JPH06256520A - Electrically conductive polymer and its production - Google Patents
Electrically conductive polymer and its productionInfo
- Publication number
- JPH06256520A JPH06256520A JP7093493A JP7093493A JPH06256520A JP H06256520 A JPH06256520 A JP H06256520A JP 7093493 A JP7093493 A JP 7093493A JP 7093493 A JP7093493 A JP 7093493A JP H06256520 A JPH06256520 A JP H06256520A
- Authority
- JP
- Japan
- Prior art keywords
- polysiloxane
- ferric chloride
- side chain
- doping
- carbazole group
- 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.)
- Granted
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ポリシロキサンからな
る導電性重合体及びその製造方法に関し、特にバッテリ
ー電極、太陽電池、電磁シールド用筺体などの用途に好
適な導電性重合体及びその製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a conductive polymer made of polysiloxane and a method for producing the same, and more particularly, a conductive polymer suitable for use in battery electrodes, solar cells, housings for electromagnetic shields, and a method for producing the same. Regarding
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】近年、
ポリアセチレンに電子受容性物質又は電子供与性物質を
ドーピングすると電荷移動形成反応が起こり、電子伝導
に基づく高い電気伝導性が発現することが見い出だされ
たことから、ポリアセチレン、ポリフェニレン、ポリピ
ロール、ポリアニリン及びポリチオフェン等の導電性有
機高分子化合物が高導電性フィルムなどを形成する材料
として注目されている。2. Description of the Related Art In recent years,
It was found that when polyacetylene is doped with an electron-accepting substance or an electron-donating substance, a charge transfer forming reaction occurs, and high electrical conductivity based on electron conduction is expressed, so that polyacetylene, polyphenylene, polypyrrole, polyaniline In addition, conductive organic polymer compounds such as polythiophene have attracted attention as materials for forming highly conductive films.
【０００３】しかしながら、これら有機高分子化合物
は、不溶不融であるため賦形性に乏しかったり、気相重
合法や電解重合法でフィルムを形成する場合、得られる
フィルムの形状が反応容器や電極の形状によって制約さ
れたり、電子受容性物質又は電子供与性物質をドーピン
グする際に著しい劣化を伴ったりするなどの問題があ
り、実用上の障害になっている。However, since these organic polymer compounds are insoluble and infusible, they have poor shapeability. When a film is formed by a gas phase polymerization method or an electrolytic polymerization method, the shape of the obtained film is a reaction vessel or an electrode. However, there is a problem in that it is restricted by the shape of the above, and it is accompanied by remarkable deterioration when doping an electron accepting substance or an electron donating substance, which is a practical obstacle.
【０００４】一方、ポリシロキサンは、高い耐熱性及び
柔軟性、良好な薄膜形成性を有することから非常に興味
深いポリマーであるが、高導電性を有するものはほとん
ど知られていない。わずかにベルンドらによってカルバ
ゾール基を側鎖に有するポリシロキサンを電気化学的に
酸化することにより導電率の最高値が８．３×１０-4Ｓ
／ｃｍの高分子化合物が提案されている（特開昭６３−
１９９７３６号公報）が、この高分子化合物は導電性が
十分ではなく、また、高価な電解質と電気化学的酸化と
いう煩雑な工程を必要とするという問題がある。なお、
カルバゾール基を側鎖に有するポリシロキサンは「Ｐ．
Ｓｔｒｏｈｒｉｅｇｌ、Ｍａｃｒｏｍｏｌ．Ｃｈｅ
ｍ．，Ｒａｐｉｄ Ｃｏｍｍｕｎ．，７，７７１（１９
８６）」に記載されている。On the other hand, polysiloxane is a very interesting polymer because it has high heat resistance, flexibility and good thin film forming property, but few have high conductivity. By electrochemically oxidizing a polysiloxane having a carbazole group in the side chain slightly by Bernd et al., The maximum value of conductivity was 8.3 × 10 −4 S
/ Cm polymer compounds have been proposed (Japanese Patent Laid-Open No. 63-
However, this polymer compound has a problem that the conductivity is not sufficient and a complicated process of expensive electrolyte and electrochemical oxidation is required. In addition,
The polysiloxane having a carbazole group in its side chain is described in "P.
