CN110941141A - Aqueous solution developing dry film photoresist - Google Patents
Aqueous solution developing dry film photoresist Download PDFInfo
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- CN110941141A CN110941141A CN201911384711.2A CN201911384711A CN110941141A CN 110941141 A CN110941141 A CN 110941141A CN 201911384711 A CN201911384711 A CN 201911384711A CN 110941141 A CN110941141 A CN 110941141A
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- Prior art keywords
- dry film
- film photoresist
- phthalate
- acrylate
- photoresist
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 71
- 239000007864 aqueous solution Substances 0.000 title abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 28
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 17
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 239000004014 plasticizer Substances 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000000853 adhesive Substances 0.000 claims abstract description 9
- 230000001070 adhesive effect Effects 0.000 claims abstract description 9
- 238000012719 thermal polymerization Methods 0.000 claims abstract description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 8
- 150000003254 radicals Chemical class 0.000 claims abstract description 8
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims abstract description 8
- 229940124543 ultraviolet light absorber Drugs 0.000 claims abstract description 7
- 238000000016 photochemical curing Methods 0.000 claims abstract description 6
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 claims abstract description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 12
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 6
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 6
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 claims description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 6
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims description 6
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 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 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 4
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 3
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 3
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 claims description 3
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 claims description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 3
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 claims description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 3
- VOWAEIGWURALJQ-UHFFFAOYSA-N Dicyclohexyl phthalate Chemical compound C=1C=CC=C(C(=O)OC2CCCCC2)C=1C(=O)OC1CCCCC1 VOWAEIGWURALJQ-UHFFFAOYSA-N 0.000 claims description 3
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 claims description 3
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 3
- 229960001826 dimethylphthalate Drugs 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
- 229940079877 pyrogallol Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 238000007789 sealing Methods 0.000 abstract description 9
- 239000010408 film Substances 0.000 description 72
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 21
- 229910052802 copper Inorganic materials 0.000 description 17
- 239000010949 copper Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002390 adhesive tape Substances 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 239000004643 cyanate ester Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002421 finishing Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention relates to the technical field of circuit board production and manufacturing, in particular to a dry film photoresist developed by aqueous solution, which comprises the following components: acrylate adhesive A, epoxy acrylate B1, urethane acrylate B2, a photo-curing monomer B3, a free radical initiator C, an active monomer D, N-phenylglycine, a plasticizer, an ultraviolet light absorber and a thermal polymerization inhibitor; the epoxy acrylate B1 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the epoxy acrylate B1 is 1-30 mol; the urethane acrylate B2 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the urethane acrylate B2 is 1-30 mol; the hole sealing capability of the aqueous solution developed dry film photoresist is obviously higher than that of the commercial dry film photoresist, so that the aqueous solution developed dry film photoresist has wide application prospect and high market value.
Description
Technical Field
The invention relates to the technical field of circuit board production and manufacturing, in particular to a dry film photoresist developed by aqueous solution.
Background
In general, the components of the dry film photoresist include a thermoplastic polymer formed from an acrylic or methacrylic monomer, a photopolymerizable monomer, a thermal polymerization inhibitor, a radical photoinitiator, and an ultraviolet absorber. They are usually sold as dry film rolls, the components being sandwiched between a flexible support film PET and a cover film PE. Wherein the thermoplastic polymer is generally a non-reactive type of material.
In the prior art, free radical polymerization generally has obvious shrinkage characteristics, and shrinkage generated during polymerization can generate negative effects on the adhesive force of a dry film photoresist on a copper surface and can also generate side effects on the hole sealing capability during the manufacture of the currently popular outer-layer circuit board. Generally, some photopolymerization monomer with a single optical group is added appropriately to reduce shrinkage.
In addition, as intelligent devices are diversified, the styles of circuit boards also show various development trends. In the actual production of printed wiring boards, it has been found that the aperture and shape of the wiring board vary greatly. Therefore, the existing dry film photoresist sold on the market generally shows a phenomenon of poor sealing when facing odd-shaped pore diameters, thereby affecting the production quality of circuit boards.
Disclosure of Invention
In order to further improve the hole sealing capability of the dry film photoresist, the invention uses epoxy resin for modification, and introduces (methyl) acrylic acid containing double bonds on chain type epoxy resin or introduces (methyl) acrylic acid containing double bonds on a polyurethane resin side chain, so that the epoxy resin has reaction activity and participates in photocuring reaction, thereby obviously improving the hole sealing capability of the dry film photoresist.
