WO2016125618A1 - Composition de solvant pour la fabrication d'un dispositif électronique - Google Patents

Composition de solvant pour la fabrication d'un dispositif électronique Download PDF

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Publication number
WO2016125618A1
WO2016125618A1 PCT/JP2016/052068 JP2016052068W WO2016125618A1 WO 2016125618 A1 WO2016125618 A1 WO 2016125618A1 JP 2016052068 W JP2016052068 W JP 2016052068W WO 2016125618 A1 WO2016125618 A1 WO 2016125618A1
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Prior art keywords
electronic device
solvent
ink
formula
solvent composition
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PCT/JP2016/052068
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English (en)
Japanese (ja)
Inventor
鈴木陽二
坂西裕一
赤井泰之
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株式会社ダイセル
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Priority to JP2016573286A priority Critical patent/JP6652509B2/ja
Publication of WO2016125618A1 publication Critical patent/WO2016125618A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G4/00—Fixed capacitors; Processes of their manufacture
    • H01G4/002—Details
    • H01G4/228—Terminals
    • H01G4/232—Terminals electrically connecting two or more layers of a stacked or rolled capacitor
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G4/00—Fixed capacitors; Processes of their manufacture
    • H01G4/30—Stacked capacitors
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/09—Use of materials for the conductive, e.g. metallic pattern

Definitions

  • the present invention relates to a solvent composition used in an ink for forming a wiring or an electrode using a printing method in the production of an electronic device.
  • This application claims the priority of Japanese Patent Application No. 2015-019637 for which it applied to Japan on February 3, 2015, and uses the content here.
  • Electronic devices manufactured using the printing method include capacitors, inductors, varistors, thermistors, transistors, speakers, actuators, antennas, solid oxide fuel cells, and the like.
  • a multilayer ceramic capacitor is generally manufactured through the following steps. 1.
  • a green sheet is obtained by forming a slurry containing ceramic powder, a binder resin such as polyvinyl acetal resin, and a solvent into a sheet.
  • An ink containing an electrical property imparting material for example, nickel, palladium, etc.
  • a binder resin for example, ethyl cellulose, etc.
  • an organic solvent for example, terpineol, etc.
  • the applied ink is dried (drying process). 4).
  • a green sheet on which wiring or the like is formed is cut into a predetermined size, and a plurality of sheets are stacked and pressed. 5. Firing (firing process).
  • the binder resin contained in the ink has a function of fixing the electrical property imparting material on the green sheet and a function of imparting an appropriate viscosity to enable formation of a fine print pattern.
  • ethyl cellulose has been mainly used as the binder resin.
  • a member having a surface to be coated hereinafter sometimes referred to as a “surface to be coated”
  • the carbon component remains ash after firing, which causes a decrease in conductivity.
  • Patent Document 1 discloses that the amount of ash produced can be reduced by using polyvinyl acetal resin instead of ethyl cellulose. However, even if a polyvinyl acetal resin was used, satisfactory results were not obtained for these problems.
  • an object of the present invention is a solvent composition used for ink for forming wiring and electrodes of electronic devices by a printing method, which can improve the printing accuracy of the ink and can be baked at a low temperature. It is possible to provide a solvent composition capable of suppressing the amount of ash generated after firing extremely low.
  • Another object of the present invention is an ink for forming wiring and electrodes of an electronic device by a printing method, which is excellent in printing accuracy, can be fired at a low temperature, and has an extremely small amount of ash generated after firing, And a manufacturing method thereof.
  • the present inventors have found that the compound represented by the following formula (1) self-assembles and forms a string-like aggregate when heated and dissolved in a solvent. It has been found that such a viscosity is produced, that it can be fired at a lower temperature than a binder resin such as ethyl cellulose, and that the residual amount of ash after firing is extremely small.
  • the ink obtained through the step of heating and dissolving the compound represented by the above formula (1) and the solvent has a viscosity suitable for the formation of wiring and the like by the printing method, so that dripping is suppressed and highly accurate.
