JP2000330272A - Photosensitive resin composition for photosensitive film and photosensitive film - Google Patents
Photosensitive resin composition for photosensitive film and photosensitive filmInfo
- Publication number
- JP2000330272A JP2000330272A JP14247699A JP14247699A JP2000330272A JP 2000330272 A JP2000330272 A JP 2000330272A JP 14247699 A JP14247699 A JP 14247699A JP 14247699 A JP14247699 A JP 14247699A JP 2000330272 A JP2000330272 A JP 2000330272A
- Authority
- JP
- Japan
- Prior art keywords
- photosensitive
- meth
- resin composition
- weight
- acid value
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 43
- 239000002253 acid Substances 0.000 claims abstract description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 32
- 238000009826 distribution Methods 0.000 claims abstract description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- 239000000470 constituent Substances 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims description 42
- 229920005989 resin Polymers 0.000 claims description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000758 substrate Substances 0.000 abstract description 34
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000004925 Acrylic resin Substances 0.000 abstract description 3
- 229920000178 Acrylic resin Polymers 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 20
- 239000003513 alkali Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000018109 developmental process Effects 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- -1 alkyl methacrylate Chemical compound 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010558 suspension polymerization method Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- SCEFCWXRXJZWHE-UHFFFAOYSA-N 1,2,3-tribromo-4-(2,3,4-tribromophenyl)sulfonylbenzene Chemical compound BrC1=C(Br)C(Br)=CC=C1S(=O)(=O)C1=CC=C(Br)C(Br)=C1Br SCEFCWXRXJZWHE-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical group CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 125000006538 C11 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102100031083 Uteroglobin Human genes 0.000 description 1
- 108090000203 Uteroglobin Proteins 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
Abstract
Description
ćļ¼ļ¼ļ¼ļ¼ć[0001]
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ę§ćć£ć«ć ć«é¢ćććBACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photosensitive resin composition for a photosensitive film used for manufacturing a printed wiring board and the like, and a photosensitive film using the same.
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ććć2. Description of the Related Art As a resist material used for manufacturing a printed wiring board, a photosensitive resin composition and a photosensitive film using the same are widely known. This photosensitive resin composition usually comprises a binder resin such as a high acid value resin, a crosslinking agent such as a polyfunctional (meth) acrylate, a photopolymerization initiator, and a dye, and an additive such as a heat stabilizer. is there. This photosensitive resin composition is coated on a polyester film or the like and dried to produce a photosensitive film having a photosensitive layer composed of the photosensitive resin composition.
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ć¦ē¾åććåŗęæäøć«ć¬ćøć¹ćććæć¼ć³ćå½¢ęćććThe manufacture of a printed wiring board using this photosensitive film is usually performed as follows. A photosensitive film is laminated on a polished or chemical-treated copper-clad substrate with the photosensitive layer facing the substrate, and a negative mask is overlaid thereon to expose and cure the photosensitive film. After exposure, development is carried out using an aqueous solution of an alkali such as a 0.5 to 3% by weight aqueous sodium carbonate solution to form a resist pattern on the substrate.
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ćę¹ę³ć§ćććAs a method of forming a wiring pattern on a substrate, there are a tenting method and a plating method. Tenting method is a method in which through holes for chip mounting are protected with a resist at the same time as the formation of a resist pattern, etching is performed to form a wiring pattern, and the resist is peeled off using an aqueous sodium hydroxide solution or the like. is there. On the other hand, in the plating method, copper is deposited on a substrate on which no through-hole or resist pattern is formed by electroplating, the copper is protected by solder plating, the resist pattern is peeled off, and solder is applied using aqueous ammonia or the like. In this method, a portion other than the plating is etched to form a wiring pattern.
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ććThe wiring pattern thus formed is perpendicular to the substrate and the line width is reduced, so that the density of the wiring pattern is increased and the printed wiring board is formed. The size can be reduced. However, since the resolution of the photosensitive film using the conventional photosensitive resin composition was not less than 20 Ī¼m, the resist pattern after development and the wiring pattern after etching were reduced to 20 Ī¼m.
It has been difficult to form a line with a line width of Ī¼m or less stably.
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ććŖļ¼ććøćļ¼ć®å®å®ę§ć®é¢ć§äøå©ć§ćć£ćć[0006] The resist pattern and the wiring pattern
In order to stably mold with a line width of 0 Ī¼m or less, a method using a liquid resist agent as a resist material has been adopted. However, the liquid resist agent is disadvantageous as compared with the photosensitive film in terms of controlling the thickness of the film formed on the substrate after coating, and exposing the circuit (etch cut) and the stability of fog (bleeding).
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ć¼ćć®åē“ē¾åć®å®å®ę§ćććććććć«ććć¤ć³ćć¼
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ććØććåé”ććć£ććTherefore, in order to increase the resolution of the photosensitive film, the solubility of the binder resin is increased by increasing the acid value of the binder resin used in the photosensitive resin composition or decreasing the molecular weight thereof, thereby improving the developing property. The idea of improving is made. However, when the acid value of the binder resin is increased or the molecular weight is decreased, there is a problem that the adhesiveness of the resist pattern to the copper foil on the substrate is deteriorated. In particular, the line width of the resist pattern is 30 Ī¼m.
Below m, the erosion of the aqueous alkali solution tends to cause peeling of the bonded portion between the resist pattern and the substrate and dents in a convex pattern (hereinafter referred to as relief),
There is a problem that a resist pattern perpendicular to the substrate cannot be formed stably. On the other hand, if the molecular weight of the binder resin is increased in order to improve the adhesiveness of the resist pattern to the substrate and the stability of the vertical development of the relief in an alkaline aqueous solution, the solubility of the uncured portion in the alkaline aqueous solution decreases during resist development. However, there is a problem that developability is deteriorated.
ćļ¼ļ¼ļ¼ļ¼ććć£ć¦ćę¬ēŗęć«ćććčŖ²é”ćÆćč§£ååŗ¦ć
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ę§ćć£ć«ć ćęä¾ććććØć«ććć[0008] Therefore, the object of the present invention is to provide a resolution,
Provided is a photosensitive resin composition for a photosensitive film, which has excellent adhesion to a substrate and can stably form a resist pattern formed after development with a line width of 20 Ī¼m or less, and a photosensitive film using the same. It is in.
