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WO2013032059A1 - Composition conductrice et son procédé de fabrication - Google Patents

Composition conductrice et son procédé de fabrication Download PDF

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Publication number
WO2013032059A1
WO2013032059A1 PCT/KR2011/007547 KR2011007547W WO2013032059A1 WO 2013032059 A1 WO2013032059 A1 WO 2013032059A1 KR 2011007547 W KR2011007547 W KR 2011007547W WO 2013032059 A1 WO2013032059 A1 WO 2013032059A1
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WIPO (PCT)
Prior art keywords
conductive polymer
weight
parts
polymer composition
composition
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PCT/KR2011/007547
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English (en)
Korean (ko)
Inventor
진용현
정경원
송순모
이재준
Original Assignee
(주)누리비스타
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Priority to CN201180072978.3A priority Critical patent/CN103764766A/zh
Publication of WO2013032059A1 publication Critical patent/WO2013032059A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/02—Cellulose; Modified cellulose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • 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
    • 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
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/43—Chemical oxidative coupling reactions, e.g. with FeCl3
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/51—Charge transport

Definitions

  • the present invention relates to a conductive polymer composition and a method for preparing the same, and more particularly, to poly (3,4-ethylenedioxythiophene) by adding polycellulose sulfonate as a dopant to poly (3,4-ethylenedioxythiophene).
  • the present invention relates to a conductive composition having high electrical crosslinking density and excellent stability and a method for producing the same.
  • the conductive polymer is an organic material and has the advantage of passing electricity, so the usefulness of the conductive polymer is very diverse. Recently, conductive polymers are applied in real life and high-tech industries such as touch panels, flexible display devices, flexible solar transparent electrodes, electronic notebooks, secondary batteries, antistatic, switching devices, nonlinear devices, capacitors, optical recording materials, and electromagnetic shielding materials. It is becoming.
  • the conductive polymer In order for the conductive polymer to have conductivity, a doping process is required. Typically, after the powder form or film form, they are chemically doped, or by mixing the conductive powder and the dopant is dissolved by an organic solvent to make a conductive method.
  • poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (PEDOT / PSS) is stable in the air, and has high electrical conductivity at room temperature compared to other polymers, and has been applied in various fields.
  • samples doped with poly (3,4-ethylenedioxythiophene) and doped with poly (4-styrenesulfonate) (PSS) with dopants have very uniform coatings with electrodes or antistatic materials, and have excellent interfacial properties and adhesion. Excellent application, wide application.
  • the present invention is to replace the poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate), and more particularly relates to a novel conductive polymer composition and a method for producing the same by replacing the dopant with another material. .
  • An object of the present invention is to increase the crosslinking density of poly (3,4-ethylenedioxythiophene) by adding polycellulose sulfonate as a dopant to poly (3,4-ethylenedioxythiophene), and have excellent electrical conductivity and stability. It is to provide a composition and a method for producing the same.
  • the conductive composition of the present invention for achieving the above object is (a) a random copolymer having a unit structure represented by the following formula (1) doped with a polycellulose sulfonate doped with a polycellulose sulfonate having at least one sulfonate group in the copolymer and ( b) characterized by comprising a solvent.
  • R is —H, — (CH 2 CH 2 ) —OH, —CH 2 CH 2 OCH 2 CH (OH) CH 2 SO 3 H, —CH 2 CH 2 OCH 2 CH (OH) CH 2 O -mC 18 H 37 one selected from m, at least one.
  • Method for producing a conductive composition of the present invention for achieving the above object (A) preparing a conductive polymer monomer solution containing a conductive polymer monomer, polycellulose sulfonate and a solvent and (B) polymerizing the conductive polymer monomer solution Characterized in that it comprises a step.
  • the conductive polymer composition according to the present invention comprises (a) a random copolymer having a unit structure represented by the following Chemical Formula 1, and a conductive polymer doped with a polycellulose sulfonate having at least one sulfonate group in the copolymer, and (b) a solvent. It is characterized by including.
