TWI470007B - A polymer compound containing an epoxy group, a photohardenable resin composition using the compound, a method for forming a pattern, and a method for protecting the electronic parts - Google Patents
A polymer compound containing an epoxy group, a photohardenable resin composition using the compound, a method for forming a pattern, and a method for protecting the electronic parts Download PDFInfo
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- TWI470007B TWI470007B TW99133314A TW99133314A TWI470007B TW I470007 B TWI470007 B TW I470007B TW 99133314 A TW99133314 A TW 99133314A TW 99133314 A TW99133314 A TW 99133314A TW I470007 B TWI470007 B TW I470007B
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- Prior art keywords
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- polymer compound
- resin composition
- compound
- general formula
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- 150000001875 compounds Chemical class 0.000 title claims description 121
- 229920000642 polymer Polymers 0.000 title claims description 79
- 239000011342 resin composition Substances 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 22
- 125000003700 epoxy group Chemical group 0.000 title claims description 17
- -1 methylol groups Chemical group 0.000 claims description 74
- 239000002904 solvent Substances 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 20
- 125000000962 organic group Chemical group 0.000 claims description 15
- 239000003431 cross linking reagent Substances 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000011161 development Methods 0.000 claims description 11
- 150000007514 bases Chemical class 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical group O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000010408 film Substances 0.000 description 64
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 49
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 38
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 25
- 229910052697 platinum Inorganic materials 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- 241000208340 Araliaceae Species 0.000 description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 19
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 19
- 235000003140 Panax quinquefolius Nutrition 0.000 description 19
- 235000008434 ginseng Nutrition 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 14
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 230000018109 developmental process Effects 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000005476 soldering Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 description 5
- 150000007974 melamines Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- 150000003672 ureas Chemical class 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 4
- 150000004060 quinone imines Chemical class 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- PAPNRQCYSFBWDI-UHFFFAOYSA-N DMP Natural products CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 3
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 3
