TWI470353B - A photosensitive resin composition and a hardening film - Google Patents
A photosensitive resin composition and a hardening film Download PDFInfo
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- TWI470353B TWI470353B TW99108503A TW99108503A TWI470353B TW I470353 B TWI470353 B TW I470353B TW 99108503 A TW99108503 A TW 99108503A TW 99108503 A TW99108503 A TW 99108503A TW I470353 B TWI470353 B TW I470353B
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- Taiwan
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- group
- formula
- resin composition
- photosensitive resin
- structural unit
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 239000002243 precursor Substances 0.000 claims description 45
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 32
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 29
- 150000004984 aromatic diamines Chemical class 0.000 claims description 27
- 229920001721 polyimide Polymers 0.000 claims description 26
- -1 aromatic tetracarboxylic acid Chemical class 0.000 claims description 25
- 239000004642 Polyimide Substances 0.000 claims description 23
- 125000004185 ester group Chemical group 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 150000001721 carbon Chemical class 0.000 claims 1
- 238000013007 heat curing Methods 0.000 claims 1
- 150000004060 quinone imines Chemical class 0.000 claims 1
- 239000010408 film Substances 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 150000004985 diamines Chemical class 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 5
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000059 patterning Methods 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CXISKMDTEFIGTG-UHFFFAOYSA-N [4-(1,3-dioxo-2-benzofuran-5-carbonyl)oxyphenyl] 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(OC=2C=CC(OC(=O)C=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)=O)=C1 CXISKMDTEFIGTG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- QGYPADVOHRLQJM-UHFFFAOYSA-N 4-(4-amino-2-ethenylphenyl)-3-ethenylaniline Chemical group C=CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C=C QGYPADVOHRLQJM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 108010039918 Polylysine Proteins 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-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
- 125000003342 alkenyl group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-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