  • R is —H, — (CH 2 CH 2 ) —OH, —CH 2 CH 2 OCH 2 CH (OH) CH 2 SO 3 H, —CH 2 CH 2 OCH 2 CH (OH) CH 2 O -mC 18 H 37 one selected from m, at least one.
  • the crosslinking density of the conductive polymer is increased, and electrical conductivity and thermal stability are improved.
  • the components of the conductive polymer composition of the present invention will be described in detail.
  • the conductive polymer of the present invention is an electrically conductive polymer having one? Electron per carbon atom, and generally has a molecular weight of about 3,000 or more.
  • the conductive polymer has the advantage of being able to obtain a thin film having a high weight and flexibility compared to ITO, which is generally used as a transparent electrode.
  • Dopant refers to a material that acts as a charge carrier by adding or removing charges to a part of the ⁇ orbital function of the conductive polymer of the present invention. Dopants are generally added to give conductivity to the conductive polymer. The doping is added to the conductive polymer to form a charge carrier. Specifically, when providing charge to the conductive polymer is called doping (n-type doping), when removing the charge from the conductive polymer is called p-type doping (p-type doping).
  • the electrical conductivity of the conductive polymer composition is increased and the thermal stability is increased by doping the conductive polymer using polycellulose sulfonate.
  • the polycellulose sulfonate used as the dopant is a random copolymer having a unit structure represented by the following formula (1), and has at least one sulfonate group in the copolymer.
  • R is —H, — (CH 2 CH 2 ) —OH, —CH 2 CH 2 OCH 2 CH (OH) CH 2 SO 3 H, —CH 2 CH 2 OCH 2 CH (OH) CH 2 O -mC 18 H 37 one selected from m, at least one.
  • the distance between the poly (3,4-ethylenedioxythiophene) conductive polymers is shortened, and the electrical conductivity of the conductive polymer composition is improved.
  • the conductive polymer doped with the polycellulose sulfonate of the present invention may be any of polythiophene-based, polypyrrole-based, polynetylene-based, polyaniline-based or polyacetylene-based.
  • the polythiophene-based conductive polymer is preferably poly (3,4-ethylenedioxythiophene).
  • Poly (3,4-ethylenedioxythiophene) / polycellulose sulfonate has the advantages of high electrical conductivity, excellent thermal stability, and good transparency.
  • the content of the conductive polymer doped with polycellulose sulfonate is preferably 0.1 to 50 parts by weight, more preferably 0.1 to 20 parts by weight.
  • the content of the conductive polymer doped with polycellulose sulfonate is less than 0.1 part by weight, it is difficult to realize high conductivity of 1 dB / ⁇ or less even when a large amount of polar solvent is used as an additional dopant, and when it exceeds 50 parts by weight, the long wavelength of visible light If the area (550 nm) or more, the transmittance is reduced, there is a problem that the coating workability is not easy.
  • a solvent included in the conductive composition of the present invention is added to disperse the conductive polymer in the solution phase.
  • the solvent of the present invention may be at least one selected from water, aliphatic alcohols, aliphatic ketones, aliphatic carboxylic acid esters, aliphatic carboxylic acid amides, aromatic hydrocarbons, aliphatic hydrocarbons, acetonitrile, aliphatic sulfoxides, sorbitol.
  • the content of the solvent of the present invention is preferably 50 to 99.9 parts by weight, more preferably 60 to 99 parts by weight based on 100 parts by weight of the conductive composition.
  • the solvent of the present invention is added to disperse the conductive polymer on the solution.
  • the content of the solvent is less than 50 parts by weight, the dispersibility of the conductive polymer is inferior, which may cause a problem of resistance scattering.
  • the amount is exceeded, there is a problem that the electrical conductivity of the conductive polymer composition is reduced.
  • the conductive polymer composition according to the present invention may further include a second dopant.
  • the second dopant exhibits a screen effect between the conductive polymer and the polycellulose sulfonate to separate the polycellulose sulfonate having a low electrical conductivity from the conductive polymer, thereby improving the electrical conductivity of the conductive polymer composition as a whole.
  • the second dopant is only referred to as a secondary dopant because it causes a structural change of the conductive polymer and does not remain as a dopant, but exhibits the same effect as doping.
  • the second dopant is preferably an organic compound containing oxygen and nitrogen, and specifically, may be an ether group compound, a carbonyl group compound, a polar solvent, or a mixture thereof.
