WO2022113829A1 - Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for manufacturing printed circuit board - Google Patents
Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for manufacturing printed circuit board Download PDFInfo
- Publication number
- WO2022113829A1 WO2022113829A1 PCT/JP2021/042092 JP2021042092W WO2022113829A1 WO 2022113829 A1 WO2022113829 A1 WO 2022113829A1 JP 2021042092 W JP2021042092 W JP 2021042092W WO 2022113829 A1 WO2022113829 A1 WO 2022113829A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- meth
- photosensitive resin
- photosensitive
- acrylate
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims description 60
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 37
- 239000011230 binding agent Substances 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003999 initiator Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 6
- 150000003440 styrenes Chemical class 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims description 48
- -1 acrylate compound Chemical class 0.000 claims description 29
- 239000004020 conductor Substances 0.000 claims description 23
- 238000005530 etching Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000007747 plating Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 7
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 229930185605 Bisphenol Natural products 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 77
- 239000000243 solution Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000011241 protective layer Substances 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000011161 development Methods 0.000 description 12
- 230000018109 developmental process Effects 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011247 coating layer Substances 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000003673 urethanes Chemical class 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 3
- 206010034960 Photophobia Diseases 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 238000002788 crimping Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 208000013469 light sensitivity Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 150000003219 pyrazolines Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000004804 winding Methods 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- UKQBWWAPJNHIQR-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.CCC(CO)(CO)CO UKQBWWAPJNHIQR-UHFFFAOYSA-N 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KSMGAOMUPSQGTB-UHFFFAOYSA-N 9,10-dibutoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=C(OCCCC)C2=C1 KSMGAOMUPSQGTB-UHFFFAOYSA-N 0.000 description 2
- MTRFEWTWIPAXLG-UHFFFAOYSA-N 9-phenylacridine Chemical class C1=CC=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 MTRFEWTWIPAXLG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical class [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
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- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
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- 239000012760 heat stabilizer Substances 0.000 description 2
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- 239000003112 inhibitor Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- 238000004448 titration Methods 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
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- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-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
- 150000003918 triazines Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
-
- 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
- H05K3/18—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 precipitation techniques to apply the conductive material
Definitions
- the present disclosure relates to a photosensitive resin composition, a photosensitive element, a method for forming a resist pattern, and a method for manufacturing a printed wiring board.
- a photosensitive resin composition is used as a resist material used for an etching treatment or a plating treatment, and a layer formed on a support film using the photosensitive resin composition (hereinafter, “photosensitive”).
- Photosensitive elements with also referred to as "layers" are widely used.
- the printed wiring board is manufactured by the following procedure, for example, using the above-mentioned photosensitive element. That is, first, the photosensitive layer of the photosensitive element is laminated on a circuit-forming substrate such as a copper-clad laminate. Next, the photosensitive layer is exposed via a mask film or the like to form a photocurable portion. At this time, the support film is peeled off before or after the exposure. Then, the region other than the light-cured portion of the photosensitive layer is removed with a developing solution to form a resist pattern. Next, using the resist pattern as a resist, an etching treatment or a plating treatment is performed to form a conductor pattern, and finally the photocured portion (resist pattern) of the photosensitive layer is peeled off (removed).
- the photosensitive layer is required to have excellent characteristics in the etching treatment or the plating treatment, excellent adhesion to the circuit forming substrate, and excellent resolution in forming the resist pattern.
- Patent Document 1 discloses a photosensitive resin composition having excellent sensitivity and resolution by using a specific sensitizing dye.
- Patent Document 2 discloses a photosensitive resin composition having excellent sensitivity and resolution by using a specific alkali-soluble polymer and a compound having an ethylenic double bond.
- the photosensitive layer When laminating the photosensitive layer of the photosensitive element on the circuit forming substrate, if the photosensitive layer has low followability to the circuit forming substrate, a fine void is generated between the photosensitive layer and the circuit forming substrate. , May affect the formation of conductor patterns. Therefore, the photosensitive layer is required to have excellent followability to the circuit forming substrate.
- the present disclosure discloses a photosensitive resin composition capable of forming a photosensitive layer having excellent followability to a circuit forming substrate, a photosensitive element using the photosensitive resin composition, a method for forming a resist pattern, and a printed wiring board. It is an object of the present invention to provide the manufacturing method of.
- the photosensitive resin composition according to the present disclosure contains a binder polymer, a photopolymerizable compound, and a photopolymerization initiator, and the binder polymer is a structural unit derived from a polymerizable monomer having a carboxy group (a structural unit ().
- A1 a structural unit (a2) derived from styrene or a styrene derivative, a structural unit (a3) derived from an alkyl (meth) acrylic rate having an alkyl group having 1 to 3 carbon atoms, and 4 to 4 carbon atoms. It has a structural unit (a4) derived from an alkyl (meth) methacrylate having 12 alkyl groups.
- the photosensitive element according to the present disclosure includes a support and a photosensitive layer formed on the support, and the photosensitive layer contains the above-mentioned photosensitive resin composition.
- the method for forming a resist pattern according to the present disclosure includes a step of forming a photosensitive layer on a substrate by using the above-mentioned photosensitive resin composition or a photosensitive element, and irradiation of at least a part of the photosensitive layer with active light.
- the process includes a step of forming a photo-cured portion and a step of removing at least a part of the unphoto-cured portion of the photosensitive layer from the substrate.
- the method for manufacturing a printed wiring board according to the present disclosure includes a step of forming a conductor pattern by etching or plating a substrate on which a resist pattern is formed by the method for forming a resist pattern.
- a photosensitive resin composition capable of forming a photosensitive layer having excellent followability to a circuit forming substrate, a photosensitive element using the photosensitive resin composition, a method for forming a resist pattern, and printing.
- a method for manufacturing a wiring board can be provided.
- the term "process” is included in this term not only as an independent process but also as long as the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. Is done.
- the term "layer” includes not only a structure having a shape formed on the entire surface but also a structure having a shape partially formed when observed as a plan view.
- the numerical range indicated by using "-" indicates a range including the numerical values before and after "-" as the minimum value and the maximum value, respectively.
- the upper limit value or the lower limit value of the numerical range of one step may be replaced with the upper limit value or the lower limit value of the numerical range of another step.
- the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
- (meth) acrylic acid means at least one of “acrylic acid” and the corresponding “methacrylic acid”, and the same applies to other similar expressions such as (meth) acrylate.
- the “solid content” is a non-volatile substance excluding volatile substances such as water and solvent contained in the photosensitive resin composition, and is volatile when the resin composition is dried. It shows the components that remain without being used, and also contains liquid, water candy-like, and wax-like components at room temperature around 25 ° C.
- the photosensitive resin composition according to the present embodiment contains a binder polymer, a photopolymerizable compound, and a photopolymerization initiator, and the binder polymer is a structural unit derived from a polymerizable monomer having a carboxy group.
- A1 a structural unit (a2) derived from styrene or a styrene derivative, a structural unit (a3) derived from an alkyl (meth) acrylic rate having an alkyl group having 1 to 3 carbon atoms, and 4 carbon atoms. It has a structural unit (a4) derived from an alkyl (meth) methacrylate having up to 12 alkyl groups.
- the component (A) component includes a structural unit (a1) having a carboxy group, a structural unit (a2) derived from styrene or a styrene derivative, and an alkyl (meth) having an alkyl group having 1 to 3 carbon atoms.
- the binder polymer has a structural unit (a1) from the viewpoint of alkali developability.
- the polymerizable monomer having a carboxy group include (meth) acrylic acid, ⁇ -bromoacrylic acid, ⁇ -chloroacrylic acid, ⁇ -furyl (meth) acrylic acid, ⁇ -styryl (meth) acrylic acid, and the like.
- Maleic acid monoesters such as maleic acid, maleic acid anhydride, monomethyl maleate, monoethyl maleate, monoisopropyl maleate, fumaric acid, silicic acid, ⁇ -cyanosilicic acid, itaconic acid, crotonic acid, and propioleic acid Can be mentioned.
- the polymerizable monomer having a carboxy group may be (meth) acrylic acid or methacrylic acid from the viewpoint of further improving the alkali developability.
- the content of the structural unit (a1) is 10 to 30% by mass, 15 to 28% by mass, or 20 based on the total amount of the component (A) from the viewpoint of improving the alkali developability and the followability in a well-balanced manner. It may be up to 26% by mass.
- the content of the structural unit (a1) is 10% by mass or more, the alkali developability tends to be improved, and when the content is 30% by mass or less, the followability tends to be excellent.
- the binder polymer has a structural unit (a2) from the viewpoint of resolution.
- the styrene derivative is a polymerizable compound in which a hydrogen atom in the ⁇ -position or aromatic ring of styrene such as vinyltoluene and ⁇ -methylstyrene is substituted.
- the content of the structural unit (a2) in the component (A) is 10 to 50% by mass and 12 to 45 based on the total amount of the component (A). It may be% by mass, or 14 to 44% by mass.
- the binder polymer has a structural unit (a3) from the viewpoint of resolution.
- alkyl (meth) acrylic rate having an alkyl group having 1 to 3 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, and propyl (meth) acrylate.
- the content of the structural unit (a3) in the component (A) is 5 to 70% by mass and 12 to 65 based on the total amount of the component (A) from the viewpoint of improving the alkali developability and the followability in a well-balanced manner. It may be% by mass, or 15 to 64% by mass.
- the content of the structural unit (a3) is 5% by mass or more, the alkali developability tends to be improved, and when the content is 70% by mass or less, the followability tends to be excellent.
