WO2018029747A1 - Composition de résine photosensible, procédé de production de motif conducteur, substrat, écran tactile et dispositif d'affichage - Google Patents

Composition de résine photosensible, procédé de production de motif conducteur, substrat, écran tactile et dispositif d'affichage Download PDF

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Publication number
WO2018029747A1
WO2018029747A1 PCT/JP2016/073280 JP2016073280W WO2018029747A1 WO 2018029747 A1 WO2018029747 A1 WO 2018029747A1 JP 2016073280 W JP2016073280 W JP 2016073280W WO 2018029747 A1 WO2018029747 A1 WO 2018029747A1
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Prior art keywords
resin composition
photosensitive resin
group
composition according
meth
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PCT/JP2016/073280
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English (en)
Japanese (ja)
Inventor
小林康宏
諏訪充史
山舖有香
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東レ株式会社
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Priority to PCT/JP2016/073280 priority Critical patent/WO2018029747A1/fr
Publication of WO2018029747A1 publication Critical patent/WO2018029747A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

Definitions

  • the present invention relates to a photosensitive resin composition, a method for producing a conductive pattern, a substrate, a touch panel, and a display.
  • the demand for miniaturization of electronic wiring has increased with the increase in the definition of displays and the miniaturization or increase in density of electronic components.
  • a method for producing a conductive pattern used for electronic wiring by using a resin composition containing conductive particles the conductive particles are brought into contact by heating after forming the pattern on the substrate.
  • a method for obtaining a pattern is common.
  • the method for forming a pattern on the substrate include a screen printing method, an ink jet method, and a photolithography method. Among them, the screen printing method and the ink jet method are not suitable for forming a fine pattern, and the photolithography method is suitable for forming the fine pattern.
  • the photolithographic method is a method of forming an exposed portion and an unexposed portion on a coating film by irradiating ultraviolet rays or the like through a photomask on which the shape of a fine wiring pattern is drawn after application and drying of the photosensitive composition. By developing it with a developer, a fine pattern is formed on the substrate. And it is a method of forming a fine electroconductive pattern by subsequent electroconductivity processing.
  • the photosensitive composition used in this method is composed of conductive particles, a photosensitive agent, a resin, and the like (Patent Document 1).
  • the present invention was devised in view of the drawbacks of the related art, and the object of the present invention is to provide a photosensitive resin composition capable of achieving both fine pattern resolution and residue suppression on a substrate. Is to provide. By using such a photosensitive resin composition, a fine conductive pattern having a very good appearance and high reliability can be obtained.
  • the present inventors have found that it is extremely effective for the photosensitive resin composition to contain the organotin compound (C) in solving the above problems.
  • this invention contains electroconductive particle (A), alkali-soluble resin (B), and an organic tin compound (C), and the primary particle diameter of the said electroconductive particle (A) is 0.7 micrometer or less.
  • a photosensitive resin composition is provided.
  • the photosensitive resin composition of the present invention it is possible to obtain a fine conductive pattern with good appearance and high reliability.
  • the photosensitive resin composition of the present invention contains conductive particles (A), an alkali-soluble resin (B) and an organotin compound (C), and the primary particle diameter of the conductive particles (A) is 0.00. It is 7 ⁇ m or less.
  • the photosensitivity in the photosensitive resin composition may be positive photosensitivity or negative photosensitivity, but is preferably negative photosensitivity.
  • Conductive particles (A) examples include gold (Au), silver (Ag), copper (Cu), nickel (Ni), tin (Sn), bismuth (Bi), lead (Pb), and zinc (Zn). , Palladium (Pd), platinum (Pt), aluminum (Al), tungsten (W), molybdenum (Mo), and the like.
  • metal fine particles containing at least one element selected from the group consisting of gold, silver, copper, nickel, tin, bismuth, lead, zinc, palladium, platinum, aluminum and carbon are preferable. More preferably.
  • the primary particle diameter of the conductive particles (A) needs to be 0.7 ⁇ m or less in order to form a fine conductive pattern having desired conductivity.
  • the primary particle diameter of the conductive particles (A) can be calculated from an average value of the particle diameters of 100 primary particles randomly selected using a scanning electron microscope.
  • the particle diameter of each primary particle can be calculated from the average value obtained by measuring the major and minor diameters of the primary particles.
  • the primary particle diameter of the conductive particles (A) is preferably 10 to 200 nm, more preferably 10 to 60 nm.
  • the conductive particle (A) is preferably a particle whose surface is coated with a carbon simple substance and / or a carbon compound. Due to the presence of a layer (hereinafter referred to as “surface coating layer”) that covers the surface of the conductive particles (A) made of a simple substance of carbon and / or a carbon compound, the fusion of the conductive particles (A) with each other at a low temperature. Wear can be suppressed.
  • a method of coating the particle surface with a carbon simple substance and / or a carbon compound for example, a method of contacting a reactive gas when producing conductive particles (A) by a thermal plasma method (Japanese Patent Laid-Open No. 2007-138287) Gazette).
  • the surface of the conductive particles (A) is preferably completely covered. However, as long as this object is achieved, the presence of partially incompletely covered particles is allowed.
  • the average thickness of the surface coating layer is preferably 0.1 to 10 nm. Within this range, the fine pattern processability can be improved by suppressing the fusion of the conductive fine particles, and desired conductivity can be exhibited by heat treatment at a temperature of 300 ° C. or lower.
  • the average thickness of the surface coating layer is determined by measuring the mass loss of the conductive particles (A) surface-coated with the carbon simple substance and / or the carbon compound by the thermobalance, and assuming that all the values are due to carbon combustion.
