CN111123647A - Dry film photoresist and application thereof - Google Patents
Dry film photoresist and application thereof Download PDFInfo
- Publication number
- CN111123647A CN111123647A CN202010035171.3A CN202010035171A CN111123647A CN 111123647 A CN111123647 A CN 111123647A CN 202010035171 A CN202010035171 A CN 202010035171A CN 111123647 A CN111123647 A CN 111123647A
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- CN
- China
- Prior art keywords
- dry film
- film photoresist
- chain
- parts
- compounds
- 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.)
- Granted
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 46
- 239000000178 monomer Substances 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 15
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 13
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 13
- -1 acrylic ester Chemical class 0.000 claims abstract description 13
- 239000000654 additive Substances 0.000 claims abstract description 10
- 230000000996 additive effect Effects 0.000 claims abstract description 9
- 125000004386 diacrylate group Chemical group 0.000 claims abstract description 9
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 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 9
- 239000003112 inhibitor Substances 0.000 claims description 6
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 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
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 3
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- MTRFEWTWIPAXLG-UHFFFAOYSA-N 9-phenylacridine Chemical class C1=CC=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 MTRFEWTWIPAXLG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 150000008366 benzophenones Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 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 claims 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- 230000000873 masking effect Effects 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 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 3
- 239000000203 mixture Substances 0.000 description 3
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- GUOVBFFLXKJFEE-UHFFFAOYSA-N 2h-benzotriazole-5-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NNN=C21 GUOVBFFLXKJFEE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000009713 electroplating Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 2
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- AXYQEGMSGMXGGK-UHFFFAOYSA-N 2-phenoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1 AXYQEGMSGMXGGK-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- SGSKTOKJZHJRCN-UHFFFAOYSA-N 4-chlorothioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2 SGSKTOKJZHJRCN-UHFFFAOYSA-N 0.000 description 1
- IKVYHNPVKUNCJM-UHFFFAOYSA-N 4-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(C)C)=CC=C2 IKVYHNPVKUNCJM-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-O N-dimethylethanolamine Chemical compound C[NH+](C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-O 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- YYGBVRCTHASBKD-UHFFFAOYSA-M methylene green Chemical compound [Cl-].C1=CC(N(C)C)=C([N+]([O-])=O)C2=[S+]C3=CC(N(C)C)=CC=C3N=C21 YYGBVRCTHASBKD-UHFFFAOYSA-M 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012546 transfer Methods 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
- H05K3/061—Etching masks
- H05K3/064—Photoresists
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
Abstract
The invention discloses a dry film photoresist and application thereof. The dry film photoresist comprises the following components in parts by mass: 50-70 parts of alkali-soluble acrylic resin, 20-50 parts of photopolymerization monomer, 0.1-3 parts of photoinitiator and a proper amount of additive; wherein the photopolymerization monomer consists of long-chain diacrylate containing diphenyl sulfide and short-chain acrylate; the short-chain acrylic ester is acrylic ester with the main chain carbon number less than or equal to 16. The invention also discloses application of the dry film photoresist in preparing photosensitive dry films and printed circuit boards. The photosensitive dry film prepared by the dry film photoresist has the advantages of high photosensitive speed, high resolution, good hole masking performance and wide market prospect.
Description
Technical Field
The invention relates to the technical field of photosensitive materials, in particular to a dry film photoresist and application thereof.
Background
The dry film is a photosensitive material, consists of three parts of a polyester film, a photoresist film and a polyethylene protective film, is widely applied to pattern electroplating processes of circuit board printing and the like, and is used for manufacturing precise fine wires and the like. In the manufacture of a printed wiring board, a dry film resist is first bonded to a copper substrate, and the dry film resist is covered with a mask having a predetermined pattern, followed by pattern exposure. Then, using weak alkaline aqueous solution as developing solution to remove unexposed part, then implementing etching or electroplating treatment to form pattern, finally stripping off by remover to remove dry film solidified part so as to implement pattern transfer. Photoresist systems generally consist of four parts: photosensitive resin (photopolymer), photoinitiator, photopolymerization monomer and additive.