  • a wiring pattern can be formed, and in the baking process, baking can be performed quickly at a lower temperature than in the case of baking an ink containing a binder resin such as ethyl cellulose. It has been found that it can be prevented from being softened and deformed by exposure, the residual amount of ash after firing can be remarkably reduced, and the deterioration of electrical characteristics caused by this can be suppressed.
  • the present invention has been completed based on these findings.
  • this invention is a solvent composition used for the ink for manufacturing an electronic device by a printing method, Comprising: A solvent and following formula (1) (In the formula, R represents an aliphatic hydrocarbon group having 1 or more carbon atoms. In the formula, all four Rs are the same group or two different groups.)
  • the solvent composition for electronic device manufacture containing the compound represented by these is provided.
  • the present invention also provides the above-mentioned solvent composition for producing an electronic device, wherein R in the formula (1) is a linear or branched alkyl group, alkenyl group, or alkynyl group having 6 to 18 carbon atoms. To do.
  • the present invention also provides the above-mentioned solvent composition for producing an electronic device, wherein the SP value [(cal / cm 3 ) 0.5 ] at 25 ° C. of the solvent is 7.0 to 9.0.
  • the solvent is n-decane, n-dodecane, propylene glycol methyl-n-propyl ether, propylene glycol methyl-n-butyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl-n-propyl ether, At least selected from the group consisting of propylene glycol methyl-n-butyl ether, dipropylene glycol methyl isoamyl ether, tripropylene glycol methyl-n-propyl ether, cyclohexyl acetate, 2-methylcyclohexyl acetate, and 4-t-butylcyclohexyl acetate
  • One of the above-mentioned solvent compositions for producing an electronic device is provided.
  • the present invention also provides the above-mentioned solvent composition for producing an electronic device, wherein the content of the compound represented by the formula (1) is 0.1 to 50 parts by weight with respect to 100 parts by weight of the solvent.
  • the present invention also provides a method for producing an ink for producing an electronic device, which comprises a step of heating and dissolving the above-mentioned solvent composition for producing an electronic device at 30 to 90 ° C.
  • the present invention also provides a solvent and the following formula (1):
  • R represents an aliphatic hydrocarbon group having 1 or more carbon atoms.
  • all four Rs are the same group or two different groups.
  • An ink for producing an electronic device comprising a compound represented by the formula:
  • the present invention further provides the above-described ink for manufacturing an electronic device, further comprising a conductive metal material, a semiconductor material, a magnetic material, a dielectric material, or an insulating material.
  • the present invention also provides the above-mentioned ink for manufacturing an electronic device, wherein the binder resin content is 10% by weight or less.
  • a solvent composition for use in an ink for producing an electronic device by a printing method comprising a solvent and a compound represented by formula (1).
  • R in the formula (1) is a linear or branched alkyl group, alkenyl group, or alkynyl group having 6 to 18 carbon atoms.
  • the compound represented by formula (1) is at least one compound selected from the compounds represented by formulas (1-2) to (1-5) The solvent composition for electronic device manufacture of description.
  • the compound represented by the formula (1) is a compound represented by the formula (1-3) and / or a compound represented by the formula (1-4) [1] or [2] Solvent composition for manufacturing electronic devices.
  • the solvent composition for producing an electronic device according to any one of [1] to [6], wherein the content of the solvent is 20.0 to 99.9% by weight of the total amount of the solvent composition for producing an electronic device. .
  • the solvent is n-decane, n-dodecane, propylene glycol methyl-n-propyl ether, propylene glycol methyl-n-butyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl-n-propyl ether, dipropylene glycol methyl.
  • -At least one selected from the group consisting of n-butyl ether, dipropylene glycol methyl isoamyl ether, tripropylene glycol methyl n-propyl ether, cyclohexyl acetate, 2-methylcyclohexyl acetate, and 4-t-butylcyclohexyl acetate
  • the solvent composition for producing an electronic device according to any one of [1] to [7].
  • the solvent composition for producing an electronic device according to any one of [1] to [8], which is less than 50% by weight of the total solvent contained in the product.