  • the average thickness of the surface coating layer can be calculated from the particle diameter, assuming that the carbon density is 2.0. It is assumed that the conductive particles (A) whose particle diameter (Dp) is known are coated with carbon with an average thickness A ( ⁇ m). Let n be the number of particles coated with carbon.
  • W 1 (g) is the mass weighed first in the thermobalance measurement
  • W 2 (g) is the mass where carbon is completely blown
  • ⁇ is the density of the conductive particles (A)
  • Dp is If W 2 is known, n can be calculated.
  • W 2 ⁇ / 6 ⁇ Dp 3 ⁇ ⁇ n
  • the average thickness A of a surface coating layer is computable from the following formula
  • the content of the conductive particles (A) in the photosensitive resin composition is preferably 65 to 95% by mass, more preferably 70 to 95% by mass, and 70 to 90% by mass. Is more preferable. By containing within the range, pattern workability and expression of electroconductivity can be made compatible.
  • the total solid content means all components excluding the solvent among the components contained in the photosensitive resin composition.
  • the ratio of the conductive particles (A) in the total solid content can be calculated by quantitatively analyzing all the components of the photosensitive resin composition. In addition, the ratio of each component mentioned later can be calculated by the same method.
  • the method for analyzing all components of the photosensitive resin composition is as follows.
  • the photosensitive resin composition is diluted with an organic solvent, and its outline is examined by 1 H-NMR measurement, GC measurement, and GC / MS measurement.
  • the photosensitive resin composition is extracted with an organic solvent and then centrifuged to separate soluble and insoluble components.
  • the insoluble matter is extracted with a highly polar organic solvent and then centrifuged to further separate the soluble and insoluble matters.
  • IIv Perform IR measurement, 1 H-NMR measurement and GC / MS measurement on the mixture of the soluble components obtained in (ii) and (iii) above. Further, the above mixed solution is collected by GPC.
  • the obtained fraction is subjected to IR measurement and 1 H-NMR measurement. Moreover, about this fraction, GC measurement, GC / MS measurement, pyrolysis GC / MS measurement, and MALDI / MS measurement are performed as needed.
  • V Perform IR measurement or TOF-SIMS measurement on the insoluble matter obtained in (iii) above. When it is confirmed that organic substances are present, pyrolysis GC / MS or TPD / MS measurement is performed.
  • Vi By comprehensively determining the measurement results of (i), (iv) and (v) above, the content of each component contained in the photosensitive resin composition can be determined. In addition, as a highly polar organic solvent used by said (iii), chloroform or methanol is preferable.
  • the alkali-soluble resin (B) is generally obtained by copolymerizing a compound containing a carboxyl group and another monomer.
  • the alkali-soluble resin (B) is preferably a (meth) acrylic copolymer.
  • the (meth) acrylic copolymer refers to a copolymer containing at least a (meth) acrylic monomer as a copolymerization component.
  • Examples of the (meth) acrylic monomer include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, and sec-butyl.
  • a compound having a carbon-carbon double bond can be used as the copolymer component other than the (meth) acrylic monomer.
  • examples of such compounds include aromatic vinyl compounds such as styrene, p-methylstyrene, o-methylstyrene, m-methylstyrene, and ⁇ -methylstyrene, (meth) acrylamide, N-methylol (meth) acrylamide, or Amide unsaturated compounds such as N-vinylpyrrolidone, (meth) acrylonitrile, allyl alcohol, vinyl acetate, cyclohexyl vinyl ether, n-propyl vinyl ether, i-propyl vinyl ether, n-butyl vinyl ether, i-butyl vinyl ether, 2-hydroxyethyl Examples include vinyl ether or 4-hydroxybutyl vinyl ether.
  • Examples of the copolymer component that imparts alkali solubility to the alkali-soluble resin (B) include a carboxyl group-containing compound such as (meth) acrylic acid, itaconic acid, crotonic acid, maleic acid or fumaric acid, or acids thereof. Anhydrides are mentioned.
  • a (meth) acrylic copolymer in order to increase the speed of the curing reaction by exposure of the photosensitive resin composition, a (meth) acrylic compound having a carbon-carbon double bond in the side chain or molecular end It is preferable to use a copolymer.
  • the functional group having a carbon-carbon double bond include a vinyl group, an allyl group, and a (meth) acryl group.
  • Examples of the compound having a glycidyl group and a carbon-carbon double bond include glycidyl (meth) acrylate, allyl glycidyl ether or glycidyl ethyl acrylate, crotonyl glycidyl ether, glycidyl crotonate or glycidyl isocrotonate.
  • Examples of the compound having an isocyanate group and a carbon-carbon double bond include (meth) acryloyl isocyanate or (meth) acryloyloxyethyl isocyanate.
  • the alkali-soluble resin (B) is preferably an alkali-soluble resin having an acid dissociable group.
  • the alkali-soluble resin having an acid dissociable group is generally obtained by copolymerizing a compound having a carboxyl group and a compound having an acid dissociable group. More specific examples include copolymerization of a (meth) acrylic acid compound containing a carboxyl group and a (meth) acrylic acid ester having an acid dissociable group.
  • the acid dissociable group is preferably an organic group having 4 to 15 carbon atoms, more preferably an organic group having 6 to 15 carbon atoms. If the acid dissociable group has less than 4 carbon atoms, it will be vaporized at a low temperature after desorption, so that large bubbles are generated in the film, preventing the conductive particles (A) from contacting each other, and the conductivity deteriorates. There is a case. On the other hand, if the number of carbon atoms of the acid dissociable group exceeds 15, the dissociable group may remain in the film after desorption, preventing contact between the conductive particles (A), and the conductivity may be deteriorated. is there.
  • the acid-dissociable group of the acid-dissociable group is an organic group having 6 to 15 carbon atoms, even if bubbles are generated in the film, they can be easily eliminated by post-baking and have good conductivity. A conductive pattern can be formed.