In recent years, as electronic devices have been made thinner and smaller, the line size of patterns such as printed circuit boards mounted thereon has been smaller, and the contact area between a substrate and a resin composition on which patterns have been formed has been becoming smaller. In order to manufacture such a narrow-pitch wiring pattern with higher yield, a higher demand is placed on the dry film resist.
JP 2001-117225A discloses a dry film photoresist with good hole-masking property, wherein a photopolymerizable monomer having more than 3 ethylenically unsaturated bonds per molecule is introduced into the photoresist, and these polyfunctional monomers are liable to cause shrinkage during curing, thereby affecting the hole-masking and plating properties. US7517636 reports a new dry film with good hole-masking ability and stripping properties, but unfortunately the presence of long alkoxy chain acrylate monomers limits the resolution enhancement. US5744282 mentions that when using a photopolymerizable monomer such as isocyanuric acid, urethane, etc., a certain flexibility is exhibited. The current commercial applications require further improvement in flexibility and require maintaining the peeling ability of the cured film; CN99126102A reports a photosensitive dry film with strong flexibility, but the resolution is low, and the current industry requirements are difficult to meet. CN104834182A reports a photosensitive dry film prepared by using alkali soluble resin with specific molecular weight and molecular weight distribution, which has good high resolution and excellent hole masking property, however, the alkali soluble resin in this scheme is prepared by reversible addition-fragmentation chain transfer polymerization, and is not easy to realize mass production.
Disclosure of Invention
In order to overcome the problems of the prior art, an object of the present invention is to provide a dry film photoresist, and an object of the present invention is to provide an application of the dry film photoresist.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a dry film photoresist comprises the following components in parts by mass: 50-70 parts of alkali-soluble acrylic resin, 20-50 parts of photopolymerization monomer, 0.1-3 parts of photoinitiator and a proper amount of additive; wherein the photopolymerization monomer consists of long-chain diacrylate containing diphenyl sulfide and short-chain acrylate; the short-chain acrylic ester is acrylic ester with the main chain carbon number less than or equal to 16.
Preferably, in the dry film photoresist, the alkali-soluble acrylic resin has a structural formula shown in formula (1):
in the formula (1), a, b and c independently represent the mass ratio of three units in the alkali-soluble resin; wherein a is 40-60; b is 18-23; c is 20-30; r1、R2、R3Each independently represents a H atom or a methyl group; r4Is an alkyl chain having 1 to 12 carbon atoms.
Preferably, in the dry film photoresist, the number average molecular weight of the alkali soluble acrylic resin is 80000-140000; more preferably, the number average molecular weight of the alkali-soluble acrylic resin is 80000 to 100000.
In such a dry film photoresist, the alkali-soluble acrylic resin may be prepared by a solution polymerization method, or a commercial resin may be directly used.
Preferably, in the photopolymerizable monomer of the dry film photoresist, the mass ratio of the long-chain diacrylate containing diphenyl sulfide to the short-chain acrylate is 1: (0.5-2).
Preferably, in the photopolymerizable monomer, the structural formula of the diphenyl sulfide-containing long-chain diacrylate is shown in formula (2):
in the formula (2), n is a positive integer.
Preferably, in formula (2), n is 1 to 3.
In the photopolymerization monomer, short-chain acrylate is acrylate with the main chain carbon atom number less than or equal to 16, and can be subjected to polymerization or crosslinking reaction after absorbing light energy. Such short chain acrylates may be di-monofunctional or multifunctional. Preferably, the short-chain acrylate is selected from at least one of bisphenol a di (meth) acrylate, ethoxylated (propoxylated) bisphenol a di (meth) acrylate, polyethylene (propylene) glycol diacrylate, ethoxylated (propoxylated) neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, ethoxylated (propoxylated) trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate; further preferably, the short-chain acrylate is at least one selected from the group consisting of 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol triacrylate and pentaerythritol tetraacrylate. In some preferred embodiments of the present invention, the short chain acrylate is trimethylolpropane triacrylate.