- the binder polymer has a structural unit (a4) from the viewpoint of followability.
- the alkyl group having 4 to 12 carbon atoms may be a linear or branched alkyl group.
- Examples of the alkyl (meth) methacrylate having an alkyl group having 4 to 12 carbon atoms include butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, and octyl (meth) acrylate.
- 2-Ethylhexyl (meth) acrylate nonyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, and dodecyl (meth) acrylate.
- the content of the structural unit (a4) in the component (A) is 0.5 to 30% by mass, 0, based on the total amount of the component (A). It may be 8 to 25% by mass, or 1 to 22% by mass.
- the component (A) may further have a structural unit (a5) other than the structural units (a1) to (a4).
- a structural unit (a5) examples include benzyl (meth) acrylate or a derivative thereof, acrylamide such as diacetoneacrylamide, and an ether compound of vinyl alcohol such as vinyl-n-butyl ether.
- the acid value of the component (A) is 100 mgKOH / g or more, 110 mgKOH / g or more, 120 mgKOH / g or more, or 130 mgKOH / g or more from the viewpoint of further improving the balance between developability, resolution and followability. May be good.
- the acid value of the component (A) may be 180 mgKOH / g or less, 170 mgKOH / g or less, 165 mgKOH / g or less, or 160 mgKOH / g or less from the viewpoint of further improving the followability of the photosensitive layer.
- the acid value of the binder polymer may be 100 mgKOH / g or more and 180 mgKOH / g or less, 110 mgKOH / g or more and 170 mgKOH / g or less, 120 mgKOH / g or more and 165 mgKOH / g or less, or 130 mgKOH / g or more and 160 mgKOH / g or less.
- the weight average molecular weight (Mw) of the component (A) may be 60,000 or less, 56,000 or less, 54,000 or less, or 52,000 or less in terms of further excellent developability.
- the Mw of the component (A) may be 10,000 or more, 15,000 or more, 20,000 or more, or 25,000 or more in terms of further excellent adhesion.
- the weight average molecular weight of the binder polymer may be 10,000 or more and 60,000 or less, 15,000 or more and 56,000 or less, 20,000 or more and 54,000 or less, or 25,000 or more and 52,000 or less.
- the degree of dispersion (weight average molecular weight / number average molecular weight) of the component (A) may be 3.0 or less, 2.8 or less, or 2.5 or less in terms of further excellent resolution and adhesion.
- the resolution tends to improve as the degree of dispersion decreases.
- the weight average molecular weight and the number average molecular weight are measured by gel permeation chromatography (GPC) and are converted values using standard polystyrene as a standard sample.
- the glass transition temperature (Tg) of the component (A) may be 80 to 130 ° C., 85 to 125 ° C., or 90 to 120 ° C. from the viewpoint of further improving the followability.
- the component (A) one type can be used alone or two or more types can be used in combination.
- the component (A) includes, for example, two or more kinds of binder polymers composed of different polymerizable monomers, two or more kinds of binder polymers having different Mw, and different dispersities. Two or more kinds of binder polymers can be mentioned.
- the content of the component (A) is 30 to 80 parts by mass, 40 to 75 parts by mass, 50 to 70 parts by mass, or 50 to 60 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B). It may be a department. When the content of the component (A) is within this range, the strength of the light-cured portion of the photosensitive layer becomes better.
- Component (B) photopolymerizable compound
- the component (B) is not particularly limited as long as it has at least one ethylenically unsaturated bond and is photopolymerizable.
- the ethylenically unsaturated bond is not particularly limited as long as photopolymerization is possible. Examples of the ethylenically unsaturated bond include ⁇ , ⁇ -unsaturated carbonyl groups such as (meth) acryloyl group.
- Examples of the photopolymerizable compound having an ⁇ , ⁇ -unsaturated carbonyl group include ⁇ , ⁇ -unsaturated carboxylic acid ester of a polyhydric alcohol, bisphenol type (meth) acrylate, and ⁇ , ⁇ -unmodified of a glycidyl group-containing compound.
- Examples include saturated carboxylic acid adducts, (meth) acrylates with urethane bonds, nonylphenoxypolyethyleneoxyacrylates, and (meth) acrylic acid alkyl esters.
- Examples of the ⁇ , ⁇ -unsaturated carboxylic acid ester of the polyhydric alcohol include polyethylene glycol di (meth) acrylate having an ethylene group number of 2 to 14, and polypropylene glycol di (meth) acrylate having a propylene group number of 2 to 14. Meta) acrylate, polyethylene / polypropylene glycol di (meth) acrylate, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) having 2 to 14 ethylene groups and 2 to 14 propylene groups.
- EO modification means having a block structure of ethylene oxide (EO) group
- PO modification means having a block structure of propylene oxide (PO) group.
- the component (B) may contain a polyalkylene glycol di (meth) acrylate from the viewpoint of improving the flexibility of the resist pattern.
- the polyalkylene glycol di (meth) acrylate may have at least one of an EO group and a PO group, and may have both an EO group and a PO group.
- the EO group and the PO group may be continuously present in a block or randomly.
- the PO group may be either an oxy-n-propylene group or an oxyisopropylene group.
- the secondary carbon of the propylene group may be bonded to the oxygen atom, or the primary carbon may be bonded to the oxygen atom.
- polyalkylene glycol di (meth) acrylate examples include, for example, FA-023M (manufactured by Showa Denko Materials Co., Ltd.), FA-024M (manufactured by Showa Denko Materials Co., Ltd.), and NK Ester HEMA-9P (new). Nakamura Chemical Industry Co., Ltd.).
- the component (B) may contain (meth) acrylate having a urethane bond from the viewpoint of improving the flexibility of the resist pattern.
- the (meth) acrylate having a urethane bond include a (meth) acrylic monomer having an OH group at the ⁇ -position and a diisocyanate (isophorone diisocyanate, 2,6-toluene diisocyanate, 2,4-toluene diisocyanate, 1,6-hexa).
- Examples thereof include addition reactants with methylene diisocyanate), tris ((meth) acryloxytetraethylene glycol isocyanate) hexamethylene isocyanurate, EO-modified urethane di (meth) acrylate, and EO and PO-modified urethane di (meth) acrylate.
- Examples of commercially available products of EO-modified urethane di (meth) acrylate include “UA-11” and “UA-21EB” (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.).
- Examples of commercially available products of EO and PO-modified urethane di (meth) acrylate include “UA-13” (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.).
- the component (B) may contain dipentaerythritol or a (meth) acrylate compound having a skeleton derived from pentaerythritol from the viewpoint of easily forming a thick-film resist pattern and improving resolution and adhesion in a well-balanced manner.
- the (meth) acrylate compound having a skeleton derived from dipentaerythritol or pentaerythritol preferably has four or more (meth) acryloyl groups, and is preferably dipentaerythritol penta (meth) acrylate or dipentaerythritol hexa (meth) acrylate. May be.
- the component (B) may contain a bisphenol type (meth) acrylate, or may contain a bisphenol A type (meth) acrylate among the bisphenol type (meth) acrylates. ..
- the bisphenol A type (meth) acrylate include 2,2-bis (4-((meth) acryloxypolyethoxy) phenyl) propane and 2,2-bis (4-((meth) acryloxypolypropoxy)).
- 2,2-bis (4-((meth) acryloxipolyethoxy) phenyl) propane is preferable from the viewpoint of further improving the resolution and putter forming property.
- nonylphenoxypolyethyleneoxyacrylate examples include nonylphenoxytetraethyleneoxyacrylate, nonylphenoxypentaethyleneoxyacrylate, nonylphenoxyhexaethyleneoxyacrylate, nonylphenoxyheptaethyleneoxyacrylate, nonylphenoxyoctaethyleneoxyacrylate, and nonylphenoxynonaethyleneoxy.
- examples thereof include acrylate, nonylphenoxydecaethyleneoxyacrylate, and nonylphenoxyundecaethyleneoxyacrylate.
- the content of the component (B) is preferably 20 to 60 parts by mass, more preferably 30 to 55 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B). It is more preferably 35 to 50 parts by mass.
- the content of the component (B) is in this range, the light sensitivity and the coating film property become better in addition to the resolution and adhesion of the photosensitive resin composition and the resist hem generation property.
- the component (C) is not particularly limited as long as it can polymerize the component (B), and can be appropriately selected from commonly used photopolymerization initiators. From the viewpoint of improving pattern formation, those that generate free radicals by active light, for example, acylphosphine oxide type, oxime ester type, aromatic ketone type, quinone type, alkylphenone type, imidazole type, aclysine type, phenylglycine. Examples thereof include photopolymerization initiators such as radicals and quinones.
- the component (C) may contain an acridine-based photopolymerization initiator, a phenylglycine-based photopolymerization initiator, or an imidazole-based photopolymerization initiator in terms of improving sensitivity and resolution in a well-balanced manner, and may contain an acridine-based photopolymerization initiator. Is preferably included.
- the component (C) one type can be used alone or two or more types can be used in combination.
- acridin-based photopolymerization initiator examples include 9-phenylacridines, 9- (p-methylphenyl) acridins, 9- (m-methylphenyl) acridins, 9- (p-chlorophenyl) acridins, and 9- (m-).
