US20140374887A1 - Composition for forming passivation film, including resin having carbon-carbon multiple bond - Google Patents
Composition for forming passivation film, including resin having carbon-carbon multiple bond Download PDFInfo
- Publication number
- US20140374887A1 US20140374887A1 US14/374,668 US201314374668A US2014374887A1 US 20140374887 A1 US20140374887 A1 US 20140374887A1 US 201314374668 A US201314374668 A US 201314374668A US 2014374887 A1 US2014374887 A1 US 2014374887A1
- Authority
- US
- United States
- Prior art keywords
- group
- formula
- passivation film
- composition
- forming
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 130
- 238000002161 passivation Methods 0.000 title claims abstract description 93
- 229920005989 resin Polymers 0.000 title description 22
- 239000011347 resin Substances 0.000 title description 22
- 239000011203 carbon fibre reinforced carbon Substances 0.000 title description 11
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 93
- 125000000732 arylene group Chemical group 0.000 claims abstract description 41
- 125000001424 substituent group Chemical group 0.000 claims abstract description 32
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 24
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 21
- 125000003277 amino group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 15
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000005336 allyloxy group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 125000000565 sulfonamide group Chemical group 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
- 125000004653 anthracenylene group Chemical group 0.000 claims description 4
- 229920001519 homopolymer Polymers 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 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 238000009413 insulation Methods 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 279
- -1 fluoromethylene group Chemical group 0.000 description 141
- 239000000243 solution Substances 0.000 description 137
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 88
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 78
- 238000006243 chemical reaction Methods 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- 150000001875 compounds Chemical class 0.000 description 42
- 239000000843 powder Substances 0.000 description 42
- 229910000027 potassium carbonate Inorganic materials 0.000 description 39
- 239000011259 mixed solution Substances 0.000 description 31
- 230000002378 acidificating effect Effects 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 229920002521 macromolecule Polymers 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000004793 Polystyrene Substances 0.000 description 23
- 229920002223 polystyrene Polymers 0.000 description 23
- 235000012431 wafers Nutrition 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 229910001873 dinitrogen Inorganic materials 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 17
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 17
- 150000001721 carbon Chemical group 0.000 description 15
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 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 10
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 238000012644 addition polymerization Methods 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 238000001312 dry etching Methods 0.000 description 8
- 125000000962 organic group Chemical group 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 6
- DPVJEOQNNXOAIN-UHFFFAOYSA-N C.C1=CC=CC=C1.C1=CC=CC=C1.C1=CC=CC=C1.CC.CC.CC.CC.CC.CC.CC.CCC Chemical compound C.C1=CC=CC=C1.C1=CC=CC=C1.C1=CC=CC=C1.CC.CC.CC.CC.CC.CC.CC.CCC DPVJEOQNNXOAIN-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- ROWWOBXWBIHFLG-UHFFFAOYSA-N CC#CC.CC(C)C=CC(C)C Chemical compound CC#CC.CC(C)C=CC(C)C ROWWOBXWBIHFLG-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000004696 Poly ether ether ketone Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005304 joining Methods 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920002530 polyetherether ketone Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 description 2
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 2
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- UYKJIHUGJSCCQC-UHFFFAOYSA-N C.C1=CC=CC=C1.C1=CC=CC=C1.CC.CC.CC.CC.CCC Chemical compound C.C1=CC=CC=C1.C1=CC=CC=C1.CC.CC.CC.CC.CCC UYKJIHUGJSCCQC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N c1ccccc1 Chemical compound c1ccccc1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- YDSPXEVWSDMKEJ-UHFFFAOYSA-N n-anthracen-1-ylprop-2-enamide Chemical compound C1=CC=C2C=C3C(NC(=O)C=C)=CC=CC3=CC2=C1 YDSPXEVWSDMKEJ-UHFFFAOYSA-N 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 229920005649 polyetherethersulfone Polymers 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
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- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
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- OEZWIIUNRMEKGW-UHFFFAOYSA-N (2-bromophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1Br OEZWIIUNRMEKGW-UHFFFAOYSA-N 0.000 description 1
- HZBSQYSUONRRMW-UHFFFAOYSA-N (2-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1O HZBSQYSUONRRMW-UHFFFAOYSA-N 0.000 description 1
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 description 1
- YRPLSAWATHBYFB-UHFFFAOYSA-N (2-methyl-2-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)(OC(=O)C=C)C2C3 YRPLSAWATHBYFB-UHFFFAOYSA-N 0.000 description 1
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 description 1