  • Examples of the acid dissociable group include a tert-butyl group, a tert-butoxycarbonyl group, a benzyl group, a methyladamantyl group, and a tetrahydropyranyl group.
  • Examples of the (meth) acrylic acid ester having an acid dissociable group include 1-methyladamantyl (meth) acrylate, tert-butyl (meth) acrylate, benzyl (meth) acrylate or tetrahydropyrani (meth) acrylate. Le.
  • the content of the alkali-soluble resin (B) is preferably in the range of 5 to 30% by mass with respect to the total solid content in consideration of the expression of photosensitivity.
  • the alkali-soluble resin (B) is preferably an alkali-soluble resin obtained by radical copolymerization of a compound having an acid dissociable group in an amount of 20 to 80 mol%.
  • (meth) acrylic acid ester having an acid dissociable group is preferably contained in an alkali-soluble resin as a monomer component in an amount of 20 to 80 mol%.
  • the carboxylic acid equivalent of the alkali-soluble resin (B) is preferably 200 to 1,400 g / mol, more preferably 400 to 1,000 g / mol.
  • the carboxylic acid equivalent of the acrylic resin can be calculated by measuring the acid value.
  • the double bond equivalent of the alkali-soluble resin (B) is preferably 150 to 10,000 g / mol because both hardness and crack resistance can be achieved at a high level.
  • the double bond equivalent of the acrylic resin can be calculated by measuring the iodine value.
  • the weight average molecular weight (Mw) of the alkali-soluble resin (B) is preferably 1,000 to 100,000 in terms of polystyrene measured by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the organotin compound (C) refers to an organic acid salt of tin or a compound in which at least one carbon atom is bonded to a tin atom.
  • organic tin compounds include organic acid salts such as tin 2-ethylhexanoate or tin dilaurate, or dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate, dibutyltin bis (2-ethylhexyl mercaptoacetate), dibutyltin bis (Isooctyl mercaptoacetate), dioctyltin diacetate, dioctyltin dilaurate, dioctyltin maleate, dimethyltin diacetate, dimethyltin dilaurate, dimethyltin maleate, diphenyltin diacetate, diphenyltin dilaurate, diphenyltin dilau
  • the organotin compound (C) is preferably a compound represented by the general formula (1).
  • R 1 and R 2 each independently represent an organic group
  • X 1 and X 2 each independently represent a monovalent anion.
  • X 1 and X 2 are linked to each other. It doesn't matter.
  • the organic group for R 1 and R 2 include an alkyl group, an alkenyl group, and an aryl group.
  • the alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an octyl group.
  • alkenyl group include a vinyl group, an acryloxypropyl group, and a methacryloxypropyl group.
  • a aryl group a phenyl group, a tolyl group, or a naphthyl group is mentioned, for example.
  • Examples of the monovalent anion in X 1 and X 2 include fluoride ion, chloride ion, bromide ion, iodide ion, hydroxide ion, nitrate ion or carboxylate ion.
  • Specific examples of the compound represented by the general formula (1) include, for example, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate, dibutyltin bis (2-ethylhexyl mercaptoacetate), dibutyltin bis (isooctyl mercaptoacetate), and diacetic acid.
  • the proportion of the organotin compound (C) in the total solid content is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, and 0.1 to 5% by mass. More preferably it is.
  • the content of the organotin compound (C) is 0.01% by mass or more, the effect of suppressing residues on the substrate becomes more remarkable.
  • the content of the organotin compound (C) is 10% by mass or less, the conductivity is high and a fine pattern can be formed.
  • the photosensitive resin composition of the present invention may contain a dispersant. By containing the dispersant, the conductive particles (A) can be stably present in the photosensitive resin composition.
  • the dispersant is preferably an amine-based one.
  • examples of commercially available amine-based dispersants include DISPERBYK (registered trademark) 106, 108, 112, 116, 142, 145, 166, 180, 2001, 2008, 2022, 2150, 6919, or 21116 (all of which are Big Chemie). (Made by Japan) or Efka (registered trademark) 4300, 4400, 4401, 4403, 4406, 4510, 4570, 4800, 5054, 5055, or 5207 (all are made by BASF).
  • the dispersant preferably has an acrylic block copolymer structure.
  • acrylic block copolymer structure examples include DISPERBYK (registered trademark) 2001, 2008, 2022, 2150, 6919, or 21116, or Efka (registered trademark) 4300.
  • the dispersion of the conductive particles (A) is good, finer pattern processing is possible, and the contact and fusion of the conductive particles (A) proceed.
  • 1 to 7 parts by mass is preferable with respect to 100 parts by mass in total of the conductive particles (A) and other particles described later.
  • the photosensitive resin composition of the present invention may contain a photopolymerization initiator. By containing a photopolymerization initiator, negative photosensitivity can be imparted to the photosensitive resin composition.
  • Examples of the photopolymerization initiator include acetophenone compounds, benzophenone compounds, benzoin ether compounds, ⁇ -aminoalkylphenone compounds, thioxanthone compounds, organic peroxides, imidazole compounds, titanocene compounds, and triazine compounds.
  • an acyl phosphine oxide compound, a quinone compound or an oxime ester-based compound may be mentioned, but an oxime ester-based compound having a high sensitivity even if added in a small amount is preferable, and an oxime ester-based compound having a carbazole skeleton is more preferable.
  • Examples of the oxime ester compound having no carbazole skeleton include Irgacure (registered trademark) OXE01 (manufactured by BASF), and examples of the oxime ester compound having a carbazole skeleton include Irgacure (registered trademark) OXE02 ( BASF), Adekaoptomer (registered trademark) N1919 (produced by ADEKA) or Adeka Arcles (registered trademark) NCI-831 (produced by ADEKA).