- Chlorophenyl) acridines 9-aminoacridines, 9-dimethylaminoacridines, 9-diethylaminoacridines, 9-pentylaminoacridines, 1,2-bis (9-acridinyl) ethane, 1,4-bis (9-acridinyl) butane, 1,6-bis (9-acridinyl) hexane, 1,8-bis (9-acridinyl) octane, 1,10-bis (9-acridinyl) decane, 1,12-bis (9-acridinyl) dodecane, 1, Bis (9) such as 14-bis (9-acridinyl) tetradecane, 1,16-bis (9-acridinyl) hexadecane, 1,18-bis (9-acridinyl) octadecane, 1,20-bis (9-acridinyl) icosane, etc.
- phenylglycine-based photopolymerization initiator examples include N-phenylglycine, N-methyl-N-phenylglycine, and N-ethyl-N-phenylglycine.
- imidazole-based photopolymerization initiator examples include 2- (o-chlorophenyl) -4,5-diphenylbiimidazole, 2,2', 5-tris- (o-chlorophenyl) -4- (3,4-dimethoxy).
- the content of the component (C) is 0.1 to 10 parts by mass, 0.2 to 5 parts by mass, and 0.4 to 3 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B). , Or 0.5 to 2 parts by mass.
- the content of the component (C) is 0.1 parts by mass or more, the light sensitivity, resolution and adhesion tend to be improved, and when the content is 10 parts by mass or less, the resist pattern forming property tends to be better.
- the photosensitive resin composition according to the present embodiment may further contain a sensitizer having absorption at 340 to 430 nm as the component (D).
- a sensitizer having absorption at 340 to 430 nm as the component (D).
- the sensitizer include dialkylaminobenzophenone compounds, pyrazoline compounds, anthracene compounds, coumarin compounds, xanthone compounds, oxazole compounds, benzoxazole compounds, thiazole compounds, benzothiazole compounds, triazole compounds, stylben compounds, triazine compounds and thiophene compounds. , Naphthalimide compounds, and triarylamine compounds.
- the sensitizer may contain at least one selected from the group consisting of pyrazoline compounds, anthracene compounds, coumarin compounds, and triarylamine compounds from the viewpoint of sensitivity and adhesion, and may contain pyrazoline compounds, anthracene compounds, and coumarin compounds. It may contain at least one selected from the group consisting of.
- Examples of the pyrazoline compound include 1-phenyl-3- (4-methoxystyryl) -5- (4-methoxyphenyl) pyrazoline and 1-phenyl-3- (4-tert-butylstyryl) -5- (4-). Examples thereof include tert-butylphenyl) pyrazoline and 1-phenyl-3-biphenyl-5- (4-tert-butylphenyl) pyrazoline.
- Examples of the anthracene compound include 9,10-dibutoxyanthracene and 9,10-diphenylanthracene.
- Examples of the coumarin compound include 3-benzoyl-7-diethylaminocoumarin, 7-diethylamino-4-methylcoumarin, 3,3'-carbonylbis (7-diethylaminocoumarin), and 2,3,6,7-tetrahydro-. Examples thereof include 9-methyl-1H, 5H, 11H- [1] benzopyrano [6,7,8-ij] kilolysine-11-one.
- the content of the component (D) is 0.01 to 10% by mass and 0.05 to 5 based on the total solid content of the photosensitive resin composition. It may be% by mass, or 0.1 to 3% by mass.
- the content of the component (D) is 0.01% by mass or more, the sensitivity and resolution are further improved, and when it is 10% by mass or less, the resist shape is suppressed from becoming an inverted trapezoid and adhered. The sex is improved.
- the content of the component (D) is 0.005 to 0.5 parts by mass, 0.008 with respect to 100 parts by mass of the total amount of the components (A) and (B). It may be up to 0.2 parts by mass or 0.01 to 0.1 parts by mass.
- the photosensitive resin composition according to the present embodiment may further contain a heat stabilizer as the component (E).
- a heat stabilizer as the component (E).
- the component (E) include quinone derivatives such as benzoquinone and hydroquinone, phenol derivatives such as 4-methoxyphenol and 4-t-butylcatechol (hindered phenol derivatives), and 2,2,6,6-tetramethylpiperidine.
- examples thereof include aminoxyl derivatives such as -1-oxyl and 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, and hindered amine derivatives such as tetramethylpiperidylmethacrylate.
- the aminoxyl derivative as the component (E)
- the content of the component (E) may be 0.005 to 10 parts by mass, 0.01 to 8 parts by mass, or 0.01 to 5 parts by mass with respect to 100 parts by mass of the total amount of the component (A). ..
- the content of the component (E) is 0.005 to 20 parts by mass, 0.01 to 5 parts by mass, or 0.02 to 1 part by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B). It may be a department. When this content is 0.005 part by mass or more, the resolution and the suppressibility of the resist hem generation amount tend to be more excellent, and when it is 20 parts by mass or less, the sensitivity tends to be more excellent.
- the photosensitive resin composition according to the present embodiment contains, if necessary, a dye, a photocoloring agent, a heat coloring inhibitor, a plasticizer, a pigment, a filler, a defoaming agent, a flame retardant, an adhesion imparting agent, and leveling.
- Additives such as agents, peeling accelerators, antioxidants, fragrances, imaging agents, thermal cross-linking agents, and polymerization inhibitors may be further contained. These additives may be used alone or in combination of two or more.
- Examples of the dye include malachite green, Victoria pure blue, brilliant green, and methyl violet.
- Examples of the photocoloring agent include tribromophenyl sulfone, leuco crystal violet, diphenylamine, benzylamine, triphenylamine, diethylaniline, and o-chloroaniline.
- Examples of the plasticizer include p-toluenesulfonamide.
- the content of the additive is 0.01 to 10 parts by mass, 0.05 to 5 parts by mass, or 0.1 to 3 parts by mass, respectively, with respect to 100 parts by mass of the total amount of the component (A) and the component (B). There may be.
- the photosensitive resin composition is dissolved in a solvent such as methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N, N-dimethylformamide, propylene glycol monomethyl ether, or a mixed solvent thereof, if necessary. Therefore, it can be prepared as a solution having a solid content of about 30 to 60% by mass.
- a solvent such as methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N, N-dimethylformamide, propylene glycol monomethyl ether, or a mixed solvent thereof, if necessary. Therefore, it can be prepared as a solution having a solid content of about 30 to 60% by mass.
- the photosensitive element of the present embodiment includes a support and a photosensitive layer formed on the support, and the photosensitive layer includes the above-mentioned photosensitive resin composition.
- the photosensitive layer may be laminated on the substrate and then exposed without peeling the support (support film).
- the photosensitive element 1 according to the present embodiment has a support 2 and a photosensitive layer 3 derived from the photosensitive resin composition formed on the support 2, as shown in FIG. 1 as a schematic cross-sectional view of an example thereof. And other layers such as the protective layer 4 provided as needed.
- polyester films such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene-2,6-naphthalate (PEN), and polyolefin films such as polypropylene and polyethylene.
- PET film may be used because it is easily available and has excellent handleability (particularly, heat resistance, heat shrinkage rate, breaking strength) in the manufacturing process.
- the haze of the support may be 0.01-1.0% or 0.01-0.5%. When the haze is 0.01% or more, the support itself tends to be easy to manufacture, and when it is 1.0% or less, there is a tendency to reduce the minute defects that may occur in the resist pattern. "Haze” means cloudiness.
- the haze in the present disclosure refers to a value measured using a commercially available turbidity meter (turbidity meter) in accordance with the method specified in JIS K7105. The haze can be measured with a commercially available turbidity meter such as NDH-5000 (manufactured by Nippon Denshoku Industries Co., Ltd.).
- the thickness of the support may be 1 to 100 ⁇ m, 5 to 60 ⁇ m, 10 to 50 ⁇ m, 10 to 40 ⁇ m, 10 to 30 ⁇ m, or 10 to 25 ⁇ m.
- the thickness of the support is 1 ⁇ m or more, it tends to be possible to prevent the support from being torn when the support is peeled off. Further, when the thickness of the support is 100 ⁇ m or less, it is possible to suppress a decrease in resolution when exposure is performed through the support.
- the photosensitive element may be further provided with a protective layer, if necessary.
- a protective layer a film may be used in which the adhesive force between the photosensitive layer and the protective layer is smaller than the adhesive force between the photosensitive layer and the support, and a low fisheye film may be used. You may use it.
- a film that can be used as the above-mentioned support can be mentioned.
- a polyethylene film may be used as the protective layer.
- the thickness of the protective layer varies depending on the application, but may be about 1 to 100 ⁇ m.
- the photosensitive element can be manufactured, for example, as follows. That is, a solution (coating liquid) of the photosensitive resin composition is applied onto the support to form a coating layer, and the coating layer is formed by drying the solution. Next, by covering the surface of the photosensitive layer opposite to the support with a protective layer, the support, the photosensitive layer formed on the support, and the protective layer laminated on the photosensitive layer are provided. A photosensitive element is obtained.
- the coating liquid can be applied onto the support by a known method such as roll coating, comma coating, gravure coating, air knife coating, die coating, bar coating and the like.
- Drying of the coating layer is not particularly limited as long as at least a part of the organic solvent can be removed from the coating layer. For example, it may be carried out at 70 to 150 ° C. for about 5 to 30 minutes. After drying, the amount of residual solvent in the photosensitive layer may be 2% by mass or less from the viewpoint of preventing the diffusion of the solvent in a later step.
- the thickness of the photosensitive layer in the photosensitive element can be appropriately selected depending on the intended use, but the thickness after drying may be 1 to 100 ⁇ m, 1 to 50 ⁇ m, or 5 to 40 ⁇ m. When the thickness is 1 ⁇ m or more, industrial coating is facilitated and productivity is improved. Further, when the thickness is 100 ⁇ m or less, the adhesion and the resolution are improved.
