CN112485968A - Photosensitive resin composition, dry film, and printed wiring board having photo-cured product of photosensitive resin composition - Google Patents
Photosensitive resin composition, dry film, and printed wiring board having photo-cured product of photosensitive resin composition Download PDFInfo
- Publication number
- CN112485968A CN112485968A CN202010956244.2A CN202010956244A CN112485968A CN 112485968 A CN112485968 A CN 112485968A CN 202010956244 A CN202010956244 A CN 202010956244A CN 112485968 A CN112485968 A CN 112485968A
- Authority
- CN
- China
- Prior art keywords
- photosensitive resin
- compound
- resin composition
- mass
- phenolic hydroxyl
- 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
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- 239000011342 resin composition Substances 0.000 title claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 81
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 52
- 229920005989 resin Polymers 0.000 claims abstract description 51
- 239000011347 resin Substances 0.000 claims abstract description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 50
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 49
- 239000011574 phosphorus Substances 0.000 claims abstract description 47
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 45
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 40
- 239000011593 sulfur Substances 0.000 claims abstract description 40
- 239000003999 initiator Substances 0.000 claims abstract description 27
- 239000003085 diluting agent Substances 0.000 claims abstract description 22
- 239000004593 Epoxy Substances 0.000 claims abstract description 16
- -1 oxime ester Chemical class 0.000 claims description 43
- 238000007747 plating Methods 0.000 abstract description 46
- 239000003513 alkali Substances 0.000 abstract description 34
- 230000035945 sensitivity Effects 0.000 abstract description 20
- 239000010408 film Substances 0.000 description 77
- 239000003822 epoxy resin Substances 0.000 description 64
- 229920000647 polyepoxide Polymers 0.000 description 64
- 238000000576 coating method Methods 0.000 description 32
- 239000011248 coating agent Substances 0.000 description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 29
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 21
- 229910052737 gold Inorganic materials 0.000 description 21
- 239000010931 gold Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 229910000679 solder Inorganic materials 0.000 description 18
- 150000007519 polyprotic acids Polymers 0.000 description 17
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 14
- 239000003086 colorant Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- KTLIMPGQZDZPSB-UHFFFAOYSA-M diethylphosphinate Chemical compound CCP([O-])(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-M 0.000 description 4
- BEQVQKJCLJBTKZ-UHFFFAOYSA-M diphenylphosphinate Chemical compound C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 BEQVQKJCLJBTKZ-UHFFFAOYSA-M 0.000 description 4
- NXHKQBCTZHECQF-UHFFFAOYSA-N ethyl(methyl)phosphinic acid Chemical compound CCP(C)(O)=O NXHKQBCTZHECQF-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 150000002898 organic sulfur compounds Chemical class 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Polymers C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 239000013039 cover film Substances 0.000 description 3
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical class OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011417 postcuring Methods 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- VTFXHGBOGGGYDO-UHFFFAOYSA-N 2,4-bis(dodecylsulfanylmethyl)-6-methylphenol Chemical compound CCCCCCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCCCCCC)=C1 VTFXHGBOGGGYDO-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 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 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-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
- 239000004925 Acrylic resin Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000038 blue colorant Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000000040 green colorant Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- OADYBSJSJUFUBR-UHFFFAOYSA-N octanedial Chemical compound O=CCCCCCCC=O OADYBSJSJUFUBR-UHFFFAOYSA-N 0.000 description 2
- 239000001061 orange colorant Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 description 1
- SGXRTWRRYSEZLP-UHFFFAOYSA-N (2-hydroxyphenyl) diphenyl phosphate Chemical compound OC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 SGXRTWRRYSEZLP-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 description 1
- YRTNMMLRBJMGJJ-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;hexanedioic acid Chemical compound OCC(C)(C)CO.OC(=O)CCCCC(O)=O YRTNMMLRBJMGJJ-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 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
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- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 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
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical class C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- VRRIVXLVXXAHJA-UHFFFAOYSA-N tris(2,3,4-tribromophenyl) phosphate Chemical compound BrC1=C(Br)C(Br)=CC=C1OP(=O)(OC=1C(=C(Br)C(Br)=CC=1)Br)OC1=CC=C(Br)C(Br)=C1Br VRRIVXLVXXAHJA-UHFFFAOYSA-N 0.000 description 1
- MHEGXVLDEDJADA-UHFFFAOYSA-N tris(2,3,4-trimethylphenyl) phosphate Chemical compound CC1=C(C)C(C)=CC=C1OP(=O)(OC=1C(=C(C)C(C)=CC=1)C)OC1=CC=C(C)C(C)=C1C MHEGXVLDEDJADA-UHFFFAOYSA-N 0.000 description 1
- LRSNDFOWYYKLHB-UHFFFAOYSA-N tris(2,3-dibromophenyl) phosphate Chemical compound BrC1=CC=CC(OP(=O)(OC=2C(=C(Br)C=CC=2)Br)OC=2C(=C(Br)C=CC=2)Br)=C1Br LRSNDFOWYYKLHB-UHFFFAOYSA-N 0.000 description 1
- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- SPUXJWDKFVXXBI-UHFFFAOYSA-N tris(2-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)(C)C)OC1=CC=CC=C1C(C)(C)C SPUXJWDKFVXXBI-UHFFFAOYSA-N 0.000 description 1
- LKOCAGKMEUHYBV-UHFFFAOYSA-N tris(3-bromo-3-chloropropyl) phosphate Chemical compound ClC(Br)CCOP(=O)(OCCC(Cl)Br)OCCC(Cl)Br LKOCAGKMEUHYBV-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001060 yellow colorant Substances 0.000 description 1
- PJEUXMXPJGWZOZ-UHFFFAOYSA-L zinc;diphenylphosphinate Chemical compound [Zn+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 PJEUXMXPJGWZOZ-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/144—Polymers containing more than one epoxy group per molecule
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- 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
- H05K3/10—Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern
- H05K3/12—Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern using thick film techniques, e.g. printing techniques to apply the conductive material or similar techniques for applying conductive paste or ink patterns
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Abstract
The purpose of the present invention is to provide a photosensitive resin composition capable of forming a photocurable film that does not impair high sensitivity to ultraviolet light and that has excellent plating properties such as alkali developability and gold-plating properties. A photosensitive resin composition comprising (A) a carboxyl group-containing photosensitive resin, (B) an antioxidant, (C) a photopolymerization initiator, (D) a reactive diluent, and (E) an epoxy compound, wherein the antioxidant (B) contains at least 1 compound selected from the group consisting of (B1) a compound having a phenolic hydroxyl group and phosphorus, and (B2) a compound having a phenolic hydroxyl group and sulfur.
Description
Technical Field
The present invention relates to a photosensitive resin composition suitable for a coating material, for example, an insulating coating material, a dry film having a coating film obtained by applying the photosensitive resin composition to a film, and a printed wiring board coated with a photocured product obtained by photocuring the photosensitive resin composition.
Background
A conductive circuit pattern of a conductor (e.g., copper foil) is formed on a substrate, an electronic component is mounted on a land of the circuit pattern by soldering, and a circuit portion other than the land is covered with an insulating coating film as a protective film, that is, a solder resist film. As the insulating film, a photocurable film of a photosensitive resin composition containing a carboxyl group-containing photosensitive resin and a photopolymerization initiator is used. In addition, an antioxidant may be blended in the photosensitive resin composition in order to prevent yellowing of the photocurable film, prevent halation during photocuring reaction, stabilize the shape of the opening of the through-hole, and the like.