Strohriegl, Macromol. Che
m. , Rapid Commun. , 7, 771 (19
86) ”.
【０００５】本発明は上記事情に鑑みなされたもので、
カルバゾール基を側鎖に有するポリシロキサンからなる
高導電性で賦形性に優れた導電性重合体及びその製造方
法を提供することを目的とする。The present invention has been made in view of the above circumstances.
It is an object of the present invention to provide a conductive polymer having a carbazole group as a side chain and having high conductivity and excellent shapeability, and a method for producing the same.
【０００６】[0006]
【課題を解決するための手段及び作用】本発明者は上記
目的を達成するため鋭意検討を行った結果、カルバゾー
ル基を側鎖に有するポリシロキサンを塩化第二鉄の蒸気
雰囲気下にさらすという乾式法、具体的には例えば塩化
第二鉄を減圧下で加温して蒸気化し、この塩化第二鉄蒸
気でカルバゾール基を側鎖に有するポリシロキサンをさ
らすことにより、簡単にドーピングし得、高導電性で賦
形性に優れた導電性重合体が得られることを知見した。
即ち、カルバゾール基を側鎖に有するポリシロキサンは
溶剤に可溶であるため、所望の形状のフィルムや塗膜の
形態とすることができ、このように所望の形状のフィル
ム、塗膜とした状態でドーピングし得ると共に、ドーピ
ングに用いる塩化第二鉄は毒性が少なくかつ安価であ
り、カルバゾール基を側鎖に有するポリシロキサンに対
する導電性付与が簡単で、かつ高い導電性を付与するこ
とができること、しかもドーピング後もカルバゾール基
を側鎖に有するポリシロキサンが脆化することもなく可
撓性を維持し得ることを見い出した。Means and Actions for Solving the Problems As a result of intensive studies for achieving the above object, the present inventor has found that a dry method of exposing a polysiloxane having a carbazole group in a side chain to a ferric chloride vapor atmosphere Method, specifically, for example, ferric chloride is heated under reduced pressure to be vaporized, and the polysiloxane having a carbazole group in a side chain is exposed to the ferric chloride vapor to easily dope, It was found that a conductive polymer having conductivity and excellent shapeability can be obtained.
That is, since the polysiloxane having a carbazole group in the side chain is soluble in a solvent, it can be formed into a film or coating film having a desired shape. Ferric chloride used for doping has low toxicity and is inexpensive, and it is possible to easily impart conductivity to polysiloxane having a carbazole group in its side chain, and to impart high conductivity. Moreover, it was found that the polysiloxane having a carbazole group in its side chain can maintain its flexibility even after doping without being embrittled.
【０００７】この場合、カルバゾール基を側鎖に有する
ポリシロキサンに塩化第二鉄をドーピングする方法とし
て、従来、（１）塩化第二鉄を不活性溶媒中に溶解した
溶液中にケイ素含有高分子物質を浸漬する湿式ドーピン
グ法、（２）塩化第二鉄を溶解した溶液中にケイ素含有
高分子物質を溶解し、この溶解液から成膜することによ
りフィルム又は塗膜に賦形すると同時にドーピングする
同時ドーピング法が採用されているが、これらいずれの
ドーピング法も、塩化第二鉄をドーピングすることによ
ってカルバゾール基を側鎖に有するポリシロキサンの劣
化が起こり、このためカルバゾール基を側鎖に有するポ
リシロキサンのゲル化や分解が起こり、また高い導電率
を達成することはできない。しかし、本発明の方法は、
このような不都合がなく、しかも高導電率に容易にドー
ピングし得るものである。In this case, as a method for doping ferric chloride into a polysiloxane having a carbazole group in its side chain, (1) a silicon-containing polymer in a solution prepared by dissolving ferric chloride in an inert solvent is conventionally used. Wet doping method of immersing a substance, (2) Dissolving a silicon-containing polymer in a solution in which ferric chloride is dissolved, and forming a film from this solution to form a film or coating film and simultaneously perform doping The co-doping method is adopted, but in both of these doping methods, the polysiloxane having a carbazole group in the side chain is deteriorated by doping with ferric chloride, and therefore, the polysiloxane having a carbazole group in the side chain is caused. Gelation and decomposition of the siloxane occur and high conductivity cannot be achieved. However, the method of the present invention is
It is possible to dope with high conductivity without such inconvenience.
