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  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
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  • 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
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  • C08G61/126—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 with a five-membered ring containing one sulfur atom in the ring
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  • C08L25/02—Homopolymers or copolymers of hydrocarbons
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  • C09D125/00—Coating compositions based on 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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
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  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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  • C09D7/65—Additives macromolecular
• • H—ELECTRICITY
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  • 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
  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/0029—Processes of manufacture
  • H01G9/0036—Formation of the solid electrolyte layer
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/004—Details
  • H01G9/022—Electrolytes; Absorbents
  • H01G9/025—Solid electrolytes
  • H01G9/028—Organic semiconducting electrolytes, e.g. TCNQ
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/15—Solid electrolytic capacitors
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/10—Organic polymers or oligomers
  • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
  • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
  • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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  • 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
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  • C08G2261/70—Post-treatment
  • C08G2261/79—Post-treatment doping
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  • H10K10/10—Organic capacitors or resistors having potential barriers

Definitions

• Solid electrolytic capacitors are used in electronic devices because they can reduce equivalent series resistance (ESR) in the high frequency range. Furthermore, with the recent trend towards electrification of cars, development of solid electrolytic capacitors for automotive use is progressing. In particular, for capacitors intended for vehicle electronic control devices, there is a demand for further reduction in ESR in order to increase output through electronic control.
• ESR equivalent series resistance
• a known method for forming a solid electrolyte using a conductive polymer is, for example, to impregnate an electrolytic capacitor element with a monomer solution and an oxidant solution for obtaining a conductive polymer, and then to perform oxidative polymerization or electrolytic polymerization within the electrolytic capacitor element (see, for example, Patent Document 1).
• Patent document 3 also describes an electrolytic capacitor that includes a capacitor element and a liquid component, in which the difference between the Hansen solubility parameter of the self-doped conductive polymer component included in the capacitor element and the liquid component is within a specified numerical range.
• the ESR of the solid electrolytic capacitor is not necessarily sufficiently low. Also, for an electrolytic capacitor containing a self-doped conductive polymer component as described in Patent Document 3, even when a specific value for the Hansen solubility parameter is satisfied, there is still room for a decrease in ESR.
• the present invention has been made in consideration of these circumstances, and aims to provide a conductive polymer-containing dispersion for obtaining a solid electrolytic capacitor with a low ESR, and a method for producing the same. Another aim of the present invention is to provide a solid electrolytic capacitor with a low ESR.
• a conductive polymer-containing dispersion comprising a conjugated conductive polymer (A), a polyanion (B), an additive (C), and a dispersion medium (D), wherein the additive (C) has a hydrogen bond term ⁇ H 1 of the Hansen solubility parameter of 5.0 to 20.0 MPa 0.5 .
• the content of the additive (C) is 1 to 50 parts by mass per part by mass of the total amount of the conjugated conductive polymer (A) and the polyanion (B).
• R 1 and R 2 are each independently a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, or an optionally substituted alkylthio group having 1 to 18 carbon atoms; or, formed by bonding R 1 and R 2 to each other, an optionally substituted alicyclic ring having 3 to 10 carbon atoms, an optionally substituted aromatic ring having 6 to 10 carbon atoms, an optionally substituted oxygen atom-containing heterocyclic ring having 2 to 10 carbon atoms, an optionally substituted sulfur atom-containing heterocyclic ring having 2 to 10 carbon atoms, or an optionally substituted sulfur atom- and oxygen atom-containing heterocyclic ring having 2 to 10 carbon atoms.
• the present invention can provide a conductive polymer-containing dispersion for obtaining a solid electrolytic capacitor with a low ESR and a method for producing the same.
• the present invention also makes it possible to obtain a solid electrolytic capacitor with a low ESR.
• the term “optionally substituted” means that the group may be substituted or may not be substituted (unsubstituted).
• the term “class” attached to the name of a compound means a group of compounds containing the compound structure, including compounds having a substituent.
• polypyrroles refer to a group of compounds containing a polypyrrole structure.
