WO2014014262A2 - Composition conductrice organique - Google Patents

Composition conductrice organique Download PDF

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Publication number
WO2014014262A2
WO2014014262A2 PCT/KR2013/006379 KR2013006379W WO2014014262A2 WO 2014014262 A2 WO2014014262 A2 WO 2014014262A2 KR 2013006379 W KR2013006379 W KR 2013006379W WO 2014014262 A2 WO2014014262 A2 WO 2014014262A2
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WIPO (PCT)
Prior art keywords
conductive composition
organic conductive
organic
composition
tert
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PCT/KR2013/006379
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English (en)
Korean (ko)
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WO2014014262A3 (fr
Inventor
이정훈
김선영
김병욱
최경희
Original Assignee
주식회사 동진쎄미켐
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Priority to CN201380033354.XA priority Critical patent/CN104380390A/zh
Publication of WO2014014262A2 publication Critical patent/WO2014014262A2/fr
Publication of WO2014014262A3 publication Critical patent/WO2014014262A3/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • 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
    • 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
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B5/00—Non-insulated conductors or conductive bodies characterised by their form
    • H01B5/14—Non-insulated conductors or conductive bodies characterised by their form comprising conductive layers or films on insulating-supports
    • 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
    • C08G2261/70—Post-treatment
    • C08G2261/79—Post-treatment doping
    • C08G2261/794—Post-treatment doping with polymeric dopants