ćļ¼ļ¼ļ¼ļ¼ć[0009]
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ļ¼ć”ćæļ¼ć¢ćÆćŖć¬ć¼ćć¾ććÆēē“ ę°ļ¼ļ¼ćļ¼ļ¼ć®ć¢ć«ć
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ęåć®ćć©ć³ć¹ćććŖćć”ęŖē”¬åéØåć®ć¢ć«ć«ćŖę°“ęŗ¶ę¶²
ć«åƾććęŗ¶č§£ę§ćØē”¬åéØåć®ć¢ć«ć«ćŖę°“ęŗ¶ę¶²ć«åƾććå®
å®ę§ļ¼čęµøé£ę§ļ¼ć®ćć©ć³ć¹ććććŖććć¬ćøć¹ćććæ
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ć§å®å®ćć¦å½¢ęććććØćć§
ććććØćč¦åŗććę¬ēŗęć«č³ć£ććThe present inventors have made intensive studies on the molecular weight distribution of the binder resin and the balance between the hydrophilic group component and the lipophilic group component in the binder resin, and as a result, have narrowed the molecular weight distribution of the binder resin. By doing so, the solubility of the binder resin in an aqueous alkali solution is improved, and benzyl (meth) acrylate or an alkyl (meth) acrylate having an alkyl group having 12 to 18 carbon atoms is used as a constituent monomer having a lipophilic group. Introduces a good balance between the hydrophilic group component and the lipophilic group component in the binder resin, that is, the balance between the solubility of the uncured portion in an alkaline aqueous solution and the stability of the cured portion in an alkaline aqueous solution (erosion resistance). Found that a resist pattern can be formed stably with a line width of 20 Ī¼m or less. It has completed the present invention.
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ćē¹å¾“ćØćććThat is, the photosensitive resin composition for a photosensitive film of the present invention is a photosensitive resin composition for a photosensitive film containing an acrylic high acid value resin, wherein the acrylic high acid value resin is: (Meth) acrylic acid and 2 to 50% by weight of benzyl (meth) acrylate or alkyl (meth) acrylate having an alkyl group having 12 to 18 carbon atoms
And an acrylic high acid value resin having a weight average molecular weight of 8,000 to 20.
Wherein the molecular weight distribution (Mw / Mn) of the acrylic high acid value resin is 2.5 or less. Further, the photosensitive film of the present invention has a photosensitive layer comprising the photosensitive resin composition for a photosensitive film.
ćļ¼ļ¼ļ¼ļ¼ć[0011]
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ćäøååćØćŖććććććććBEST MODE FOR CARRYING OUT THE INVENTION The acrylic high acid value resin in the present invention refers to an acrylic resin having an acid value enough to dissolve in an aqueous alkaline solution used for developing a resist pattern. The acid value of the acrylic high acid value resin is not particularly limited as long as it is an acid value enough to dissolve in an alkaline aqueous solution, and is, for example, 80 mgKOH / g or more, and preferably 120 mgKOH / g or more. Acid value is 80m
If it is less than gKOH / g, the solubility in an aqueous alkali solution may be insufficient.
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ć«ćŖę°“ęŗ¶ę¶²ćøć®ęŗ¶č§£ę§ćä½äøććē¾åę§ćęŖććŖććThe weight average molecular weight of the acrylic high acid value resin in the present invention is in the range of 8,000 to 200,000, preferably in the range of 20,000 to 90,000. If the weight average molecular weight is less than 8,000, the solubility in an alkaline aqueous solution becomes too high, and peeling of a resist pattern or the like occurs. If it exceeds 200,000, the solubility in an alkaline aqueous solution is reduced, and the developability is deteriorated. .
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ć®ęåćå¢ćććććć¬ćøć¹ćććæć¼ć³ć®ć¢ć«ć«ćŖę°“ęŗ¶
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åéćč”ØććThe molecular weight distribution (Mw / Mn) of the acrylic high acid value resin in the present invention is 2.5 or less, preferably 1.5 to 2.0. Molecular weight distribution (Mw / Mn)
If it exceeds 2.5, the high molecular weight component in the acrylic high acid value resin increases, so that the solubility in an aqueous alkali solution decreases, and at the same time, the low molecular weight component in the acrylic high acid value resin also increases. As a result, the stability of the vertical development of the relief of the resist pattern with respect to the aqueous alkali solution decreases, and it becomes impossible to form a resist pattern perpendicular to the substrate.
Here, Mw is a weight average molecular weight, and Mn is a number average molecular weight.
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ć¾ććÆć¢ć«ćć«ć”ćæćÆćŖć¬ć¼ććęććThe acrylic high acid value resin in the present invention comprises:
It is a copolymer containing (meth) acrylic acid and benzyl (meth) acrylate or an alkyl (meth) acrylate having an alkyl group having 12 to 18 carbon atoms as constituent monomers. Here, (meth) acrylic acid refers to acrylic acid and / or methacrylic acid, and benzyl (meth) acrylate refers to benzyl acrylate and / or
Or benzyl methacrylate, and alkyl (meth) acrylate is an alkyl acrylate and / or
Or refers to alkyl methacrylate.
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ć©ćēććććććććć(Meth) in acrylic high acid value resin
The ratio of the acrylic acid component is not particularly limited as long as the acid value of the acrylic high acid value resin is dissolved in the aqueous alkali solution, and is not particularly limited, but is, for example, 12 to 28% by weight, and preferably 18 to 25% by weight. %. If the proportion of the (meth) acrylic acid component is less than 12% by weight, the solubility in the aqueous alkali solution may decrease. If the proportion of the (meth) acrylic acid component exceeds 28% by weight, the solubility in the aqueous alkaline solution may be reduced. It may be too high, and the resist pattern may be peeled off.
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ć§ćććThe proportion of the benzyl (meth) acrylate component or the alkyl (meth) acrylate component having an alkyl group having 12 to 18 carbon atoms in the acrylic high acid value resin is 2 to 50% by weight. If the proportion of these components is less than 2% by weight, the adhesion of the resist pattern to the substrate and the stability of the vertical development of the relief in an alkaline aqueous solution are reduced, and a resist pattern perpendicular to the substrate cannot be formed. On the other hand, when the proportion of these components exceeds 50% by weight, the solubility in an aqueous alkali solution decreases,
Developability deteriorates. The benzyl (meth) acrylate component is preferably 15 to 35% by weight, and has 12 to
The content of the alkyl (meth) acrylate component having 18 alkyl groups is preferably 30 to 50% by weight.
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ć®ēÆå²ć§ćććThe acrylic high acid value resin of the present invention may contain another vinyl monomer as a constituent monomer. Examples of the other vinyl monomers include alkyl having a C1 to C11 alkyl group such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate. (Meth) acrylate; hydroxyalkyl (meth) acrylate such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate; ethylene glycol (meth) acrylate, butylene glycol (meth) acrylate, vinyl acetate, ) Acrylonitrile, styrene and the like. The ratio of the other vinyl monomer component in the acrylic high acid value resin is in the range of 0 to 70% by weight.
