JPWO2011049011A1 - 感光性接着剤組成物、感光性接着剤シートおよびこれらを用いた半導体装置 - Google Patents
感光性接着剤組成物、感光性接着剤シートおよびこれらを用いた半導体装置 Download PDFInfo
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- JPWO2011049011A1 JPWO2011049011A1 JP2010544914A JP2010544914A JPWO2011049011A1 JP WO2011049011 A1 JPWO2011049011 A1 JP WO2011049011A1 JP 2010544914 A JP2010544914 A JP 2010544914A JP 2010544914 A JP2010544914 A JP 2010544914A JP WO2011049011 A1 JPWO2011049011 A1 JP WO2011049011A1
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- Prior art keywords
- photosensitive adhesive
- adhesive composition
- general formula
- soluble polyimide
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000853 adhesive Substances 0.000 title claims abstract description 182
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 182
- 239000000203 mixture Substances 0.000 title claims abstract description 131
- 239000004065 semiconductor Substances 0.000 title claims description 23
- 229920001721 polyimide Polymers 0.000 claims abstract description 86
- 239000004642 Polyimide Substances 0.000 claims abstract description 84
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 239000000758 substrate Substances 0.000 claims abstract description 57
- 239000004593 Epoxy Substances 0.000 claims abstract description 46
- 150000004985 diamines Chemical class 0.000 claims abstract description 20
- 125000004427 diamine group Chemical group 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000001174 sulfone group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 150000008065 acid anhydrides Chemical group 0.000 claims description 4
- 238000009413 insulation Methods 0.000 abstract description 25
- 238000000034 method Methods 0.000 description 45
- 235000012431 wafers Nutrition 0.000 description 43
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 41
- 239000010703 silicon Substances 0.000 description 41
- 229910052710 silicon Inorganic materials 0.000 description 41
- -1 aliphatic ether diamine Chemical class 0.000 description 40
- 238000000576 coating method Methods 0.000 description 28
- 239000002966 varnish Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- 239000011248 coating agent Substances 0.000 description 24
- 238000011161 development Methods 0.000 description 19
- 230000018109 developmental process Effects 0.000 description 19