Definitions

  • the present invention relates to an organic conductive composition, and more particularly to the problem of the conventional organic conductive composition is difficult to maintain stable physical properties due to the oxidizable properties of the conductive polymer is a mixture of a specific binder and the primary and secondary antioxidants It relates to an organic conductive composition that greatly improved the oxidation stability of the organic conductive composition comprising a conductive polymer through.
  • Organic conductive compositions are widely used in various fields.
  • the functional layer is required for the IT device including various display devices with the rapid growth of the IT field
  • the organic conductive composition is attracting more attention because of the advantage of easily forming a thin film layer having required physical properties such as conductivity.
  • organic conductive compositions include conductive polymers.
  • the conductive polymer is oxidized through the mechanism as shown in FIG. 1, and thus the composition has a problem in that the stability is largely weak.
  • the organic conductive composition is deteriorated faster in an environment of a hot plate (80 ° C.) that only heats in the atmosphere than an environment of high temperature and high humidity (80 ° C. and 90% humidity) supplied with moisture. have.
  • the smallest deterioration in the vacuum oven environment indicates that the supply of oxygen is the most important factor of deterioration.
  • an object of the present invention is to provide an organic conductive composition that significantly improves the oxidation stability and conductivity of the organic conductive composition is difficult to maintain stable physical properties due to the oxidizable properties of the conductive polymer.
  • an object of the present invention is to provide a method for forming a conductive thin film using an organic conductive composition that significantly improves the oxidation stability and conductivity, the conductive thin film formed by the method, and an IT device including the thin film.
  • the present invention provides a method for forming a conductive thin film comprising the step of applying the organic conductive composition on a substrate, a conductive thin film formed by the method, and an IT device comprising the conductive thin film.
  • the organic conductive composition of the present invention includes a conductive polymer through a mixed use of a specific binder and a primary and a secondary antioxidant, which is difficult to maintain stable physical properties due to the oxidizable property of the conductive polymer. Oxidation stability of the organic conductive composition can be greatly improved.
  • Figure 2 shows the change in sheet resistance according to the storage environment of the conductive composition using PEDOT
  • Example 3 shows changes in sheet resistance of Example 1 and Comparative Examples 1-4 of the present invention.
  • the organic conductive composition of the present invention is a primary antioxidant selected from the group consisting of (a) conductive polymers, (b) dopants, (c) silane coupling agents, and (d) phenol derivative compounds, (e) It is characterized by including a secondary antioxidant selected from the group consisting of phosphorus compounds or sulfur compounds and (f) a residual amount of solvent.
  • the conductive polymer used in the present invention has a basic function of making the organic conductive composition conductive.
  • the conductive polymer is not particularly limited as long as it is a conductive polymer that can be generally used in an organic conductive composition, and examples thereof include polyaniline, polypyrrole, polythiophene and derivatives or analogs thereof of the monomers (aniline, pyrrole and thiophene).
  • polymerized by the monomer is mentioned, More specifically, the poly (3, 4- ethylene dioxythiophene) superposed
  • the amount of the conductive polymer used in the present invention is preferably 0.1-10% by weight of the organic conductive composition.
  • the content of the conductive polymer is less than 0.1% by weight, it is difficult for the organic conductive composition to exhibit conductivity, and when the content of the conductive polymer is greater than 10% by weight, dispersibility becomes poor, which makes processing difficult.
  • the dopant used in the present invention may be used without particular limitation as long as it is a conductive polymer that can be used in an organic conductive composition.
  • Acrylamido-2-methylpropanesulfonic acid and its respective salt compounds, 2-sulfosuccinic acid ester salts, sodium 5-sulfoisophthalic acid, dimethyl-5-sodium sulfoisophthalate or 5-sodiumsulfo-bis ( ⁇ - Hydroxyethyl) isophthalate is mentioned,
  • the said dopant can be used individually or in mixture of 2 or more types.
  • the amount of the dopant used in the present invention is preferably 0.1-40% by weight of the organic conductive composition.
  • the content of the dopant is more preferably 100 to 400 parts by weight based on 100 parts by weight of the conductive polymer in terms of conductivity.
  • the organic conductive composition of the present invention contains a silane coupling agent.
  • the silane coupling agent functions to improve dispersibility and oxidative stability of the conductive polymer.
  • As the silane coupling agent for example, an alkyloxy silane compound, an amino silane compound, a vinyl silane compound, an epoxy silane compound, a methacryloxy silane compound, an isocyanate silage compound or a fluorine silane compound may be used.
  • the said silane coupling agent can be used individually or in mixture of 2 or more types.
  • the amount of the silane coupling agent used in the present invention is preferably 3-90% by weight of the organic conductive composition. When in the above range can be satisfied at the same time the dispersibility and oxidation stability of the conductive polymer in the organic conductive composition.
  • the organic conductive composition of the present invention comprises (d) at least one primary antioxidant selected from the group consisting of phenol derivative compounds and (e) at least one secondary antioxidant selected from the group consisting of phosphorus compounds or sulfur compounds. Include.
  • the organic conductive composition of the present invention is a primary antioxidant and a secondary antioxidant
  • the primary antioxidant which is a phenol derivative compound
  • the primary antioxidant may be used alone or in mixture of two or more kinds.
  • the phenol derivative simple phenolics, bisphenolics, polyphenolics, thiobisphenolics may be used.