• (Meth)acrylic acid is a general term for acrylic acid and methacrylic acid.
• Hansen solubility parameters are values regarding the solubility of a substance, estimated by calculation based on the molecular structure.
• HSP consists of three parameters: the dispersion term ⁇ D, which represents the energy due to dispersion forces between molecules; the polar term ⁇ P, which represents the energy due to dipole interactions between molecules; and the hydrogen bond term ⁇ H, which represents the energy due to hydrogen bonds between molecules.
• HSP ( ⁇ D, ⁇ P, ⁇ H) was calculated based on the molecular structure (canonical SMILES notation) using the Y-MB method of the DIY program of the software "HSPiP ver. 5.3.04".
• the conductive polymer-containing dispersion of this embodiment may further contain a polymer (E), an alkaline compound (F), and other additives, which will be described later.
• the total content of the conjugated conductive polymer (A), the polyanion (B), the hydroxyl group-containing cyclic ether compound (C), and the dispersion medium (D) in the conductive polymer-containing dispersion is preferably 80 to 100 mass%, more preferably 85 to 100 mass%, and even more preferably 90 to 100 mass%.
• the dispersion does not contain any polymer other than the conjugated conductive polymer (A) and the polyanion (B).
• the total content of the conjugated conductive polymer (A), polyanion (B) and polymer (E) in the conductive polymer-containing dispersion is preferably 0.1 to 20% by mass, more preferably 0.5 to 15% by mass, and even more preferably 1 to 10% by mass, from the viewpoints of the effect of reducing the ESR of the solid electrolytic capacitor, the viscosity of the conductive polymer-containing dispersion that is easy to handle, and the dispersibility of the composite particles (2).
• the conjugated conductive polymer (A) preferably has a substituent such as an alkyl group, a carboxy group, a sulfo group, an alkoxy group, a hydroxyl group or a cyano group.
• polypyrroles include polypyrrole, poly(N-methylpyrrole), poly(3-methylpyrrole), poly(3-ethylpyrrole), poly(3-n-propylpyrrole), poly(3-butylpyrrole), poly(3-octylpyrrole), poly(3-decylpyrrole), poly(3-dodecylpyrrole), poly(3,4-dimethylpyrrole), poly(3,4-dibutylpyrrole), poly(3-carboxypyrrole), poly(3-methyl-4-carboxypyrrole), poly(3-methyl-4-carboxyethylpyrrole), poly(3-methyl-4-carboxybutylpyrrole), poly(3-hydroxypyrrole), poly(3-methoxypyrrole), poly(3-ethoxypyrrole), poly(3-butoxypyrrole), poly(3-hexyloxypyrrole), poly(3-methyl-4-hexy
• the sulfur atom-containing heterocycle preferably has 1 to 3 nitrogen atoms constituting the ring, and examples thereof include a thiirane ring, a thietane ring, a thiophene ring, a thiane ring, a thiopyran ring, a thiopyrylium ring, a benzothiopyran ring, a dithiane ring, a dithiolane ring, and a trithiane ring.
• the heterocycle containing a sulfur atom and an oxygen atom preferably contains 1 to 3 sulfur atoms and oxygen atoms in total, and examples thereof include an oxathiolane ring and an oxathiane ring.
• the monomer that constitutes the conjugated conductive polymer (A) is preferably a compound represented by the following formula (2) among the compounds represented by formula (1), and more preferably contains 3,4-ethylenedioxythiophene.
• the polyanion (B) contained in the conductive polymer-containing dispersion and the polyanion used in the production process of the conductive polymer-containing dispersion may have the same structure or different structures (e.g., different cations are bonded, etc.).
• sodium polystyrene sulfonate is preferably used as the polyanion from the viewpoint of water solubility, etc., and may be converted to polystyrene sulfonic acid by ion exchange or the like in a subsequent desalting process.
• the polyanion (B) can be produced by a known production method, for example, as described in JP-A-2005-76016, or a commercially available product can be used.