  • the photosensitive resin composition of the present invention may contain a solvent.
  • solvent examples include propylene glycol monomethyl ether, propylene glycol monobutyl ether, 2-heptanol, cyclohexanol, cyclopentanol, 2-butanol, 2-pentanol, t-butanol, diacetone alcohol, ⁇ -terpineol, 2- Methyl hydroxyisoisobutyrate, ethyl 2-hydroxyisoisobutyrate, propylene glycol monoethyl ether acetate, ethyl acetoacetate, methyl acetoacetate, methyl-3-methoxypropionate, 3-methyl-3-methoxybutylacetate, cyclopentanone, Cyclohexanone, benzyl ethyl ether, dihexyl ether, acetonyl acetone, isophorone, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl male
  • the photosensitive resin composition of the present invention may contain particles other than (A) conductive fine particles for improving dispersibility and controlling conductivity.
  • examples of the other particles include metal fine particles or metal oxide fine particles, organic pigments, or inorganic pigments that are not surface-coated.
  • the particle diameter of these other particles is preferably 10 to 100 nm.
  • the particle diameter is less than 10 nm, the use of a dispersant for stabilizing the dispersion increases, and it may be difficult to obtain desired conductivity.
  • the particle diameter exceeds 100 nm, the resolution of the pattern is lowered, and it may be difficult to form an ultrafine pattern of 5 ⁇ m or less.
  • These other particles are preferably carbon black, which contributes to conductivity control.
  • Examples of carbon black include MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14 (all of which are manufactured by Mitsubishi Chemical Corporation), # 52, 47, 45, 45L, 44, 40. 33, 32, 30, 25, 20, 10, 5, 95, 85 or 260 (all are manufactured by Mitsubishi Chemical Corporation), Special Black 100, 250, 350 or 550 (all are manufactured by Evonik Degussa) Or Printex95, 90, 55, 45, 40, P, 60, L6, L, 300, 30, ES23, 9, ES22, 35, 25, 200, A or G (all of which are manufactured by Evonik Degussa) be able to.
  • MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14 or Special Black 100, 250, 350, or 550 having a pH value of 4 or less is preferable.
  • the pH value of carbon black can be measured according to JIS K5101.
  • the photosensitive resin composition of the present invention may contain a photoacid generator and / or a thermal acid generator.
  • the alkali-soluble resin (B) is an alkali-soluble resin having an acid-dissociable group, decomposition of the acid-dissociable group is promoted by the generated acid, and the heat treatment temperature under air can be lowered.
  • thermal acid generator that is a compound that generates an acid by heat
  • examples of the thermal acid generator that is a compound that generates an acid by heat include SI-60, SI-80, SI-100, SI-110, SI-145, SI-150, SI-60L, SI-80L, SI-100L, SI-110L, SI-145L, SI-150L, SI-160L, SI-180L or SI-200 (all of which are manufactured by Sanshin Chemical Industry Co., Ltd.), 4-hydroxyphenyldimethylsulfonium, benzyl -4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-acetylphenylmethylsulfonium, 2-methylbenzyl-4-benzoyloxyphenylmethylsulfonium, or methanesulfonic acid thereof Salt
  • trifluoromethanes Hong salts include camphorsulfonate or p- toluenesul
  • Phenylmethylsulfonium or a methanesulfonate, trifluoromethanesulfonate, camphorsulfonate or p-toluenesulfonate can be preferably used.
  • the content of the thermal acid generator in the photosensitive resin composition is such that the decomposition of the acid dissociable group in the alkali-soluble resin having an acid dissociable group is promoted and the contact between the conductive particles (A) is hindered.
  • 0.01 to 20 parts by mass is preferable with respect to 100 parts by mass of the alkali-soluble resin (B).
  • the acid generated from the photoacid generator that is a compound that generates an acid by light is preferably a strong acid such as perfluoroalkylsulfonic acid or p-toluenesulfonic acid in order to promote the decomposition of the acid dissociable group.
  • Examples of the photoacid generator include SI-101, SI-105, SI-106, SI-109, PI-105, PI-106, PI-109, NAI-100, NAI-1002, NAI-1003, and NAI. -1004, NAI-101, NAI-105, NAI-106, NAI-109, NDI-101, NDI-105, NDI-106, NDI-109, PAI-01, PAI-101, PAI-106 or PAI-1001 (All as above, manufactured by Midori Chemical Co., Ltd.), SP-077 or SP-082 (all as described above, manufactured by ADEKA), TPS-PFBS (manufactured by Toyo Gosei Co., Ltd.), CGI-MDT or CGI -NIT (all of which are manufactured by Ciba Japan) or WPAG-281, WPAG-336, WPAG 339, WPAG-342, WPAG-344, WPAG-350, WPAG-370, W
  • disassembly of the acid dissociable group in the alkali-soluble resin which has an acid dissociable group is accelerated
  • 0.01 to 20 parts by mass is preferable with respect to 100 parts by mass of the alkali-soluble resin (B).
  • a thermal acid generator and a photo acid generator may be used in combination.
  • the photosensitive resin composition of the present invention contains a photoacid generator
  • the photosensitive resin composition may further contain a sensitizer.
  • the sensitizer is preferably vaporized by heat treatment or discolored by light irradiation even when it remains in the cured film, and more preferably discolored by light irradiation from the viewpoint of high resolution in pattern processing. preferable.
  • coumarin such as 3,3′-carbonylbis (diethylaminocoumarin)
  • anthraquinone such as 9,10-anthraquinone
  • benzophenone 4,4 ′.