- 150000004892 pyridazines Chemical class 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- SAFWZKVQMVOANB-UHFFFAOYSA-N 2-[tert-butylsulfonyl(diazo)methyl]sulfonyl-2-methylpropane Chemical compound CC(C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)(C)C SAFWZKVQMVOANB-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- DQIASPYBWIPPNR-UHFFFAOYSA-N CCC(C)OC1=CC=C(C=C1)C1=CC=CC2=CC3=CC=CC=C3C=C12 Chemical compound CCC(C)OC1=CC=C(C=C1)C1=CC=CC2=CC3=CC=CC=C3C=C12 DQIASPYBWIPPNR-UHFFFAOYSA-N 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 150000004141 diterpene derivatives Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000000686 lactone group Chemical group 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 2
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 2
- IZJVVXCHJIQVOL-UHFFFAOYSA-N nitro(phenyl)methanesulfonic acid Chemical class OS(=O)(=O)C([N+]([O-])=O)C1=CC=CC=C1 IZJVVXCHJIQVOL-UHFFFAOYSA-N 0.000 description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229940100684 pentylamine Drugs 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
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- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
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- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
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- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- 239000002344 surface layer Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
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- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- 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
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- G—PHYSICS
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- 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
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
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- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
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- G—PHYSICS
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- 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
- G03F7/20—Exposure; Apparatus therefor
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
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Description
本發明係有關一種新穎的含環氧基之高分子化合物、使用它之光硬化性樹脂組成物及圖型形成方法,以及使用該光硬化性樹脂組成物之基板或電路、配線等之電氣‧電子零件保護用皮膜。
特別是該保護用皮膜,由於其耐熱性、藥品耐性、絕緣性及可撓性,除含有再配線用之半導體元件用絕緣膜、多層印刷基板用絕緣膜、焊接光罩,TSV之貫通電極用絕緣膜、覆蓋(coverlay)薄膜外,以及可使用於基板貼合用途等。
以往,具有感光性之半導體元件保護膜或多層印刷基板用絕緣膜,係利用感光性聚醯亞胺或感光性環氧樹脂、感光性聚矽氧等。然後,被使用於該基板、電路保護用之感光性材料,於此等之中特別提案有可撓性優異的感光性聚矽氧組成物(專利文獻1:日本特開2002-88158號公報)。該感光性聚矽氧組成物,例如可在低溫下硬化,且形成耐濕接著性等信賴性優異的皮膜,另外,以對如N-甲基-2-吡咯烷酮之溶解力強的光阻剝離液等之藥品耐性作為要求特性。對此而言,提案有以含有矽伸苯樹脂(Silphenylene)骨架之聚矽氧型高分子化合物為主成分之感光性聚矽氧組成物(專利文獻2:日本特開2008-184571號公報)。上述感光性聚矽氧組成物,可提高對光阻剝離液等之藥品耐性,惟企求更為提高對焊接助劑液之藥品耐性,且更為提高作為半導體元件用保護膜之信賴性。
[專利文獻1]日本特開2002-88158號公報
[專利文獻2]日本特開2008-184571號公報
本發明有鑑於上述情形者,以提供一種可容易以厚膜形成微細的圖型,且即使在低溫之後硬化處理時,仍可形成各種薄膜特性、特別是對焊接助劑液之藥品耐性優異的皮膜,同時可形成作為電氣‧電子元件之信賴性、特別是可防止於溫度循環試驗時產生破裂的皮膜之具有含環氧基之構造的新穎高分子化合物,使用它之光硬化性樹脂組成物,圖型形成方法及電氣‧電子零件保護用皮膜為目的。
本發明人等為達成上述目的時,再三深入研究檢討的結果,發現由使用下述一般式(1)之含環氧基的高分子化合物之光硬化性樹脂組成物所得的皮膜,作為電氣‧電子零件用保護膜優異,遂而完成本發明。
因此,本發明提供下述含環氧基之高分子化合物、光硬化性樹脂組成物、圖型形成方法及電氣‧電子零件用保護皮膜。
申請專利範圍第1項:具有以下述一般式(1)所示之重複單位的重量平均分子量為3,000~500,000的含環氧基之高分子化合物。
【化6】
[式中,R1
~R4
係表示相同或不同的碳數1~8之1價烴基,另外,m係1~100之整數,a、b、c、d係為0或正數,惟c及d不可同時為0,且0<(c+d)/(a+b+c+d)≦1.0;此外,X、Y係各以下述一般式(2)或(3)所示之2價有機基,惟至少具有1個以式(3)所示之2價有機基;
【化7】
(式中,Z係選自
中任何一個的2價有機基;n係0或1;而且,R5
、R6
各為碳數1~4之烷基或烷氧基,可互相不同或相同;k為0、1、2中任何一個)
【化9】
(式中,V係選自下述所示之任何一個2價有機基;p係0或1;而且,R7
、R8
各為碳數1~4之烷基或烷氧基,可互相不同或相同;h為0、1、2中任何一個)
【化10】
申請專利範圍第2項:如申請專利範圍第1項之高分子化合物,其中X為以一般式(2)所示之2價有機基,Y為以式(3)所示之2價有機基。
