JP6845156B2 - 感光性ポリイミド組成物 - Google Patents
感光性ポリイミド組成物 Download PDFInfo
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- JP6845156B2 JP6845156B2 JP2017555469A JP2017555469A JP6845156B2 JP 6845156 B2 JP6845156 B2 JP 6845156B2 JP 2017555469 A JP2017555469 A JP 2017555469A JP 2017555469 A JP2017555469 A JP 2017555469A JP 6845156 B2 JP6845156 B2 JP 6845156B2
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- 239000000203 mixture Substances 0.000 title claims description 164
- 229920001721 polyimide Polymers 0.000 title claims description 96
- 239000004642 Polyimide Substances 0.000 title claims description 84
- 229920000642 polymer Polymers 0.000 claims description 234
- 239000010410 layer Substances 0.000 claims description 147
- 239000000758 substrate Substances 0.000 claims description 141
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 108
- 238000000034 method Methods 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 71
- 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 70
- 238000004090 dissolution Methods 0.000 claims description 59
- 238000010438 heat treatment Methods 0.000 claims description 58
- 150000004985 diamines Chemical class 0.000 claims description 54
- -1 3,4-dicarboxyphenyl Chemical group 0.000 claims description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 42
- 239000011241 protective layer Substances 0.000 claims description 37
- 125000000524 functional group Chemical group 0.000 claims description 26
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000004065 semiconductor Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 230000005855 radiation Effects 0.000 claims description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 6
- 229920003169 water-soluble polymer Polymers 0.000 claims description 6
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims description 5
- CGSKOGYKWHUSLC-UHFFFAOYSA-N 1-(4-aminophenyl)-1,3,3-trimethyl-2h-inden-5-amine Chemical group C12=CC=C(N)C=C2C(C)(C)CC1(C)C1=CC=C(N)C=C1 CGSKOGYKWHUSLC-UHFFFAOYSA-N 0.000 claims description 5
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical group C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 claims description 3
- GLQZKLVNEGUZHG-UHFFFAOYSA-N 1-(3-amino-4-methylphenyl)-1,3,3,6-tetramethyl-2h-inden-4-amine Chemical compound NC1=CC(C)=CC2=C1C(C)(C)CC2(C)C1=CC=C(C)C(N)=C1 GLQZKLVNEGUZHG-UHFFFAOYSA-N 0.000 claims description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- LBLCXNQFTZHQPG-UHFFFAOYSA-N 3,3,5-trimethyl-1,2-dihydroindene-4,6-diamine Chemical compound CC1=C(N)C=C2CCC(C)(C)C2=C1N LBLCXNQFTZHQPG-UHFFFAOYSA-N 0.000 claims description 3
