WO2017191931A1 - Procédé de préparation d'un film mince en polymère conducteur traité par un acide perfluoré et son utilisation - Google Patents

Procédé de préparation d'un film mince en polymère conducteur traité par un acide perfluoré et son utilisation Download PDF

Info

Publication number
WO2017191931A1
WO2017191931A1 PCT/KR2017/004455 KR2017004455W WO2017191931A1 WO 2017191931 A1 WO2017191931 A1 WO 2017191931A1 KR 2017004455 W KR2017004455 W KR 2017004455W WO 2017191931 A1 WO2017191931 A1 WO 2017191931A1
Authority
WO
WIPO (PCT)
Prior art keywords
conductive polymer
thin film
polymer thin
perfluorinated acid
perfluorinated
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.)
Ceased
Application number
PCT/KR2017/004455
Other languages
English (en)
Korean (ko)
Inventor
김종만
이찬우
김태근
어경찬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Industry University Cooperation Foundation IUCF HYU
Original Assignee
Industry University Cooperation Foundation IUCF HYU
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Industry University Cooperation Foundation IUCF HYU filed Critical Industry University Cooperation Foundation IUCF HYU
Publication of WO2017191931A1 publication Critical patent/WO2017191931A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2218—Synthetic macromolecular compounds
    • C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
    • C08J5/2237—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C08L39/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/02—Polyamines
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
    • H10K71/421—Thermal treatment, e.g. annealing in the presence of a solvent vapour using coherent electromagnetic radiation, e.g. laser annealing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/80—Constructional details
    • H10K30/81—Electrodes
    • H10K30/82—Transparent electrodes, e.g. indium tin oxide [ITO] electrodes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a method for producing a perfluoroacid treated conductive polymer thin film and its use, and more particularly, to a method for producing a conductive polymer thin film capable of maintaining high conductivity for a long time and its use.
  • ITO inorganic metal materials
  • ITO inorganic metal materials
  • the material is made of a metal material, expensive deposition equipment is required to manufacture a thin film.
  • the electrical conductivity of PEDOT: PSS which is widely used as a conductive polymer, has a low electrical conductivity of about 1 S / cm, and is water soluble. When exposed to humidity, the film shape collapses due to swelling and the electrical conductivity is also sensitively reacted. . Therefore, when it comes into contact with the electrolyte layer used in solar cells, etc., it cannot be used in the electrode material due to the rapid electrical conductivity change.
  • polyaniline conductive polymers which are not water-soluble, if left for a long period of time, the air stability is very low and electrical conductivity is inevitable, and electrical conductivity is sensitively sensitive to various chemicals, which has a fatal disadvantage as an electrode material.
  • camphorsulfonic acid is known as the best dopant so far (electric conductivity is about 102 S / cm).
  • the present invention provides a method for producing a perfluorovolatile treated conductive polymer thin film and its use that can compensate for the disadvantages of a conductive polymer having low electrical conductivity and long-term stability.
  • the conductive polymer solution may be coated on a substrate to form a thin film, and then treated with a perfluorinated acid represented by Chemical Formula 1 to prepare a conductive polymer thin film.
  • n 3 to 20
  • A is SO 3 H, OPO 3 H or CO 2 H.
  • n in Chemical Formula 1 may be in the range of 4 to 9, specifically 6 to 8.
  • FIG. 1 is a schematic diagram showing a spontaneous alignment layer structure generated by doping a perfluorofluoric acid to a conductive polymer PEDOT: PSS (n is 6).