申請專利範圍第3項:如申請專利範圍第1或2項之高分子化合物,其於上述一般式(1)中,0.05≦c/(a+b+c+d)≦0.5。
申請專利範圍第4項:如申請專利範圍第1~3項之高分子化合物,其於上述一般式(1)中,0.05≦d/(a+b+c+d)≦0.5。
申請專利範圍第5項:如申請專利範圍第1項之高分子化合物,其於上述一般式(1)中,0.05≦c/(a+b+c+d)≦0.3。
申請專利範圍第6項:如申請專利範圍第1項之高分子化合物,其於上述一般式(1)中,0.05≦d/(a+b+c+d)≦0.3。
申請專利範圍第7項:光硬化性樹脂組成物,其特徵為含有
(A)申請專利範圍第1~6項中任一項之高分子化合物,
(B)選自藉由甲醛水或甲醛水-醇改性的胺基縮合物、及在1分子中平均具有2個以上之羥甲基或烷氧基羥甲基之酚化合物中任何1種以上之交聯劑,
(C)藉由波長190~500nm之光進行分解,產生酸之光酸產生劑,
(D)溶劑。
申請專利範圍第8項:如申請專利範圍第7項之光硬化性樹脂組成物,其尚含有(E)鹼性化合物。
申請專利範圍第9項:一種圖型形成方法,其特徵為含有
(i)使用申請專利範圍第7或8項之光硬化性樹脂組成物,在基板上形成該組成物之皮膜的步驟,
(ii)經由光罩,以波長190~500nm之光進行曝光的步驟,
(iii)進行曝光後之加熱處理後,以顯像液進行顯像的步驟。
申請專利範圍第10項:如申請專利範圍第9項之圖型形成方法,其尚含有(iv)使藉由顯像形成圖型的皮膜在100~250℃間之溫度下進行後硬化的步驟。
申請專利範圍第11項:一種電氣‧電子零件用保護皮膜,其特徵為藉由申請專利範圍第9或10項之圖型形成方法所得的硬化皮膜所形成。
藉由使用本發明之含環氧基的高分子化合物,製造在寬廣波長範圍之光,經過寬闊膜厚可進行微細圖型之光硬化性樹脂組成物。另外,上述光硬化性樹脂組成物,藉由光形成圖型後,即使在低溫下被後硬化時,所形成的皮膜之特性對基板之密接性、機械強度、電絕緣性及對焊接助劑液之藥品耐性優異。而且,在半導體元件中使用上述皮膜時,藉由溫度循環之信賴性試驗時,藉由應力以防止產生破裂的效果優異。因此,適合使用於形成電子零件,例如包含發光‧受光元件等之半導體元件或電氣‧電子零件用電路基板之絕緣層、接著層用各種保護膜。
本發明之含環氧基的高分子化合物,特徵為具有以下述一般式(1)所示之重複單位的重量平均分子量為3,000~500,000的高分子化合物。
【化11】
式中,R1
~R4
係表示相同或不同的碳數1~8(較佳者為1~6)之1價烴基。具體而言,例如甲基、乙基、丙基、異丙基、正丁基、第3-丁基、環己基等之直鏈狀、支鏈狀或環狀烷基、乙烯基、烯丙基、丙烯基、丁烯基、己烯基、環己烯基等之直鏈狀、支鏈狀或環狀烯基、苯基、甲苯基等之芳基、苯甲基、苯乙基等之芳烷基等。
此外,就下述之交聯劑及光酸產生劑的相溶性及光硬化性而言,m為1~100、較佳者為1~80之整數。而且,對基板之密接性、電性特性、信賴性而言,a、b、c、d為0或正數,惟c及d不可同時為0,且0<(c+d)/(a+b+c+d)≦1.0,較佳者0.1≦(c+d)/(a+b+c+d)≦0.5,更佳者0.15≦(c+d)/(a+b+c+d)≦0.25。
此時,以0.05≦c/(a+b+c+d)≦0.5較佳,以0.05≦c/(a+b+c+d)≦0.3更佳,以0.05≦c/(a+b+c+d)≦0.15尤佳,以0.05≦d/(a+b+c+d)≦0.5較佳,以0.05≦d/(a+b+c+d)≦0.3更佳,以0.1≦d/(a+b+c+d)≦0.2尤佳。而且,a+b+c+d=1,a+b為殘餘部分,惟a,b中之任何一個可為0。
另外,X、Y係各選自以下述一般式(2)或(3)所示之具有酚性羥基的2價芳香族基,惟本發明之高分子化合物至少具有1個以式(3)所示之2價有機基。此時,以X為式(2)、Y為式(3)較佳。
【化12】
(式中,Z係選自
【化13】
中任何一個的2價有機基;n係0或1;而且,R5
、R6
各為碳數1~4之烷基或烷氧基,可互相不同或相同;k為0、1、2中任何一個)R5
、R6
之具體例,如甲基、乙基、異丙基、第3-丁基、甲氧基、乙氧基、異丙氧基等。
【化14】
(式中,V係選自下述所示之任何一個2價有機基;p係0或1;而且,R7
、R8
各為碳數1~4之烷基或烷氧基,可互相不同或相同;h為0、1、2中任何一個)
【化15】
R7
、R8
之具體例,如與R5
、R6
相同者。
本發明之含有矽伸苯樹脂骨架之高分子化合物的重量平均分子量,就使用該物之光硬化性樹脂組成物之相溶性及光硬化性,且由上述組成物所成的硬化物之機械特性而言,為3,000~500,000,較佳者為5,000~300,000。而且,重量平均分子量係藉由凝膠滲透色層分析法(GPC)之聚苯乙烯換算值。
本發明之具有矽伸苯樹脂骨架之高分子化合物,可藉由使下述式(4)之氫矽伸苯(1,4-雙(二甲基甲矽烷基)苯)、或該氫矽伸苯樹脂及下述一般式(5)之二氫有機基矽氧烷與下述一般式(6)所示之具有二烯丙基的特定含環氧基之化合物以及視其所需以下述一般式(7)所示具二烯丙基之特定酚化合物,在觸媒存在下進行所謂的「氫甲矽烷基反應」聚合反應予以製造。
【化16】
【化17】
(式中,R3
、R4
及m,與上述相同)。
【化18】
(式中,V、R7
、R8
、p、h,與上述相同)。
【化19】
(式中,Z、R5
、R6
、n、k,與上述相同)。
而且,本發明之具有式(1)所示重複單位之含環氧基的高分子化合物之重量平均分子量,可藉由調整上述式(6)及上述式(7)所示之酚化合物的烯丙基總數與上述式(4)所示氫矽伸苯樹脂、或該氫矽伸苯樹脂與上述式(5)所示之二氫有機基矽氧烷之氫甲矽烷基總數的比例(烯丙基總數/氫甲矽烷基總數)容易控制。另外,於上述二烯丙基苯酚化合物與氫矽伸苯樹脂及二氫有機基矽氧烷聚合時,可藉由使用如O-烯丙基苯酚之單烯丙基化合物、或如三乙基氫矽烷之單氫矽烷或單氫矽氧烷作為分子量調整劑,容易控制上述重量平均分子量。
於上述聚合反應中,觸媒例如鉑(含鉑黑)、銠、鈀等之鉑族金屬單體;H2
PtCl4
‧xH2
O、H2
PtCl6
‧xH2
O、NaHPtCl6
‧xH2
O、KHPtCl6
‧xH2
O、Na2
PtCl6
‧xH2
O、K2
PtCl4
‧xH2
O、PtCl4
‧xH2
O、PtCl2
、Na2
HPtCl4
‧xH2
O(式中,x以0~6之整數較佳、更佳者為0或6)等之氯化鉑、氯化鉑酸及氯化鉑酸鹽;醇改性氯化鉑酸(美國專利第3,220,972號說明書);氯化鉑酸與烯烴之錯合物(美國專利第3,159,601號說明書、美國專利第3,159,662號說明書、美國專利第3,775,452號說明書);將鉑黑或鈀等之鉑族金屬載負於氧化鋁、二氧化矽、碳等之載體上者;銠-烯烴錯合物;氯化參(三苯基膦)銠(所謂威爾金森(Wilkinson)觸媒);氯化鉑、氯化鉑酸或氯化鉑酸鹽與含乙烯基之矽氧烷(特別是含乙烯基之環狀矽氧烷)之錯合物等。
該使用量為觸媒量,通常鉑族金屬相對於反應聚合物之總量以0.001~0.1質量%較佳。
於上述聚合反應中,視其所需亦可使用溶劑。溶劑例如以甲苯、二甲苯等之碳化氫系溶劑較佳。
上述聚合條件,就不會使觸媒失活且可在短時間內完成聚合反應而言,聚合溫度例如40~150℃,特別是以60~120℃較佳。
此外,聚合時間係視聚合物之種類及量而定,為防止聚合系中濕氣介入時,以約0.5~100小時(特別是0.5~30小時)以內完成者較佳。如此使聚合反應完成後,於使用溶劑時,可藉由餾去該物,製得本發明以式(1)所示之含環氧基的高分子化合物。
其次,說明有關本發明之光硬化性樹脂組成物。本發明之光硬化性樹脂組成物,係含有(A)具有以上述一般式(1)所示之重複單位的含環氧基之高分子化合物,(B)選自藉由甲醛水或甲醛水-醇改性的胺基縮合物、及在1分子中平均具有2個以上羥甲基或烷氧基羥甲基之酚化合物中任何1種以上之交聯劑,(C)藉由波長190~500nm之光進行分解,產生酸之光酸產生劑,(D)溶劑,並且視需要含有(E)鹼性化合物。