  • the electrical property imparting material is a conductive metal material, a semiconductor material, a magnetic material, a dielectric material, or an insulating material.
  • the binder resin content is 10% by weight or less.
  • the binder resin is a polymer compound having a molecular weight of 10,000 or more.
  • a method for manufacturing an electronic device comprising a step of applying an ink for manufacturing an electronic device according to any one of [12] to [20] by a printing method, forming a wiring through a step of drying and baking. .
  • the solvent composition for producing an electronic device of the present invention contains the compound represented by the above formula (1), an ink having a viscosity suitable for forming a wiring or the like by a printing method is produced through a step of heating and dissolving. can do. Moreover, the ink obtained using the solvent composition for manufacturing an electronic device of the present invention is not easily dripped, and a highly accurate wiring pattern can be formed by a printing method. Moreover, in a baking process, it can bake at lower temperature and it can prevent that a to-be-coated surface member is softened and deform
  • solvent composition for manufacturing electronic devices The solvent composition for producing an electronic device of the present invention (hereinafter sometimes referred to as “solvent composition”) is a solvent composition used in an ink for producing an electronic device using a printing method, And a compound represented by the formula (1).
  • the solvent composition of the present invention contains a compound represented by the following formula (1).
  • R represents an aliphatic hydrocarbon group having 1 or more carbon atoms.
  • all four Rs are the same group or two different groups.
  • the compound represented by the following formula (1) acts as a thickener.
  • R is an aliphatic hydrocarbon group having 1 or more carbon atoms.
  • R is an aliphatic hydrocarbon group having 1 or more carbon atoms.
  • Examples of the compound represented by the formula (1) include compounds represented by the following formulas (1-1) to (1-5).
  • R 1 and R 2 are different from each other and represent an aliphatic hydrocarbon group having 1 or more carbon atoms, and examples can be given in the same manner as R.
  • R ⁇ 1 > exists in a formula they show the same group. The same applies to R 2 .
  • the compounds represented by the above formulas (1-2) to (1-5) are preferable from the viewpoint that the viscosity can be increased by adding a small amount.
  • a compound represented by (1-3) and / or a compound represented by the above formula (1-4) is preferred.
  • the evaporation temperature is 120 to 380 ° C. (preferably 150 to 330 ° C., more preferably 150 to 320 ° C., particularly preferably 150 to 315 ° C., and most preferably 170 ° C.).
  • the evaporation temperature can be controlled by the type of side chain. When the evaporation temperature exceeds the above range, firing at a low temperature becomes difficult, and the coated surface member may be softened and deformed by being exposed to a high temperature for a long time. On the other hand, if the evaporation temperature is lower than the above range, the composition may change due to vaporization at the time of ink preparation or printing, and it tends to be difficult to stably form wirings and the like.
  • the compound represented by the formula (1) can self-associate by hydrogen bonding at the amide bond site to form a fiber-like self-assembly. Furthermore, since the R group has an affinity for the solvent, the solvent can be thickened by being compatible with the solvent, and an ink for producing an electronic device that is stable over time can be formed.
  • the content of the compound represented by the formula (1) in the solvent composition of the present invention (when two or more are contained, the total content) is, for example, 0.1 to 50 parts by weight with respect to 100 parts by weight of the solvent. Degree, preferably 0.5 to 30 parts by weight, particularly preferably 0.5 to 10 parts by weight.
  • the content of the compound represented by the formula (1) is below the above range, it becomes difficult to stably maintain the viscosity of the ink, such as a decrease in viscosity due to a temperature change. It may be difficult to form.
  • the content of the compound represented by the formula (1) exceeds the above range, the viscosity of the ink becomes too high, and it may be difficult to form a wiring or the like by a printing method.
  • the compound represented by Formula (1) can be manufactured by the following method etc., for example.
  • 1. A method of reacting cyclohexanetetracarboxylic acid with thionyl chloride to obtain cyclohexanetetracarboxylic acid tetrachloride, and reacting the resulting cyclohexanetetracarboxylic acid tetrachloride with an amine.