  • the perfluorinated acid represented by Chemical Formula 1 has a superhydrophobic, superhydrophobic, and chemical resistance in which a fluorine atom is substituted for hydrogen in a carbon main chain, and has a hydrophilic group having a high hydrophilicity at a terminal of the carbon main chain, a phosphate group, Alternatively, the carboxylic acid group is substituted to have an amphiphilic molecular structure having both hydrophilicity and hydrophobicity in the molecule.
  • an amphiphilic substance has a layered structure in which molecules are spontaneously oriented as in a cell membrane.
  • the hydrophilic functional group (sulfonic acid, etc.) in the perfluorinated acid of the present invention is capable of improving cationic conductivity by conducting cation doping to a conductive polymer. It can be used as, and having a spontaneously oriented layer structure of the super hydrophobic alkyl chain can lead the conductive polymer to the extended structure (to help the electrons flow more easily in the backbone of the conjugated polymer).
  • conductive polymers are oxidized by moisture and various contaminants in the air, and thus have a long term stability in terms of electrical conductivity.
  • Perfluorinated alkyl chain functional groups can act as membranes that induce superhydrophobic properties as well as spontaneously oriented layer structures, effectively blocking moisture or air contaminants in the air.
  • the perfluorinated acid plays a role in unfolding the conductive polymer chain and thus has a molecular structure through which electricity can flow well, and at the same time, it has a long-term stability of electrical conductivity.
  • n may be 3 to 20, and most preferably n may be 4 to 9. If the value of n is less than 3, it is difficult to maintain the electrical conductivity of the conductive polymer in the long term. If the value of n is more than 20, the size of the molecule is large, so that it is difficult to penetrate into the polymer, and thus doping is difficult. There is a problem.
  • the conductive polymer may be PEDOT: PSS, polyaniline or polypyrrole.
  • the conductive polymer may be a compound represented by Formula 2, Formula 3, or Formula 4.
  • PSS When the conductive polymer is PEDOT: PSS shown in Chemical Formula 2, PSS may be replaced with perfluorinated acid by treatment with perfluorinated acid represented by Chemical Formula 1.
  • PEDOT which is a conductive polymer
  • the perfluorinated acid which is a dopant, may exist in the perfluoroacid treated conductive polymer thin film.
  • the conductive polymer is t-Boc-polyaniline represented by the formula (4)
  • some of the t-Boc-polyaniline by the treatment of perfluorinated acid represented by the formula (1) is in the emeraldine base state of the t-Boc desorbed Can return to polyaniline. In this case, an improvement in conductivity may appear.
  • the treating with the perfluorofluoric acid may be performed by applying a perfluorinated acid aqueous solution onto the conductive polymer thin film and then heating at 80 to 120 ° C. for 2 to 60 minutes, more preferably at 100 ° C. for 5 to 30 minutes. Can be.
  • the aqueous solution of perfluorinated acid may be 10 to 50 (wt / v)%, more preferably 30 (wt / v)%.
  • the conductive polymer solution may be mixed with the perfluorofluoric acid represented by Chemical Formula 1 and then coated on a substrate to prepare a conductive polymer thin film.
  • the solute and the perfluorinated acid of the conductive polymer solution may be mixed in a weight ratio of 100: 0.01-50. More preferably, it may be mixed in a weight ratio of 100: 10 to 30.
  • the polyaniline units of Chemical Formulas 3 and 4 and the perfluorinated acid of Chemical Formula 1 may be mixed in a weight ratio of 100: 0.01 to 50, and more preferably 100: 10 to 30 weight ratio. It can be mixed with.
  • the perfluorinated acid may be mixed to suit the weight ratio of the conductive polymer. That is, when mixed with the perfluorinated acid in the above range, the polarization band such as a radical cation is delocalized in the structure of the conductive polymer generated during the doping can be effectively controlled to the doping level through which electrons can flow well in the polymer chain. have. Accordingly, the electrical conductivity and long-term stability of the thin film to be produced can be significantly improved.
