JPH0520449B2 - - Google Patents
Info
- Publication number
- JPH0520449B2 JPH0520449B2 JP57070054A JP7005482A JPH0520449B2 JP H0520449 B2 JPH0520449 B2 JP H0520449B2 JP 57070054 A JP57070054 A JP 57070054A JP 7005482 A JP7005482 A JP 7005482A JP H0520449 B2 JPH0520449 B2 JP H0520449B2
- Authority
- JP
- Japan
- Prior art keywords
- ions
- polymer composition
- conductive
- dopant
- group element
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 15
- 239000002019 doping agent Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 239000011669 selenium Substances 0.000 claims description 3
- 229910052714 tellurium Inorganic materials 0.000 claims description 3
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003346 selenoethers Chemical class 0.000 claims description 2
- 229940125782 compound 2 Drugs 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- -1 sulfur tetrafluoroborate Chemical compound 0.000 description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
- ULUNQYODBKLBOE-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)-1h-pyrrole Chemical compound C1=CNC(C=2NC=CC=2)=C1 ULUNQYODBKLBOE-UHFFFAOYSA-N 0.000 description 1
- PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical compound C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 description 1
- BNRREYILJZPKKN-UHFFFAOYSA-N 2-selenophen-2-yl-1h-pyrrole Chemical compound C1=CNC(C=2[se]C=CC=2)=C1 BNRREYILJZPKKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- ORQWTLCYLDRDHK-UHFFFAOYSA-N phenylselanylbenzene Chemical compound C=1C=CC=CC=1[Se]C1=CC=CC=C1 ORQWTLCYLDRDHK-UHFFFAOYSA-N 0.000 description 1
- XTCBHFKSTRGVMZ-UHFFFAOYSA-N phenyltellanylbenzene Chemical compound C=1C=CC=CC=1[Te]C1=CC=CC=C1 XTCBHFKSTRGVMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Conductive Materials (AREA)
Description
本発明は、導電性ないし半導性重合体組成物の
製造方法に関する。
従来、たとえばK.Keiji Kanazawa et.al.、J.
Chem.Soc.Chem.Comm.、854（1979）などにたと
えば、ホウ弗化テトラエチルアンモニウムなどの
支持電解質の存在下でピロールを電解酸化して重
合体組成物を製造する方法が挙げられている。こ
れらの組成物は大きな導電率をもち、たとえば、
導電体などとして有用である。しかし、こうして
得た組成物は、一般に多孔質でもろく、実際的な
使用には難点をもつている。また、電解酸化の手
法を用いて種々の化合物から導電性または半導電
性重合体組成物が得られることも知られていなか
つた。
これらの事情を考慮して、本発明は、後述の化
合物を電解酸化して、導電性または半導電性重合
体組成物を製造する簡便で効率のよい方法を提供
するものである。
本発明の方法は、電解酸化物質（本発明による
組成物を得るために電解酸化される物質をこう呼
ぶ）をドーパントとの共存下で電解酸化すること
を特徴とする。電解酸化物質とドーパントが共に
固体の場合は、これらを適当な溶媒に溶解させて
電解酸化する。共に液体かどちらか一方が液体の
場合は、両者の混合または分散によつて電解酸化
し得る。
本発明で用いる電解酸化物質は、次のような化
合物である。
(a)ベンゼンまたはその誘導体、(b)酸素族元素を
１つ含む複素五員環化合物、(c)ベンゼン環と、酸
素族元素もしくは窒素族元素を１つ含む複素五員
環とよりなる群から選んだ複数の環が直接または
エーテル、スルフイド、セレニド、テルリド結合
のうちどれかの結合を介して直鎖状に結合した化
合物
具体例としてはたとえば、次のような化合物が
挙げられる：
フエノール、チオフエノール、フラン、チオフ
エン、セレノフエン、テルロフエン
The present invention relates to a method for producing an electrically conductive or semiconductive polymer composition. Previously, for example, K. Keiji Kanazawa et.al., J.
Chem.Soc.Chem.Comm., 854 (1979) and the like disclose a method of producing a polymer composition by electrolytically oxidizing pyrrole in the presence of a supporting electrolyte such as tetraethylammonium borofluoride. These compositions have large electrical conductivities, e.g.