  • -Aromatic ketones such as dimethoxybenzophenone, acetophenone, 4-methoxyacetophenone or benzaldehyde or biphenyl, 1,4-dimethylnaphthalene, 9-fluorenone, fluorene, phenanthrene, triphenylene, pyrene, anthracene, 9-phenylanthracene, 9-methoxyanthracene 9,10-diphenylanthracene, 9,10-bis (4-methoxyphenyl) anthracene, 9,10-bis (triphenylsilyl) anthracene, 9,10-dimethoxyanthracene 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene (DPA; manufactured by Kawasaki Kasei Co., Ltd.), 9,10-dibutoxyanthracene (DBA; manufactured by Kawasaki Kasei Co., Ltd.), 9,10-dipenta Examples include
  • the sensitizer that is vaporized by the heat treatment a sensitizer that sublimates, evaporates, or thermally decomposed by thermal decomposition by the heat treatment is preferable.
  • the vaporization temperature of the sensitizer is preferably 150 to 300 ° C. because it does not vaporize at the pre-baking temperature, but decomposes and vaporizes at the time of thermosetting to contact and fuse the conductive particles (A).
  • the sensitizer is preferably an anthracene-based compound in that it can achieve high sensitivity and high resolution, and dimerizes and fades when irradiated with light, and is stable to heat.
  • 9,10-disubstituted An anthracene compound is preferable, and from the viewpoint of improving the solubility of the sensitizer and the reactivity of the photodimerization reaction, the 9,10-dialkoxy anthracene compound represented by the general formula (2) is preferable. Further preferred.
  • R 3 ⁇ R 10 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an alkoxy group, an alkenyl group, an ethynyl group, an aryl group or an acyl group or an organic group which they are substituted
  • R 11 And R 12 each independently represents an alkoxy group substituted with an alkoxy group having 1 to 20 carbon atoms or other organic group.
  • Examples of the alkyl group for R 3 to R 10 include a methyl group, an ethyl group, and an n-propyl group.
  • the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentyloxy group.
  • alkenyl group examples include a vinyl group, an acryloxypropyl group, and a methacryloxypropyl group.
  • aryl group a phenyl group, a tolyl group, or a naphthyl group is mentioned, for example.
  • acyl group examples include an acetyl group.
  • R 3 to R 10 are preferably hydrogen or an organic group having 1 to 6 carbon atoms, and R 3 , R 6 , R 7 and R 10 More preferably, is hydrogen.
  • Examples of the alkoxy group in this case include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, methoxyethoxy group, 1-methoxy-2-propoxy group or 1-acetyl-2-propoxy group.
  • a propoxy group or a butoxy group is preferable from the viewpoint of the solubility of the compound and the fading reaction due to photodimerization.
  • the sensitization effect for sensitizing the photoacid generator is sufficient, and contact between the conductive particles (A) is not hindered, and higher conductivity is obtained. Therefore, the amount is preferably 0.001 to 20 parts by weight, more preferably 0.005 to 15 parts by weight with respect to 100 parts by weight of the alkali-soluble resin (B).
  • the photosensitive resin composition of the present invention may contain a pigment and / or dye that absorbs visible light as long as the contact and fusion between the conductive particles (A) are not inhibited. Visible light reflection of the conductive pattern after post-baking can be suppressed because the photosensitive resin composition contains a pigment and / or dye that absorbs visible light.
  • pigments that absorb visible light include lactam pigments, perylene pigments, phthalocyanine pigments, isoindoline pigments, diaminoanthraquinone pigments, dioxazine pigments, indanthrone pigments, carbon black, and inorganic pigments. It is done.
  • Examples of blue pigments include C.I. I. Pigment Blue (hereinafter “PB”) 15, PB15: 1, PB15: 2, PB15: 3, PB15: 4, PB15: 5, PB15: 6, PB16 or PB60.
  • Examples of purple pigments include C.I. I. Pigment violet (hereinafter referred to as “PV”) 19, PV23 or PV37.
  • Examples of red pigments include C.I. I. Pigment red (hereinafter “PR”) 149, PR166, PR177, PR179, PR209, or PR254.
  • Examples of the green pigment include C.I. I. Pigment Green (hereinafter referred to as “PG”) 7, PG36 or PG58.
  • Examples of yellow pigments include C.I. I.
  • Pigment yellow (hereinafter “PY”) 150, PY138, PY139, or PY185.
  • the black pigment include furnace black such as HCF, MCF, LFF, RCF, SAF, ISAF, HAF, XCF, FEF, GPF or SRF, thermal black such as FT or MT, carbon such as channel black or acetylene black.
  • black or lactam pigments for example, “Irgaphor” (registered trademark) black S0100CF; manufactured by BASF).
  • carbon black excellent in heat resistance, light resistance and visible light absorption is preferable, and furnace black or lactam pigment is more preferable from the viewpoint of conductivity and dispersibility.
  • Examples of carbon black include MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14 (all of which are manufactured by Mitsubishi Chemical Corporation), # 52, 47, 45, 45L, 44, 40. 33, 32, 30, 25, 20, 10, 5, 95, 85 or 260 (all are manufactured by Mitsubishi Chemical Corporation), Special Black 100, 250, 350 or 550 (all are manufactured by Evonik Degussa) Or Printex 95, 90, 55, 45, 40, P, 60, L6, L, 300, 30, ES23, 9, ES22, 35, 25, 200, A or G.
  • MA77, 7, 8, 11, 100, 100R, 100S, 230, 220, or 14, or Special Black 100, 250, 350, or 550 having a pH value of 4 or less is preferable.
  • the pH value of carbon black can be measured according to JIS K5101.
  • the addition amount of the pigment having absorption in visible light in the photosensitive resin composition is preferably 0.1 to 10% by mass with respect to the total solid content in the composition.
