WO2012077461A1 - Composition de résine photoréactive - Google Patents

Composition de résine photoréactive Download PDF

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Publication number
WO2012077461A1
WO2012077461A1 PCT/JP2011/076101 JP2011076101W WO2012077461A1 WO 2012077461 A1 WO2012077461 A1 WO 2012077461A1 JP 2011076101 W JP2011076101 W JP 2011076101W WO 2012077461 A1 WO2012077461 A1 WO 2012077461A1
Authority
WO
WIPO (PCT)
Prior art keywords
mol
penta
resin composition
photoreactive resin
ratio
Prior art date
Application number
PCT/JP2011/076101
Other languages
English (en)
Japanese (ja)
Inventor
久保田　正博
修一 砥綿
Original Assignee
株式会社村田製作所
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社村田製作所 filed Critical 株式会社村田製作所
Priority to JP2012547756A priority Critical patent/JP5447691B2/ja
Priority to CN201180041381.2A priority patent/CN103069340B/zh
Publication of WO2012077461A1 publication Critical patent/WO2012077461A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/285—Permanent coating compositions
    • H05K3/287—Photosensitive compositions
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • 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
    • G03F7/0325—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polysaccharides, e.g. cellulose
    • 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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/0073—Masks not provided for in groups H05K3/02 - H05K3/46, e.g. for photomechanical production of patterned surfaces
    • H05K3/0076—Masks not provided for in groups H05K3/02 - H05K3/46, e.g. for photomechanical production of patterned surfaces characterised by the composition of the mask
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
    • H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
    • H05K3/061—Etching masks
    • H05K3/064—Photoresists