- the form of the photosensitive element is not particularly limited.
- it may be in the form of a sheet, or may be in the form of a roll wound around a winding core.
- the support film When winding in a roll shape, the support film may be wound so as to be on the outside.
- the winding core include plastics such as polyethylene resin, polypropylene resin, polystyrene resin, polyvinyl chloride resin, and ABS resin (acrylonitrile-butadiene-styrene copolymer).
- An end face separator may be installed on the end face of the roll-shaped photosensitive element from the viewpoint of end face protection, or a moisture-proof end face separator may be installed from the viewpoint of edge fusion resistance.
- the photosensitive element may be wrapped in a black sheet having low moisture permeability and packaged.
- the photosensitive element can be suitably used, for example, in a method for forming a resist pattern, which will be described later. Above all, from the viewpoint of resolution, it is suitable for application to a manufacturing method for forming a conductor pattern by an etching process.
- the method for forming the resist pattern of the present embodiment is as follows: (i) a step of forming a photosensitive layer on a substrate by using the photosensitive resin composition or the photosensitive element (photosensitive layer forming step). ii) A step (exposure step) of irradiating at least a part (predetermined part) of the photosensitive layer with active light to form a photocurable portion, and (iii) at least a part of the unphotocured portion from the substrate. It may be configured to include a step (development step) for removing the above-mentioned light, and if necessary, other steps.
- the resist pattern can be said to be a photocured product pattern of the photosensitive resin composition, and can also be said to be a relief pattern.
- the method for forming a resist pattern can also be said to be a method for manufacturing a substrate with a resist pattern.
- the photosensitive resin composition may be applied and dried, or after the protective layer is removed from the photosensitive element, the photosensitive layer of the photosensitive element is formed. It may be crimped to the above substrate while heating.
- a photosensitive element it is composed of a substrate, a photosensitive layer, and a support, and a laminated body in which these are laminated in order can be obtained.
- the substrate is not particularly limited, but usually, a circuit forming substrate provided with an insulating layer and a conductor layer formed on the insulating layer, or a die pad (lead frame substrate) such as an alloy substrate is used.
- the photosensitive layer forming step is preferably performed under reduced pressure from the viewpoint of adhesion and followability.
- the photosensitive layer and / or the substrate may be heated at a temperature of 70 to 130 ° C. during crimping.
- the crimping may be performed at a pressure of about 0.1 to 1.0 MPa (about 1 to 10 kgf / cm 2 ), but these conditions are appropriately selected as necessary. If the photosensitive layer is heated to 70 to 130 ° C., it is not necessary to preheat the substrate in advance, but the substrate can be preheated in order to further improve the adhesion and the followability.
- (Ii) exposure step In the exposure step, by irradiating at least a part of the photosensitive layer formed on the substrate with the active light beam, the portion irradiated with the active light ray is photocured to form a latent image.
- the active light can be irradiated through the support if the support is transparent to the active light, but if the support is light-shielding. Irradiates the photosensitive layer with active light rays after removing the support.
- Examples of the exposure method include a method of irradiating an image with active light rays via a negative or positive mask pattern called artwork (mask exposure method). Further, a method of irradiating an active ray in an image shape by a projection exposure method may be adopted. Further, a method of irradiating an active ray in an image shape by a direct drawing exposure method such as an LDI (Laser Direct Imaging) exposure method or a DLP (Digital Light Processing) exposure method may be adopted.
- LDI Laser Direct Imaging
- DLP Digital Light Processing
- a known light source can be used, and for example, a carbon arc lamp, a mercury steam arc lamp, a high-pressure mercury lamp, a xenon lamp, a gas laser such as an argon laser, a solid-state laser such as a YAG laser, a semiconductor laser and the like can be used. Those that effectively radiate ultraviolet rays and visible light are used.
- a resist pattern is formed on the substrate by removing at least a part of the unphotocured portion (other than the photocured portion) of the photosensitive layer from the substrate.
- a support is present on the photosensitive layer, the support is removed, and then the region other than the photocured portion (which can be said to be an unexposed portion) is removed (developed).
- development methods wet development and dry development, and wet development is widely used.
- developer in the case of wet development, develop by a known development method using a developer corresponding to the photosensitive resin composition.
- the developing method include a dip method, a paddle method, a spray method, brushing, slapping, scraping, rocking immersion and the like.
- a high pressure spray method may be used as the developing method. Development may be performed by combining these two or more methods.
- the composition of the developer is appropriately selected according to the composition of the photosensitive resin composition.
- the developing solution include an alkaline aqueous solution and an organic solvent developing solution.
- an alkaline aqueous solution may be used as the developer.
- the base of the alkaline aqueous solution include alkali hydroxides such as hydroxides of lithium, sodium or potassium; alkali carbonates such as carbonates or bicarbonates of lithium, sodium, potassium or ammonium; potassium phosphate, sodium phosphate and the like.
- Alkaline metal phosphates Alkaline metal phosphates; Alkaline metal pyrophosphates such as sodium pyrophosphate and potassium pyrophosphate; borosand, sodium metasilicate, tetramethylammonium hydroxide, ethanolamine, ethylenediamine, diethylenetriamine, 2-amino-2-hydroxymethyl- 1,3-Propanediol, 1,3-diaminopropanol-2, morpholine and the like are used.
- the alkaline aqueous solution used for development includes a dilute solution of 0.1 to 5% by mass of sodium carbonate, a dilute solution of 0.1 to 5% by mass of potassium carbonate, a dilute solution of 0.1 to 5% by mass of sodium hydroxide, and 0.
- a dilute solution of 1 to 5 mass% sodium tetraborate or the like can be used.
- the pH of the alkaline aqueous solution may be in the range of 9 to 11, and the temperature can be adjusted according to the alkaline developability of the photosensitive layer.
- a surface active agent, a defoaming agent, a small amount of an organic solvent for accelerating development, or the like may be mixed in the alkaline aqueous solution.
- Examples of the organic solvent used in the alkaline aqueous solution include acetone, ethyl acetate, alkoxyethanol having an alkoxy group having 1 to 4 carbon atoms, ethyl alcohol, isopropyl alcohol, butyl alcohol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol. Examples include monobutyl ether.
- organic solvent used in the organic solvent developer examples include 1,1,1-trichloroethane, N-methyl-2-pyrrolidone, N, N-dimethylformamide, cyclohexanone, methyl isobutyl ketone, and ⁇ -butyrolactone. ..
- water may be added to these organic solvents so as to be in the range of 1 to 20% by mass to prepare an organic solvent developer.
- heating at about 60 to 250 ° C. or exposure of about 0.2 to 10 J / cm 2 is performed as necessary. May include a step of further curing the resist pattern.
- the method for manufacturing a printed wiring board of the present embodiment includes a step of etching or plating a substrate on which a resist pattern is formed by the method for forming a resist pattern to form a conductor pattern, and if necessary, a resist. It may be configured to include other steps such as a pattern removing step.
- the conductor layer provided on the substrate is plated using the resist pattern formed on the substrate as a mask.
- the resist may be removed by removing the resist pattern described later, and the conductor layer covered with the resist may be further etched to form the conductor pattern.
- the method of the plating treatment may be an electrolytic plating treatment, an electroless plating treatment, or an electroless plating treatment.
- the conductor layer provided on the substrate is removed by etching using the resist pattern formed on the substrate as a mask to form the conductor pattern.
- the etching treatment method is appropriately selected according to the conductor layer to be removed.
- the etching solution include a cupric chloride solution, a ferric chloride solution, an alkaline etching solution, and a hydrogen peroxide-based etching solution.
- the resist pattern on the substrate may be removed after the etching treatment or the plating treatment.
- the resist pattern can be removed, for example, with a stronger alkaline aqueous solution than the alkaline aqueous solution used in the development step.
- a stronger alkaline aqueous solution for example, a 1 to 10% by mass sodium hydroxide aqueous solution, a 1 to 10% by mass potassium hydroxide aqueous solution, or the like is used.
- the desired printed wiring board can be manufactured by further etching the conductor layer covered with the resist by the etching treatment to form the conductor pattern.
- the etching treatment method at this time is appropriately selected according to the conductor layer to be removed. For example, the above-mentioned etching solution can be applied.
- FIG. 2 shows an example of the manufacturing process of the printed wiring board by the subtractive method.
- a substrate circuit forming substrate
- the conductor layer 40 is, for example, a copper layer.
- the photosensitive layer 30 is formed on the conductor layer 40 by the photosensitive layer forming step.
- the photosensitive layer 30 is directly irradiated with active light rays by a drawing method to form a photocurable portion on the photosensitive layer 30.
- the resist pattern 32 which is a photocurable portion, is formed on the substrate by removing the region other than the photocurable portion formed by the exposure step from the substrate by the developing step.
- the conductor layer 40 not covered with the resist pattern 32 is removed by an etching process to form the conductor pattern 42.
- the resist pattern 32 is peeled off with an aqueous solution of a strong alkali to prepare a substrate having the conductor pattern 42.
- the method for manufacturing a printed wiring board according to the present embodiment can be applied not only to the manufacture of a single-layer printed wiring board but also to the manufacture of a multilayer printed wiring board, and also to the manufacture of a printed wiring board having a small-diameter through hole. It is possible.