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 239000011521 glass Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 239000011342 resin composition Substances 0.000 description 9
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 8
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
- 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 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000006358 imidation reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000010030 laminating Methods 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 150000002923 oximes Chemical class 0.000 description 6
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 239000009261 D 400 Substances 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 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 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- AJOJTMNIQSTBAP-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-3-yl) prop-2-enoate Chemical compound CN1C(C)(C)CCC(OC(=O)C=C)C1(C)C AJOJTMNIQSTBAP-UHFFFAOYSA-N 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-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
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- LRZPQLZONWIQOJ-UHFFFAOYSA-N 10-(2-methylprop-2-enoyloxy)decyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOC(=O)C(C)=C LRZPQLZONWIQOJ-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 2
- YJVIKVWFGPLAFS-UHFFFAOYSA-N 9-(2-methylprop-2-enoyloxy)nonyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCOC(=O)C(C)=C YJVIKVWFGPLAFS-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
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- 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
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
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- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
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Abstract
Description
ODPA:4,4’−オキシジフタル酸二無水物(マナック(株)製)
6FDA:4,4’−(ヘキサフロロイソプロピリデン)ジフタル酸二無水物(ダイキン工業(株)製)
BAHF:2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(AZエレクトロニックマテリアルズ(株)製)
MBAA:[ビス(4−アミノ−3−カルボキシ)フェニル]メタン(和歌山精化工業(株)製)
SiDA:ビス(3−アミノプロピル)テトラメチルジシロキサン(信越化学(株)製)
MAP:3−アミノフェノール(東京化成(株)製)
D−230:ポリオキシプロピレンジアミン(三井化学ファイン(株)製、商品名“ジェファーミン”D−230 一般式(4)のa=2〜3)
D−400:ポリオキシプロピレンジアミン(三井化学ファイン(株)製、商品名“ジェファーミン”D−400 一般式(4)のa=5〜7)。
<光重合性化合物>
BP−6EM:エチレンオキサイド変性ビスフェノールAジメタクリレート(共栄社化学(株)製、商品名“BP−6EM”)
DCP−A:トリシクロデカンジメタノールジアクリレート(共栄社化学(株)製、商品名“DCP−A”)
MOI−BP:2−イソシアナートエチルメタクリレートブロック体(昭和電工(株)製“カレンズ(登録商標)”MOI−BP)