Preferably, in the dry film photoresist, the photoinitiator is at least one selected from benzoin compounds, benzophenone compounds, thioxanthone compounds, anthraquinone compounds, acylphosphine oxide compounds, thioxanthone compounds, hexaarylbisimidazole compounds and 9-phenylacridine compounds; further preferably, the photoinitiator is selected from the group consisting of benzoin bismethyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin phenyl ether, thioxanthone, 2-chlorothioxanthone, 4-chlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, benzophenone, 4' -bis (dimethylamino) benzophenone, 4' -bis (diethylamino) benzophenone, isopropylthioxanthone, 2-chlorothioxanthone, 2, 4-diethylthioxanthone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, ethyl N, N-dimethylbenzoate, dimethylaminoethyl benzoate, N-dimethylethanolamine, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 2 ' -bis (2-chlorophenyl) -4, 4', 5,5 ' -tetraphenyl-1, 2 ' -diimidazole, 2 ' -bis (2-bromo-5-methoxybenzene) -4, 4', 5,5 ' -tetraphenyldiimidazole, 2 ' -bis (2, 4-dichlorophenyl) -4, 4', 5,5 ' -tetraphenyldiimidazole, 2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4 ', 5 ' -diphenyl-1, 1 ' -diimidazole. In some preferred embodiments of the present invention, the photoinitiator is 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole and 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide.
Preferably, the additive is used in an amount of 0.1 to 0.6 parts by mass in the dry film photoresist.
Preferably, in the dry film photoresist, the additive is selected from one or more of a coloring agent, a developing agent, a leveling agent, an antioxidant, a plasticizer, a tackifier, a stabilizer, a corrosion inhibitor and a polymerization inhibitor. The additives belong to common raw materials in the field and can be selected and added according to actual needs. For example, the coloring agent may be selected from basic green 1, basic green 2, basic green 3, basic green 4, basic green 5, tribromomethylphenyl sulfone, phthalocyanine blue or methyl orange. The corrosion inhibitor can be selected from 4-hydroxybenzotriazole, 5-carboxyl benzotriazole, 1-thioglycerol, 2-mercaptopropionic acid or catechol. The polymerization inhibitor can be selected from hydroquinone or p-hydroxyanisole.
The invention also provides application of the dry film photoresist.
The application of the dry film photoresist in preparing a photosensitive dry film.
Further, a dry film photoresist may be used to prepare a resist layer of a photosensitive dry film.
A method for preparing a photosensitive dry film resist layer comprises the following steps: according to the composition of the dry film photoresist, alkali soluble acrylic resin, a photopolymerization monomer, a photoinitiator and an additive are mixed, then the mixture is mixed with a solvent to prepare a resist solution, and the resist solution is coated on the surface of a base film and cured to form a resist layer.
In the preparation method of the photosensitive dry film resist layer, the selected solvent is an organic solvent which can disperse or dissolve the components of the dry film photoresist and does not react with the components. Preferably, the solvent is at least one selected from the group consisting of alcohol solvents, ketone solvents, ether solvents, benzene solvents, and amide solvents; further preferably, the solvent is at least one selected from the group consisting of methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, ethylene glycol methyl ether, toluene, and N, N-dimethylformamide.
Preferably, in the method for preparing the photosensitive dry film resist, the solid content of the resist solution is 10 wt% to 92 wt%.
Preferably, in the method for preparing the photosensitive dry film resist, the base film is a polyester film; further preferably, the base film is a polyethylene terephthalate (PET) film.
Preferably, in the preparation method of the photosensitive dry film resist layer, the curing method is drying, specifically drying and molding at 60-80 ℃.
And (3) attaching a film to the surface of the prepared anti-corrosion layer to obtain the photosensitive dry film.
Preferably, the preparation method of the photosensitive dry film is to adhere a Polyethylene (PE) film to the surface of the resist layer to form the photosensitive dry film. The photosensitive dry film has a three-layer structure of a base film layer, a resist layer and a PE layer which are sequentially stacked.
The invention also provides application of the dry film photoresist in preparing a printed circuit board.
The invention has the beneficial effects that:
the photosensitive dry film prepared by the dry film photoresist has the advantages of high photosensitive speed, high resolution, good hole masking performance and wide market prospect.
