JP4941182B2 - 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 - Google Patents
感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 Download PDFInfo
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- JP4941182B2 JP4941182B2 JP2007223040A JP2007223040A JP4941182B2 JP 4941182 B2 JP4941182 B2 JP 4941182B2 JP 2007223040 A JP2007223040 A JP 2007223040A JP 2007223040 A JP2007223040 A JP 2007223040A JP 4941182 B2 JP4941182 B2 JP 4941182B2
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- Prior art keywords
- phenyl
- group
- resin composition
- photosensitive resin
- pyrazoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims description 96
- 238000000034 method Methods 0.000 title claims description 49
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- -1 pyrazoline compound Chemical class 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 238000011161 development Methods 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 20
- 239000011230 binding agent Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000004020 conductor Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000010030 laminating Methods 0.000 claims description 10
- 230000001678 irradiating effect Effects 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 56
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 46
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 239000001294 propane Substances 0.000 description 23
- 230000035945 sensitivity Effects 0.000 description 23
- 230000018109 developmental process Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 238000007747 plating Methods 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229910052753 mercury Inorganic materials 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 238000003475 lamination Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- 150000003219 pyrazolines Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- 150000003673 urethanes Chemical class 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 229920000573 polyethylene Polymers 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
- 239000002904 solvent Substances 0.000 description 3
- 239000007921 spray Substances 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- LENRQXCSNXMCIO-UHFFFAOYSA-N 2-(1-phenylethenyl)-3,5-dithiophen-2-yl-1,3-dihydropyrazole Chemical compound C1(=CC=CC=C1)C(=C)N1NC(=CC1C=1SC=CC1)C=1SC=CC1 LENRQXCSNXMCIO-UHFFFAOYSA-N 0.000 description 2
- RRCAQWOBVNBNJU-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3,5-diphenyl-1,3-dihydropyrazole Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(C=2C=CC=CC=2)C=C(C=2C=CC=CC=2)N1 RRCAQWOBVNBNJU-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- MNHBCTZYDGDGAS-UHFFFAOYSA-N 2-phenyl-3,5-dithiophen-2-yl-1,3-dihydropyrazole Chemical compound C1(=CC=CC=C1)N1NC(=CC1C=1SC=CC=1)C=1SC=CC=1 MNHBCTZYDGDGAS-UHFFFAOYSA-N 0.000 description 2