In order to achieve the purpose, the technical scheme adopted by the invention comprises the following steps:
in a first aspect, the invention provides an aqueous developable dry film photoresist comprising the following components:
acrylate adhesive A, epoxy acrylate B1, urethane acrylate B2, a photo-curing monomer B3, a free radical initiator C, an active monomer D, N-phenylglycine, a plasticizer, an ultraviolet light absorber and a thermal polymerization inhibitor;
the epoxy acrylate B1 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the epoxy acrylate B1 is 1-30 mol;
the dry film photoresist comprises a dry film photoresist and urethane acrylate B2, wherein the urethane acrylate B2 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the urethane acrylate B2 is 1-30 mol;
wherein the structural formula of the active monomer D is as follows:
wherein X represents-CH2CH2O-, Y represents-CH2-CH(CH3) O-or/and-CH (CH)3)CH2O-; m is an integer of 1 to 25, and n is an integer of 1 to 25.
It can be seen that reactive monomer D is an ethoxylated bisphenol A dimethacrylate monomer containing a large number of ethoxy EO and propoxy PO block structures. Also, the ethoxylated bisphenol a dimethacrylate monomer may be SR348, CD540, SR541, CD542, SR480, and the like available from sartomer company, usa.
It should be added that the reaction equation for preparing the epoxy acrylate B1 is as follows:
also, the preparation step of the epoxy acrylate B1 may include, for example: adding a certain amount of epoxy resin, epoxy diluent and polymerization inhibitor into a four-neck flask provided with a stirrer, a condenser pipe, a constant-pressure funnel and a thermometer, stirring and heating to 75 ℃, slowly adding a proper amount of acrylic acid and initiator, and finishing dropping within 0.5-1 hour; and then heating to 80-90 ℃ for continuous reaction, sampling at regular time to detect the acid value, cooling when the acid value is lower than 5mg KOH/g, and carrying out post-treatment to obtain the epoxy acrylate B1.
It is worth noting that the reaction equation for preparing the urethane acrylate B2 is as follows:
also, the preparation step of the urethane acrylate B2 may include, for example: in a device equipped with a stirrer, N2Introducing dry N into a four-neck flask of an introducing system, a condenser pipe and a thermometer2Then adding isocyanate, dripping polyol containing a catalyst at a proper stirring speed, controlling the reaction temperature at 70-80 ℃, sampling and detecting the content of free isocyanate after 3 hours, starting to add hydroxy acrylic acid after the reaction end point is reached, continuing to react for 3 hours at 70-90 ℃, and reacting for 3 hours when the isocyanate in the system is differentWhen the content of the cyanate ester is less than 0.1%, heating to 90 ℃, keeping the temperature for 0.5 hour, consuming the residual isocyanate, then stopping heating, cooling to 60 ℃, and discharging to obtain the cyanate ester.
Preferably, in the above dry film photoresist, the acrylate adhesive a is polymerized from 60 wt% of methacrylate, 18 wt% of methacrylic acid and 22 wt% of n-butyl acrylate in a butanone solvent.
Preferably, in the above dry film photoresist, the photocurable monomer B3 comprises any one or more of the following polyfunctional monomers: trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, triethylene glycol diacrylate, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate.
Further, the optional addition of a monofunctional (one vinyl-based double bond) photopolymerizable monomer having a carboxyl group to the composition enables the cured film to be peeled off from the copper plate into small pieces of film, and if the monofunctional polymerizable monomer is not added, the cured film is peeled off from the copper plate into large pieces of film, which are preferable in the form of small pieces because the cured film between fine wires can be more easily peeled off, and further, some peeling devices have a filtering system and large pieces of film may block the filtering system.
Preferably, in the above dry film photoresist, the radical initiator C is a bisimidazole initiator BCIM.
Preferably, in the above dry film photoresist, the plasticizer is selected from any one of: tributyl citrate, tributyl acetylcitrate, di (2-ethylhexyl) phthalate, dioctyl phthalate, butyl benzyl phthalate, di-sec-octyl phthalate, dicyclohexyl phthalate, dibutyl phthalate, diisobutyl phthalate, dimethyl phthalate, diethyl phthalate, diisononyl phthalate, diisodecyl phthalate.
Preferably, in the dry film photoresist, the plasticizer accounts for 0.9-1.1% of the total mass of the dry film photoresist.
Preferably, in the dry film photoresist, the ultraviolet light absorber accounts for 0.05-2.5% of the total mass of the dry film photoresist.
Preferably, the dry film photoresist further comprises an additive.
Further preferably, the additive is selected from any one or more of: leuco dye, ground dye, adhesion promoter and antioxidant. These are mentioned herein, but are not necessarily essential to the invention.