【０００８】更に、上記方法により得られた導電性重合
体は、賦形性に優れる高導電性フィルム又は塗膜を容易
に得ることができ、バッテリー電極、太陽電池、電磁シ
ールド用筺体などを形成するための素材として有用であ
り、電気、電子、通信分野などの分野で広範囲に亘って
使用し得ることを知見し、本発明をなすに至った。Furthermore, the electroconductive polymer obtained by the above method can easily obtain a highly electroconductive film or coating film having excellent shapeability, and forms battery electrodes, solar cells, casings for electromagnetic shields, etc. The present invention has been completed on the basis of the finding that it is useful as a material for achieving the above and can be used in a wide range of fields such as electric, electronic and communication fields.
【０００９】従って、本発明は、塩化第二鉄が気相ドー
ピングされたカルバゾール基を側鎖に有するポリシロキ
サンからなる導電性重合体、及び、カルバゾール基を側
鎖に有するポリシロキサンに塩化第二鉄を気相ドーピン
グすることを特徴とする導電性重合体の製造方法を提供
する。Therefore, the present invention provides a conductive polymer comprising a polysiloxane having a carbazole group in the side chain, which is doped with ferric chloride in a gas phase, and a polysiloxane having a carbazole group in the side chain. Provided is a method for producing a conductive polymer, which is characterized by performing vapor phase doping of iron.
【００１０】以下、本発明を更に詳しく説明すると、本
発明の導電性重合体は、カルバゾール基を側鎖に有する
ポリシロキサンに塩化第二鉄を気相ドーピングしてなる
ものである。The present invention will be described in more detail below. The conductive polymer of the present invention is obtained by vapor-phase doping ferric chloride into a polysiloxane having a carbazole group in its side chain.
【００１１】ここで、上記カルバゾール基を側鎖に有す
るポリシロキサンとしては下記一般式で示されるものが
挙げられる。Examples of the polysiloxane having a carbazole group in its side chain include those represented by the following general formula.
【００１２】[0012]
【化１】 [Chemical 1]
【００１３】上記式においてＲ1 は下記式で表わされる
ものを示し、Ｒ2 はＲ1 又は炭素数１〜１８の１価有機
基、例えばメチル，エチル，プロピル，ブチル等のアル
キル基、フェニル，トリル等のアリール基を示し、Ｒ3
はＲ2 又は炭素数０〜１０の１価有機基、例えばヒドロ
オキシ基，メトキシ，エトキシのようなアルコキシ基、
メチル，エチルのようなアルキル基、ビニルのようなア
ルケニル基、フェニル，トリルのようなアリール基を示
し、ｍは１以上の整数、より好ましくは４〜４０００、
ｋは１〜３の整数である。In the above equation, R1 Is expressed by the following formula
Show the thing, R2 Is R1 Or monovalent organic having 1 to 18 carbon atoms
Groups such as methyl, ethyl, propyl, butyl, etc.
Represents an aryl group such as a kill group, phenyl or tolyl, and R3
Is R2 Or a monovalent organic group having 0 to 10 carbon atoms, for example, hydro
Oxy group, methoxy, alkoxy group such as ethoxy,
Alkyl groups such as methyl and ethyl, and vinyl groups
Shows aryl groups such as lukenyl, phenyl and tolyl.