  • Amine acid (1) is reacted with cyclohexanetetracarboxylic dianhydride to obtain an amic acid, and amine (2) (which may be the same as or different from amine (1)) is used with a condensing agent.
  • 1,2,4,5-cyclohexanetetracarboxylic acid can be suitably used.
  • Examples of the amine (R—NH 2 : R is the same as described above) used in the production method 1 above include, for example, butylamine, pentylamine, isopentylamine, hexylamine, octylamine, 2-ethylhexylamine, decylamine, laurylamine Aliphatic hydrocarbon groups having 1 or more carbon atoms (preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms) such as myristylamine, stearylamine, oleylamine, etc. (for example, linear or branched alkyl) And an amine having a group, an alkenyl group, or an alkynyl group.
  • the reaction between cyclohexanetetracarboxylic acid tetrachloride and amine can be carried out, for example, by dropping cyclohexanetetracarboxylic acid tetrachloride into a system charged with amine.
  • One amine may be used alone, or two different amines may be used.
  • the amount of amine to be used (the total amount when two different amines are used) is, for example, about 4 to 8 mol, preferably 4 to 6 mol, per 1 mol of cyclohexanetetracarboxylic acid tetrachloride.
  • the reaction between cyclohexanetetracarboxylic acid tetrachloride and amine can be carried out in the presence or absence of a solvent.
  • the solvent include saturated or unsaturated hydrocarbon solvents such as pentane, hexane, heptane, octane and petroleum ether; aromatic hydrocarbon solvents such as benzene, toluene and xylene; methylene chloride, chloroform, 1, 2 -Halogenated hydrocarbon solvents such as dichloroethane, chlorobenzene, bromobenzene; ether solvents such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane, cyclopentyl methyl ether; acetonitrile, benzonitrile, etc.
  • Nitrile solvents such as dimethyl sulfoxide
  • sulfolane solvents such as sulfolane
  • amide solvents such as dimethylformamide
  • high-boiling solvents such as silicone oil.
  • the amount of the solvent used is, for example, about 50 to 300% by weight with respect to the total amount of cyclohexanetetracarboxylic acid tetrachloride and amine.
  • concentration of a reaction component will become low and there exists a tendency for reaction rate to fall.
  • the reaction between cyclohexanetetracarboxylic acid tetrachloride and amine is usually carried out under normal pressure.
  • the atmosphere of the reaction is not particularly limited as long as the reaction is not inhibited, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like.
  • the reaction temperature is, for example, about 30 to 60 ° C.
  • the reaction time is, for example, about 0.5 to 20 hours.
  • an aging step may be provided. When the aging step is provided, the aging temperature is, for example, about 30 to 60 ° C., and the aging time is, for example, about 1 to 5 hours.
  • the reaction can be carried out by any method such as batch, semi-batch and continuous methods.
  • the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a combination means combining these.
  • cyclohexanetetracarboxylic dianhydride, amine (1) and the following solvent are charged into the system and aged to form an amic acid, and then amine (2) and a condensing agent (
  • a compound represented by formula (1) can be produced by charging and aging carbodiimide or a salt thereof.
  • 1,2,4,5-cyclohexanetetracarboxylic acid-1,2: 4,5-dianhydride can be preferably used.
  • Examples of the amines (1) and (2) include the same examples as amines that can be used in the above production method 1.
  • the amount of amine (1) used is, for example, about 2 to 4 moles, preferably 2 to 3 moles per mole of cyclohexanetetracarboxylic dianhydride.
  • the amount of amine (2) to be used is, for example, about 2 to 4 mol, preferably 2 to 3 mol, per 1 mol of cyclohexanetetracarboxylic dianhydride.
  • R ′ and R ′′ are, for example, a linear or branched alkyl group having 3 to 8 carbon atoms which may have a heteroatom-containing substituent, or 3 to 8 membered Examples thereof include cycloalkyl groups.
  • R ′ and R ′′ may be the same or different.