- ZTECVWNTLJTZLK-UHFFFAOYSA-N 3,3,7-trimethyl-1,2-dihydroindene-4,6-diamine Chemical compound C1=C(N)C(C)=C2CCC(C)(C)C2=C1N ZTECVWNTLJTZLK-UHFFFAOYSA-N 0.000 claims description 3
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 3
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims description 3
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- CAJCGERRDZYERF-UHFFFAOYSA-N 7-ethyl-3,3-dimethyl-1,2-dihydroindene-4,6-diamine Chemical compound C1=C(N)C(CC)=C2CCC(C)(C)C2=C1N CAJCGERRDZYERF-UHFFFAOYSA-N 0.000 claims description 2
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 54
- 229920005575 poly(amic acid) Polymers 0.000 description 39
- 235000012431 wafers Nutrition 0.000 description 34
- 238000011161 development Methods 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000000576 coating method Methods 0.000 description 29
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 27
- 239000011248 coating agent Substances 0.000 description 26
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 17
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 16
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 16
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 16
- 239000010703 silicon Substances 0.000 description 16
- 229910052710 silicon Inorganic materials 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- 238000012545 processing Methods 0.000 description 14
- 239000003999 initiator Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000001459 lithography Methods 0.000 description 11
- 238000010907 mechanical stirring Methods 0.000 description 11
- 239000002105 nanoparticle Substances 0.000 description 11
- 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 10
- 150000008064 anhydrides Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002318 adhesion promoter Substances 0.000 description 9
- 230000000269 nucleophilic effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 9
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229940116333 ethyl lactate Drugs 0.000 description 8
- 238000003475 lamination Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 7
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000007906 compression Methods 0.000 description 6
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- 150000003949 imides Chemical group 0.000 description 6
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- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000005022 packaging material Substances 0.000 description 6
