[go: up one dir, main page]

WO2011081481A2 - Composition de polymère conducteur contenant un composé fluoré, dispersible dans un solvant organique - Google Patents

Composition de polymère conducteur contenant un composé fluoré, dispersible dans un solvant organique Download PDF

Info

Publication number
WO2011081481A2
WO2011081481A2 PCT/KR2010/009576 KR2010009576W WO2011081481A2 WO 2011081481 A2 WO2011081481 A2 WO 2011081481A2 KR 2010009576 W KR2010009576 W KR 2010009576W WO 2011081481 A2 WO2011081481 A2 WO 2011081481A2
Authority
WO
WIPO (PCT)
Prior art keywords
conductive polymer
ionic liquid
formula
fluorine
polymer composition
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/KR2010/009576
Other languages
English (en)
Korean (ko)
Other versions
WO2011081481A3 (fr
Inventor
서광석
김종은
김태영
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of WO2011081481A2 publication Critical patent/WO2011081481A2/fr
Publication of WO2011081481A3 publication Critical patent/WO2011081481A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/122—Ionic conductors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • 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
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to a conductive polymer composition synthesized using an ionic liquid polymer containing a fluorine-based compound, and more particularly, to a conductive polymer in which a polymer dopant and a fluorine compound are bonded in one molecule through an organic synthesis reaction. It relates to a technology and a composite conductive polymer compound made through the same.
  • Conductive polymers unlike general polymers, refers to a polymer that has its own electrical conductivity. Particularly, conductive polymers in which double bonds and double bonds are alternately bonded are themselves electrically insulating, but are electrically conductive when doped with a suitable component, and are antistatic materials and hole injection layer materials for organic light emitting devices. It is a polymer material applied to various fields, such as a transparent electrode material or an organic discoloration material.
  • poly (3,4-ethylenedioxythiophene): polystyrenesulfonic acid polystyrenesulfonic acid, PEDOT: PSS
  • PEDOT polystyrenesulfonic acid
  • This conductive polymer is a monomer of 3,4-ethylenedioxythiophene (3,4-ethylenedioxythiophene (EDOT) polystyrenesulfonic acid (PSSA), such as dopant and ammonium persulfate (APS) or ferric toluene sulfo It is mixed with an oxidizing agent (or initiator) such as ferric toluenesulfonate (FTS) and polymerized in water to prepare a solution.
  • EDOT 3,4-ethylenedioxythiophene
  • PSSA polystyrenesulfonic acid
  • APS dopant and ammonium persulfate
  • FTS ferric toluenesulfonate
  • the conductive polymer is a polystyrene sulfonic acid, which is a dopant, is dissolved in water, and the polymer chain has a polyethylene dioxythiophene, which is a conductive polymer, that is, a conductive polymer poly (ethylenedioxythiophene) that is solvent insoluble in a water-soluble polystyrene sulfonic acid chain.
  • a polystyrene sulfonic acid which is a dopant, is dissolved in water
  • the polymer chain has a polyethylene dioxythiophene, which is a conductive polymer, that is, a conductive polymer poly (ethylenedioxythiophene) that is solvent insoluble in a water-soluble polystyrene sulfonic acid chain.
  • a conductive polymer poly (ethylenedioxythiophene) that is solvent insoluble in a water-soluble polystyrene sulfonic acid chain.
  • the above-mentioned water-dispersible conductive polymer has a great advantage of being environmentally friendly because it is dispersed in water, and thus is a conductive polymer having a very high applicability as a hole injection / transport layer material of an antistatic composition and an organic light emitting device or a material for manufacturing a solar cell.
  • the water-dispersible conductive polymer made by the above-described method is dispersed in water or an aqueous solvent, various components and additives must be well dissolved or dispersed in water or an aqueous solvent when the composition is used for coating or other use.
  • it is difficult to use a system or a process that may cause a performance problem when water or a system in which water cannot be mixed may be used or must be treated separately.
  • the first method is a method of mixing a conventional water-dispersible PEDOT: PSS and a compound containing fluorine (eg, Nafion from DuPont).
  • a conventional water-dispersible PEDOT: PSS and a compound containing fluorine (eg, Nafion from DuPont).
  • the water of the PEDOT: PSS aqueous dispersion is evaporated, and is partially replaced by an organic solvent such as alcohol.
  • an organic solvent such as alcohol.