Preferably, in the above dry film photoresist, the thermal polymerization inhibitor is selected from any one of p-methoxyphenol, t-butylcatechol, pyrogallol, β -naphthol, 2, 6-di-t-butyl-p-cresol, 2, 2' -methylene-bis (4-ethyl-6-t-butylphenol).
In addition, the various photopolymerizable components of the invention described above are prepared by mixing together and stirring a series of different compounds with a solvent, which is generally selected from: alcohols, ketones, halogenated hydrocarbons, ethers. After mixing uniformly, coating the above photopolymerization components on a flexible carrier film, evaporating the solvent, and covering a protective film, wherein the thickness of the photoresist is preferably 10-80 μm, and the thickness of the carrier film is preferably 0.0254-0.0508 mm. The dry film of the present invention may be placed on a flexible or non-flexible support or may be formed into a laminate or roll.
In the present invention, the photopolymerizable component is used as a photoresist in the production of printed wiring boards, generally, the component is applied to the surface of the copper layer of a copper foil substrate, exposed through a negative film to form a latent image under ultraviolet irradiation, and then developed in a known aqueous developer to remove unpolymerized component from the copper surface to form a bare copper surface, and the copper thin layer is subjected to a known means for processing such as plating or etching, and the polymerized material now serves to protect the copper layer it covers, and finally the polymerized material is stripped off with a stripping solution.
The photopolymerizable composition of the invention is thermally pressed onto the copper foil substrate by a known method such as a hot plate or a hot barrel laminator together with the carrier film after the cover film is removed, and the carrier film is removed at the time of development after exposure polymerization. Generally, the amount of light used for polymerization of the component is about 20 to 120mj/cm2The exact amount of light will depend on such factors as the particular composition and type of negative film being exposed.
The copper foil base is, among other things, any known copper/insulation laminate used in the production of circuit boards, such as a glass fiber reinforced ethylene oxide resin copper foil laminate.
The aqueous developer used in the present invention is an alkaline agent at a concentration of 0.5 to 10% by weight, preferably 0.5 to 1% by weight. The latent image is in the solution for a time sufficient to wash away unpolymerized components. The alkaline agents used are alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and alkali metal salts formed by reaction with weak acids such as sodium carbonate, sodium bicarbonate and alkali metal phosphates and pyrophosphates, of which sodium carbonate is preferred. The wiring board may be immersed in the developer, or the developer may be sprayed onto the wiring substrate.
Generally, stripping solutions adapted according to the invention for stripping off polymerized component substances are heated aqueous alkaline solutions, for example those having a higher concentration of the same aqueous alkaline solution as the developer, generally in a concentration of 1 to 10%, preferably 2 to 4%; the temperature of the stripping solution is generally about 45-68 deg.C, with a preferred temperature range of 50-55 deg.C. In addition, washing the substrate with the stripping liquid to strip off the polymerized substance is a known method, such as spraying the substrate with a heated stripping liquid, or preferably agitating the substrate in a heated stripping liquid solution. Techniques and equipment for exposure, including light sources, light intensity and exposure time, developing and stripping solutions and techniques and laminate components are all referred to herein.
In summary, compared with the prior art, the technical scheme provided by the invention at least has the following beneficial effects:
according to the dry film photoresist, the (methyl) acrylic acid is introduced into the epoxy acrylate and the polyurethane acrylate to participate in the photocuring reaction, so that the strength of a cured film can be obviously improved, and the hole covering performance is improved; in addition, the modified epoxy resin and polyurethane resin contain reactive double bonds, so that the use of small-molecule light-cured monomers can be reduced, the formula can be simplified, and the production control is facilitated. Therefore, the hole sealing capability of the aqueous solution developed dry film photoresist is obviously higher than that of the commercial dry film photoresist.
In conclusion, the aqueous solution developed dry film photoresist provided by the invention has wide application prospect and high market value.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The aqueous solution developed dry film photoresist comprises the following components:
acrylate adhesive A, epoxy acrylate B1, urethane acrylate B2, a photo-curing monomer B3, a free radical initiator C, an active monomer D, N-phenylglycine, a plasticizer, an ultraviolet light absorber and a thermal polymerization inhibitor;
the epoxy acrylate B1 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the epoxy acrylate B1 is 1-30 mol;
the dry film photoresist comprises a dry film photoresist and urethane acrylate B2, wherein the urethane acrylate B2 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the urethane acrylate B2 is 1-30 mol;
wherein the structural formula of the active monomer D is as follows:
wherein X represents-CH2CH2O-, Y represents-CH2-CH(CH3) O-or/and-CH (CH)3)CH2O-; m is an integer of 1 to 25, and n is an integer of 1 to 25.