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000006358 imidation reaction Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229920000656 polylysine Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- JZWGLBCZWLGCDT-UHFFFAOYSA-N 2,7-dichloronaphthalene-1,4,5,8-tetracarboxylic acid Chemical compound ClC1=CC(C(O)=O)=C2C(C(=O)O)=CC(Cl)=C(C(O)=O)C2=C1C(O)=O JZWGLBCZWLGCDT-UHFFFAOYSA-N 0.000 description 1
- HZMXJTJBSWOCQB-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl prop-2-enoate Chemical compound COCCOCCOC(=O)C=C HZMXJTJBSWOCQB-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- LCANECIWPMDASZ-UHFFFAOYSA-N 2-isocyanatoethanol Chemical compound OCCN=C=O LCANECIWPMDASZ-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- SMDGQEQWSSYZKX-UHFFFAOYSA-N 3-(2,3-dicarboxyphenoxy)phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O SMDGQEQWSSYZKX-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- QGRZMPCVIHBQOE-UHFFFAOYSA-N 4,8-dimethyl-1,2,3,5,6,7-hexahydronaphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)CC(C)=C2C(C(O)=O)C(C(O)=O)CC(C)=C21 QGRZMPCVIHBQOE-UHFFFAOYSA-N 0.000 description 1
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 1
- JPHCYDSESBJECU-UHFFFAOYSA-N 4-(4-amino-2-ethoxyphenyl)-3-ethoxyaniline Chemical group CCOC1=CC(N)=CC=C1C1=CC=C(N)C=C1OCC JPHCYDSESBJECU-UHFFFAOYSA-N 0.000 description 1
- GPQSJXRIHLUAKX-UHFFFAOYSA-N 4-(4-amino-2-ethylphenyl)-3-ethylaniline Chemical group CCC1=CC(N)=CC=C1C1=CC=C(N)C=C1CC GPQSJXRIHLUAKX-UHFFFAOYSA-N 0.000 description 1
- YJOAIOIVLVUPST-UHFFFAOYSA-N 4-(4-amino-2-methoxyphenyl)-3-methoxyaniline Chemical group COC1=CC(N)=CC=C1C1=CC=C(N)C=C1OC YJOAIOIVLVUPST-UHFFFAOYSA-N 0.000 description 1
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
- KEPDHDVZCBKPTD-UHFFFAOYSA-N 4-(4-amino-2-phenylphenyl)-3-phenylaniline Chemical group C=1C=CC=CC=1C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 KEPDHDVZCBKPTD-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/145—Polyamides; Polyesteramides; Polyimides
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08G73/16—Polyester-imides
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- 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
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- C09D179/085—Unsaturated polyimide precursors
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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