Therefore, in order to prevent yellowing of a photocurable film, prevent halation during photocuring reaction, and the like, for example, a photosensitive resin composition containing (a) a carboxyl group-containing photosensitive resin, (B) a phenol compound, (C) an organic sulfur compound, (D) a photopolymerization initiator, (E) a diluent, (F) an epoxy compound, and (G) a colorant has been proposed as a photosensitive resin composition containing an antioxidant (patent document 1). In patent document 1, (B) a phenol compound and (C) an organic sulfur compound are blended as antioxidants to prevent yellowing of a photocurable film and prevent halation during a photocuring reaction.
On the other hand, high resolution is sometimes required for a solder resist film due to miniaturization of electronic components mounted on a printed circuit board, high-density mounting of electronic components, and the like. In order to improve the resolution of a solder resist film, a photosensitive resin composition having high sensitivity to ultraviolet light is sometimes required. In order to achieve high sensitivity of the photosensitive resin composition, an oxime ester photopolymerization initiator may be used as the photopolymerization initiator.
However, when an oxime ester photopolymerization initiator is used, the sensitivity of the photosensitive resin composition becomes too high, and even when an antioxidant such as a phenol compound or an organic sulfur compound is added, halation cannot be sufficiently suppressed, and for example, a small-diameter opening portion of a through hole is not developed, and thus, there is room for improvement in alkali developability.
In addition, when a photosensitive resin composition is photocured in a case where the influence of oxygen inhibition is small (for example, a state where a resin film such as PET is laminated on a coating film of the photosensitive resin composition), if an oxime ester photopolymerization initiator is used, ultraviolet rays reach an undesired coating film region, a photocuring reaction of the coating film proceeds excessively, and a defect such as scum may occur in the photocured film. If a defect such as scum occurs in the photo-cured film, for example, when plating treatment such as gold plating is performed on the photo-cured film of the photosensitive resin composition formed on the conductor, unevenness occurs in the plating film such as a gold plating film, and the plating film may not be adhered and fixed. Therefore, there is room for improvement in plating properties such as gold plating properties in conventional photosensitive resin compositions containing an antioxidant such as a phenolic compound or an organic sulfur compound.
Documents of the prior art
Patent document
Patent document 1: JP2011-70108A publication
Disclosure of Invention
Technical problem to be solved by the invention
In view of the above circumstances, an object of the present invention is to provide a photosensitive resin composition capable of forming a photocurable film having excellent platability such as alkali developability and gold-plating property without impairing high sensitivity to ultraviolet rays.
Means for solving the problems
The invention is constituted as follows.
[1] A photosensitive resin composition comprising (A) a carboxyl group-containing photosensitive resin, (B) an antioxidant, (C) a photopolymerization initiator, (D) a reactive diluent, and (E) an epoxy compound, wherein the antioxidant (B) contains at least 1 compound selected from the group consisting of (B1) a compound having a phenolic hydroxyl group and phosphorus, and (B2) a compound having a phenolic hydroxyl group and sulfur.
[2] The photosensitive resin composition according to [1], wherein the antioxidant (B) comprises the compound (B1) having a phenolic hydroxyl group and phosphorus.
[3] The photosensitive resin composition according to [1] or [2], wherein the antioxidant (B) is contained in an amount of 0.40 to 12.0 parts by mass based on 100 parts by mass of the carboxyl group-containing photosensitive resin (A).
[4] The photosensitive resin composition according to [2], wherein the compound having a phenolic hydroxyl group and phosphorus (B1) is contained in an amount of 2.0 parts by mass or more and 6.0 parts by mass or less based on 100 parts by mass of the carboxyl group-containing photosensitive resin (A).
[5] The photosensitive resin composition according to any one of [1] to [4], wherein the antioxidant (B) contains the compound (B2) having a phenolic hydroxyl group and sulfur, and the compound (B2) having a phenolic hydroxyl group and sulfur is contained in an amount of 0.50 parts by mass or more and 1.5 parts by mass or less based on 100 parts by mass of the carboxyl group-containing photosensitive resin (A).
[6] The photosensitive resin composition according to any one of [1] to [5], wherein the compound (B1) having a phenolic hydroxyl group and phosphorus is a compound represented by the following formula (1).
[7] The photosensitive resin composition according to any one of [1] to [6], wherein the compound (B2) having a phenolic hydroxyl group and sulfur is a compound of the following formula (2).
[8] The photosensitive resin composition according to any one of [1] to [7], wherein the (C) photopolymerization initiator contains an oxime ester photopolymerization initiator.
[9] A photocured product of the photosensitive resin composition according to any one of [1] to [8 ].
[10] A dry film having the photosensitive resin composition described in any one of [1] to [8 ].
[11] A printed wiring board having a photocured product of the photosensitive resin composition described in any one of [1] to [8 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the invention, the antioxidant (B) contains at least 1 compound selected from the group consisting of (B1) a compound having a phenolic hydroxyl group and phosphorus and (B2) a compound having a phenolic hydroxyl group and sulfur, and thus a photosensitive resin composition capable of forming a photocurable film having excellent plating properties such as gold plating properties without impairing high sensitivity to ultraviolet rays can be obtained. Further, according to the aspect of the present invention, since the (B) antioxidant contains at least 1 compound selected from the group consisting of the (B1) compound having a phenolic hydroxyl group and phosphorus and the (B2) compound having a phenolic hydroxyl group and sulfur, excellent alkali developability can be obtained, and therefore, alkali development of the non-exposed portion of the coating film of the photosensitive resin composition can be reliably achieved, and the coating film can be reliably removed by alkali development even in a small-diameter through hole opening.
According to the invention, the antioxidant (B) contains a compound having a phenolic hydroxyl group and phosphorus (B1), and the alkali developability is further improved, whereby the alkali development of the unexposed portion of the coating film of the photosensitive resin composition can be more reliably achieved.
According to the invention, by containing the antioxidant (B) in an amount of 0.40 to 12.0 parts by mass based on 100 parts by mass of the carboxyl group-containing photosensitive resin (a), the sensitivity to ultraviolet rays can be reliably improved, and the plating properties such as alkali developability and gold-plating properties can be further improved.
According to the invention, the compound having a phenolic hydroxyl group and phosphorus (B1) is contained in an amount of 2.0 parts by mass or more and 6.0 parts by mass or less based on 100 parts by mass of the carboxyl group-containing photosensitive resin (a), and the sensitivity and the plating property such as gold plating property are improved in a well-balanced manner.
According to the invention, the antioxidant (B) contains the compound having a phenolic hydroxyl group and sulfur (B2), and the compound having a phenolic hydroxyl group and sulfur (B2) is contained in an amount of 0.50 to 1.5 parts by mass per 100 parts by mass of the carboxyl group-containing photosensitive resin (a), whereby the alkali developability and the plating properties such as gold-plating properties are improved in a well-balanced manner.