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ćå¾ćććē¹ćććęøęæéåę³ć儽é©ć«ēØćććććIn the present invention, the acrylic high acid value resin is
It is manufactured by a known polymerization method such as a suspension polymerization method, an emulsion polymerization method, and a solution polymerization method. Among them, the molecular weight distribution (Mw / M
Polymer having n) of 2.5 or less (polymer having a narrow molecular weight distribution)
The suspension polymerization method is suitably used because it is easy to obtain.
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ē©ćÆćäøčæ°ć®ć¢ćÆćŖć«ē³»é«é
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éåę§ć®ę¶ę©å¤ćå
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åććććThe photosensitive resin composition for a photosensitive film of the present invention contains the above-mentioned acrylic high acid value resin. If necessary, a photopolymerizable crosslinking agent, a photopolymerization initiator,
Additives and the like are blended.
ćļ¼ļ¼ļ¼ļ¼ćę¶ę©å¤ćØćć¦ćÆćéåøøćęå
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ćć¼ć«ćććć³ććŖć¢ćÆćŖć¬ć¼ććććć©ćØćć¬ć³ć°ćŖ
ć³ć¼ć«ćøć¢ćÆćŖć¬ć¼ćććøćć³ćæćØćŖć¹ćŖćć¼ć«ćććµ
ć¢ćÆćŖć¬ć¼ććļ¼ļ¼ļ¼āćććµć³ćøćŖć¼ć«ćøć¢ćÆćŖć¬ć¼
ćććøćØćć¬ć³ć°ćŖć³ć¼ć«ćøć¢ćÆćŖć¬ć¼ćēć®å¤ä¾”ć¢ć«
ć³ć¼ć«ć®ć¢ćÆćŖć«é
øćØć¹ćć«ļ¼ććŖć”ććć¼ć«ćććć³
ććŖć°ćŖć·ćøć«ćØć¼ćć«ććŖć¢ćÆćŖć¬ć¼ććć«ć«ććØć
ćć·ćøć¢ćÆćŖć¬ć¼ćēć®ćØććć·ć¢ćÆćŖć¬ć¼ćļ¼ć¦ć¬ćæ
ć³ć¢ćÆćŖć¬ć¼ćććć¹ćć§ćć¼ć«ļ¼”ććŖćŖćć·ćØćć¬ć³
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ć¼ććŖć©ćęćććććThe crosslinking agent may be any one usually used in a photosensitive resin composition, such as trimethylolpropane triacrylate, tetraethylene glycol diacrylate, dipentaerythritol hexaacrylate, 1,6- Acrylic esters of polyhydric alcohols such as hexanediol diacrylate and diethylene glycol diacrylate; epoxy acrylates such as trimethylolpropane triglycidyl ether triacrylate and cardepoxy diacrylate; urethane acrylate, bisphenol A polyoxyethylene dimethacrylate, and polyethylene glycol diacrylate Acrylate and the like.
ćļ¼ļ¼ļ¼ļ¼ćå
éåéå§å¤ćØćć¦ćÆćéåøøćęå
ę§ęعč
ēµęē©ć«ēØćććć¦ćććć®ć§ććć°ćććä¾ćć°ćć
ć³ć¾ćć§ćć³ćć¢ć³ćć©ććć³ćććŖććµć³ćć³ćć¢ć»
ććć§ćć³ēć®čŖå°ä½ćŖć©ćęćććććę·»å å¤ćØćć¦
ćÆćä¾ćć°ćęęćé”ęćē±éåē¦ę¢å¤ćé
ćć¬ć¼ćå
å¤ćåæ
č¦ć«åæćć¦ćć£ć©ć¼ćę¶ę³”å¤ćŖć©ćęćććććThe photopolymerization initiator may be any one usually used in a photosensitive resin composition, and examples thereof include derivatives such as benzophenone, anthraquinone, thioxanthone and acetophenone. Examples of the additive include a dye, a pigment, a thermal polymerization inhibitor, a copper chelating agent, and, if necessary, a filler and an antifoaming agent.
ćļ¼ļ¼ļ¼ļ¼ćć¢ćÆćŖć«ē³»é«é
øä¾”ęعčć®é
åéćÆćē¹ć«é
å®ćÆćććŖćććä¾ćć°ćęå
ę§ćć£ć«ć ēØęå
ę§ęعč
ēµęē©ļ¼ļ¼ļ¼éééØć«åƾćć¦ļ¼ļ¼ćļ¼ļ¼éééØć§ććć
儽ć¾ćććÆļ¼ļ¼ćļ¼ļ¼éééØć§ćććć¢ćÆćŖć«ē³»é«é
øä¾”
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åéćļ¼ļ¼éééØęŖęŗć§ćÆćć¢ć«ć«ćŖę°“ęŗ¶ę¶²ćø
ć®ęŗ¶č§£ę§ćä½äøćććććććććļ¼ļ¼éééØćč¶
ćć
ćØćē”¬åå¾ć®ę©ę¢°ēē©ę§ćäøååćØćŖććććććććThe amount of the acrylic high acid value resin is not particularly limited, but is, for example, 40 to 80 parts by weight based on 100 parts by weight of the photosensitive resin composition for a photosensitive film.
Preferably it is 50 to 70 parts by weight. If the blending amount of the acrylic high acid value resin is less than 40 parts by weight, the solubility in an aqueous alkali solution may decrease, and if it exceeds 80 parts by weight, mechanical properties after curing may be insufficient. .
ćļ¼ļ¼ļ¼ļ¼ćę¶ę©å¤ć®é
åéćÆćē¹ć«éå®ćÆćććŖć
ććä¾ćć°ćęå
ę§ćć£ć«ć ēØęå
ę§ęعčēµęē©ļ¼ļ¼ļ¼
éééØć«åƾćć¦ļ¼ļ¼ćļ¼ļ¼éééØć§ććć儽ć¾ćććÆļ¼
ļ¼ćļ¼ļ¼éééØć§ćććę¶ę©å¤ć®é
åéćļ¼ļ¼éééØęŖ
ęŗć§ćÆćē”¬åå¾ć®ę©ę¢°ēē©ę§ćäøååćØćŖćććććć
ććļ¼ļ¼éééØćč¶
ćććØćć¢ć«ć«ćŖę°“ęŗ¶ę¶²ćøć®ęŗ¶č§£ę§
ćä½äøććč§£ååŗ¦ćä½äøćććććććććThe amount of the crosslinking agent is not particularly limited. For example, the photosensitive resin composition 100 for a photosensitive film may be used.