- G03F7/027—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
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
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Description
本發明係關於一種感光性樹脂組成物,其為可藉由光照射形成圖型,對鹼水溶液系之顯影液具優異的溶解性,且同時可提供線膨脹係數低的硬化膜。此樹脂組成物由於其耐熱性、耐藥品性,故適用於半導體元件用保護膜、覆蓋薄膜、抗焊劑等。
以往,作為感光性聚醯亞胺,可使用於聚醯亞胺之前驅體的聚醯胺酸中加成或混合具有聚合性之不飽和鍵的化合物而得的樹脂。此感光性聚醯亞胺為不飽和鍵藉由光聚合起始劑進行光交聯反應而得圖型的負型之感光性材料(專利文獻1、2)。此等係因所使用之聚醯胺酸為剛直的構造,故作為曝光後之顯影液必需為使用溶解能高的N-甲基吡咯烷酮(NMP)等的顯影液。然而,此種顯影液係環境負荷高,且顯影液之廢液處理需很大的花費。因此,期望一種感光性聚醯亞胺,為可適用環境負荷低且可低成本化的鹼系水溶液的顯影液。
感光性之聚醯亞胺之中,主鏈骨架具有剛直構造者係一般有線熱膨脹係數變小的傾向。然而,對於此等感光性聚醯亞胺,感光性基為具有多數不飽和鍵,進而側鏈之脂肪鏈變長,故具有線熱膨脹係數容易變大的缺點。此種線熱膨脹係數大的感光性聚醯亞胺,例如於半導體之晶圓上
硬化時,其硬化後因晶圓與聚醯亞胺的線熱膨脹係數之不整合,而可能有晶圓之翹曲產生。此翹曲係除了影響於覆晶封裝等的與內插板的接合信賴性之外,可能引起製程內晶圓之操作變困難等之半導體製造步驟上的不便。
此等問題之中,欲解決對顯影液之溶解之課題,提案一種正型之感光性材料,其為使用導入有酚性羥基的醯胺樹脂或/及聚苯并噁唑前驅體等的含有酚性羥基之聚醯胺樹脂與萘醌二疊氮化物(專利文獻3、4、5)。然而,此等正型光阻中,係為確保曝光前之溶解抑制、曝光後之鹼顯影性,為感光劑的萘醌二疊氮化物對樹脂而言係含有多量,故有樹脂濃度低、膜之強度等方面的問題。又。改善翹曲的手法,係提案一種含有矽氧烷之聚醯亞胺,係使由感光性樹脂組成物所形成之膜的延展性變大,而謀求減少翹曲(專利文獻6)。然而,本組成物中雖謀求延展性之改善,但未改善與矽晶圓的線熱膨脹係數之不整合,故變成樹脂內殘留歪曲的狀態。因此,在長期信賴性方面會有因此等歪曲而產生斷裂等的問題。
又,感光性聚醯胺酸樹脂組成物係一般必需於300℃以上的高溫條件下進行醯亞胺化,故於此種高溫處理困難的半導體裝置之製造製程中,係期望一種可以低溫條件進行醯亞胺化的感光性聚醯胺酸樹脂組成物。因此欲解決此種課題,係有提案一種於硬化時導入作用之觸媒(專利文獻7、8)的方法。然而,此等樹脂組成物係有受觸媒的影響而保存安定性降低或因電路等之腐蝕而信賴性降低之虞。有提案一種感光性樹脂組成物於室溫下保存安定性高、又感光性樹脂組成物之硬化時不一定需高溫處理的感光性樹脂組成物(專利文獻9)。然而,此種感光性樹脂組成物係因分子中導入有矽氧烷單位,故有硬化後所得之硬化膜中之線熱膨脹係數大、翹曲的問題。
[專利文獻1]日本特開昭54-109828號公報
[專利文獻2]日本特開2008-83468號公報
[專利文獻3]日本特開平4-31860號公報
[專利文獻4]日本特開昭56-27140號公報
[專利文獻5]日本特開2008-158263號公報
[專利文獻6]日本特開2007-132978號公報
[專利文獻7]日本特開2008-281961號公報
[專利文獻8]日本特開2007-84798號公報
[專利文獻9]WO2006/109514號公報
本發明係目的以提供可藉由光照射形成圖型,對鹼水溶液系之顯影液具優異的溶解性,且同時提供線膨脹係數低的硬化膜的感光性樹脂組成物。
本發明人等係為解決上述課題反覆專心研究的結果,發現使感光性樹脂組成物中之聚醯亞胺樹脂之構成為特定者可解決上述課題,遂完成本發明。
亦即本發明係關於一種感光性樹脂組成物,其特徵為含有具有下述式(1)、式(2)及式(3)所表示之構造單位的聚醯亞胺前驅體、及光聚合起始劑的感光性樹脂組成物,其中聚醯亞胺前驅體中之式(3)所表示之構造單位的含有比例為5~60莫耳%。
(式(1)中,X示自芳香族四羧酸去除羧基的4價芳香族基;Y示自芳香族二胺去除胺基的2價芳香族基但X及Y之任一者或二者至少含有1個酯基(-COO-)。式(2)~式(3)中,Ar示自芳香族四羧酸去除羧基的4價芳香族基;R1
~R4
係獨立地示氫原子、或碳數1~6之取代或未取代之烷基、苯基或碳數1~6之烷氧基;R5
及R6
係獨立地示具有碳數2~6之自由基聚合性之不飽和鍵的1價有機基。)
又,本發明之其它的型態係關於一種感光性樹脂組成物,其特徵為含有具有下述式(1a)、式(2a)及式(3a)所表示之構造單位的聚醯亞胺前驅體、及光聚合起始劑的感光性樹脂組成物,其中聚醯亞胺前驅體中之式(3a)所表示之構造單位的含有比例為5~60莫耳%。
(式(1a)~式(2a)中,R7
、R8
為氫或碳數1~6之烷基或烷氧基,式(1a)~式(3a)中,Ar表示4價烴基。)
因此,本發明之感光性樹脂組成物係對於聚醯亞胺前驅體100重量份,以摻合光聚合起始劑1~20重量份為佳,又可於鹼水溶液系顯影液中顯影為佳。
又,本發明係關於一種硬化膜,其特徵為使上述感光性樹脂組成物進行曝光及加熱硬化而製得,且線熱膨脹係數為40×10-6
/K以下。
[欲實施發明之形態]
以下,詳細說明本發明。