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AXTADRUCVAUCRS-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrole-2,5-dione Chemical compound OCCN1C(=O)C=CC1=O AXTADRUCVAUCRS-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
-
- 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
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09D161/16—Condensation polymers of aldehydes or ketones with phenols only of ketones with phenols
-
- 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
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C09D171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C09D171/12—Polyphenylene oxides
-
- 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
- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/06—Polysulfones; Polyethersulfones
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02296—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer
- H01L21/02318—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- 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
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/70—Manufacture or treatment of devices consisting of a plurality of solid state components formed in or on a common substrate or of parts thereof; Manufacture of integrated circuit devices or of parts thereof
- H01L21/71—Manufacture of specific parts of devices defined in group H01L21/70
- H01L21/768—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics
- H01L21/76898—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics formed through a semiconductor substrate
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
- H01L23/3157—Partial encapsulation or coating
- H01L23/3171—Partial encapsulation or coating the coating being directly applied to the semiconductor body, e.g. passivation layer
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/48—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor
- H01L23/481—Internal lead connections, e.g. via connections, feedthrough structures
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/02—Semiconductor bodies ; Multistep manufacturing processes therefor
- H01L29/06—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by their shape; characterised by the shapes, relative sizes, or dispositions of the semiconductor regions ; characterised by the concentration or distribution of impurities within semiconductor regions
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- the present invention relates to an insulating film and particularly to a passivation film protecting an electrode on the rear surface of a wafer formed by the through silicon via (TSV) technology in a step in which lamination bodies such as semiconductor products, for example, IC chips, and optical products are formed.
- TSV through silicon via
- One example of methods for producing stack structures is a method including steps of: thinning a wafer on which a semiconductor element is formed; providing a through-hole with a technique such as anisotropic dry etching (through silicon via: TSV technique); forming an electrode on the rear surface of the wafer by filling the through-hole with a conductive material such as copper; forming a passivation film on the rear surface having an electrode; and electrically joining the wafer and a chip or the surface of a wafer on which another semiconductor element is formed.
- a technique such as anisotropic dry etching (through silicon via: TSV technique)
- the insulating film formed on the rear surface of a wafer is required to be electrically insulative to prevent current leakage and migration of a conductive material, to be solvent-tolerant and have a good dry etch back property in a photolithography step that is to open an electrode portion after forming a passivation film, and to be heat-tolerant in an electrode-joining step.
- passivation films examples include benzocyclobutene resins, polyimides, and fully aromatic polyethers.
- benzocyclobutene resins require a fluorine gas to be used for dry etch back in a photolithography step, and thus electrodes and wafers may be damaged.
- cross-linking reaction does not sufficiently proceed at a curing temperature around 200° C., and a good solvent-tolerance cannot be obtained.
- thinned wafers may be damaged because the film-forming temperature is 300° C. or higher, and shrinkage of films upon curing results in remaining stresses.
- Fully aromatic polyethers have no heat cross-linking portion, and thus are not highly tolerant of solvents.
- resins may be melted in joining electrodes because the resins have low softening points.
- Patent Document 1 A substrate for a thick film technique has been disclosed (Patent Document 1).
- an undercoat film containing 30% by volume to 45% by volume of a polyether ether ketone resin powder and a thermosetting resin is formed on an inorganic insulating substrate that is a glass base material impregnated with a silicone resin.
- Covering products such as an adhesive for flexible printed-circuit boards, that contain a polymer having a main chain composed of a polyimide, and having a functional group having a carbon-carbon triple bond at an end thereof, have been disclosed (Patent Document 2).
- Covering products such as an adhesive composition containing a polymer having a main chain containing a functional group having a phenyl group, urea, an amido group and the like, and a carbon-carbon triple bond, have been disclosed (Patent Document 3).
- Covering products such as an adhesive composition containing a polymer containing polyether ether sulfone having a sulfonic acid group, and containing polyether ether ketone, have been disclosed (Patent Document 4).