  • the compound containing the ether group diethylene glycol monoethyl ether and the like are preferable, and as the compound containing the carbonyl group, isoprone, propylene carbonate, cyclohexanone or butyrolactone is preferable.
  • the polar solvent at least one selected from dimethyl sulfoxide, N-methylpyrrolidone, N, N-dimethylformamide, N-dimethylacetimide and sorbitol is preferable.
  • At least one selected from dimethyl sulfoxide, N-methylpyrrolidone, N, N-dimethylformamide, N-dimethylacetimide and sorbitol as the second dopant in terms of electrical conductivity improvement is used. desirable.
  • the content of the second dopant is preferably 0.5 to 15 parts by weight, and more preferably 0.5 to 5 parts by weight based on 100 parts by weight of the conductive polymer composition of the present invention. If the content of the second dopant is less than 0.5 parts by weight, there is little effect of improving the electrical conductivity, and if it exceeds 10 parts by weight, it is uneconomical because there is no effect of improving the conductivity due to the addition.
  • the conductive composition of the present invention may further include a binder.
  • the binder increases adhesion when the conductive polymer composition is applied to the base member.
  • the binder may be at least one selected from acrylic, epoxy, ester, cellulose, urethane, ether, carboxyl, and amide based.
  • the content of the binder is preferably 0.1 to 10 parts by weight, more preferably 0.5 to 8 parts by weight with respect to 100 parts by weight of the conductive composition of the present invention.
  • the content of the binder is less than 0.1 parts by weight, the effect of improving adhesion is insignificant, and when the content of the binder is more than 10 parts by weight, the content is relatively higher than that of the conductive polymer, thereby reducing the electrical conductivity.
  • the conductive polymer composition according to the present invention may further include other additives such as dispersion stabilizers and surfactants in addition to the above additives.
  • the method for preparing a conductive composition of the present invention includes the steps of preparing a conductive polymer monomer solution comprising (A) a conductive polymer monomer, a polycellulose sulfonate and a solvent, and (B) polymerizing the conductive polymer monomer solution. It features.
  • a conductive polymer monomer solution comprising (A) a conductive polymer monomer, a polycellulose sulfonate and a solvent, and (B) polymerizing the conductive polymer monomer solution.
  • a conductive polymer monomer solution containing a conductive polymer monomer, a polycellulose sulfonate and a solvent is prepared.
  • the conductive polymer monomer may be thiophene, aniline, pyrrole, acetylene, phenylene or derivatives thereof.
  • the conductive polymer monomer may be 3,4-ethylenedioxythiophene.
  • Poly (3,4-ethylenedioxythiophene) polymerized with the conductive polymer monomer 3,4-ethylenedioxythiophene has the advantage of high electrical conductivity and excellent transmittance.
  • the content of the conductive polymer monomer is preferably 0.1 to 20 parts by weight, more preferably 0.1 to 3 parts by weight of 100 parts by weight of the conductive polymer monomer solution. If the content of the conductive polymer monomer is less than 0.1 parts by weight, there is a problem that the electrical conductivity of the conductive polymer composition is low, if it exceeds 20 parts by weight, the transmittance of the conductive polymer composition is lowered, the problem is not easy processing There is.
  • the conductive polymer monomer solution of the present invention includes a polycellulose sulfonate as a dopant, and the present invention enables the production of a conductive polymer doped with polycellulose sulfonate by using the polycellulose sulfonate as a dopant in the polymerization of the conductive polymer monomer. do.
  • the conductive polymer composition of the present invention doped with polycellulose sulfonate has excellent electrical conductivity with a sheet resistance of 500 ⁇ / ⁇ or less, and has high stability due to less change in molecular structure due to heat.
  • the content of the polycellulose sulfonate is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 6 parts by weight of 100 parts by weight of the conductive polymer monomer solution.
  • the content of the polycellulose sulfonate is less than 0.01 part by weight, the solubility of the conductive polymer is lowered and the doping effect of the conductive polymer is low.
  • the content of the polycellulose sulfonate is more than 10 parts by weight, the electrical conductivity improvement effect is increased by the addition of the polycellulose sulfonate. Insignificant
  • the solvent of the present invention serves to dissolve and disperse the conductive polymer monomer and the polycellulose sulfonate.