本發明之感光性樹脂組成物為含有聚醯亞胺前驅體(亦稱為聚醯胺酸)與光聚合起始劑者,可藉由光照射形成圖型。聚醯亞胺前驅體為具有上述式(1)、式(2)及式(3)所表示之構造單位。
又,聚醯亞胺前驅體亦可為具有上述式(1a)、式(2a)及式(3a)所表示之構造單位者。式(1a)、式(2a)及式(3a)中,Ar為與上述式(1)、式(2)及式(3)的Ar同意,且R7
、R8
為與R1
、R2
之說明共通。
式(1)所表示之構造單位係可使芳香族四羧酸二酐與芳香族二胺反應而得。在此,使用之芳香族四羧酸二酐及芳香族二胺係任一者或二者中含有酯基。本說明書中稱之酯基為賦予酯鍵的-COO-基。式(1)中,X示自芳香族四羧酸去除羧基的4價芳香族基;Y示自芳香族二胺去除胺基的2價芳香族基。
藉由使用由含有酯基的芳香族四羧酸二酐及含有酯基的芳香族二胺所選出之至少一者,可得式(1)所示之構造單位。由將本發明之感光性樹脂組成物經硬化而製得硬化膜中之低熱膨脹性的觀點而言,以使用不含酯基的芳香族四羧酸二酐、且使用含有酯基的芳香族二胺所製得者為佳。
作為含有酯基的芳香族四羧酸二酐,較佳可列舉下述式(4)所表示之芳香族四羧酸二酐。此等係可單獨或組合2種以上使用。
式(4)中,Z1
為由下述式所表示之芳香族基所選出之2價有機基。
作為含有酯基的芳香族二胺,較佳可列舉以NH2
-Ar-COO-Ar-NH2
、或NH2
-Ar-OCO-Ar-Q-Ar-OCO-Ar-NH2
所表示的二胺。其中,Ar為獨立地亦可具有取代基的苯環,Q為直鍵或碳數1~8之烴基。作為上述取代基係以碳數1~6之烷基或碳數1~6之烷氧基為佳。更佳為由下述式所表示之二胺所選出之芳香族二胺,此等係可單獨或組合2種以上使用。
又,此等中由使本發明之感光性樹脂組成物硬化而製得硬化膜中之低熱膨脹性之觀點而言,可列舉下述式所表示之二胺係較佳的芳香族二胺。
式中,R6
為氫原子、碳數1~6之烷基或碳數1~6之烷氧基,但以R6
為氫原子、碳數1~2之烷基或碳數1~2之烷氧基為更佳。
式(1)所示之構造單位中,特佳的構造為下述式(5)所表示之構造單位。
式(5)中表示之構造單位係可使具有4-胺基苯基-4'-胺基苯甲酸酯骨架的二胺與芳香族四羧酸二酐反應而得。式(5)中,R7
為氫原子、碳數1~6之烷基或碳數1~6之烷氧基,Ar為自芳香族四羧酸去除羧基的4價芳香族基或4價烴基。以R7
為氫原子、碳數1~2之烷基或碳數1~2之烷氧基為更佳。
為製得式(1)中所示之構造單位,可使用不含酯基的芳香族四羧酸二酐或不含酯基的芳香族二胺,對於此等芳香族四羧酸二酐或芳香族二胺將於後述。
式(2)中所示之構造單位,係可使芳香族四羧酸二酐與具有4,4'-二胺基聯苯骨架的芳香族二胺反應而製得。式(2)中,Ar示自芳香族四羧酸去除羧基的4價芳香族基,R1
~R4
係獨立地示氫原子、或碳數1~6之取代或未取代之烷基、苯基或碳數1~6之烷氧基。
具有4,4'-二胺基聯苯骨架的芳香族二胺係以下述式(6)所表示。
其中,式(6)中,R1
~R4
係獨立地示氫原子或碳數1~6之取代或未取代之烷基或者烷氧基,較佳係碳數1~6之烷基、碳數1~3之氟取代之烷基、或碳數1~3之烷氧基。
作為較佳的具有4,4'-二胺基聯苯骨架的芳香族二胺,有下述式所選出之芳香族二胺,此等係可單獨或組合2種以上使用。
式(2)中表示之構造單位中,較佳的構造為以下述式(7)所表示之構造單位。
式(7)中表示之構造單位係可使具有4,4'-二胺基聯苯骨架的二胺與芳香族四羧酸二酐反應而製得。其中,式(7)中,R8
為氫原子、碳數1~6之取代或未取代之烷基、苯基或碳數1~6之取代或未取代之烷氧基,且Ar為4價芳香族基。R8
係以碳數1~2之烷基、碳數1~2之烷氧基或碳數1~2之氟取代之烷基為較佳。
作為用以製得具有式(7)中所示之構造單位的聚醯亞胺前驅體,所使用之二胺,可列舉4,4'-二胺基-2,2'-二甲基聯苯、4,4'-二胺基-2,2'-二乙基聯苯、4,4'-二胺基-2,2'-雙(三氟甲基)聯苯、4,4'-二胺基-2,2'-二苯基聯苯、4,4'-二胺基-2,2'-二甲氧基聯苯、4,4'-二胺基-2,2'-二乙氧基聯苯等。上述二胺或四羧酸二酐係可單獨或混合2種以上使用。
式(3)中所示之構造單位係使芳香族四羧酸二酐與具有自由基聚合性之不飽和鍵的芳香族二胺反應而製得。式(3)中,Ar示自芳香族四羧酸去除羧基的4價芳香族基,R5
~及R6
係獨立地示具有碳數2~6之自由基聚合性之不飽和鍵的1價有機基。
具有自由基聚合性之不飽和鍵的芳香族二胺,係以下述一般式(8)表示。作為自由基聚合性之不飽和鍵,以乙烯性雙鍵為佳。
其中,R5
及R6
係獨立地示具有碳數2~6之自由基聚合性之不飽和鍵的1價有機基,較佳為碳數2~6之烯基或以-R10
-OOC-CR11
=CH2
(其中,R10
為直鍵或碳數1~4之2價連結基,且R11
為氫或甲基)所表示之含有(甲基)丙烯醯氧基之基。更佳為碳數2~4之烯基或(甲基)丙烯醯氧基。
又,此等之中由將本發明之感光性樹脂組成物經硬化而製得硬化膜中之低熱膨脹性的觀點而言,以下述式所表示之芳香族二胺為佳。其中,R5
及R6
係與上述相同。
式(3)中表示之構造單位之中,較佳的構造為以下述式(9)所表示之構造單位。
式(9)中表示之構造單位,係可使4,4'-二胺基-2,2'-二乙烯基聯苯與芳香族四羧酸二酐反應而製得。式(9)中,Ar為4價芳香族基或烴基。
如上述說明,以式(1)~式(3)所表示之構造單位或具有此等構造單位的聚醯亞胺前驅體,係使芳香族四羧酸二酐與芳香族二胺反應而製得。式(1)~式(3)中,X及Ar為自芳香族四羧酸或其之酸酐去除羧基或酸酐的4價芳香族基(芳香族四羧酸殘基),故由使用之芳香族四羧酸二酐的說明可理解X及Ar。