- 239000003504 photosensitizing agent Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000003851 corona treatment Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 239000004014 plasticizer Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- 239000004793 Polystyrene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
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- 239000000155 melt Substances 0.000 description 4
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XWUNIDGEMNBBAQ-UHFFFAOYSA-N Bisphenol A ethoxylate diacrylate Chemical compound C=1C=C(OCCOC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCCOC(=O)C=C)C=C1 XWUNIDGEMNBBAQ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 239000000853 adhesive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- CJYIPJMCGHGFNN-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic acid Chemical compound C1C2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O CJYIPJMCGHGFNN-UHFFFAOYSA-N 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 239000004033 plastic Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- JRDBISOHUUQXHE-UHFFFAOYSA-N pyridine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)N=C1C(O)=O JRDBISOHUUQXHE-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
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Classifications
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
-
- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
-
- 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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- 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
-
- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- 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
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- G—PHYSICS
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- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/805—Photosensitive materials characterised by the base or auxiliary layers characterised by stripping layers or stripping means
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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
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- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0387—Polyamides or polyimides
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- 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
- G03F7/16—Coating processes; Apparatus therefor
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- 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
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- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/34—Imagewise removal by selective transfer, e.g. peeling away
- G03F7/343—Lamination or delamination methods or apparatus for photolitographic photosensitive material
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- 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
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Description
本出願は、2015年12月4日に出願された米国仮出願第62/263,372号、2015年6月26日に出願された米国仮出願第62/185,424号及び2015年4月21日に提出された米国仮出願第62/150,381号の優先権を主張する。先行出願は、参照によりその全体が本明細書に組み込まれている。
式中、R1、R2、R3、R4、R5、R11、R12、R13及びR14は、それぞれ独立に、Hであるか、置換若しくは非置換のC1−C6の直鎖若しくは分枝のアルキル基であるか、又はC5−C7シクロアルキル基である。
式中、R1、R2、R3、R4、R5、R11、R12、R13及びR14は、それぞれ独立に、Hであるか、置換若しくは非置換のC1−C6の直鎖若しくは分枝のアルキル基であるか、又はC5−C7シクロアルキル基である。
式中、R15、R16、R17及びR18はそれぞれ独立して、H、置換若しくは非置換のC1−C6直鎖若しくは分枝アルキル基、又はC5−C7シクロアルキル基である。いくつかの実施形態において、R15、R16、R17及びR18のうち少なくとも3つは水素ではない。
式中、R41及びR42は、それぞれ独立して2価の脂肪族又は芳香族基であり、R43、R44、R45及びR46は、それぞれ独立して1価の脂肪族又は芳香族基であり、mは1〜100の整数である。
式中、Gは−O−、−(NR25)−、−[C(R26)=C(R27)]−又は−[C=C(R28)2]−であり、ここでR25、R26、R27及びR28はそれぞれ独立して、H、置換若しくは非置換C1−C12直鎖、分枝単環式若しくは多環式アルキル基又は置換若しくは非置換フェニル基であり、R21、R22、R23及びR24はそれぞれ独立して、H、置換又は非置換C1−C12直鎖、分枝単環式若しくは多環式アルキル基、置換又は非置換フェニル基、OR29、CH2OR30、CH2OC(=O)R31、CH2C(=O)OR32、CH2NHR33、CH2NHC(=O)R34、CH2C(=O)N(R35)2、C(=O)OR36であり、ここでR29、R30、R31、R32、R33、R34、R35及びR36はそれぞれ独立して、H又は置換若しくは非置換C1−C6直鎖、分枝若しくは単環式アルキル基である。
本開示のいくつかの実施形態は、キャリア基板と、キャリア基板によって支持されるポリマー層(例えば感光性ポリマー層)と、を含むドライフィルム構造体に関する。ポリマー層は、本明細書に記載の感光性組成物(例えば上記の成分(A)、(B)及び(C)を含有する感光性組成物)から形成することができ、シクロペンタノン中での前記ポリマー層の溶解速度は、約0.15μm/秒を超える。いくつかの実施形態において、ドライフィルムは、ポリマー層がキャリア基板と保護層の間になるように保護層をさらに含むことができる。
合成例1(P−1)
6FDA/DAPIポリイミドの調製
ポリマー溶液(P−1)26.72g、GBL4.81g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、パラベンゾキノン0.02g、1,6−ヘキサンジオールジアクリレート2.70g及びペンタエリスリトールトリアクリレート0.9gを使用することによって、感光性組成物FE−1を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
4枚のシリコンウェハに感光性組成物をスピンコートして、厚さ約15μmのコーティングを形成した。コートしたウェハを、ホットプレートを使用して95℃にて180秒間乾式加熱した。ウェハはシクロペンタノンを使用することによって15秒間、25秒間、35秒間及び65秒間現像した(各現像時間に1枚)。現像剤15ミリリットルを10秒間でウェハ上にストリーム分注(stream dispensed)してフィルムを完全に被覆し、その上に現像剤のパドルを形成し、25℃にてパドル現像を開始した(15秒、25秒、35秒及び65秒。記載した現像時間は、ストリーム分注を中止した後の時間である。)。分注工程及び現像工程の間に、ウェハを100RPMの回転速度で回転させた。現像剤のパドルを除去し、残りのフィルムを3000RPMの回転速度で15秒間回転させることによって乾燥させた。各ウェハのフィルム厚損失を測定し、厚み損失対現像時間のグラフをプロットした。フィルム厚はDektak IIA Profilometerを用いて測定した。データを線形関数に当てはめて、線の傾きを求め、これにより代表的な溶解速度を求めた。
感光性組成物FE−1の溶解速度を、溶解速度測定の一般手順に従って測定した。結果を表2に示す。計算した溶解速度は約0.21μm/秒であった。
ポリマー溶液(P−1)26.72g、GBL4.81g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、パラベンゾキノン0.02g及び1,6−ヘキサンジオールジアクリレート3.60gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
溶解速度測定の一般手順に従って測定した感光性組成物FE−2の溶解速度は、0.59μm/秒であった。
SSC量の関数としてのフィルムの溶解速度の効果