(B)成分之交聯劑,係為引起與上述高分子化合物之硬化反應,容易形成圖型時之成份,同時更為提高硬化物之強度者。該交聯劑就光硬化性及耐熱性而言,重量平均分子量為150~10,000,特別是以200~3,000較佳。
上述交聯劑,可使用選自胺基縮合物、酚化合物中至少一種以上。此處,胺基縮合物例如藉由甲醛水或甲醛水-醇改性的蜜胺縮合物、或藉由甲醛水或甲醛水-醇改性的尿素縮合物。上述改性蜜胺縮合物之調製,例如首先以習知的方法為基準,使蜜胺單體以甲醛水進行羥甲基化予以改性,或再使該物以醇進行烷氧基化予以改性,形成以下述一般式(8)所示之改性蜜胺。而且,上述醇以低元醇、例如碳數1~4之醇較佳。
【化20】
(式中,R9
可為相同或不相同的羥甲基、含碳數1~4之烷氧基的烷氧基甲基或氫原子,至少1個為羥甲基或上述烷氧基甲基)
上述R9
例如羥甲基、甲氧基甲基、乙氧基甲基等之烷氧基甲基及氫原子等。
上述一般式(8)之改性蜜胺,具體例如三甲氧基甲基單羥甲基蜜胺、二甲氧基甲基單羥甲基蜜胺、三羥甲基蜜胺、六羥甲基蜜胺、六甲氧基羥甲基蜜胺等。
其次,使一般式(8)之改性蜜胺或該多聚物(例如二聚物、三聚物等之低聚物)以常法為基準,與甲醛加成縮聚合至企求的分子量為止,製得藉由甲醛水或甲醛水與醇改性的蜜胺縮合物。
而且,藉由甲醛水或甲醛水-醇改性的尿素縮合物之調製,例如以習知的方法為基準,使企求之分子量之尿素縮合以甲醛水進行羥甲基化予以改性,或再使該物以醇進行烷氧基化予以改性。
上述改性尿素縮合物之具體例,如甲氧基甲基化尿素縮合物、乙氧基甲基化尿素縮合物、丙氧基甲基化尿素縮合物等。
而且,可以單獨或兩者混合使用1種以上之此等改性蜜胺縮合物及改性尿素縮合物作為交聯劑。
另外,在1分子中平均具有2個以上之羥甲基或烷氧基羥甲基之酚化合物,例如(2-羥基-5-甲基)-1,3-苯二甲醇、2,2’,6,6’-四甲氧基甲基雙酚A等。
此外,可使用1種以上之此等酚化合物作為交聯劑。
而且,亦可單獨使用胺基縮合物或酚化合物或混合兩者使用作為交聯劑。
本發明之交聯劑的配合量,就光硬化性樹脂組成物中之環氧基的比例及曝光時之硬化性而言,相對於100質量份上述含環氧基之高分子化合物為0.5~50質量份,特別是以1~30質量份較佳。
(C)成分之光酸產生劑,例如藉由190~500nm之波長的光照射而產生酸,且以該物形成硬化觸媒者。本發明之光硬化性樹脂組成物,由於與酸產生劑之相溶性優異,可使用作為廣泛範圍之酸產生劑。該光酸產生劑例如鎓鹽、二偶氮甲烷衍生物、乙二肟衍生物、β-酮碸衍生物、二碸衍生物、硝基苯甲基磺酸酯衍生物、磺酸酯衍生物、醯亞胺基磺酸酯衍生物、肟磺酸酯衍生物、亞胺基磺酸酯衍生物、三嗪衍生物等。
上述鎓鹽例如以下述一般式(9)所示之化合物。
(R10
)h
M+
K-
(9)
(式中,R10
係表示可具有取代基之碳數1~12的直鏈狀、支鏈狀或環狀烷基、碳數6~12之芳基或碳數7~12之芳烷基,M+
係表示碘鎓鹽或鎏鹽,K-
係表示非求核性對向離子,h係表示2或3)。
於上述R10
中,烷基例如甲基、乙基、丙基、丁基、環己基、2-氧化環己基、正冰片基、金剛烷基等。而且,芳基例如苯基;o-、m-或p-甲氧基苯基、乙氧基苯基、m-或p-第3-丁氧基苯基等之烷氧基苯基;2-、3-或4-甲基苯基、乙基苯基、4-第3-丁基苯基、4-丁基苯基、二甲基苯基等之烷基苯基等。此外,芳烷基例如苯甲基、苯乙基等之各基。
K-
之非求核性對向離子,例如氯化物離子、溴化物離子等之鹵化物離子;三氟酸酯、1,1,1-三氟化乙烷磺酸酯、九氟化丁烷磺酸酯等之氟化烷基磺酸酯;甲苯酸酯、苯磺酸酯、4-氟化苯磺酸酯、1,2,3,4,5-五氟化苯磺酸酯等之芳基磺酸酯;甲磺酸酯、丁烷磺酸酯等之烷基磺酸酯等。
二偶氮甲烷衍生物,例如以下述一般式(10)所示之化合物。
【化21】
(式中,R11
係表示相同或不同的碳數1~12之直鏈狀、支鏈狀或環狀烷基或鹵化烷基、碳數6~12之芳基或鹵化芳基、或碳數7~12之芳烷基)。
於上述R11
中,烷基例如甲基、乙基、丙基、丁基、戊基、環戊基、環己基、正冰片基、金剛烷基等。鹵化烷基例如三氟化甲基、1,1,1-三氟化乙基、1,1,1-三氯化乙基、九氟化丁基等。芳基例如苯基;o-、m-或p-甲氧基苯基、乙氧基苯基、m-或p-第3-丁氧基苯基等之烷氧基苯基;2-、3-或4-甲基苯基、乙基苯基、4-第3-丁基苯基、4-丁基苯基、二甲基苯基等之烷基苯基等。鹵化芳基例如氟化苯基、氯化苯基、1,2,3,4,5-五氟化苯基等。芳烷基例如苯甲基、苯乙基等。
具體而言,光酸產生劑例如三氟化甲烷磺酸二苯基碘鎓鹽、三氟化甲烷磺酸(p-第3-丁氧基苯基)苯基碘鎓鹽、p-甲苯磺酸二苯基碘鎓鹽、p-甲苯磺酸(p-第3-丁氧基苯基)苯基碘鎓鹽、三氟化甲烷磺酸三苯基磺醯酯、三氟化甲烷磺酸(p-第3-丁氧基苯基)二苯基鎏、三氟化甲烷磺酸雙(p-第3-丁氧基苯基)苯基鎏、三氟化甲烷磺酸參(p-第3-丁氧基苯基)鎏、p-甲苯磺酸三苯基鎏、p-甲苯磺酸(p-第3-丁氧基苯基)二苯基鎏、p-甲苯磺酸雙(p-第3-丁氧基苯基)苯基鎏、p-甲苯磺酸參(p-第3-丁氧基苯基)鎏、九氟化丁烷磺酸三苯基鎏、丁烷磺酸三苯基鎏、三氟化甲烷磺酸三甲基鎏、p-甲苯磺酸三甲基鎏、三氟化甲烷磺酸環己基甲基(2-氧化環己基)鎏、p-甲苯磺酸環己基甲基(2-氧化環己基)鎏、三氟化甲烷磺酸二甲基苯基鎏、p-甲苯磺酸二甲基苯基鎏、三氟化甲烷磺酸二環己基苯基鎏、p-甲苯磺酸二環己基苯基鎏、二苯基(4-硫化苯氧基苯基)六氟化銻酸鎏鹽等之鎓鹽;雙(苯磺醯基)二偶氮甲烷、雙(p-甲苯磺醯基)二偶氮甲烷、雙(二甲苯磺醯基)二偶氮甲烷、雙(環己基磺醯基)二偶氮甲烷、雙(環戊基磺醯基)二偶氮甲烷、雙(n-丁基磺醯基)二偶氮甲烷、雙(異丁基磺醯基)二偶氮甲烷、雙(第2-丁基磺醯基)二偶氮甲烷、雙(n-丙基磺醯基)二偶氮甲烷、雙(異丙基磺醯基)二偶氮甲烷、雙(第3-丁基磺醯基)二偶氮甲烷、雙(n-戊基磺醯基)二偶氮甲烷、雙(異戊基磺醯基)二偶氮甲烷、雙(第2-戊基磺醯基)二偶氮甲烷、雙(第3-戊基磺醯基)二偶氮甲烷、1-環己基磺醯基-1-(第3-丁基磺醯基)二偶氮甲烷、1-環己基磺醯基-1-(第3-戊基磺醯基)二偶氮甲烷、1-第3-戊基磺醯基-1-(第3-丁基磺醯基)二偶氮甲烷等之二偶氮甲烷衍生物;雙-o-(p-甲苯磺醯基)-α-二甲基乙二肟、雙-o-(p-甲苯磺醯基)-α-二苯基乙二肟、雙-o-(p-甲苯磺醯基)-α-二環己基乙二肟、雙-o-(p-甲苯磺醯基)-2,3-戊二酮乙二肟、雙(p-甲苯磺醯基)-2-甲基-3,4-戊二酮乙二肟、雙-o-(n-丁烷磺醯基)-α-二甲基乙二肟、雙-o-(n-丁烷磺醯基)-α-二苯基乙二肟、雙-o-(n-丁烷磺醯基)-α-二環己基乙二肟、雙-o-(n-丁烷磺醯基)-2,3-戊二酮乙二肟、雙-o-(n-丁烷磺醯基)-2-甲基-3,4-戊二酮乙二肟、雙-o-(甲烷磺醯基)-α-二甲基乙二肟、雙-o-(三氟化甲烷磺醯基)-α-二甲基乙二肟、雙-o-(1,1,1-三氟化乙烷磺醯基)-α-二甲基乙二肟、雙-o-(第3-丁烷磺醯基)-α-二甲基乙二肟、雙-o-(全氟化辛烷磺醯基)-α-二甲基乙二肟、雙-o-(環己烷磺醯基)-α-二甲基乙二肟、雙-o-(苯磺醯基)-α-二甲基乙二肟、雙-o-(p-氟化苯磺醯基)-α-二甲基乙二肟、雙-o-(p-第3-丁基苯磺醯基)-α-二甲基乙二肟、雙-o-(二甲苯磺醯基)-α-二甲基乙二肟、雙-o-(樟腦磺醯基)-α-二甲基乙二肟等之乙二肟衍生物;α-(苯磺醯氧基亞胺基)-4-甲基苯基乙腈等之肟磺酸酯衍生物;2-環己基羰基-2-(p-甲苯磺醯基)丙烷、2-異丙基羰基-2-(p-甲苯磺醯基)丙烷等之β-酮碸衍生物;二苯基二碸、二環己基二碸等之二碸衍生物;p-甲苯磺酸2,6-二硝基苯甲基、p-甲苯磺酸2,4-二硝基苯甲基等之硝基苯甲基磺酸酯衍生物;1,2,3-參(甲烷磺醯氧基)苯、1,2,3-參(三氟化甲烷磺醯氧基)苯、1,2,3-參(p-甲苯磺醯氧基)苯等之磺酸酯衍生物;酞醯亞胺基-三氟酸酯、酞醯亞胺基-對甲苯磺酸酯、5-正冰片烯-2,3-二羧基醯亞胺基-三氟酸酯、5-正冰片基-2,3-二羧基醯亞胺基-對甲苯磺酸酯、5-正冰片基-2,3-二羧基醯亞胺基-n-丁基磺酸酯、n-三氟化甲基磺醯氧基萘基醯亞胺等之醯亞胺基-磺酸酯衍生物等。