  • dyes that absorb visible light include, for example, ferrocene dyes, fluorenone dyes, perylene dyes, triphenylmethane dyes, coumarin dyes, diphenylamine dyes, quinacridone dyes, quinophthalone dyes, phthalocyanine dyes or Xanthene dyes may be mentioned, but black dyes having excellent heat resistance, light resistance and absorption of visible light are preferable.
  • VALIFAST registered trademark
  • VALIFAST registered trademark
  • VALIFAST registered trademark
  • VALIFAST registered trademark
  • Black 3830 VALIFAST (registered trademark) Black 3830
  • NUBIAN registered trademark
  • Black PA- 2802 or OIL Black 860 is preferred.
  • the addition amount of the dye having absorption in visible light in the photosensitive resin composition is preferably 0.1 to 10% by mass with respect to the total solid content in the composition.
  • the photosensitive resin composition of the present invention contains an acrylic monomer within a range that does not impede contact and fusion between the conductive particles (A) from the viewpoint of adjusting the photosensitive performance and improving pattern processability. It doesn't matter.
  • acrylic monomer examples include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol penta (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, or diester.
  • Pentaerythritol penta (meth) acrylate or an alkyl modified product, an alkyl ether modified product or an alkyl ester modified product thereof may be mentioned.
  • the photosensitive resin composition of the present invention may further contain an adhesion improver, a surfactant, a polymerization inhibitor or the like, if necessary.
  • adhesion improving agent examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-amino Ethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl
  • silane coupling agents such as trimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane.
  • the surfactant examples include an anionic surfactant such as ammonium lauryl sulfate or polyoxyethylene alkyl ether sulfate triethanolamine, a cationic surfactant such as stearylamine acetate or lauryltrimethylammonium chloride, lauryldimethylamine oxide, or lauryl.
  • Amphoteric surfactants such as carboxymethylhydroxyethyl imidazolium betaine
  • nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether or sorbitan monostearate, fluorosurfactants or silicon surfactants Can be mentioned.
  • the addition amount of the surfactant in the photosensitive resin composition is preferably 0.001 to 10% by mass with respect to the entire composition in order to improve the coating property and the uniformity of the coating film surface, and 0.01 More preferably, it is ⁇ 1% by mass.
  • the addition amount is less than 0.001% by mass, the effect of coating property and coating surface uniformity may be insufficient.
  • the addition amount exceeds 10% by mass, coating film defects such as cissing and dents and particle aggregation may occur.
  • polymerization inhibitor examples include hydroquinone, catechol, phosphorus, sulfur, amine or hindered phenol compounds.
  • hydroquinone and catechol-based compounds are preferably hydroquinone-based or catechol-based compounds that do not inhibit solubility in solvents and pigment dispersion stability.
  • Hydroquinone, tert-butylhydroquinone, 2,5-bis ( 1,1,3,3-tetramethylbutyl) hydroquinone, 2,5-bis (1,1-dimethylbutyl) hydroquinone, catechol or tert-butylcatechol is more preferred.
  • the photosensitive resin composition of the present invention is produced using a dispersing machine such as a ball mill, a sand grinder, a 3 roll mill, a mild disperser, or a medialess disperser.
  • a dispersing machine such as a ball mill, a sand grinder, a 3 roll mill, a mild disperser, or a medialess disperser.
  • a dispersing machine such as a ball mill, a sand grinder, a 3 roll mill, a mild disperser, or a medialess disperser.
  • the dispersion of the conductive particles (A) is preferably dispersed using a mild disperser or a medialess disperser, and is dispersed using a medialess disperser. Is more preferable.
  • the dispersion of the conductive particles (A) may be a dispersion machine such as a mild disperser Nanogetter (registered trademark) (Ashizawa Finetech Co., Ltd.) or a high-pressure wet medialess atomizer Nanomizer (Nanomizer Co., Ltd.). It is produced by dispersing conductive particles (A) in an organic solvent.
  • the method for producing a conductive pattern of the present invention comprises a coating step of applying the photosensitive resin composition of the present invention on a substrate surface, a pre-baking step of drying the substrate, a step of exposing and developing it to form a pattern (exposure) Step, development step) and a post-baking step for post-baking the same.
  • Examples of the substrate used in the coating process include a silicon wafer, a ceramic substrate, and an organic substrate.
  • the ceramic substrate include glass substrates such as soda glass, non-alkali glass, borosilicate glass, and quartz glass, alumina substrates, aluminum nitride substrates, and silicon carbide substrates.
  • the organic substrate include an epoxy substrate, a polyetherimide resin substrate, a polyether ketone resin substrate, a polysulfone resin substrate, a polyimide film, and a polyester film.
  • Examples of the method for coating the photosensitive resin composition of the present invention on a substrate surface include coating using a spin coater, bar coater, blade coater, roll coater, die coater, calendar coater or meniscus coater, screen printing, and spraying. Application or dip coating may be mentioned.
  • drying method in the pre-baking step examples include hot plate, hot air dryer (oven), vacuum drying, vacuum drying, and drying by infrared irradiation.
  • the prebaking temperature and time may be appropriately determined depending on the composition of the photosensitive resin composition and the thickness of the coating film to be dried, but it is preferably heated at a temperature range of 50 to 150 ° C. for 10 seconds to 30 minutes.
  • the ultimate pressure for drying under reduced pressure is preferably 10 to 200 Pa, more preferably 30 to 100 Pa.
  • the light source used in the exposure process for example, j-ray, i-line, h-line or g-line of a mercury lamp is preferable.
  • alkaline substance used for the alkaline developer in the development step examples include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, or aqueous ammonia, ethylamine, or n-propyl.
  • inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, or aqueous ammonia, ethylamine, or n-propyl.