ポリマー溶液(P−1)26.72g、GBL4.81g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、パラベンゾキノン0.02g及び1,6−ヘキサンジオールジアクリレート1.20gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5μmのシリンジフィルタを使用して溶液を濾過した。
溶解速度測定の一般手順に従って測定した感光性組成物CFE−1の溶解速度は0.05μm/秒であった。
ポリマー溶液(P−1)26.72g、GBL4.81g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、パラベンゾキノン0.02g、ビスフェノールAエトキシレートジアクリレート3.70g及びペンタエリスリトールトリアクリレート0.9gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
溶解速度測定の一般手順に従って測定した感光性組成物FE−3の溶解速度は0.88μm/秒であった。
溶解度スイッチング化合物(SSC)量の関数としてのフィルムの溶解速度の効果
ポリマー溶液(P−1)26.72g、GBL3.22g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、パラベンゾキノン0.02g及びビスフェノールAエトキシレートジアクリレート2.80gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
溶解速度測定の一般手順に従って測定した感光性組成物CFE−2の溶解速度は0.09μm/秒であった。
溶解度スイッチング化合物(SSC)量の関数としてのフィルムの溶解速度の効果
ポリマー溶液(P−1)26.72g、GBL1.64g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、パラベンゾキノン0.02g及びビスフェノールAエトキシレートジアクリレート2.00gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
溶解速度測定の一般手順に従って測定した感光性組成物CFE−3の溶解速度は0.11μm/秒であった。
2種のモノマーのモル比を1:1としたことを除いて合成例1を反復し、ポリマーを水中に沈殿させて単離した。水の量は、反応混合物の体積の10倍であった。水/メタノールの1:1混合物を用いて再スラリー化することによって、ポリマーをさらに精製した。得られたポリマーの重量平均分子量(Mw)は88,000ダルトンであった。
分子量(Mw)の効果
ポリマー((CP−1、Mw=88,000ダルトン)8.00g、GBL21.95g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、テトラエチレングリコールジアクリレート2.70g及びペンタエリスリトールトリアクリレート0.9gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
感光性組成物CFE−4をシリコンウェハ上にスピンコートし、ホットプレートを使用して95℃にて180秒間乾式加熱して、厚さ約15μmのコーティングを形成した。露光用の所望のパターンを有するマスクを介して、広帯域UV露光ツール(Carl Suss MA−56)を用いて感光性ポリイミドフィルムを露光した。露光後、露光フィルムを50℃にて3分間加熱した。
高分子量(Mw)の効果
ポリマー((CP−1、Mw=88,000ダルトン)8.00g、GBL21.95g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g及びテトラエチレングリコールジアクリレート2.80gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
感光性組成物CFE−5をシリコンウェハ上にスピンコートして、厚さ約15μmのコーティングを形成した。コートしたウェハを95℃にて180秒間乾式加熱した。露光用の所望のパターンを有するマスクを介して、広帯域UV露光ツール(Carl Suss MA−56)を用いて感光性ポリイミドフィルムを露光した。露光後、露光フィルムを50℃にて3分間加熱した。
ポリマー溶液(P−1)26.72g、GBL4.81g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g、パラベンゾキノン0.02g及びテトラエチレングリコールジアクリレート2.80gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
感光性組成物FE−4をシリコンウェハ上にスピンコートし、ホットプレートを使用して95℃にて180秒間乾式加熱して、厚さ約15μmのコーティングを形成した。露光用の所望のパターンを有するマスクを介して、広帯域UV露光ツール(Carl Suss MA−56)を用いて感光性ポリイミドフィルムを露光した。露光後、露光フィルムを50℃にて3分間加熱した。
2種のモノマー6FDAとDAPIとの比を11/12としたことを除いて合成例2を反復し、ポリマーを水中に沈殿させて単離した。得られたポリマーの重量平均分子量(Mw)は13,500ダルトンであった。
低分子量(Mw)の効果
ポリマー((P−2、Mw=13,500ダルトン)8.00g、GBL21.95g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.48g、γ−グリシドキシプロピルトリメトキシシラン0.24g、NCI−831(商品名、ADEKA社より入手可能)0.24g及びテトラエチレングリコールジアクリレート2.80gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