Definitions

  • the present invention relates to a photoreactive resin composition used for forming a desired conductor pattern on a substrate surface or each substrate constituting the multilayer substrate, for example, in the production of a circuit board, a multilayer substrate, or the like. .
  • the acrylic monomer contained in the photoreactive resin composition a dipentaerythritol pentaacrylate / hexaacrylate mixture having a large number of functional groups and high sensitivity is preferably used (see Patent Document 1).
  • the main object of the present invention is to develop a coating film used for forming a desired conductor pattern on a substrate surface or each substrate constituting the multilayer substrate in the production of a circuit board or a multilayer substrate. It is providing the photoreactive resin composition excellent in the property.
  • the photoreactive resin composition according to the present invention includes (A) conductive powder, (B) an acrylic copolymer or cellulose resin containing a carboxyl group, (C) a dipentaerythritol pentaacrylate / hexaacrylate mixture, (D) a photopolymerization initiator, and a penta ratio of dipentaerythritol pentaacrylate / hexaacrylate mixture represented by penta / (penta + hexa) is 25 mol% or more, oligomerized / (penta
  • the photoreactive resin composition is characterized in that the amount of oligomerization represented by (body + hexabody + oligomerized body) is 33 mol% or less.
  • the inventors have found that the amount of hexa- and oligomerized compounds contained in the dipentaerythritol pentaacrylate / hexaacrylate mixture has an influence on the deterioration of the developability of the coating film.
  • the penta ratio of the dipentaerythritol pentamer / hexaacrylate mixture is 25 mol% or more and the oligomerization amount is 33 mol% or less, whereby the wiring formed on the substrate Even if the pattern is fine, a photoreactive resin composition having excellent coating film developability can be obtained.
  • (A) conductive powder constituting the photoreactive resin composition, (B) an acrylic copolymer or cellulose resin containing a carboxyl group, (C) dipentaerythritol Each component of the pentaacrylate / hexaacrylate mixture and (D) photopolymerization initiator will be described.
  • the conductive powder in one embodiment, Cu, Ni, Ag, Au, can be used Pt and alloys containing at least one.
  • the conductive powder may have various shapes such as a spherical shape, a flake shape, and a needle shape, but it is preferable to use a spherical shape in consideration of optical characteristics and dispersibility.
  • the average particle size of the conductive powder is preferably in the range of 1 to 5 ⁇ m.
  • the average particle diameter is smaller than 1 ⁇ m, when the same volume of conductor powder is added to the resin, the surface area of the powder increases, so that more light is blocked and the light transmittance into the paste is reduced.
  • the thickness exceeds 5 ⁇ m, the surface roughness when the conductive paste is applied is increased, and the pattern accuracy and dimensional accuracy are further reduced.
  • the composition ratio of the conductive powder in the photoreactive resin composition is preferably 30 to 50% by volume in the components excluding the organic solvent.
  • the composition ratio of the conductive powder is less than 30% by volume, the line width shrinkage or disconnection of the conductor pattern is likely to occur.
  • it exceeds 50% by volume the light transmission is impaired and sufficient light of the composition is obtained. It becomes difficult to obtain curability.
  • the acrylic copolymer containing a carboxyl group includes, for example, an unsaturated carboxylic acid and an ethylenically unsaturated compound. It can be produced by copolymerization.
  • unsaturated carboxylic acid include acrylic acid, methacrylic acid, maleic acid, fumaric acid, vinyl acetic acid, and anhydrides thereof.
  • examples of the ethylenically unsaturated compound include acrylic esters such as methyl acrylate and ethyl acrylate, methacrylic esters such as methyl methacrylate and ethyl methacrylate, and fumaric esters such as monoethyl fumarate.
  • a cellulose resin containing a carboxyl group a carboxyl group-containing cellulose derivative represented by the following chemical formula 1 or a compound having a glycidyl group and an unsaturated double bond and / or an isocyanate group in a carboxyl group-containing cellulose derivative And a compound obtained by adding a compound having an unsaturated double bond.
  • R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, —CR 2 COOH (R 2 represents an alkyl group having 2 to 4 carbon atoms, a phenyl group, or a cyclohexyl group), —C 3 H 6 represents OH or —COCH 3 , each R 1 may be the same or different and contains at least 0.1 mol of —CR 2 COOH per glucose unit.
  • the composition ratio of the acrylic copolymer or cellulose resin containing a carboxyl group is preferably 16 to 53 wt% in the total of (B) to (D). If this composition ratio is less than 16% by weight, the distribution of these resins in the coating film to be formed tends to be non-uniform, so it becomes difficult to obtain sufficient photocurability and photocuring depth. Patterning by development becomes difficult. On the other hand, if it exceeds 53% by weight, the pattern is liable to be distorted or the line width is shrunk during firing.
  • the dipentaerythritol pentaacrylate / hexaacrylate mixture is produced by esterifying dipentaerythritol with acrylic acid in the presence of an acid catalyst and an organic solvent. The esterification reaction cannot proceed 100%.
  • a partial polymerization reaction occurs during the preparation of the dipentaerythritol pentaacrylate / hexaacrylate mixture. Therefore, actually, it is composed of three types of dipentaerythritol pentaacrylate (penta), dipentaerythritol hexaacrylate (hexa), and oligomerized product.
  • the hexa-body and the oligomerized body deteriorate the developability of the coating film. Therefore, deterioration of the developability of this coating film can be prevented by controlling the penta ratio to 25 mol% or more and controlling the oligomerization amount to 33 mol% or less.
  • the penta ratio is pentamer / (penta body + hexa body), and the oligomerization amount is defined by oligomerization body / (penta body + hexa body + oligomer body).
  • examples of the acid catalyst used for esterification include sulfuric acid and paratoluenesulfonic acid.
  • examples of the organic solvent used for esterification include aromatic hydrocarbons such as toluene, benzene, and xylene, aliphatic hydrocarbons such as hexane and heptane, and ketones such as methyl ethyl ketone.
  • the composition ratio of the dipentaerythritol pentaacrylate / hexaacrylate mixture is preferably 30 to 70% by weight in the total of (B) to (D).
  • Photopolymerization initiator The photopolymerization initiator is added to start polymerization for curing the exposed area.
  • Photopolymerization initiators include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one (initiator a), 2,4-diethylthioxanthone (initiator b), ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (o-acetyloxime) (initiator c), bis (2,4,6-trimethylbenzoyl) ) -Phenylphosphine oxide (initiator d) and 1-hydroxy-cyclohexyl-phenyl-ketone (initiator e) are used in combination.
  • the content of the initiator c, ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (o-acetyloxime) is 10 to 60% by weight in the initiator is preferred. By setting it as such content, favorable solubility can be given, without increasing a required exposure amount so much.
  • the initiator c for example, Irgacure OXE02 manufactured by Ciba Specialty Chemicals can be used.
  • the composition ratio of the photopolymerization initiator is preferably 12 to 22% by weight in the total of (B) to (D).
  • an organic solvent other, in the photoreactive resin composition according to the present invention if necessary, an organic solvent, pentamethylene glycol and dipropylene glycol monomethyl ether or the like may be contained.
  • a thixotropic agent a dispersant, an antigelling agent, and a leveling agent may be used as necessary.
  • a leveling agent a special acrylic polymer is used.
  • the leveling agent is an ethyl carbitol acetate solution.
  • the SP value (solubility) of this leveling agent is preferably 8.0 to 9.5.
  • the photoreactive resin composition according to the present invention may contain inorganic powder such as glass powder and ceramic powder.
  • inorganic powder such as glass powder and ceramic powder.
  • glass powder known glass powder such as borosilicate glass can be used.
  • ceramic powder known low-temperature sintered ceramic powders such as alumina and zirconia, crystallized glass ceramics, glass composite ceramics, non-glass ceramics, and the like can be used.
  • Photoreactive resin compositions were prepared as follows and evaluated. 1. Production of Photoreactive Resin Composition
  • each material used for production of the photoreactive resin composition is as follows.
  • Polymer a After copolymerization of methacrylic acid / methyl methacrylate, 0.2 times molar amount of epoxycyclohexylmethyl methacrylate is added to methacrylic acid. An ethylenically unsaturated double bond-containing acrylic copolymer subjected to addition reaction.
  • Photopolymerization initiator Initiator a 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one
  • Initiator b 2,4-diethylthioxanthone
  • Initiator c Ethanone , 1- [9-Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (o-acetyloxime)
  • Initiator d bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide
  • Initiator e 1-hydroxy-cyclohexyl-phenyl-ketone
  • organic solvent organic solvent a pentamethylene glycol organic solvent b: di Propylene glycol monomethyl ether
  • Thixotropic agent Polyamide (solid content 70%)
  • Dispersant High molecular weight polycarboxylic acid amidoamine salt (solid content 75%)
  • Dipropylene glycol monomethyl ether dissolves the above-mentioned ceramic green sheet, but does not dissolve when a dipentaerythritol pentaacrylate / hexaacrylate mixture having a weight of 0.5 times or more is added.
  • the wiring pattern was observed, and the resolution of each sample was judged based on the finest wiring pattern obtained. That is, among the wiring patterns in which the fine wiring pattern is not connected in the space (S) and the line (L) is not divided, the thickness value of the finest wiring pattern indicates resolution. Value.
  • the paste film is exposed to an actinic ray of 500 mJ / cm 2 from an ultrahigh pressure mercury lamp through a mask drawn with a thickness of 13 ⁇ m using the paste of Sample 1 to perform an exposure process on the paste film. went.
  • coating film developability is excellent by setting the penta ratio of the dipentaerythritol pentamer / hexaacrylate mixture to 25 mol% or more and the oligomerization amount to 33 mol% or less.
  • a photoreactive resin composition that enables formation of a fine wiring pattern can be obtained.
  • the photoreactive resin composition according to the present invention when used, it is possible to form a fine wiring pattern as described above. Therefore, electronic components for high-frequency circuits such as chip coils, chip capacitors, and chip LC filters. It can be used for forming a conductor pattern for producing a multilayer substrate which is a high-frequency circuit substrate such as a high-frequency module (for example, VOC (voltage controlled oscillator)) or PLL (phase-locked loop)).
  • a high-frequency module for example, VOC (voltage controlled oscillator)
  • PLL phase-locked loop
  • a ceramic green sheet was produced by using alumina powder, and an alumina substrate was produced.
  • the invention is not limited to this, but barium oxide, aluminum oxide
  • the substrate may be manufactured using a ceramic green sheet containing a ceramic mainly composed of silica.
  • you may produce a board