It is useful as a conductor. However, the compositions thus obtained are generally porous and brittle, making them difficult to use in practice. Furthermore, it was not known that conductive or semiconductive polymer compositions could be obtained from various compounds using electrolytic oxidation techniques. In consideration of these circumstances, the present invention provides a simple and efficient method for producing a conductive or semiconductive polymer composition by electrolytically oxidizing the compound described below. The method of the present invention is characterized in that an electrolytically oxidized substance (the substance to be electrolytically oxidized to obtain the composition according to the invention is called this) is electrolytically oxidized in the presence of a dopant. When the electrolytically oxidized substance and the dopant are both solid, they are dissolved in a suitable solvent and electrolytically oxidized. When both or one of the two is liquid, electrolytic oxidation can be carried out by mixing or dispersing the two. The electrolytically oxidized substance used in the present invention is the following compound. (a) benzene or its derivatives; (b) a five-membered heterocyclic compound containing one oxygen group element; (c) a group consisting of a benzene ring and a five-membered heterocyclic ring containing one oxygen group element or one nitrogen group element. A compound in which multiple rings selected from the following are linked directly or in a linear chain through any one of ether, sulfide, selenide, and telluride bonds. Specific examples include the following compounds: Phenol, Thiophenol, furan, thiophene, selenophene, tellurofene
【式】ビフエニル、Ｐ−タ−フエニ
ル、Ｏ−タ−フエニル、Ｐ−クオータフエニル、
２−ヒドロキシビフエニル、ジフエニルエーテ
ル、ジフエニルスルフイド、ジフエニルセレニ
ド、ジフエニルテルリド、２−（α−チエニル）
チオフエン、２−（α−チエニル）フラン、２−
（２−ピロリル）ピロール、２−（２−ピロピル）
チオフエン、２−フエニルチオフエン、α−チエ
ニル＝フエニル＝エーテル、β−フリル＝α−チ
エニル＝セレニド、２−（２−ピロリル）セレノ
フエン、２−（２−セレニエニル）テルロフエン。
ドーパントには、有機四級アンモニウム塩、無
機塩、プロトン酸、エステルなどの種々の化合物
があり、例えばホウ弗化テトラエチルアンモニウ
ム、過塩素酸テトラ−ｎ−ブチルアンモニウム、
臭化テトラメチルアンモニウム、過塩素酸リチウ
ム、硝酸バリウム、硫酸アンモニウム、硫酸など
が挙げられる。
本発明は一見して、前述のKanazawaらの方法
と類似しているようにみえるが、とくに緻密で平
滑な重合体組成物を与える点で従来の方法とは全
くちがつた効果をもつている。これは用いた電解
酸化物質がピロールに比べて電解酸化されやすい
ために脱水素による重合反応が起こりやすく、重
合度が高まることによると解釈しうる。なかで
も、電解酸化物質が環上にイオウ、セレン、テル
ルのうちどれかをもつ複素五員環を含むときは、
本発明の方法できわめて緻密で強じんなフイルム
状の重合体組成物を得ることも容易である。これ
は、イオウ、セレン、テルルの電気陰性度が低
く、とくに電解酸化されやすいためと解される。
さらに、ドーパントがたとえば、テトラフルオロ
ボレートイオウなどのホウハロゲン化イオン、パ
ークロレートイオンなどのパーハロゲネートイオ
ンや硫酸イオンなどを含む化合物から選ばれたと
きも同様の効果を生む。
次に実施例を挙げて本発明をさらに詳しく説明
する。
種々の電解酸化物質をドーパントとともに各種
の溶媒に溶解または分散させ、さまざまな条件で
電解酸化物質を酸化し、白金陽極上に導電性また
は半導電性重合体組成物を得た。これをメタノー
ルで洗浄した後に一昼夜真空乾燥して試料とし
た。塊性試料の場合は、さらに粉末状に粉砕した
後、１mm厚のデイスク状に加圧成形し、両面に銀
塗料を塗布して導電率測定用試料とした。フイル
ム状の試料の場合は、幅15mm、長さ110mmの試料
を４枚つくり、２枚は銀塗料を塗布して四端子法
による導電率測定用試料とし、他の２枚はJIS
P8115−1960の耐折強さを試験用試料とした。
次表に、電解酸化物質、ドーパントの種類と
量、溶媒の種類、電解酸化の条件および導電率の
値とを示す。なお、電解酸化物質の初期の仕込み
量は１ｇ、溶媒量は100mlに統一し、ドーパント
の量はカツコ内に初期の仕込量をｇ単位で表す。
また、表の導電率の値は２試料の平均値である。
比較例としてドーピング時期を変更するため、
まずチオフエンを電解酸化した後ドーパントをド
ーピングしたが、緻密で平滑なフイルム状の重合
体組成物は得られなかつた。[Formula] biphenyl, P-terphenyl, O-terphenyl, P-quarterphenyl,
2-hydroxybiphenyl, diphenyl ether, diphenyl sulfide, diphenyl selenide, diphenyl telluride, 2-(α-thienyl)
Thiophene, 2-(α-thienyl)furan, 2-
(2-pyrrolyl)pyrrole, 2-(2-pyropyl)
Thiophene, 2-phenylthiophene, α-thienyl phenyl ether, β-furyl α-thienyl selenide, 2-(2-pyrrolyl)selenophene, 2-(2-selenienyl)tellophene. Dopants include various compounds such as organic quaternary ammonium salts, inorganic salts, protic acids, and esters, such as tetraethylammonium borofluoride, tetra-n-butylammonium perchlorate,