感光性組成物CFE−6をシリコンウェハ上にスピンコートして、厚さ約15μmのコーティングを形成した。コートしたウェハを95℃にて180秒間乾式加熱した。露光用の所望のパターンを有するマスクを介して、広帯域UV露光ツール(Carl Suss MA−56)を用いて感光性ポリイミドフィルムを露光した。露光後、露光フィルムを50℃にて3分間加熱した。
ポリマー溶液(P−1)38.71g、GBL8.6g、PolyFox6320(OMNOVA Solutionsから入手可能)の0.5重量%GBL溶液0.75g、メタクリロキシプロピルトリメトキシシラン0.63g、NCI−831(商品名、ADEKA社より入手可能)0.38g、パラベンゾキノン0.03g、テトラエチレングリコールジアクリレート4.22g及びペンタエリスリトールトリアクリレート1.41gを使用することによって、感光性組成物を調製した。24時間機械撹拌した後、5ミクロンのシリンジフィルタを使用して溶液を濾過した。
溶解速度測定の一般手順に従って測定した感光性組成物FE−5の溶解速度は0.37μm/秒であった。
組成物FE−5の調製を5倍大の規模で反復し、0.2μmフィルタ(Meissner Filtration Product,Inc.製Ultradyne、カタログ番号CFTM10.2−44B1)を使用して組成物を濾過した。濾過した感光性溶液を、2フィート/分(60cm/分)のライン速度で、富士フイルムUSA(グリーンウッド、サウスカロライナ州)製のリバース・マイクロバー・コーターを使用して、30umのマイクロバー隙間を空けて、キャリア基板として用いる幅16.2インチ及び厚さ35μmのポリエチレンテレフタレート(PET)フィルム(TA30、東レ・プラスチックス・アメリカ社製)上に適用し、210°Fにて乾燥させて、厚さおよそ5.0μmの感光性ポリマー層を得た。このポリマー層上に、幅18インチ、厚さ20μmの二軸配向ポリプロピレンフィルム(BOPP、Mirwec Film Inc,ブルーミントン、インディアナ州、商品名ボプロン)をロール圧縮により積層して保護層として作用させた。
組成物FE−5の調製を5倍大の規模で反復し、0.2μmフィルタ(Meissner Filtration Product,Inc.製Ultradyne、カタログ番号CFTM10.2−44B1)を使用して組成物を濾過した。濾過した感光性溶液を、2フィート/分(60cm/分)のライン速度で、富士フイルムUSA(グリーンウッド、サウスカロライナ州)製のリバース・マイクロバー・コーターを使用して、60umのマイクロバー間隙を空けて、キャリア基板として用いる幅16.2インチ及び厚さ35μmのポリエチレンテレフタレート(PET)フィルム(TA30、東レ・プラスチックス・アメリカ社製)上に適用し、210°Fで乾燥させて、厚さおよそ10.0μmの感光性ポリマー層を得た。このポリマー層上に、幅18インチ、厚さ20μmの二軸配向ポリプロピレンフィルム(BOPP、Mirwec Film Inc,ブルーミントン、インディアナ州、商品名ボプロン)をロール圧縮により積層して保護層として作用させた。
剥離により保護層を除去した後、ドライフィルム構造体DF−1(6インチ×6インチ)の感光性ポリマー層を4インチWafernet銅コートウェハ上に配置した。ポリマー層を真空積層(0.2〜0.4トル)により20秒間にわたって、銅コートウェハ上に積層し、続いて40psiの圧力及び0.2〜0.4トルの真空の両方に70秒間供した。積層温度は90℃であった。積層方法は、ニュージャージー州OPTEK製のDPL−24A差圧積層装置を使用して行った。
実施例L1の組成物DF−1によって積層した銅ウェハのキャリア基板を除去した。次いで、開始露光エネルギー50mJ/cm2とし、露光エネルギーを50mJ/cm2刻みで上昇させるパターン化露光アレイにてi線ステッパを利用して、感光性ポリマー層を活性線に露光した。次いで、露光フィルムを50℃にて3分間加熱し、シクロペンタノンを使用して2度の75秒パドルにより現像した。次にフィルムをPGMEAで15秒間洗浄した。100mJ/cm2のエネルギー線量で、2μmの分解能を有するレリーフパターンを得た。フィルム厚損失は26.7%であった。
Claims (42)
- 30,000ダルトン〜70,000ダルトンの範囲の重量平均分子量を有する少なくとも1種の完全イミド化ポリイミドポリマー;
少なくとも1種の溶解度スイッチング化合物;
少なくとも1種の光開始剤;および
少なくとも1種の溶剤
を含む感光性組成物であって、
前記少なくとも1種の完全イミド化ポリイミドポリマーが、少なくとも1種のジアミンから調製され、前記少なくとも1種のジアミンが、構造(Ia)のジアミン及び構造(Ib)のジアミンからなる群より選択される化合物を含み、
式中、R 1 、R 2 、R 3 、R 4 、R 5 、R 11 、R 12 、R 13 及びR 14 は、それぞれ独立に、Hであるか、置換若しくは非置換のC 1 −C 6 の直鎖若しくは分枝のアルキル基であるか、又はC 5 −C 7 シクロアルキル基であり、
前記感光性組成物は、シクロペンタノンを現像剤として使用した場合に0.15μm/秒を超える溶解速度を示すフィルムを形成することができる、
感光性組成物。 - 前記少なくとも1種のジアミンが、1−(4−アミノフェニル)−1,3,3−トリメチルインダン−5−アミン、5−アミノ−6−メチル−1−(3’−アミノ−4’−メチルフェニル)−1,3,3−トリメチルインダン、4−アミノ−6−メチル−1−(3’−アミノ−4’−メチルフェニル)−1,3,3−トリメチルインダン、5,7−ジアミノ−1,1−ジメチルインダン、4,7−ジアミノ−1,1−ジメチルインダン、5,7−ジアミノ−1,1,4−トリメチルインダン、5,7−ジアミノ−1,1,6−トリメチルインダン及び5,7−ジアミノ−1,1−ジメチル−4−エチルインダンからなる群より選択される、請求項1に記載の感光性組成物。