Detailed Description
Next, the photosensitive resin composition of the present invention will be explained. The photosensitive resin composition of the present invention is a photosensitive resin composition containing (a) a carboxyl group-containing photosensitive resin, (B) an antioxidant containing at least 1 compound selected from the group consisting of (B1) a compound having a phenolic hydroxyl group and phosphorus, and (B2) a compound having a phenolic hydroxyl group and sulfur, (C) a photopolymerization initiator, (D) a reactive diluent, and (E) an epoxy compound.
(A) Carboxyl group-containing photosensitive resin
The chemical structure of the carboxyl group-containing photosensitive resin as the component (a) is not particularly limited, and examples thereof include resins having 1 or more photosensitive unsaturated double bonds and free carboxyl groups. Examples of the carboxyl group-containing photosensitive resin include a polybasic acid-modified radical-polymerizable unsaturated monocarboxylic epoxy resin such as a polybasic acid-modified epoxy (meth) acrylate obtained as follows: a radical polymerizable unsaturated monocarboxylic acid such as acrylic acid or methacrylic acid (hereinafter, sometimes referred to as "(meth) acrylic acid") is reacted with at least a part of epoxy groups of a polyfunctional epoxy resin having 2 or more epoxy groups in 1 molecule to obtain a radical polymerizable unsaturated monocarboxylic epoxy resin such as epoxy (meth) acrylate, and a polybasic acid and/or a polybasic acid anhydride is reacted with the generated hydroxyl groups to obtain the epoxy resin.
The chemical structure of the polyfunctional epoxy resin is not particularly limited as long as it is an epoxy resin having 2 or more functions. The epoxy equivalent of the polyfunctional epoxy resin is not particularly limited, and for example, the upper limit of the epoxy equivalent is preferably 3000g/eq, more preferably 2000g/eq, and particularly preferably 1500 g/eq. On the other hand, the lower limit of the epoxy equivalent is preferably 100g/eq, and particularly preferably 200 g/eq.
Examples of the resin type of the polyfunctional epoxy resin include a phenol novolac type epoxy resin such as a bisphenol a type epoxy resin and a bisphenol F type epoxy resin, a rubber modified epoxy resin such as a biphenyl aralkyl type epoxy resin, a phenyl aralkyl type epoxy resin, a biphenyl type epoxy resin, a naphthalene type epoxy resin, a dicyclopentadiene type epoxy resin, and a silicone modified epoxy resin, a cresol novolac type epoxy resin such as an epsilon-caprolactone type epoxy resin and an o-cresol novolac type epoxy resin, a bisphenol a novolac type epoxy resin, a cyclic aliphatic polyfunctional epoxy resin, a glycidyl ester type polyfunctional epoxy resin, a glycidyl amine type polyfunctional epoxy resin, a heterocyclic type polyfunctional epoxy resin, a bisphenol modified novolac type epoxy resin, and a polyfunctional modified novolac type epoxy resin. In addition, the epoxy resin may be used in which a halogen atom such as Br or Cl is further introduced. The polyfunctional epoxy resin may be used alone, or 2 or more kinds of the polyfunctional epoxy resins may be used in combination.
The radical polymerizable unsaturated monocarboxylic acid is not particularly limited, and examples thereof include (meth) acrylic acid, crotonic acid, methylcrotonic acid, angelic acid, cinnamic acid and the like. Among them, (meth) acrylic acid is preferable from the viewpoint of availability and handling properties. The radical polymerizable unsaturated monocarboxylic acid may be used alone, or 2 or more kinds of the radical polymerizable unsaturated monocarboxylic acids may be used in combination.
The method for reacting the polyfunctional epoxy resin and the radically polymerizable unsaturated monocarboxylic acid is not particularly limited, and for example, a method of dissolving the polyfunctional epoxy resin and the radically polymerizable unsaturated monocarboxylic acid in a non-reactive diluent such as an organic solvent and heating the solution can be mentioned.
The polybasic acid and/or polybasic acid anhydride and the hydroxyl group generated by the reaction of the polyfunctional epoxy resin and the radical polymerizable unsaturated monocarboxylic acid are subjected to addition reaction, thereby introducing a free carboxyl group into the radical polymerizable unsaturated monocarboxylic epoxy resin. The chemical structures of the polybasic acid and the polybasic acid anhydride are not particularly limited, and any saturated or unsaturated structure may be used. Examples of the polybasic acid include succinic acid, maleic acid, adipic acid, citric acid, phthalic acid, tetrahydrophthalic acids such as tetrahydrophthalic acid, 3-methyltetrahydrophthalic acid, 4-methyltetrahydrophthalic acid, 3-ethyltetrahydrophthalic acid and 4-ethyltetrahydrophthalic acid, hexahydrophthalic acid, 3-methylhexahydrophthalic acid, hexahydrophthalic acids such as 4-methylhexahydrophthalic acid, 3-ethylhexahydrophthalic acid and 4-ethylhexahydrophthalic acid, tetrahydrophthalic acids such as methyltetrahydrophthalic acid, endomethylenetetrahydrophthalic acid and methylendomethylenetetrahydrophthalic acid, trimellitic acid, pyromellitic acid and diglycolic acid. The polybasic acid anhydrides include acid anhydrides of the above-mentioned various polybasic acids. The above-mentioned compounds may be used alone or 2 or more kinds thereof may be used in combination.
The method of reacting the radical polymerizable unsaturated monocarboxylic acid epoxy resin and the polybasic acid and/or polybasic acid anhydride is not particularly limited, and examples thereof include a method of dissolving the radical polymerizable unsaturated monocarboxylic acid epoxy resin and the polybasic acid and/or polybasic acid anhydride in a non-reactive diluent such as an organic solvent and heating the solution.
The polybasic acid-modified unsaturated monocarboxylic acid-based epoxy resin can be used as a carboxyl group-containing photosensitive resin. Further, a polybasic acid-modified radical-polymerizable unsaturated monocarboxylic acid-based epoxy resin, which is obtained by addition reaction of a compound having 1 or more radical-polymerizable unsaturated groups and epoxy groups with a part of the carboxyl groups of the polybasic acid-modified unsaturated monocarboxylic acid-based epoxy resin obtained as described above and to which further radical-polymerizable unsaturated groups are added, can be used as the carboxyl group-containing photosensitive resin. The polybasic acid modified, free radical polymerizable, unsaturated, monocarboxylic acid based epoxy resin to which a free radical polymerizable unsaturated group is further added has a chemical structure in which a side chain of the polybasic acid modified, unsaturated, monocarboxylic acid based epoxy resin is further introduced into a free radical polymerizable unsaturated group, and therefore, the carboxyl group-containing photosensitive resin has further improved sensitivity as compared with the polybasic acid modified, unsaturated, monocarboxylic acid based epoxy resin.
Examples of the compound having 1 or more radical polymerizable unsaturated groups and epoxy groups include glycidyl compounds. Examples of the glycidyl compound include glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, pentaerythritol triacrylate monoglycidyl ether, pentaerythritol trimethacrylate monoglycidyl ether, and the like. The glycidyl compound may have 1 glycidyl group or a plurality of glycidyl groups in 1 molecule. The compound having 1 or more radical polymerizable unsaturated groups and epoxy groups may be used alone or 2 or more compounds may be used in combination.
The method of reacting the polybasic acid-modified unsaturated monocarboxylic acid-based epoxy resin with a compound having 1 or more radically polymerizable unsaturated groups and epoxy groups such as a glycidyl compound is not particularly limited, and examples thereof include a method of dissolving the polybasic acid-modified unsaturated monocarboxylic acid-based epoxy resin and the compound having 1 or more radically polymerizable unsaturated groups and epoxy groups in a non-reactive diluent such as an organic solvent and heating the solution.