  • the substrate may be selected from the group consisting of silicon wafers, glass plates, PET plastic substrates, paper and metal substrates.
  • the thin film may be well formed on a flexible PET substrate as well as glass, a silicon wafer, or the like.
  • the solvent of the conductive polymer solution may be water, methacresol, tetrahydrofuran or chloroform.
  • the thin film may be formed by a spin coating method or a doctor blade method, but is not limited thereto.
  • the same parts as those described above for the conductive polymer are omitted.
  • the present invention provides a transparent electrode material consisting of a conductive polymer thin film treated with a perfluorinated acid represented by the formula (1).
  • a transparent electrode material consisting of a conductive polymer thin film treated with a perfluorinated acid represented by the formula (1). The same parts as those described above for the conductive polymer are omitted.
  • the present invention provides a method for stabilizing the electrical conductivity of a conductive polymer thin film comprising the step of coating a conductive polymer solution on a substrate to form a thin film, and then treating with a perfluorinated acid represented by the formula (1).
  • the present invention provides a method for stabilizing the electrical conductivity of the conductive polymer thin film comprising the step of forming a thin film by mixing the perfluorinated acid represented by the formula (1) in the conductive polymer solution, the coating on the substrate.
  • compositions comprising a conductive polymer and a perfluorinated acid represented by the following Chemical Formula 1, a conductive polymer thin film manufacturing composition.
  • the composition may include a conductive polymer and a perfluorinated acid in a weight ratio of 100: 0.01 to 50.
  • the conductive polymer is a polyaniline emeraldine base
  • the polyaniline emeraldine base and the perfluorinated acid may be included in a weight ratio of 100: 5-30.
  • the same parts as those described above for the conductive polymer are omitted.
  • the perfluorinated acid according to the present invention by applying a perfluorinated acid dopant having an amphiphilic molecular structure, it is possible to significantly improve the electrical conductivity of the conductive polymer thin film and maintain it for a long time.
  • the perfluorinated acid according to the present invention has superhydrophobic properties in which a fluorine atom is substituted for hydrogen in the carbon chain. It also has a structure that can be spontaneously oriented as an amphiphilic monomer compound in which hydrophilic groups such as sulfonic acid, phosphoric acid and carboxylic acid are substituted at the chain ends.
  • the perfluorinated acid according to the present invention has a lower molecular weight than the conductive polymer, so that it is relatively easy to penetrate into the conductive polymer, and can be evenly doped in an unlocalized form throughout the molecule.
  • perfluorinated compounds have inherent properties of superhydrophobic and chemical resistance.
  • Superhydrophobic perfluorinated hydrocarbon compounds are able to push out water and oil components and are used in super water-repellent coatings because of their inherent chemical stability.
  • Perfluorinated acid has a high acidity and dielectric constant of sulfonic acid due to the induction effect of attracting electrons by substitution of F atom having the largest electronegativity. Therefore, perfluorinated acid can effectively increase the electrical conductivity by cationically doping the conductive polymer.
  • spontaneously oriented superhydrophobic alkyl chains can effectively prevent water and chemicals, so that they can be stored in the air for a long time or have no electrical conductivity reduction under various organic acid and base conditions. You can give it.
  • the thin film of the conductive polymer prepared according to the present invention can be used in many organic electronic devices such as various displays, OLED, solar cell hole transport layer.
  • the material of the present invention can ensure high conductivity, high transmittance and long-term stability can be used as a transparent electrode material in place of ITO material.