- Binder polymer Methacrylic acid (MAA), styrene (ST), methyl methacrylate (MMA), butyl methacrylate (BMA), butyl acrylate (BA), as polymerizable monomers for synthesizing the binder polymers used in Examples and Comparative Examples.
- MAA Methacrylic acid
- ST styrene
- MMA methyl methacrylate
- BMA butyl methacrylate
- BA butyl acrylate
- AEEC ethyl acrylate
- BZMA benzyl methacrylate
- the above solution a was added dropwise to the mixed solution in the flask over 4 hours, and then the mixture was stirred at 80 ° C. for 2 hours. Then, the above solution b was added dropwise to the solution in the flask, and the mixture was stirred at 80 ° C. for 2 hours. Further, the solution in the flask was heated to 95 ° C. over 1 hour while stirring was continued, and then the solution c was added dropwise over 10 minutes and stirred at 95 ° C. for 2 hours to carry out the reaction. After cooling the reaction solution to 50 ° C., methanol was added to obtain a solution of the binder polymer (A-1). The non-volatile content (solid content) of the binder polymer (A-1) was 47.7% by mass.
- Binder Polymers (A-2) to (A-18) The binder polymer (A-2) was obtained in the same manner as in obtaining the solution of the binder polymer (A-1), except that the polymerizable monomer was used in the mass ratio shown in Table 1 or Table 2. )-(A-18) was obtained.
- Weight average molecular weight 120 mg of the binder polymer solution was collected and dissolved in 5 mL of tetrahydrofuran to prepare a sample for Mw measurement. Mw was measured by gel permeation chromatography (GPC) and derived by conversion using a standard polystyrene calibration curve. The conditions of GPC are shown below.
- Glass-transition temperature The glass transition temperature (Tg) of the binder polymer was calculated from the Fox formula.
- Photosensitive resin composition The components (A), (B) and (C) of the blending amount (parts by mass) shown in Table 3 or Table 4 are mixed with 5 parts by mass of methanol, 10 parts by mass of toluene and 11 parts by mass of acetone as solvents. As a result, the photosensitive resin compositions of Examples and Comparative Examples were prepared, respectively.
- the blending amount of the binder polymer shown in Tables 3 and 4 is the mass of the non-volatile component (solid content amount).
- a solution of the photosensitive resin composition is applied onto a polyethylene terephthalate (PET) film (Teijin Film Solution Co., Ltd., trade name "G2J") (support) having a thickness of 16 ⁇ m, and hot air convection drying at 75 ° C and 125 ° C.
- PET polyethylene terephthalate
- the film was sequentially dried in a vessel to form a photosensitive layer having a thickness of 25 ⁇ m after drying.
- a polypropylene film (Tamapoli Co., Ltd., trade name "NF-13”) (protective layer) is laminated on this photosensitive layer, and a support, a photosensitive layer, and a protective layer are laminated in this order, respectively. Obtained.
- the copper surface of the copper-clad laminate was etched to prepare a substrate having eight round holes having a diameter of 200 ⁇ m and a depth of 11 ⁇ m.
- the substrate was heated to 80 ° C., and the photosensitive element was laminated on the substrate.
- Lamination was performed using a heat roll at 110 ° C. at a crimping pressure of 0.3 MPa and a roll speed of 1.5 m / min on the substrate while removing the protective layer. In this way, a laminated body in which the substrate, the photosensitive layer, and the support were laminated in this order was obtained.
- the round hole portion was observed from directly above the laminate using an optical microscope (Keyence Corporation, VK-8500), and the diameter of bubbles generated between the round hole of the substrate and the photosensitive layer was measured. The smaller the diameter of the bubble, the better the followability.
- the photosensitive resin composition containing the binder polymer having a specific structure can form a photosensitive layer having excellent followability.
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Abstract
Description
本実施形態に係る感光性樹脂組成物は、バインダーポリマーと、光重合性化合物と、光重合開始剤と、を含有し、バインダーポリマーが、カルボキシ基を有する重合性単量体に由来する構造単位(a1)と、スチレン又はスチレン誘導体に由来する構造単位(a2)と、炭素数が1~3のアルキル基を有するアルキル(メタ)アクリルレートに由来する構造単位(a3)と、炭素数が4~12のアルキル基を有するアルキル(メタ)メタクリレートに由来する構造単位(a4)とを有する。以下、本実施形態における感光性樹脂組成物で用いられる各成分について詳細に説明する。 [Photosensitive resin composition]
The photosensitive resin composition according to the present embodiment contains a binder polymer, a photopolymerizable compound, and a photopolymerization initiator, and the binder polymer is a structural unit derived from a polymerizable monomer having a carboxy group. (A1), a structural unit (a2) derived from styrene or a styrene derivative, a structural unit (a3) derived from an alkyl (meth) acrylic rate having an alkyl group having 1 to 3 carbon atoms, and 4 carbon atoms. It has a structural unit (a4) derived from an alkyl (meth) methacrylate having up to 12 alkyl groups. Hereinafter, each component used in the photosensitive resin composition in the present embodiment will be described in detail.
本実施形態に係る(A)成分は、カルボキシ基を有する構造単位(a1)と、スチレン又はスチレン誘導体に由来する構造単位(a2)と、炭素数が1~3のアルキル基を有するアルキル(メタ)アクリルレートに由来する構造単位(a3)と、炭素数が4~12のアルキル基を有するアルキル(メタ)メタクリレートに由来する構造単位(a4)とを有するバインダーポリマーを含む。 ((A) component: binder polymer)
The component (A) according to the present embodiment includes a structural unit (a1) having a carboxy group, a structural unit (a2) derived from styrene or a styrene derivative, and an alkyl (meth) having an alkyl group having 1 to 3 carbon atoms. ) A binder polymer having a structural unit (a3) derived from an acrylic rate and a structural unit (a4) derived from an alkyl (meth) methacrylate having an alkyl group having 4 to 12 carbon atoms.
(B)成分としては、エチレン性不飽和結合を少なくとも1つ有し、光重合可能な化合物であれば特に限定されない。エチレン性不飽和結合は、光重合が可能であれば特に限定されない。エチレン性不飽和結合としては、例えば、(メタ)アクリロイル基等のα,β-不飽和カルボニル基が挙げられる。 (Component (B): photopolymerizable compound)
The component (B) is not particularly limited as long as it has at least one ethylenically unsaturated bond and is photopolymerizable. The ethylenically unsaturated bond is not particularly limited as long as photopolymerization is possible. Examples of the ethylenically unsaturated bond include α, β-unsaturated carbonyl groups such as (meth) acryloyl group.
(C)成分としては、(B)成分を重合させることができるものであれば、特に制限は無く、通常用いられる光重合開始剤から適宜選択することができる。パターン形成性を向上させる観点から、活性光線により遊離ラジカルを生成するもの、例えば、アシルホスフィンオキサイド系、オキシムエステル系、芳香族ケトン系、キノン系、アルキルフェノン系、イミダゾール系、アクリジン系、フェニルグリシン系、クマリン系等の光重合開始剤が挙げられる。 (Component (C): Photopolymerization Initiator)
The component (C) is not particularly limited as long as it can polymerize the component (B), and can be appropriately selected from commonly used photopolymerization initiators. From the viewpoint of improving pattern formation, those that generate free radicals by active light, for example, acylphosphine oxide type, oxime ester type, aromatic ketone type, quinone type, alkylphenone type, imidazole type, aclysine type, phenylglycine. Examples thereof include photopolymerization initiators such as radicals and quinones.
本実施形態に係る感光性樹脂組成物は、(D)成分として340~430nmに吸収を有する増感剤を更に含有してよい。これにより、感光性樹脂組成物の光感度が更に良好となる。増感剤としては、例えば、ジアルキルアミノベンゾフェノン化合物、ピラゾリン化合物、アントラセン化合物、クマリン化合物、キサントン化合物、オキサゾール化合物、ベンゾオキサゾール化合物、チアゾール化合物、ベンゾチアゾール化合物、トリアゾール化合物、スチルベン化合物、トリアジン化合物、チオフェン化合物、ナフタルイミド化合物、及びトリアリールアミン化合物が挙げられる。増感剤は、感度及び密着性の観点から、ピラゾリン化合物、アントラセン化合物、クマリン化合物、及びトリアリールアミン化合物からなる群より選ばれる少なくとも1種を含んでよく、ピラゾリン化合物、アントラセン化合物、及びクマリン化合物からなる群より選ばれる少なくとも1種を含んでよい。 ((D) component: sensitizer)
The photosensitive resin composition according to the present embodiment may further contain a sensitizer having absorption at 340 to 430 nm as the component (D). As a result, the light sensitivity of the photosensitive resin composition becomes even better. Examples of the sensitizer include dialkylaminobenzophenone compounds, pyrazoline compounds, anthracene compounds, coumarin compounds, xanthone compounds, oxazole compounds, benzoxazole compounds, thiazole compounds, benzothiazole compounds, triazole compounds, stylben compounds, triazine compounds and thiophene compounds. , Naphthalimide compounds, and triarylamine compounds. The sensitizer may contain at least one selected from the group consisting of pyrazoline compounds, anthracene compounds, coumarin compounds, and triarylamine compounds from the viewpoint of sensitivity and adhesion, and may contain pyrazoline compounds, anthracene compounds, and coumarin compounds. It may contain at least one selected from the group consisting of.