另外,例如(5-(4-甲基苯基)磺醯氧基亞胺基-5H-噻吩-2-次基)-(2-甲基苯基)乙腈、(5-(4-(4-甲基苯基磺醯氧基)苯基磺醯氧基亞胺基)-5H-噻吩-2-次基)-(2-甲基苯基)-乙腈等之亞胺基磺酸酯、2-甲基-2-[(4-甲基苯基)磺醯基]-1-[(4-甲基硫代)苯基]-1-丙烷等。於此等中,以使用醯亞胺基-磺酸酯類、亞胺基磺酸酯類、肟磺酸酯類等較佳。
上述光酸產生劑、可單獨使用1種或2種以上混合使用。
上述光酸產生劑之配合量,就光酸產生劑本身之光吸收及膜厚之光硬化性而言,相對於100質量份含環氧基之高分子化合物為0.05~20質量份、較佳者為0.2~5質量份。
(D)成分之溶劑,必須可溶解上述高分子化合物、藉由甲醛水或甲醛水-醇改性的胺基縮合物、酚化合物、環氧基化合物及光酸產生劑等之成份。
例如環己酮、環戊酮、甲基-2-n-戊酮等之酮類;3-甲氧基丁醇、3-甲基-3-甲氧基丁酮、1-甲氧基-2-丙醇、1-乙氧基-2-丙醇等之醇類;丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇二甲醚、二乙二醇二甲醚等之醚類;丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、乳酸乙酯、丙酮酸乙酯、醋酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、醋酸第3-丁酯、丙酸第3-丁酯、丙二醇單第3-丁醚乙酸酯、γ-丁內酯等之酯類,此等可單獨使用或2種以上併用。
於此等之中,特別是以光酸產生劑之溶解性最為優異的乳酸乙酯、環己酮、環戊酮、丙二醇單甲醚乙酸酯、γ-丁內酯或此等之混合溶劑較佳。
上述溶劑之配合量,就光硬化性樹脂組成物之相溶性、黏度及塗佈性而言,相對於100質量份(A)~(C)成分之全部固成分為50~2,000質量份,尤以100~1,000質量份較佳。
另外,本發明視其所需可添加鹼性化合物作為(E)成分。該鹼性化合物,以可抑制藉由光酸產生劑產生的酸在光阻膜中擴散時之擴散速度之化合物為宜。其次,藉由配合該鹼性化合物,可抑制光阻膜中酸之擴散速度,提高解像度,且抑制曝光後之感度變化,基板或環境相關性變小,提高曝光充分度或圖型外型等。
該鹼性化合物例如一級、二級、三級之脂肪族胺類、混成胺類、芳香族胺類、雜環胺類、具有羧基之含氮化合物、具有磺醯基之含氮化合物、具有羥基之含氮化合物、具有羥基苯基之含氮化合物、醇性含氮化合物、醯胺衍生物、醯亞胺衍生物以及以下述一般式(11)所示之化合物等。
N(Z)n
(Y)3-n
(11)
式中,n=1,2或3。側鏈Z可為相同或不同的以下述一般式(12)~(14)所示之任何一個取代基。側鏈Y可為相同或不同的氫原子、或直鏈狀、支鏈狀或環狀碳數1~20之烷基,亦可含有醚基或羥基。而且,側鏈Z間可鍵結形成環。
【化22】
此處,R300
、R302
、R305
為碳數1~4之直鏈狀或支鏈狀亞烷基,R301
、R304
為氫原子或碳數1~20之直鏈狀、支鏈狀或環狀烷基,亦可含有1個或複數個羥基、醚基、酯基、內酯環。R303
為單鍵或碳數1~4之直鏈狀或支鏈狀之亞烷基,R306
為碳數1~20之直鏈狀、支鏈狀或環狀烷基,亦可含有1個或複數個羥基、醚基、酯基、內酯環。
具體而言,一級脂肪族胺類例如銨、甲胺、乙胺、正丙胺、異丙胺、正丁胺、異丁胺、第2-丁胺、第3-丁胺、戊胺、第3-戊胺、環戊胺、己胺、環己胺、庚胺、辛胺、壬胺、癸胺、十二烷胺、十六烷胺、甲二胺、乙二胺、四伸乙基戊胺等。
二級脂肪族胺類例如二甲胺、二乙胺、二正丙胺、二異丙胺、二正丁胺、二異丁胺、二-第2-丁胺、二戊胺、二環戊胺、二己胺、二環己胺、二庚胺、二辛胺、二壬胺、二癸胺、二-十二烷胺、二-十六烷胺、N,N-二甲基甲二胺、N,N-二甲基乙二胺、N,N-二甲基四伸乙基戊胺等。
三級脂肪族胺類例如三甲胺、三乙胺、三正丙胺、三異丙胺、三正丁胺、三異丁胺、三-第2-丁胺、三戊胺、三環戊胺、三己胺、三環己胺、三庚胺、三辛胺、三壬胺、三癸胺、三-十二烷胺,三-十六烷胺、N,N,N’,N’-四甲基甲二胺、N,N,N’,N’-四甲基乙二胺、N,N,N’,N’-四甲基四伸乙基戊胺等。
而且,混合胺類例如二甲基乙胺、甲基乙基丙胺、苯甲胺、苯乙胺、苯甲基二甲胺等。
芳香族胺類及雜環胺類之具體例,如苯胺衍生物(例如苯胺、N-甲基苯胺、N-乙基苯胺、N-丙基苯胺、N,N-二甲基苯胺、2-甲基苯胺、3-甲基苯胺、4-甲基苯胺、乙基苯胺、丙基苯胺、三甲基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2,4-二硝基苯胺、2,6-二硝基苯胺、3,5-二硝基苯胺、N,N-二甲基甲苯胺等)、二苯基(p-甲苯基)胺、甲基二苯胺、三苯胺、苯二胺、萘胺、二胺基萘、吡咯衍生物(例如吡咯、2H-吡咯、1-甲基吡咯、2,4-二甲基吡咯、2,5-二甲基吡咯、N-甲基吡咯等)、噁唑衍生物(例如噁唑、異噁唑等)、噻唑衍生物(例如噻唑、異噻唑等)、咪唑衍生物(例如咪唑、4-甲基咪唑、4-甲基-2-苯基咪唑等)、吡唑衍生物、呋咱衍生物、吡咯啉衍生物(例如吡咯啉、2-甲基-1-吡咯啉等)、吡咯烷衍生物(例如吡咯烷、N-甲基吡咯烷、四氫咯酮、N-甲基吡咯烷酮等)、咪唑啉衍生物、咪唑嗪衍生物、吡啶衍生物(例如吡啶、甲基吡啶、乙基吡啶、丙基吡啶、丁基吡啶、4-(1-丁基戊基)吡啶、二甲基吡啶、三甲基吡啶、三乙基吡啶、苯基吡啶、3-甲基-2-苯基吡啶、4-第3-丁基吡啶、二苯基吡啶、苯甲基吡啶、甲氧基吡啶、丁氧基吡啶、二甲氧基吡啶、1-甲基-2-吡啶、4-吡咯烷吡啶、1-甲基-4-苯基吡啶、2-(1-乙基丙基)吡啶、胺基吡啶、二甲基胺基吡啶等)、噠嗪衍生物、嘧啶衍生物、吡嗪衍生物、吡唑啉衍生物、吡唑烷衍生物、哌啶衍生物、哌嗪衍生物、嗎啉衍生物、吲哚衍生物、異吲哚衍生物、1H-咪唑衍生物、吲唑啉衍生物、喹啉衍生物(例如喹啉衍生物、3-喹啉羰腈等)、異喹啉衍生物、噌啉衍生物、喹唑啉衍生物、喹喔啉衍生物、酞嗪衍生物、卜啉衍生物、蝶啶衍生物、咔唑衍生物、菲啶衍生物、吖嗪衍生物、吩嗪衍生物、1,10-菲繞啉衍生物、腺嘌呤衍生物、腺苷衍生物、鳥嘌呤衍生物、鳥苷衍生物、尿嘧啶衍生物、尿苷衍生物等。
具有羧基之含氮化合物,例如胺基苯甲酸、吲哚羧酸、胺基酸衍生物(例如煙鹼酸、丙胺酸、精胺酸、天冬胺酸、谷胺酸、甘胺酸、組胺酸、異亮胺酸、甘胺醯亮胺酸、亮胺酸、蛋胺酸、苯基苯胺、蘇胺酸、賴胺酸、3-胺基吡嗪-2-羧酸、甲氧基苯胺等)。
具有磺醯基之含氮化合物,例如3-吡啶磺酸、p-甲苯磺酸吡錠鹽等。
具有羥基之含氮化合物、具有羥基苯基之含氮化合物、醇性含氮化合物,例如2-羥基吡啶、胺基甲酚、2,4-喹啉二醇、3-吲哚甲醇氫化物、單乙醇胺、二乙醇胺、三乙醇胺、N-乙基二乙醇胺、N,N-二乙基乙醇胺、三異丙醇胺、2,2’-亞胺基二乙醇、2-胺基乙醇、3-胺基-1-丙醇、4-胺基-1-丁醇、4-(2-羥基乙基)嗎啉、2-(2-羥基乙基)吡啶、1-(2-羥基乙基)哌嗪、1-[2-(2-羥基乙氧基)乙基]哌嗪、哌啶乙醇、1-(2-羥基乙基)吡咯烷、1-(2-羥基乙基)-2-四氫咯酮、3-哌啶基-1,2-丙烷二醇、3-吡咯烷基-1,2-丙烷二醇、8-羥基久洛尼定、3-喹核醇、3-托品醇、1-甲基-2-吡咯烷乙醇、1-吖啶乙醇、N-(2-羥基乙基)酞醯亞胺、N-(2-羥基乙基)異煙鹼醯胺等。