In a preferred embodiment, the acrylate adhesive a is polymerized from 60 wt% of methacrylate, 18 wt% of methacrylic acid and 22 wt% of n-butyl acrylate in butanone solvent.
In a preferred embodiment, the photocurable monomer B3 comprises any one or more of the following multifunctional monomers: trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, triethylene glycol diacrylate, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate.
In a preferred embodiment, the free radical initiator C is a bisimidazole initiator BCIM.
In a preferred embodiment, the plasticizer is selected from any one of the following: tributyl citrate, tributyl acetylcitrate, di (2-ethylhexyl) phthalate, dioctyl phthalate, butyl benzyl phthalate, di-sec-octyl phthalate, dicyclohexyl phthalate, dibutyl phthalate, diisobutyl phthalate, dimethyl phthalate, diethyl phthalate, diisononyl phthalate, diisodecyl phthalate.
In a preferred embodiment, the plasticizer accounts for 0.9-1.1% of the total mass of the dry film photoresist.
In a preferred embodiment, the ultraviolet light absorber accounts for 0.05-2.5% of the total mass of the dry film photoresist.
In a preferred embodiment, the dry film photoresist further comprises an additive.
In a further preferred embodiment, the additive is selected from any one or more of the following: leuco dye, ground dye, adhesion promoter and antioxidant.
In a preferred embodiment, the thermal polymerization inhibitor is selected from any one of p-methoxyphenol, tert-butylcatechol, pyrogallol, β -naphthol, 2, 6-di-tert-butyl-p-cresol, 2, 2' -methylene-bis (4-ethyl-6-tert-butylphenol).
In the following examples, the test methods included:
dry film viscosity test
Zero shear viscosity (η 0) is measured using a stress rheometer (RSR) at 60 deg.C.the shear load measured is constant at 5000 g. the creep of the sample is recorded as 1000s, after exceeding the record, the shear force is removed and creep returns to measurement.zero shear viscosity (η 0) refers to the time from reaching steady state divided by its compliance (J). The example, J ═ 9.0X 10-4 (cm)2Dyne) at 1000s, at which time η 0 is 1.1 × 106 poises, samples were made from 80mil (2mm) thick disks made by stacking together dry, unexposed films that were pulled apart.
Flexibility test
The flexibility of the film after curing of the dry film photoresist is mainly tested, and the test method and the standard refer to the following national standards: GB/T1731-93, GB/T6742-86 and GB/T11185-89; GB/T1731-93 is selected for the test of the experiment.
Adhesion test
The dry film was adhered to the copper plate as measured by the following pass/fail test. Cleaning the copper plate by a proper mode, and laminating the film on the surface of the copper plate; after 15min, tearing off the film covered on the film, and pasting the adhesive tape on the surface of the film to ensure that the adhesive tape has better adhesiveness with the film; the adhesive tape is pulled hard to be quickly stripped from the film, and if the film and the adhesive tape are stripped from the copper surface together, the test fails; the test is passed if the film is still adhered to the copper side. This evaluation uses a 3M type scotch tape. The same test can be used for adhesion testing of the cured parts.
Examples
The dry film photoresist was prepared according to the following formulation of table 1, wherein examples 1 to 5 are the dry film photoresist according to the present invention, and the comparative example is a conventional dry film photoresist, specifically as follows:
TABLE 1 compositions of various dry film photoresists
In the above table 1, the acrylate adhesive a is polymerized from 60 wt% of methacrylate, 18 wt% of methacrylic acid and 22 wt% of n-butyl acrylate in butanone solvent; in the structure of B1 (modified by methacrylic acid), the double bond content is 5 mol; in the structure of B2 (modified by methacrylic acid), the double bond content is 5 mol; as the photocurable monomer B3, trimethylolpropane triacrylate (TMPTA); used as reactive monomer D was SR480 available from Saedoma, USA; p-methoxyphenol as a thermal polymerization inhibitor; the plasticizer is tributyl citrate (TBC).
In addition, the inventors respectively tested the above various dry film photoresists to compare the key indexes, and the specific experimental data is shown in the following table 2:
TABLE 2 comparison of resolution, adhesion, sealing performance and elasticity
Wherein, the test of the adhesion before developing mainly comprises: firstly tearing off the polyester film on the copper plate with the film, then attaching the polyester film on the surface of the photoresist by using a 3M transparent adhesive tape, forcibly pulling the adhesive tape to quickly remove the photoresist from the photoresist, and if the photoresist is separated from the copper surface along with the adhesive tape, failing the test (fail); if the photoresist is still adhered to the copper surface, the test passes. Data represent line widths that did not fall off after adhesion testing.