  • the solvent includes 40 to 99 parts by weight of 100 parts by weight of the conductive polymer monomer solution.
  • (B) the conductive polymer monomer solution is polymerized.
  • a conductive polymer doped with polycellulose sulfonate can be obtained.
  • Chemical polymerization, electrochemical polymerization, thermal polymerization, photopolymerization, and the like may be used as a method of polymerizing the conductive polymer monomer solution.
  • oxidizing agents such as ammonium peroxydisulfate, hydrochloric acid, and Lewis acid are added to the conductive polymer monomer solution to easily oxidize the monomer, and then polymerize to the conductive polymer.
  • the oxidizing agent is preferably added 0.0001 ⁇ 4 mol relative to 1 mol of the conductive polymer monomer.
  • oxidizing agent Fe 2 (SO 4 ) 3 5H 2 O was added to the conductive polymer monomer solution, followed by oxidative polymerization at 25 ° C. for 3 hours to give poly (3,4-ethylenedioxythiophene) / poly Cellulosesulfonate (PEDOT / PCS) conductive polymer compositions were prepared.
  • the conductive polymer composition was coated on a base member and dried in an oven at 100 ° C. for 2 minutes to prepare a conductive film.
  • the composition ratio of the conductive polymer monomer solution is different from 96.5 parts by weight of water, 1 part by weight of 3,4-ethylenedioxythiophene, and 2.5 parts by weight of polycellulose sulfonate based on 100 parts by weight of the conductive polymer monomer solution. It was.
  • the conductive polymer composition was coated on the base member and dried in an oven at 100 ° C. for 2 minutes to prepare a conductive film.
  • the composition ratio of the conductive polymer monomer solution is different from 94 parts by weight of water, 1 part by weight of 3,4-ethylenedioxythiophene, and 5 parts by weight of polycellulose sulfonate based on 100 parts by weight of the conductive polymer monomer solution. It was.
  • the conductive polymer composition was coated on the base member and dried in an oven at 100 ° C. for 2 minutes to prepare a conductive film.
  • the composition ratio of the conductive polymer monomer solution is different from 93 parts by weight of water, 1 part by weight of 3,4-ethylenedioxythiophene, and 6 parts by weight of polycellulose sulfonate based on 100 parts by weight of the conductive polymer monomer solution. It was.
  • the conductive polymer composition was coated on the base member and dried in an oven at 100 ° C. for 2 minutes to prepare a conductive film.
  • polystyrene sulfonate was added instead of polycellulose sulfonate as a dopant.
  • the composition ratio of the conductive polymer monomer solution was 96.5 parts by weight of water, 1 part by weight of 3,4-ethylenedioxythiophene, and 2.5 parts by weight of polystyrenesulfonate based on 100 parts by weight of the conductive polymer monomer solution.
  • the conductive polymer composition was coated on the base member and dried in an oven at 100 ° C. for 2 minutes to prepare a conductive film.
  • polystyrene sulfonate was added instead of polycellulose sulfonate as a dopant.
  • the composition ratio of the conductive polymer monomer solution was 97 parts by weight of water, 1 part by weight of 3,4-ethylenedioxythiophene, and 6 parts by weight of polystyrenesulfonate based on 100 parts by weight of the conductive polymer monomer solution.
  • the conductive polymer composition was coated on the base member and dried in an oven at 100 ° C. for 2 minutes to prepare a conductive film.
  • the sheet resistance of the conductive films prepared from the conductive polymer compositions of Examples and Comparative Examples before and after the heat treatment was evaluated and shown in Table 1 below.
  • Table 1 For sheet resistance, Mitsubishi Chemical Corporation's Loresta EP MCP-T360 was used. Heat treatment was performed for 30 minutes in 150 degreeC oven.
  • the conductive polymer poly (3,4-ethylenedioxythiophene) / polycellulose sulfonate (PEDOT / PCS) doped with polycellulose sulfonate is poly (3,4- It was found that the lower the sheet resistance value than ethylenedioxythiophene) / polystyrene sulfonate (PEDOT / PSS), the better the electrical conductivity. In addition, it was confirmed that the conductive polymer poly (3,4-ethylenedioxythiophene) / polycellulose sulfonate of the present invention had low dispersion (%) of sheet resistance values before and after heat treatment, and thus had excellent thermal stability.
  • the crosslinking density between the conductive polymers is increased, thereby improving the electrical conductivity.
  • the stability of the molecular structure of the entire composition is increased, there is an effect that the width of change in electrical conductivity due to heat is reduced.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Conductive Materials (AREA)