DPE−6A:ジペンタエリストールヘキサアクリレート(共栄社化学(株)製、商品名“DPE−6A”)
<エポキシ化合物>
EP4003S:プロピレンオキサイド変性BisA型エポキシ樹脂((株)アデカ製、商品名“アデカレジン(登録商標)”EP−4003S、一般式(1)におけるm+n=5〜6
EP4000S:プロピレンオキサイド変性BisA型エポキシ樹脂((株)アデカ製、商品名“アデカレジン(登録商標)”EP−4000S、一般式(1)におけるm+n=1〜2
EP4010S:プロピレンオキサイド変性BisA型エポキシ樹脂((株)アデカ製、商品名“アデカレジン(登録商標)”EP−4010S、一般式(1)におけるm+n=1〜2のものの2量体(すなわち、下記式(6)で表される化合物)
<光重合開始剤>
NCI831:光ラジカル重合開始剤(アデカ(株)製、商品名“NCI−831”)
<界面活性剤>
L1980:“ディスパロン(登録商標)”L1980(楠本化成(株)製)
<溶媒>
γBL:γブチロラクトン。
<ポリイミドの分子量>
ポリイミドをNMP(N−メチルピロリドン)に溶解した固形分濃度0.1重量%の溶液を用い、下に示す構成のGPC装置Waters2690(Waters(株)製)により測定し、ポリスチレン換算の重量平均分子量を算出した。GPC測定条件は、移動相をLiClとリン酸をそれぞれ濃度0.05mol/Lで溶解したNMP溶液とし、展開速度を0.4ml/分とした。
検出器:Waters996
システムコントローラー:Waters2690
カラムオーブン:Waters HTR−B
サーモコントローラー:Waters TCM
カラム:TOSOH grard comn
カラム:TOSOH TSK−GEL α−4000
カラム:TOSOH TSK−GEL α−2500 。
まず、ポリマーの赤外吸収スペクトルを測定し、ポリイミドに起因するイミド構造の吸収ピーク(1780cm−1付近、1377cm−1付近)の存在を確認した。次に、そのポリマーについて、350℃で1時間熱処理した後、再度、赤外吸収スペクトルを測定し、熱処理前と熱処理後の1377cm−1付近のピーク強度を比較した。熱処理後のポリマーのイミド化率を100%として、ピーク強度比から、熱処理前のポリマーのイミド化率を求めた。
各実施例および比較例で作製した感光性接着剤組成物ワニスをコンマロールコーターを用いて、厚さ38μmのPETフィルム上に塗布し、100℃で15分間乾燥を行った後、保護フィルムとして、厚さ10μmのPPフィルムをラミネートし、感光性接着剤シートを得た。感光性接着剤組成物被膜の膜厚は25μmとなるように塗工を行った。その後保護フィルムを剥離し、該剥離面を、シリコンウェハ上に、ラミネート装置((株)タカトリ製、VTM−200M)を用いて、ステージ温度80℃、ロール温度80℃、圧力150Pa、貼付速度5mm/秒、貼付圧力0.2MPaの条件でラミネートした。そして、支持体フィルムを剥がした時、感光性接着剤組成物被膜が支持体フィルムに残らず、シリコンウェハに貼り付けされたものをA、一部貼り付けされたものをB、貼り付けできず支持体フィルムに残っているものをCとした。
上記と同様の方法で得られた感光性接着剤シートの保護フィルムを剥離し、該剥離面を、シリコンウェハ上に、ラミネート装置((株)タカトリ製、VTM−200M)を用いて、ステージ温度80℃、ロール温度80℃、圧力150Pa、貼付速度5mm/秒、貼付圧力0.2MPaの条件でラミネートした。そして、支持体フィルムを剥した後、超高圧水銀灯を光源とする露光装置にL/S(ライン・アンド・スペース)=75/75、50/50、40/40、30/30、25/25μmのパターンを有するマスクをセットし、露光量400mJ/cm2(h線換算)で露光を行った。露光後、ディップ現像にて、水酸化テトラメチルアンモニウムの2.38%水溶液を用いて未露光部を除去し、水にてリンス処理をした。現像時間は、未露光部が完全に溶解した時間の2倍の時間とした。この様にして得られたパターンを、光学顕微鏡で観察し、パターンのラインに詰まり等の異常のない最小のパターンのサイズを解像度の評価とした。
<感光性接着剤シートの熱圧着性の評価>
上記と同様の方法で得られた感光性接着剤シートの保護フィルムを剥離し、該剥離面を、シリコンウェハ上に、ラミネート装置((株)タカトリ製、VTM−200M)を用いて、ステージ温度80℃、ロール温度80℃、圧力150Pa、貼付速度5mm/秒、貼付圧力0.2MPaの条件でラミネートした。そして、支持体フィルムを剥した後、超高圧水銀灯を光源とする露光装置を用いて露光量400mJ/cm2(h線換算)で露光を行った。上記で得られた露光後の感光性接着剤組成物被膜付きシリコンウェハを50×50mmに切断して、感光性接着剤組成物被膜を上にしてホットプレート上に載せ1分間保持した。1分後、2×2mmのシリコンウェハをその上に乗せて、100℃から10℃ずつ温度を上げて試験をおこなった。感光性接着剤組成物被膜にタック性が生じ、シリコンウェハと接着した最低の温度を熱圧着温度とした。より低温でタック性が生じるものが優れている。
上記と同様の方法で得られた感光性接着剤シートの保護フィルムを剥離し、超高圧水銀灯を光源とする露光装置を用いて露光量400mJ/cm2(h線換算)で露光を行った。露光後の感光性接着剤シートを5×5mmにカットした。カットしたサンプルを150℃のホットプレート上で加熱されたガラス板の上に、ガラス板と感光性接着剤組成物被膜とが接するように貼り合わせて、支持体フィルムの上から30秒間、500g分銅をのせて加圧した。30秒後、ガラス板に接着された感光性接着剤シートを光学顕微鏡で観察して、支持体フィルムからはみ出した感光性接着剤組成物の一番長い部分の長さを計測した。(支持体フィルムからはみ出した長さ)/(圧着前の長さ(5mm))を熱フロー量として算出した。