, M is an integer of 1 or more, more preferably 4 to 4000,
k is an integer of 1 to 3.
【００１４】[0014]
【化２】 [Chemical 2]
【００１５】なお、カルバゾール基を側鎖に有するポリ
シロキサンは、例えばＮ−アルケニル基を含有するカル
バゾール誘導体とポリ（ヒドロシロキサン）とのヒドロ
シリル化反応により容易に合成することができる。特
に、カルバゾールプロピル基を側鎖に有するポリシロキ
サンは、Ｎ−アリルカルバゾールとトリメチルシロキシ
基末端ヒドロメチルポリシロキサンを塩化白金酸触媒の
存在下に反応させることにより容易に得ることができ
る。The polysiloxane having a carbazole group in its side chain can be easily synthesized, for example, by a hydrosilylation reaction between a carbazole derivative containing an N-alkenyl group and poly (hydrosiloxane). In particular, a polysiloxane having a carbazolepropyl group in its side chain can be easily obtained by reacting N-allylcarbazole with trimethylsiloxy group-terminated hydromethylpolysiloxane in the presence of a chloroplatinic acid catalyst.
【００１６】なお、これらカルバゾール基を側鎖に有す
るポリシロキサンの分子量は特に制限されるものではな
いが、通常１，０００〜１，０００，０００のものが用
いられる。The molecular weight of these polysiloxanes having a carbazole group in the side chain is not particularly limited, but those having a molecular weight of 1,000 to 1,000,000 are usually used.
【００１７】本発明の導電性重合体を得るには、塩化第
二鉄を常圧又は減圧下に加温して塩化第二鉄を蒸気化
し、この塩化第二鉄の蒸気中で上記カルバゾール基を側
鎖に有するポリシロキサンを気相ドーピングするもので
あり、気相ドーピングの進行と共にカルバゾール基を側
鎖に有するポリシロキサン皮膜の導電率が速やかに上昇
していき、最終的に導電率はある一定値に落ち着き、ド
ーピングが終了する。To obtain the conductive polymer of the present invention, ferric chloride is heated under normal pressure or reduced pressure to vaporize ferric chloride, and the above carbazole group is vaporized in the vapor of ferric chloride. In the vapor-phase doping of polysiloxane having a side chain, the conductivity of the polysiloxane film having a carbazole group in the side chain increases rapidly with the progress of the vapor-phase doping, and the conductivity finally exists. Doping is complete when the temperature reaches a certain level.
【００１８】この場合、ドーパント（塩化第二鉄）雰囲
気の温度と容器内の圧力を制御することによりドーピン
グ速度を制御することができる。具体的には、圧力０．
００１〜７６０ｍｍＨｇ、温度５０〜３００℃の範囲、
特に圧力０．１〜１０ｍｍＨｇ、温度５０〜２００℃の
範囲でドーピングを行うことがポリマーの導電率を効果
的に上げることができる点から好ましい。この圧力が
０．００１ｍｍＨｇ未満では、その圧力に達するまでに
長時間がかかるため経済的でなく、また、塩化第二鉄の
常圧での沸点が３１９℃であるため、圧力が７６０ｍｍ
Ｈｇを越えるとドーピング速度が非常に遅くなってしま
う。また、温度が５０℃未満ではドーピング速度が遅く
なり、また３００℃を越えるとドーピング時にカルバゾ
ール基を側鎖に有するポリシロキサンの劣化を招く場合
がある。In this case, the doping rate can be controlled by controlling the temperature of the dopant (ferric chloride) atmosphere and the pressure in the container. Specifically, the pressure is 0.
001 to 760 mmHg, temperature range of 50 to 300 ° C.,
In particular, it is preferable to perform the doping at a pressure of 0.1 to 10 mmHg and a temperature of 50 to 200 ° C. from the viewpoint of effectively increasing the conductivity of the polymer. If the pressure is less than 0.001 mmHg, it takes a long time to reach the pressure, which is not economical, and since the boiling point of ferric chloride at atmospheric pressure is 319 ° C, the pressure is 760 mm.