以下,對芳香族四羧酸二酐進行說明。製得式(1)所表示之構造單位之際,使用含有酯基的芳香族四羧酸二酐的情形,係如上述較佳使用式(4)所表示之芳香族四羧酸二酐。欲製得其它式(1)~式(3)所表示之構造單位或具有此等構造單位的聚醯亞胺前驅體,所使用之芳香族四羧酸二酐係可列舉如下之芳香族四羧酸二酐。使用含有酯基之芳香族四羧酸二酐的情形,賦予式(2)所表示之構造單位時,係作為式(2)所表示之構造單位計算,其它係作為式(1)所表示之構造單位計算。
作為芳香族四羧酸二酐,無特別限制地可使用之列舉其具體例為均苯四甲酸二酐、2,2',3,3'-、2,3,3',4'-或3,3',4,4'-二苯基酮四羧酸二酐、2,3,6,7-、1,2,4,5-、1,4,5,8-、1,2,6,7-或1,2,5,6-萘-四羧酸二酐、4,8-二甲基-1,2,3,5,6,7-六氫萘-1,2,5,6-四羧酸二酐、2,6-或2,7-二氯萘-1,4,5,8-四羧酸二酐、2,3,6,7-(或1,4,5,8-)四氯萘-1,4,5,8-(或2,3,6,7-)四羧酸二酐、3,3',4,4'-、2,2',3,3'-或2,3,3',4'-聯苯四羧酸二酐、3,3",4,4"-、2,3,3",4"-或2,2",3,3"-p-聯三苯四羧酸二酐、2,2-雙(2,3-或3,4-二羧基苯基)-丙烷二酐、雙(2,3-二羧基苯基)醚二酐、雙(2,3-或3,4-二羧基苯基)甲烷二酐、雙(2,3-或3,4-二羧基苯基)碸二酐、1,1-雙(2,3-或3,4-二羧基苯基)乙烷二酐、2,3,8,9-、3,4,9,10-、4,5,10,11-或5,6,11,12-苝-四羧酸二酐、1,2,7,8-、1,2,6,7-或1,2,9,10-菲-四羧酸二酐、吡-2,3,5,6-四羧酸二酐、吡咯啶-2,3,4,5-四羧酸二酐、噻吩-2,3,4,5-四羧酸二酐、4,4'-氧基二苯二甲酸二酐等。此等芳香族四羧酸二酐係可單獨或組合2種以上使用。上述芳香族四羧酸二酐之中,亦尤其以均苯四甲酸二酐為可確保線熱膨脹係數與良好的鹼顯影性,故較佳。
上述式(1)~式(3)所表示之構造單位,係芳香族二胺與芳香族四羧酸之反應所製得之成為醯胺酸構造,但感光性樹脂組成物中之聚醯亞胺前驅體係其一部份亦可醯亞胺化。但為確保良好的鹼顯影性,其醯亞胺化率以低於10%為理想,醯亞胺化率為5%以下較佳、更佳為低於1%。前驅體之醯亞胺化率係使用傅立葉變換紅外分光光度計(市售品:日本分光製FT/IR620),以1次反射ATR法藉由測定聚醯亞胺薄膜之紅外線吸收光譜,以1015cm-1
附近之苯環吸收體作為基準,由1780cm-1
之來自醯亞胺基之C=O伸縮的吸光度算出。又,此醯胺酸構造係於感光性樹脂組成物之硬化反應時藉由其羧酸之質子成為酸觸媒而作用,成為可於低溫度下進行醯亞胺化反應(硬化反應)。由如此觀點而言,其醯亞胺化率係以低於10%為理想。
聚醯亞胺前驅體中之式(1)、(2)及(3)的構造單位之比例,係必需使式(3)之構造單位為5~60莫耳%之範圍。較佳為15~50莫耳%的範圍。式(3)之含有比例不滿5莫耳%時,無法經由交聯形成充分的圖型,而超過60莫耳%則交聯密度變高、薄膜會變脆。式(1)及式(2)之構造單位之比例係以合計含有40~95莫耳%、較佳為50~85莫耳%之比例。其合計比例不滿40莫耳%時,不易發現由此等構成所顯現之對鹼水溶液系之顯影液的顯影性、或低線膨脹係數等其它所定的機能,而超過95莫耳%則不能充分形成圖型。
聚醯亞胺前驅體中,式(1)之構造單位的含有比例係以10~80莫耳%之範圍、更佳以25~70莫耳%為佳。此比例未滿10莫耳%則有藉由鹼顯影液之顯影性降低的傾向,又超過80莫耳%,則有形成薄膜或膜時變脆的傾向。又,式(2)之構造單位的含有比例係以5~85莫耳%之範圍、更佳以10~60莫耳%為佳。此比例未滿5莫耳%則有線膨脹係數變大的傾向,且因與同時所使用之金屬材料等之低熱膨
脹性材料有線膨脹係數的差異,而容易產生翹曲。又,超過85莫耳%則有對鹼顯影液之顯影性降低的傾向。
本發明中所使用之聚醯亞胺前驅體係以含有式(1)、(2)及(3)之構造單位作為必須的構造單位,亦可具有少量之由其它的二胺所產生之構造單位。作為所述之構造單位,以式(11)表示之構造單位為較佳者。
式(11)中,R9
為2價烴基,來自二胺的主骨架。作為此二胺,具體地可列舉4,4'-二胺基二苯基醚、3,4'-二胺基二苯基醚、4,4'-二胺基-2'-甲氧基苯甲醯胺苯、4,4'-二胺基苯甲醯胺苯、3,4'-二胺基苯甲醯胺苯、1,4-雙(4-胺基苯氧基)苯、1,3-雙(4-胺基苯氧基)苯、1,3-雙(3-胺基苯氧基)苯、1,4-二胺基苯、1,3-二胺基苯、2,4-二胺基甲苯、4,4'-二胺基二苯基甲烷、4,4'-二胺基二苯基碸、3,3'-二胺基二苯基碸、4,4'-二胺基聯苯、4,4-二胺基二苯基酮、4,4-二胺基二苯基硫醚、2,2-雙[4-(4-胺基苯氧基)苯基]丙烷等。此等係可單獨或組合2種以上使用。此等二胺係亦有式(1)中之Y不具有酯基的2價芳香族基時,所使用之二胺的較佳之例。又,Ar為不具有酯基的4價芳香族基。
聚醯亞胺前驅體中之式(11)所表示之構造單位,以不超過50莫耳%的比例為理想。其比例超過50莫耳%時,線熱膨脹係數、鹼顯影性、圖型性能之任一者或全部,有無法發揮所定的機能之可能、更佳係以不超過20莫耳%的範圍為佳。
上述聚醯亞胺前驅體為使賦予上述構造單位之至少3種的芳香族二胺與至少1種的芳香族四羧酸二酐以幾乎相當的莫耳,進行反應而合成之。反應係於有機溶劑中以0~60℃之溫度範圍進行為理想。反應溫度過低時,反應無法充分進行,有無法獲得必需的分子量的聚醯亞胺之虞。又,反應溫度過高時,有與聚合反應同時地進行醯亞胺化的情形,不只對鹼水溶液系之顯影液的溶解性降低,還有反應溶液成膠化的情形。