  • Primary amines such as amines, secondary amines such as diethylamine or di-n-propylamine, tertiary amines such as triethylamine or methyldiethylamine, tetraalkylammonium hydroxides such as tetramethylammonium hydroxide (TMAH) , Quaternary ammonium salts such as choline, triethanolamine, diethanolamine, monoethanolamine, alcoholamines such as dimethylaminoethanol or diethylaminoethanol, or pillows And organic alkalis such as cyclic amines such as piperidine, 1,8-diazabicyclo [5,4,0] -7-undecene, 1,5-diazabicyclo [4,3,0] -5-nonane or morpholine.
  • a water-soluble organic solvent such as ethanol, ⁇ -butyrolactone, dimethylformamide, or N-methyl-2-pyrrolidone may be appropriately added thereto.
  • a surfactant such as a nonionic surfactant to these alkaline developers.
  • drying method in the post-bake process examples include the same as those in the pre-bake process.
  • the post-baking atmosphere, temperature, and time may be appropriately determined depending on the composition of the photosensitive resin composition and the thickness of the coating film to be dried, but in the temperature range of 100 to 300 ° C. for 5 to 120 minutes. It is preferable to heat.
  • the conductive pattern is formed in a mesh shape on the substrate, it can be used as a transparent conductive wiring provided in a touch panel, a display panel such as liquid crystal or organic EL, or a wearable terminal.
  • the conductive pattern is not transparent, if the pattern width is large, the user of the device can visually recognize the wiring. For this reason, it is preferable that the width
  • [Conductive particles (A)] (A-1) Silver particles having a primary particle size of 0.7 ⁇ m (manufactured by Mitsui Metals) (A-2) Silver particles having a primary particle diameter of 0.2 ⁇ m (manufactured by Mitsui Metals) (A-3) Silver particles (manufactured by Nisshin Engineering Co., Ltd.) having an average thickness of the surface carbon coating layer of 1 nm and a primary particle diameter of 40 nm.
  • Irgacure registered trademark
  • OXE02 oxime ester compound
  • Example 1 In a clean bottle, 25.0 g of a solution (40% by mass) of alkali-soluble resin (B-1), 1.0 g of organotin compound (C-1), 1.5 g of photopolymerization initiator, 5.5 g An acrylic monomer and 2.0 g of a dispersant were added and mixed with an auto-revolution mixer “Awatori Nertaro” (registered trademark) (ARE-310; manufactured by Shinkey Co., Ltd.) to obtain a resin solution 1.
  • B-1 alkali-soluble resin
  • C-1 organotin compound
  • photopolymerization initiator 1.5 g
  • An acrylic monomer and 2.0 g of a dispersant were added and mixed with an auto-revolution mixer “Awatori Nertaro” (registered trademark) (ARE-310; manufactured by Shinkey Co., Ltd.) to obtain a resin solution 1.
  • the photosensitive resin composition 1 was screen-printed on an alkali-free glass substrate (OA-10; manufactured by Nippon Electric Glass Co., Ltd.) so that the dry film thickness was 2 ⁇ m, and the obtained coating film was heated to 100 ° C. Pre-baked for 5 minutes in a hot air oven. The obtained pre-baked film was exposed with a gap of 50 ⁇ m through a gray scale mask for sensitivity measurement using PLA with an ultrahigh pressure mercury lamp as a light source. Thereafter, using an automatic developing device (AD-2000; manufactured by Takizawa Sangyo Co., Ltd.), the film was shower-developed with a 0.2 mass% sodium carbonate aqueous solution for 30 seconds and then rinsed with water for 30 seconds.
  • AD-2000 automatic developing device
  • the exposure amount (hereinafter referred to as “optimum exposure amount”) for forming a 5 ⁇ m line-and-space pattern in a one-to-one width was defined as sensitivity.
  • the exposure amount was measured with an I-line illuminometer. Then, the minimum pattern size after development at the optimum exposure amount was measured to obtain the resolution.
  • the photosensitive resin composition 1 was separately screen-printed on a non-alkali glass substrate so that the dry film thickness was 2 ⁇ m, and the obtained coating film was pre-baked in a hot air oven at 100 ° C. for 5 minutes.
  • the obtained prebaked film was exposed with a gap of 50 ⁇ m through a photomask having a rectangular translucent pattern (10 mm ⁇ 15 mm) using PLA as a light source with an ultrahigh pressure mercury lamp.
  • the film was shower-developed with a 0.2% by mass aqueous sodium carbonate solution for 30 seconds and then rinsed with water for 30 seconds.
  • post-baking was performed at 230 ° C. for 30 minutes (in air) using an oven (“IHPS-222”; manufactured by Espec Corp.) to obtain a volume resistivity evaluation pattern.
  • the surface resistance value ⁇ s ( ⁇ / ⁇ ) measured with a surface resistance measuring machine (Loresta (registered trademark) -FP; manufactured by Mitsubishi Yuka Co., Ltd.), and a surface roughness shape measuring machine The film thickness t (cm) measured by (Surfcom (registered trademark) 1400D; manufactured by Tokyo Seimitsu Co., Ltd.) was measured, and the volume resistivity ( ⁇ ⁇ cm) was calculated by multiplying both values.
  • substrate was evaluated by transmittance
  • the transmittance at 400 nm before and after film formation was measured for the unexposed part using a spectrophotometer (U-3410; manufactured by Hitachi, Ltd.).
  • the transmittance change represented by the formula (T 0 -T) / T 0 was calculated, where T 0 is the transmittance before film formation and T is the transmittance after film formation. If the change in transmittance is less than 1%, it can be determined that the effect of suppressing residue is sufficient.
  • Table 1 shows the measured resolution and the calculated volume resistivity and transmittance change results.