30 to 50 parts by weight with respect to parts by weight, preferably 3 parts by weight.
5 to 45 parts by weight. If the amount of the crosslinking agent is less than 30 parts by weight, the mechanical properties after curing may be insufficient. If the amount exceeds 50 parts by weight, the solubility in an alkaline aqueous solution may decrease, and the resolution may decrease. is there.
ćļ¼ļ¼ļ¼ļ¼ćå
éåéå§å¤ć®é
åéćÆćē¹ć«éå®ćÆćć
ćŖćććä¾ćć°ćęå
ę§ćć£ć«ć ēØęå
ę§ęعčēµęē©ļ¼
ļ¼ļ¼éééØć«åƾćć¦ļ¼ćļ¼éééØć§ććć儽ć¾ćććÆļ¼
ćļ¼éééØć§ćććå
éåéå§å¤ć®é
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ęŗć§ćÆćęåŗ¦ćäøååćØćŖććććććććļ¼éééØć
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ćććØćē”¬åē©ćä½ååéćØćŖć£ć¦ććććŖćććć
ććććThe blending amount of the photopolymerization initiator is not particularly limited. For example, the photosensitive resin composition 1 for a photosensitive film may be used.
3 to 8 parts by weight, preferably 5 to 100 parts by weight.
ļ¼6 parts by weight. If the amount of the photopolymerization initiator is less than 3 parts by weight, the sensitivity may be insufficient. If the amount exceeds 8 parts by weight, the cured product may have a low molecular weight and become brittle.
ćļ¼ļ¼ļ¼ļ¼ćę¬ēŗęć®ęå
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ćć«ēć®ćć£ć«ć äøć«å½¢ęćććć®ć§ćććę¬ēŗęć®ę
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ę§ęعčēµęē©ćå”åøććä¹¾ē„ć
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ć«ć ć§äæč·ććććØć«ćć£ć¦å¾ććććęå
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ēØęå
ę§ęعčēµęē©ćÆćć”ćć«ćØćć«ć±ćć³ļ¼ļ¼ļ¼„
ļ¼«ļ¼ćć¢ć»ćć³ćć”ćæćć¼ć«ćć¤ć½ćććć«ć¢ć«ć³ć¼
ć«ćć”ććć·ćććć«ć¢ć»ćć¼ćēć®ęŗ¶å¤ć§ęŗ¶ę¶²ē¶ć«ć
ćå¾ćå”åøć«ēØćć¦ććććThe photosensitive film of the present invention is obtained by forming a photosensitive layer comprising the above-mentioned photosensitive resin composition for a photosensitive film on a film of polyester or the like. The photosensitive film of the present invention may be obtained by applying the above-described photosensitive resin composition for a photosensitive film on a film of polyester or the like, drying the film, and, if necessary, protecting the photosensitive layer with a film of polyolefin or the like. Obtained by The photosensitive resin composition for a photosensitive film is methyl ethyl ketone (ME
K), a solution such as acetone, methanol, isopropyl alcohol, methoxypropyl acetate, or the like, may be used as a solution after coating.
ćļ¼ļ¼ļ¼ļ¼ćęå
層ćÆćåŗęæäøć«ē©å±¤ććććć¬ćć¹ćÆ
ćéćć¦ē
§å°ćććē“«å¤ē·ēć®ę“»ę§å
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ććå¾ćć¢ć«ć«ćŖę°“ęŗ¶ę¶²ēć®ē¾åę¶²ć«ćć£ć¦ē¾åććć
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ēÆććć»ćć³ć©ć³ććć”ćæć«ćć©ć¤ćć©ć³ćēćēØćć
ćććThe photosensitive layer is laminated on a substrate, is cured by actinic rays such as ultraviolet rays irradiated through a negative mask, and is developed by a developing solution such as an aqueous alkali solution.
This is used as a resist pattern. As a light source, a high-pressure mercury lamp, a xenon lamp, a metal halide lamp, or the like is used.
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øä¾”ęعčćę§ęćć
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øć®å²åćå¢ćććć¢ć«ć«ćŖę°“ęŗ¶ę¶²ć«
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ćććæć¼ć³ćå®å®ćć¦å½¢ęć§ćććIn such a photosensitive resin composition for a photosensitive film, the molecular weight distribution of the acrylic high acid value resin is narrow, and benzyl (meth) acrylate or a compound having 12 to 12 carbon atoms is contained in the acrylic high acid value resin. Since a high lipophilic group such as an alkyl (meth) acrylate having an alkyl group of 18 is included, the proportion of (meth) acrylic acid constituting the acrylic high acid value resin is increased, and the solubility in an aqueous alkali solution is increased. However, the formed resist pattern is less likely to be eroded by an aqueous alkaline solution. Therefore, even if the resist pattern is formed with a line width of 20 Ī¼m or less, peeling of the bonded portion between the resist pattern and the substrate and dent of the relief hardly occur, and a resist pattern perpendicular to the substrate can be formed stably.
ćļ¼ļ¼ļ¼ļ¼ć[0028]
ćå®ę½ä¾ć仄äøćå®ę½ä¾ćē¤ŗćć¦ę¬ēŗęćč©³ććčŖ¬ęć
ćć ļ¼»åęä¾ļ¼ļ¼½ę¹ęę©ćęø©åŗ¦čØćć³ć³ćć³ćµāćåććé
åč£
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ęéååæćććććć®å¾ćļ¼ļ¼āć«ęęø©ćććć®ęø©åŗ¦ć
ļ¼ęéē¶ęććååæćēµäŗćććććć®å¾ćļ¼ļ¼Ī¼ļ½ē®
éć®ęæ¾åøć«ć¦ęæ¾éę“ęµććļ¼ļ¼āå¾Ŗē°ē±é¢Øä¹¾ē„ę©ć§ä¹¾ē„
ććććć«ē³»éåä½ćå¾ććå¾ćććéåä½ćÆééå¹³å
ååéļ¼ļ½ļ¼ļ¼ļ¼ļ¼ļ¼ļ¼ļ¼ćååéååøļ¼ļ½ļ¼ļ¼ļ½ļ¼
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øä¾”ļ¼ļ¼ļ¼ļ½ļ½ļ¼«ļ¼Æļ¼Øļ¼ļ½ć§ćć£ćććć
ć§ćééå¹³åååéļ¼ļ½ććć³ę°å¹³åååéļ¼ļ½ćÆćę±
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ć³ęē®ć§ę±ćććęŗ¶å¤ć«ćÆćļ¼“ļ¼Øļ¼¦ćä½æēØćććThe present invention will be described below in detail with reference to examples. [Synthesis Example 1] A polymerization apparatus equipped with a stirrer, a thermometer, and a condenser was charged with 250 parts by weight of deionized water, and polyvinyl alcohol (degree of saponification 80%, degree of polymerization 1700) was added under stirring. 6 parts by weight were added. After completely dissolving the polyvinyl alcohol, methacrylic acid (hereinafter abbreviated as MAA): 20 parts by weight, benzyl methacrylate (hereinafter Bz)
MA): 10 parts by weight, butyl acrylate (hereinafter B)
A: 10 parts by weight, methyl methacrylate (hereinafter M
MA) 60 parts by weight, n-dodecyl mercaptan:
0.5 parts by weight and 0.4 parts by weight of azoisobutyronitrile were added, the temperature was raised to 75 Ā° C., and the reaction temperature was maintained at 75 Ā° C.