- 前記少なくとも1種の完全イミド化ポリイミドポリマーが、少なくとも1種の二無水物から調製され、前記少なくとも1種の二無水物が、2,2−[ビス(3,4−ジカルボキシフェニル)]ヘキサフルオロプロパン二無水物、3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物、3,3’,4,4’−ジフェニルスルホンテトラカルボン酸二無水物及び3,3’,4,4’−ジフェニルエーテルテトラカルボン酸二無水物からなる群より選択される化合物を含む、請求項1に記載の感光性組成物。
- 前記少なくとも1種の完全イミド化ポリイミドポリマーがフッ素化二無水物から調製される、請求項3に記載の感光性組成物。
- 前記フッ素化二無水物が下記化合物からなる群より選択される、請求項4に記載の感光性組成物。
- 前記少なくとも1種の完全イミド化ポリイミドポリマーが、構造(Ia)のジアミン及び構造(Ib)のジアミンからなる群より選択される少なくとも1種のジアミンと、2,2−[ビス(3,4−ジカルボキシフェニル)]ヘキサフルオロプロパン二無水物と、から調製される、請求項1に記載の感光性組成物。
- 前記溶解度スイッチング化合物が、ビニル基、アリル基、ビニルエーテル基、プロペニルエーテル基、(メタ)アクリロイル基、SiH基及びチオール基からなる群より選択される少なくとも1個の官能基を含む、請求項1に記載の感光性組成物。
- 前記溶解度スイッチング化合物が、1,6−ヘキサンジオールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ジビニルベンゼン、エトキシル化ビスフェノール−A−ジ(メタ)アクリレート、ジエチレングリコールビス(アリルカーボネート)、トリメチロールプロパントリ(メタ)アクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ/ヘキサ(メタ)アクリレート、イソシアヌレートトリ(メタ)アクリレート、ビス(2−ヒドロキシエチル)イソシアヌレートジ(メタ)アクリレート、1,3−ブタンジオールトリ(メタ)アクリレート、1,4−ブタンジオールトリ(メタ)アクリレート、メチル(メタ)アクリレート、ブチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、ベンジル(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、(メタ)アクリレート変性尿素ホルムアルデヒド樹脂、(メタ)アクリレート変性メラミンホルムアルデヒド樹脂及び(メタ)アクリレート変性セルロースからなる群より選択される、請求項7に記載の感光性組成物。
- 前記現像剤及び前記少なくとも1種の完全イミド化ポリイミドポリマーの相対エネルギー差が0.1〜3である、請求項1に記載の感光性組成物。
- 前記感光性組成物から製造されたフィルムの領域を100mJ/cm 2 〜1,000mJ/cm 2 の照射線量で活性線に露光した場合、露光した前記領域がシクロペンタノン中で0.02μm/秒未満の溶解速度を示す、請求項1に記載の感光性組成物。
- 前記溶解度スイッチング化合物は、シクロペンタノン中におけるフィルムの溶解速度を、前記溶解度スイッチング化合物を含まない以外は含有成分が同じである感光性組成物から製造されたフィルムに比して増加させる、請求項1に記載の感光性組成物。
- 請求項1〜請求項11のいずれか一項に記載の感光性組成物から形成された感光性フィルム。
- 請求項1〜請求項11のいずれか一項に記載の感光性組成物で基板をコーティングして、フィルムを前記基板の上に有するコート基板を形成すること;及び
前記コート基板を乾式加熱して、乾燥したフィルムを有するコート基板を形成すること
を含む方法。 - 前記コート基板は50℃〜200℃の温度にて乾式加熱される、請求項13に記載の方法。
- マスクを介して前記乾燥されたフィルムを放射線に露光し、乾燥され且つパターン状に露光されたフィルムを有するコート基板を形成することをさらに含む、請求項14に記載の方法。
- 第2の乾式加熱工程で、前記乾燥され且つパターン状に露光されたフィルムを50℃〜150℃の温度にて乾式加熱することをさらに含む、請求項15に記載の方法。
- 前記乾燥され且つパターン状に露光されたフィルムの一部を現像剤で現像して、前記基板の上にレリーフ画像を生成することをさらに含む、請求項16に記載の方法。
- 前記基板の上の前記レリーフ画像を溶剤又は溶剤混合物ですすぐことをさらに含む、請求項17に記載の方法。
- 第3の乾式加熱工程で、前記レリーフ画像を有する基板を50℃〜200℃の温度にて乾式加熱することをさらに含む、請求項18に記載の方法。
- 請求項13に記載の方法によって形成された少なくとも1つのパターン形成フィルムを含む三次元物体。
- 2つ以上の積層体をなす複数の前記パターン形成フィルムを含む、請求項20に記載の三次元物体。
- 3つ以上の積層体をなす複数の前記パターン形成フィルムを含む、請求項20に記載の三次元物体。
- 請求項20に記載の三次元物体を含む半導体デバイス。
- 集積回路、発光ダイオード、太陽電池又はトランジスタである、請求項23に記載の半導体デバイス。
- キャリア基板、及び
前記キャリア基板によって支持された第1のポリマー層
を含み、前記第1のポリマー層が請求項1〜請求項11のいずれか一項に記載の感光性組成物から作製される、ドライフィルム構造体。 - 保護層をさらに含み、前記第1のポリマー層が前記キャリア基板と前記保護層との間にある、請求項25に記載のドライフィルム構造体。
- 前記第1のポリマー層が5μm以下のフィルム厚さを有する、請求項25に記載のドライフィルム構造体。
- 第2のポリマー層をさらに含み、前記第2のポリマー層が前記第1のポリマー層と前記キャリア基板との間にあるか、または前記第2のポリマー層が前記第1のポリマー層と前記保護層との間にある、請求項26に記載のドライフィルム構造体。
- 前記第2のポリマー層が水溶性ポリマーを含有する、請求項28に記載のドライフィルム構造体。
- 請求項25に記載のドライフィルム構造体を電子基板上に適用して積層体を形成することを含む方法。