上記と同様の方法で得られた感光性接着剤シートの保護フィルムを剥離し、該剥離面を、シリコンウェハ上に、ラミネート装置((株)タカトリ製、VTM−200M)を用いて、ステージ温度80℃、ロール温度80℃、圧力150Pa、貼付速度5mm/秒、貼付圧力0.2MPaの条件でラミネートした。そして、支持体フィルムを剥した後、超高圧水銀灯を光源とする露光装置を用いて露光量400mJ/cm2(h線換算)で露光を行った。露光後の感光性接着剤組成物被膜付きシリコンウェハを50×50mmに切断して、感光性接着剤組成物被膜を上にして150℃のホットプレート上に載せ1分間保持した。1分後、2×2mmのシリコンウェハをその上に乗せて、圧力0.2MPa、時間30秒で熱圧着した。その後、250℃のイナートオーブン窒素雰囲気下で60分加熱して硬化させ、シリコンウェハ同士を接着したサンプルを得た。その後、ダイシェアテスタ(Dageシリーズ4000)を用いて、温度30℃で接着力を評価した。
サンプルサイズ 2mm×2mm
テストスピード 200μm/s
テスト高さ 300μm
<絶縁信頼性試験>
L/S=10μm/10μmの銅櫛歯電極上に、各実施例および比較例で作製した感光性樹脂組成物をピンセットの先端部を用いて塗布し、大気中100℃で15分乾燥させた。次いで、超高圧水銀灯を用いて、露光量400mJ/cm2(h線換算)で露光処理を行った後、イナートオーブンを用いて、N2雰囲気下、200℃で60分間熱処理し、評価用サンプルを作製した。得られた評価用サンプルの電極間に、温度85℃、相対湿度85%の雰囲気下で、電圧20Vを印加し続け1000時間の絶縁信頼性試験を行った。1000時間後に線間絶縁抵抗値が1×104Ω以上であった場合は、絶縁信頼性が1000時間とした。試験途中に線間絶縁抵抗値が1×104Ω未満となった場合は、その時の試験時間を絶縁信頼性の値とした。銅櫛歯電極は、シリコン基板上に厚さ0.4μmの熱酸化膜、厚さ0.8μmの窒化珪素膜、厚さ0.08μmのクロム下地電極および厚さ10μmの銅電極が、この順に積層されたものをパターン加工したものを用いた。
(ポリイミドの重合)
300mlの4つ口フラスコに撹拌機、温度計、窒素導入管および滴下ロートを設置して、窒素雰囲気下、γBL92.60gおよびODPA31.02gを仕込み、60℃で撹拌溶解させた。その後、60℃で撹拌しながらMAP2.18g、SiDA1.24g、D−230 7.14gおよびBAHF20.14gを添加して、1時間撹拌した。その後180℃まで昇温して2時間撹拌した後、室温まで冷却して可溶性ポリイミド溶液A(固形分濃度40.0重量%)を得た。得られた可溶性ポリイミドの重量平均分子量は、20,050、イミド化率は95%であった。また、可溶性ポリイミドは水酸化テトラメチルアンモニウムの2.38%水溶液100gに25℃で0.1g以上溶解し、アルカリ可溶であった。
上記記載の方法により得られた可溶性ポリイミド溶液A 8.8gに、BP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2g、EP4003Sを2.5g、およびL1980を0.02g添加して混合撹拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
300mlの4つ口フラスコに撹拌機、温度計、窒素導入管および滴下ロートを設置して、窒素雰囲気下、γBL98.37gおよびODPA31.02gを仕込み、60℃で撹拌溶解させた。その後、60℃で撹拌しながらMAP2.18g、SiDA1.24gおよびBAHF31.13gを添加して1時間撹拌した。その後180℃まで昇温して2時間撹拌した後、室温まで冷却して可溶性ポリイミド溶液B(固形分濃度40.0重量%)を得た。得られた可溶性ポリイミドの重量平均分子量は、28,500、イミド化率は99%であった。また、可溶性ポリイミドは水酸化テトラメチルアンモニウムの2.38%水溶液100gに25℃で0.1g以上溶解し、アルカリ可溶であった。このようにして得られた可溶性ポリイミド溶液Bについて、実施例1と同様に各成分と混合し、感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性および接着強度の評価を行った。
実施例1で得られた可溶性ポリイミド溶液A 8.8gに、BP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2g、EP4003Sを1.5gおよびL1980を0.02g添加して混合撹拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
実施例1で得られた可溶性ポリイミド溶液A 8.8gに、BP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2g、EP4003Sを1.0gおよびL1980を0.02g添加して混合撹拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