  • the second method is a method of fundamentally solving the above problems, and is a method of synthesizing a conductive polymer that can be dispersed in an organic solvent by using an entirely new compound having no sulfonic acid group as a dopant in manufacturing a conductive polymer.
  • an ionic liquid polymer is prepared using an ionic liquid as a monomer, and then a conductive polymer is synthesized using the ionic liquid polymer as a dopant molecule.
  • a conductive polymer is synthesized using the ionic liquid polymer as a dopant molecule.
  • the organic solvent dispersible conductive polymer made by this method i.e., made of an ionic liquid polymer
  • the hole injection layer material of the organic light emitting device there is a problem that the method of mixing with the fluorine compound has to be found again.
  • An object of the present invention is to provide a conductive polymer composition which is dispersible organic solvent and comprises a fluorine compound and a method for producing the same.
  • the present invention synthesizes an organic solvent dispersible conductive polymer composition composed of an ionic liquid polymer containing a conductive polymer and a fluorine-based compound, and provides an organic solvent dispersible conductive polymer composition prepared using the same. do.
  • the conductive polymer is a compound having a conjugated double bond in a cyclic structure including a hetero atom, as represented by Chemical Formula 1 below.
  • R 1 and R 2 are each selected from the group including hydrogen, halogen, or a hydrocarbon having 1 to 15 carbon atoms and optionally containing at least one hetero atom, or R 1 and R 2 together are a 3 to 8 membered aromatic ring Or alkylene, alkenylene, alkenyloxy, alkenyldioxy, alkynyloxy, alkynyldioxy, which form an aliphatic ring compound, selected from the group optionally containing one or more heteroatoms.
  • X represents any one selected from NH, NR, S, O, Se, and Te.
  • Representative conductive polymers of the present invention include polypyrrole, polythiophene, poly (3,4-ethylenedioxythiophene) and derivatives thereof.
  • an ionic liquid polymer containing a fluorine-based compound is a cation is an imidazolium-based polymer, and an anion is an organic or inorganic anion as shown in Formula 2.
  • the ionic liquid polymer may be a material having various physical and chemical properties according to a combination of a cation and an anion.
  • the ionic liquid polymer has a high solubility in an organic solvent and a stable dispersion of the conductive polymer in the organic solvent. It is advantageous.
  • R 3, R 4 , and R 5 are the same or different, and each represent hydrogen or a hydrocarbon group having 1 to 12 carbon atoms, and may optionally include one or more hetero atoms.
  • Y ⁇ represents an organic or inorganic anion
  • Z ⁇ represents an ionomer containing an fluorine atom.
  • the ionic liquid polymer including the fluorine-based compound represented by Chemical Formula 2 is basically a form in which an anion is bonded to the imidazolium-based polymer cation, and acts as a polymerization template of the conductive polymer as well as selective solubility in various organic solvents. Since there is a feature that can be assigned and controlled, it finally serves to allow the conductive polymer to be uniformly dispersed in a specific organic solvent. In addition, by including a large amount of fluorine atoms in the conducting polymer composition, it is possible to obtain the effect of improving the efficiency and lifespan of the organic light emitting device.
  • the imidazolium-based polymer cationic component examples include poly (1-vinyl-3-alkylimidazolium), poly (1-allyl-3-alkylimidazolium), and poly (1- (meth) acryloyloxy -3-alkylimidazolium) and the like, any one or more may be used, and the molecular weight of the imidazolium-based cationic polymer is 2,000 to 2,000,000 grams / mole.
  • the molecular weight of the imidazolium-based cationic polymer is 2,000 grams / mol or less, the molecular weight is too low and the particles of the conductive polymer finally made are too large, and if the molecular weight is 2,000,000 grams / mol or more, the solvent dispersibility of the ionic liquid polymer is low. It is disadvantageous for the synthesis of conductive polymers.
  • the organic or inorganic anion represented by Y ⁇ in Chemical Formula 2 is not particularly limited, but considering the solubility of the final product, [CH 3 CO 2 ] - , [HSO 4 ] - , [CH 3 OSO 3 ] - , [C 2 H 5 OSO 3 ] - , [AlCl 4 ] - , [CO 3 ] 2- , [HCO 3 ] - , [NO 2 ] - , [NO 3 ] - , [SO 4 ] 2- , [PO 4 ] 3-, [HPO 4] 2-, [H 2 PO 4] -, [HSO 3] -, [CuCl 2] -, Cl -, Br -, I -, [BF 4] -, [PF 6] - , [SbF 6 ] - , [CF 3 SO 3 ] - , [HCF 2 CF 2 SO 3 ] - , [CF 3 HFCCF 2 SO 3 ] -