  • FIG. 1 is a schematic diagram showing a spontaneous alignment layer structure generated by doping a perfluorofluoric acid to a conductive polymer PEDOT: PSS (n is 6).
  • Example 2 is an image of a conductive polymer thin film according to Example 1: (a) glass substrate (before spin coating) (b) after spin coating of conductive polymer solution (c) after perfluorofluoric acid treatment
  • Example 3 is an image of a conductive polymer thin film according to Example 3: (a) before spin coating (b) after perfluorofluoric acid treatment (c) after spin coating of conductive polymer solution
  • Example 4 is a graph showing the electrical conductivity of the conductive polymer thin film according to Example 1 and Comparative Examples 1 and 2.
  • Example 5 is a graph showing the results of UV spectrum analysis of the conductive polymer thin film according to Example 1 and Comparative Example 2.
  • Example 6 is a graph showing the infrared spectrum analysis results of the conductive polymer thin film according to Example 1 and Comparative Example 2.
  • Example 7 is a graph showing the Raman spectrum analysis results of the conductive polymer thin film according to Example 1 and Comparative Examples 1 and 2.
  • Example 8 is a graph comparing the transmittance of the conductive polymer thin film according to Example 1 and Comparative Examples 1 and 2.
  • PEDOT: PSS aqueous solution (Clevious Co., Ltd.) was filtered using a 0.45 mm filter to remove fine particles in the solid state, and then spin-coated to a glass or transparent substrate to obtain a uniform film state.
  • the electrical conductivity of the thin film was about 1 S / cm.
  • an aqueous solution of perfluorinated octane sulfonic acid (PFOSA 40% in water) was applied onto the PEDOT: PSS thin film, and then heated to 100 ° C. for 20 minutes to dope the PEDOT: PSS thin film.
  • the doped thin film was washed with distilled water and ethanol and dried to measure electrical conductivity. It was confirmed that the electrical conductivity is about 4500 S / cm.
  • FIG. 2 shows images obtained after (a) glass substrate (before spin coating), (b) after spin coating of conductive polymer solution, and (c) after treatment with perfluoric acid obtained during the preparation of the conductive polymer thin film according to Example 1.
  • FIG. 2 shows images obtained after (a) glass substrate (before spin coating), (b) after spin coating of conductive polymer solution, and (c) after treatment with perfluoric acid obtained during the preparation of the conductive polymer thin film according to Example 1.
  • Example 2 Perfluorovolatiles (PFOSA: 8 carbon atoms) Doped PEDOT: PSS Preparation of Thin Films (PFOSA and PEDOT: PSS Mixture)
  • a 15 wt / v% aqueous solution of PFOSA was mixed with 1 ml of an aqueous PEDOT: PSS solution and treated with an ultrasonic cleaner for 30 minutes.
  • the solution was filtered using a 0.45 mm filter, followed by spin coating on a glass or transparent substrate to prepare a uniform film, and then heating at 100 ° C. for 5 minutes to complete a thin film.
  • Example 3 Perfluorovolatiles (PFOSA: 8 carbon atoms) Doped t- Boc - Polyaniline High conductivity Thin film manufacturing
  • t-Boc-polyaniline 50 mg was dissolved in 1 ml of chloroform and sonicated for 10 minutes and then filtered using a 0.45 mm filter to prepare a composition solution.
  • the composition solution was spin coated onto a glass plate to prepare a thin film.
  • 30 wt% PFOSA aqueous solution was applied and then doped by heating at 100 ° C. for 5 minutes.
  • the doped thin film was washed with distilled water and ethanol and dried to measure electrical conductivity. As a result of the measurement, the electrical conductivity was about 200 S / cm.
  • FIG. 3 shows images obtained after (a) t-Boc-polyaniline spin coating and (b) perfluorinated acid obtained during the preparation of a conductive polymer thin film according to Example 3, and (c) polyaniline spin in an emeraldine-based state. The image in the case of coating is shown.
  • the polyaniline (c) of the emeraldine base state is blue, but the t-Boc-polyaniline (a) having a t-Boc functional group introduced into the polyaniline is brown.