• the polymer (E) is preferably obtained as a dispersion containing the polymer (E) dispersed in a dispersion medium, and more preferably in the form of an emulsion.
• the polyanion contributes to the dispersion stability of the dispersion containing polymer (E).
• additives such as emulsifiers and aliphatic amines may be added to the dispersion containing polymer (E) as necessary.
• the type and amount of additives are appropriately adjusted depending on the content and composition of the ethylenically unsaturated monomer and polyanion.
• the emulsifier and aliphatic amine contained in the dispersion containing polymer (E) may be one type alone or two or more types.
• alkali metal alkoxides examples include sodium alkoxides such as sodium methoxide and sodium ethoxide; potassium alkoxides; calcium alkoxides, etc.
• water-soluble polymeric compound examples include polyoxyalkylenes, water-soluble polyurethanes, water-soluble polyesters, water-soluble polyamides, water-soluble polyimides, water-soluble polyacrylics, water-soluble polyacrylamides, polyvinyl alcohols, polyacrylic acids, etc.
• polyoxyalkylenes are preferred.
• the monomers that are the constituent units of the conjugated conductive polymer (A) are dissolved, emulsified or dispersed in the raw material liquid (1).
• the raw material liquid (1) can be prepared, for example, by stirring with a stirrer such as a homomixer or homogenizer, or by ultrasonic irradiation, etc.
• the polymerization reaction for synthesizing the conjugated conductive polymer (A) is preferably carried out in the presence of an oxidizing agent.
• the oxidizing agent include peroxodisulfuric acid, peroxodisulfate salts such as ammonium peroxodisulfate, sodium peroxodisulfate, and potassium peroxodisulfate; metal halide compounds such as boron trifluoride; transition metal compounds such as iron chloride (III), iron sulfate (III), and copper chloride (II); metal oxides such as silver oxide and cesium oxide; peroxides such as hydrogen peroxide and ozone; organic peroxides such as benzoyl peroxide; and oxygen.
• the method for producing the solid electrolytic capacitor of the present embodiment includes a step of depositing the conductive polymer-containing dispersion of the present embodiment described above onto a porous anode body made of a valve metal having a dielectric coating on its surface, and then removing the dispersion medium (D) from the dispersion liquid deposited on the porous anode body to form a solid electrolyte layer.
• a solid electrolyte layer using the conductive polymer-containing dispersion liquid of this embodiment through such a process, a solid electrolytic capacitor having a low ESR can be suitably manufactured.
• Example 7 In a 1 L polyethylene container, 63.0 g of a 12 mass % aqueous solution of sodium polystyrene sulfonate (7.56 g of sodium polystyrene sulfonate) and 225.7 g of pure water were mixed with stirring at 32° C. To this, 2.80 g of 3,4-ethylenedioxythiophene was added, and emulsified and mixed for 30 minutes in a homomixer to prepare a raw material liquid (1-2) (total content of sodium polystyrene sulfonate: 2.0 mol of sodium sulfonate groups per 1 mol of 3,4-ethylenedioxythiophene). In Example 1, the raw material liquid (1-1) was changed to the raw material liquid (1-2), and the steps after the step of producing the conjugated conductive polymer (A1) were carried out in the same manner as in Example 1 to produce a conductive polymer-containing dispersion.

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• 2023
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  • 2023-12-18 CN CN202380083748.XA patent/CN120303353A/zh active Pending
  • 2023-12-18 KR KR1020247027629A patent/KR20240131455A/ko not_active Withdrawn
  • 2023-12-18 WO PCT/JP2023/045174 patent/WO2024135579A1/ja not_active Ceased
  • 2023-12-18 KR KR1020257019117A patent/KR20250102098A/ko active Pending
  • 2023-12-18 US US18/839,518 patent/US12278061B1/en active Active
  • 2023-12-18 EP EP23906940.4A patent/EP4640769A1/en active Pending
  • 2023-12-18 CN CN202380022921.5A patent/CN118742614A/zh active Pending
  • 2023-12-20 TW TW112149653A patent/TW202432697A/zh unknown
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