醯胺衍生物例如甲醯胺、N-甲基甲醯胺、N,N-二甲基甲醯胺、乙醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、丙醯胺、苯甲醯胺等。
醯亞胺衍生物例如酞醯亞胺、琥珀醯亞胺、馬來醯亞胺等。
上述一般式(11)所示之化合物,例如參[2-(甲氧基甲氧基)乙基]胺、參[2-(2-甲氧基乙氧基)乙基]胺、參[2-(2-甲氧基乙氧基甲氧基)乙基]胺、參[2-(1-甲氧基乙氧基)乙基]胺、參[2-(1-乙氧基乙氧基)乙基]胺、參[2-(1-乙氧基丙氧基)乙基]胺、參[2-{2-(2-羥基乙氧基)乙氧基}乙基]胺、4,7,13,16,21,24-六氧-1,10-二氮雜二環[8.8.8]二十六烷、4,7,13,18-四氧-1,10-二氮雜二環[8.5.5]二十烷、1,4,10,13-四氧-7,16-二氮雜二環十八烷、1-氮雜-12-冠-4、1-氮雜-15-冠-5、1-氮雜-18-冠-6、參(2-甲醯氧基乙基)胺、參(2-乙醯氧基乙基)胺、參(2-丙醯氧基乙基)胺、參(2-丁醯氧基乙基)胺、參(2-異丁醯氧基乙基)胺、參(2-戊醯氧基乙基)胺、參(2-三甲基乙醯氧基乙基)胺、N,N-雙(2-乙醯氧基乙基)-2-(乙醯氧基乙醯氧基)乙胺、參(2-甲氧基羰氧基乙基)胺、參(2-第3-丁氧基羰氧基乙基)胺、參[2-(2-氧代丙氧基)乙基]胺、參[2-(甲氧基羰基甲基)氧化乙基]胺、參[2-(第3-丁氧基羰基甲基氧化)乙基]胺、參[2-(環己基氧化羰基甲基氧化)乙基]胺、參(2-甲氧基羰基乙基)胺、參(2-乙氧基羰基乙基)胺、N,N-雙(2-羥基乙基)-2-(甲氧基羰基)乙胺、N,N-雙(2-乙醯氧基乙基)-2-(甲氧基羰基)乙胺、N,N-雙(2-羥基乙基)-2-(乙氧基羰基)乙胺、N,N-雙(2-乙醯氧基乙基)-2-(乙氧基羰基)乙胺、N,N-雙(2-羥基乙基)-2-(2-甲氧基乙氧基羰基)乙胺、N,N-雙(2-乙醯氧基乙基)-2-(2-甲氧基乙氧基羰基)乙胺、N,N-雙(2-羥基乙基)-2-(2-羥基乙氧基羰基)乙胺、N,N-雙(2-乙醯氧基乙基)-2-(2-乙醯氧基乙氧基羰基)乙胺、N,N-雙(2-羥基乙基)-2-[(甲氧基羰基)甲氧基羰基]乙胺、N,N-雙(2-乙醯氧基乙基)-2-[(甲氧基羰基)甲氧基羰基]乙胺、N,N-雙(2-羥基乙基)-2-(2-氧代丙氧基羰基)乙胺、N,N-雙(2-乙醯氧基乙基)-2-(2-氧代丙氧基羰基)乙胺、N,N-雙(2-羥基乙基)-2-(四氫呋喃基氧化羰基)乙胺、N,N-雙(2-乙醯氧基乙基)-2-(四氫呋喃基氧化羰基)乙胺、N,N-雙(2-羥基乙基)-2-[(2-氧化四氫呋喃-3-基)氧化羰基]乙胺、N,N-雙(2-乙醯氧基乙基)-2-[(2-氧化四氫呋喃-3-基)氧化羰基]乙胺、N,N-雙(2-羥基乙基)-2-(4-羥基丁氧基羰基)乙胺、N,N-雙(2-甲醯氧基乙基)-2-(4-甲醯氧基丁氧基羰基)乙胺、N,N-雙(2-甲醯氧基乙基)-2-(2-甲醯氧基乙氧基羰基)乙胺、N,N-雙(2-甲氧基乙基)-2-(甲氧基羰基)乙胺、N-(2-羥基乙基)雙[2-(甲氧基羰基)乙基]胺、N-(2-乙醯氧基乙基)雙[2-(甲氧基羰基)乙基]胺、N-(2-羥基乙基)雙[2-(乙氧基羰基)乙基]胺、N-(2-乙醯氧基乙基)雙[2-(乙氧基羰基)乙基]胺、N-(3-羥基-1-丙基)雙[2-(甲氧基羰基)乙基]胺、N-(3-乙醯氧基-1-丙基)雙[2-(甲氧基羰基)乙基]胺、N-(2-甲氧基乙基)雙[2-(甲氧基羰基)乙基]胺、N-丁基雙[2-(甲氧基羰基)乙基]胺、N-丁基雙[2-(2-甲氧基乙氧基羰基)乙基]胺、N-甲基雙(2-乙醯氧基乙基)胺、N-乙基雙(2-乙醯氧基乙基)胺、N-甲基雙(2-三甲基乙醯氧基乙基)胺、N-乙基雙[2-(甲氧基羰基氧化)乙基]胺、N-乙基雙[2-(第3-丁氧基羰基氧化)乙基]胺、參(甲氧基羰基甲基)胺、參(乙氧基羰基甲基)胺、N-丁基雙(甲氧基羰基甲基)胺、N-己基雙(甲氧基羰基甲基)胺、β-(二乙基胺基)-δ-戊內酯,惟不受此等所限制。
而且,上述鹼性化合物可單獨1種或2種以上組合使用,其配合量就感度而言,相對於100質量份上述含環氧基之高分子化合物為0~3質量份,尤其是以0.01~1質量份較佳。
另外,本發明之光硬化性樹脂組成物中,除上述各成分外,尚可配合添加成分。該添加成分例如為提高塗佈性時慣用的界面活性劑及光酸發生劑等之為提高光吸收效率時慣用的吸光劑。
界面活性劑以非離子性者較佳,例如氟系界面活性劑,具體而言例如全氟化烷基聚氧化乙烯乙醇、氟化烷酯、全氟化烷基氧化胺、含氟有機基聚矽氧烷系化合物等。
此等可使用市售品,例如Fluorad「FC-4430」(SUMITOMO 3M(股)製)、SAFLON「S-141」及「S-145」(皆為旭硝子(股)製)、Unidain「DS-401」、「DS-4031」及「DS-451」(皆為Daikin工業(股)製)、Megafac「F-8151」(DIC(股)製)、「X-70-093」(信越化學工業(股)製)等。於此等中,較佳者為Fluorad「FC-4430」(SUMITOMO 3M(股)製)及「X-70-093」(信越化學工業(股)製)。
吸光劑例如二芳基亞碸、二芳基碸、9,10-二甲基蒽、9-芴酮等。
調製本發明之光硬化性樹脂組成物時,可以一般的方法進行,使上述各成份及視其所需上述溶劑、添加劑等進行攪拌混合,然後,視其所需藉由過濾器等過濾固體成分,調製本發明之光硬化性樹脂組成物。
該經調製的本發明之光硬化性樹脂組成物,例如適合使用作為半導體元件之保護膜、配線之保護膜、表層膜、焊接劑及貫通電極用絕緣膜(TSV用)、微細加工用光阻劑等之材料。
其次,說明有關使用上述光硬化性樹脂組成物之本發明圖型形成方法。
於本發明之圖型形成方法中,預先在基板上塗佈上述光硬化性樹脂組成物。上述基板例如矽晶圓、貫通電極用矽晶圓、塑膠或陶瓷製電路基板等。
塗佈法可採用習知的微影術進行。例如可藉由浸漬法、旋轉塗佈法、輥塗佈法等之方法進行塗佈處理。塗佈量可視目的而定適當選擇,膜厚為0.1~100μm,較佳者為1~100μm,更佳者為3~50μm。而且,亦可預先形成該組成物之薄膜,與基板貼合。
此處,為有效地進行光硬化反應時,視其所需藉由預備加熱(預烘烤),使溶劑等預先揮發。預備加熱例如可在40~140℃下進行約1分鐘~1小時。然後,經由光罩,以波長190~500nm進行曝光、硬化處理。上述光罩,例如可為貫穿企求的圖型者。而且,光罩之材質以遮蔽上述波長190~500nm之光者較佳,例如可使用鉻等,惟不受此等所限制。上述波長190~500nm之光,例如藉由放射線產生裝置所產生的各種波長光,例如g線、i線等之紫外線、遠紫外線(248nm、193nm)等。較佳者為248~436nm。曝光量例如10~3,000mJ/cm2
較佳。藉由該曝光處理,使曝光部分進行交聯,形成不溶於下述溶劑之不溶化圖型。
另外,為提高顯影感度時,於曝光後進行加熱處理(後曝光烘烤(以下稱為PEB))。上述曝光後之加熱處理,例如可在40~140℃下進行0.5~10分鐘。
然後,以顯影液進行顯影處理。上述顯影劑,以作為溶劑使用的溶劑系,例如IPA(異丙醇)等之醇類或環己酮等之酮類及丙二醇單甲醚等之二醇等較佳,惟亦可使用作為光硬化性樹脂組成物之溶劑使用的溶劑。顯影處理可藉由一般的方法,例如藉由浸漬圖型形成物等進行。然後,視其所需進行洗淨、沖洗、乾燥等,製得具有企求圖型之光硬化性樹脂組成物的皮膜。而且,有關圖型之形成方法如上所述,不一定必須形成圖型時,例如欲形成單純的均一皮膜時,除沒有使用上述光罩外,可以與上述圖型形成方法所述相同的方法進行。
另外,使所得的圖型使用烤箱或加熱板,在溫度100~250℃下(較佳者為150~220℃,更佳者為170~190℃)進行後硬化處理。後硬化處理溫度為100~250℃時,就可提高光硬化性樹脂組成物之皮膜的交聯密度,除去殘留的揮發成分,對基板之密接力、耐熱性或強度以及電性特性而言較佳。其次,後硬化時間可為10分鐘~10小時。