Allowed to react for hours. Thereafter, the temperature was raised to 90 Ā° C., and this temperature was maintained for 1 hour to terminate the reaction. Thereafter, the mixture was filtered and washed with a filter cloth having an opening of 10 Ī¼m, and dried with a circulating hot air dryer at 50 Ā° C. to obtain a vinyl polymer. The obtained polymer had a weight average molecular weight Mw = 51,040 and a molecular weight distribution Mw / Mn =
It was 1.84, and the acid value was 132 mgKOH / g. Here, the weight average molecular weight Mw and the number average molecular weight Mn were determined in terms of styrene by gel permeation chromatography (GPC) using HLC-8120GPC manufactured by Tosoh Corporation. THF was used as the solvent.
ćļ¼ļ¼ļ¼ļ¼ćļ¼»åęä¾ļ¼ćļ¼ļ¼½åęä¾ļ¼ć®č£½é ęä½ćØå
ę§ć«ćć¦ćč”Øļ¼ć«ē¤ŗććććć«ē³»åéä½ēµęć§ćććć
éåćććå¾ćććććć«ē³»éåä½ć®ē¹ę§å¤ćč”Øļ¼ć«ē¤ŗ
ćććč”Øļ¼äøć®ļ¼³ļ¼ļ¼”ćÆć¹ćć¢ćŖć«ć”ćæćÆćŖć¬ć¼ććč”Ø
ćć[Synthesis Examples 2 to 5] Polymerization was carried out in the same manner as in Production Example 1 with the vinyl monomer compositions shown in Table 1. Table 2 shows the characteristic values of the obtained vinyl polymer. SMA in Table 1 represents stearyl methacrylate.
ćļ¼ļ¼ļ¼ļ¼ćļ¼»ęÆč¼åęä¾ļ¼ćļ¼ļ¼½åęä¾ļ¼ć®č£½é ęä½
ćØåę§ć«ćć¦ćč”Øļ¼ć«ē¤ŗććććć«ē³»åéä½ēµęć§ćć
ććéåćććå¾ćććććć«ē³»éåä½ć®ē¹ę§å¤ćč”Øļ¼
ć«ē¤ŗćććč”Øļ¼äøć®ļ¼¢ļ¼ļ¼”ćÆććć«ć”ćæćÆćŖć¬ć¼ććļ¼
āļ¼„ļ¼Øļ¼ļ¼”ćÆļ¼āćØćć«ććć·ć«ć”ćæćÆćŖć¬ć¼ććč”Ø
ćć[Comparative Synthesis Examples 1 and 2] Polymerization was carried out in the same manner as in Production Example 1 with the vinyl monomer compositions shown in Table 1. Table 2 shows the characteristic values of the obtained vinyl polymer.
It was shown to. BMA in Table 1 is butyl methacrylate, 2
-EHMA represents 2-ethylhexyl methacrylate.
ćļ¼ļ¼ļ¼ļ¼ćļ¼»ęÆč¼åęä¾ļ¼ļ¼½ę¹ęę©ćęø©åŗ¦čØćć³ć³ć
ć³ćµāćåććéåč£
ē½®ć«ćļ¼ļ¼„ļ¼«ļ¼ļ¼ļ¼ļ¼éééØćå
ććę¹ęćč”ććļ¼ļ¼”ļ¼”ļ¼ļ¼ļ¼éééØćļ¼¢ļ½ļ¼ļ¼”ļ¼ļ¼ļ¼
éééØćļ¼¢ļ¼”ļ¼ļ¼ļ¼éééØćļ¼ļ¼ļ¼”ļ¼ļ¼éééØćļ½āć
ćć·ć«ć”ć«ć«ććæć³ļ¼ļ¼ļ¼ļ¼éééØćć¢ć¾ć¤ć½ćććć
ććŖć«ļ¼ļ¼ļ¼ļ¼éééØćå ććļ¼ļ¼āć«ęęø©ććååæęø©
åŗ¦ļ¼ļ¼āćē¶ęćć¦ļ¼ęéååæćććććć®å¾ćļ¼ļ¼ā
ć«ęęø©ćććć®ęø©åŗ¦ćļ¼ęéē¶ęććååæćēµäŗćć
ććå¾ćććéåä½ć®ē¹ę§å¤ćč”Øļ¼ć«ē¤ŗććć[Comparative Synthesis Example 3] MEK: 185 parts by weight was added to a polymerization apparatus equipped with a stirrer, a thermometer, and a condenser, followed by stirring. MAA: 20 parts by weight, BzMA: 10
Parts by weight, BA: 10 parts by weight, MMA 60 parts by weight, n-dodecyl mercaptan: 0.1 parts by weight, azoisobutyronitrile: 0.5 parts by weight, the temperature was raised to 60 Ā° C, and the reaction temperature was raised to 60 Ā° C. The reaction was maintained for 4 hours. Then 65 Ā° C
, And the temperature was maintained for 1 hour to terminate the reaction. Table 2 shows the characteristic values of the obtained polymer.
ćļ¼ļ¼ļ¼ļ¼ć[0032]
ćč”Øļ¼ć [Table 1]
ćļ¼ļ¼ļ¼ļ¼ć[0033]
ćč”Øļ¼ć [Table 2]
ćļ¼ļ¼ļ¼ļ¼ćļ¼»å®ę½ä¾ļ¼ļ¼½åęä¾ļ¼ć®éåä½č©¦ęćäøčØ
ć®ę¹ę³ć§ęå
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ļ¼ććć³å³ļ¼ć«ē¤ŗććExample 1 The polymer sample of Synthesis Example 1 was used as a photosensitive resin composition by the following method to prepare a photosensitive film, and a resist pattern was formed using the photosensitive film. The performance of the photosensitive film was evaluated by the following method. The results are shown in Table 3 and FIG.