  • PFOSA doping a t-Boc-polyaniline thin film with PFOSA (b)
  • Comparative example 3 Perfluorovolatiles (1 carbon) Doped PEDOT: PSS Manufacture of thin film
  • PEDOT: PSS aqueous solution (Clevios Co., Ltd.) was filtered using a 0.45 mm filter to remove fine particles in the solid state, and then spin-coated to a glass or transparent substrate to obtain a uniform film state. Thereafter, an aqueous solution of CF 3 -SO 3 H perfluorinated acid was applied onto the PEDOT: PSS thin film, and then heated at 100 ° C. for 20 minutes to dope the PEDOT: PSS thin film. The doped thin film was washed with distilled water and ethanol and dried to measure electrical conductivity.
  • Figure 4 is a graph showing the electrical conductivity over time of the conductive polymer thin film according to Example 1, Comparative Example 1, and Comparative Example 2.
  • PFOSA Perfluorofluoric acid
  • Example 5 is a graph showing the UV-vis absorption spectrum of the conductive polymer thin film according to Example 1 and Comparative Example 2.
  • the absorption bands appearing in the 230 nm region of the PEDOT: PSS thin film (Comparative Example 2) prepared without the doping step are due to the PSS, and the absorption band is a PEDOT: PSS thin film doped with perfluorinated acid (implemented In Example 1, the intensity is reduced.
  • the PSS in the PEDOT: PSS thin film is partially removed during the washing after the perfluorinated dope, and further, the PSS of the PEDOT: PSS may be replaced by the perfluorinated fluoride by the perfluorinated dope.
  • FIG. 6A is a graph showing an infrared spectrum of the conductive polymer thin film according to Example 1 and Comparative Example 2, and FIG. 6B is an enlarged graph showing a region between wave numbers 1500 to 1000 cm ⁇ 1 of FIG. 6A.
  • the PEDOT: PSS thin film doped with perfluorinated sulfonic acid according to Example 1 showed a typical perfluorinated sulfonic acid peak at a 1280 cm ⁇ 1 position. This means that the perfluorinated acid is doped in the PEDOT: PSS thin film.
  • FIG. 7A is a graph showing Raman spectra of conductive polymer thin films according to Example 1, Comparative Example 1, and Comparative Example 2, and FIG. 7B is an enlarged graph showing a region between wave numbers 1200 to 1700 cm ⁇ 1 of FIG. 7A. .
  • Comparative Examples 1 and 2 according to the PEDOT: PSS film is 1445 cm - PEDOT according to the first embodiment shows a peak in the vicinity of 1,: PSS films peak near 1422 cm -1 It can be seen that indicates.
  • Example 8 is a graph showing the transmittance of the conductive polymer thin film according to Example 1, Comparative Example 1, and Comparative Example 2.
  • the thin film according to Example 1 exhibits excellent transmittance (95%) in the visible light region, and thus may be sufficiently replaced by a transparent electrode material such as ITO.
  • the conductive polymer thin film doped with CF 3 -SO 3 H has a high initial electrical conductivity, but is rapidly decreased with time.
  • the short chain length and low boiling point make it difficult to effectively dope the PEDOT polymer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Optics & Photonics (AREA)
  • Non-Insulated Conductors (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacturing Of Electric Cables (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un film mince en polymère conducteur, traité par un acide perfluoré, ainsi que son utilisation, et plus particulièrement un procédé de préparation d'un film mince en polymère conducteur qui permet une conservation à long terme d'une conductivité élevée et son utilisation. La présente invention permet une nouvelle amélioration et une conservation à long terme de la conductivité électrique d'un film mince polymère par application d'un dopant à base d'un acide perfluoré présentant une structure moléculaire amphiphile.
PCT/KR2017/004455 2016-05-02 2017-04-26 Procédé de préparation d'un film mince en polymère conducteur traité par un acide perfluoré et son utilisation Ceased WO2017191931A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020160054148A KR102534789B1 (ko) 2016-05-02 2016-05-02 과불소화산 처리된 전도성 고분자 박막의 제조방법 및 이의 용도
KR10-2016-0054148 2016-05-02

Publications (1)

Publication Number Publication Date
WO2017191931A1 true WO2017191931A1 (fr) 2017-11-09

Family

ID=60202883

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2017/004455 Ceased WO2017191931A1 (fr) 2016-05-02 2017-04-26 Procédé de préparation d'un film mince en polymère conducteur traité par un acide perfluoré et son utilisation

Country Status (2)

Country Link
KR (1) KR102534789B1 (fr)
WO (1) WO2017191931A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116925349A (zh) * 2023-07-21 2023-10-24 中国计量大学 一种化学改性聚苯胺复合防腐涂料及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102379726B1 (ko) 2020-03-04 2022-03-28 한양대학교 산학협력단 산을 이용한 후처리에 기반하는 전자소자의 제조방법

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4462929A (en) * 1982-09-30 1984-07-31 Allied Corporation Solution of a chalcogen-containing polymer in acids and process of forming polymer articles therefrom
KR20080036056A (ko) * 2005-06-27 2008-04-24 이 아이 듀폰 디 네모아 앤드 캄파니 전기 전도성 중합체 조성물
KR20080039884A (ko) * 2005-06-28 2008-05-07 이 아이 듀폰 디 네모아 앤드 캄파니 완충 조성물
JP2013505565A (ja) * 2009-09-18 2013-02-14 オスラム オプト セミコンダクターズ ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機電子デバイス、並びに有機半導体マトリックス材料をドープするためのドーパント
US20140060602A1 (en) * 2011-03-28 2014-03-06 Fujifilm Corporation Electrically conductive composition, an electrically conductive film using the composition and a method of producing the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4462929A (en) * 1982-09-30 1984-07-31 Allied Corporation Solution of a chalcogen-containing polymer in acids and process of forming polymer articles therefrom
KR20080036056A (ko) * 2005-06-27 2008-04-24 이 아이 듀폰 디 네모아 앤드 캄파니 전기 전도성 중합체 조성물
KR20080039884A (ko) * 2005-06-28 2008-05-07 이 아이 듀폰 디 네모아 앤드 캄파니 완충 조성물
JP2013505565A (ja) * 2009-09-18 2013-02-14 オスラム オプト セミコンダクターズ ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機電子デバイス、並びに有機半導体マトリックス材料をドープするためのドーパント
US20140060602A1 (en) * 2011-03-28 2014-03-06 Fujifilm Corporation Electrically conductive composition, an electrically conductive film using the composition and a method of producing the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116925349A (zh) * 2023-07-21 2023-10-24 中国计量大学 一种化学改性聚苯胺复合防腐涂料及其制备方法

Also Published As

Publication number Publication date
KR102534789B1 (ko) 2023-05-19
KR20170124674A (ko) 2017-11-13

Similar Documents

Publication Publication Date Title
DE60305541T2 (de) Polythiophene und damit hergestellte Vorrichtungen
JP4668916B2 (ja) 有機高分子、電子デバイス、および方法
DE69104204T2 (de) Mis-struktur-dünnschichttransistor mit isolator und halbleiter aus organischem material.
DE60307687T2 (de) Polythiophene und damit hergestellte Vorrichtungen
US20060081841A1 (en) Gelable composition
KR100913700B1 (ko) 아민 화합물을 포함하는 탄소 나노튜브(ｃｎｔ) 박막 및 그제조방법
KR20040039464A (ko) 조성물, 방법 및 전자 디바이스
WO2017191932A1 (fr) Diacétylène soluble dans l'eau, composition de photolithographie comprenant un monomère de diacétylène soluble dans l'eau et un polymère conducteur et procédé de préparation de motifs fins l'utilisant
Kwiatkowska et al. Investigation of polyaniline doped with camphorsulfonic acid in chloroform solution as a hole transporting layer in PTB7: PCBM and perovskite-based solar cells
EP3373354B1 (fr) Composition pour couche de piégeage de trous d'élément de conversion photoélectrique organique
CN116635489A (zh) 获得聚合物纳米粒子分散液和n型导电油墨的方法
WO2010117126A1 (fr) Composition de pâte composite en nanotubes de carbone/métal pour une contre-électrode d'une cellule solaire sensibilisée par colorant, et contre-électrode composite en nanotubes de carbone/métal
KR20100125396A (ko) 화상 형성용 하층막 조성물
WO2017191931A1 (fr) Procédé de préparation d'un film mince en polymère conducteur traité par un acide perfluoré et son utilisation
US20090256138A1 (en) Organic thin film transistor
US20070259473A1 (en) Process to form tft gate dielectric with crosslinked polymer
US20150188054A1 (en) Cellulose-polymer composites for solar cells
JP2005507180A (ja) 有機電子デバイス用の絶縁体
KR100242220B1 (ko) 전기전도성 교호공중합체 및 이의 제조방법
WO2017078390A1 (fr) Couche semi-conductrice organique comprenant un nanotube de carbone, son procédé de fabrication, et transistor à couches minces l'utilisant
WO2020040361A1 (fr) Film mince, son procédé de formation et cellule solaire de pérovskite comprenant un film mince
KR101856563B1 (ko) 액정성 유기박막 트랜지스터 및 그 제조방법
US20090242878A1 (en) Optimization of new polymer semiconductors for better mobility and processibality
EP2817350A2 (fr) Polymères contenant des unités structurales sous forme de dibenzocycloheptane
US20130092878A1 (en) Thermoplastic based electronic conductive inks and method of making the same

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17792833

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 17792833

Country of ref document: EP

Kind code of ref document: A1