Further, the evaluation of the sealing performance mainly includes: drilling 100 holes with the diameter of 7.5mm in a copper-clad plate with the diameter of 50cm multiplied by 50 cm; making a corresponding film, and exposing the hole sealing test plate by using the energy of a 7-step (21-step) exposure ruler; and (5) checking the broken hole condition after the development. In the above table 2, □ indicates that there are more pores with 7.5mm pore diameter after development, and the proportion is more than 10%; ● represents that there are individual holes with 7.5mm aperture after development, and the number of broken holes is not more than 3; ● ● represents no broken pores in the pores with the diameter of 7.5mm after development, but the sealed membranes have wrinkles and smoothness; ● ● ● represents that the pores with a pore diameter of 7.5mm after development were not broken and the sealed membranes were smooth and abnormal.
In table 2 above, the elasticity evaluation included: the above-mentioned various dry film resists were cut into samples each having a length of 10cm and a width of 1.5cm, and the samples were exposed to energy of a 7-step (21-step) exposure scale. Elasticity was evaluated using a tensile tester at the same force, with different elasticity shown below:
△, representing the elasticity difference;
○, representing general elasticity;
○○, representing excellent elasticity;
○○○, indicates stronger elasticity and significant rebound.
The embodiments of the present invention have been described in detail, but the embodiments are merely examples, and the present invention is not limited to the embodiments described above. Any equivalent modifications and substitutions to those skilled in the art are also within the scope of the present invention. Accordingly, equivalent changes and modifications made without departing from the spirit and scope of the present invention should be covered by the present invention.
Claims (10)
1. An aqueous developable dry film photoresist comprising the following components:
acrylate adhesive A, epoxy acrylate B1, urethane acrylate B2, a photo-curing monomer B3, a free radical initiator C, an active monomer D, N-phenylglycine, a plasticizer, an ultraviolet light absorber and a thermal polymerization inhibitor;
the epoxy acrylate B1 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the epoxy acrylate B1 is 1-30 mol;
the dry film photoresist comprises a dry film photoresist and urethane acrylate B2, wherein the urethane acrylate B2 accounts for 1-15% of the total mass of the dry film photoresist, and the content of carbon-carbon double bonds in the urethane acrylate B2 is 1-30 mol;
wherein the structural formula of the active monomer D is as follows:
wherein X represents-CH2CH2O-, Y represents-CH2-CH(CH3) O-or/and-CH (CH)3)CH2O-; m is an integer of 1 to 25, and n is an integer of 1 to 25.
2. The dry film photoresist of claim 1, wherein the acrylate adhesive a is polymerized from 60 wt% of methacrylate, 18 wt% of methacrylic acid and 22 wt% of n-butyl acrylate in a butanone solvent.
3. The dry film photoresist of claim 1, wherein the photo-curable monomer B3 comprises any one or more of the following multifunctional monomers: trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, triethylene glycol diacrylate, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate.
4. The dry film photoresist of claim 1, wherein the radical initiator C is a bisimidazole initiator BCIM.
5. The dry film photoresist of claim 1, wherein the plasticizer is selected from any one of the following: tributyl citrate, tributyl acetylcitrate, di (2-ethylhexyl) phthalate, dioctyl phthalate, butyl benzyl phthalate, di-sec-octyl phthalate, dicyclohexyl phthalate, dibutyl phthalate, diisobutyl phthalate, dimethyl phthalate, diethyl phthalate, diisononyl phthalate, diisodecyl phthalate.
6. The dry film photoresist of claim 1, wherein the plasticizer is 0.9 to 1.1% by mass of the total mass of the dry film photoresist.
7. The dry film photoresist of claim 1, wherein the ultraviolet light absorber accounts for 0.05 to 2.5% of the total mass of the dry film photoresist.
8. The dry film photoresist of claim 1, wherein the dry film photoresist further comprises an additive.
9. The dry film photoresist of claim 8, wherein the additive is selected from any one or more of the following: leuco dye, ground dye, adhesion promoter and antioxidant.
10. The dry film photoresist of claim 1, wherein the thermal polymerization inhibitor is selected from the group consisting of p-methoxyphenol, t-butylcatechol, pyrogallol, β -naphthol, 2, 6-di-t-butyl-p-cresol, 2, 2' -methylene-bis (4-ethyl-6-t-butylphenol).
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