如此所得的硬化皮膜,與基板之密接性、耐熱性、電性特性、機械特性及對焊接助劑液之藥品耐性優異,以該物作為保護皮膜之半導體元件的信賴性優異,特別是可防止於溫度循環試驗時產生的破裂情形,適合作為電氣、電子零件、半導體元件等之保護皮膜。
於下述中,以合成例、實施例及比較例具體地說明本發明,惟本發明不受下述例所限制。而且,於下述例中,份係表示質量份。而且,於下述合成例中使用的化合物(M-1)~(M-7)之化學構造式如下述所示。
【化23】
在具備攪拌機、溫度計、氮氣取代裝置及回流冷卻器之5L燒瓶中,使化合物(M-1)396.9g、化合物(M-4)45.0g溶解於甲苯1,875g後,加入化合物(M-5)949.6g、化合物(M-6)6.1g,在60℃下進行加溫。然後,投入碳載負鉑觸媒(5質量%)2.2g,且確認內部反應溫度昇為65~67℃後,再於3小時內加溫至90℃,再冷卻至60℃,投入碳載負鉑觸媒(5質量%)2.2g,在1小時內、於燒瓶中滴入化合物(M-7)107.3g。此時,燒瓶內溫度上昇至78℃。滴完後,再於90℃下熟成3小時後,冷卻至室溫,且加入甲基異丁酮(MIBK)1,700g,藉由使本反應溶液以過濾器加壓過濾,去除鉑觸媒。另外,在所得的高分子化合物溶液中加入純水760g進行攪拌、靜置分液,除去下層之水層。重複進行該分液水洗操作6次,去除高分子化合物溶液中之微量酸成分。使該高分子化合物溶液中之溶劑減壓餾去,同時添加環戊酮950g,製得以固體成分濃度60質量%之環戊酮為主溶劑之高分子化合物溶液(A-1)。藉由GPC測定該高分子化合物溶液中高分子化合物之分子量時,以聚苯乙烯換算,重量平均分子量為62,000,式(1)中a為0.594、b為0.351、c為0.061、d為0.039、(c+d)/(a+b+c+d)為0.10。而且,
【化24】
在具備攪拌機、溫度計、氮氣取代裝置及回流冷卻器之5L燒瓶中,使化合物(M-1)352.8g、化合物(M-4)90.0g溶解於甲苯1,875g後,加入化合物(M-5)949.6g、化合物(M-6)6.1g,在60℃下進行加溫。然後,投入碳載負鉑觸媒(5質量%)2.2g,且確認內部反應溫度昇為65~67℃後,再於3小時內加溫至90℃,再冷卻至60℃,投入碳載負鉑觸媒(5質量%)2.2g,在1小時內、於燒瓶中滴入化合物(M-7)107.3g。此時,燒瓶內溫度上昇至79℃。滴完後,再於90℃下熟成3小時後,冷卻至室溫,且加入甲基異丁酮(MIBK)1,700g,藉由使本反應溶液以過濾器加壓過濾,去除鉑觸媒。另外,在所得的高分子化合物溶液中加入純水760g進行攪拌、靜置分液,除去下層之水層。重複進行該分液水洗操作6次,去除高分子化合物溶液中之微量酸成分。使該高分子化合物溶液中之溶劑減壓餾去,同時添加環戊酮980g,製得以固體成分濃度60質量%之環戊酮為主溶劑之高分子化合物溶液(A-2)。藉由GPC測定該高分子化合物溶液中高分子化合物之分子量時,以聚苯乙烯換算,重量平均分子量為64,000,式(1)中a為0.480、b為0.320、c為0.120、d為0.080、(c+d)/(a+b+c+d)為0.20。此外,X、Y、m與合成例1相同。
在具備攪拌機、溫度計、氮氣取代裝置及回流冷卻器之5L燒瓶中,使化合物(M-1)308.7g、化合物(M-4)135.0g溶解於甲苯1,875g後,加入化合物(M-5)949.6g、化合物(M-6)6.1g,在60℃下進行加溫。然後,投入碳載負鉑觸媒(5質量%)2.2g,且確認內部反應溫度昇為65~67℃後,再於3小時內加溫至90℃,再冷卻至60℃,投入碳載負鉑觸媒(5質量%)2.2g,在1小時內、於燒瓶中滴入化合物(M-7)107.3g。此時,燒瓶內溫度上昇至80℃。滴完後,再於90℃下熟成3小時後,冷卻至室溫,且加入甲基異丁酮(MIBK)1,700g,藉由使本反應溶液以過濾器加壓過濾,去除鉑觸媒。另外,在所得的高分子化合物溶液中加入純水760g進行攪拌、靜置分液,除去下層之水層。重複進行該分液水洗操作6次,去除高分子化合物溶液中之微量酸成分。使該高分子化合物溶液中之溶劑減壓餾去,同時添加環戊酮900g,製得以固體成分濃度60質量%之環戊酮為主溶劑之高分子化合物溶液(A-3)。藉由GPC測定該高分子化合物溶液中高分子化合物之分子量時,以聚苯乙烯換算,重量平均分子量為68,000,式(1)中a為0.420、b為0.280、c為0.180、d為0.120、(c+d)/(a+b+c+d)為0.30。此外,X、Y、m與合成例1相同。
在具備攪拌機、溫度計、氮氣取代裝置及回流冷卻器之5L燒瓶中,使化合物(M-1)220.5g、化合物(M-4)225.0g溶解於甲苯1,875g後,加入化合物(M-5)949.6g、化合物(M-6)6.1g,在60℃下進行加溫。然後,投入碳載負鉑觸媒(5質量%)2.2g,且確認內部反應溫度昇為65~67℃後,再於3小時內加溫至90℃,再冷卻至60℃,投入碳載負鉑觸媒(5質量%)2.2g,在1小時內、於燒瓶中滴入化合物(M-7)107.3g。此時,燒瓶內溫度上昇至80℃。滴完後,再於90℃下熟成3小時後,冷卻至室溫,且加入甲基異丁酮(MIBK)1,700g,藉由使本反應溶液以過濾器加壓過濾,去除鉑觸媒。另外,在所得的高分子化合物溶液中加入純水760g進行攪拌、靜置分液,除去下層之水層。重複進行該分液水洗操作6次,去除高分子化合物溶液中之微量酸成分。使該高分子化合物溶液中之溶劑減壓餾去,同時添加環戊酮950g,製得以固體成分濃度60質量%之環戊酮為主溶劑之高分子化合物溶液(A-4)。藉由GPC測定該高分子化合物溶液中高分子化合物之分子量時,以聚苯乙烯換算,重量平均分子量為75,000,式(1)中a為0.294、b為0.206、c為0.306、d為0.194、(c+d)/(a+b+c+d)為0.50。此外,X、Y、m與合成例1相同。
在具備攪拌機、溫度計、氮氣取代裝置及回流冷卻器之5L燒瓶中,使化合物(M-1)352.8g、化合物(M-3)116.1g溶解於甲苯1,875g後,加入化合物(M-5)949.6g、化合物(M-6)6.1g,在60℃下進行加溫。然後,投入碳載負鉑觸媒(5質量%)2.2g,且確認內部反應溫度昇為65~67℃後,再於3小時內加溫至90℃,再冷卻至60℃,投入碳載負鉑觸媒(5質量%)2.2g,在1小時內、於燒瓶中滴入化合物(M-7)107.3g。此時,燒瓶內溫度上昇至73℃。滴完後,再於90℃下熟成3小時後,冷卻至室溫,且加入甲基異丁酮(MIBK)1,700g,藉由使本反應溶液以過濾器加壓過濾,去除鉑觸媒。另外,在所得的高分子化合物溶液中加入純水760g進行攪拌、靜置分液,除去下層之水層。重複進行該分液水洗操作6次,去除高分子化合物溶液中之微量酸成分。使該高分子化合物溶液中之溶劑減壓餾去,同時添加環戊酮940g,製得以固體成分濃度60質量%之環戊酮為主溶劑之高分子化合物溶液(A-5)。藉由GPC測定該高分子化合物溶液中高分子化合物之分子量時,以聚苯乙烯換算,重量平均分子量為55,000,式(1)中a為0.486、b為0.314、c為0.114、d為0.086、(c+d)/(a+b+c+d)為0.20。此外,X、m與合成例1相同。Y如下所述。
【化25】
在具備攪拌機、溫度計、氮氣取代裝置及回流冷卻器之5L燒瓶中,使化合物(M-1)441.0g溶解於甲苯1,875g後,加入化合物(M-5)949.6g、化合物(M-6)6.1g,在60℃下進行加溫。然後,投入碳載負鉑觸媒(5質量%)2.2g,且確認內部反應溫度昇為65~67℃後,再於3小時內加溫至90℃,再冷卻至60℃,投入碳載負鉑觸媒(5質量%)2.2g,在1小時內、於燒瓶中滴入化合物(M-7)107.3g。此時,燒瓶內溫度上昇至78℃。滴完後,再於90℃下熟成5小時後,冷卻至室溫,且加入甲基異丁酮(MIBK)1,700g,藉由使本反應溶液以過濾器加壓過濾,去除鉑觸媒。另外,在所得的高分子化合物溶液中加入純水760g進行攪拌、靜置分液,除去下層之水層。重複進行該分液水洗操作6次,去除高分子化合物溶液中之微量酸成分。使該高分子化合物溶液中之溶劑減壓餾去,同時添加環戊酮950g,製得以固體成分濃度60質量%之環戊酮為主溶劑之高分子化合物溶液(B-1)。藉由GPC測定該高分子化合物溶液中高分子化合物之分子量時,以聚苯乙烯換算,重量平均分子量為51,000,式(1)中a為0.590、b為0.410、c為0、d為0、(c+d)/(a+b+c+d)為0。