  • examples of the phenol derivatives include 2,6-di-tert-butyl-p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, stearyl (3,5-di-tert) -Butyl-4-hydroxyphenyl) propionate, distearyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphate, thiodiethylene glycol bis [(3,5-di-3 Tert-butyl-4-hydroxyphenyl) propionate], 1,6-hexamethylene bis [(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 1,6- Hexamethylene bis [(3,5-di-tert-butyl-4-hydroxyphenyl) propionamide], 4,4'-thiobis (6-tert-butyl-m-cresol), 2,2 ' Methylene bis (4-methyl-6-tert-butylphenol), 2,2'-methylenebis
  • the Bisphenolics / Polyphenolics is preferably used in combination with simple phenolics in order to obtain optimum processability due to low volatility and relatively low equivalent weight due to high molecular weight compared to simple phenolics, and 8-Hydroxyquinoline, 8 as polyphenolics antioxidant -Hydroxyquinoline sulfate, 8-Hydroxyquinoline-5-sulfonic acid, Tetrakis (methylene-3.5-di-t-butyl-4-hydroxyhydrocinnamate) methane can be used.
  • At least one secondary antioxidant selected from the group consisting of phosphorus compounds or sulfur compounds may be used alone or in combination of two or more thereof, and the secondary antioxidant may be used for the decomposition of hydroperoxide. Acts to prevent diffusion of alkoxy and hydroxy radicals.
  • Examples of the phosphorus antioxidant include tris (nonylphenyl) phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tris [2-tert-butyl-4- (3-tert-butyl) -4-hydroxy-5-methylphenylthio) -5-methylphenyl] phosphite, tridecylphosphite, octyldiphenylphosphite, di (decyl) monophenylphosphite, monodecyldiphenylphosphite, mono (dinonyl Phenyl) bis (nonylphenyl) phosphite, di (tridecyl) pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, di (nonylphenyl) pentaerythritol diphosphite
  • sulfur-based antioxidant examples include Methimazole (mesimiazole), dialkyldithiopropionate [dilaurylthiopropionate, dimyristylthiopropionate or distearylthiopropionate], ⁇ -al of polyol Chelmercaptopropionic acid esters (tetra ( ⁇ -dodecylmercaptopropionate) of pentaerythritol).
  • the amount of the primary antioxidant and the secondary antioxidant in the organic conductive composition of the present invention is 5-10000 ppm (0.005-1 wt%) each independently. If less than 5 ppm oxidative stability does not exhibit the effect as desired, if more than 10000 ppm may lower the conductivity of the organic conductive composition.
  • the organic conductive composition of the present invention includes a solvent (f), and is included in the remaining amount except for the components of (a) to (e) described above, and is not particularly limited as long as it is a solvent usually used in the organic conductive composition.
  • No water Alcohols and diols, polyol methyl alcohol, ethyl alcohol, isopropyl alcohol, ethylene glycol, butanediol, neopentyl glycol, 1,3-pentanediol, 1,4-cyclohexanedimethanol, diethylene glycol, polyethylene glycol, polybutylene Prepared by esterification of one or more alcohols, diols or polyols selected from the group consisting of monomers or derivatives thereof consisting of glycol, dimethylolpropane and trimethylolpropane; Halogens such as chloroform, dichloromethane, tetrachloroethylene, trichloroethylene, dibromoethane and dibrom
  • organic conductive composition of the present invention may further include a surfactant and other additives that may be added to the organic conductive composition, in addition to the above components.
  • the present invention provides a method for forming a conductive thin film comprising the step of applying the organic conductive composition on a substrate, a conductive thin film formed by the method, and an IT device comprising the conductive thin film
  • the method of applying in the above Silver may be generally applied to the spray method, bar coating method, doctor blade method, roll coating method, dipping method and the like to apply the organic conductive composition on a substrate, and known steps that are generally applied to the formation of a conductive thin film
  • known steps that are generally applied to the formation of a conductive thin film Of course it can include.
  • the organic conductive composition is coated on the substrate to a thickness of 5-20 ⁇ m using a spray method, a bar coating method, a doctor blade method, or a roll coating method, and soft baked for 180 seconds on a 110 ° C. hot plate. After forming a film layer of 100-300 nm and dried for 10 minutes in an oven at 120 °C to form a conductive thin film on the substrate.
  • the conductive thin film When the conductive thin film is formed using the organic conductive composition of the present invention as described above, the conductive thin film can be formed with high reliability so as to have stable physical properties, and the formed thin film is also more conductive and durable than the thin film manufactured by using the conventional organic conductive composition. And it is useful in manufacturing a reliable IT device with excellent oxidation stability.
  • PEDOT PSS (poly 3,4-ethylenedioxythiophene: polystyrenesulfonate, weight ratio: 1: 2.5, Concentration of 1.6% by weight) 5% by weight of aqueous dispersion, 10% by weight of TEOS (tetraethyloxysilane), 1% by weight of acetic acid, 1000 ppm of surfactant, 30% by weight of Ethyleneglycol, and the remainder of IPA (isopropyl alcohol). ), An organic conductive composition was prepared.
  • An organic conductive composition was prepared by adding 0.02% by weight of Methylgallate (methylgallate), which is a primary oxidative stabilizer, to Comparative Example 1.
  • An organic conductive composition was prepared by adding 0.02% by weight of a second oxidation stabilizer, Methimazole (mesimiazole), to Comparative Example 1.
  • An organic conductive composition was prepared by adding 0.06% by weight of Methylgallate (methylgallate) as a primary oxidation stabilizer to Comparative Example 1.
  • an organic conductive composition was prepared by adding 0.02% by weight of a primary oxidative stabilizer, Methyl gallate (methyl gallate) and 0.02% by weight of a secondary oxidative stabilizer, Methimazole (mesimiazole).
  • Example 3 The change in sheet resistance of the organic conductive compositions prepared in Example 1 and Comparative Examples 1-4 was measured (measured by Simco's ST-4) and is shown in FIG. 3. As shown in FIG. 3, Comparative Example 2-3 using antioxidant alone compared to Comparative Example 1 showed some antioxidant effect, even when the primary antioxidant content was increased three times (Comparative Example 4). Although the improvement effect is not large, when the primary antioxidant and the secondary antioxidant are used together as in Example 1, it can be seen that the effect is dramatically improved.
  • the organic conductive composition of the present invention includes a conductive polymer through a mixed use of a specific binder and a primary and a secondary antioxidant, which is difficult to maintain stable physical properties due to the oxidizable property of the conductive polymer. Oxidation stability of the organic conductive composition can be greatly improved.

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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)

Abstract

La présente invention concerne une composition conductrice organique, et de façon plus spécifique, une composition conductrice organique comprenant (a) un polymère conducteur, (b) un dopant, (c) un agent de couplage silane ; (d) un ou plusieurs premiers antioxydants choisis dans le groupe consistant en composés dérivés à base de phénol, (e) un ou plusieurs seconds antioxydants choisis dans le groupe consistant en composés à base de phosphore et composés à base de soufre ; et (f) un solvant. Il est difficile de maintenir des propriétés physiques stables par l'utilisation d'une composition conductrice organique classique à cause de la vulnérabilité d'un polymère conducteur à l'oxydation, mais la composition conductrice organique de la présente invention peut grandement améliorer la stabilité à l'oxydation d'une composition conductrice organique contenant un polymère conducteur par mélange d'un liant spécifique et des premier et second antioxydants.
PCT/KR2013/006379 2012-07-20 2013-07-17 Composition conductrice organique WO2014014262A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201380033354.XA CN104380390A (zh) 2012-07-20 2013-07-17 有机导电性组合物

Applications Claiming Priority (2)

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KR10-2012-0079599 2012-07-20
KR1020120079599A KR102026446B1 (ko) 2012-07-20 2012-07-20 유기 도전성 조성물

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WO2014014262A2 true WO2014014262A2 (fr) 2014-01-23
WO2014014262A3 WO2014014262A3 (fr) 2014-03-13

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TW (1) TWI620201B (fr)
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CN106459638A (zh) * 2014-05-27 2017-02-22 株式会社Lg化学 导电聚合物油墨组合物
EP3354689A1 (fr) * 2017-01-30 2018-08-01 Heraeus Deutschland GmbH & Co. KG Composition pour la formation d'une couche anti-statique ou d'un blindage contre les radiations électromagnétiques

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106459638A (zh) * 2014-05-27 2017-02-22 株式会社Lg化学 导电聚合物油墨组合物
CN106459638B (zh) * 2014-05-27 2019-04-26 株式会社Lg化学 导电聚合物油墨组合物
EP3354689A1 (fr) * 2017-01-30 2018-08-01 Heraeus Deutschland GmbH & Co. KG Composition pour la formation d'une couche anti-statique ou d'un blindage contre les radiations électromagnétiques
WO2018137934A1 (fr) * 2017-01-30 2018-08-02 Heraeus Deutschland Gmbh & Co Kg Compositions utiles pour la formation d'une couche antistatique ou d'un blindage contre le rayonnement électromagnétique
JP2020506986A (ja) * 2017-01-30 2020-03-05 ヘレウス ドイチェラント ゲーエムベーハー ウント カンパニー カーゲー 帯電防止層または電磁放射線遮蔽の形成に有用な組成物
US11078326B2 (en) 2017-01-30 2021-08-03 Heraeus Deutschland GmbH & Co. KG Compositions useful for the formation of an antistatic layer or an electromagnetic radiation shield
JP6998962B2 (ja) 2017-01-30 2022-01-18 ヘレウス ドイチェラント ゲーエムベーハー ウント カンパニー カーゲー 帯電防止層または電磁放射線遮蔽の形成に有用な組成物

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KR102026446B1 (ko) 2019-09-27
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KR20140012509A (ko) 2014-02-03
WO2014014262A3 (fr) 2014-03-13

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