If it exceeds Hg, the doping rate becomes very slow. Further, if the temperature is lower than 50 ° C., the doping rate becomes slow, and if it exceeds 300 ° C., the polysiloxane having a carbazole group in the side chain may be deteriorated at the time of doping.
【００１９】上記ドーピング法を用いることにより、引
火性の溶媒を使用することなく毒性の少ない塩化第二鉄
をドーパントとして非常に簡単な操作で高導電率の導電
性重合体を製造することができる。By using the above-mentioned doping method, a highly conductive conductive polymer can be produced by a very simple operation using ferric chloride having low toxicity as a dopant without using a flammable solvent. .
【００２０】[0020]
【実施例】以下、実施例と比較例を示し、本発明を具体
的に説明するが、本発明は下記の実施例に制限されるも
のではない。なお、実施例の説明に先立ち、実施例で用
いるカルバゾールプロピル基を側鎖に有するポリシロキ
サンの製造方法について説明する。EXAMPLES The present invention will be specifically described below by showing Examples and Comparative Examples, but the present invention is not limited to the following Examples. In addition, prior to the description of the examples, a method for producing a polysiloxane having a carbazolepropyl group in a side chain used in the examples will be described.
【００２１】[0021]
【化３】 [Chemical 3]
【００２２】［合成例］Ｎ−アリルカルバゾール３２ｇ
をトルエンに溶解し、これに触媒量の塩化白金酸を添加
し、７０〜８０℃に保った。次いで、これを撹拌しなが
らトリメチルシロキシ末端ヒドロメチルポリシロキサン
をゆっくり滴下した。原料が消失するまで４時間撹拌し
て反応を完結させ、放冷後、活性炭処理し、濃縮し、カ
ルバゾールプロピル基を側鎖に有するポリシロキサン
（化合物Ｉ）を得た。[Synthesis Example] N-allylcarbazole 32 g
Was dissolved in toluene, a catalytic amount of chloroplatinic acid was added thereto, and the temperature was maintained at 70 to 80 ° C. Then, trimethylsiloxy-terminated hydromethylpolysiloxane was slowly added dropwise while stirring this. The reaction was completed by stirring for 4 hours until the raw materials disappeared, allowed to cool, treated with activated carbon, and concentrated to obtain a polysiloxane (compound I) having a carbazolepropyl group in its side chain.
【００２３】［実施例］カルバゾール基を側鎖に有する
ポリシロキサン（合成例で製造した化合物Ｉ）をテトラ
ヒドロフラン（ＴＨＦ）に溶解し、１０％ポリマー溶液
を得た。一方、ガラス板上に白金蒸着により４端子部を
形成して電極とし、このガラス板上に上記ポリマー溶液
をスピンコートし、圧力２ｍｍＨｇ、温度５０℃で乾燥
させ、厚さ１μｍの薄膜を製造し、導電率測定用サンプ
ルを得た。[Example] Polysiloxane having a carbazole group in the side chain (Compound I prepared in Synthesis Example) was dissolved in tetrahydrofuran (THF) to obtain a 10% polymer solution. On the other hand, 4 terminals were formed on a glass plate by vapor deposition of platinum to form electrodes, and the polymer solution was spin-coated on the glass plate and dried at a pressure of 2 mmHg and a temperature of 50 ° C. to produce a thin film having a thickness of 1 μm. A sample for conductivity measurement was obtained.
