JPH07116277B2 - Method for producing selenophene polymer - Google Patents
Method for producing selenophene polymerInfo
- Publication number
- JPH07116277B2 JPH07116277B2 JP60032808A JP3280885A JPH07116277B2 JP H07116277 B2 JPH07116277 B2 JP H07116277B2 JP 60032808 A JP60032808 A JP 60032808A JP 3280885 A JP3280885 A JP 3280885A JP H07116277 B2 JPH07116277 B2 JP H07116277B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- selenophene
- transition metal
- producing
- metal compound
- 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 - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims description 44
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 title claims description 35
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000003623 transition metal compounds Chemical class 0.000 claims description 17
- -1 molybdenum halides Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 150000005082 selenophenes Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000414 polyfuran Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
Landscapes
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は導電性材料として注目されているセレノフェン
重合体の製造方法に関する。〔従来の技術〕 セレノフェン重合体はその他の５員複素環式化合物の重
合体であるポリピロール、ポリフラン、ポリチオフェン
と並んで導電性材料として最近注目されている。これら
の重合体の製造方法としては電解重合法が知られてお
り、例えば、J.Chem.Soc.Chem.Comm.（1979）635頁、Ja
pan J.Applied Physi−cs21巻L562（1982）及び同誌23
巻L527（1984）にその方法が報告されている。TECHNICAL FIELD The present invention relates to a method for producing a selenophene polymer, which is attracting attention as a conductive material. [Prior Art] A selenophene polymer has recently attracted attention as a conductive material along with polypyrrole, polyfuran, and polythiophene, which are polymers of other 5-membered heterocyclic compounds. An electrolytic polymerization method is known as a method for producing these polymers. For example, J. Chem. Soc. Chem. Comm. (1979) p. 635, Ja.
pan J. Applied Physi-cs Volume 21 L562 (1982) and the same magazine 23
The method is reported in Volume L527 (1984).
然しながら従来の電解重合法では白金等の高価な電極、
特別な電解液、複雑な装置を必要とし、安価且つ大量に
生産できる方法とは云い難い。However, in the conventional electrolytic polymerization method, expensive electrodes such as platinum,
It is difficult to say that it is a method that can be mass-produced inexpensively because it requires a special electrolytic solution and a complicated device.
本発明の目的は叙上の観点に立って、安価且つ操作性良
くセレノフェン重合体を製造する方法を提供することに
ある。An object of the present invention is to provide a method for producing a selenophene polymer at low cost and with good operability from the above viewpoint.
本発明者等は前記目的を達成するために鋭意検討した結
果本発明を完成した。即ち本発明は、 セレノフェンを遷移金属化合物と接触せしめて重合させ
ることを特徴とするセレノフェン重合体の製造方法であ
る。The present inventors have completed the present invention as a result of extensive studies to achieve the above object. That is, the present invention is a method for producing a selenophene polymer, which comprises contacting selenophene with a transition metal compound and polymerizing the selenophene.
本発明に於て遷移金属化合物はその種類に制限をうけず
種々のものが使用可能であるが、中でも鉄、モリブデン
及びルテニウムのハロゲン化物、特に塩化第２鉄、塩化
モリブデン及び塩化ルテニウムが反応性も高く好適であ
る。In the present invention, various kinds of transition metal compounds can be used without any limitation, but among them, halides of iron, molybdenum and ruthenium, particularly ferric chloride, molybdenum chloride and ruthenium chloride are reactive. It is also high and suitable.
上記遷移金属化合物にセレノフェンの接触方法としては
両者を単に混合するだけでも良い。又溶媒を使用する方
法も用いられ、通常はこの方が反応を制御する上で好ま
しい。いずれの場合もかきまぜ等の機械的手段で接触さ
せてセレノフェン重合体とすることもできる。As a method of contacting the above transition metal compound with selenophene, the both may be simply mixed. A method using a solvent is also used, and this method is usually preferable in controlling the reaction. In any case, the selenophene polymer can be obtained by contacting with a mechanical means such as stirring.