此時使用之有機溶劑,係具體地可單獨或混合使用二甲基亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺基、N-甲基-2-吡咯烷酮、六甲基磷酸三醯胺、苯酚、甲酚、γ-丁內酯等。此等有機溶劑之使用量係無特別規定,但以經由聚合反應所製得之聚醯胺酸溶液的濃度成為5~40重量%左右為佳。
本發明之感光性樹脂組成物係含有如此進行所得之聚醯亞胺前驅體與光聚合起始劑作為必須成分,但亦可視需要而加入其它樹脂或丙烯酸酯等之單體、增感劑、溶劑等。藉作作成此種感光性樹脂組成物,可成為具有實用性更優異的特性。
感光性樹脂組成物中摻合丙烯酸酯時,作為可使用之丙烯酸酯,可使用例如2-乙基己基丙烯酸酯、2-羥基乙基丙烯酸酯、2-羥基丙基丙烯酸酯、2-羥基乙基丙烯醯基磷酸酯、2-甲氧基乙氧基乙基丙烯酸酯、2-乙氧基乙氧基乙基丙烯酸酯、四氫糠基丙烯酸酯、苯氧基乙基丙烯酸酯、異癸基丙烯酸酯、十八基丙烯酸酯、月桂基丙烯酸酯、縮水甘油丙烯酸酯、烯丙基丙烯酸酯、乙氧基丙烯酸酯、甲氧基丙烯酸酯、N,N'-二甲基胺基乙基丙烯酸酯、苄基丙烯酸酯、2-羥基乙基丙烯醯基磷酸酯、二環戊二烯基丙烯酸酯、二環戊二烯乙氧基丙烯酸酯等單丙烯酸酯、或二環戊烯基丙烯酸酯、二環戊烯基氧基乙基丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,6-丁二醇二丙烯酸酯、二乙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、聚乙二醇200二丙烯酸酯、聚乙二醇400二丙烯酸酯、聚乙二醇600二丙烯酸酯、二乙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、羥基三甲基乙酸酯新戊二醇二丙烯酸酯、三乙二醇二丙烯酸酯、雙(丙烯醯氧基乙氧基)雙酚A、雙(丙烯醯氧基乙氧基)四溴雙酚A、三丙二醇二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、新戊四醇三丙烯酸酯、參(2-羥基乙基)異氰酸酯、新戊四醇四丙烯酸酯、二新戊四醇六丙烯酸酯、二新戊四醇單羥基五丙烯酸酯等的多官能丙烯酸酯。丙烯酸酯較佳係使用多官能的情形,相對於聚醯亞胺前驅體100重量份以摻合5~60重量份、較佳為10~40重量份、更佳為10~30重量份。
作為感光性樹脂組成物中所摻合之光聚合起始劑,可使用光自由基聚合起始劑。此光自由基聚合起始劑係藉由光照射產生聚合性的自由基,此自由基與感光性樹脂組成物內的不飽和鍵反應而形成交聯構造,於顯影液中不溶化。於此,所使用之光自由基聚合起始劑,例如,可使用苯乙酮、2,2-二甲氧基苯乙酮、p-二甲基胺基苯乙酮、米其勒酮、苄酯、苯偶因、苯偶因甲基醚、苯偶因乙基醚、苯偶因異丙基醚、苯偶因n-丙基醚、苯偶因異丙基醚、苯偶因n-丁基醚、苄基二甲基縮酮、噻噸酮、2-氯噻噸酮、2-甲基噻噸酮、2-羥基-2-甲基-1-苯基-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、甲基苯甲醯基甲酸酯、1-羥基環己基苯基酮等之種種的光聚合起始劑。光聚合起始劑的使用量,係對於聚醯亞胺前驅體100重量份以1~20重量份、較佳1~10重量份的範圍。
又,摻合增感劑也是有利的,此時,作為增感劑可使用4,4'-雙(二乙基胺基)二苯基酮等。增感劑係對於聚醯亞胺前驅體100重量份,可添加0.01~2重量份、較佳0.05~0.5重量份。
本發明之感光性樹脂組成物,可藉由各種有機溶劑等調整黏度。例示較佳的有機溶劑,可列舉三乙二醇二甲基醚、二乙二醇二甲基醚、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、丙二醇單甲基醚乙酸酯、乳酸乙酯、二甲基亞碸、N,N-二甲基甲醯胺、γ-丁內酯或此等的混合溶劑。溶劑之使用量係對於感光性樹脂組成物之固形分100重量份,以10~100重量份之範圍為佳。聚醯亞胺前驅體製造之際,
作為反應溶劑所使用之有機溶劑有殘留時,作為此溶劑計算。
本發明之感光性樹脂組成物係可藉由一般所知的使用方法使用。例如,將調製好的感光性樹脂組成物塗佈於支持體(例如,矽晶圓、陶瓷基板、剛性基板、撓性基板等)。塗佈方法係無特別限定,可列舉旋轉塗佈器、狹縫塗佈器、輥塗佈器、印刷等。藉由此等方法塗佈後,以50~180℃、較佳80~140℃進行乾燥,可成薄膜狀感光性樹脂組成物。此乾燥後的塗膜係可經由任意地調整感光性樹脂組成物的濃度、或塗佈厚度,使成為所欲的厚度。作為半導體元件用保護膜或覆蓋薄膜時,通常塗佈使成為5~100μm之厚度。此塗膜薄時,不能充分保護塗膜下的元件或電路,又過厚則難製得精度良好的加工圖型。
接著,使用所欲之圖型的光罩進行曝光。曝光光源係適合地可使用200~500nm的紫外線~可見光。
其次,藉由於顯影液中溶解除去未曝光部,可得所欲之圖型。使用本發明之感光性樹脂組成物時,於曝光部藉由光照射光聚合起始劑產生自由基,因與不飽和鍵連鎖地反應進行交聯,故對顯影液為不溶化。由於未曝光部溶解於鹼顯影液,故利用曝光部與未曝光部之溶解度差別而形成圖型。
此顯影步驟中所使用之鹼水溶液系之顯影液,可使用例如氫氧化鈉、氫氧化鉀、碳酸鈉等的無機鹼類、乙基胺、n-丙基胺等的1級胺、二乙基胺、二-n-丙基胺等的2級