【００２４】次に、乾燥させた褐色ガラス瓶容器の底部
に固体の塩化第二鉄を入れ、上記サンプルをこのガラス
瓶の内部に取り付け、密閉した。このガラス瓶を真空ポ
ンプに接続し、４ｍｍＨｇまで減圧にした状態でガラス
瓶底部の塩化第二鉄をマントルヒーターで加熱した。こ
の加熱によってケイ素含有高分子薄膜は透明から黒茶色
に変化していき、同時に導電率が速やかに上昇して行っ
た。最終的には導電率は８×１０-2Ｓ／ｃｍに落ち着
き、このとき導電率測定用サンプルの温度は１５０℃に
まで達していた。ここで真空ポンプを停止し、加熱を止
め、２５℃まで放冷し、導電率を測定したところ、２×
１０-3Ｓ／ｃｍであった。Next, solid ferric chloride was put in the bottom of the dried brown glass bottle container, and the above sample was attached inside the glass bottle and sealed. The glass bottle was connected to a vacuum pump, and the ferric chloride at the bottom of the glass bottle was heated with a mantle heater while the pressure was reduced to 4 mmHg. This heating caused the silicon-containing polymer thin film to change from transparent to black brown, and at the same time, the conductivity rapidly increased. Finally, the conductivity settled down to 8 × 10 -2 S / cm, at which time the temperature of the sample for conductivity measurement reached 150 ° C. Here, the vacuum pump was stopped, heating was stopped, the temperature was allowed to cool to 25 ° C, and the conductivity was measured.
It was 10 −3 S / cm.
【００２５】なお、導電率の測定は、上記ガラス板上の
皮膜を塩化第二鉄蒸気と接触させながら直流抵抗の経時
変化を追跡し、この抵抗値が安定値をとった後、皮膜の
温度が２５℃に下がるまで放冷し、そのときの抵抗値か
ら導電率を求めた。The conductivity was measured by keeping track of the time course of the direct current resistance while keeping the film on the glass plate in contact with ferric chloride vapor, and after the resistance value reached a stable value, the temperature of the film was changed. Was allowed to cool to 25 ° C., and the conductivity was determined from the resistance value at that time.
【００２６】［比較例］カルバゾールプロピル基を側鎖
に有するポリシロキサン（化合物Ｉ）をＴＨＦに溶解
し、１０％のＴＨＦ溶液とした。これに塩化第二鉄の１
０％ＴＨＦ溶液を化合物Ｉに対して５０重量％となるよ
うに混合し、放置した。その結果、混合してから約１時
間経過後、この混合物はゲル化してしまった。Comparative Example A polysiloxane having a carbazolepropyl group in its side chain (Compound I) was dissolved in THF to prepare a 10% THF solution. 1 of ferric chloride
A 0% THF solution was mixed with the compound I in an amount of 50% by weight, and the mixture was allowed to stand. As a result, this mixture gelled about 1 hour after mixing.
【００２７】一方、ガラス板上に４端子部を白金蒸着に
より形成して電極とし、このガラス板上に、塩化第二鉄
の１０％ＴＨＦ溶液と上記ケイ素含有高分子化合物の１
０％ＴＨＦとを混合後、直ちにスピンコートし、圧力２
ｍｍＨｇ、温度５０℃で乾燥させ、厚さ０．７μｍの薄
膜を作製し、導電率測定用サンプルとし、導電率を測定
したところ、１×１０-10Ｓ／ｃｍであった。On the other hand, four terminals were formed on the glass plate by platinum vapor deposition to form electrodes, and a 10% THF solution of ferric chloride and 1 of the above-mentioned silicon-containing polymer compound were formed on this glass plate.
Immediately spin-coat after mixing with 0% THF and apply pressure 2
The film was dried at mmHg and a temperature of 50 ° C. to form a thin film having a thickness of 0.7 μm, which was used as a sample for measuring conductivity, and the conductivity was measured and found to be 1 × 10 −10 S / cm.