- JUCBFFBIOKNVFJ-UHFFFAOYSA-N 2-phenyl-3-(2-phenylethenyl)-5-thiophen-2-yl-1,3-dihydropyrazole Chemical compound C1(=CC=CC=C1)N1NC(=CC1C=CC1=CC=CC=C1)C=1SC=CC1 JUCBFFBIOKNVFJ-UHFFFAOYSA-N 0.000 description 2
- DAGTVBOXQIPFQD-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-2-phenyl-5-thiophen-2-yl-1,3-dihydropyrazole Chemical compound C1(=CC=CC=C1)N1NC(=CC1C1=CC=C(C=C1)C(C)(C)C)C=1SC=CC1 DAGTVBOXQIPFQD-UHFFFAOYSA-N 0.000 description 2
- ZEABUURVUDRWCF-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-5-[2-(4-tert-butylphenyl)ethenyl]-2-phenyl-1,3-dihydropyrazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)C(C)(C)C)N(C=2C=CC=CC=2)N1 ZEABUURVUDRWCF-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 101100246550 Caenorhabditis elegans pyr-1 gene Proteins 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 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
- 239000003513 alkali Substances 0.000 description 2
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- 229920001577 copolymer Polymers 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 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
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 150000003022 phthalic acids Chemical class 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- ARGIPZKQJGFSGQ-LCYFTJDESA-N (Z)-PYR-41 Chemical compound C1=CC(C(=O)OCC)=CC=C1N(NC\1=O)C(=O)C/1=C\C1=CC=C([N+]([O-])=O)O1 ARGIPZKQJGFSGQ-LCYFTJDESA-N 0.000 description 1
- FWUIHQFQLSWYED-ARJAWSKDSA-N (z)-4-oxo-4-propan-2-yloxybut-2-enoic acid Chemical compound CC(C)OC(=O)\C=C/C(O)=O FWUIHQFQLSWYED-ARJAWSKDSA-N 0.000 description 1
- SCEFCWXRXJZWHE-UHFFFAOYSA-N 1,2,3-tribromo-4-(2,3,4-tribromophenyl)sulfonylbenzene Chemical compound BrC1=C(Br)C(Br)=CC=C1S(=O)(=O)C1=CC=C(Br)C(Br)=C1Br SCEFCWXRXJZWHE-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- OTEIVXLJOGZQHB-UHFFFAOYSA-N 2,3,5-tris(4-tert-butylphenyl)-1,3-dihydropyrazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1N(C=2C=CC(=CC=2)C(C)(C)C)NC(C=2C=CC(=CC=2)C(C)(C)C)=C1 OTEIVXLJOGZQHB-UHFFFAOYSA-N 0.000 description 1
- GWIBWOHDQWIABB-UHFFFAOYSA-N 2,3-bis(4-dodecylphenyl)-5-[2-(4-dodecylphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1C=CC1=CC(C=2C=CC(CCCCCCCCCCCC)=CC=2)N(C=2C=CC(CCCCCCCCCCCC)=CC=2)N1 GWIBWOHDQWIABB-UHFFFAOYSA-N 0.000 description 1
- ONVANMNFZQFRQW-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-5-[2-(4-methoxyphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(OC)=CC=C1C=CC1=CC(C=2C=CC(OC)=CC=2)N(C=2C=CC(OC)=CC=2)N1 ONVANMNFZQFRQW-UHFFFAOYSA-N 0.000 description 1
- ILNHNXGSEGUUPA-UHFFFAOYSA-N 2,3-bis(4-propan-2-ylphenyl)-5-[2-(4-propan-2-ylphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(C(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)C(C)C)N(C=2C=CC(=CC=2)C(C)C)N1 ILNHNXGSEGUUPA-UHFFFAOYSA-N 0.000 description 1