The acid value of the carboxyl group-containing photosensitive resin is not particularly limited, and for example, the lower limit thereof is preferably 30mgKOH/g, and particularly preferably 40mgKOH/g, from the viewpoint of development with an alkali. On the other hand, for example, from the viewpoint of preventing the dissolution of the exposed portion by the alkali developing solution, the upper limit of the acid value of the carboxyl group-containing photosensitive resin is preferably 200mgKOH/g, and from the viewpoint of reliably preventing the deterioration of the moisture resistance and insulation reliability of the photo-cured product, it is particularly preferably 150 mgKOH/g.
The mass average molecular weight of the carboxyl group-containing photosensitive resin is not particularly limited, and the lower limit thereof is preferably 6000, more preferably 7000, and particularly preferably 8000, from the viewpoint of, for example, the toughness and the finger-touch drying property of the photo-cured product. On the other hand, for example, from the viewpoint of alkali development, the upper limit of the mass average molecular weight of the carboxyl group-containing photosensitive resin is preferably 200000, more preferably 100000, and particularly preferably 50000. The "mass average molecular weight" refers to a mass average molecular weight measured by Gel Permeation Chromatography (GPC) at normal temperature and calculated by polystyrene conversion.
The carboxyl group-containing photosensitive resin may be prepared by the above reaction step using the above components, or a commercially available carboxyl group-containing photosensitive resin may be used. Examples of commercially available carboxyl group-containing photosensitive resins include "KAYARAD ZAR-2000", "KAYARAD ZFR-1122", "KAYARAD FLX-2089", "KAYARAD ZCR-1569H" (manufactured by Kakko Kagaku K.K.), "CYCLOMER P (ACA) Z-250" (Daicel Allnex Ltd.), "SP-4621" (Showa Denko K.K.). The carboxyl group-containing photosensitive resin may be used alone, or 2 or more kinds of the carboxyl group-containing photosensitive resins may be used in combination.
(B) Antioxidant agent
As the antioxidant of the component (B), at least 1 compound selected from the group consisting of (B1) a compound having a phenolic hydroxyl group and phosphorus and (B2) a compound having a phenolic hydroxyl group and sulfur is used. By using at least 1 compound selected from the group consisting of (B1) a compound having a phenolic hydroxyl group and phosphorus and (B2) a compound having a phenolic hydroxyl group and sulfur as an antioxidant of component (B), a photosensitive resin composition capable of forming a photocurable film which does not impair high sensitivity to active energy rays such as ultraviolet rays and is excellent in plating properties such as gold plating properties can be obtained, and furthermore, halation can be sufficiently prevented to obtain excellent alkali developability, and therefore, unexposed portions of a coating film of the photosensitive resin composition can be reliably removed by alkali development, and the coating film can be reliably removed by alkali development even in a small-diameter through hole opening portion or fine pad portion.
Examples of the compound having a phenolic hydroxyl group and phosphorus as the component (B1) include compounds having a phenolic hydroxyl group in the skeleton and a phosphorus atom represented by the formula P (OR)1)(OR2)(OR3)(R1、R2、R3Is an organic group) of a phosphite (phosphite) structure. As a skeleton including a phenolic hydroxyl group and a group consisting of P (OR)1)(OR2)(OR3) The phosphite ester structure compound includes, for example, a compound represented by the following formula (1).
The compound may have a phenolic hydroxyl group obtained by substituting a butyl group of the formula (1) with hydrogen, an alkyl group having 1 to 3 carbon atoms, or an alkyl group having 5 to 10 carbon atoms, and phosphorus, or may have a phenolic hydroxyl group obtained by substituting a methyl group of the formula (1) with hydrogen or an alkyl group having 2 to 10 carbon atoms, and phosphorus. The compound represented by the formula (1) includes "Sumilizer GP" (sumitomo chemical co.
As the compound having a phenolic hydroxyl group and a sulfur as the component (B2), there may be mentioned, for example, a substituted group-R of phenol4-S-R5(in the formula, R4Represents a hydrocarbon having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, R5Represents a carbon number of 5 to 20, preferablyA hydrocarbon having 10 to 15 carbon atoms. ) A substituted compound. substituent-R4-S-R5The number of (a) is at least 1, preferably 2.
As phenolate-R4-S-R5Examples of the substituted compound include compounds represented by the following formula (2).
Examples of the compound represented by the above formula (2) include "Irganox 1726" (basf corporation).
The photosensitive resin composition of the present invention may be used together with a compound having a phenolic hydroxyl group and phosphorus and a compound having a phenolic hydroxyl group and sulfur, or may be used together with any of a compound having a phenolic hydroxyl group and phosphorus and a compound having a phenolic hydroxyl group and sulfur. Among them, a compound having a phenolic hydroxyl group and phosphorus is preferable in that the alkali developability can be further improved and the unexposed portion of the coating film of the photosensitive resin composition can be more reliably removed by alkali development.
The amount of at least 1 compound selected from the group consisting of a compound having a phenolic hydroxyl group and phosphorus and a compound having a phenolic hydroxyl group and sulfur is not particularly limited, and the lower limit value thereof is preferably 0.40 parts by mass, more preferably 0.50 parts by mass, even more preferably 1.0 part by mass, and particularly preferably 2.0 parts by mass, relative to 100 parts by mass of the carboxyl group-containing photosensitive resin (solid content, the same applies hereinafter) in view of further improving the plating property such as gold plating property. On the other hand, from the viewpoint of reliably improving the sensitivity to ultraviolet light and obtaining excellent alkali developability, the upper limit of the amount of at least 1 compound selected from the group consisting of a compound having a phenolic hydroxyl group and phosphorus and a compound having a phenolic hydroxyl group and sulfur is preferably 12.0 parts by mass, more preferably 10.0 parts by mass, and particularly preferably 5.0 parts by mass, relative to 100 parts by mass of the carboxyl group-containing photosensitive resin.
In addition, in the case where the compound having a phenolic hydroxyl group and phosphorus is blended and the compound having a phenolic hydroxyl group and sulfur is not blended, the lower limit of the blending amount of the compound having a phenolic hydroxyl group and phosphorus is preferably 1.0 part by mass, more preferably 1.5 parts by mass, and particularly preferably 2.0 parts by mass with respect to 100 parts by mass of the carboxyl group-containing photosensitive resin, from the viewpoint of further improving the plating property such as gold-plating property. On the other hand, in the case where the compound having a phenolic hydroxyl group and phosphorus is blended and the compound having a phenolic hydroxyl group and sulfur is not blended, the upper limit of the blending amount of the compound having a phenolic hydroxyl group and phosphorus is preferably 10.0 parts by mass, more preferably 7.5 parts by mass, further preferably 6.0 parts by mass, and particularly preferably 5.0 parts by mass with respect to 100 parts by mass of the carboxyl group-containing photosensitive resin, from the viewpoint of further improving the sensitivity.