Abstract

La présente invention concerne une composition polymère conductrice et un procédé de préparation de ladite composition, et, plus particulièrement, une composition conductrice et un procédé de fabrication de ladite composition, la composition conductrice ayant une conductivité électrique supérieure et une stabilité supérieure, en raison de la densité de réticulation accrue de poly(3,4-éthylènedioxythiophène) par l'addition de poly(sulfonate de cellulose) comme dopant dans le poly(3,4-éthylènedioxythiophène).
PCT/KR2011/007547 2011-08-26 2011-10-11 Composition conductrice et son procédé de fabrication WO2013032059A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201180072978.3A CN103764766A (zh) 2011-08-26 2011-10-11 传导性组合物及其制备方法

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KR10-2011-0086077 2011-08-26
KR1020110086077A KR101289768B1 (ko) 2011-08-26 2011-08-26 전도성 조성물 및 이의 제조방법

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KR102616814B1 (ko) 2018-03-09 2023-12-21 삼성전자주식회사 반도체 패키지 및 반도체 모듈
KR102705039B1 (ko) 2018-12-28 2024-09-10 삼성전자주식회사 접착 필름, 이를 이용한 반도체 장치, 및 이를 포함하는 반도체 패키지
KR102318048B1 (ko) * 2019-09-16 2021-10-28 한국원자력연구원 전기전도성 셀룰로오스 복합체 제조 방법 및 이에 의해 제조된 전기전도성 셀룰로오스 복합체

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US20060144543A1 (en) * 2003-04-01 2006-07-06 Outi Aho Process for producing a fibrous composition
US7943066B2 (en) * 2006-10-06 2011-05-17 The University Of New Brunswick Electrically conductive paper composite

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JP5771873B2 (ja) * 2006-05-04 2015-09-02 エルジー・ケム・リミテッド 伝導性（導電性）高分子複合体を用いた高容量／高出力の電気化学エネルギー貯蔵素子

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KR100442408B1 (ko) * 1998-11-05 2004-11-06 제일모직주식회사 고전도성및고투명성을갖는폴리티오펜계전도성고분자용액조성물
KR100437198B1 (ko) * 2001-02-23 2004-06-23 장관식 높은 용해성을 갖는 수용성 폴리피롤 및 그것의 제조방법
US20060144543A1 (en) * 2003-04-01 2006-07-06 Outi Aho Process for producing a fibrous composition
US7943066B2 (en) * 2006-10-06 2011-05-17 The University Of New Brunswick Electrically conductive paper composite

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CN103764766A (zh) 2014-04-30
KR20130022982A (ko) 2013-03-07
KR101289768B1 (ko) 2013-07-26

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