胺、三乙基胺、甲基二乙基胺等的3級胺、二甲基乙醇胺、三乙醇胺等的醇胺類、四甲基氫氧化銨(TMAH)、四乙基氫氧化銨等的4級銨鹽等的有機鹼類的水溶液。又,可適宜地使用於此等中適量添加有甲醇、乙醇、1-丙醇、2-丙醇等的水溶性醇或界面活性劑的顯影液。作為可比較容易溶解聚合物的有機溶劑,一般所使用之非質子性極性溶劑,例如加入NMP、N,N-二甲基甲醯胺(DMF)、N,N-二甲基乙醯胺(DMAc)、二甲亞碸(DMSO)亦可提高顯影性,但在本發明係不特別需要,以不使用此等為理想。顯影方法可使用噴霧、攪煉、浸漬等的方法。
如此方式所得之圖型係於蒸餾水等中洗淨後,進行加熱處理(後硬化(postcure))。以此後硬化步驟,自聚醯亞胺的前驅體構造藉由脫水閉環使形成醯亞胺環,故可得耐熱性優異的圖型。此加熱處理係可以180~400℃進行10~120分鐘、更佳為以180℃~300℃進行。又,加熱步驟係可以多階段進行升溫。
本發明之感光性樹脂組成物的被膜於曝光處理後、或曝光、顯影、洗淨處理後,藉由進行上述後硬化作為欲醯亞胺化的加熱處理而製得硬化膜。可使此硬化膜的線熱膨脹係數為40×10-6
/K以下、較佳為20×10-6
/K以下。
以下,對本發明之實施例具體地說明。圖型化性能評
估、線熱膨脹係數之測定係如以下方式進行。
於貼銅層合板(新日鐵化學股份有限公司製ESPANEX:MC12-25-00CEM)之銅箔面上以旋轉塗佈方式塗佈感光性樹脂組成物後,於110℃乾燥3分鐘。曝光係使用高壓水銀燈以總曝光量為1000mJ進行曝光。顯影係使用2.38wt%TMAH水溶液作為顯影液,於30℃進行2分45秒。所得之圖型係於水洗後,於220℃進行30分鐘後硬化。後硬化後的膜厚約為10μm。圖型化性能係以可解析之最小的孔洞(Via)徑進行評估。
線熱膨脹係數之測定,係使用以銅箔為基材,且於其上塗佈感光性樹脂組成物,在顯影、後硬化後形成的圖型由除去基材而得的薄膜狀樣本,且使用Seiko Instruments股份有限公司製TMA100來進行測定。測定係將前述薄膜狀樣本冷卻至-20℃後,以10℃/分鐘的速度升溫至250℃為止,由100℃~200℃為止的平均值求出線熱膨脹係數。
本實施例中使用之縮寫符號係表示以下之化合物。
APAB:4-胺基苯基-4'-胺基苯甲酸酯
BAPT:雙(4-胺基苯基)對苯二甲酸酯
mTB:4,4'-二胺基-2,2'-二甲基聯苯
VAB:4,4'-二胺基-2,2'-二乙烯基聯苯
MAB:4,4'-二胺基-2,2'-二甲基丙烯醯氧基聯苯
TFMB:4,4'-二胺基-2,2'-雙(三氟甲基)聯苯
PMDA:均苯四甲酸酐
TAHQ:p-伸苯基雙(偏苯三甲酸單酯酸酐)
於氮流通過的300ml三口燒瓶中,使6.2g的APAB(0.027莫耳)、9.6g的mTB(0.045莫耳)及4.3g的VAB(0.018莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入19.2g的PMDA(0.088莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體1。
對於如此方式所製得之聚醯亞胺前驅體(固形分)100重量份,摻合5重量份之作為自由基聚合起始劑的Ciba Japan製IRGACURE OXE-02、30重量份之作為多官能丙烯酸酯的日本化藥製PET-30。摻合後,使用攪拌機充分攪拌後,以真空脫泡除去樹脂內的空氣,而製得感光性樹脂組成物。
對所製得之感光性樹脂組成物,進行圖型化性能評估與線膨脹係數之測定。將實施例之聚醯亞胺前驅體的原料組成與評估結果示於表1。
於氮流通過的300ml三口燒瓶中,使14.3g的APAB(0.063
莫耳)、1.9g的mTB(0.009莫耳)及4.2g的VAB(0.018莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入19.0g的PMDA(0.087莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體2。
於氮流通過的300ml三口燒瓶中,使10.3g的APAB(0.045莫耳)、5.7g的mTB(0.027莫耳)及4.3g的VAB(0.018莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入19.1g的PMDA(0.088莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體3。
於氮流通過的300ml三口燒瓶中,使6.1g的APAB(0.027莫耳)、3.8g的mTB(0.018莫耳)及10.6g的VAB(0.045莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入18.9g的PMDA(0.087莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體4。
於氮流通過的300ml三口燒瓶中,使9.3g的APAB(0.041莫耳)、5.2g的mTB(0.024莫耳)及3.9g的VAB(
0.017莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入14.1g的PMDA(0.065莫耳)及7.4g的TAHQ(0.016莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體5。
於氮流通過的300ml三口燒瓶中,使12.3g的mTB(0.058莫耳)及3.4g的VAB(0.014莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入7.6g的PMDA(0.036莫耳)及16.4g的TAHQ(0.036莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體6。