  • R ′ and R ′′ may be bonded to each other to form a ring together with the (—N ⁇ C ⁇ N—) group in the above formula.
  • linear or branched alkyl group having 3 to 8 carbon atoms examples include propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, s-pentyl, t-pentyl, Examples include hexyl, isohexyl, s-hexyl, t-hexyl groups and the like.
  • Examples of the 3- to 8-membered cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl groups.
  • heteroatom-containing substituents examples include nitrogen atom-containing substituents such as di (C 1-3 ) alkylamino groups such as amino groups and dimethylamino groups.
  • carbodiimide examples include diisopropylcarbodiimide, dicyclohexylcarbodiimide, N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide, and the like.
  • carbodiimide salt examples include hydrochloride (specifically, N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide hydrochloride). These can be used alone or in combination of two or more.
  • the amount of carbodiimide used is, for example, about 2 to 6 moles, preferably 2 to 4 moles per mole of cyclohexanetetracarboxylic dianhydride.
  • a proton-accepting solvent for example, pyridine, triethylamine, tributylamine, etc.
  • a proton-accepting solvent for example, pyridine, triethylamine, tributylamine, etc.
  • the amount of the solvent used is, for example, about 50 to 300% by weight, preferably 100 to 250% by weight, based on the total amount of amic acid.
  • concentration of a reaction component will become low and there exists a tendency for reaction rate to fall.
  • the above reaction is usually performed under normal pressure.
  • the atmosphere of the reaction is not particularly limited as long as the reaction is not inhibited, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like.
  • the aging temperature (reaction temperature) is, for example, about 30 to 70 ° C.
  • the aging time of cyclohexanetetracarboxylic dianhydride and amine is, for example, about 0.5 to 5 hours, and the aging time of amic acid and amine is, for example, about 0.5 to 20 hours.
  • the reaction can be carried out by any method such as batch, semi-batch and continuous methods.
  • the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a combination means combining these.
  • solvent As the solvent contained in the solvent composition of the present invention, it is preferable to use a solvent excellent in solubility of the compound represented by the above formula (1).
  • Examples of the solvent include those having an SP value at 25 ° C. [(cal / cm 3 ) 0.5 : Fedors calculated value] of 7.0 to 9.0 (preferably 7.5 to 9.0). 1 or 2 or more are excellent in solubility of the compound represented by the above formula (1), and the heating temperature when dissolving the compound represented by the above formula (1) is lowered, for example, This is preferable in that it can be suppressed to about 50 to 90 ° C.
  • a solvent having an SP value outside the above range has a low solubility of the compound represented by the above formula (1), and thus there is a tendency that heating at a higher temperature is required when the compound is dissolved.
  • n-decane (SP value: 7.6), n-dodecane (SP value: 7.7), propylene glycol methyl-n-propyl ether (SP value: 8.1), propylene glycol.
  • Methyl-n-butyl ether (SP value: 8.1), dipropylene glycol dimethyl ether (SP value: 8.4), dipropylene glycol methyl-n-propyl ether (SP value: 8.2), dipropylene glycol methyl- n-butyl ether (SP value: 8.2), dipropylene glycol methyl isoamyl ether (SP value: 8.0), tripropylene glycol methyl-n-propyl ether (SP value: 8.2), cyclohexyl acetate (SP value) : 8.9), 2-methylcyclohexyl acetate (SP value: 8.5), and 4-t Butylcyclohexyl acetate (SP value: 8.2) it is preferred to use at least one
  • the content of the solvent in the solvent composition of the present invention (when two or more are contained, the total content) is, for example, 20.0 to 99.9% by weight, preferably 30.0 to 99.5% by weight, particularly It is preferably 40.0 to 99.5% by weight, most preferably 50.0 to 99.5% by weight, particularly preferably 70.0 to 99.5% by weight.
  • the content of the solvent is below the above range, the viscosity of the ink becomes too high, and it may be difficult to form a wiring or the like by a printing method.