ćļ¼ļ¼ļ¼ļ¼ćļ¼»å®ę½ä¾ļ¼ćļ¼ļ¼½åęä¾ļ¼ćļ¼ć®éåä½č©¦
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ć®ēµęćč”Øļ¼ććć³å³ļ¼ćļ¼ć«ē¤ŗćć[Examples 2 to 5] Performance evaluation was performed in the same manner as in Example 1 using the polymer samples of Synthesis Examples 2 to 5. The results are shown in Table 3 and FIGS.
ćļ¼ļ¼ļ¼ļ¼ćļ¼»ęÆč¼ä¾ļ¼ćļ¼ļ¼½ęÆč¼åęä¾ļ¼ćļ¼ć®éå
ä½č©¦ęćēØćć¦å®ę½ä¾ļ¼ćØåę§ć«ćć¦ę§č½č©ä¾”ćč”ć£
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ćŖć¬ćøć¹ćććæć¼ć³ćå½¢ęć§ććŖćć£ćć[Comparative Examples 1 to 3] Performance evaluation was performed in the same manner as in Example 1 using the polymer samples of Comparative Synthesis Examples 1 to 3. The results are shown in Table 3 and FIGS. The adhesion of the resist pattern to the substrate was poor, and a resist pattern perpendicular to the substrate could not be formed.
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éå§å¤ćØćć¦
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ćć³ć¾ćć§ćć³ļ¼ļ¼ļ¼ļ½ćęŗ¶å¤ćØćć¦ć¤ć½ćććć«ć¢ć«
ć³ć¼ć«ļ¼ļ¼ļ½ćę¶ę©å¤ćØćć¦ććŖć”ććć¼ć«ćććć³ć
ćŖć¢ćÆćŖć¬ć¼ćļ¼ļ¼ļ½ććć¹ćć§ćć¼ć«ļ¼”ććŖćŖćć·ćØ
ćć¬ć³ćøć”ćæćÆćŖć¬ć¼ćļ¼ļ¼ļ½ćé
åćć¦ęå
ę§ęعčēµ
ęē©ć®ęŗ¶ę¶²ćčŖæč£½ććć[Preparation of Photosensitive Resin Composition] The polymer samples obtained in the synthesis examples and comparative synthesis examples were adjusted to a 50% by weight solution with MEK, and 150 g of this polymer solution and 0.5 g of tribromophenylsulfone were prepared. , Leuco Crystal Violet 1
g, malachite green 0.05 g, P, Pā²-diethylamino-benzophenone 0.1 g as a photoinitiator,
A solution of the photosensitive resin composition was prepared by blending 5.0 g of benzophenone, 10 g of isopropyl alcohol as a solvent, 20 g of trimethylolpropane triacrylate as a crosslinking agent, and 10 g of bisphenol A polyoxyethylene dimethacrylate.
ćļ¼ļ¼ļ¼ļ¼ććęå
ćć£ć«ć ć®ä½č£½ććć®ęå
ę§ęعčēµ
ęē©ć®ęŗ¶ę¶²ćļ¼ļ¼Ī¼ļ½åć®ććŖćØćć¬ć³ćć¬ććæć¬ć¼ć
ćć¤ć«ć äøć«å”å·„ćć室ęø©ć§ļ¼åę¾ē½®ććå¾ćļ¼ļ¼ļ¼ā
ć®ćŖć¼ćć³ć§ļ¼ļ¼åä¹¾ē„ćć¦ćęå
層åļ¼ļ¼Ī¼ļ½ć®ęå
ćć£ć«ć ćä½č£½ććć[Preparation of Photosensitive Film] A solution of this photosensitive resin composition was applied on a polyethylene terephthalate film having a thickness of 20 Ī¼m and left at room temperature for 2 minutes.
After drying in an oven for 10 minutes, a photosensitive film having a photosensitive layer thickness of 30 Ī¼m was prepared.
ćļ¼ļ¼ļ¼ļ¼ććåÆēę§ć®č©ä¾”ćē ē£Øć»ę“ęµććļ¼ļ¼āć«
å ē±ććé
å¼µåŗęæäøć«ęå
ćć£ć«ć ćļ¼ļ¼ļ¼āć«å ē±ć
ćŖćććć¼ć«å§ļ¼ļ½ļ½ļ¼ļ½ļ½2 ć§ć©ććć¼ćććććć®
ć©ććć¼ćåŗęæć«ļ¼Ŗļ¼©ļ¼³ ļ¼¤ļ¼ļ¼ļ¼ļ¼ć®č©¦éØę¹ę³ć«å¾ć£
ć¦ćē¢ē¤ē®ē¶ć«ćÆćć¹ć«ćććå
„ćć¦ļ¼ļ¼ļ¼åć¾ćē®ć
ä½ć£ććꬔćć§ććć¼ćŖć³ć°č©¦éØćč”ććć¾ćē®ć®å„é¢
ē¶ę
ćļ¼Ŗļ¼©ļ¼³ļ¼¤ļ¼ļ¼ļ¼ļ¼ć«ęŗćć¦ćå„é¢ććŖćć¾ćē®ć®
ę°ć«ćć£ć¦č©ä¾”ććć āć»ć»ć»ć»å„é¢ććŖćć¾ćē®ļ¼ļ¼ļ¼å ā³ć»ć»ć»ć»å„é¢ććŖćć¾ćē®ļ¼ļ¼ćļ¼ļ¼å Ćć»ć»ć»ć»å„é¢ććŖćć¾ćē®ļ¼ļ¼å仄äø[Evaluation of Adhesion] A photosensitive film was laminated on a copper-clad substrate heated at 60 Ā° C. while heating at 120 Ā° C. under a roll pressure of 3 kg / cm 2 . In accordance with the test method of JIS D0202, 100 cross-cuts were formed in a cross-cut pattern on the laminated substrate. Next, a peeling test was performed, and the stripped state of the squares was evaluated according to JIS D0202 by the number of squares that did not peel. ā ć» ć» ć» ć» 100 non-peeled squares ā³ ć» ć» ć» ć» 91-99 non-peeled squares Ć ć» ć» ć» ć» 90 or less non-peeled squares
ćļ¼ļ¼ļ¼ļ¼ććć¬ćøć¹ćććæć¼ć³ęå½¢č©ä¾”ćꬔćć§ćč©
ä¾”ēØćć¬ćć£ć«ć ļ¼ć©ć¤ć³å¹
ćØć¹ćć¼ć¹å¹
ļ¼ļ¼Ī¼ļ½ć®ć
ćæć¼ć³ćć¹ćÆļ¼ćä½æēØććļ¼ļ½ļ¼·é«å§ę°“éēÆć§ļ¼ļ¼ļ½ļ¼Ŗ
ļ¼ļ½ļ½2 ć®é²å
ćč”ć£ćå¾ćććŖćØćć¬ć³ćć¬ććæć¬ć¼
ććć£ć«ć ćå„é¢ććļ¼ļ¼āć®ļ¼ééļ¼
ēé
øćććŖć¦ć
ę°“ęŗ¶ę¶²ćļ¼ļ¼ē§éć¹ćć¬ć¼ććććØć«ććęŖé²å
éØåć
é¤å»ćććęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćļ¼³ļ¼„ļ¼åēć§č¦³åÆćć¦č©ä¾”ć
ćć"Evaluation of resist pattern formation" Then, using a negative film for evaluation (a pattern mask having a line width and a space width of 20 Ī¼m), 70 mJ using a 3 kW high-pressure mercury lamp.