【００２８】[0028]
【発明の効果】本発明によれば、賦形性に優れる高導電
性のフィルム又は塗膜を容易に得ることができ、これら
はバッテリー電極、太陽電池、電磁シールド用筺体など
を形成するための素材として有用であり、電気、電子、
通信分野などの分野で広範囲に亘って使用し得るもので
ある。According to the present invention, it is possible to easily obtain a highly conductive film or coating film having excellent shapeability, which can be used for forming battery electrodes, solar cells, casings for electromagnetic shields, and the like. It is useful as a material, electricity, electronic,
It can be used in a wide range of fields such as the communication field.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 田部井 栄一 神奈川県川崎市高津区坂戸３丁目２番１号 信越化学工業株式会社コーポレートリサ ーチセンター内 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Eiichi Tabei 3-2-1 Sakado, Takatsu-ku, Kawasaki City, Kanagawa Shin-Etsu Chemical Co., Ltd. Corporate Research Center
Claims (2)
バゾール基を側鎖に有するポリシロキサンからなること
を特徴とする導電性重合体。1. A conductive polymer in which ferric chloride comprises a polysiloxane having a carbazole group as a side chain, which is vapor-phase doped.
に塩化第二鉄を気相ドーピングすることを特徴とする導
電性重合体の製造方法。2. A method for producing a conductive polymer, which comprises subjecting a polysiloxane having a carbazole group to gas phase doping with ferric chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5070934A JP3028698B2 (en) | 1993-03-05 | 1993-03-05 | Conductive polymer and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5070934A JP3028698B2 (en) | 1993-03-05 | 1993-03-05 | Conductive polymer and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06256520A true JPH06256520A (en) | 1994-09-13 |
| JP3028698B2 JP3028698B2 (en) | 2000-04-04 |
Family
ID=13445842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5070934A Expired - Fee Related JP3028698B2 (en) | 1993-03-05 | 1993-03-05 | Conductive polymer and method for producing the same |
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| Country | Link |
|---|---|
| JP (1) | JP3028698B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6009309A (en) * | 1993-05-04 | 1999-12-28 | Motorola, Inc. | Method of operation a combination radiotelephone and paging device and method of operation |
| WO2005019308A1 (en) * | 2003-08-20 | 2005-03-03 | Dow Corning Corporation | Carbazolyl-functional linear polysiloxanes, silicone composition, and organic light-emitting diode |
| WO2005019309A1 (en) * | 2003-08-20 | 2005-03-03 | Dow Corning Corporation | Carbazolyl-functional polysiloxane resins, silicone composition, and organic light-emitting diode |
| WO2005035632A1 (en) * | 2003-09-11 | 2005-04-21 | Dow Corning Corporation | Carbazolyl-functional hyperbranched polysiloxanes, silicone composition, and organic light-emmitting diode |
| WO2009019931A1 (en) * | 2007-08-07 | 2009-02-12 | Sony Chemical & Information Device Corporation | Sealing material for optical component and light-emitting device |
-
1993
- 1993-03-05 JP JP5070934A patent/JP3028698B2/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6009309A (en) * | 1993-05-04 | 1999-12-28 | Motorola, Inc. | Method of operation a combination radiotelephone and paging device and method of operation |
| WO2005019308A1 (en) * | 2003-08-20 | 2005-03-03 | Dow Corning Corporation | Carbazolyl-functional linear polysiloxanes, silicone composition, and organic light-emitting diode |
| WO2005019309A1 (en) * | 2003-08-20 | 2005-03-03 | Dow Corning Corporation | Carbazolyl-functional polysiloxane resins, silicone composition, and organic light-emitting diode |
| WO2005035632A1 (en) * | 2003-09-11 | 2005-04-21 | Dow Corning Corporation | Carbazolyl-functional hyperbranched polysiloxanes, silicone composition, and organic light-emmitting diode |
| WO2009019931A1 (en) * | 2007-08-07 | 2009-02-12 | Sony Chemical & Information Device Corporation | Sealing material for optical component and light-emitting device |
| US8076437B2 (en) | 2007-08-07 | 2011-12-13 | Sony Chemical & Information Device Corporation | Encapsulant material for optical component and light-emitting device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3028698B2 (en) | 2000-04-04 |
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