  • the solvent composition of the present invention may be a solvent other than the above-mentioned solvent (hereinafter referred to as “other solvent” if necessary) as long as the effect is not impaired.
  • other solvent a solvent other than the above-mentioned solvent
  • a well-known and conventional solvent used for electronic device production applications may be added.
  • the amount of other solvents added is, for example, less than 50% by weight, preferably 30% by weight or less, particularly preferably 20% by weight or less, most preferably, of the total solvent (100% by weight) contained in the solvent composition of the present invention. Is 10% by weight or less.
  • the ink for manufacturing an electronic device of the present invention (hereinafter sometimes referred to as “ink”) is an ink for forming wiring and electrodes of an electronic device by application by a printing method. The compound represented by this is included.
  • the ink of the present invention comprises, for example, a step of heating and dissolving the solvent composition at 30 to 90 ° C. (upper limit is preferably 80 ° C., lower limit is preferably 40 ° C., particularly preferably 50 ° C., most preferably 70 ° C.). It can be manufactured after that.
  • the solvent composition is heated and dissolved at 30 to 90 ° C. (the upper limit is preferably 80 ° C., the lower limit is preferably 40 ° C., particularly preferably 50 ° C., most preferably 70 ° C.).
  • the time required for dissolution by heating is, for example, about 3 to 60 minutes (preferably 10 to 30 minutes).
  • room temperature eg, 1 to 30 ° C.
  • the cooling may be performed gradually at room temperature or rapidly by ice cooling or the like.
  • the ink of the present invention it is preferable to add at least one electrical property imparting material selected from the group consisting of conductive metal materials, semiconductor materials, magnetic materials, dielectric materials, and insulating materials.
  • the content of the electrical property imparting material (the total amount when containing two or more types) is, for example, about 0.1 to 90% by weight of the total amount of ink (100% by weight).
  • conductive metal material and magnetic material well-known and commonly used materials can be used.
  • semiconductor materials can be used, such as pentacene, fullerene derivatives, polythiophene derivatives, metals (copper, indium, gallium, selenium, arsenic, cadmium, tellurium, and alloys thereof), silicon fine particles, etc. Can be mentioned.
  • dielectric material and the insulating material well-known and customary materials can be used, and examples thereof include cycloolefin polymer, fluororesin, butyral resin, glass, paper, Teflon (registered trademark) and the like.
  • the ink of the present invention obtained through the above steps contains a compound represented by the above formula (1), and the compound self-assembles in a solvent to form a string-like aggregate, which is viscous like a polymer compound. Therefore, even if the binder resin is not blended, it has an appropriate viscosity for accurately forming the wiring and electrodes of the electronic device by the printing method.
  • the ink of the present invention has an appropriate viscosity, and the viscosity at 25 ° C. (at a shear rate of 0.5 s ⁇ 1 ) is, for example, about 0.01 to 1000 Pa ⁇ s, preferably 0.1 to 500 Pa ⁇ s, particularly preferably. Is 1 to 200 Pa ⁇ s.
  • the ink of the present invention does not require the addition of a binder resin (for example, a polymer compound having a molecular weight of 10,000 or more such as an ethyl cellulose resin, an alkyl cellulose resin, a polyvinyl acetal resin, and an acrylic resin).
  • a binder resin for example, a polymer compound having a molecular weight of 10,000 or more such as an ethyl cellulose resin, an alkyl cellulose resin, a polyvinyl acetal resin, and an acrylic resin.
  • the amount added is, for example, 10% by weight or less of the total amount of ink (100%), preferably 5% by weight or less, more preferably less than 5% by weight, particularly preferably 3% by weight or less, and most preferably 1% by weight or less. is there. If the amount of the binder resin added exceeds the above range, the ash content derived from the binder resin caused by firing causes a decrease in electrical characteristics, which is not preferable.
  • the string-like aggregate composed of the compound represented by the formula (1) contained in the ink of the present invention has excellent thermal decomposability and easily has a low molecular weight. Therefore, the ink of the present invention can be baked at a lower temperature (for example, 100 to 350 ° C., preferably 150 to 300 ° C., particularly preferably 150 to 250 ° C.) as compared with an ink to which a viscosity is imparted by a binder resin such as ethyl cellulose. It is possible to prevent softening and deformation of the coated surface member in the firing step.
  • a lower temperature for example, 100 to 350 ° C., preferably 150 to 300 ° C., particularly preferably 150 to 250 ° C.
  • the residual amount of ash after firing can be reduced extremely low (the residual amount of ash is, for example, 4.5% by weight or less, preferably 4.0% by weight or less, particularly preferably 3.0% by weight or less). , Most preferably 2.5% by weight or less), it is possible to suppress a decrease in electrical properties caused by ash.
  • the ink of the present invention has excellent electrical characteristics (for example, conductivity or insulation) through the steps of coating, drying, and firing on a surface member (for example, ceramic substrate, green sheet, etc.) by a printing method. Wiring and the like can be formed with high accuracy. Therefore, the ink of the present invention is particularly useful as an ink for producing, for example, a capacitor, an inductor, a varistor, a thermistor, a speaker, an actuator, an antenna, a solid oxide fuel cell (SOFC), etc. (particularly, a multilayer ceramic capacitor).
  • SOFC solid oxide fuel cell
  • the obtained wet powder was recrystallized with CHCl 3 / CH 3 OH (70/30 (v / v)), and 1,2,4,5-cyclohexanetetracarboxylic acid di (2-ethylhexylamide) di ( Oleylamide) [1,2,4,5-cyclohexanetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,5-di (oleylamide) and 1,2,4,5-cyclohexanetetracarboxylic 11.9 g of a mixture of acid-1,5-di (2-ethylhexylamide) -2,4-di (oleylamide)] (yield: 61%). The structure of the reaction product was confirmed by 1 H-NMR.
  • Example 1 The solvent composition obtained by adding the thickener (1) obtained in Preparation Example 1 to n-decane (manufactured by Wako Pure Chemical Industries, Ltd.) as a solvent so that the concentration of the thickener is 1% by weight. (1) was obtained.
  • the obtained solvent composition (1) was dissolved by heating at a liquid temperature of 80 ° C. for 0.5 hours and allowed to cool to room temperature (25 ° C.) to obtain a paste-like ink (1) (viscosity at 25 ° C. [ At a shear rate of 0.5 s ⁇ 1 ]: 6 Pa ⁇ s).
  • Comparative Example 1 A solvent composition was obtained in the same manner as in Example 1 except that the composition (unit: wt%) shown in Table 1 was changed, and an ink was obtained.
  • ethyl cellulose (trade name “Etocel STD200”, manufactured by Nisshin Kasei Co., Ltd.) was added instead of the thickener so that the resin concentration became 5% by weight, and the liquid temperature was 80 ° C. for 3 hours. It was dissolved by heating and allowed to cool at room temperature (25 ° C.) to obtain a paste-like ink.
  • Solvent dekane n-decane (manufactured by Wako Pure Chemical Industries, Ltd., SP value: 7.6)
  • DPMNP Dipropylene glycol methyl-n-propyl ether (manufactured by Daicel Corporation, SP value: 8.2)
  • CHXA cyclohexyl acetate (manufactured by Daicel Corporation, SP value: 8.9)
  • the solvent composition for producing an electronic device of the present invention can produce an ink having a viscosity suitable for forming a wiring or the like by a printing method through a step of dissolving by heating. Moreover, the ink obtained using the solvent composition for manufacturing an electronic device of the present invention is not easily dripped, and a highly accurate wiring pattern can be formed by a printing method. Moreover, in a baking process, it can bake at lower temperature and it can prevent that a to-be-coated surface member is softened and deform

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  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Manufacturing Of Printed Wiring (AREA)
  • Conductive Materials (AREA)
  • Organic Insulating Materials (AREA)
  • Parts Printed On Printed Circuit Boards (AREA)
  • Ceramic Capacitors (AREA)
  • Fixed Capacitors And Capacitor Manufacturing Machines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention a pour but de fournir une composition de solvant, devant être utilisée dans une encre pour former un câblage et des électrodes dans un dispositif électronique par un procédé d'impression, la composition de solvant permettant : d'améliorer la précision d'impression de l'encre ; d'effectuer une calcination à des températures basses ; de maintenir à un niveau extrêmement faible la quantité de cendres produites après la calcination. Cette composition de solvant pour la fabrication d'un dispositif électronique est utilisée dans une encre, pour la fabrication d'un dispositif électronique par un procédé d'impression, et comprend un solvant et un composé représenté par la formule (1). Dans la formule, R représente un groupe hydrocarbure aliphatique contenant un nombre d'atomes de carbone supérieur ou égal à 1. Les quatre R dans la formule sont tous le même groupe ou sont deux groupes différents.
PCT/JP2016/052068 2015-02-03 2016-01-26 Composition de solvant pour la fabrication d'un dispositif électronique WO2016125618A1 (fr)

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Cited By (2)

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JP2018520479A (ja) * 2015-06-12 2018-07-26 メルク パテント ゲーエムベーハー Ｏｌｅｄ調合物のための溶媒としての非芳香族環を含むエステル
WO2018199144A1 (fr) * 2017-04-28 2018-11-01 株式会社ダイセル Composition de solvant pour la production d'un dispositif électronique

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JPH08162358A (ja) * 1994-12-07 1996-06-21 Sumitomo Metal Mining Co Ltd 積層セラミックコンデンサ内部電極用ペースト
JP2005197079A (ja) * 2004-01-07 2005-07-21 Murata Mfg Co Ltd 導電性ペースト
JP2009155592A (ja) * 2007-12-28 2009-07-16 New Japan Chem Co Ltd 新規な有機ゲル化剤
JP2013149457A (ja) * 2012-01-19 2013-08-01 Sumitomo Metal Mining Co Ltd 内部電極用導電ペースト

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WO2014057846A1 (fr) * 2012-10-11 2014-04-17 株式会社ダイセル Composition de solvant pour la fabrication d'un dispositif électrique

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JPH08162358A (ja) * 1994-12-07 1996-06-21 Sumitomo Metal Mining Co Ltd 積層セラミックコンデンサ内部電極用ペースト
JP2005197079A (ja) * 2004-01-07 2005-07-21 Murata Mfg Co Ltd 導電性ペースト
JP2009155592A (ja) * 2007-12-28 2009-07-16 New Japan Chem Co Ltd 新規な有機ゲル化剤
JP2013149457A (ja) * 2012-01-19 2013-08-01 Sumitomo Metal Mining Co Ltd 内部電極用導電ペースト

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018520479A (ja) * 2015-06-12 2018-07-26 メルク パテント ゲーエムベーハー Ｏｌｅｄ調合物のための溶媒としての非芳香族環を含むエステル
US10808170B2 (en) 2015-06-12 2020-10-20 Merck Patent Gmbh Esters containing non-aromatic cycles as solvents for OLED formulations
WO2018199144A1 (fr) * 2017-04-28 2018-11-01 株式会社ダイセル Composition de solvant pour la production d'un dispositif électronique
KR20200002861A (ko) * 2017-04-28 2020-01-08 주식회사 다이셀 전자 디바이스 제조용 용제 조성물
JPWO2018199144A1 (ja) * 2017-04-28 2020-05-14 株式会社ダイセル 電子デバイス製造用溶剤組成物
JP7113008B2 (ja) 2017-04-28 2022-08-04 株式会社ダイセル 電子デバイス製造用溶剤組成物
US11655381B2 (en) 2017-04-28 2023-05-23 Daicel Corporation Solvent composition for electronic device production
KR102560882B1 (ko) * 2017-04-28 2023-07-31 주식회사 다이셀 전자 디바이스 제조용 용제 조성물

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TW201638247A (zh) 2016-11-01
JP6652509B2 (ja) 2020-02-26
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