  • the ionic liquid polymer including the fluorine-based compound of the present invention is characterized in that a part of the anion component (Z ⁇ ) is an ionomer containing an fluorine atom, and the ionomer containing the fluorine atom is represented by the following Chemical Formula 3 Can be.
  • a representative example of the ionomer containing the fluorine atom of Formula 3 is Nafion of DuPont, and since the fluorine-based ionomer contains a sulfone group (SO 3 ⁇ ) as an anion, it may bind to a cation of an ionic liquid. Can be.
  • R 6 and R 7 represent independently selected from F, Cl, or a perfluorinated alkyl group having 1 to 10 carbons.
  • x and y are each two or more natural numbers.
  • the anion binding to the ionic liquid cation may be represented by Y ⁇ and Z ⁇ , and the content ratio (Y / Z) of the ionic liquid anion of the present invention is 0 to 0.9.
  • Y / Z the entire anion is composed of ionomers containing fluorine atoms.
  • Y / Z is 0.9, 10% of all anions are substituted with ionomers containing fluorine atoms.
  • the ionic liquid polymer including the fluorine compound represented by Chemical Formula 2 may be prepared by the following method.
  • an imidazolium-based ionic liquid polymer is dissolved in water, and then a part or all of the anions of the ionic liquid polymer are substituted with an ionomer containing a fluorine atom to cause precipitation of the product.
  • the precipitated product obtained here is an ionic liquid polymer containing the fluorine-based compound of the present invention and is dissolved in various organic solvents through an additional anion substitution reaction.
  • the method for preparing an imidazolium-based ionic liquid polymer may be prepared as described in Korean Patent Laid-Open Publication No. 2009-0060110, and may use Dupont's Nafion as an ionomer containing fluorine atoms.
  • the ionic liquid polymer including the fluorine-based compound may be prepared by drying, and in this process, the content of the fluorine-based compound may be controlled by adjusting the content ratio of the ionic liquid polymer and Nafion.
  • the conductive polymer composition of the present invention is composed of the conductive polymer of Formula 1 and the ionic liquid polymer including the fluorine atoms of Formulas 2 and 3, and thus the finally synthesized conductive polymer composition is represented by Formula 4 below. It features.
  • a polymerization reaction is initiated by mixing a ionic liquid polymer including a monomer for synthesizing a conductive polymer represented by Chemical Formula 1, an oxidation initiator for synthesizing a conductive polymer, and a fluorine-based compound.
  • the polymerization reaction lasts for 3 hours to 72 hours, and the polymerization temperature is not particularly limited, but it is preferable to react at 0 to 30 degrees Celsius in consideration of the particle size of the finally produced conductive polymer composition.
  • the oxidation initiator is not particularly limited as long as it can induce a conductive polymer polymerization reaction, for example hydrogen peroxide, organic or inorganic peroxides, persulfates, peracids, peroxyacids, Bromates, chlorates, perchlorates, and iron (III), chromium (IV), chromium (VI), manganese (VII), manganese (V), manganese (IV), vanadium (V) ), Ruthenium (IV), organic or inorganic salts of copper (II), and the like may be used.
  • a conductive polymer polymerization reaction for example hydrogen peroxide, organic or inorganic peroxides, persulfates, peracids, peroxyacids, Bromates, chlorates, perchlorates, and iron (III), chromium (IV), chromium (VI), manganese (VII), manganese (V), manganese (IV), vanadium (V) ), Ruthenium (IV), organic
  • the content ratio of each component in the synthesis of the conductive polymer of the present invention is as follows.
  • 0.1-10 mole ratio of the ionic liquid polymer containing a fluorine-type compound may be used with respect to 1.0 mol of monomers for a conductive polymer synthesis. If the molar ratio of the ionic liquid polymer containing a fluorine-based compound is 0.1 or less, the content of the ionic liquid polymer, which is a component to be dispersed in the solvent, is too small to deteriorate organic solvent dispersibility, and if the content of the ionic liquid polymer is 10 or more The electrical conductivity of the synthesized conductive polymer is so low that it is rather disadvantageous.
  • the anion (Y) in the ionic liquid polymer of the present invention may be replaced with an ionomer (Z) containing a fluorine atom, and the content ratio (Y / Z) of the anion is 0 to 0.9. If Y / Z is 0.9 or more, the effect of adding fluorine compounds is small, and for example, it is disadvantageous in that the life extension of the organic light emitting device does not extend much.