Specifically, the present invention has the following advantages:
1. the invention selects alkali-soluble acrylic resin, combines the long-chain diacrylate containing diphenyl sulfide with the short-chain acrylate, and improves the resolution and the hole masking performance of the photoresist.
2. The long-chain diacrylate containing the diphenyl sulfide has a self-initiation effect, and the photosensitive speed of the photoresist can be improved by matching with a proper photoinitiator.
3. The dry film photoresist can reduce the occurrence of hole breakage phenomenon in the production of high-precision circuit boards, effectively improve the yield and efficiency of circuit board manufacture and reduce the manufacturing cost.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The starting materials, reagents or apparatus used in the examples and comparative examples were obtained from conventional commercial sources or can be obtained by a method of the prior art, unless otherwise specified. Unless otherwise indicated, the testing or testing methods are conventional in the art.
The main reagent names and abbreviations used in the examples and comparative examples are as follows:
TBHDA: 4,4' -dimercapto phenyl sulfide hexyl ester diacrylate;
TMPTA: trimethylolpropane triacrylate;
TCDDB: 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole;
omnirad TPO: 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide.
The structural formula of the reagent is shown in Table 1.
TABLE 1 names, abbreviations and structural formulae of reagents
Table 2 shows formulation composition tables of dry film photoresists of examples and comparative examples, and the usage units shown in table 2 are parts by mass.
TABLE 2 formulation tables for examples and comparative examples
| Raw materials | Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 2 |
| Acrylic resin | 66.5 | 66.5 | 66.5 | 66.5 | 66.5 |
| TBHDA | 5 | 10 | 15 | - | 5 |
| TMPTA | 15 | 10 | 5 | 20 | 15 |
| TCDDB | 2 | 2 | 2 | 2 | 3 |
| Omnirad TPO | 1 | 1 | 1 | 1 | - |
| Alkaline Green 1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Tribromomethyl phenyl sulfone | 0.29 | 0.29 | 0.29 | 0.29 | 0.29 |
| 5-carboxybenzotriazoles | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Hydroquinone | 0.01 | 0.01 | 0.01 | 0.01 | 0.01 |
| Acetone (II) | 10 | 10 | 10 | 10 | 10 |
The acrylic resin is alkali soluble acrylic resin, the structural formula is shown in formula (3), and the specific number average molecular weight is 100000.
The resist solutions of examples 1 to 3 and comparative examples 1 to 2 were obtained by mixing the components of the dry film photoresist except the solvent acetone in parts by mass, then mixing with acetone, stirring uniformly at room temperature, and removing impurities with a 200-mesh filter.
The resist solutions of examples 1 to 3 and comparative examples 1 to 2 were uniformly coated on a 15 μm PET film (double-sided heat seal type) using a bar coater, and after drying at 70 ℃, a resist layer was formed. Then, an 18 μm-thick PE film was heat-laminated on the resist surface using a rubber roll to obtain a dry film having a thickness of 40 μm of the photosensitive resin composition layer.
The prepared photosensitive dry film was tested:
a 40 μm thick photosensitive resin layer was used to evaluate the resolution and side profile after dry film development.
Film pasting: the film was applied using a 27-22808-A3 film press from Mega Electronics Ltd. of UK at a speed of 1 m/min and a temperature of 90 ℃.
Exposure: exposing with M552 exposure machine, measuring exposure energy with 21 lattice exposure ruler, and measuring exposure energy with 7-10 lattices and 30-60mJ/cm2。
And (3) developing: development was carried out using HM-BL258 developing machine of Guangzhou constant Electron Ltd. Gradually increasing the line width/line distance of the film selected by developing from 10 mu m to 100 mu m; the developing solution is 1% sodium carbonate aqueous solution, the developing temperature is 30 ℃, the developing pressure is 1.8bar, and the developing speed is 1.5 m/min.
The samples were observed by SEM at 500 x magnification.
Evaluation of photosensitive speed: the dry film exposure speed was measured by using a UVE-HSP5K manual parallel light exposure machine of Histo opto-electronic technology Co., Ltd, Dongguan.
