtained in Example 1 and Example 2. FIG.
Claims (7)
Priority Applications (1)
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| JP10161897A JP3738525B2 (en) | 1997-04-18 | 1997-04-18 | Poly (phenylene) having ethylene oxide chain in side chain and method for producing the same |
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| JP10161897A JP3738525B2 (en) | 1997-04-18 | 1997-04-18 | Poly (phenylene) having ethylene oxide chain in side chain and method for producing the same |
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| JPH10292034A JPH10292034A (en) | 1998-11-04 |
| JP3738525B2 true JP3738525B2 (en) | 2006-01-25 |
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| JP4797464B2 (en) * | 2004-06-28 | 2011-10-19 | 住友化学株式会社 | Vanadyl dinuclear complex |
| CA2572170A1 (en) | 2004-06-28 | 2006-01-05 | Sumitomo Chemical Company, Limited | Method for producing aromatic compound polymer |
| JP4595708B2 (en) * | 2005-06-27 | 2010-12-08 | 住友化学株式会社 | Process for producing aromatic polymer |
| JP5471861B2 (en) * | 2010-06-11 | 2014-04-16 | 住友化学株式会社 | Process for producing aromatic polymer |
| JP5914023B2 (en) * | 2012-02-16 | 2016-05-11 | 住友化学株式会社 | Film-forming composition, film-forming method using the same, laminated structure, and organic electronic device |
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