実施例1で得られた可溶性ポリイミド溶液A 8.8gに、BP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2g、EP4000Sを1.0gおよびL1980を0.02g添加して混合撹拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
実施例1で得られた可溶性ポリイミド溶液A 8.8gに、BP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2g、EP4003Sを0.8gおよびL1980を0.02g添加して混合撹拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
300mlの4つ口フラスコに撹拌機、温度計、窒素導入管および滴下ロートを設置して、窒素雰囲気下、γBL88.75gおよびODPA31.02gを仕込み、60℃で撹拌溶解させた。その後、60℃で撹拌しながらMAP2.18g、SiDA1.24g、D−230 11.9gおよびBAHF12.82gを添加して1時間撹拌した。その後180℃まで昇温して2時間撹拌した後、室温まで冷却して可溶性ポリイミド溶液C(固形分濃度40.0重量%)を得た。得られた可溶性ポリイミドは水酸化テトラメチルアンモニウムの2.38%水溶液100gに25℃で0.1g以上溶解し、アルカリ可溶であった。得られた可溶性ポリイミドの重量平均分子量は、19,000であり、イミド化率は98%であった。このようにして得られた可溶性ポリイミド溶液Cについて、実施例6と同様に各成分と混合し、感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
300mlの4つ口フラスコに撹拌機、温度計、窒素導入管および滴下ロートを設置して、窒素雰囲気下、γBL101.46gおよびODPA31.02gを仕込み60℃で撹拌溶解させた。その後、60℃で撹拌しながらMAP2.18g、SiDA1.24g、D−400を13.05gおよびBAHF20.14gを添加して1時間撹拌した。その後180℃まで昇温して2時間撹拌した後、室温まで冷却して可溶性ポリイミド溶液D(固形分濃度40.0重量%)を得た。得られた可溶性ポリイミドの重量平均分子量は、19,950であり、イミド化率は99%であった。また、可溶性ポリイミドは水酸化テトラメチルアンモニウムの2.38%水溶液100gに25℃で0.1g以上溶解し、アルカリ可溶であった。このようにして得られた可溶性ポリイミド溶液Dについて、実施例6と同様に各成分と混合し、感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。解像度の評価をおこなった結果、75μmピッチ以下の微細なパターンで一部剥離していた。
300mlの4つ口フラスコに撹拌機、温度計、窒素導入管および滴下ロートを設置して、窒素雰囲気下、γBL96.06g、ODPA15.51gおよび6FDA22.21gを仕込み、60℃で撹拌溶解させた。その後、60℃で撹拌しながらMAP2.18g、SiDA1.24g、D−230 7.14gおよびBAHF20.14gを添加して1時間撹拌した。その後180℃まで昇温して2時間撹拌した後、室温まで冷却して可溶性ポリイミド溶液E(固形分濃度40.0重量%)を得た。得られた可溶性ポリイミドの重量平均分子量は、22,100であり、イミド化率は96%であった。また、可溶性ポリイミドは水酸化テトラメチルアンモニウムの2.38%水溶液100gに25℃で0.1g以上溶解し、アルカリ可溶であった。このようにして得られた可溶性ポリイミド溶液Eについて、実施例4と同様に各成分と混合し、感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
実施例1で得られた可溶性ポリイミド溶液A 8.8gにBP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2gおよびL1980を0.02g添加して混合撹拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。
300mlの4つ口フラスコに撹拌機、温度計、窒素導入管および滴下ロートを設置して、窒素雰囲気下、γBL86.89gおよびODPA31.02gを仕込み60℃で撹拌溶解させた。その後、60℃で撹拌しながらMAP2.18g、SiDA17.40gおよびBAHF7.33gを添加して1時間撹拌した。その後180℃まで昇温して2時間撹拌した後、室温まで冷却して可溶性ポリイミド溶液F(固形分濃度40.0重量%)を得た。得られた可溶性ポリイミドの重量平均分子量は、17,200であり、イミド化率は96%であった。また、可溶性ポリイミドは水酸化テトラメチルアンモニウムの2.38%水溶液100gに25℃で0.1g以上溶解せずアルカリ可溶性ではなかった。可溶性ポリイミド溶液Fについて、比較例1と同様に各成分と混合し、感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行った。ポリイミドFはアルカリ可溶性ではなかったため、パターンを形成することはできなかった。