又他の接触方法として、セレノフェンを気体状で遷移金
属化合物の溶媒溶液に接触させることも好ましい方法
で、この場合は膜状のセレノフェン重合体を得ることも
できる。例えば溶媒に溶解した遷移金属化合物を適当な
容器に入れ、その溶液中に必要に応じて窒素等の不活性
ガスでセレノフェン蒸気を同伴導入することにより、遷
移金属化合物溶液の上に膜状のセレノフェン重合体を生
成させることができる。As another contact method, it is also preferable to contact selenophene in a gaseous state with a solvent solution of a transition metal compound, and in this case, a film-shaped selenophene polymer can be obtained. For example, a transition metal compound dissolved in a solvent is placed in an appropriate container, and a selenophene vapor is introduced together with an inert gas such as nitrogen into the solution, if necessary, to form a film-like selenophene on the transition metal compound solution. A polymer can be formed.
本発明の方法で必要に応じて用いられる溶媒としては、
遷移金属化合物とは実質的に反応せず、しかも遷移金属
化合物を比較的良く溶解する溶媒が用いられる。好適に
用いられる溶媒としてはヘプタン、ヘキサン等の飽和炭
化水素、ジクロロメタン、クロロホルム、ジクロロエタ
ン等のハロゲン化炭化水素、或いはアセトニトリル、ベ
ンゾニトリル等のニトリル類があげられる。The solvent optionally used in the method of the present invention,
A solvent which does not substantially react with the transition metal compound and which dissolves the transition metal compound relatively well is used. Suitable solvents include saturated hydrocarbons such as heptane and hexane, halogenated hydrocarbons such as dichloromethane, chloroform and dichloroethane, and nitriles such as acetonitrile and benzonitrile.
セレノフェンと遷移金属化合物又はその溶液との接触温
度並びに時間については格別の制限はなく必要に応じて
定めれば良い。温度は常温でも良く、時間は数分乃至数
十時間接触させるのが好ましい。The contact temperature and time of the selenophene and the transition metal compound or the solution thereof are not particularly limited and may be set as necessary. The temperature may be room temperature, and it is preferable that the contact is performed for several minutes to several tens of hours.
本発明の方法で得られた重合体は、ろ過などにより余分
の遷移金属化合物及び未反応のセレノフェンを除去し、
必要に応じて前述の溶媒などを用いて洗浄した後乾燥す
る。The polymer obtained by the method of the present invention removes excess transition metal compound and unreacted selenophene by filtration or the like,
If necessary, it is washed with the above-mentioned solvent and the like and then dried.
ここに得られた重合体は遷移金属化合物がドーピングさ
れた状態であるので、必要があればアルコールやアセト
ン等で洗浄することによりドーピングされた遷移金属化
合物を除去したセレノフェン重合体を得ることができ
る。Since the polymer obtained here is in a state of being doped with a transition metal compound, it is possible to obtain a selenophene polymer free of the doped transition metal compound by washing with alcohol, acetone or the like, if necessary. .
本発明を実施例により具体的に説明する。 The present invention will be specifically described with reference to examples.
実施例−１ アルゴンで置換したドライボックス中で、塩化第２鉄2g
をクロロホルム100mlに溶解した溶液を調整した。この
溶液をスライドガラス上に塗布した後、セレノフェンの
蒸気を含む窒素気流中に置いた。この操作を10回繰り返
した。スライドガラス上に生成した重合体をクロロホル
ム、次いでメタノールで洗浄し減圧乾燥した。この重合
体は元素分析値が炭素36.19％、水素1.66％、セレン66.
25％で、Ｃ4.00Ｈ2.19Se1.05に相当し、セレノフエン重
合体の単位構造を示し、また室温での電気伝導度が10
-10Scm-1の次数で、ヨウ度をドーピングすることにより
電気伝導度が10-3Scm-1の次数まで上昇する重合体であ
った。Example 1 2 g of ferric chloride in a dry box replaced with argon
Was dissolved in 100 ml of chloroform to prepare a solution. After this solution was applied on a slide glass, it was placed in a nitrogen stream containing a vapor of selenophene. This operation was repeated 10 times. The polymer produced on the slide glass was washed with chloroform and then with methanol, and dried under reduced pressure. This polymer has an elemental analysis value of carbon 36.19%, hydrogen 1.66%, selenium 66.
At 25%, it corresponds to C 4.00 H 2.19 Se 1.05 , shows a unit structure of a selenophene polymer, and has an electric conductivity of 10 at room temperature.
It was a polymer with an order of −10 Scm −1 and conductivity increased to the order of 10 −3 Scm −1 by doping with iodine.
