WO2015087811A1 - 電気デバイス製造用溶剤組成物 - Google Patents

電気デバイス製造用溶剤組成物 Download PDF

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Publication number
WO2015087811A1
WO2015087811A1 PCT/JP2014/082290 JP2014082290W WO2015087811A1 WO 2015087811 A1 WO2015087811 A1 WO 2015087811A1 JP 2014082290 W JP2014082290 W JP 2014082290W WO 2015087811 A1 WO2015087811 A1 WO 2015087811A1
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Prior art keywords
electronic device
solvent
ether
composition
acetate
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PCT/JP2014/082290
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English (en)
French (fr)
Japanese (ja)
Inventor
坂西裕一
鈴木陽二
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株式会社ダイセル
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Application filed by 株式会社ダイセル filed Critical 株式会社ダイセル
Priority to JP2015552426A priority Critical patent/JP6453765B2/ja
Priority to CN201480067318.XA priority patent/CN105814162B/zh
Priority to KR1020167014745A priority patent/KR102202848B1/ko
Publication of WO2015087811A1 publication Critical patent/WO2015087811A1/ja
Priority to PH12016500977A priority patent/PH12016500977B1/en

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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
    • 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

Definitions

  • the present invention relates to a solvent composition containing a solvent and a thickener and forming a paste composition by heating and dissolving.
  • the paste composition is applied to a member having a surface to be coated (hereinafter sometimes referred to as a “surface to be coated”) using a printing method to form a wiring or a coating film. Used for applications.
  • This application claims the priority of Japanese Patent Application No. 2013-254105 for which it applied to Japan on December 9, 2013, 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 (SOFC), and the like.
  • capacitors inductors, varistors, thermistors, transistors, speakers, actuators, antennas, solid oxide fuel cells (SOFC), and the like.
  • SOFC solid oxide fuel cells
  • a multilayer capacitor is generally manufactured through the following processes.
  • a ceramic sheet is dispersed in a polyvinyl acetal resin such as polyvinyl butyral or a binder resin such as an acrylic resin and a solvent to form a slurry, which is then formed into a sheet to obtain a green sheet.
  • a paste composition mainly composed of a conductive metal material (for example, nickel, palladium), a binder resin (for example, ethyl cellulose), and an organic solvent (for example, terpineol) is applied on a green sheet by a printing method or the like. Wiring and coating film are formed (application process). 3.
  • the organic solvent in the paste composition is dried (drying step). 4).
  • the laminated sheet on which the wiring and coating film are formed is cut into a predetermined size, and a plurality of sheets are stacked and thermocompression bonded to obtain a laminated body. 5.
  • a multilayer capacitor is obtained (firing step).
  • the binder resin has a function of fixing the conductive metal material or the insulating material on the green sheet.
  • an ethyl cellulose resin has been mainly used because it is excellent in applicability and a coating film having a precise shape can be easily formed.
  • the carbon component remains as ash after firing, which reduces electrical properties and causes volatiles to form voids in the process of thermal decomposition, resulting in wiring and coating films. It has been a problem that the yield is lowered due to the formation failure of the film, delamination or the like.
  • Patent Document 1 discloses that using a polyvinyl acetal resin instead of an ethyl cellulose resin improves adhesion with a green sheet and reduces ash content.
  • the polyvinyl acetal resin it has been difficult to completely prevent the decrease in conductivity, the formation failure of the wiring / coating film, and the occurrence of delamination.
  • the object of the present invention is to be able to apply with high accuracy using a printing method, and by firing after application, it is possible to suppress the generation of ash and volatiles and to provide a wiring / coating film excellent in electrical characteristics.
  • An object of the present invention is to provide a solvent composition for manufacturing an electronic device, which is a raw material of a paste composition that can be formed with a high yield.
  • Another object of the present invention is to provide a wiring / coating film that can be applied with high accuracy using a printing method and is excellent in electrical characteristics by suppressing the generation of ash and volatiles by baking after coating.
  • An object of the present invention is to provide an electronic device manufacturing paste composition that can be formed with high yield, and a manufacturing method thereof.
  • a low molecular weight compound represented by the following formula (1) forms a string-like aggregate by self-organizing in a solvent when heated and dissolved. It exhibits viscosity like a polymer, volatilizes at a lower temperature than polymer compounds such as ethyl cellulose, has excellent thermal decomposability, and can significantly reduce the residue of ash and the generation of volatiles due to baking. I found it.
  • the electronic device manufacture by a printing method replaces with the paste composition obtained by mixing binder resin, such as ethylcellulose, with a solvent, and heats the mixture of the low molecular weight compound and solvent which are represented by said Formula (1).