In addition, when the compound having a phenolic hydroxyl group and sulfur is blended and the compound having a phenolic hydroxyl group and phosphorus is not blended, the lower limit value of the compound having a phenolic hydroxyl group and sulfur is preferably 0.50 parts by mass, and particularly preferably 0.75 parts by mass, relative to 100 parts by mass of the carboxyl group-containing photosensitive resin, from the viewpoint of further improving the plating property such as gold-plating property. On the other hand, when the compound having a phenolic hydroxyl group and sulfur is blended and the compound having a phenolic hydroxyl group and phosphorus is not blended, the upper limit value of the compound having a phenolic hydroxyl group and sulfur is preferably 2.5 parts by mass, more preferably 2.0 parts by mass, and particularly preferably 1.5 parts by mass with respect to 100 parts by mass of the carboxyl group-containing photosensitive resin, from the viewpoint of further improving the alkali developability.
Further, as the antioxidant (B), a compound having a phenolic hydroxyl group and phosphorus (B1), a compound having a phenolic hydroxyl group and sulfur (B2), and an antioxidant other than the components (B1) and (B2) (hereinafter, may be referred to as "other antioxidant") may be used together, as necessary. Examples of the other antioxidants used together include a phenol-based antioxidant (hereinafter, sometimes referred to as a "phenol-based antioxidant") having no phosphorus and no sulfur, a phosphorus-based antioxidant (hereinafter, sometimes referred to as a "phosphorus-based antioxidant") having no phenolic hydroxyl group, a sulfur-based antioxidant (hereinafter, sometimes referred to as a "sulfur-based antioxidant") having no phenolic hydroxyl group, and the like.
Examples of the phenolic antioxidant include 3, 9-bis {2- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy ] -1, 1-dimethylethyl } -2,4,8, 10-tetraoxaspiro [5,5] undecane, 3, 9-bis {2- [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyloxy ] -1, 1-dimethylethyl } -2,4,8, 10-tetraoxaspiro [5,5] undecane, 3, 9-bis {2- [3- (3-isobutyl-4-hydroxy-5-methylphenyl) propionyloxy ]1, 1' -dimethylethyl } -2, hindered phenol antioxidants such as 4,8, 10-tetraoxaspiro [5,5] undecane, 3, 9-bis {2- [3- (4-hydroxy-5-methylphenyl) propionyloxy ]1,1 '-dimethylethyl } -2,4,8, 10-tetraoxaspiro [5,5] undecane, 3, 9-bis {2- [3- (3-tert-butyl-5-ethyl-4-hydroxyphenyl) propionyloxy ]1, 1' -dimethylethyl } -2,4,8, 10-tetraoxaspiro [5,5] undecane, and stearyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate. Examples of commercially available hindered phenol antioxidants include "Irganox 1010" (manufactured by Basff corporation).
Examples of the phosphorus-based antioxidant include tris (2, 4-di-t-butylphenyl) phosphite and the like commercially available as Irgafos 168 (Basff).
Examples of the sulfur-based antioxidant include organic sulfur-based compounds represented by the following general formula (I).
(R6-S-CH2CH2COOCH2)4C····(I)
(in the formula (I), R6Represents an alkyl group having 10 to 20 carbon atoms, 4R6May be the same or different. ) As R6That is, examples of the alkyl group having 10 to 20 carbon atoms include lauryl group, myristyl group, palmityl group, and stearyl group. Examples of commercially available sulfur antioxidants include "Sumilizer TP-D" (Sumitomo chemical Co., Ltd.).
The amount of the other antioxidant to be blended is not particularly limited, and the lower limit value is preferably 0.05 parts by mass, and particularly preferably 0.10 parts by mass, per 100 parts by mass of the carboxyl group-containing photosensitive resin, from the viewpoint of reliably contributing to the suppression of halation. On the other hand, from the viewpoint of reliably maintaining high sensitivity, the upper limit of the amount of the other antioxidant to be blended is preferably 2.0 parts by mass, and particularly preferably 1.0 part by mass, relative to 100 parts by mass of the carboxyl group-containing photosensitive resin.
(C) Photopolymerization initiator
The photopolymerization initiator as the component (C) is not particularly limited, and any photopolymerization initiator can be used. Examples of the photopolymerization initiator include 1, 2-octanedione, 1- [4- (phenylthio) -2- (O-benzoyloxime) ], ethanone, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -, 1- (O-acetyloxime), 2- (acetoxyiminomethyl) thioxanthen-9-one, 1, 8-octanedione, 1, 8-bis [ 9-ethyl-6-nitro-9H-carbazol-3-yl ] -, 1, 8-bis (O-acetyloxime), 1, 8-octanedione, 1, 8-bis [9- (2-ethylhexyl) -6-nitro-9H-carbazol-3-yl ] - Oxime ester photopolymerization initiators such as 1, 8-bis (O-acetyloxime), (Z) - (9-ethyl-6-nitro-9H-carbazol-3-yl) (4- ((1-methoxypropan-2-yl) oxy) -2-methylphenyl) methanone O-acetyloxime, and the like. The above-mentioned compounds may be used alone or 2 or more kinds thereof may be used in combination. The oxime ester photopolymerization initiator can impart high sensitivity to active energy rays such as ultraviolet rays to the photosensitive resin composition.
In the present invention, even when the oxime ester photopolymerization initiator is blended, the antioxidant (B) contains at least 1 compound selected from the group consisting of (B1) a compound having a phenolic hydroxyl group and phosphorus and (B2) a compound having a phenolic hydroxyl group and sulfur, and thus halation during the photocuring reaction can be prevented, and a photocured film having excellent plating properties such as alkali developability and gold-plating properties can be formed.
Further, photopolymerization initiators other than oxime ester photopolymerization initiators may be used, and examples thereof include phenylbis (2,4, 6-trimethylbenzoyl) phosphine oxide, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethylaminoacetophenone, 2-dimethoxy-2-phenylacetophenone, 2-diethoxy-2-phenylacetophenone, 1-benzyl-1- (dimethylamino) propyl-4-morpholinophenyl ketone, 2-methyl-4' - (methylthio) -2-morpholinophenyl acetone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, methyl ethyl ketone-1, methyl ketone-2-morpholinophenyl ether, methyl ethyl ketone-1, methyl ketone-2-methyl ketone-1- (4-morpholinophenyl) -ethyl ketone-, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 4- (2-hydroxyethoxy) phenyl-2- (hydroxy-2-propyl) ketone, benzophenone, p-phenyl benzophenone, 4' -bis (diethylamino) benzophenone, dichlorobenzophenone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 2-aminoanthraquinone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diethylthioxanthone, benzil dimethyl ketal, acetophenone dimethyl ketal, ethyl p-dimethylaminobenzoate, and the like. The above-mentioned compounds may be used alone or 2 or more kinds thereof may be used in combination.
The content of the photopolymerization initiator is not particularly limited, and is preferably 0.10 to 10 parts by mass, and particularly preferably 0.50 to 5.0 parts by mass, based on 100 parts by mass of the carboxyl group-containing photosensitive resin.
(D) Reactive diluents
The reactive diluent as the component (D) is, for example, a photopolymerizable monomer, and is a compound having at least 1, preferably 2 or more polymerizable double bonds per 1 molecule. The reactive diluent sufficiently photo-cures the photosensitive resin composition, and contributes to improvement of acid resistance, heat resistance, alkali resistance, and the like of a photo-cured product.
Examples of the reactive diluent include a monofunctional (meth) acrylate monomer and a 2-or more-functional (meth) acrylate monomer. Examples of the monofunctional (meth) acrylate monomer include 2-hydroxyethyl (meth) acrylate, phenoxyethyl (meth) acrylate, diethylene glycol mono (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, and caprolactone-modified (meth) acrylate. Examples of the 2-or more-functional (meth) acrylate monomer include 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol adipate di (meth) acrylate, hydroxypivalic acid neopentyl glycol di (meth) acrylate, dicyclopentyl di (meth) acrylate, ethylene oxide-modified phosphoric acid di (meth) acrylate, allylated cyclohexyl di (meth) acrylate, isocyanurate di (meth) acrylate, trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, propylene oxide-modified trimethylolpropane tri (meth) acrylate, and mixtures thereof, Tris (acryloyloxyethyl) isocyanurate, propionic acid-modified dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, urethane (meth) acrylate, and the like. The above-mentioned compounds may be used alone or 2 or more kinds thereof may be used in combination.
The amount of the reactive diluent is not particularly limited, but is preferably 5.0 to 100 parts by mass, and particularly preferably 10 to 30 parts by mass, based on 100 parts by mass of the carboxyl group-containing photosensitive resin.
(E) Epoxy compound
The epoxy compound as the component (E) is used to obtain a photocurable film having sufficient mechanical strength by increasing the crosslinking density of a photocurable product of the photosensitive resin composition. Examples of the epoxy compound include epoxy resins. Examples of the epoxy resin include a bisphenol F type epoxy resin such as a biphenyl type epoxy resin, a biphenyl aralkyl type epoxy resin, a bisphenol a type epoxy resin, and a tetramethyl bisphenol F type epoxy resin, a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, a dicyclopentadiene type epoxy resin, and an adamantane type epoxy resin. Among them, from the viewpoint of further improving the pot life, bisphenol a type epoxy resins, biphenyl type epoxy resins, and tetramethyl bisphenol F type epoxy resins are preferable, and biphenyl type epoxy resins and tetramethyl bisphenol F type epoxy resins are particularly preferable. The above-mentioned compounds may be used alone or 2 or more kinds thereof may be used in combination.
The amount of the epoxy compound to be blended is not particularly limited, and is preferably 5.0 to 100 parts by mass, and more preferably 10 to 50 parts by mass, per 100 parts by mass of the carboxyl group-containing photosensitive resin, from the viewpoint of reliably obtaining a photo-cured product having sufficient mechanical strength.
In addition to the components (a) to (E), other components such as an extender pigment, a flame retardant, a curing accelerator, an additive, a colorant, a non-reactive diluent, and the like may be appropriately blended as necessary in the photosensitive resin composition of the present invention.
Examples of the extender pigment include talc, barium sulfate, hydrophobic silica, alumina, aluminum hydroxide, mica, and the like. The flame retardant is used for imparting flame retardancy to a photo-cured product of the photosensitive resin composition of the present invention, and examples thereof include phosphorus flame retardants. Examples of the phosphorus-based flame retardant include halogen-containing phosphates such as tris (chloroethyl) phosphate, tris (2, 3-dichloropropyl) phosphate, tris (2-chloropropyl) phosphate, tris (2, 3-bromopropyl) phosphate, tris (bromochloropropyl) phosphate, 2, 3-dibromopropyl-2, 3-chloropropyl phosphate, tris (tribromophenyl) phosphate, tris (dibromophenyl) phosphate, and tris (tribromoneopentyl) phosphate; non-halogen lipid phosphates such as trimethyl phosphate, triethyl phosphate, tributyl phosphate, trioctyl phosphate, and tributoxyethyl phosphate; non-halogen aromatic phosphates such as triphenyl phosphate, cresyl diphenyl phosphate, ditolyl phenyl phosphate, tricresyl phosphate, trixylenyl phosphate, ditolyl diphenyl phosphate, tri (isopropyl phenyl) phosphate, isopropyl phenyl diphenyl phosphate, diisopropyl phenyl phosphate, tri (trimethylphenyl) phosphate, tri (tert-butylphenyl) phosphate, hydroxyphenyl diphenyl phosphate, octyl diphenyl phosphate, and the like; aluminum tris (diethylphosphinate), aluminum tris (methylethylphosphinate), aluminum tris (diphenylphosphinate), zinc bis (diethylphosphinate), zinc bis (methylethylphosphinate), zinc bis (diphenylphosphinate), titanyl bis (diethylphosphinate), titanium tetrakis (diethylphosphinate), titanyl bis (methylethylphosphinate), titanium tetrakis (methylethylphosphinate), titanyl bis (diphenylphosphinate), titanium tetrakis (diphenylphosphinate), metal salts of phosphinic acids such as titanium tetrakis (diphenylphosphinate), 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (hereinafter referred to as HCA), addition reaction products of HCA and acrylic esters, addition reaction products of HCA and epoxy resins, addition reaction products of HCA and hydroquinone, and other HCA-modified compounds, diphenylvinylphosphine oxide, triphenylphosphine oxide, and the like, Phosphine oxide compounds such as trialkylphosphine oxide and tris (hydroxyalkyl) phosphine oxide. Among them, organic phosphate flame retardants are preferable.
Examples of the curing accelerator include mercaptobenzoxazole and its derivatives, Dicyandiamide (DICY) and its derivatives, melamine and its derivatives, boron trifluoride-amine complex, organic acid hydrazide, Diaminomaleonitrile (DAMN) and its derivatives, guanamine and its derivatives, Amine Imide (AI), and polyamine. Examples of the additive include silicone-based, hydrocarbon-based, acrylic-based, and other defoaming agents, and polycarboxylic acid amides and other thixotropic agents.
The colorant is not particularly limited to pigments, and the like, and colorants of any color such as white colorant, blue colorant, green colorant, yellow colorant, violet colorant, black colorant, and orange colorant may be used. Examples of the colorant include titanium oxide (rutile type or anatase type) as a white colorant, an inorganic colorant such as carbon black or acetylene black as a black colorant, a phthalocyanine green as a green colorant, a phthalocyanine such as phthalocyanine blue or Lionol blue as a blue colorant, an anthraquinone, and an organic colorant such as diketopyrrolopyrrole as a chromophtal orange as an orange colorant.
The non-reactive diluent is used for adjusting the coating property and the drying property of the photosensitive resin composition. Examples of the non-reactive diluent include an organic solvent. Examples of the organic solvent include ketones such as methyl ethyl ketone and cyclohexanone, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, ethanol, propanol and cyclohexanol, alicyclic hydrocarbons such as cyclohexane and methylcyclohexane, petroleum solvents such as petroleum ether and naphtha, cellosolves such as cellosolve and butyl cellosolve, carbitols such as carbitol and butyl carbitol, esters such as ethyl acetate, butyl acetate, cellosolve acetate, butyl cellosolve acetate, carbitol acetate, butyl carbitol acetate, ethylene glycol acetate and ethyl diglycol acetate. The above-mentioned compounds may be used alone or 2 or more kinds thereof may be used in combination.
The method for producing the photosensitive resin composition of the present invention is not limited to a specific method, and for example, the photosensitive resin composition can be produced by mixing the above components at a predetermined ratio and then kneading or mixing the mixture at room temperature (room temperature) by a kneading means such as a triple roll, a ball mill, or a sand mill, or a stirring means such as a super mixer or a planetary mixer. Further, before the above-mentioned kneading or mixing, preliminary kneading or premixing may be carried out at room temperature (normal temperature) as required.