  • the content of the oxidizing initiator is preferably 0.1 to 3 mol based on 1.0 mol of the monomer for synthesizing the conductive polymer. If the content of the oxidizing agent is less than 0.1 molar ratio, the oxidation reaction does not occur well and the synthesis of the conductive polymer is not good. If the molar ratio is more than 3.0 mole ratio, the oxidation reaction occurs so quickly that it is difficult to obtain the desired conductive polymer.
  • the synthetic solvent is not particularly limited, but water or methanol, ethanol, n-propyl alcohol, isopropyl alcohol, normal butanol, isobutanol, hexanol, ethylene glycol, glycerol, benzene, chlorobenzene, propylene carbonate, nitromethane, acetonitrile , Toluene, ethyl acetate, hexane, cyclohexane, 2-methoxyethanol, 2-butoxyethanol, 2-ethoxyethanol, 2-methoxypropanol, xylene, chloroform, tetrahydrofuran, dimethylformamide, methylethyl Ketone, N-methyl-2-pyrrolidone, 2-pyrrolidone, N-vinyl-2-pyrrolidone, N-methylformamide, dimethylsulfoxide, acetone, n-butyrolactone, etc. It includes the above.
  • the conductive polymer composition prepared by the technology of the present invention contains an ionic liquid polymer containing a fluorine-based compound, it is dispersed in various organic solvents and contains a large amount of fluorine atoms in a molecule, thereby being a functional material of an organic light emitting device or an organic solar cell. It can be utilized as.
  • the conductive polymer composition of the present invention is a material that is well dispersed in an organic solvent, a hole transport layer and a hole injection layer material of an organic light emitting diode device and a buffer material of an organic thin film transistor, It can be usefully used as other organic electronic materials.
  • the composition in order to significantly extend the life, the composition must be mixed with the fluorine compound to produce a composition, which is known to have a good effect. Since silver is a water-soluble compound, the water-soluble compound must be modified or modified to be mixed with an organic solvent dispersible thiophene-based conductive polymer or to have a conductive polymer having a fluorine compound.
  • a method of preparing an organic solvent dispersible conductive polymer composition using an ionic liquid polymer containing a fluorine compound is as follows.
  • the conductive polymer After imparting an organic solvent dispersibility or replacing an anion of the ionic liquid polymer with an ionomer containing a fluorine atom to form an ionic liquid polymer containing a fluorine compound and dissolving it in an organic solvent, the conductive polymer is added thereto. A monomer and an oxidizing initiator are administered to induce a polymerization reaction. It demonstrates more concretely below.
  • an ionomer containing a conductive polymer synthesis monomer, an oxidizing initiator, a water-soluble ionic liquid polymer (for example, an imidazolium-based ionic liquid polymer having a bromine group as an anion component) and a fluorine atom are mixed together, and water is
  • a conductive polymer composition is synthesized as described above.
  • the conductive polymer composition thus synthesized has a shape in which the conductive polymer is attached to the water-soluble ionic liquid polymer, but the conductive polymer itself is not dissolved in water, but since the ionic liquid polymer is dissolved in water, the synthesized conductive polymer eventually has water. It becomes acidic.
  • a part of the bromine group which is an anion of the ionic liquid polymer, is substituted with an ionomer containing a fluorine atom to form an ionic liquid polymer including a fluorine-based compound, and the conductive polymer composition having the conductive polymer bonded thereto is dispersed in water. It is made in the form that it is.
  • the method of converting the water-dispersible conductive polymer composition into an organic solvent dispersibility is as follows. As described above, water-dispersible conductive polymers are first prepared, and then lithium trifluorosulfonylimide is added to the dispersion to replace bromine groups, which are residual anions in ionic liquid molecules, so that they are converted into organic solvent solubility. do. The precipitate is obtained, washed well, dried, and then stirred in an organic solvent such as propylene carbonate, nitromethane, acetonitrile, and dimethylformamide. This dispersion is well dispersed in various organic solvents as an organic solvent dispersible conductive polymer composition.
  • an organic solvent such as propylene carbonate, nitromethane, acetonitrile, and dimethylformamide.
  • an organic solvent dispersible conductive polymer composition using an ionic liquid polymer containing a fluorine-based compound
  • the following method may be used. First, the anion of the ionic liquid polymer is replaced with an ionomer containing a fluorine atom to form an ionic liquid polymer including a fluorine compound and dissolved in an organic solvent.
  • An organic solvent dispersible conductive polymer composition is formed by administering a conductive polymer monomer and an oxidation initiator thereto and inducing a polymerization reaction.
  • the embodiment of the present invention used a conductive polymer mainly made of 3,4-ethylenedioxythiophene monomer.
  • the technique of the present invention is not limited to this monomer, but is applicable to all monomers shown in Formula 1, for example pyrrole, thiophene, or other conductive polymer monomers.
  • the composition of the organic solvent dispersible conductive polymer was prepared by the following method. 1.42 grams of 3,4-ethylenedioxythiophene and 2.03 grams of poly (1-vinyl-3-ethylimidazolium bromide) having a weight average molecular weight of 170,000 grams / mol are dissolved in 280 ml of water, and an ionomer containing fluorine atoms. DuPont's Nfion was added in an amount of 0.5 molar ratio relative to the ionic liquid polymer and mixed. Thereafter, ammonium persulfate, a polymerization initiator, was added dropwise at a molar ratio of 1.2 to monomers to prepare an aqueous conductive polymer composition through a polymerization reaction at room temperature.
  • lithium bis (trifluoromethinesulfonimide), an alkali metal salt was added at a 1.2 molar ratio to poly (1-vinyl-3-ethylimidazolium) bromide, followed by bromide and bis (trifluoromethanesulfonimide). Induce anion exchange reaction in the liver. The material precipitated through this reaction was washed and dried, and then again dispersed in dimethylformamide, which is an organic solvent, to give a solid content of 2% to prepare a conductive polymer composition dispersed in an organic solvent.
  • the conductive polymer composition powdery solution was coated on a polyester film at a thickness of about 100 nm and dried at a temperature of 100 degrees for 5 minutes, and the surface resistance thereof was measured at 10 6 ⁇ / ⁇ , and the contact angle was measured at 67 degrees.
  • Example 2 is the same as Example 1 except that Dupont's endion is mixed with an ionomer containing fluorine atoms in an amount of 1.0 molar ratio relative to the ionic liquid polymer.
  • the conductive polymer composition powdery solution was coated on a polyester film at a thickness of about 100 nm, dried at 100 ° C. for 5 minutes, and the surface resistance thereof was measured at 10 7 ⁇ s / ⁇ , and the contact angle was measured at 75 degrees.
  • Example 3 is the same as Example 2, except that 2.4 grams of poly (1-vinyl-3-butylimidazolium chloride) having a weight average molecular weight of 120,000 grams / mol are mixed as an ionic liquid polymer.
  • the conductive polymer composition powdery solution was coated on a polyester film at a thickness of about 100 nm and dried at a temperature of 100 degrees for 5 minutes, and the surface resistance thereof was measured as 10 7 ⁇ / ⁇ .
  • the organic solvent dispersible conductive polymer composition was prepared by the following method.
  • Aqueous conductive polymer composition was prepared through a polymerization reaction at room temperature while adding dropwise at a molar ratio of 1.2 to the monomer.
  • lithium bis (trifluoromethinesulfonimide), an alkali metal salt was added at a 1.2 molar ratio to poly (1-vinyl-3-ethylimidazolium) bromide, followed by bromide and bis (trifluoromethanesulfonimide). Induce anion exchange reaction in the liver. The material precipitated through this reaction was washed and dried, and then again dispersed in dimethylformamide, which is an organic solvent, to give a solid content of 2% to prepare a conductive polymer composition solution dispersed in an organic solvent.
  • the organic solvent dispersible conductive polymer composition was prepared by the following method.
  • the conductive polymer composition powdery solution was coated on a polyester film with a thickness of about 100 nm, and dried at a temperature of 160 degrees for 10 minutes, and the surface resistance thereof was measured as 10 8 ⁇ / ⁇ .
  • the conductive polymer compound according to the present invention is a material well dispersed in an organic solvent, a hole transport layer and a hole injection layer material of an organic light emitting diode device, and a buffer material of an organic thin film transistor. And other organic electronic materials.

Landscapes

  • Spectroscopy & Molecular Physics (AREA)
  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Conductive Materials (AREA)
  • Electroluminescent Light Sources (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

La présente invention concerne une technique de synthèse d'un polymère conducteur par emploi d'un polymère de type liquide ionique contenant un composé fluoré, ainsi qu'une technique de synthèse d'un polymère conducteur dans laquelle un polymère conducteur, un dopant de polymère et un composé fluoré sont combinés en une seule molécule via une réaction de synthèse organique, ainsi qu'un composé polymère conducteur composite synthétisé par une telle technique. Le composé polymère conducteur selon la présente invention est une matière facilement dispersible dans un solvant organique, et peut être employé en tant que matériau d'une couche de transport de trous ou d'une couche d'injection de trous d'une diode électroluminescente organique, ou en tant que matériau tampon d'un transistor à couches minces organiques et d'autres matériaux électroniques organiques.
PCT/KR2010/009576 2009-12-30 2010-12-30 Composition de polymère conducteur contenant un composé fluoré, dispersible dans un solvant organique Ceased WO2011081481A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020090134987A KR101523751B1 (ko) 2009-12-30 2009-12-30 유기 용매 분산성을 보유한 불소화합물을 포함하는 전도성 고분자 조성물
KR10-2009-0134987 2009-12-30

Publications (2)

Publication Number Publication Date
WO2011081481A2 true WO2011081481A2 (fr) 2011-07-07
WO2011081481A3 WO2011081481A3 (fr) 2011-11-10

Family

ID=44227067

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2010/009576 Ceased WO2011081481A2 (fr) 2009-12-30 2010-12-30 Composition de polymère conducteur contenant un composé fluoré, dispersible dans un solvant organique

Country Status (2)

Country Link
KR (1) KR101523751B1 (fr)
WO (1) WO2011081481A2 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2324807B1 (es) * 2008-01-31 2010-05-31 Fundacion Cidetec Composiciones electrocromicas basadas en viologenos formulables y aplicables a temperatura ambiente.