第１図に遷移金属化合物を除去する前後と、ヨウ素をド
ーピングした後のこの重合体の電気伝導度の温度依存性
を示す。図中ａはドーピングされた遷移金属化合物を除
去する前の重合体、ｂはそれを洗浄することにより遷移
金属化合物を除去した後の重合体、ｃはヨウ素をドーピ
ングした重合体である。FIG. 1 shows the temperature dependence of the electrical conductivity of this polymer before and after removing the transition metal compound and after doping with iodine. In the figure, a is a polymer before removing the doped transition metal compound, b is a polymer after removing the transition metal compound by washing it, and c is a polymer doped with iodine.
実施例−２ 実施例−１に於てスライドガラスの代りに導電性のITO
ガラスを用い、重合操作を３回繰り返した外は実施例−
１と同様の操作を行い、導電性ガラス上に乾燥された膜
状の重合体を生成させた。Example-2 In Example-1, conductive ITO was used instead of the slide glass.
Example-except that the polymerization operation was repeated 3 times using glass
The same operation as in 1 was performed to produce a dried film polymer on the conductive glass.
この導電性ガラス上に生成した重合体を用いて第２図の
表示素子用に使用できるセルを組みたてた。図中１はセ
レノフェン重合体、２は導電性ガラス、３は対電極、４
はガラスセル、５はテトラフルオロホウ酸リチウムのベ
ンゾニトリル溶液からなる電解液であり、６は直流電源
を示す。このセルに4.5Vの直流電流を流したところ、セ
レノフェン重合体の色は赤から青に変化し、両極を短絡
することで色は青から赤に戻った。A cell that can be used for the display device shown in FIG. 2 was assembled by using the polymer produced on the conductive glass. In the figure, 1 is a selenophene polymer, 2 is a conductive glass, 3 is a counter electrode, 4
Is a glass cell, 5 is an electrolytic solution composed of a benzonitrile solution of lithium tetrafluoroborate, and 6 is a DC power source. When a direct current of 4.5 V was applied to this cell, the color of the selenophene polymer changed from red to blue, and the color returned from blue to red by short-circuiting both electrodes.
生成された重合体は以上の性質を持つ外に、その電気伝
導度が電流を流す前は10-10Scm-1の次数で、電流を流す
と10-3Scm-1に上昇する重合体であった。In addition to having the above properties, the polymer produced is a polymer whose electrical conductivity is of the order of 10 -10 Scm -1 before the application of an electric current and rises to 10 -3 Scm -1 when an electric current is applied. there were.
実施例−３ 塩化第２鉄2gをクロロホルム100mlに溶かした溶液に、
セレノフェン1gをクロロホルム10mlに溶かした溶液を滴
下し、滴下終了後６時間かきまぜて反応を続けた。生成
した重合体をろ過し、クロロホルム、次いでメタノール
で洗浄後減圧乾燥した。Example 3 In a solution prepared by dissolving 2 g of ferric chloride in 100 ml of chloroform,
A solution prepared by dissolving 1 g of selenophene in 10 ml of chloroform was added dropwise, and the reaction was continued by stirring for 6 hours after the completion of the addition. The produced polymer was filtered, washed with chloroform and then with methanol, and dried under reduced pressure.
この重合体は元素分析値が炭素35.92％、水素1.84％、
セレン66.25％でＣ4.00Ｈ2.44Se1.05に相当し、セレノ
フェン重合体の単位構造を示し、また600kg/cm2で加圧
した板状にしたものは電気伝導度が10-10Scm-1の次数、
ヨウ素をドーピングすると10-3Scm-1の次数に上昇する
重合体であった。This polymer has an elemental analysis value of 35.92% carbon, 1.84% hydrogen,
66.25% of selenium corresponds to C 4.00 H 2.44 Se 1.05 and shows a unit structure of a selenophene polymer, and the plate-like material pressed at 600 kg / cm 2 has an electrical conductivity of 10 -10 Scm -1 . ,
It was a polymer that increased to the order of 10 -3 Scm -1 by doping with iodine.
本発明の方法によればセレノフェン重合体を安価で且つ
操作性良く製造することができ、殊に膜状のセレノフェ
ン重合体も簡単に製造することができる。According to the method of the present invention, a selenophene polymer can be produced at low cost and with good operability, and in particular, a membranous selenophene polymer can be easily produced.
比較例１ 本願明細書の実施例１において、溶液の調整をアルゴン
置換したドライボックス中で行なう代わりに、空気中で
行ない、重合をセレノフェンの蒸気を含む窒素気流中の
代わりにセレノフェンの蒸気を含む空気気流中で行なっ
た他は、実施例１と同様に行なったが、重合体は全く得
られなかった。Comparative Example 1 In Example 1 of the present specification, the solution is prepared in air instead of in a dry box substituted with argon, and the polymerization is performed in a nitrogen stream containing a vapor of selenophene. The procedure of Example 1 was repeated, except that the procedure was carried out in an air stream, but no polymer was obtained.