  • the coating process has a viscosity suitable for forming a wiring / coating film by a printing method, and is capable of forming a highly accurate wiring pattern that is difficult to drip and drying.
  • the firing process there is no need to heat at high temperature for a long time, it can be quickly dried and fired at low temperature, and the coated surface member can be prevented from being softened and deformed by being exposed to high temperature for a long time.
  • this invention is a solvent composition for manufacturing an electronic device using a printing method, Comprising: A solvent and following formula (1) (In the formula, ring Z represents a ring selected from benzene, benzophenone, biphenyl, and naphthalene, R represents an aliphatic hydrocarbon group having 6 or more carbon atoms, and n represents an integer of 3 or more. R may be the same or different)
  • a solvent and following formula (1) In the formula, ring Z represents a ring selected from benzene, benzophenone, biphenyl, and naphthalene, R represents an aliphatic hydrocarbon group having 6 or more carbon atoms, and n represents an integer of 3 or more. R may be the same or different
  • 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 20 carbon atoms. To do.
  • the present invention also provides a solvent having a SP value [(cal / cm 3 ) 0.5 ] at 25 ° C. in the range of 7.0 to 9.2, and an SP value [(cal / cm 3 ) at 25 ° C. 0.5 ] is at least one solvent selected from solvents in the range of 10.0 to 14.0.
  • the above-mentioned solvent composition for producing an electronic device is provided.
  • the solvent is n-decane, 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- n-butyl ether, cyclohexyl acetate, 2-methylcyclohexyl acetate, 4-t-butylcyclohexyl acetate, 3-methoxybutyl acetate, dipropylene glycol methyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 3-methoxybutanol, And at least one selected from 1,2,5,6-tetrahydrobenzyl alcohol Providing device manufacturing solvent composition.
  • 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% by weight of the whole solvent composition for producing an electronic device. .
  • the present invention also provides a method for producing a paste composition for producing an electronic device, wherein the above-mentioned solvent composition for producing an electronic device is heated and dissolved at 30 to 90 ° C.
  • the present invention also provides an electronic device manufacturing paste composition obtained by the method for manufacturing an electronic device manufacturing paste composition.
  • the present invention also provides the above-mentioned paste composition 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 electronic device manufacturing paste composition described above, wherein the binder resin content is 10% by weight or less.
  • a solvent composition for producing an electronic device using a printing method comprising a solvent and a compound represented by formula (1) for producing an electronic device.
  • the solvent composition for manufacturing an electronic device is a solvent composition used as a dispersion medium in a paste composition for manufacturing an electronic device used when forming a wiring or a coating film constituting the electronic device by using a printing method.
  • R1 in formula (1) is any one of [1] to [3], wherein R is a linear or branched alkyl group, alkenyl group, or alkynyl group having 6 to 20 carbon atoms.
  • Solvent composition for manufacturing electronic devices [5]
  • the compound represented by the formula (1) is a compound in which R in the formula (1) is the same and is a linear alkyl group having 6 to 18 carbon atoms and / or in the formula (1).
  • R is two different groups, one group is a branched alkyl group having 6 to 18 carbon atoms, and the other group is a linear alkenyl group having 12 to 18 carbon atoms
  • the solvent composition for manufacturing an electronic device according to any one of [3].
  • the compound represented by formula (1) is at least one compound selected from compounds represented by formulas (1-1) to (1-22).
  • the solvent has an SP value [(cal / cm 3 ) 0.5 ] at 25 ° C. in the range of 7.0 to 9.2, and an SP value [(cal / cm 3 ) 0.5 ] at 25 ° C.
  • the solvent composition for manufacturing an electronic device according to any one of [1] to [6], which is at least one solvent selected from solvents in the range of 10.0 to 14.0.
  • the solvent is n-decane, 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-n-butyl ether.
  • n R A compound represented by the formula (1) in which at least one is an aliphatic hydrocarbon group having 18 to 20 carbon atoms (particularly preferably a linear alkenyl group having 18 to 20 carbon atoms) is used as a solvent.
  • n R is an aliphatic hydrocarbon group having 18 to 20 carbon atoms (particularly preferably, carbon
  • the content of the compound represented by the formula (1) is 0.1 to 50% by weight of the whole solvent composition for manufacturing an electronic device, according to any one of [1] to [9] Solvent composition for manufacturing electronic devices.
  • a method for producing a paste composition for producing an electronic device wherein the solvent composition for producing an electronic device according to any one of [1] to [10] is heated and dissolved at 30 to 90 ° C.
  • a paste composition for manufacturing an electronic device obtained by the method for manufacturing a paste composition for manufacturing an electronic device according to [11].
  • the paste composition for manufacturing an electronic device according to [12] further including a conductive metal material, a semiconductor material, a magnetic material, a dielectric material, or an insulating material.
  • Paste composition [15] The paste composition for manufacturing an electronic device according to any one of [12] to [14], wherein the content of the binder resin is 10% by weight or less.
  • the electronic device manufacturing paste composition is any one of [12] to [15], which is a paste composition for forming a wiring or a coating film constituting an electronic device using a printing method. A paste composition for manufacturing electronic devices.
  • the solvent composition for producing an electronic device of the present invention contains a solvent and a low molecular weight compound represented by the above formula (1), it is suitable for forming a wiring / coating film by a printing method by dissolving with heating.
  • a paste composition having a viscosity can be formed.
  • the paste composition is used, a highly accurate wiring pattern can be formed which is difficult to drip.
  • drying and firing can be performed at a low temperature, and the coated surface member can be prevented from being softened and deformed by being exposed to a high temperature for a long time.
  • the solvent composition for manufacturing an electronic device of the present invention can form a fine pattern with high accuracy by each printing method, and the yield decreases due to poor formation of wiring / coating film or delamination (delamination). Therefore, it is extremely useful as a raw material for a paste composition for forming a wiring or coating film having excellent electrical characteristics.
  • FIG. 1 is a view showing a weight reduction mode when the paste compositions obtained in Examples and Comparative Examples are heated from 20 ° C. to 400 ° C. at a rate of 10 ° C./min and the amount of residual ash at 300 ° C.
  • the solvent composition for producing an electronic device of the present invention is a solvent composition for producing an electronic device by a printing method (more specifically, used in producing an electronic circuit by a printing method in the production process of the electronic device. And a solvent and a compound represented by the following formula (1).
  • the thickener of the present invention is represented by the following formula (1).
  • ring Z is a ring selected from benzene, benzophenone, biphenyl, and naphthalene.
  • R is an aliphatic hydrocarbon group having 6 or more carbon atoms, for example, about 6 to 20 carbon atoms such as hexyl, octyl, 2-ethylhexyl, decyl, dodecyl, myristyl, stearyl, nonadecyl group, etc.
  • R is an aliphatic hydrocarbon group having 6 or more carbon atoms, for example, about 6 to 20 carbon atoms such as hexyl, octyl, 2-ethylhexyl, decyl, dodecyl, myristyl, stearyl, nonadecyl group, etc.
  • a linear or branched alkenyl group of about 6 to 20 (preferably 6 to 18, particularly preferably 12 to 18); about 6 to 20 carbon atoms such as hexynyl, octynyl, decynyl, pentadecynyl, octadecynyl group (preferably Includes 6-18, particularly preferably 12-18) linear or branched alkynyl groups.
  • n represents an integer of 3 or more, preferably 3 to 4, particularly preferably 4.
  • N n may be the same or different.
  • examples of the compound in which n is 4 include compounds represented by the following formulas.
  • R 1 and R 2 are different from each other and represent an aliphatic hydrocarbon group having 6 or more carbon atoms, and examples similar to R can be given.
  • the evaporation temperature (under normal pressure) 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 170-315 ° C.), and the evaporation temperature can be controlled by the type of side chain.
  • the evaporation temperature exceeds the above range, it becomes difficult to quickly vaporize under low temperature conditions, and the coated surface member may be softened and deformed by being exposed to a high temperature for a long time.
  • the evaporation temperature of the compound represented by the formula (1) is the weight when the temperature is increased from 20 ° C. to 400 ° C. at 10 ° C./min using a differential thermogravimetric simultaneous measurement apparatus (TG / DTA). Is the temperature at which 5% of the decrease occurred.
  • a ring Z is benzene, and R is a linear or branched alkyl or alkenyl group having about 6 to 20 carbon atoms (preferably 6 to 18), n
  • R is a linear or branched alkyl or alkenyl group having about 6 to 20 carbon atoms (preferably 6 to 18)
  • n A compound in which R is 3 or 4
  • R is a linear or branched alkyl group having about 6 to 20 carbon atoms (preferably 6 to 18)
  • n is 3 or 4 Is preferred.
  • 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. In particular, when R is two or more different groups in the compound represented by the formula (1), when the solvent has transparency, the solvent can be thickened while maintaining its transparency. A stable paste composition for manufacturing an electronic device can be formed.
  • the compound represented by Formula (1) can be manufactured by the following method etc., for example. 1, following formula (2) (Wherein ring Z and n are the same as above) Is reacted with thionyl chloride to obtain an aromatic carboxylic acid chloride, and the resulting aromatic carboxylic acid chloride is reacted with an amine (R—NH 2 ) (R is as defined above). 2. Amine acid (1) (R—NH 2 ) (R is the same as above) is reacted with the aromatic carboxylic acid anhydride corresponding to the aromatic carboxylic acid to obtain an amic acid, and further amine (2) (R -NH 2 ) (R is the same as above) [Amine (2) may be the same as or different from amine (1)] using carbodiimide
  • aromatic carboxylic acid examples include 1,3,5-benzenetricarboxylic acid, 1,2,4,5-benzenetetracarboxylic acid, 2,4,5-benzophenone tricarboxylic acid, 3,4,3′- Benzophenone tricarboxylic acid, 3,4,4′-benzophenone tricarboxylic acid, 3,3 ′, 4,4′-benzophenone tetracarboxylic acid, 1,1′-biphenyl-2,4,4′-tricarboxylic acid, 1,1 '-Biphenyl-2,3,3', 4'-tetracarboxylic acid, 1,6,7-naphthalenetricarboxylic acid, 1,2,3-naphthalenetricarboxylic acid, 1,3,8-naphthalenetricarboxylic acid, 1, Examples include 4,6-naphthalene tricarboxylic acid and 1,4,5,8-naphthalene tetracarboxylic acid.
  • Examples of the amine (R—NH 2 ) include 6 or more carbon atoms (preferably 6 to 20 carbon atoms) such as hexylamine, octylamine, 2-ethylhexylamine, decylamine, dodecylamine, myristylamine, stearylamine, and oleylamine. And an amine having an aliphatic hydrocarbon group (preferably a linear or branched alkyl group, alkenyl group, or alkynyl group).
  • the reaction between the aromatic carboxylic acid chloride and the amine can be carried out, for example, by dropping the aromatic carboxylic acid chloride into the system charged with the amine.
  • the amount of amine used is, for example, about 4 to 8 moles, preferably 4 to 6 moles per mole of aromatic carboxylic acid chloride.
  • a compound represented by the formula (1) in which n Rs are two or more different groups can be obtained.
  • the reaction between the aromatic carboxylic acid chloride and the 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 aromatic carboxylic acid chloride and amine.
  • concentration of a reaction component will become low and there exists a tendency for reaction rate to fall.
  • 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.
  • an aromatic carboxylic acid anhydride, an amine (1) and the following solvent are charged into the system and aged to form an amic acid, and then an amine (2) and a condensing agent (carbodiimide).
  • the compound represented by the formula (1) can be produced by charging and aging the salt.
  • a compound represented by the formula (1) in which n R are two or more different groups is obtained. Can do.
  • aromatic carboxylic acid anhydride examples include dianhydrides corresponding to the aromatic carboxylic acid represented by the above formula (2).
  • Examples of the amines (1) and (2) include the same examples as the amine used in the production method 1 above.
  • the amount of amine (1) used is, for example, about 2 to 4 moles, preferably 2 to 3 moles per mole of aromatic carboxylic acid anhydride.
  • 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 aromatic carboxylic anhydride.
  • R 3 and R 4 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 A cycloalkyl group; R 3 and R 4 may be the same or different. R 3 and R 4 may be bonded to each other to form a ring together with the (—N ⁇ C ⁇ N—) group.
  • Examples of the linear or branched alkyl group having 3 to 8 carbon atoms include n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, s- Examples include pentyl, t-pentyl, n-hexyl, isohexyl, s-hexyl, t-hexyl, n-heptyl, n-octyl group and the like.
  • Examples of the 3- to 8-membered cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl groups.
  • heteroatom-containing substituent examples include a nitrogen atom-containing group (for example, an amino group or a di (C 1-3 ) alkylamino group such as a dimethylamino group).
  • 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).
  • the amount of carbodiimide used is, for example, about 2 to 6 moles, preferably 2 to 4 moles per mole of aromatic carboxylic anhydride.
  • the solvent for example, it is preferable to use a proton-accepting solvent excellent in solubility of amic acid such as pyridine, triethylamine, tributylamine and the like. These can be used individually by 1 type or in mixture of 2 or more types.
  • 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 the aromatic carboxylic acid anhydride and the amine is, for example, about 0.5 to 5 hours, and the aging time of the amic acid and the 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 electronic device manufacturing solvent composition of the present invention, it is preferable to use a solvent having a property of thickening by heating and dissolving together with the compound represented by the above formula (1).
  • the SP value at 25 ° C. [(cal / cm 3 ) 0.5 : Fedors calculated value] is 7.0 to 9.2 (preferably 7.0 to 8.5, particularly preferably 7. 0 to 8.0), and a SP value [(cal / cm 3 ) 0.5 ] at 25 ° C. of 10.0 to 14.0 (preferably 10.0 to 12.0, particularly preferably 10).
  • Use of at least one solvent selected from the solvents in the range of 1.0 to 11.5) is excellent in solubility of the compound represented by the above formula (1), and is represented by the above formula (1). It is preferable in that the heating temperature at the time of dissolving the compound to be dissolved can be suppressed and the viscosity can be easily increased under mild conditions. Since a solvent having an SP value outside the above range has low solubility of the compound represented by the formula (1), the solvent composition for producing an electronic device containing the solvent has a higher temperature at the time of thickening. There is a tendency to require heating.
  • solvent examples include n-propanol (SP value: 11.8), 1,2,5,6-tetrahydrobenzyl alcohol (SP value: 11.3), diethylene glycol ethyl ether (SP value: 10.9). 3-methoxybutanol (SP value: 10.9), triacetin (SP value: 10.2), cyclopentanone (SP value: 10.0), cyclohexyl acetate (SP value: 9.2), 2-methyl Cyclohexyl acetate (SP value: 9.0), diethylene glycol ethyl ether acetate (SP value: 9.0), ethylene glycol methyl ether acetate (SP value: 9.0), diethylene glycol monobutyl ether acetate (SP value: 8.9) , Ethylene glycol monobutyl ether acetate (SP value: 8.9), Diacetate (SP value: 8.8), ethyl acetate (SP value: 8.7), propylene glycol monomethyl ether acetate (SP value: 8.9
  • the combination of the compound (1) and the solvent is not particularly limited as long as the compound (1) and the solvent are compatible, but from the viewpoint of the minimum addition amount (minimum thickening concentration), the polarity of the solvent is low (for example, the SP value is low). 7.0 to 9.2 (cal / cm 3 ) 0.5 ), a compound in which at least one of n R is an aliphatic hydrocarbon group having 8 to 20 carbon atoms (particularly preferably 18 to 20) ( It is preferable to use 1).
  • the polarity of the solvent is high (for example, the SP value is 10.0 to 14.0 (cal / cm 3 ) 0.5 )
  • at least one of n R has 6 to 12 carbon atoms (particularly preferably 6 to 12 carbon atoms). It is preferable to use the compound (1) which is an aliphatic hydrocarbon group of 8).
  • the content of the compound represented by the formula (1) in the solvent composition for producing an electronic device is, for example, about 0.1 to 50% by weight, preferably 0.5 -30% by weight, particularly preferably 0.5-10% by weight.
  • the content of the compound represented by the formula (1) in the solvent composition for producing an electronic device is, for example, 0.1 to
  • the upper limit is preferably 30 parts by weight, particularly preferably 10 parts by weight, most preferably 5 parts by weight, and the lower limit is preferably 0.5 parts by weight.
  • the solvent composition for producing an electronic device of the present invention may contain other compounds having an effect of imparting thickening.
  • Compound represented by the above formula (1) in the compound (100% by weight) having the effect of imparting all thickening properties contained in the solvent composition for producing an electronic device of the invention (when two or more compounds are contained, the total amount) Is, for example, 5% by weight or more, preferably 10% by weight or more, more preferably 30% by weight or more, particularly preferably 50% by weight or more, most preferably 80% by weight or more, and further preferably 90% by weight or more. is there.
  • the upper limit is 100% by weight.
  • the content of the solvent in the solvent composition for producing an electronic device is, for example, about 10 to 99.9% by weight, preferably 20 to 99.5% by weight, particularly preferably 30 to 99.5% by weight, most preferably 40 to 99.5% by weight.
  • the content of the solvent is below the above range, the viscosity of the paste composition becomes too high, and it may be difficult to apply to the printing method.
  • the content of the solvent exceeds the above range, it becomes difficult to obtain a paste composition having a stable gel state such as a solution by temperature change, and a highly accurate wiring pattern is formed by liquid dripping. May be difficult.
  • the solvent composition for manufacturing an electronic device of the present invention other organic solvents may be added in addition to the above solvent as long as the effect is not impaired.
  • the physical properties of the solvent composition for producing an electronic device of the present invention can be adjusted according to the application.
  • the amount of the other organic solvent added is, for example, less than 50% by weight, preferably 30% by weight or less, particularly preferably 20% by weight or less, and most preferably 10% by weight or less, based on the total amount of the solvent composition for manufacturing electronic devices. . If the content of the other organic solvent exceeds the above range, the solubility of the compound represented by the above formula (1) decreases, and it may be difficult to dissolve by heating at a mild temperature.
  • Examples of other organic solvents include cycloalkyl alcohol, cycloalkyl acetate, alkylene glycol, alkylene glycol diacetate, alkylene glycol monoether, alkylene glycol dialkyl ether, alkylene glycol monoether acetate, dialkylene glycol monoether, dialkylene glycol.
  • Examples include dialkyl ether, dialkylene glycol monoalkyl ether acetate, trialkylene glycol monoether, trialkylene glycol monoether acetate, tetrahydrofurfuryl alcohol, tetrahydrofurfuryl acetate, terpene compounds and their derivatives.
  • cycloalkyl alcohol examples include cyclopentanol, cyclohexanol, cyclooctyl alcohol, methyl cyclohexyl alcohol, ethyl cyclohexyl alcohol, propyl cyclohexyl alcohol, iso-propyl cyclohexyl alcohol, butyl cyclohexyl alcohol, iso-butyl cyclohexyl alcohol, s- Examples thereof include a 3- to 15-membered cycloalkyl alcohol optionally having a substituent such as a C 1-5 alkyl group such as butylcyclohexyl alcohol, t-butylcyclohexyl alcohol, and pentylcyclohexyl alcohol.
  • cycloalkyl acetate examples include cyclopentyl acetate, cyclooctyl acetate, ethyl cyclohexyl acetate, propyl cyclohexyl acetate, iso-propyl cyclohexyl acetate, butyl cyclohexyl acetate, iso-butyl cyclohexyl acetate, s-butyl cyclohexyl acetate, pentyl cyclohexyl acetate, and the like.
  • Examples thereof include 3- to 15-membered cycloalkyl acetate which may have a substituent such as C 1-5 alkyl group.
  • alkylene glycol examples include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and the like. Can be mentioned.
  • alkylene glycol diacetate examples include ethylene glycol diacetate, 1,3-propanediol diacetate, 1,3-butylene glycol diacetate, 1,5-pentanediol diacetate, and 1,6-hexanediol diacetate.
  • alkylene glycol monoether examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monopentyl ether, and other ethylene glycol mono C 1-5 alkyl ethers; propylene Examples include propylene glycol mono C 1-5 alkyl ethers such as glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, and propylene glycol monopentyl ether.
  • alkylene glycol dialkyl ether examples include ethylene glycol C 1-5 alkyl (straight chain) C 1- such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, ethylene glycol dibutyl ether, and ethylene glycol dipentyl ether.
  • alkyl (straight chain) ether terminal alkyl group symmetrical
  • Ethylene glycol propyl pentyl ether ethylene glycol C 1-5 alkyl such as ethylene glycol butyl pentyl ether (linear) C 1-5 alkyl (linear) ether (terminal alkyl group asymmetric); propylene glycol dimethyl ether, propylene glycol diethyl ether, Propylene glycol C 1-5 alkyl (straight chain) C 1-5 alkyl (straight chain) ether (symmetrical
  • alkylene glycol monoalkyl ether acetate examples include ethylene glycol mono C 1-5 alkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, and ethylene glycol monopentyl ether acetate.
  • a propylene glycol mono C 1-5 alkyl ether acetate such as propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monopentyl ether acetate, etc. (including isomers); ).
  • dialkylene glycol monoether examples include diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol mono C 1-5 alkyl ether such as diethylene glycol monopentyl ether; dipropylene glycol monomethyl ether, Dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol mono C 1-5 alkyl ethers such as dipropylene glycol monopentyl ether, etc. can be mentioned (including isomers). .
  • dialkylene glycol dialkyl ether examples include diethylene glycol C 1-5 alkyl (straight chain) C 1-5 alkyl (straight chain) such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, and diethylene glycol dipentyl ether.
  • Ether (symmetrical terminal alkyl group); diethylene glycol ethyl methyl ether, diethylene glycol methyl propyl ether, diethylene glycol butyl methyl ether, diethylene glycol methyl pentyl ether, diethylene glycol ethyl propyl ether, diethylene glycol butyl ethyl ether, diethylene glycol ethyl pentyl ether, diethylene glycol Call butyl propyl ether, diethylene glycol propyl pentyl ether, diethylene glycol C 1-5 alkyl (straight chain) C 1-5 alkyl ethers (straight chain) and diethylene glycol butyl pentyl ether (terminal alkyl group asymmetric); dipropylene glycol diethyl ether, di Dipropylene glycol such as propylene glycol dipropyl ether, dipropylene glycol dibutyl ether, dipropylene glycol dipentyl ether, etc.
  • dialkylene glycol monoalkyl ether acetate examples include diethylene glycol mono C 1-5 alkyl ether acetates such as diethylene glycol monomethyl ether acetate, diethylene glycol monopropyl ether acetate, and diethylene glycol monopentyl ether acetate; Examples thereof include dipropylene glycol mono C 1-5 alkyl ether acetates such as propylene glycol monopropyl ether acetate, dipropylene glycol monobutyl ether acetate and dipropylene glycol monopentyl ether acetate (including isomers).
  • trialkylene glycol monoether examples include triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monopropyl ether, triethylene glycol monobutyl ether, triethylene glycol monopentyl ether, and the like. 1-5 alkyl ether; tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol mono C 1-5 alkyl ether and tripropylene glycol mono-pentyl ether (Including isomers).
  • trialkylene glycol monoether acetate examples include triethylene glycol monomethyl ether acetate, triethylene glycol monoethyl ether acetate, triethylene glycol monopropyl ether acetate, triethylene glycol monobutyl ether acetate, and triethylene glycol monopentyl ether acetate.
  • Triethylene glycol mono C 1-5 alkyl ether acetate Triethylene glycol mono C 1-5 alkyl ether acetate; tripropylene glycol monomethyl ether acetate, tripropylene glycol monoethyl ether acetate, tripropylene glycol monopropyl ether acetate, tripropylene glycol monobutyl ether acetate, tripropylene glycol monopentyl ether acetate etc And tripropylene glycol mono C 1-5 alkyl ether acetate (including isomers).
  • terpene compound and derivatives thereof examples include terpineol, terpineol acetate, dihydroterpineol, dihydroterpinyl acetate, dihydroterpinyl propionate, limonene, menthane, and menthol.
  • the pace composition for producing an electronic device of the present invention is represented by the solvent and the formula (1) by heating and dissolving the above-mentioned solvent composition for producing an electronic device at 30 to 90 ° C. (preferably 40 to 80 ° C.).
  • the compound can be made to be compatible with each other.
  • the time required for dissolution by heating is, for example, about 3 to 60 minutes (preferably 10 to 30 minutes).
  • room temperature for example, 25 ° C. or less
  • room temperature for example, 25 ° C. or less
  • it may be gradually cooled at room temperature, or may be rapidly cooled by ice cooling or the like.
  • a conductive metal material, a semiconductor material, a magnetic material, a dielectric material, or an insulating material is further added to the electronic device manufacturing paste composition of the present invention in terms of imparting electrical characteristics.
  • the content of the conductive metal material, semiconductor material, magnetic material, dielectric material, or insulating material is about 0.1 to 90% by weight of the total amount (100% by weight) of the electronic device manufacturing paste composition.
  • 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. These can be used alone or in combination of two or more.
  • the paste composition for electronic device manufacture of this invention may contain binder resin (For example, alkyl cellulose resin, polyvinyl acetal resin, an acrylic resin, etc.), as the content, it is paste for electronic device manufacture.
  • the total amount (100% by weight) of the composition is, for example, preferably about 10% by weight or less, particularly preferably 5% by weight or less.
  • the paste composition for producing an electronic device of the present invention obtained by the above production method has a viscosity suitable for producing an electronic device by a printing method (for example, a screen printing method), and the viscosity [25 ° C., shear rate 20 (1 ] In / s) is, for example, 0.1 to 200 Pa ⁇ s, preferably 0.1 to 10 Pa ⁇ s.
  • the paste composition for manufacturing an electronic device of the present invention is used, it is applied to a surface member (for example, a ceramic substrate, a green sheet, etc.) by a printing method, dried, and then subjected to a baking process to be conductive or insulating. It is possible to form excellent wiring and coating film, and to prevent a decrease in yield due to poor formation of wiring / coating film and occurrence of delamination. Therefore, the electronic device manufacturing paste composition of the present invention is used, for example, for manufacturing capacitors, inductors, varistors, thermistors, speakers, actuators, antennas, solid oxide fuel cells (SOFC), etc. (especially multilayer ceramic capacitors). It is particularly useful.
  • SOFC solid oxide fuel cells
  • the low boiling content of the obtained crude liquid was removed by an evaporator and washed with methanol to obtain a white wet powder. Further, the obtained wet powder was recrystallized with CHCl 3 / CH 3 OH (70/30 (v / v)) to obtain 3.5 g of 1,2,4,5-benzenetetracarboxylic acid tetra (hexylamide). Obtained (yield: 67%). The structure of the reaction product was confirmed by 1 H-NMR. The evaporation temperature of the product was 308 ° C.
  • the obtained wet powder was recrystallized with CHCl 3 / CH 3 OH (70/30 (v / v)), and 1,2,4,5-benzenetetracarboxylic acid di-2-ethylhexylamide dioleylamide [ 1,2,4,5-benzenetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,5-di (oleylamide) and 1,2,4,5-benzenetetracarboxylic acid-1, 5.9 g of a mixture of 5-di (2-ethylhexylamide) -2,4-di (oleylamide)] (yield: 51%).
  • the evaporation temperature of the product was 289 ° C.
  • the system temperature was set to 50 ° C., and a solution of 3.97 g (0.011 mol) of 3,3 ′, 4,4′-benzophenonetetracarboxytetrachloride in 10 mL of chloroform was added dropwise over 0.5 hours, followed by another 4 hours. Aged. Thereafter, the low boiling content of the obtained crude liquid was removed by an evaporator and washed with methanol to obtain a pale yellow wet powder.
  • wet powder was recrystallized from CHCl 3 / CH 3 OH (70/30 (v / v)) to obtain 3,3 ′, 4,4′-benzophenonetetracarboxylic acid tetra (dodecylamide) as 2 0.4 g was obtained (yield: 27%).
  • the product evaporation temperature was 188 ° C.
  • Example 1 The thickener (1) obtained in Preparation Example 1 was added to n-decane (manufactured by Wako Pure Chemical Industries, Ltd.) as a solvent so that the thickener concentration was 0.5% by weight. A composition (1) was obtained. The obtained solvent composition (1) was heated and dissolved at a liquid temperature of 80 ° C. for 0.5 hours, allowed to cool to room temperature (25 ° C.), and thickened paste composition (1) (viscosity: 3 Pa ⁇ s). Got.
  • n-decane manufactured by Wako Pure Chemical Industries, Ltd.
  • Example 2-7 Comparative Example 1 Solvent compositions (2) to (8) were obtained in the same manner as in Example 1 except that the composition (unit: weight ratio) shown in Table 1 below was changed, and paste compositions (2) to (8) were obtained. It was.
  • ethyl cellulose (trade name “Etocel STD200”, manufactured by Nisshin Kasei Co., Ltd.), which is a polymer binder resin, was added in place of the thickener so that the resin concentration was 5% by weight. The mixture was dissolved by heating at a temperature of 80 ° C. for 3 hours and allowed to cool at room temperature (25 ° C.) to obtain a paste composition.
  • Evaporation temperature and residual ash content For each 20 mg, the temperature was measured from 20 ° C. to 400 ° C. at 10 ° C./min with TG-DTA, the weight at each temperature was measured, and the evaporation temperature (the evaporation temperature of the paste composition was 0.1 wt. And the amount of residual ash at 350 ° C. (the ratio of residual ash to the total paste composition) was evaluated (see FIG. 1).
  • the solvent composition for producing an electronic device of the present invention can form a paste composition having a viscosity suitable for forming a wiring / coating film by a printing method by heating and dissolving.
  • a highly accurate wiring pattern can be formed which is difficult to drip.
  • drying and firing can be performed at a low temperature, and the coated surface member can be prevented from being softened and deformed by being exposed to a high temperature for a long time.
  • the ash residue and volatile matter in the wiring / coating film can be remarkably reduced even after the firing process, resulting in the deterioration of electrical characteristics, wiring / coating film formation defects and delamination. Can be suppressed.
  • the solvent composition for manufacturing an electronic device of the present invention can form a fine pattern with high accuracy by each printing method, and solves the problem that the yield decreases due to poor formation of wiring / coating film or delamination. Therefore, it is extremely useful as a raw material for a paste composition for forming a wiring or coating film having excellent electrical characteristics.

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WO2016006590A1 (ja) * 2014-07-07 2016-01-14 株式会社ダイセル 増粘安定剤、及びそれを用いた増粘安定化組成物
WO2016158969A1 (ja) * 2015-04-02 2016-10-06 株式会社ダイセル 電気デバイス製造用溶剤組成物
JP2018024243A (ja) * 2016-08-05 2018-02-15 花王株式会社 三次元物体前駆体処理剤組成物
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CN112133469B (zh) * 2020-09-28 2022-03-11 长春黄金研究院有限公司 一种用于制备高温烧结导电浆料的混合有机溶剂
JP7205705B2 (ja) * 2021-03-05 2023-01-17 株式会社リコー 造形液及び造形物の製造方法

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US11326020B2 (en) 2016-08-05 2022-05-10 Kao Corporation Composition for treating three-dimensional object precursor

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