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  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Ceramic Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials For Photolithography (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention a pour objet une composition de résine photoréactive qui donne un film de revêtement ayant une excellente aptitude au développement et qui est utilisée dans la production d'une carte de circuits imprimés, d'un substrat multicouche ou similaires lorsqu'un motif de conducteur souhaité est formé sur une surface de substrat ou sur chacun des substrats pour la constitution du substrat multicouche ou similaire. La composition de résine photoréactive comprend (A) une poudre électroconductrice, (B) un copolymère acrylique ou une résine cellulosique contenant chacun des groupes carboxy, (C) un mélange de pentaacrylate et d'hexaacrylate de dipentaérythritol et (D) un initiateur de photopolymérisation. La composition de résine photoréactive est caractérisée en ce que le mélange de pentaacrylate et d'hexaacrylate de dipentaérythritol (C) a une proportion de la forme penta, représentée par le rapport (forme penta)/[(forme penta)+(forme hexa)], supérieure ou égale à 25 % en moles et une teneur en oligomère, représentée par le rapport oligomère/[(forme penta)+(forme hexa)+oligomère], inférieure ou égale à 33 % en moles.
PCT/JP2011/076101 2010-12-07 2011-11-11 Composition de résine photoréactive WO2012077461A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2012547756A JP5447691B2 (ja) 2010-12-07 2011-11-11 光反応性樹脂組成物
CN201180041381.2A CN103069340B (zh) 2010-12-07 2011-11-11 光反应性树脂组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010272466 2010-12-07
JP2010-272466 2010-12-07