300mlの4つ口フラスコに撹拌機、温度計、窒素導入管および滴下ロートを設置して、窒素雰囲気下、γBL99.04gおよびODPA31.02gを仕込み60℃で撹拌溶解させた。その後、60℃で撹拌しながらMAP2.18g、SiDA2.49g、MBAA8.59gおよびD−400 21.75gを添加して1時間撹拌した。その後180℃まで昇温して2時間撹拌した後、室温まで冷却して可溶性ポリイミド溶液G(固形分濃度40.0重量%)を得た。得られた可溶性ポリイミドの重量平均分子量は、16,800であり、イミド化率は99%であった。また、可溶性ポリイミドは水酸化テトラメチルアンモニウムの2.38%水溶液100gに25℃で0.1g以上溶解し、アルカリ可溶であった。このようにして得られた可溶性ポリイミド溶液Gについて、比較例1と同様に各成分と混合し、感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性、熱フロー量、接着強度および絶縁信頼性の評価を行おうとしたが、シリコンウェハへの貼り付けができなかった。
実施例2で得られた可溶性ポリイミド溶液B 8.8gに、BP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2g、EP4010Sを0.8gおよびL1980を0.02g添加して混合攪拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性および接着強度の評価を行った。EP4010Sはエポキシ化合物の2量体であり繰り返し長さが長いため、現像性が低下しパターンを形成することができなかった。
実施例2で得られた可溶性ポリイミド溶液B 8.8gに、BP−6EMを1.8g、DPE−6Aを0.2g、NCI831を0.2g、850Sを0.8gおよびL1980を0.02g添加して混合攪拌し、粘性液体である感光性接着剤組成物ワニスを得た。得られた感光性接着剤組成物について、上記の方法で、シリコンウェハへの貼り付け性、解像度、熱圧着性および接着強度の評価を行った。850Sはエポキシ化合物の親水性が低いため、現像性が低下しパターンを形成することができなかった。
Claims (7)
- 前記(A)エポキシ化合物の含有量が、(A)〜(C)成分の総量に対して15重量%以上50重量%以下である請求項1に記載の感光性接着剤組成物。
- 一般式(4)で示されるジアミンの残基が全ジアミン残基中に占める量が50mol%以下である請求項4に記載の感光性接着剤組成物。
- 請求項1〜5のいずれかに記載の感光性接着剤組成物の被膜が支持体上に形成された感光性接着剤シート。
- 請求項1〜5のいずれかに記載の感光性接着剤組成物の硬化物を介して、複数の基板または基板と他の部材が接着された半導体装置。
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JP2009021562A (ja) * | 2007-06-14 | 2009-01-29 | Toray Ind Inc | 半導体用接着シート、それを用いた半導体装置および半導体装置の製造方法 |
JP5458538B2 (ja) * | 2007-12-12 | 2014-04-02 | 日立化成株式会社 | 半導体装置及びその製造方法 |
JP5130939B2 (ja) * | 2008-02-13 | 2013-01-30 | 東レ株式会社 | 半導体用接着組成物およびそれを用いた半導体装置の製造方法 |
JP5353064B2 (ja) * | 2008-02-19 | 2013-11-27 | 日立化成株式会社 | 感光性接着剤組成物、これを用いて得られる接着フィルム、接着シート、接着剤パターン、及び半導体装置 |
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2010
- 2010-10-15 CN CN201080046229.9A patent/CN102575139B/zh active Active
- 2010-10-15 EP EP10824860.0A patent/EP2492331B1/en not_active Not-in-force
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- 2010-10-15 KR KR1020127012839A patent/KR101791710B1/ko active IP Right Grant
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Also Published As
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KR20130026524A (ko) | 2013-03-13 |
TW201122074A (en) | 2011-07-01 |
US20120181709A1 (en) | 2012-07-19 |
WO2011049011A1 (ja) | 2011-04-28 |
JP5887693B2 (ja) | 2016-03-16 |
EP2492331A4 (en) | 2016-09-07 |
CN102575139B (zh) | 2014-02-19 |
MY178933A (en) | 2020-10-23 |
TWI504713B (zh) | 2015-10-21 |
EP2492331A1 (en) | 2012-08-29 |
EP2492331B1 (en) | 2017-07-12 |
CN102575139A (zh) | 2012-07-11 |
KR101791710B1 (ko) | 2017-10-30 |
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