本実施形態に係る感光性樹脂組成物は、(E)成分として熱安定剤を更に含有してよい。(E)成分としては、例えば、ベンゾキノン、ハイドロキノン等のキノン誘導体、4-メトキシフェノール、4-t-ブチルカテコール等のフェノール誘導体(ヒンダードフェノール誘導体)、2,2,6,6-テトラメチルピペリジン-1-オキシル、4-ヒドロキシ-2,2,6,6-テトラメチルピペリジン-1-オキシル等のアミノキシル誘導体、テトラメチルピペリジルメタクリレート等のヒンダードアミン誘導体が挙げられる。中でも(E)成分としてアミノキシル誘導体を用いることで、感光性樹脂組成物が良好な感度を有しつつ、形成されるレジストパターンの解像度及び密着性をより向上させることができる。 ((E) component: heat stabilizer)
The photosensitive resin composition according to the present embodiment may further contain a heat stabilizer as the component (E). Examples of the component (E) include quinone derivatives such as benzoquinone and hydroquinone, phenol derivatives such as 4-methoxyphenol and 4-t-butylcatechol (hindered phenol derivatives), and 2,2,6,6-tetramethylpiperidine. Examples thereof include aminoxyl derivatives such as -1-oxyl and 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, and hindered amine derivatives such as tetramethylpiperidylmethacrylate. Above all, by using the aminoxyl derivative as the component (E), it is possible to further improve the resolution and adhesion of the resist pattern to be formed while the photosensitive resin composition has good sensitivity.
本実施形態に係る感光性樹脂組成物には、必要に応じて、染料、光発色剤、熱発色防止剤、可塑剤、顔料、充填剤、消泡剤、難燃剤、密着性付与剤、レベリング剤、剥離促進剤、酸化防止剤、香料、イメージング剤、熱架橋剤、重合禁止剤等の添加剤を更に含有してもよい。これらの添加剤は、1種を単独で又は2種以上を組み合わせて用いることができる。 (Other ingredients)
The photosensitive resin composition according to the present embodiment contains, if necessary, a dye, a photocoloring agent, a heat coloring inhibitor, a plasticizer, a pigment, a filler, a defoaming agent, a flame retardant, an adhesion imparting agent, and leveling. Additives such as agents, peeling accelerators, antioxidants, fragrances, imaging agents, thermal cross-linking agents, and polymerization inhibitors may be further contained. These additives may be used alone or in combination of two or more.
本実施形態の感光性エレメントは、支持体と、該支持体上に形成されたと感光層とを備え、感光層は上述の感光性樹脂組成物を含む。本実施形態の感光性エレメントを用いる場合には、感光層を基板上にラミネートした後、支持体(支持フィルム)を剥離することなく露光してもよい。本実施形態に係る感光性エレメント1は、図1にその一例の模式断面図を示すように、支持体2と、支持体2上に形成された上記感光性樹脂組成物に由来する感光層3とを備え、必要に応じて設けられる保護層4等のその他の層を備えて構成される。 [Photosensitive element]
The photosensitive element of the present embodiment includes a support and a photosensitive layer formed on the support, and the photosensitive layer includes the above-mentioned photosensitive resin composition. When the photosensitive element of the present embodiment is used, the photosensitive layer may be laminated on the substrate and then exposed without peeling the support (support film). The
支持体しては、例えば、ポリエチレンテレフタレート(PET)、ポリブチレンテレフタレート(PBT)、ポリエチレン-2,6-ナフタレート(PEN)等のポリエステルフィルム、及びポリプロピレン、ポリエチレン等のポリオレフィンフィルムが挙げられる。中でも、入手し易く、且つ、製造工程におけるハンドリング性(特に、耐熱性、熱収縮率、破断強度)に優れる点で、PETフィルムであってもよい。 (Support)
Examples of the support include polyester films such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene-2,6-naphthalate (PEN), and polyolefin films such as polypropylene and polyethylene. Among them, a PET film may be used because it is easily available and has excellent handleability (particularly, heat resistance, heat shrinkage rate, breaking strength) in the manufacturing process.
感光性エレメントは、必要に応じて保護層を更に備えてもよい。保護層としては、感光層と支持体との間の接着力よりも、感光層と保護層との間の接着力が小さくなるようなフィルムを用いてもよく、また、低フィッシュアイのフィルムを用いてもよい。具体的には、例えば、上述する支持体として用いることができるフィルムが挙げられる。感光層からの剥離性の見地から、保護層としてポリエチレンフィルムを用いてもよい。保護層の厚さは、用途により異なるが、1~100μm程度であってもよい。 (Protective layer)
The photosensitive element may be further provided with a protective layer, if necessary. As the protective layer, a film may be used in which the adhesive force between the photosensitive layer and the protective layer is smaller than the adhesive force between the photosensitive layer and the support, and a low fisheye film may be used. You may use it. Specifically, for example, a film that can be used as the above-mentioned support can be mentioned. From the viewpoint of peelability from the photosensitive layer, a polyethylene film may be used as the protective layer. The thickness of the protective layer varies depending on the application, but may be about 1 to 100 μm.
本実施形態のレジストパターンの形成方法は、(i)基板上に、上記感光性樹脂組成物、又は、上記感光性エレメントを用いて、感光層を形成する工程(感光層形成工程)と、(ii)上記感光層の少なくとも一部(所定部分)に活性光線を照射して、光硬化部を形成する工程(露光工程)と、(iii)上記基板上から上記未光硬化部の少なくとも一部を除去する工程(現像工程)と、を備え、必要に応じてその他の工程を含んで構成されてもよい。レジストパターンとは、感光性樹脂組成物の光硬化物パターンともいえ、レリーフパターンともいえる。レジストパターンの形成方法は、レジストパターン付き基板の製造方法ともいえる。 [Method of forming resist pattern]
The method for forming the resist pattern of the present embodiment is as follows: (i) a step of forming a photosensitive layer on a substrate by using the photosensitive resin composition or the photosensitive element (photosensitive layer forming step). ii) A step (exposure step) of irradiating at least a part (predetermined part) of the photosensitive layer with active light to form a photocurable portion, and (iii) at least a part of the unphotocured portion from the substrate. It may be configured to include a step (development step) for removing the above-mentioned light, and if necessary, other steps. The resist pattern can be said to be a photocured product pattern of the photosensitive resin composition, and can also be said to be a relief pattern. The method for forming a resist pattern can also be said to be a method for manufacturing a substrate with a resist pattern.
基板上に感光層を形成する方法としては、例えば、上記感光性樹脂組成物を塗布及び乾燥してもよく、又は、上記感光性エレメントから保護層を除去した後、感光性エレメントの感光層を加熱しながら上記基板に圧着してもよい。感光性エレメントを用いた場合、基板と感光層と支持体とからなり、これらが順に積層された積層体が得られる。上記基板としては特に制限されないが、通常、絶縁層と絶縁層上に形成された導体層とを備えた回路形成用基板、又は合金基材等のダイパッド(リードフレーム用基材)が用いられる。 ((I) Photosensitive layer forming step)
As a method for forming the photosensitive layer on the substrate, for example, the photosensitive resin composition may be applied and dried, or after the protective layer is removed from the photosensitive element, the photosensitive layer of the photosensitive element is formed. It may be crimped to the above substrate while heating. When a photosensitive element is used, it is composed of a substrate, a photosensitive layer, and a support, and a laminated body in which these are laminated in order can be obtained. The substrate is not particularly limited, but usually, a circuit forming substrate provided with an insulating layer and a conductor layer formed on the insulating layer, or a die pad (lead frame substrate) such as an alloy substrate is used.
露光工程においては、基板上に形成された感光層の少なくとも一部に活性光線を照射することで、活性光線が照射された部分が光硬化して、潜像が形成される。この際、感光層上に支持体が存在する場合、その支持体が活性光線に対して透過性であれば、支持体を通して活性光線を照射することができるが、支持体が遮光性の場合には、支持体を除去した後に感光層に活性光線を照射する。 ((Ii) exposure step)
In the exposure step, by irradiating at least a part of the photosensitive layer formed on the substrate with the active light beam, the portion irradiated with the active light ray is photocured to form a latent image. At this time, when the support is present on the photosensitive layer, the active light can be irradiated through the support if the support is transparent to the active light, but if the support is light-shielding. Irradiates the photosensitive layer with active light rays after removing the support.
現像工程においては、上記感光層の未光硬化部(光硬化部以外)の少なくとも一部が基板上から除去されることで、レジストパターンが基板上に形成される。 ((Iii) development process)
In the developing step, a resist pattern is formed on the substrate by removing at least a part of the unphotocured portion (other than the photocured portion) of the photosensitive layer from the substrate.
本実施形態のプリント配線板の製造方法は、上記レジストパターンの形成方法によって、レジストパターンが形成された基板をエッチング処理又はめっき処理して導体パターンを形成する工程を含み、必要に応じて、レジストパターン除去工程等のその他の工程を含んで構成されてもよい。 [Manufacturing method of printed wiring board]
The method for manufacturing a printed wiring board of the present embodiment includes a step of etching or plating a substrate on which a resist pattern is formed by the method for forming a resist pattern to form a conductor pattern, and if necessary, a resist. It may be configured to include other steps such as a pattern removing step.
実施例及び比較例で用いるバインダーポリマーを合成するための重合性単量体として、メタクリル酸(MAA)、スチレン(ST)、メチルメタクリレート(MMA)、ブチルメタクリレート(BMA)、ブチルアクリレート(BA)、2-エチルヘキシルアクリレート(EHA)、エチルアクリレート(AEEC)、及びベンジルメタクリレート(BZMA)を準備した。 [Binder polymer]
Methacrylic acid (MAA), styrene (ST), methyl methacrylate (MMA), butyl methacrylate (BMA), butyl acrylate (BA), as polymerizable monomers for synthesizing the binder polymers used in Examples and Comparative Examples. 2-Ethylhexyl acrylate (EHA), ethyl acrylate (AEEC), and benzyl methacrylate (BZMA) were prepared.
メタクリル酸(MAA)25.5g、スチレン(ST)52.9g、メチルメタクリレート(MMA)9.9g、ブチルアクリレート(BA)3.2g、ベンジルメタクリレート(BZMA)23.5g、4-メトキシフェノール0.02g、及びアゾビスイソブチロニトリル0.7gを混合して、溶液aを調製した。また、プロピレングリコールモノメチルエーテル9g、トルエン7.6g、及びアゾビスイソブチロニトリル0.14gを混合して、溶液bを調製した。さらに、プロピレングリコールモノメチルエーテル4.5g、トルエン7.6g、及びアゾビスイソブチロニトリル0.5gを混合して、溶液cを調製した。 (Binder polymer (A-1))
Methacrylic acid (MAA) 25.5 g, styrene (ST) 52.9 g, methyl methacrylate (MMA) 9.9 g, butyl acrylate (BA) 3.2 g, benzyl methacrylate (BZMA) 23.5 g, 4-methoxyphenol 0. 02 g and 0.7 g of azobisisobutyronitrile were mixed to prepare a solution a. Further, 9 g of propylene glycol monomethyl ether, 7.6 g of toluene, and 0.14 g of azobisisobutyronitrile were mixed to prepare a solution b. Further, 4.5 g of propylene glycol monomethyl ether, 7.6 g of toluene, and 0.5 g of azobisisobutyronitrile were mixed to prepare a solution c.
重合性単量体を表1又は表2に示す材料を同表に示す質量比で用いた以外は、バインダーポリマー(A-1)の溶液を得るのと同様にして、バインダーポリマー(A-2)~(A-18)の溶液を得た。 (Binder Polymers (A-2) to (A-18))
The binder polymer (A-2) was obtained in the same manner as in obtaining the solution of the binder polymer (A-1), except that the polymerizable monomer was used in the mass ratio shown in Table 1 or Table 2. )-(A-18) was obtained.
バインダーポリマー溶液を120mg採取し、5mLのテトラヒドロフランに溶解して、Mw測定用の試料を調製した。Mwは、ゲルパーミエーションクロマトグラフィー法(GPC)によって測定し、標準ポリスチレンの検量線を用いて換算することにより導出した。GPCの条件を以下に示す。 (Weight average molecular weight)
120 mg of the binder polymer solution was collected and dissolved in 5 mL of tetrahydrofuran to prepare a sample for Mw measurement. Mw was measured by gel permeation chromatography (GPC) and derived by conversion using a standard polystyrene calibration curve. The conditions of GPC are shown below.
ポンプ:日立 L-6000型(株式会社日立製作所製)
カラム:Gelpack GL-R440、Gelpack GL-R450及びGelpack GL-R440M(昭和電工マテリアルズ・テクノサービス株式会社製、カラム仕様:10.7mmφ×300mm)
溶離液:テトラヒドロフラン
測定温度:40℃
注入量:200μL
圧力:49Kgf/cm2(4.8MPa)
流量:2.05mL/分
検出器:日立 L-2490型RI(株式会社日立製作所製) (GPC condition)
Pump: Hitachi L-6000 type (manufactured by Hitachi, Ltd.)
Column: Gelpack GL-R440, Gelpack GL-R450 and Gelpack GL-R440M (manufactured by Showa Denko Materials Techno Service Co., Ltd., column specifications: 10.7 mmφ x 300 mm)
Eluent: Tetrahydrofuran Measurement temperature: 40 ° C
Injection volume: 200 μL
Pressure: 49 Kgf / cm 2 (4.8 MPa)
Flow rate: 2.05 mL / min Detector: Hitachi L-2490 type RI (manufactured by Hitachi, Ltd.)
酸価は、JIS K0070に基づいた中和滴定法により測定した。バインダーポリマー約1gに混合溶剤(質量比:トルエン/メタノール=70/30)を加えて溶解した溶液に、指示薬としてフェノールフタレイン溶液を適量添加し、0.1Nの水酸化カリウム水溶液で滴定を行うことで、バインダーポリマーの酸価を測定した。 (Acid value)
The acid value was measured by a neutralization titration method based on JIS K0070. An appropriate amount of a phenolphthalein solution is added as an indicator to a solution prepared by adding a mixed solvent (mass ratio: toluene / methanol = 70/30) to about 1 g of the binder polymer, and titration is performed with a 0.1 N potassium hydroxide aqueous solution. Therefore, the acid value of the binder polymer was measured.
バインダーポリマーのガラス転移温度(Tg)は、Foxの式から算出した。 (Glass-transition temperature)
The glass transition temperature (Tg) of the binder polymer was calculated from the Fox formula.
表3又は表4に示す配合量(質量部)の(A)、(B)及び(C)成分と、溶剤であるメタノール5質量部、トルエン10質量部、及びアセトン11質量部とを混合することにより、実施例及び比較例の感光性樹脂組成物をそれぞれ調製した。表3及び4に示すバインダーポリマーの配合量は、不揮発分の質量(固形分量)である。 [Photosensitive resin composition]
The components (A), (B) and (C) of the blending amount (parts by mass) shown in Table 3 or Table 4 are mixed with 5 parts by mass of methanol, 10 parts by mass of toluene and 11 parts by mass of acetone as solvents. As a result, the photosensitive resin compositions of Examples and Comparative Examples were prepared, respectively. The blending amount of the binder polymer shown in Tables 3 and 4 is the mass of the non-volatile component (solid content amount).
((B)成分:光重合性化合物)
B-1:FA-321M 2,2-ビス(4-(メタクリロキシペンタエトキシ)フェニル)プロパン(昭和電工マテリアルズ株式会社)
B-2:FA-MECH γ-クロロ-β-ヒドロキシプロピル-β’-メタクリロイルオキシエチル-o-フタレート(昭和電工マテリアルズ株式会社)
B-3:M2200 エトキシ化ビスフェノールAジメタクリレート(EO平均20mol変性)(Miwon社製)
B-4:BPE-200 エトキシ化ビスフェノールAジメタクリレート(EO平均4mol変性)(新中村化学工業株式会社)
B-5:SR454 EO変性トリメチロールプロパンアクリレート(巴工業株式会社)
B-6:FA-137M EO変性トリメチロールプロパンアクリレート(昭和電工マテリアルズ株式会社)
B-7:DPEA-12 EO基を有するジペンタエリスリトール(メタ)アクリレート(日本化薬株式会社)
B-8:UA-21 トリス(メタクリロキシテトラエチレングリコールイソシアネート)ヘキサメチレンイソシアヌレート(新中村化学工業株式会社)
B-9:FA-024M EOPO変性ジメタクリレート(昭和電工マテリアルズ株式会社)
((C)成分:光重合開始剤)
C-1:9-PA 9-フェニルアクリジン(常州強力電子新材料株式会社)
C-2:N-PG N-フェニルグリシン(常州強力電子新材料株式会社)
C-3:B-CIM 2,2’-ビス(2-クロロフェニル)-4,4’,5,5’-テトラフェニルビイミダゾール(保土谷化学工業株式会社)
((D)成分:増感剤)
D-1:DBA 9,10-ジブトキシアントラセン(川崎化成工業株式会社) Details of each component shown in Tables 3 and 4 are as follows.
(Component (B): photopolymerizable compound)
B-1: FA-
B-2: FA-MECH γ-chloro-β-hydroxypropyl-β'-methacryloyloxyethyl-o-phthalate (Showa Denko Materials Co., Ltd.)
B-3: M2200 ethoxylated bisphenol A dimethacrylate (EO average 20 mol denaturation) (manufactured by Miwon)
B-4: BPE-200 ethoxylated bisphenol A dimethacrylate (
B-5: SR454 EO-modified trimethylolpropane acrylate (Tomoe Kogyo Co., Ltd.)
B-6: FA-137M EO-modified trimethylolpropane acrylate (Showa Denko Materials Co., Ltd.)
B-7: Dipentaerythritol (meth) acrylate having a DPEA-12 EO group (Nippon Kayaku Co., Ltd.)
B-8: UA-21 Tris (methacryloxytetraethylene glycol isocyanate) hexamethylene isocyanurate (Shin Nakamura Chemical Industry Co., Ltd.)
B-9: FA-024M EOPO modified dimethacrylate (Showa Denko Materials Co., Ltd.)
(Component (C): Photopolymerization Initiator)
C-1: 9-PA 9-Phenyl Acridine (Changzhou Strong Electronics New Materials Co., Ltd.)
C-2: N-PG N-Phenylglycine (Changzhou Strong Electronics New Materials Co., Ltd.)
C-3: B-
((D) component: sensitizer)
D-1: DBA 9,10-Dibutoxyanthracene (Kawasaki Kasei Industrial Co., Ltd.)
感光性樹脂組成物の溶液を、厚み16μmのポリエチレンテレフタレート(PET)フィルム(帝人フィルムソリューション株式会社、商品名「G2J」)(支持体)上に塗布し、75℃及び125℃の熱風対流式乾燥器で順次乾燥して、乾燥後の厚みが25μmの感光層を形成した。この感光層上にポリプロピレンフィルム(タマポリ株式会社、商品名「NF-13」)(保護層)を貼り合わせ、支持体と、感光層と、保護層とがこの順に積層された感光性エレメントをそれぞれ得た。 [Photosensitive element]
A solution of the photosensitive resin composition is applied onto a polyethylene terephthalate (PET) film (Teijin Film Solution Co., Ltd., trade name "G2J") (support) having a thickness of 16 μm, and hot air convection drying at 75 ° C and 125 ° C. The film was sequentially dried in a vessel to form a photosensitive layer having a thickness of 25 μm after drying. A polypropylene film (Tamapoli Co., Ltd., trade name "NF-13") (protective layer) is laminated on this photosensitive layer, and a support, a photosensitive layer, and a protective layer are laminated in this order, respectively. Obtained.
銅張積層板の銅表面をエッチングして、直径200μm及び深さ11μmの丸穴を8箇所に形成した基板を作製した。次いで、基板を80℃に加温し、感光性エレメントを基板に積層した。積層は、110℃のヒートロールを用いて、保護層を除去しながら、基板の0.3MPaの圧着圧力、1.5m/分のロール速度で行った。こうして、基板と感光層と支持体とがこの順に積層された積層体を得た。光学顕微鏡(キーエンス株式会社、VK-8500)を用いて積層体の真上から丸穴部を観察して、基板の丸穴と感光層との間に発生する気泡の直径を測定した。気泡の直径が小さいほど、追従性に優れることを意味する。 (Followability)
The copper surface of the copper-clad laminate was etched to prepare a substrate having eight round holes having a diameter of 200 μm and a depth of 11 μm. Next, the substrate was heated to 80 ° C., and the photosensitive element was laminated on the substrate. Lamination was performed using a heat roll at 110 ° C. at a crimping pressure of 0.3 MPa and a roll speed of 1.5 m / min on the substrate while removing the protective layer. In this way, a laminated body in which the substrate, the photosensitive layer, and the support were laminated in this order was obtained. The round hole portion was observed from directly above the laminate using an optical microscope (Keyence Corporation, VK-8500), and the diameter of bubbles generated between the round hole of the substrate and the photosensitive layer was measured. The smaller the diameter of the bubble, the better the followability.
Claims (11)
- バインダーポリマーと、光重合性化合物と、光重合開始剤と、を含有する感光性樹脂組成物であって、
前記バインダーポリマーが、カルボキシ基を有する重合性単量体に由来する構造単位(a1)と、スチレン又はスチレン誘導体に由来する構造単位(a2)と、炭素数が1~3のアルキル基を有するアルキル(メタ)アクリルレートに由来する構造単位(a3)と、炭素数が4~12のアルキル基を有するアルキル(メタ)メタクリレートに由来する構造単位(a4)とを有する、感光性樹脂組成物。 A photosensitive resin composition containing a binder polymer, a photopolymerizable compound, and a photopolymerization initiator.
The binder polymer has a structural unit (a1) derived from a polymerizable monomer having a carboxy group, a structural unit (a2) derived from styrene or a styrene derivative, and an alkyl having 1 to 3 carbon atoms. A photosensitive resin composition having a structural unit (a3) derived from (meth) acrylic rate and a structural unit (a4) derived from alkyl (meth) methacrylate having an alkyl group having 4 to 12 carbon atoms. - 前記バインダーポリマーの酸価が、100mgKOH/g以上180mgKOH/g以下である、請求項1に記載の感光性樹脂組成物。 The photosensitive resin composition according to claim 1, wherein the acid value of the binder polymer is 100 mgKOH / g or more and 180 mgKOH / g or less.
- 前記バインダーポリマーの重量平均分子量が、10000以上60000以下である、請求項1又は2に記載の感光性樹脂組成物。 The photosensitive resin composition according to claim 1 or 2, wherein the binder polymer has a weight average molecular weight of 10,000 or more and 60,000 or less.
- 前記構造単位(a4)の含有量が、前記バインダーポリマーの全体量を基準として、0.5~30質量%である、請求項1~3のいずれか一項に記載の感光性樹脂組成物。 The photosensitive resin composition according to any one of claims 1 to 3, wherein the content of the structural unit (a4) is 0.5 to 30% by mass based on the total amount of the binder polymer.
- 前記光重合開始剤が、アクリジン系光重合開始剤を含む、請求項1~4のいずれか一項に記載の感光性樹脂組成物。 The photosensitive resin composition according to any one of claims 1 to 4, wherein the photopolymerization initiator contains an acridine-based photopolymerization initiator.
- 前記光重合性化合物が、ビスフェノール型ジ(メタ)アクリレートを含む、請求項1~5のいずれか一項に記載の感光性樹脂組成物。 The photosensitive resin composition according to any one of claims 1 to 5, wherein the photopolymerizable compound contains a bisphenol type di (meth) acrylate.
- 前記光重合性化合物が、ジペンタエリスリトール又はペンタエリスリトール由来の骨格を有する(メタ)アクリレート化合物を含む、請求項1~6のいずれか一項に記載の感光性樹脂組成物。 The photosensitive resin composition according to any one of claims 1 to 6, wherein the photopolymerizable compound contains dipentaerythritol or a (meth) acrylate compound having a skeleton derived from pentaerythritol.
- 支持体と、該支持体上に形成された感光層と、を備え、
前記感光層が、請求項1~7のいずれか一項に記載の感光性樹脂組成物を含む、感光性エレメント。 A support and a photosensitive layer formed on the support are provided.
A photosensitive element in which the photosensitive layer contains the photosensitive resin composition according to any one of claims 1 to 7. - 基板上に、請求項1~7のいずれか一項に記載の感光性樹脂組成物又は請求項8に記載の感光性エレメントを用いて、感光層を形成する工程と、
前記感光層の少なくとも一部に活性光線を照射して、光硬化部を形成する工程と、
前記基板から、前記感光層の未光硬化部の少なくとも一部を除去する工程と、
を備える、レジストパターンの形成方法。 A step of forming a photosensitive layer on a substrate by using the photosensitive resin composition according to any one of claims 1 to 7 or the photosensitive element according to claim 8.
A step of irradiating at least a part of the photosensitive layer with active light to form a photocurable portion, and
A step of removing at least a part of the unlightened portion of the photosensitive layer from the substrate,
A method of forming a resist pattern. - 請求項9に記載のレジストパターンの形成方法によりレジストパターンが形成された基板をエッチング処理又はめっき処理して、導体パターンを形成する工程を備える、プリント配線板の製造方法。 A method for manufacturing a printed wiring board, comprising a step of forming a conductor pattern by etching or plating a substrate on which a resist pattern is formed by the method for forming a resist pattern according to claim 9.
- 前記エッチング処理又はめっき処理の後に、前記レジストパターンを除去する工程を更に備える、請求項10に記載のプリント配線板の製造方法。
The method for manufacturing a printed wiring board according to claim 10, further comprising a step of removing the resist pattern after the etching treatment or the plating treatment.
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KR1020237019362A KR20230109152A (en) | 2020-11-24 | 2021-11-16 | Photosensitive resin composition, photosensitive element, method for forming a resist pattern, and method for manufacturing a printed wiring board |
JP2022562370A JP7425982B2 (en) | 2020-11-24 | 2021-11-16 | Photosensitive resin composition, photosensitive element, resist pattern forming method, and printed wiring board manufacturing method |
CN202210896651.8A CN115167077A (en) | 2020-11-24 | 2021-11-16 | Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for producing printed wiring board |
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JPH03236956A (en) * | 1989-05-17 | 1991-10-22 | Asahi Chem Ind Co Ltd | Photo-setting resin laminate and manufacture of printed wiring board using the same |
JP2010020264A (en) * | 2007-08-09 | 2010-01-28 | Nichigo Morton Co Ltd | Solder resist film, resist pattern forming method and luminescent device |
WO2013141286A1 (en) * | 2012-03-23 | 2013-09-26 | 日立化成株式会社 | Photosensitive resin composition, method for manufacturing processed glass substrate using same, and touch panel and method for manufacturing same |
JP2017129736A (en) * | 2016-01-20 | 2017-07-27 | 互応化学工業株式会社 | Photosensitive resin composition, dry film, printed wiring board and production method of photosensitive resin composition |
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JP4935833B2 (en) * | 2009-01-23 | 2012-05-23 | 日立化成工業株式会社 | Photosensitive resin composition, photosensitive element using the same, method for forming partition of image display device, and method for manufacturing image display device |
JP2010249884A (en) * | 2009-04-10 | 2010-11-04 | Dupont Mrc Dryfilm Ltd | Photopolymerizable resin composition and photosensitive film using the same |
JP5777461B2 (en) | 2011-09-14 | 2015-09-09 | 旭化成イーマテリアルズ株式会社 | Photosensitive resin composition |
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JPH03236956A (en) * | 1989-05-17 | 1991-10-22 | Asahi Chem Ind Co Ltd | Photo-setting resin laminate and manufacture of printed wiring board using the same |
JP2010020264A (en) * | 2007-08-09 | 2010-01-28 | Nichigo Morton Co Ltd | Solder resist film, resist pattern forming method and luminescent device |
WO2013141286A1 (en) * | 2012-03-23 | 2013-09-26 | 日立化成株式会社 | Photosensitive resin composition, method for manufacturing processed glass substrate using same, and touch panel and method for manufacturing same |
JP2017129736A (en) * | 2016-01-20 | 2017-07-27 | 互応化学工業株式会社 | Photosensitive resin composition, dry film, printed wiring board and production method of photosensitive resin composition |
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