Next, an example of a method for using the photosensitive resin composition of the present invention will be described. Here, first, the following method is explained: a solder resist film is formed on a printed wiring board having a circuit pattern formed by etching a conductor foil, using a dry film coated with the photosensitive resin composition of the present invention.
The dry film is a laminated structure having a support film (e.g., a thermoplastic film such as a polyethylene terephthalate film or a polyester film), a solder resist layer coated on the support film, and a cover film (e.g., a polyethylene film or a polypropylene film) for protecting the solder resist layer. After a coating film is formed by applying the photosensitive resin composition of the present invention to a support film by a known method such as roll coating or bar coating, the coating film is dried, thereby forming a solder resist layer on the support film. Then, a dry film having a coating film of the photosensitive resin composition of the present invention can be produced by laminating a cover film on the formed solder resist layer.
The solder resist layer is laminated to the printed wiring board while peeling the cover film of the dry film, thereby forming a solder resist film on the printed wiring board. Then, if necessary, the photosensitive resin composition is pre-dried by heating at a temperature of about 70 to 120 ℃ for about 1 to 20 minutes to volatilize the non-reactive diluent (organic solvent) in the photosensitive resin composition, and the surface of the solder resist film is made non-tacky by volatilizing the non-reactive diluent (organic solvent) from the photosensitive resin composition. A negative film (transparent film) having a light-transmitting pattern at a portion other than a land of a circuit pattern is closely attached to a solder resist film to be formed, and ultraviolet rays (for example, in a wavelength range of 300nm to 400 nm) are irradiated from above the negative film. Then, the solder resist film is developed by removing the non-exposed region corresponding to the pad with a dilute aqueous alkali solution. As the developing method, a spray method, a shower method, or the like can be used, and as the dilute aqueous alkali solution used, for example, a 0.5 to 5 mass% aqueous sodium carbonate solution can be cited. After the development, a solder resist film having a desired pattern can be formed on the printed wiring board by post-curing (thermosetting treatment) at 130 to 170 ℃ for 20 to 80 minutes by a hot air circulating dryer or the like.
Next, as an example of a method for using the photosensitive resin composition of the present invention, a method for forming an insulating protective film (e.g., solder resist film) by applying the photosensitive resin composition to a printed wiring board will be described. The photosensitive resin composition of the present invention obtained as described above is applied to a printed wiring board having a circuit pattern in a desired thickness by other known coating methods such as screen printing, spray coating, bar coating, application, blade coating, doctor blade coating, roll coating, and gravure coating to form a coating film. Then, if necessary, the non-reactive diluent is subjected to preliminary drying by heating at a temperature of about 60 to 100 ℃ for 15 to 60 minutes to volatilize the non-reactive diluent, thereby forming a non-tacky coating film. Next, a base film having a light-transmitting pattern other than the land of the circuit pattern is closely attached to the coating film, and ultraviolet rays (for example, having a wavelength of 300nm to 400 nm) are irradiated from above the base film to photocure the coating film. Then, the non-exposed region corresponding to the pad is removed by a dilute alkali aqueous solution to develop the coating film. For the developing method, a spray method, a shower method, or the like is used, and examples of the dilute aqueous alkali solution used include a 0.5 to 5 mass% aqueous sodium carbonate solution. Then, post-curing (thermosetting treatment) is performed at 130 to 170 ℃ for 20 to 80 minutes by a hot air circulation dryer or the like, whereby a solder resist film having a target pattern can be formed on the printed wiring board.
Examples
Next, embodiments of the present invention will be described, but the present invention is not limited to the above embodiments unless the gist thereof is exceeded.
Examples 1 to 9 and comparative examples 1 to 3
The photosensitive resin compositions used in examples 1 to 9 and comparative examples 1 to 3 were prepared by mixing the components shown in Table 1 at the mixing ratios shown in Table 1 below and dispersing the mixture at room temperature (25 ℃ C.) using a triple roll. Unless otherwise specified, the blending amounts of the respective components shown in table 1 below are expressed by parts by mass. The blank column in table 1 below indicates that the component was not blended.
Hereinafter, each component in table 1 will be described in detail.
(A) Carboxyl group-containing photosensitive resin
KAYARAD ZAR-2000: 65% by mass of solid content (amount of resin) and Nippon Kabushiki Kaisha
KAYARAD ZAR-2000 is a polyacid-modified epoxy acrylate resin: the epoxy acrylate resin is obtained by reacting acrylic acid with at least a part of epoxy groups of an epoxy resin (bisphenol a type epoxy resin) to obtain an epoxy acrylate, and reacting a polybasic acid with hydroxyl groups formed from the epoxy acrylate.
(B) Antioxidant agent
Sumilizer gp: compound of formula (1) and Sumitomo chemical Co., Ltd
Irganox 1726: compound of formula (2), BASF
Irganox 1010: phenolic antioxidants, Basff Corp
Irgafos 168: phosphorus antioxidant, Basff Corp
(C) Photopolymerization initiator
NCI-831: oxime ester photopolymerization initiator and ADEKA corporation
OXE-02: oxime ester photopolymerization initiator, BASF corporation
(D) Reactive diluents
EBERCRYL 8405: dailusite Cyantte Co Ltd
(E) Epoxy compound
EPICRON 850-S: DIC corporation
Extender pigment
Hydilite H42M: showa Denko K.K
Flame retardant
Exolit OP-935: crainen Japan Co
Curing accelerator
Melamine: nissan chemical industry Co., Ltd
DICY-7: mitsubishi chemical corporation
Additive agent
X-50-1095C: antifoams, shin-Etsu chemical industries, Ltd
Coloring agent
Chromophtal DPP orange TR: ciba specialty Chemicals Co Ltd
Non-reactive diluents
EDGAC: sanyan finished product corporation
Process for producing test body
Using the prepared photosensitive resin composition, a test piece was produced in the following manner.
Substrate: glass epoxy substrate, "FR 4", copper foil thickness 25 μm
Substrate surface treatment: 5% by mass sulfuric acid treatment
Coating: screen printing
Pre-drying: using a BOX furnace at 80 ℃ for 20 minutes
Exposure: using a direct-scanning exposure machine (Nuvogo 800, Orbotech Co., Ltd.) at 100mJ/cm2～300mJ/cm2Is exposed under the exposure condition of
Alkali development: 1% by mass of Na2CO3The aqueous solution has a liquid temperature of 30 deg.C, a spray pressure of 0.2MPa, and a developing time of 60 s
Post-curing (heat treatment for main curing): 150 ℃ for 60 minutes
The thickness of the photocured film of the test body obtained in the above manner was 20 μm to 23 μm.
Evaluation item
(1) Sensitivity of light
In the test piece preparation step, a stepwise exposure meter (Kodak, 21-class) for measuring photosensitivity was set on the coated substrate after predrying at 80 ℃ for 20 minutes, and the substrate was subjected to 100mJ/cm by the stepwise exposure meter2The test piece is used as the exposure. After exposure, the use of 1 mass% of Na is represented by a number (number of stages)2CO3Spraying the aqueous solution at a spray pressure of 0.2MPaForce, development time of 60 seconds, the unremoved portion of the exposed portion after development. The larger the order number, the better the photosensitive characteristics.