  • Example 2 A solution of 160.0 g of conductive particles (A), 50.0 g of alkali-soluble resin (B-2) (40% by mass), 4.0 g of a dispersant and 486.0 g of PGMEA were added at 1200 rpm using a homogenizer. Then, the mixture was mixed for 30 minutes, and further dispersed using a high-pressure wet medialess atomizer Nanomizer (Nanomizer Co., Ltd.) to obtain a silver particle dispersion 2. 350.0 g of silver particle dispersion 2, 1.0 g of organotin compound (C-1), 1.5 g of photopolymerization initiator, 5.5 g of acrylic monomer and 142.0 g of PGMEA are mixed and stirred. Thereby, the photosensitive resin composition 2 was obtained.
  • the photosensitive resin composition 2 was spin-coated on an alkali-free glass substrate using a spin coater at 500 rpm for 10 seconds and 1000 rpm for 4 seconds, and then pre-baked at 90 ° C. for 2 minutes using a hot plate. Thus, a prebaked film having a thickness of 1 ⁇ m was obtained. The obtained prebaked film was exposed and developed in the same manner as in Example 1, and the volume resistivity and transmittance change were calculated. The evaluation results are shown in Table 1.
  • Example 1 A photosensitive resin composition having the composition shown in Table 1 was obtained in the same manner as in Example 1, and each photosensitive resin composition was evaluated in the same manner as in Example 1. The evaluation results are shown in Table 1.
  • Example 6 to 8 and 10 to 12 and Comparative Example 2 A photosensitive resin composition having the composition shown in Table 1 was obtained in the same manner as in Example 2, and each photosensitive resin composition was evaluated in the same manner as in Example 2. The evaluation results are shown in Table 1.
  • Comparative Examples 1 and 2 did not contain an organic tin compound, and thus the effect of suppressing residue was insufficient.
  • the photosensitive resin composition of the present invention can be suitably used for forming a conductive pattern used for a touch panel, a display, an image sensor, organic electroluminescence illumination, a solar cell, or the like.

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  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)

Abstract

L'invention concerne une composition de résine photosensible permettant à la fois de garantir la résolution d'un motif fin et de supprimer l'accumulation de résidus sur un substrat. La composition de résine photosensible comprend des particules conductrices (A), une résine soluble dans les alcalis (B) et un composé d'organo-étain (C), la taille de particule primaire des particules conductrices (A) étant inférieure ou égale à 0,7 µm.
PCT/JP2016/073280 2016-08-08 2016-08-08 Composition de résine photosensible, procédé de production de motif conducteur, substrat, écran tactile et dispositif d'affichage WO2018029747A1 (fr)

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PCT/JP2016/073280 WO2018029747A1 (fr) 2016-08-08 2016-08-08 Composition de résine photosensible, procédé de production de motif conducteur, substrat, écran tactile et dispositif d'affichage

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005011584A (ja) * 2003-06-17 2005-01-13 Taiyo Ink Mfg Ltd 光硬化性樹脂組成物及びプラズマディスプレイパネル用前面基板
WO2005116763A1 (fr) * 2004-05-31 2005-12-08 Fujifilm Corporation Méthode de formation de modèle de greffe, matérial de modèle de greffe, méthode de lithographie, méthode de formation de modèle conducteur, modèle conducteur, processus de fabrication de filtre couleur, filtre couleur et processus de fabrication de microlentille
JP2010070614A (ja) * 2008-09-17 2010-04-02 Sekisui Chem Co Ltd マイクロパターン形成用材料、マイクロパターン複合材及びその製造方法並びに微小３次元構造基板の製造方法
JP2010129344A (ja) * 2008-11-27 2010-06-10 Mitsubishi Chemicals Corp 下引き層用組成物、有機薄膜パターニング用基板、有機電界発光素子、有機ｅｌ表示装置および有機ｅｌ照明
JP2011122109A (ja) * 2009-12-14 2011-06-23 Nippon Kayaku Co Ltd 感光性樹脂及びそれを含有する感光性樹脂組成物
JP2013543993A (ja) * 2010-11-19 2013-12-09 エルジー・ケム・リミテッド アクリレート系化合物を含む感光性組成物
WO2014136738A1 (fr) * 2013-03-07 2014-09-12 東レ株式会社 Substrat de matrice noire

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005011584A (ja) * 2003-06-17 2005-01-13 Taiyo Ink Mfg Ltd 光硬化性樹脂組成物及びプラズマディスプレイパネル用前面基板
WO2005116763A1 (fr) * 2004-05-31 2005-12-08 Fujifilm Corporation Méthode de formation de modèle de greffe, matérial de modèle de greffe, méthode de lithographie, méthode de formation de modèle conducteur, modèle conducteur, processus de fabrication de filtre couleur, filtre couleur et processus de fabrication de microlentille
JP2010070614A (ja) * 2008-09-17 2010-04-02 Sekisui Chem Co Ltd マイクロパターン形成用材料、マイクロパターン複合材及びその製造方法並びに微小３次元構造基板の製造方法
JP2010129344A (ja) * 2008-11-27 2010-06-10 Mitsubishi Chemicals Corp 下引き層用組成物、有機薄膜パターニング用基板、有機電界発光素子、有機ｅｌ表示装置および有機ｅｌ照明
JP2011122109A (ja) * 2009-12-14 2011-06-23 Nippon Kayaku Co Ltd 感光性樹脂及びそれを含有する感光性樹脂組成物
JP2013543993A (ja) * 2010-11-19 2013-12-09 エルジー・ケム・リミテッド アクリレート系化合物を含む感光性組成物
WO2014136738A1 (fr) * 2013-03-07 2014-09-12 東レ株式会社 Substrat de matrice noire

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