於氮流通過的300ml三口燒瓶中,使18.5g的BAPT(0.053莫耳)、1.6g的mTB(0.008莫耳)及3.6g的VAB(0.015莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入16.3g的PMDA(0.075莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體7。
於氮流通過的300ml三口燒瓶中,使9.9g的APAB(0.043莫耳)、5.5g的mTB(0.026莫耳)及6.1g的MAB(0.017
莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入18.5g的PMDA(0.085莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體1。
於氮流通過的300ml三口燒瓶中,使9.6g的APAB(0.042莫耳)、8.1g的TFMB(0.025莫耳)及4.0g的VAB(0.017莫耳)溶解於160g的N,N'-二甲基乙醯胺中。接著,於室溫下對此溶液一邊攪拌一邊加入18.2g的PMDA(0.084莫耳)後,進而攪拌3小時,而製得聚醯亞胺前驅體9。
對於實施例2~9中所製得的聚醯亞胺前驅體,以與實施例1同樣的方式,摻合自由基聚合起始劑及多官能丙烯酸酯後,使用攪拌機充分攪拌後以真空脫泡除去樹脂內的空氣,而製得實施例2~9的感光性樹脂組成物。
對於所製得之實施例2~9的感光性樹脂組成物,進行圖型化性能評估與線膨脹係數之測定。將實施例之聚醯亞胺前驅體的原料組成與評估結果示於表1。
除了不使用VAB,且使其它的使用量為表1所示的量之外,與實施例1同樣的方式合成聚醯亞胺前驅體溶液,接著與實施例1同樣地方式以製得感光性樹脂組成物。所製得之感光性樹脂組成物,係曝光後無法確認圖型且顯影時溶解於所有的顯影液,故無法製得用以評估線熱膨脹係數的薄膜。
比較例2
除了不使用APAB,且使其它的使用量為表2所示的量之外,與實施例1同樣的方式合成聚醯亞胺前驅體溶液,接著與實施例1同樣地方式以製得感光性樹脂組成物。所製得之感光性樹脂組成物,係曝光後無法確認圖型且顯影時無曝光部、未曝光部之溶解度差別,有膜膨潤‧剝離情形,故無法製得圖型。因此,無法製得用以評估線熱膨脹係數的薄膜。
比較例3
除了不使用mTB,且使其它的使用量為表2所示的量之外,與實施例1同樣的方式合成聚醯亞胺前驅體溶液,接著與實施例1同樣地方式以製得感光性樹脂組成物。所製得之感光性樹脂組成物,係不但曝光後無法確認圖型且顯影時全部流掉,故無法製得圖型。因此,無法製得用以評估線熱膨脹係數的薄膜。
由表1所示之結果可清楚地確認由各實施例所製得的感光性樹脂組成物係對鹼顯影液具有充分的圖型化性能。又,可確認線熱膨脹係數亦相當的低,故有效減低翹曲。對此,由比較例係無法圖型化且無法製得薄膜來看,可確認為不能使用作為感光性樹脂組成物者。
本發明之感光性樹脂組成物係對鹼顯影液具有充分的圖型化性能,且因線熱膨脹係數亦相當低,故有效減低翹曲。進而,本發明之感光性樹脂組成物係亦可於250℃以下之加熱硬化,故可應用於高溫處理困難的半導體裝置之製造製程,為其工業價值高者。
Claims (11)
- 一種感光性樹脂組成物,其特徵為含有具有下述式(1)、式(2)及式(3)所表示之構造單位的聚醯亞胺前驅體、及光聚合起始劑,其中聚醯亞胺前驅體中之式(3)所表示之構造單位的含有比例為5~60莫耳%,
- 如申請專利範圍第1項之感光性樹脂組成物,其中 對於聚醯亞胺前驅體100重量份,摻合光聚合起始劑1~20重量份。
- 如申請專利範圍第1項之感光性樹脂組成物,其中感光性樹脂組成物為可於鹼水溶液系顯影液中顯影。
- 一種硬化膜,其特徵為使申請專利範圍第1~3項中任一項之感光性樹脂組成物進行曝光及加熱硬化而製得,且線熱膨脹係數為40×10-6 /K以下。
- 如申請專利範圍第1項之感光性樹脂組成物,其中,式(1)所示之構造單位係含有酯基的芳香族四羧酸二酐與芳香族二胺進行反應而得者,且含有酯基的芳香族四羧酸二酐為下述式(4)所表示之芳香族四羧酸二酐,
- 如申請專利範圍第1項之感光性樹脂組成物,其中,式(1)所示之構造單位係芳香族四羧酸二酐與含有酯基的芳香族二胺進行反應而得者,且含有酯基的芳香族二胺,為以NH2 -Ar-COO-Ar-NH2 、或NH2 -Ar-OCO-Ar-Q-Ar-OCO-Ar-NH2 所表示的芳香族二胺(其中,Ar為獨立地亦可具有取代基的苯環,Q為直鍵或碳數1~8之烴基,且上述取代基係碳數1~6之烷基或碳數1~6之烷氧基)。
- 如申請專利範圍第5項之感光性樹脂組成物,其中,芳香族二胺為以下述式所表示之芳香族二胺,
- 如申請專利範圍第1項之感光性樹脂組成物,其中,式(1)所示之構造單位為下述式(5)所表示之構造單位,
- 如申請專利範圍第1項之感光性樹脂組成物,其中,聚醯亞胺前驅體中,式(1)之構造單位的含有比例係10~80莫耳%,式(2)之構造單位的含有比例係5~85莫耳%。
- 如申請專利範圍第1項之感光性樹脂組成物,其中,聚醯亞胺前驅體中,式(1)之構造單位的含有比例係25~70莫耳%,式(2)之構造單位的含有比例係10~60莫耳%。
- 一種感光性樹脂組成物,其特徵為含有具有下述式(1a)、式(2a)及式(3a)所表示之構造單位的聚醯亞胺前驅體、及光聚合起始劑的感光性樹脂組成物,其中聚醯亞胺前驅體中之式(3a)所表示之構造單位的含有比例為5~60莫耳%,
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