Examples include tetramethylammonium bromide, lithium perchlorate, barium nitrate, ammonium sulfate, and sulfuric acid. At first glance, the present invention appears to be similar to the above-mentioned method of Kanazawa et al., but it has a completely different effect from conventional methods, especially in providing a dense and smooth polymer composition. . This can be interpreted to be because the electrolytically oxidized substance used is more easily electrolytically oxidized than pyrrole, so that a polymerization reaction due to dehydrogenation occurs more easily, increasing the degree of polymerization. In particular, when the electrolytically oxidized substance contains a five-membered hetero ring having one of sulfur, selenium, and tellurium on the ring,
It is also easy to obtain extremely dense and strong film-like polymer compositions by the method of the present invention. This is understood to be because sulfur, selenium, and tellurium have low electronegativity and are particularly susceptible to electrolytic oxidation.
Furthermore, a similar effect is produced when the dopant is selected from compounds containing, for example, borohalide ions such as sulfur tetrafluoroborate, perhalogenate ions such as perchlorate ions, and sulfate ions. Next, the present invention will be explained in more detail with reference to Examples. Various electrolytically oxidized substances were dissolved or dispersed together with dopants in various solvents, and the electrolytically oxidized substances were oxidized under various conditions to obtain conductive or semiconductive polymer compositions on a platinum anode. This was washed with methanol and then dried under vacuum for a day and night to be used as a sample. In the case of a bulk sample, the sample was further ground into powder, then pressure-molded into a 1 mm thick disc, and both sides were coated with silver paint to prepare a sample for conductivity measurement. For film samples, make four samples with a width of 15 mm and a length of 110 mm, two of which are coated with silver paint and used as samples for conductivity measurement using the four-probe method, and the other two are JIS
The bending strength of P8115-1960 was used as a test sample. The following table shows the electrolytic oxidizing substance, the type and amount of the dopant, the type of solvent, the electrolytic oxidation conditions, and the conductivity value. The initial amount of electrolytically oxidized material is 1 g, the amount of solvent is 100 ml, and the amount of dopant is expressed in g units.
Furthermore, the conductivity values in the table are the average values of two samples. As a comparative example, to change the doping period,
First, thiophene was electrolytically oxidized and then doped with a dopant, but a dense and smooth film-like polymer composition could not be obtained.
【表】
また、耐折強さ試験でどのフイルムも50回以上
の折り曲げ回数を記録した。従来例として、ピロ
ール１ｇとホウ弗化テトラ−ｎ−ブチルアンモニ
ウム0.1ｇとをアセトニトリル100mlに溶解し、
20V、５ｍＡ／cm2で10分間通電して得た重合体組
成物の折り曲げ回数は10以下であつた。
上記実施例以外の電解酸化物質を用い、本発明
の方法で得た重合体組成物は、いずれも10-12
（Ω・cm）-1以上の導電率の値を示した。また、ド
ーパントの種類や量、溶媒の種類や電解酸化の条
件を適当に選んで緻密なフイルム状の重合体組成
物を得ることができた。
このようにして得られたもののうち、とくにフ
イルム状の重合体組成物はたとえば電子材料など
の素材として有用である。[Table] Furthermore, in the folding strength test, all films were folded more than 50 times. As a conventional example, 1 g of pyrrole and 0.1 g of tetra-n-butylammonium borofluoride were dissolved in 100 ml of acetonitrile.