第１図は本発明のセレノフェン重合体及びヨウ素をドー
ピングしたセレノフェン重合体の電気伝導度の温度依存
性を示す図である。 第２図は本発明のセレノフェン重合体を用いた表示素子
として使用できるセルの構造を示す図である。 １……セレノフェン重合体 ２……導電性ガラス ３……対電極 ４……ガラスセル ５……電解液 ６……直流電源FIG. 1 is a diagram showing temperature dependence of electric conductivity of a selenophene polymer of the present invention and a selenophene polymer doped with iodine. FIG. 2 is a diagram showing the structure of a cell that can be used as a display device using the selenophene polymer of the present invention. 1 ... Selenophene polymer 2 ... Conductive glass 3 ... Counter electrode 4 ... Glass cell 5 ... Electrolyte 6 ... DC power supply
フロントページの続き (72)発明者 武田 淳子 大阪府富田林市別井94 (72)発明者 浅沼 正 大阪府高石市取石３丁目４―１―133 (72)発明者 内川 進▲隆▼ 大阪府高石市東羽衣６−21―４ (56)参考文献 特開 昭61−111336（ＪＰ，Ａ) 特開 昭59−202226（ＪＰ，Ａ) 特開 昭59−191727（ＪＰ，Ａ) 特開 昭59−43060（ＪＰ，Ａ)Front page continuation (72) Inventor Junko Takeda 94 Bei, Tomitabayashi, Osaka Prefecture (72) Inventor Tadashi Asanuma 3-4-1-133 Toriishi, Takaishi City, Osaka (72) Inventor Susumu Uchikawa Takatakaishi, Osaka Prefecture 6-21-4 Ichihigashi Hagori (56) Reference JP-A-61-111336 (JP, A) JP-A-59-202226 (JP, A) JP-A-59-191727 (JP, A) JP-A-59- 43060 (JP, A)
Claims (3)
化合物と接触せしめて重合させセレノフェン重合体単体
を得ることを特徴とするセレノフェン重合体の製造方
法。1. A method for producing a selenophene polymer, characterized in that selenophene polymer is obtained by bringing selenophene into contact with a transition metal compound in the absence of oxygen to polymerize the selenophene polymer.
フェン重合体が膜状で得られる特許請求の範囲第１項記
載のセレノフェン重合体の製造方法。2. The method for producing a selenophene polymer according to claim 1, wherein the selenophene polymer is obtained in the form of a film by bringing the selenophene into contact with a gas.
ゲン化モリブデン、ハロゲン化ルテニウムからなる群れ
より選ばれた１種以上である特許請求の範囲第１項記載
のセレノフェン重合体の製造方法。3. The method for producing a selenophene polymer according to claim 1, wherein the transition metal compound is at least one selected from the group consisting of ferric halides, molybdenum halides and ruthenium halides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60032808A JPH07116277B2 (en) | 1985-02-22 | 1985-02-22 | Method for producing selenophene polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60032808A JPH07116277B2 (en) | 1985-02-22 | 1985-02-22 | Method for producing selenophene polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61192725A JPS61192725A (en) | 1986-08-27 |
| JPH07116277B2 true JPH07116277B2 (en) | 1995-12-13 |
Family
ID=12369133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60032808A Expired - Fee Related JPH07116277B2 (en) | 1985-02-22 | 1985-02-22 | Method for producing selenophene polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07116277B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62201924A (en) * | 1986-02-28 | 1987-09-05 | Nitto Electric Ind Co Ltd | Production of thin electroconductive organic film |
| GB2445514B (en) * | 2005-11-24 | 2010-01-13 | Merck Patent Gmbh | Regioregular polyselenophenes |
| JP2011517701A (en) * | 2007-09-10 | 2011-06-16 | エダ リサーチ アンド ディベロップメント カンパニー，リミティド | Selenophene and selenophene polymers, their preparation, and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0618909B2 (en) * | 1984-11-06 | 1994-03-16 | 東レ株式会社 | Manufacturing method of composite materials |
-
1985
- 1985-02-22 JP JP60032808A patent/JPH07116277B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61192725A (en) | 1986-08-27 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |