WO2022039179A1 - Encre à la résine et dispositif électronique - Google Patents

Encre à la résine et dispositif électronique Download PDF

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Publication number
WO2022039179A1
WO2022039179A1 PCT/JP2021/030115 JP2021030115W WO2022039179A1 WO 2022039179 A1 WO2022039179 A1 WO 2022039179A1 JP 2021030115 W JP2021030115 W JP 2021030115W WO 2022039179 A1 WO2022039179 A1 WO 2022039179A1
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WO
WIPO (PCT)
Prior art keywords
compound
ink
solvent
viscosity
resin
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PCT/JP2021/030115
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English (en)
Japanese (ja)
Inventor
綾子 吉田
大介 熊木
敏成 千葉
静士 時任
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国立大学法人山形大学
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Publication of WO2022039179A1 publication Critical patent/WO2022039179A1/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
    • 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
    • C09D11/10—Printing inks based on artificial resins

Definitions

  • the present invention relates to a resin ink obtained by mixing a resin with a solvent to form an ink, and an electronic device on which the resin ink is printed.
  • Print electronics the manufacturing technology of electronic devices using printing technology is called "Printed electronics” and is attracting attention as a resource-saving, low-power, low-environmental-load electronic device manufacturing technology.
  • a semiconductor material, a conductive material, an insulating material or another functional material mixed with a solvent and made into an ink (ink composition) is printed on a substrate such as a film.
  • a substrate such as a film.
  • printing methods such as screen printing, gravure offset printing, flexographic printing, and inkjet printing are used.
  • an ink composition capable of forming an optimum film formation is possible.
  • the range of viscosity of an object is fixed. Therefore, the viscosity of the ink composition is adjusted to have an appropriate range for the printing method to be used. Therefore, if the viscosity of the ink composition changes significantly, the shape of the print pattern is disturbed, the smoothness of the printed resin layer is lowered, and the like, and circuits, elements, devices, and the like cannot be formed in a desired printing state. ..
  • the inventors have found that the viscosity of the ink composition changes significantly by absorbing moisture in a specific solvent constituting the ink composition.
  • the inventors have found that in a high-viscosity ink composition (resin ink) in which a resin is dissolved in a solvent, the viscosity significantly fluctuates due to the influence of moisture absorption when a specific polar organic solvent is used, resulting in a printing state. It was found that the quality of the ink was impaired.
  • the present invention has been proposed in order to avoid deterioration of the printing state in electronic circuit manufacturing in the process in which the resin ink is used. That is, it is an object of the present invention to provide a resin ink capable of ensuring quality maintenance in a printed state even when printing in the atmosphere, and an electronic device on which the resin ink is printed.
  • the present invention has the following configurations.
  • the resin ink of the present invention is a resin ink obtained by mixing a resin material with a solvent to form an ink, and the solvent has a thickening rate when 30 parts by mass of water is added to 100 parts by mass of the solvent. It is characterized in that it is a polar organic solvent having a value of 50% or less.
  • the solvent is characterized in that the solubility of water is 500 g / L or less.
  • the solvent is a saturated cyclic compound having a carbonyl group (including one having an oxygen atom as a hetero atom in the ring skeleton) or a chain skeleton having a carbonyl group and having 5 or more carbon atoms. It is characterized by being a polar organic solvent which is a saturated chain compound (including a compound having an oxygen atom as a hetero atom in the chain skeleton).
  • the resin material is a fluororesin.
  • the electronic device of the present invention is printed with the resin ink of the present invention.
  • the present invention it is possible to provide a resin ink capable of ensuring quality maintenance in a printed state even when printing in the atmosphere, and an electronic device on which the resin ink is printed.
  • the resin ink of the present embodiment is a paste-like composition (ink composition) in which a resin material is mixed (dissolved or dispersed) in a solvent to form an ink, and is mainly used in the manufacture of electronic circuits using a printing device. , Used as an ink for printing various patterns such as desired circuit patterns on a substrate.
  • Some such resin inks include a resin material having a polar group and a polar organic solvent having excellent compatibility (or miscibility) with the resin material.
  • the polar organic solvent is, for example, a cyclic or chain type (linear or chain type) having one or more polar groups such as a carbonyl group, an ester group, a hydroxy group, a phosphoric acid group, a sulfinyl group, an amino group and an amide group. Branched chain) compound.
  • Examples of polar organic solvents are saturated cyclic compounds having a carbonyl group (including those having an oxygen atom as a hetero atom in the ring skeleton) (compounds 1 to 5 below) and saturated cyclic compounds having a nitrogen atom (compounds below). 6-8), unsaturated cyclic compounds having a carbonyl group (compounds 9 to 24 below), saturated chain compounds having a carbonyl group (including those having an oxygen atom as a hetero atom in the chain skeleton) (compounds below). 25 to 51), chain compounds having a nitrogen atom (compound 52 below), chain compounds having a phosphate group (compound 53 below), chain compounds having a sulfinyl group (compound 54 below) and the like can be mentioned.
  • the polar organic solvent in the resin ink of the present embodiment is thickened even if it absorbs moisture in order to prevent the viscosity from changing significantly due to moisture absorption in the printing process. It is a polar organic solvent that does not absorb moisture or does not easily absorb moisture. Since the degree of moisture absorption is affected by the environment and the amount of exposure to the atmosphere (printing work time), it is necessary to select a solvent having a low thickening rate even when mixed with an excessive amount of water. Specifically, a polar organic solvent having a thickening ratio of 50% or less when 30 parts by mass of water is added to 100 parts by mass of the polar organic solvent is used.
  • the "viscosity thickening rate” means the ratio of the viscosity change due to moisture absorption to the viscosity of the solvent. For example, when the viscosity of the solvent alone is Da and the viscosity after the solvent absorbs (moisture absorbs) water is Db, the thickening rate due to the absorption of the solvent is Db ⁇ Da ⁇ 100-100 (%). be.
  • the polar organic solvent used as the solvent for the resin ink includes saturated cyclic compounds having a carbonyl group (including those having an oxygen atom as a hetero atom in the ring skeleton) (for example, compounds 1 to 5). Saturated chain compounds having a carbonyl group and having 5 or more carbon atoms in the chain skeleton (including those having an oxygen atom as a hetero atom in the chain skeleton) (for example, compounds 26 to 51), chains having a phosphate group.
  • Formula compounds (eg, compound 53) and the like can be mentioned.
  • resin material examples include fluororesins (polyvinylidene fluoride trifluoride (PVDF-TrFE), polyvinylidene fluoride (PVDF), polytetrafluoroethylene (PTFE), etc.) and polyvinylphenol (PVP).
  • fluororesins polyvinylidene fluoride trifluoride (PVDF-TrFE), polyvinylidene fluoride (PVDF), polytetrafluoroethylene (PTFE), etc.
  • PVDF-TrFE polyvinylidene fluoride trifluoride
  • PVDF polyvinylidene fluoride
  • PTFE polytetrafluoroethylene
  • PVP polyvinylphenol
  • resin materials having a polar group such as an insulating resin such as a resin.
  • the weight ratio of the resin material in the resin ink varies depending on the required viscosity and the target film thickness, so there is no particular optimum value. It is preferable to select a solvent having a smaller viscosity when water is added, because it is more likely to occur.
  • Other materials to be mixed with polar organic solvents include, for example, conductive particles (eg, copper, zinc, chromium, platinum, gold, silver, aluminum, palladium, iron, cobalt, nickel, or their metal oxides, carbon.
  • conductive particles eg, copper, zinc, chromium, platinum, gold, silver, aluminum, palladium, iron, cobalt, nickel, or their metal oxides, carbon.
  • additives eg, wetting agents, dispersants, defoaming agents, adhesion promoters, corrosion inhibitors, stabilizers, surfactants, etc.
  • additives particles consisting of one or more materials such as materials
  • substrate examples of the substrate (base material) of the object to be printed on which various patterns such as circuit patterns are printed by the resin ink include flexible substrates made of resin such as polyimide, polyethylene terephthalate (PET), and polyethylene naphthalate (PEN). Examples include ceramics (alumina, aluminum nitride, etc.), glass, paper, and the like.
  • the resin ink of this embodiment is used when printing various patterns such as a desired circuit pattern on a substrate (base material).
  • Examples of electronic devices on which such resin ink (pattern) is printed include semiconductors, electronic displays, electronic circuits (print circuits, etc.), sensors, and the like.
  • Printing of this pattern is, for example, screen printing method, inkjet printing method, letterpress reversal printing method, gravure offset printing method, offset printing method, spin coating method, spray coating method, bar coating method, die coating method, slit coating method, roll coating method. It is performed by a method such as a method or a dip coat method.
  • polar organic solvents Nos. [1] to [15] shown in [Table 1] and [Table 2] Fifteen types of polar organic solvents were selected as solvent candidates for the resin ink (polar organic solvents Nos. [1] to [15] shown in [Table 1] and [Table 2]).
  • the viscosity of only the polar organic solvent is D 1
  • 30 parts by mass of ultrapure water is mixed with 100 parts by mass of the polar organic solvent.
  • the viscosity of the polar organic solvent was D 2
  • the thickening rate (D 2 ⁇ D 1 ⁇ 100-100) (%) of the polar organic solvent calculated from D 1 and D 2 was calculated.
  • Viscosity D 1 and viscosity D 2 were measured using a rotary viscometer (DV-3T: LV) manufactured by Brookfield.
  • the spindle used was a cone plate type spindle (CPA-40). Viscosity D 1 and viscosity D 2 were measured when the spindle was rotated at 50 rpm while the temperature was maintained at 25 ° C.
  • the numbers [4] (Compound 6), No. [8] (Compound 8), and No. [10] (Compound 52) are structures containing nitrogen atoms such as an amino group and an amine group, and have such a structure. It was found that the thickening rate of this compound was large.
  • Example 2 Viscosity change in the printing process of fluororesin ink
  • the two types of polar organic solvents confirmed in Experiment 1 No. [2] (Compound 3) and No. [4] (Compound 6) were each subjected to polyvinylidene fluoride trifluoride (PVDF-TrFE), which is a fluororesin.
  • PVDF-TrF ink was prepared as a fluororesin ink by mixing with a copolymer, and it was confirmed whether the viscosity of PVDF-TrF ink changed before and after printing using the adjusted PVDF-TrF ink.
  • PVDF-TrFE polyvinylidene fluoride copolymer
  • polar organic solvents No. [2] (Compound 3) and No. [4] (Compound 6).
  • two types of PVDF-TrFE ink having a resin concentration of 18 wt% were adjusted.
  • a screen printing device As a printing device, a screen printing device SSA-PC250E-IP manufactured by Ceria Co., Ltd. was used. In this printing apparatus, a mask (plate) having a printing area of 100 mm ⁇ 100 mm and a plate frame size of 320 mm ⁇ 320 mm was used, and screen printing was performed with a squeegee moving speed of 10 mm / s.
  • each of the two prepared PVDF-TrFE inks is filled in the screen printing device, and screen printing is continuously performed on the PEN substrate which is the 10 sheets to be printed (that is, 10 times of printing), and then the mask is performed.
  • the PVDF-TrFE ink remaining on the (plate) was collected and its viscosity was measured. Since the time required for printing is about 3 minutes for one printed matter, it takes about 30 to 40 minutes for 10 printed matter, during which the PVDF-TrFE ink has a working atmosphere in this printing process. It was exposed (hygroscopic) to the atmosphere inside. The temperature and humidity of this working atmosphere were 25 ° C. and 50% humidity (relative humidity) RH.
  • FIG. 1 shows the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) of the rotor.
  • the broken line a1 indicates the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) before printing (initial state) in the PVDF-TrFE ink using the polar organic solvent of No. [2] (Compound 3).
  • the solid line a2 is the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) in the state after printing 10 times in the PVDF-TrFE ink using the polar organic solvent of No. [ 2 ] (Compound 3). Is shown.
  • the broken line b1 indicates the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) before printing (initial state) in the PVDF-TrFE ink using the polar organic solvent of No. [ 4 ] (Compound 6).
  • Solid line b 2 shows the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) in the state after printing 10 times in the PVDF-TrFE ink using the polar organic solvent of No. [4] (Compound 6). There is.
  • PVDF-TrFE ink had a greater thickening in the printing process. From this, it can be seen that the PVDF-TrFE ink absorbs moisture and thickens due to the atmosphere in the working atmosphere in the printing process.
  • Example 3 Viscosity change due to moisture absorption of polyvinylphenol ink
  • the two types of polar organic solvents confirmed in Experiment 1 No. [2] (Compound 3) and No. [4] (Compound 6)) were mixed with polyvinylphenol (PVP), which is an insulating resin, respectively.
  • PVP ink was adjusted as the insulating resin ink, and it was confirmed whether or not the viscosity of the insulating resin ink changed due to moisture absorption.
  • PVP ink which is an insulating resin
  • each polar organic solvent of No. [2] (Compound 3) and No. [4] (Compound 6) is mixed with each polar organic solvent of No. [2] (Compound 3) and No. [4] (Compound 6), and the resin concentration is 10 wt%. Two types of (insulating resin ink) were adjusted.
  • the viscosities of the two adjusted PVP inks were measured before adding ultrapure water.
  • FIG. 2 the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) of the rotor is shown.
  • the broken line c 1 indicates the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) before water addition in the PVP ink using the polar organic solvent of No. [2] (Compound 3), and is a solid line.
  • c 2 indicates the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) after the addition of water in the PVP ink using the polar organic solvent of No. [2] (Compound 3).
  • the broken line d 1 indicates the viscosity (mPa ⁇ s) with respect to the rotation speed (rpm) before water addition in the PVP ink using the polar organic solvent of No. [4] (Compound 6), and the solid line d 2 is. , No. [4] (Compound 6) shows the viscosity (mPa ⁇ s) with respect to the number of revolutions (rpm) in the state after water addition in the PVP ink using the polar organic solvent.
  • the PVP ink using the hygroscopic polar organic solvent (No. [4] (Compound 6)) is more than the PVP ink using the non-hygroscopic polar organic solvent (No. [2] (Compound 3)).
  • the thickening was greater in. From this, it was found that the PVP ink also thickened by moisture absorption.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne : une encre à la résine qui est capable de garantir une préservation de qualité de l'état d'impression même si une impression est effectuée dans l'atmosphère ; et un dispositif électronique sur lequel est imprimée cette encre à la résine.　Une encre à la résine selon la présente invention est obtenue par mélange d'un matériau de résine dans un solvant pour former une encre ; et le solvant est un solvant organique polaire, dont le rapport d'épaississement est inférieur ou égal à 50 % tel que déterminé par ajout de 30 parties par masse d'eau à 100 parties par masse du solvant.
PCT/JP2021/030115 2020-08-21 2021-08-18 Encre à la résine et dispositif électronique WO2022039179A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020140200A JP2022035700A (ja) 2020-08-21 2020-08-21 樹脂インク及び電子デバイス
JP2020-140200 2020-08-21

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WO2022039179A1 true WO2022039179A1 (fr) 2022-02-24

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011001514A (ja) * 2009-06-22 2011-01-06 Teijin Chem Ltd ガラス繊維強化樹脂組成物を射出成形して得られる電気・電子機器部品
JP2011178832A (ja) * 2010-02-26 2011-09-15 Dic Corp 紫外線硬化型インクジェット記録用インク、それから得られた絶縁膜、電子素子及び電子素子の製造方法
JP2011231170A (ja) * 2010-04-26 2011-11-17 Hitachi Chem Co Ltd 絶縁体インク及びこれを用いた絶縁層、複合層、回路基板、半導体パッケージ
CN102863845A (zh) * 2012-10-11 2013-01-09 复旦大学 印制电子用银有机导电油墨
JP2015159169A (ja) * 2014-02-24 2015-09-03 出光興産株式会社 電極修飾用組成物、電極修飾方法および有機薄膜トランジスタ
WO2017080307A1 (fr) * 2015-11-12 2017-05-18 广州华睿光电材料有限公司 Composition pour l'impression de dispositifs électroniques et son application dans des dispositifs électroniques
WO2018190347A1 (fr) * 2017-04-13 2018-10-18 Jnc株式会社 Composition de résine thermodurcissable, film durci, substrat pourvu d'un film durci, composant électronique et encre pour jet d'encre
WO2019020906A1 (fr) * 2017-07-28 2019-01-31 Arkema France Procédé de préparation d'un film de polymère fluoré réticulé
JP2019109348A (ja) * 2017-12-18 2019-07-04 東洋インキＳｃホールディングス株式会社 量子ドット、量子ドット含有組成物、およびインクジェットインキ
WO2020070420A1 (fr) * 2018-10-02 2020-04-09 Arkema France Encre de polymere fluore a comportement rheologique de fluide a seuil de contrainte

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011001514A (ja) * 2009-06-22 2011-01-06 Teijin Chem Ltd ガラス繊維強化樹脂組成物を射出成形して得られる電気・電子機器部品
JP2011178832A (ja) * 2010-02-26 2011-09-15 Dic Corp 紫外線硬化型インクジェット記録用インク、それから得られた絶縁膜、電子素子及び電子素子の製造方法
JP2011231170A (ja) * 2010-04-26 2011-11-17 Hitachi Chem Co Ltd 絶縁体インク及びこれを用いた絶縁層、複合層、回路基板、半導体パッケージ
CN102863845A (zh) * 2012-10-11 2013-01-09 复旦大学 印制电子用银有机导电油墨
JP2015159169A (ja) * 2014-02-24 2015-09-03 出光興産株式会社 電極修飾用組成物、電極修飾方法および有機薄膜トランジスタ
WO2017080307A1 (fr) * 2015-11-12 2017-05-18 广州华睿光电材料有限公司 Composition pour l'impression de dispositifs électroniques et son application dans des dispositifs électroniques
WO2018190347A1 (fr) * 2017-04-13 2018-10-18 Jnc株式会社 Composition de résine thermodurcissable, film durci, substrat pourvu d'un film durci, composant électronique et encre pour jet d'encre
WO2019020906A1 (fr) * 2017-07-28 2019-01-31 Arkema France Procédé de préparation d'un film de polymère fluoré réticulé
JP2019109348A (ja) * 2017-12-18 2019-07-04 東洋インキＳｃホールディングス株式会社 量子ドット、量子ドット含有組成物、およびインクジェットインキ
WO2020070420A1 (fr) * 2018-10-02 2020-04-09 Arkema France Encre de polymere fluore a comportement rheologique de fluide a seuil de contrainte

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