The polymer composition obtained by applying current at 20 V and 5 mA/cm 2 for 10 minutes was bent no more than 10 times. All polymer compositions obtained by the method of the present invention using electrolytically oxidized substances other than the above-mentioned examples had a 10 -12
(Ω・cm) -1 or higher conductivity value. Furthermore, by appropriately selecting the type and amount of dopant, type of solvent, and electrolytic oxidation conditions, it was possible to obtain a dense film-like polymer composition. Among those obtained in this manner, film-like polymer compositions are particularly useful as raw materials for electronic materials and the like.
Claims (1)
だ物質をドーパントの共存下で電解酸化すること
を特徴とする導電性ないし半導電性重合体組成物
の製造方法。 (a) ベンゼンもしくはその誘導体 (b) 酸素族元素を１つ含む複素５員環化合物 (c) ベンゼン環と、酸素族元素もしくは窒素族元
素の少なくとも一方を含む複素５員環とよりな
る群から選んだ複数の環が直接又はエーテル、
スルフイド、セレニド、テルリド結合のうちい
ずれかの結合を介して直鎖状に結合した化合物 ２ 酸素族元素が、イオン、セレン及びテルルよ
りなる群から選んだものである特許請求の範囲第
１項記載の導電性ないし半導電性重合体組成物の
製造方法。 ３ ドーパントが、ホウハロゲン化イオン、パー
ハロゲネートイオンまたは硫酸イオンを含む化合
物から選ばれた特許請求の範囲第１項または第２
項記載の導電性ないし半導電性重合体組成物の製
造方法。[Claims] 1. A method for producing a conductive or semiconductive polymer composition, which comprises electrolytically oxidizing a substance selected from the group of compounds a, b, and c below in the presence of a dopant. (a) Benzene or its derivatives; (b) a five-membered heterocyclic compound containing one oxygen group element; and (c) from the group consisting of a benzene ring and a five-membered heterocyclic ring containing at least one of an oxygen group element or a nitrogen group element. The selected rings are direct or ether,
Compound 2 bonded linearly through any one of sulfide, selenide, and telluride bonds Claim 1, wherein the oxygen group element is selected from the group consisting of ions, selenium, and tellurium. A method for producing a conductive or semiconductive polymer composition. 3. Claim 1 or 2, wherein the dopant is selected from compounds containing borohalide ions, perhalogenate ions, or sulfate ions.
A method for producing a conductive or semiconductive polymer composition as described in 1.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7005482A JPS58187432A (en) | 1982-04-26 | 1982-04-26 | Preparation of electrically conductive or electrically semiconductive polymeric composition |
| US06/488,598 US4501686A (en) | 1982-04-26 | 1983-04-25 | Anion-doped polymers of five-membered oxygen family heterocyclic compounds and method for producing same |
| US06/675,644 US4582587A (en) | 1982-04-26 | 1984-11-28 | Anion-doped polymers of five-membered oxygen family heterocyclic compounds and method for producing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7005482A JPS58187432A (en) | 1982-04-26 | 1982-04-26 | Preparation of electrically conductive or electrically semiconductive polymeric composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58187432A JPS58187432A (en) | 1983-11-01 |
| JPH0520449B2 true JPH0520449B2 (en) | 1993-03-19 |
Family
ID=13420453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7005482A Granted JPS58187432A (en) | 1982-04-26 | 1982-04-26 | Preparation of electrically conductive or electrically semiconductive polymeric composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58187432A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6162520A (en) * | 1984-09-03 | 1986-03-31 | Res Dev Corp Of Japan | Production of electrically conductive polymer |
| JPS6162521A (en) * | 1984-09-03 | 1986-03-31 | Res Dev Corp Of Japan | Production of electrically conductive polymer |
| JPS62169820A (en) * | 1986-01-22 | 1987-07-27 | Res Dev Corp Of Japan | Polymer of five-membered heterocyclic compound |
| JPH0724608B2 (en) * | 1991-11-05 | 1995-03-22 | 三洋電機株式会社 | Frame leg device |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035713A2 (en) * | 1980-03-12 | 1981-09-16 | BASF Aktiengesellschaft | Process for preparing electrically conductive heteropolyphenylenes and their use in electrotechnics and in the antistatic equipment of synthetics |
-
1982
- 1982-04-26 JP JP7005482A patent/JPS58187432A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035713A2 (en) * | 1980-03-12 | 1981-09-16 | BASF Aktiengesellschaft | Process for preparing electrically conductive heteropolyphenylenes and their use in electrotechnics and in the antistatic equipment of synthetics |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58187432A (en) | 1983-11-01 |
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