After exposure to light / cm 2 , the polyethylene terephthalate film was peeled off, and an unexposed portion was removed by spraying a 1% by weight aqueous solution of sodium carbonate at 30 Ā° C. for 60 seconds. The photocurable resist pattern formed by the photosensitive resin composition on the copper-clad substrate was observed and evaluated by SEM photograph.
ćļ¼ļ¼ļ¼ļ¼ć[0041]
ćč”Øļ¼ć [Table 3]
ćļ¼ļ¼ļ¼ļ¼ć[0042]
ćēŗęć®å¹ęć仄äøčŖ¬ęććććć«ćę¬ēŗęć®ęå
ę§ć
ć£ć«ć ēØęå
ę§ęعčēµęē©ćÆćć¢ćÆćŖć«ē³»é«é
øä¾”ęعčć
å«ęććęå
ę§ćć£ć«ć ēØęå
ę§ęعčēµęē©ć§ćć£ć¦ć
åčØć¢ćÆćŖć«ē³»é«é
øä¾”ęعčććļ¼ć”ćæļ¼ć¢ćÆćŖć«é
øćØć
ćć³ćøć«ļ¼ć”ćæļ¼ć¢ćÆćŖć¬ć¼ćć¾ććÆēē“ ę°ļ¼ļ¼ćļ¼ļ¼
ć®ć¢ć«ćć«åŗćęććć¢ć«ćć«ļ¼ć”ćæļ¼ć¢ćÆćŖć¬ć¼ćļ¼
ćļ¼ļ¼ééļ¼
ćØćę§ęåéä½ćØćć¦å«ćå
±éåä½ć§ć
ććåčØć¢ćÆćŖć«ē³»é«é
øä¾”ęعčć®ééå¹³åååéćć
ļ¼ļ¼ļ¼ļ¼ļ¼ćļ¼ļ¼ļ¼ļ¼ļ¼ļ¼ļ¼ć§ćććåčØć¢ćÆćŖć«ē³»é«
é
øä¾”ęعčć®ååéååøļ¼ļ¼ļ½ļ¼ļ¼ļ½ļ¼ććļ¼ļ¼ļ¼ä»„äøć§
ććć®ć§ćč§£ååŗ¦ćåŗęæćøć®åÆēę§ć«åŖććē¾åå¾ć«å½¢
ęćććć¬ćøć¹ćććæć¼ć³ćļ¼ļ¼Ī¼ļ½ä»„äøć®ē·å¹
ć§å®å®
ćć¦å½¢ęććććØćć§ćććć¾ććę¬ēŗęć®ęå
ę§ćć£
ć«ć ćÆćåčØęå
ę§ćć£ć«ć ēØęå
ę§ęعčēµęē©ćććŖ
ćęå
層ćęćć¦ććć®ć§ćč§£ååŗ¦ćåŗęæćøć®åÆēę§ć«
åŖććē¾åå¾ć«å½¢ęćććć¬ćøć¹ćććæć¼ć³ćļ¼ļ¼Ī¼ļ½
仄äøć®ē·å¹
ć§å®å®ćć¦å½¢ęććććØćć§ććé
ē·ććæć¼
ć³ć®é«åÆåŗ¦åćććŖć³ćé
ē·ęæć®å°ååćåÆč½ćØćŖććAs described above, the photosensitive resin composition for a photosensitive film of the present invention is a photosensitive resin composition for a photosensitive film containing an acrylic high acid value resin,
The acrylic high acid value resin, (meth) acrylic acid,
Benzyl (meth) acrylate or C12-18
(Meth) acrylate 2 having an alkyl group
-50% by weight as a constituent monomer, and the weight average molecular weight of the acrylic high acid value resin is:
Since the molecular weight distribution (Mw / Mn) of the acrylic high acid value resin is 2.5 or less, it is excellent in resolution and adhesion to a substrate, and is formed after development. A resist pattern can be formed stably with a line width of 20 Ī¼m or less. Further, since the photosensitive film of the present invention has a photosensitive layer composed of the photosensitive resin composition for a photosensitive film, it has excellent resolution and adhesion to a substrate, and has a resist pattern formed after development of 20 Ī¼m.
It can be formed stably with the following line width, and the density of the wiring pattern can be increased, and the size of the printed wiring board can be reduced.
ćå³ļ¼ć å®ę½ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 1 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Example 1.
ćå³ļ¼ć å®ę½ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 2 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Example 2.
ćå³ļ¼ć å®ę½ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 3 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Example 3.
ćå³ļ¼ć å®ę½ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 4 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Example 4.
ćå³ļ¼ć å®ę½ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 5 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Example 5.
ćå³ļ¼ć ęÆč¼ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 6 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Comparative Example 1.
ćå³ļ¼ć ęÆč¼ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 7 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Comparative Example 2.
ćå³ļ¼ć ęÆč¼ä¾ļ¼ć®ęå
ę§ęعčēµęē©ćé
å¼µåŗęæäøć«
å½¢ęććå
ē”¬åć¬ćøć¹ćććæć¼ć³ćē¤ŗćļ¼³ļ¼„ļ¼åēć§ć
ććFIG. 8 is an SEM photograph showing a photocurable resist pattern formed on a copper-clad substrate using the photosensitive resin composition of Comparative Example 3.
āāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāā ććć³ććć¼ćøć®ē¶ć ļ¼¦ćæć¼ć (åčļ¼ 2H025 AA02 AA03 AA14 AB11 AB15 AC01 AD01 BC43 BC66 BC74 CA01 CB13 CB14 CB43 CB54 CB55 CB56 FA03 FA17 4J100 AB02R AG04R AJ02P AL03R AL04R AL05Q AL08Q AL09R AM02R BC43Q CA04 CA05 DA01 DA04 JA37 5E339 BE13 CC01 CC02 CC10 CD01 CE12 CE16 CF16 CF17 DD02Ā āāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāāē¶ ć Continued on front page F-term (reference) 2H025 AA02 AA03 AA14 AB11 AB15 AC01 AD01 BC43 BC66 BC74 CA01 CB13 CB14 CB43 CB54 CB55 CB56 FA03 FA17 4J100 AB02R AG04R AJ02P AL03R AL04R AL05Q AL08Q AL09R AM04 CA04 DA04 CC01 CC02 CC10 CD01 CE12 CE16 CF16 CF17 DD02
Claims (2)
ćć£ć«ć ēØęå ę§ęعčēµęē©ć§ćć£ć¦ć åčØć¢ćÆćŖć«ē³»é«é øä¾”ęعčććļ¼ć”ćæļ¼ć¢ćÆćŖć«é øćØć
ćć³ćøć«ļ¼ć”ćæļ¼ć¢ćÆćŖć¬ć¼ćć¾ććÆēē“ ę°ļ¼ļ¼ćļ¼ļ¼
ć®ć¢ć«ćć«åŗćęććć¢ć«ćć«ļ¼ć”ćæļ¼ć¢ćÆćŖć¬ć¼ćļ¼
ćļ¼ļ¼ééļ¼ ćØćę§ęåéä½ćØćć¦å«ćå ±éåä½ć§ć
ćć åčØć¢ćÆćŖć«ē³»é«é øä¾”ęعčć®ééå¹³åååéććļ¼ļ¼ļ¼
ļ¼ļ¼ćļ¼ļ¼ļ¼ļ¼ļ¼ļ¼ļ¼ć§ććć åčØć¢ćÆćŖć«ē³»é«é øä¾”ęعčć®ååéååøļ¼ļ¼ļ½ļ¼ļ¼ļ½ļ¼
ććļ¼ļ¼ļ¼ä»„äøć§ććććØćē¹å¾“ćØććęå ę§ćć£ć«ć
ēØęå ę§ęعčēµęē©ć1. A photosensitive resin composition for a photosensitive film containing an acrylic high acid value resin, wherein the acrylic high acid value resin comprises (meth) acrylic acid,
Benzyl (meth) acrylate or C12-18
(Meth) acrylate 2 having an alkyl group
And a weight average molecular weight of the acrylic high acid value resin of 8.0 to 50% by weight as a constituent monomer.
Molecular weight distribution (Mw / Mn) of the acrylic high acid value resin
Is 2.5 or less, the photosensitive resin composition for photosensitive films.
ęعčēµęē©ćććŖćęå 層ćęććććØćē¹å¾“ćØććę
å ę§ćć£ć«ć ć2. A photosensitive film comprising a photosensitive layer comprising the photosensitive resin composition for a photosensitive film according to claim 1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14247699A JP2000330272A (en) | 1999-05-21 | 1999-05-21 | Photosensitive resin composition for photosensitive film and photosensitive film |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14247699A JP2000330272A (en) | 1999-05-21 | 1999-05-21 | Photosensitive resin composition for photosensitive film and photosensitive film |
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| JP2000330272A true JP2000330272A (en) | 2000-11-30 |
Family
ID=15316218
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|---|---|---|---|
| JP14247699A Pending JP2000330272A (en) | 1999-05-21 | 1999-05-21 | Photosensitive resin composition for photosensitive film and photosensitive film |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007025152A (en) * | 2005-07-14 | 2007-02-01 | Goo Chemical Co Ltd | Alkali development type photosensitive resist ink composition for printed wiring board production, cured product thereof and printed wiring board |
| JP2007034286A (en) * | 2005-07-01 | 2007-02-08 | Eternal Chemical Co Ltd | Photoimageable composition |
| WO2012067107A1 (en) * | 2010-11-17 | 2012-05-24 | ę„ē«åęå·„ę„ę Ŗå¼ä¼ē¤¾ | Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for manufacturing printed wiring board |
| KR101188759B1 (en) * | 2009-03-18 | 2012-10-10 | ģ£¼ģķģ¬ ģģ§ķķ | Acryl-based copolymer, optical film and liquid crystal display comprising the same |
| WO2012165918A3 (en) * | 2011-06-01 | 2013-03-28 | ģ£¼ģķģ¬ ģģ§ķķ | Resin composition for optical film and optical film using the same |
| JP2014134815A (en) * | 2006-12-27 | 2014-07-24 | Hitachi Chemical Co Ltd | Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for manufacturing printed wiring board |
-
1999
- 1999-05-21 JP JP14247699A patent/JP2000330272A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007034286A (en) * | 2005-07-01 | 2007-02-08 | Eternal Chemical Co Ltd | Photoimageable composition |
| KR101370431B1 (en) * | 2005-07-01 | 2014-03-05 | ģ“ķ°ė ģ¼ėÆøģ¹¼ ģ»“ķ¼ė ė¦¬ėÆøķ°ė | Photoimageable composition |
| JP2007025152A (en) * | 2005-07-14 | 2007-02-01 | Goo Chemical Co Ltd | Alkali development type photosensitive resist ink composition for printed wiring board production, cured product thereof and printed wiring board |
| JP2014134815A (en) * | 2006-12-27 | 2014-07-24 | Hitachi Chemical Co Ltd | Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for manufacturing printed wiring board |
| KR101188759B1 (en) * | 2009-03-18 | 2012-10-10 | ģ£¼ģķģ¬ ģģ§ķķ | Acryl-based copolymer, optical film and liquid crystal display comprising the same |
| WO2012067107A1 (en) * | 2010-11-17 | 2012-05-24 | ę„ē«åęå·„ę„ę Ŗå¼ä¼ē¤¾ | Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for manufacturing printed wiring board |
| JPWO2012067107A1 (en) * | 2010-11-17 | 2014-05-12 | ę„ē«åęę Ŗå¼ä¼ē¤¾ | Photosensitive resin composition, photosensitive element, resist pattern forming method and printed wiring board manufacturing method |
| WO2012165918A3 (en) * | 2011-06-01 | 2013-03-28 | ģ£¼ģķģ¬ ģģ§ķķ | Resin composition for optical film and optical film using the same |
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