And (3) evaluating the resolution: after exposure and development were performed using a photomask of a wiring pattern with an equal Line pitch and an equal Line width of Line/Space of 10/10 to 100/100 μm, observation was performed using an optical microscope, and the minimum Line width at which the side profile was good and the full development was clear was evaluated.
Evaluation of adhesion: after exposure and development were performed using a photomask having a Line/Space of n/400(n is 10 to 50) μm wiring pattern, observation was performed using an optical microscope, and the minimum Line width with good side profile and complete and clear Line was evaluated.
Evaluation of hole-masking ability: the dry film resist was peeled off the protective film and laminated on a multi-well plate, wherein 100 triple wells (16X 6mm) having a diameter of 6mm and 100 quadruple wells (21X 6mm) having a diameter of 6mm were formed. And (4) exposing by using exposure energy when the number of the photosensitive grids is 8, developing by using 4 times of the shortest developing time, and counting the hole breaking rate.
The test evaluation results are shown in table 3.
TABLE 3 test evaluation results
From the results in table 3, it can be seen that: compared with the samples of comparative examples 1-2, the samples of examples 1-3 have the advantages of smaller exposure energy, higher photospeed, higher resolution, lower porosity of 6mm triple holes (16 × 6mm) and 6mm quadruple holes (21 × 6mm), and better hole masking performance. It can be seen that the dry film photoresist of the present invention has higher quality.
In practical application, the dry film photoresist can reduce the occurrence of hole breaking phenomenon in the production of high-precision circuit boards, effectively improve the yield and efficiency of circuit board manufacturing and reduce the manufacturing cost. The dry film photoresist can be widely applied to the fields of manufacturing of printed circuit boards, lead frames and the like, manufacturing of semiconductor packages and the like.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A dry film photoresist, characterized by: the paint comprises the following components in parts by mass: 50-70 parts of alkali-soluble acrylic resin, 20-50 parts of photopolymerization monomer, 0.1-3 parts of photoinitiator and a proper amount of additive;
the photopolymerization monomer consists of long-chain diacrylate containing diphenyl sulfide and short-chain acrylate; the short-chain acrylic ester is acrylic ester with the main chain carbon atom number less than or equal to 16.
2. The dry film photoresist according to claim 1, wherein: the structural formula of the alkali-soluble acrylic resin is shown as the formula (1):
in the formula (1), a is 40-60; b is 18-23; c is 20-30; r1、R2、R3Each independently represents a H atom or a methyl group; r4Is an alkyl chain having 1 to 12 carbon atoms.
3. The dry film photoresist according to claim 1, wherein: in the photopolymerization monomer, the mass ratio of the long-chain diacrylate containing the diphenyl sulfide to the short-chain acrylate is 1: (0.5-2).
4. The dry film photoresist according to claim 3, wherein: the structural formula of the long-chain diacrylate containing the diphenyl sulfide is shown as the formula (2):
(2) (ii) a In the formula (2), n is a positive integer.
5. The dry film photoresist according to claim 3, wherein: the short-chain acrylate is selected from at least one of bisphenol A di (methyl) acrylate, ethoxylated (propylene oxide) bisphenol A di (methyl) acrylate, polyethylene (propylene) glycol diacrylate, ethoxylated (propylene oxide) neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, ethoxylated (propylene oxide) trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate and dipentaerythritol hexaacrylate.
6. The dry film photoresist according to claim 1, wherein: the photoinitiator is at least one selected from benzoin compounds, benzophenone compounds, thioxanthone compounds, anthraquinone compounds, acylphosphine oxide compounds, thioxanthone compounds, hexaarylbisimidazole compounds and 9-phenylacridine compounds.
7. The dry film photoresist according to claim 1, wherein: the additive is used in an amount of 0.1 to 0.6 parts by mass.
8. The dry film photoresist according to claim 7, wherein: the additive is selected from one or more of a coloring agent, a developing agent, a leveling agent, an antioxidant, a plasticizer, a tackifier, a stabilizer, a corrosion inhibitor and a polymerization inhibitor.
9. Use of the dry film photoresist according to any one of claims 1 to 8 for preparing a photosensitive dry film.
10. Use of the dry film photoresist of any one of claims 1 to 8 for the preparation of printed circuit boards.
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