(2) Alkali developability
In the test piece manufacturing step, a photosensitive resin composition is applied by a spray method instead of screen printing, and then the test piece is preliminarily dried at 80 ℃ at intervals of 20 minutes to 80 minutes and 10 minutes. The test piece was taken out from the pre-drying oven, developed under the alkali development conditions in the test piece production step, and the state of removal of the coating film after development was visually observed, and the longest pre-drying time of the test piece after removal of the coating film was measured.
(3) Gold plating property
Plating was performed using a commercially available electroless nickel plating bath and an electroless gold plating bath under conditions of 0.5 μm nickel and 0.03 μm gold. The state of gold plating was visually observed, and the gold plating property was evaluated on the following 4 grades.
O: the gold-plated surface has no abnormality.
And (delta): slightly uneven plating.
X: the whole has uneven gold plating.
X: producing non-attached immobilization of gold plating
The evaluation results are shown in table 1 below.
[ Table 1]
As shown in table 1 above, in examples 1 to 9 in which the compound having a phenolic hydroxyl group and phosphorus as the component (B1) or the compound having a phenolic hydroxyl group and sulfur as the component (B2) was blended as an antioxidant, a photocurable material having excellent sensitivity and excellent alkali developability and gold plating property was obtained. Further, it is understood from examples 4 and 7 that even when a phenol antioxidant is used together, a photo-cured product having excellent sensitivity and excellent alkali developability and gold plating property can be obtained. In particular, as is clear from comparison of examples 1 to 4 and 8 with examples 5 to 7 and 9, the compound having a phenolic hydroxyl group and phosphorus as the component (B1) can remove the coating film and further improve the alkali developability even if the predrying time is prolonged as compared with the compound having a phenolic hydroxyl group and sulfur as the component (B2).
In addition, the sensitivity was further improved in example 2 in which about 2 parts by mass of (B1) the compound having a phenolic hydroxyl group and phosphorus was blended with 100 parts by mass of the carboxyl group-containing photosensitive resin, in example 1 in which about 5 parts by mass of (B1) the compound having a phenolic hydroxyl group and phosphorus was blended with (B1) the compound having a phenolic hydroxyl group and phosphorus was blended with example 8. Further, example 2 in which about 2 parts by mass of (B1) the compound having a phenolic hydroxyl group and phosphorus was blended with 100 parts by mass of the carboxyl group-containing photosensitive resin was 300mJ/cm as compared with example 4 in which about 1 part by mass of (B1) the compound having a phenolic hydroxyl group and phosphorus was blended with the carboxyl group-containing photosensitive resin2The gold plating property is further improved.
Further, the alkali developability was further improved in example 5 in which about 1 part by mass of (B2) the compound having a phenolic hydroxyl group and sulfur was blended with 100 parts by mass of the carboxyl group-containing photosensitive resin, and in comparison with example 9 in which about 2 parts by mass of (B2) the compound having a phenolic hydroxyl group and sulfur was blended. Further, example 5 in which about 1 part by mass of (B2) the compound having a phenolic hydroxyl group and sulfur was blended with 100 parts by mass of the carboxyl group-containing photosensitive resin was 300mJ/cm as compared with example 6 in which about 0.5 part by mass of (B2) the compound having a phenolic hydroxyl group and sulfur2The gold plating property is further improved.
On the other hand, in comparative example 1 in which no antioxidant was blended, no gold plating property was obtained, and in comparative example 2 in which a phenol antioxidant was used as an antioxidant and comparative example 3 in which a phosphorus antioxidant was used, no gold plating property of 200mJ/cm was obtained2、300mJ/cm2Gold plating property.
Industrial applicability
The photosensitive resin composition of the present invention can form a photocurable film which does not impair high sensitivity to ultraviolet rays and is excellent in plating properties such as alkali developability and gold-plating properties, and therefore, is highly valuable in the field of protective films such as solder resists formed on printed wiring boards, particularly in the field of forming protective films such as solder resists using a photosensitive resin composition which achieves high sensitivity.
Claims (11)
1. A photosensitive resin composition comprising (A) a carboxyl group-containing photosensitive resin, (B) an antioxidant, (C) a photopolymerization initiator, (D) a reactive diluent, and (E) an epoxy compound,
the antioxidant (B) contains at least 1 compound selected from (B1) a compound having a phenolic hydroxyl group and phosphorus and (B2) a compound having a phenolic hydroxyl group and sulfur.
2. The photosensitive resin composition according to claim 1, wherein the antioxidant (B) comprises the compound (B1) having a phenolic hydroxyl group and phosphorus.
3. The photosensitive resin composition according to claim 1 or 2, wherein the antioxidant (B) is contained in an amount of 0.40 to 12.0 parts by mass based on 100 parts by mass of the carboxyl group-containing photosensitive resin (a).
4. The photosensitive resin composition according to claim 2, wherein the compound having a phenolic hydroxyl group and phosphorus (B1) is contained in an amount of 2.0 parts by mass or more and 6.0 parts by mass or less based on 100 parts by mass of the carboxyl group-containing photosensitive resin (a).
5. The photosensitive resin composition according to any one of claims 1 to 4, wherein the (B) antioxidant contains the (B2) compound having a phenolic hydroxyl group and sulfur, and the (B2) compound having a phenolic hydroxyl group and sulfur is contained in an amount of 0.50 parts by mass or more and 1.5 parts by mass or less based on 100 parts by mass of the (A) carboxyl group-containing photosensitive resin.
6. The photosensitive resin composition according to any one of claims 1 to 5, wherein the compound (B1) having a phenolic hydroxyl group and phosphorus is a compound of the following formula (1),
7. the photosensitive resin composition according to any one of claims 1 to 6, wherein the compound (B2) having a phenolic hydroxyl group and sulfur is a compound of the following formula (2),
8. the photosensitive resin composition according to any one of claims 1 to 7, wherein the (C) photopolymerization initiator contains an oxime ester photopolymerization initiator.
9. A photo-cured product of the photosensitive resin composition according to any one of claims 1 to 8.
10. A dry film having the photosensitive resin composition according to any one of claims 1 to 8.
11. A printed circuit board having a photocured product of the photosensitive resin composition according to any one of claims 1 to 8.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019165371A JP6986534B2 (en) | 2019-09-11 | 2019-09-11 | A printed wiring board having a photosensitive resin composition, a dry film having a photosensitive resin composition, and a photocured product of the photosensitive resin composition. |
| JP2019-165371 | 2019-09-11 |
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| Publication Number | Publication Date |
|---|---|
| CN112485968A true CN112485968A (en) | 2021-03-12 |
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| CN202010956244.2A Pending CN112485968A (en) | 2019-09-11 | 2020-09-11 | Photosensitive resin composition, dry film, and printed wiring board having photo-cured product of photosensitive resin composition |
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| Country | Link |
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| JP (1) | JP6986534B2 (en) |
| KR (1) | KR20210031374A (en) |
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| TW (1) | TW202121055A (en) |
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| Publication number | Publication date |
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| KR20210031374A (en) | 2021-03-19 |
| TW202121055A (en) | 2021-06-01 |
| JP6986534B2 (en) | 2021-12-22 |
| JP2021043335A (en) | 2021-03-18 |
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