- NYMOKQCFOQCEGQ-UHFFFAOYSA-N 2,3-bis(4-tert-butylphenyl)-5-[2-(4-tert-butylphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)C(C)(C)C)N(C=2C=CC(=CC=2)C(C)(C)C)N1 NYMOKQCFOQCEGQ-UHFFFAOYSA-N 0.000 description 1
- OXNZQAPFOHXSEJ-UHFFFAOYSA-N 2,3-bis(4-tert-butylphenyl)-5-phenyl-1,3-dihydropyrazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1N(C=2C=CC(=CC=2)C(C)(C)C)NC(C=2C=CC=CC=2)=C1 OXNZQAPFOHXSEJ-UHFFFAOYSA-N 0.000 description 1
- IVYIECJAAQOKEL-UHFFFAOYSA-N 2,3-bis[4-(2,4,4-trimethylpentan-2-yl)phenyl]-5-[2-[4-(2,4,4-trimethylpentan-2-yl)phenyl]ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)C(C)(C)CC(C)(C)C)N(C=2C=CC(=CC=2)C(C)(C)CC(C)(C)C)N1 IVYIECJAAQOKEL-UHFFFAOYSA-N 0.000 description 1
- JTJQQNDYQOPASJ-UHFFFAOYSA-N 2,3-diphenyl-5-(4-propan-2-ylphenyl)-1,3-dihydropyrazole Chemical compound C1=CC(C(C)C)=CC=C1C1=CC(C=2C=CC=CC=2)N(C=2C=CC=CC=2)N1 JTJQQNDYQOPASJ-UHFFFAOYSA-N 0.000 description 1
- UBUGJNBXPJDIJY-UHFFFAOYSA-N 2,3-diphenyl-5-thiophen-2-yl-1,3-dihydropyrazole Chemical compound C1(=CC=CC=C1)N1NC(=CC1C1=CC=CC=C1)C=1SC=CC=1 UBUGJNBXPJDIJY-UHFFFAOYSA-N 0.000 description 1
- QGYREKNBPMFURY-UHFFFAOYSA-N 2,5-diphenyl-3-(4-propan-2-ylphenyl)-1,3-dihydropyrazole Chemical compound C1=CC(C(C)C)=CC=C1C1N(C=2C=CC=CC=2)NC(C=2C=CC=CC=2)=C1 QGYREKNBPMFURY-UHFFFAOYSA-N 0.000 description 1
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
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- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 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
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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Description
[式(1)中、R1及びR2はそれぞれ独立に、炭素数1〜10の直鎖状もしくは分岐状のアルキル基、炭素数1〜10の直鎖状もしくは分岐状のアルコキシ基、アミノ基、炭素数1〜10のアルキル基を持つアルキルアミノ基、炭素数1〜10のアルキル基を持つジアルキルアミノ基及びハロゲン原子からなる群より選ばれる少なくとも1種の置換基で置換されていてもよいチエニル基、又は、炭素数1〜10の直鎖状もしくは分岐状のアルキル基、炭素数1〜10の直鎖状もしくは分岐状のアルコキシ基、アミノ基、炭素数1〜10のアルキル基を持つアルキルアミノ基、炭素数1〜10のアルキル基を持つジアルキルアミノ基及びハロゲン原子からなる群より選ばれる少なくとも1種の置換基で置換されていてもよいフェニル基を示し、且つ、R1及びR2の少なくとも一方は上記チエニル基を示し、R3は炭素数1〜10の直鎖状もしくは分岐状のアルキル基、炭素数1〜10の直鎖状もしくは分岐状のアルコキシ基、又は、ハロゲン原子を示し、l及びmはそれぞれ独立に、0〜3の整数を示し、nは0〜5の整数を示す。但し、nが2以上の場合、複数存在するR3はそれぞれ同一でも異なっていてもよい。]
[式(2)中、Ar1、Ar2、Ar3及びAr4はそれぞれ独立に、アルキル基、アルケニル基及びアルコキシ基からなる群より選ばれる少なくとも1種の置換基で置換されていてもよいアリール基を示し、X1及びX2はそれぞれ独立に、塩素原子、アルキル基、アルケニル基又はアルコキシ基を示し、p及びqはそれぞれ独立に、1〜5の整数を示す。但し、pが2以上の場合、複数存在するX1はそれぞれ同一でも異なっていてもよく、qが2以上の場合、複数存在するX2はそれぞれ同一でも異なっていてもよい。また、X1及びX2のうちの少なくとも1つは塩素原子である。]
本発明の感光性樹脂組成物は、(A)バインダポリマー(以下、場合により「(A)成分」という)と、(B)エチレン性不飽和結合を有する光重合性化合物(以下、場合により「(B)成分」という)と、(C1)上記一般式(1)で表されるピラゾリン化合物(以下、場合により「(C1)成分」という)と、を含有するものである。以下、各成分について詳細に説明する。
次に、本発明の感光性エレメントについて説明する。本発明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上記本発明の感光性樹脂組成物からなる感光性樹脂組成物層と、を備えるものである。
次に、本発明のレジストパターンの形成方法について説明する。本発明のレジストパターンの形成方法は、基板上に、上記本発明の感光性樹脂組成物からなる感光性樹脂組成物層を積層する積層工程と、上記感光性樹脂組成物層の所定部分に活性光線を照射して露光部を光硬化せしめる露光工程と、上記露光部以外の部分を除去してレジストパターンを形成する現像工程と、を有する方法である。
次に、本発明のプリント配線板の製造方法について説明する。本発明のプリント配線板の製造方法は、基板上に、上記本発明の感光性樹脂組成物からなる感光性樹脂組成物層を積層する積層工程と、上記感光性樹脂組成物層の所定部分に活性光線を照射して露光部を光硬化せしめる露光工程と、上記露光部以外の部分を除去してレジストパターンを形成する現像工程と、上記レジストパターンに基づいて導体パターンを形成する導体パターン形成工程と、を有する方法である。ここで、積層工程、露光工程及び現像工程を経てレジストパターンを形成する手順は、上記本発明のレジストパターンの形成方法と同様である。
下記表1〜2に示す配合組成(単位:質量部)に従って組成物を配合し、実施例1〜4及び比較例1〜3の感光性樹脂組成物の溶液を得た。
ビスフェノールA骨格EO変性ジメタクリレート:日立化成工業社製、商品名FA−321M、
EO,PO変性ジメタクリレート:日立化成工業社製、商品名FA−023M、
PYR−1:1−フェニル−3−(2−チエニル)−5−(4−tert−ブチルフェニル)ピラゾリン、
PYR−2:1−フェニル−3−(2−チエニル)エテニル−−5−(2−チエニル)−ピラゾリン、
PYR−3:1−フェニル−3−(2−チエニル)−5−(2−チエニル)−ピラゾリン、
PYR−4:1−フェニル−3−(2−チエニル)−5−スチリルピラゾリン、
EAB:エチルミヒラーズケトン、
RYR−TB:1−フェニル−3−(4−tert−ブチル−スチリル)−5−(4−tert−ブチル−フェニル)ピラゾリン。
実施例及び比較例で得られた感光性エレメントにおいて、感光性樹脂組成物層の露光波長に対する光学密度(O.D.値)を、UV分光光度計(日立製作所社製、商品名:U−3310分光光度計)を用いて測定した。O.D.値の測定は、測定側に支持フィルム及び感光性樹脂組成物層からなる感光性エレメントを置き、リファレンス側に支持フィルムを置き、吸光度モードにより波長550〜300nmの光で連続測定を行ってUV吸収スペクトルを得て、その中で波長405nm、365nm及び355nmにおける吸光度の値を読み取ってO.D.値とした。波長405nmにおける吸光度を表4に、波長365nmにおける吸光度を表5にそれぞれ示す。
実施例及び比較例で得られた感光性エレメントのそれぞれについて、以下の方法により銅張積層板に感光性樹脂組成物層をラミネートし、積層体を得た。すなわち、銅箔(厚み35mm)を両面に積層したガラスエポキシ剤である銅張積層板(日立化成工業(株)製、商品名:MCL−E−67)の銅表面を、#600相当のブラシを持つ研磨機(三啓(株)製)を用いて研磨し、水洗後、空気流で乾燥した。そして、得られた銅張積層板を80℃に加温し、上記銅張積層板上に感光性エレメントを、感光性樹脂組成物層が銅張積層板の表面上に密着するようにして、温度120℃、圧力4kgf/cm2の条件でラミネートすることにより、積層体を得た。
Claims (6)
- (A)バインダポリマーと、
(B)エチレン性不飽和結合を有する光重合性化合物と、
(C1)下記一般式(1)で表されるピラゾリン化合物と、
を含有する、感光性樹脂組成物。
[式(1)中、R1及びR2はそれぞれ独立に、炭素数1〜10の直鎖状もしくは分岐状のアルキル基、炭素数1〜10の直鎖状もしくは分岐状のアルコキシ基、アミノ基、炭素数1〜10のアルキル基を持つアルキルアミノ基、炭素数1〜10のアルキル基を持つジアルキルアミノ基及びハロゲン原子からなる群より選ばれる少なくとも1種の置換基で置換されていてもよいチエニル基、又は、炭素数1〜10の直鎖状もしくは分岐状のアルキル基、炭素数1〜10の直鎖状もしくは分岐状のアルコキシ基、アミノ基、炭素数1〜10のアルキル基を持つアルキルアミノ基、炭素数1〜10のアルキル基を持つジアルキルアミノ基及びハロゲン原子からなる群より選ばれる少なくとも1種の置換基で置換されていてもよいフェニル基を示し、且つ、R1及びR2の少なくとも一方は前記チエニル基を示し、R3は炭素数1〜10の直鎖状もしくは分岐状のアルキル基、炭素数1〜10の直鎖状もしくは分岐状のアルコキシ基、又は、ハロゲン原子を示し、l及びmはそれぞれ独立に、0〜3の整数を示し、nは0〜5の整数を示す。但し、nが2以上の場合、複数存在するR3はそれぞれ同一でも異なっていてもよい。] - 前記一般式(1)中、前記R1及び前記R2の両方が前記チエニル基である、請求項1記載の感光性樹脂組成物。
- (C2)下記一般式(2)で表される2,4,5−トリアリールイミダゾール二量体又はその誘導体を更に含有する、請求項1又は2記載の感光性樹脂組成物。
[式(2)中、Ar1、Ar2、Ar3及びAr4はそれぞれ独立に、アルキル基、アルケニル基及びアルコキシ基からなる群より選ばれる少なくとも1種の置換基で置換されていてもよいアリール基を示し、X1及びX2はそれぞれ独立に、塩素原子、アルキル基、アルケニル基又はアルコキシ基を示し、p及びqはそれぞれ独立に、1〜5の整数を示す。但し、pが2以上の場合、複数存在するX1はそれぞれ同一でも異なっていてもよく、qが2以上の場合、複数存在するX2はそれぞれ同一でも異なっていてもよい。また、X1及びX2のうちの少なくとも1つは塩素原子である。] - 支持体と、該支持体上に形成された請求項1〜3のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層と、を備える感光性エレメント。
- 基板上に、請求項1〜3のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層を積層する積層工程と、
前記感光性樹脂組成物層の所定部分に活性光線を照射して露光部を光硬化せしめる露光工程と、
前記露光部以外の部分を除去してレジストパターンを形成する現像工程と、
を有するレジストパターンの形成方法。 - 基板上に、請求項1〜3のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層を積層する積層工程と、
前記感光性樹脂組成物層の所定部分に活性光線を照射して露光部を光硬化せしめる露光工程と、
前記露光部以外の部分を除去してレジストパターンを形成する現像工程と、
前記レジストパターンに基づいて導体パターンを形成する導体パターン形成工程と、
を有するプリント配線板の製造方法。
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