在具備攪拌機、溫度計、氮氣取代裝置及回流冷卻器之5L燒瓶中,使化合物(M-1)225.0g、化合物(M-2)161.2g溶解於甲苯1,875g後,加入化合物(M-5)949.6g、化合物(M-6)6.1g,在60℃下進行加溫。然後,投入碳載負鉑觸媒(5質量%)2.2g,且確認內部反應溫度昇為65~67℃後,再於3小時內加溫至90℃,再冷卻至60℃,投入碳載負鉑觸媒(5質量%)2.2g,在1小時內、於燒瓶中滴入化合物(M-7)107.3g。此時,燒瓶內溫度上昇至75℃。滴完後,再於90℃下熟成5小時後,冷卻至室溫,且加入甲基異丁酮(MIBK)1,700g,藉由使本反應溶液以過濾器加壓過濾,去除鉑觸媒。另外,在所得的高分子化合物溶液中加入純水760g進行攪拌、靜置分液,除去下層之水層。重複進行該分液水洗操作6次,去除高分子化合物溶液中之微量酸成分。使該高分子化合物溶液中之溶劑減壓餾去,同時添加環戊酮900g,製得以固體成分濃度60質量%之環戊酮為主溶劑之高分子化合物溶液(B-2)。藉由GPC測定該高分子化合物溶液中高分子化合物之分子量時,以聚苯乙烯換算,重量平均分子量為53,000,式(1)中a為0.600、b為0.400、c為0、d為0、(c+d)/(a+b+c+d)為0。
使用上述合成例1~7所合成的高分子化合物之溶液,以表1記載的組成配合交聯劑、光酸發生劑、鹼性化合物、溶劑及其他添加物等,然後,進行攪拌、混合、溶解後,以鐵氟龍(註冊商標)製0.2μm過濾器進行精密過濾處理,製得實施例1~8及比較例1~4之光硬化性樹脂組成物。
其次,在無處理的6吋矽晶圓上,使用旋轉塗佈器塗佈表1記載的膜厚之各實施例及比較例的光硬化性樹脂組成物。然後,為除去溶劑時,藉由加熱板、在130℃下進行預烘烤2分鐘後,經由具有等間隔之線與間距的線寬1~50μm之石英製光罩,以表1中記載的曝光量(波長為405nm)進行照射。而且,曝光機係使用Suss製光罩對準曝光裝置。於照射後,藉由加熱板、在130℃下進行PEB處理3分鐘後,予以冷卻。然後,使上述塗佈基板使用2-丙醇,進行噴霧顯影處理5分鐘。其次,顯影後之膜厚及此時之解像的線寬如表1中記載。而且,各評估以下述方法為基準、實施。
為觀察樹脂組成物硬化物之剝離液耐性、特別是對大多數形成半導體元件等時使用的N-甲基-2-吡咯烷酮之剝離液耐性時,各組成物以與評估破裂耐性相同的方法,在晶圓上形成15mm×15mm之圖型。使該晶圓在NMP中、室溫下浸漬1小時後,觀察膜厚變化、外觀,且評估剝離液耐性。
為評估光硬化性樹脂組成物之絕緣破壞強度時,使表1中記載的實施例1~8及比較例1~4之組成物全部以環己酮稀釋成高分子化合物的固體成分濃度為10質量%。然後,各使用此等之稀釋溶液,使此等溶液旋轉塗佈於6吋矽晶圓上,進行為除去溶劑時之預烘烤處理。另外,在沒有經由石英製光罩下,在基板全面上照射光,進行PEB處理後,使用2-丙醇進行噴霧顯影處理2分鐘。於該操作後,再使殘留的皮膜於180℃之烤箱中加熱2分鐘,製得膜厚0.8μm之硬化皮膜。利用該硬化皮膜,藉由CV-IV測定裝置(SSM600 Solid State Measurement Inc.製),測定各光硬化性樹脂組成物之硬化皮膜的絕緣破壞強度。
為測定光硬化性樹脂組成物之硬化皮膜對基板之密接性時,使用表1記載的各實施例1~8及比較例1~4的光硬化性樹脂組成物,使此等溶液旋轉塗佈於矽晶圓基板上,且進行為除去溶劑時之預烘烤處理。然後,經由石英製光罩,在基板面上照射光,進行PEB處理後,繼續進行2-丙醇顯影處理。於該操作後,使殘留的直徑300μm、高度25μm之硬化皮膜,再於180℃之烤箱中進行加熱2小時,製得後圖型硬化皮膜。使該後圖型硬化皮膜使用黏接試驗器(Dage series 4000-PXY:Dage公司製),藉由自基板剝離圖型硬化皮膜時之阻力,評估初期之密接性。試驗條件係以試驗速度50.0μm/sec、試驗高度3.0μm進行。第1圖係表示密接性測定方法之說明圖。而且,圖中1係表示矽(Si)基板,2係表示後圖型硬化皮膜,3係表示黏接試驗器之測定工具,4係表示測定工具之移動方向。所得的數值係測定15點之平均值,數值愈高時,後圖型硬化皮膜之基板密接性愈高。另外,對焊接助劑液之藥品耐性評估,係在基板上之後圖型硬化皮膜上塗佈焊接助劑液,在220℃下加熱30秒,於冷卻後以純水洗淨,經室溫乾燥2小時之後圖型硬化皮膜,使用相同的黏接試驗器,藉由自基板剝離圖型時之阻力,測定惡化後之密接性。
藉由光硬化性樹脂組成物之硬化皮膜的溫度循環試驗觀察破裂耐性時,使用表1中記載的實施例1~8及比較例1~4之光硬化性樹脂組成物。於存在有200個直徑50μm、深度200μm之孔的矽晶圓上旋轉塗佈此等之光硬化性樹脂組成物,在孔部亦埋入光硬化性樹脂組成物,進行為除去溶劑時之預烘烤處理。然後,在基板面上全面照射光,且進行PEB處理後,繼續進行2-丙醇之顯影處理。然後,在180下進行基板之後硬化處理2小時,製得在孔部亦埋入有樹脂組成物之硬化皮膜。使該形成有硬化皮膜之基板投入1次循環為-55~150℃之溫度循環試驗機,直至循環1000次為止,觀察在孔部所埋入的硬化皮膜內是否有破裂情形產生。
上述結果如表2所示。
而且,上述表1中,各光酸產生劑如下所述。
【化26】
另外,所使用的交聯劑如下所述。
【化27】
此外,所使用的鹼性化合物如下所述。
【化28】
1...Si基板
2...直徑300μm×高度25μm之後圖型硬化皮膜
3...黏接試驗器之測定工具
4...測定工具之移動方向
[第1圖]係表示實施例之密接性測定方法的說明圖。
Claims (10)
- 一種含環氧基之高分子化合物,其特徵為具有以下述一般式(1)所示之重複單位的重量平均分子量為3,000~500,000,
- 如申請專利範圍第1項之高分子化合物,其中X為以一般式(2)所示之2價有機基,Y為以式(3)所示之2價有機基。
- 如申請專利範圍第1或2項之高分子化合物,其於上述一般式(1)中,0.05≦d/(a+b+c+d)≦0.5。
- 如申請專利範圍第1項之高分子化合物,其於上述一般式(1)中,0.05≦c/(a+b+c+d)≦0.3。
- 如申請專利範圍第1項之高分子化合物,其於上述一般式(1)中,0.05≦d/(a+b+c+d)≦0.3。
- 一種光硬化性樹脂組成物,其特徵為含有(A)申請專利範圍第1~5項中任一項之高分子化合物,(B)選自藉由甲酸水或甲醛水-醇改性的胺基縮合物、及在1分子中平均具有2個以上之羥甲基或烷氧基羥甲基之酚化合物中任何1種以上之交聯劑,(C)藉由波長190~500nm之光進行分解,產生酸之光酸產生劑,(D)溶劑。
- 如申請專利範圍第6項之光硬化性樹脂組成物,其尚含有(E)鹼性化合物。
- 一種圖型形成方法,其特徵為含有(i)使用申請專利範圍第6或7項之光硬化性樹脂組成物,在基板上形成該組成物之皮膜的步驟,(ii)經由光罩,以波長190~500nm之光進行曝光的步驟,(iii)進行曝光後之加熱處理後,以顯像液進行顯像的步驟。
- 如申請專利範圍第8項之圖型形成方法,其尚含有(iv)使藉由顯像形成圖型的皮膜在100~250℃間之溫度下進行後硬化的步驟。
- 電子零件用保護皮膜,其特徵為藉由申請專利範圍第8或9項之圖型形成方法所得的硬化皮膜所形成。
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