- 前記積層体の中の前記第1のポリマー層を活性線で露光することをさらに含む、請求項30に記載の方法。
- 前記第1のポリマー層を露光する前又は後に前記キャリア基板を除去することをさらに含む、請求項31に記載の方法。
- 現像剤を使用して前記第1のポリマー層の未露光部分を除去することをさらに含む、請求項32に記載の方法。
- 前記第1のポリマー層の残存する露光部分を乾式加熱することをさらに含む、請求項33に記載の方法。
- 請求項30に記載の方法によって形成された、三次元物体。
- 請求項35に記載の三次元物体を含む半導体デバイス。
- 集積回路、発光ダイオード、太陽電池又はトランジスタである、請求項36に記載の半導体デバイス。
- (a)キャリア基板、
保護層、及び
前記キャリア基板と前記保護層との間にあり、30,000ダルトン〜70,000ダルトンの範囲の重量平均分子量を有する少なくとも1種の完全イミド化ポリイミドポリマーと、少なくとも1種の溶解度スイッチング化合物と、少なくとも1種の光開始剤とを含む感光性ポリマー層
を含む、ドライフィルム構造体であって、
前記少なくとも1種の完全イミド化ポリイミドポリマーが、少なくとも1種のジアミンから調製され、前記少なくとも1種のジアミンが、構造(Ia)のジアミン及び構造(Ib)のジアミンからなる群より選択される化合物を含み、
式中、R 1 、R 2 、R 3 、R 4 、R 5 、R 11 、R 12 、R 13 及びR 14 は、それぞれ独立に、Hであるか、置換若しくは非置換のC 1 −C 6 の直鎖若しくは分枝のアルキル基であるか、又はC 5 −C 7 シクロアルキル基である、
ドライフィルム構造体を提供すること;
(b)前記ドライフィルム構造体から前記保護層を除去すること;
(c)工程(b)で得た構造体を電子基板の上に適用して、前記電子基板と前記キャリア基板との間に前記感光性ポリマー層を含む積層体を形成すること;及び
(d)前記感光性ポリマー層をパターン形成層に変換すること、
を含み、前記パターン形成層が5μm以下の厚さを有し且つ3μm以下の加工寸法(feature size)を有する少なくとも1つの素子を含む、方法。 - 前記パターン形成層が4μm以下の厚さを有する、請求項38に記載の方法。
- 前記パターン形成層が3μm以下の厚さを有する、請求項39に記載の方法。
- 前記パターン形成層が2μm以下の加工寸法(feature size)を有する少なくとも1つの素子を含む、請求項38に記載の方法。
- 30,000ダルトン〜70,000ダルトンの範囲の重量平均分子量を有する少なくとも1種の完全イミド化ポリイミドポリマー;
少なくとも1種の溶解度スイッチング化合物;
少なくとも1種の光開始剤;及び
少なくとも1種の溶剤
を含む感光性組成物であって、
前記少なくとも1種の完全イミド化ポリイミドポリマーが、少なくとも1種のジアミンから調製され、前記少なくとも1種のジアミンが、構造(Ia)のジアミン及び構造(Ib)のジアミンからなる群より選択される化合物を含み、
式中、R 1 、R 2 、R 3 、R 4 、R 5 、R 11 、R 12 、R 13 及びR 14 は、それぞれ独立に、Hであるか、置換若しくは非置換のC 1 −C 6 の直鎖若しくは分枝のアルキル基であるか、又はC 5 −C 7 シクロアルキル基であり、
前記感光性組成物は、シクロペンタノンを現像剤として使用した場合に0.15μm/秒を超える溶解速度を示すフィルムを形成することができ、
前記溶解度スイッチング化合物は、シクロペンタノン中におけるフィルムの溶解速度を、前記溶解度スイッチング化合物を含まない以外は含有成分が同じである感光性組成物から製造されたフィルムに比して増加させる、
感光性組成物。
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CN108027563B (zh) | 2021-12-03 |
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PH12017501907A1 (en) | 2018-03-05 |
CN108027563A (zh) | 2018-05-11 |
EP3286605A1 (en) | 2018-02-28 |
US20160313641A1 (en) | 2016-10-27 |
KR20180022644A (ko) | 2018-03-06 |
JP2018517168A (ja) | 2018-06-28 |
WO2016172092A1 (en) | 2016-10-27 |
WO2016172089A1 (en) | 2016-10-27 |
TWI733665B (zh) | 2021-07-21 |
US20200218152A1 (en) | 2020-07-09 |
US20160313642A1 (en) | 2016-10-27 |
KR102540243B1 (ko) | 2023-06-02 |
EP3286606B1 (en) | 2022-12-28 |
EP3286606A1 (en) | 2018-02-28 |
EP3286606A4 (en) | 2019-01-16 |
JP2018517169A (ja) | 2018-06-28 |
KR20180022645A (ko) | 2018-03-06 |
EP3286605B1 (en) | 2023-06-28 |
US11899364B2 (en) | 2024-02-13 |
PH12017501936A1 (en) | 2018-03-19 |
TW201704343A (zh) | 2017-02-01 |
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JP2021047425A (ja) | 2021-03-25 |
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