Also Published As

Publication number Publication date
KR101523751B1 (ko) 2015-05-28
KR20110078235A (ko) 2011-07-07
WO2011081481A3 (fr) 2011-11-10

Similar Documents

Publication Publication Date Title
TWI300419B (en) Process for the preparation of neutral polyethylenedioxythiophene, and corresponding polyethlenedioxythiophenes
TWI470024B (zh) 導電聚合物之磺化反應及有機發光二極體（ｏｌｅｄ）、光伏特與靜電耗散（ｅｓｄ）裝置
US8920681B2 (en) Electrically conductive polymers with enhanced conductivity
EP2014665A2 (fr) Polymères électriquement conducteurs contenant du sélénium et procédé de leur préparation
US20120052395A1 (en) Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams
US20090140219A1 (en) Selenium Containing Electrically Conductive Polymers and Method of Making Electrically Conductive Polymers
Jiang et al. Random terpolymer with a cost-effective monomer and comparable efficiency to PTB7-Th for bulk-heterojunction polymer solar cells
Somboonsub et al. Preparation of the thermally stable conducting polymer PEDOT–Sulfonated poly (imide)
WO2010058975A2 (fr) Composite nanotube de carbone-poly(x-4-styrènesulfonate) et composite nanotube de carbone- polymère électriquement conducteur produit au moyen de ce dernier
WO2010104349A2 (fr) Composés pouvant être utilisés en tant que matériaux pour former une couche d'injection à trous ou une couche de transport à trous, et diode électroluminescente organique constituée de ces composés
CN107001633B (zh) 聚合物、该聚合物的制备方法以及包含该聚合物的电解质膜
EP2523990A2 (fr) Polymères conducteurs thermostables, leurs procédés de fabrication et d'utilisation
WO2011071295A2 (fr) Composite nanotubes de carbone/liquide ionique polymère, et composite nanotubes de carbone/polymère conducteur préparé à l'aide de ce dernier
EP2520618B1 (fr) Polymère conducteur, composition de polymère conducteur, film de composition de polymère conducteur et dispositif photoélectrique l'utilisant
US8536300B2 (en) Photocrosslinkable electrically conductive polymers
KR101178288B1 (ko) 수용성 전기 전도성 폴리머
Gao et al. Cyclometalated Pt complex based random terpolymers as electron acceptors for all polymer solar cells
WO2010041876A2 (fr) Procédé de préparation de solution de dispersion de solvant organique pour polymère conducteur au moyen de liquide polymère ionique et polymère conducteur préparé par ce procédé
Tamilavan et al. Synthesis of conjugated polymers with broad absorption bands and photovoltaic properties as bulk heterojuction solar cells
Kanbara et al. Preparation of new redox-active quaternized poly (quinolinium) and poly (isoquinolinium) salts showing viologen-like redox behavior
WO2011081481A2 (fr) Composition de polymère conducteur contenant un composé fluoré, dispersible dans un solvant organique
Piyakulawat et al. Effect of thiophene donor units on the optical and photovoltaic behavior of fluorene-based copolymers
Zhou et al. Synthesis and Photovoltaic Properties of a Poly (2, 7‐carbazole) Derivative Based on Dithienosilole and Benzothiadiazole
Yamaguchi et al. Synthesis and chemical properties of pyrophosphoric acid-doped polyaniline and copolymers of o-phenylenediamine with aniline and 3, 4-ethylenedioxythiophene
KR101789920B1 (ko) 안정성이 향상된 전도성 고분자 용액 및 이의 경화 도막

Legal Events

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

Ref document number: 10841313

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10841313

Country of ref document: EP

Kind code of ref document: A2