Publications (1)

Publication Number Publication Date
WO2012077461A1 true WO2012077461A1 (fr) 2012-06-14

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JP (1) JP5447691B2 (fr)
CN (1) CN103069340B (fr)
WO (1) WO2012077461A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014163987A (ja) * 2013-02-21 2014-09-08 Taiyo Ink Mfg Ltd 導電性樹脂組成物及び導電回路
JP2014228793A (ja) * 2013-05-24 2014-12-08 株式会社村田製作所 感光性ペースト
WO2015040908A1 (fr) * 2013-09-20 2015-03-26 東洋紡株式会社 Pâte électroconductrice photosensible, film mince électroconducteur, circuit magnétique, et écran tactile
WO2015152208A1 (fr) * 2014-04-02 2015-10-08 東洋紡株式会社 Pâte conductrice photosensible, film mince conducteur, circuit électrique, et écran tactile
JP2019168678A (ja) * 2018-03-23 2019-10-03 株式会社ノリタケカンパニーリミテド 感光性組成物とその利用

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014163987A (ja) * 2013-02-21 2014-09-08 Taiyo Ink Mfg Ltd 導電性樹脂組成物及び導電回路
JP2014228793A (ja) * 2013-05-24 2014-12-08 株式会社村田製作所 感光性ペースト
WO2015040908A1 (fr) * 2013-09-20 2015-03-26 東洋紡株式会社 Pâte électroconductrice photosensible, film mince électroconducteur, circuit magnétique, et écran tactile
WO2015152208A1 (fr) * 2014-04-02 2015-10-08 東洋紡株式会社 Pâte conductrice photosensible, film mince conducteur, circuit électrique, et écran tactile
JP2019168678A (ja) * 2018-03-23 2019-10-03 株式会社ノリタケカンパニーリミテド 感光性組成物とその利用

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JP5447691B2 (ja) 2014-03-19
JPWO2012077461A1 (ja) 2014-05-19
CN103069340A (zh) 2013-04-24
CN103069340B (zh) 2015-02-11

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