- Patent Document 1 Japanese Patent Application Publication No. 2009-070875 (JP 2009-070875 A)
- Patent Document 2 WO 2006-137369
- Patent Document 3 Japanese Patent Application Publication No. 2010-065097 (JP 2010-065097 A)
- Patent Document 4 Japanese Patent Application Publication No. 2005-264008 (JP 2005-264008 A)
- the present invention provides: as a first aspect, a composition for forming a passivation film, comprising: a polymer containing a unit structure of Formula (i):
- T 0 is a sulfonyl group, a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group
- the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at an end, in a side chain, or in a main chain of the polymer:
- composition for forming a passivation film comprising: a polymer containing a unit structure of Formula (1):
- L 1 is an arylene group optionally having a substituent, or is a combination of an arylene group optionally having a substituent and a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and T 1 is a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group, or is a combination of an arylene group optionally having a substituent, a fluoroalkylene group, and a cycloalkylene group), in which the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at an end, in a
- the composition for forming a passivation film according to the first aspect or the second aspect in which the arylene group is a phenylene group, a naphthylene group, or an anthrylene group;
- composition for forming a passivation film according to any one of the first aspect to the third aspect, in which the polymer is a homopolymer having one type of unit structure;
- composition for forming a passivation film according to any one of the first aspect to the third aspect, in which the polymer is a copolymer having at least two types of unit structures;
- composition for forming a passivation film comprising: a polymer containing a unit structure of Formula (1) where L 1 is a group of Formula (3) below, a unit structure of Formula (1) where L 1 is a group of Formula (4) below, or a combination of these unit structures:
- R 1 , R 2 , and R 3 is a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups;
- L 2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4);
- composition for forming a passivation film comprising: a polymer containing a unit structure of Formula (1) where T 1 is a group of Formula (5) below, a unit structure of Formula (1) where T 1 is a group of Formula (6) below, or a combination of these unit structures:
- R 4 , R 5 , and R 6 is a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups;
- T 2 is a fluoroalkylene group, a cycloalkylene group, or a combination of these groups; and each of n4, n5, and n6 is an integer of 0 to 4);
- composition for forming a passivation film according to the sixth aspect in which, in Formula (3), R 1 is a group containing at least a cyano group, and n1 is an integer of 1 to 4;
- composition for forming a passivation film according to the sixth aspect in which, in Formula (4), L 2 is a sulfonyl group or a carbonyl group;
- composition for forming a passivation film according to any one of the first aspect to the ninth aspect, further comprising: a polymer containing a unit structure of Formula (7):
- R 1 , R 2 , and R 3 is a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups;
- L 2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4)
- T 3 is an alkylene group, a sulfonyl group, a carbonyl group, a C 6-30 arylene group optionally having a substituent, or a combination of any
- the composition for forming a passivation film according to any one of the first aspect to the tenth aspect, in which the arylene group is a phenylene group, a naphthylene group, or an anthrylene group;
- each of R 7 and R 8 is a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; each of n7 and n8 is an integer of 0 to 4; and T 4 is an alkylene group, a sulfonyl group, a carbonyl group, a C 6-30 arylene group optionally having a substituent, or a combination of any of these groups);
- composition for forming a passivation film according to any one of the sixth aspect to the eleventh aspect, in which the group having a tertiary carbon atom is a tertiary butyl group;
- composition for forming a passivation film according to any one of the first aspect to the twelfth aspect, in which weight-average molecular weight of the polymer is from 500 to 5,000,000;
- composition for forming a passivation film according to any one of the first aspect to the fourteenth aspect, further comprising: a solvent;
- a passivation film obtained by applying the composition for forming a passivation film as described in any one of the first aspect to the fifteenth aspect to a substrate, and baking the substrate;
- the passivation film according to the sixteenth aspect in which the passivation film is used as a film protecting an IC circuit formed on a wafer;
- the passivation film according to the sixteenth aspect in which the passivation film is used as a film protecting an electrode formed on a rear surface of a wafer.
- the use of the above-described composition including a polymer having a polyether structure, such as a polyether ether ketone, a polyether ether sulfone, and a polyether ether arylene as a composition for forming a passivation film allows an insulating film having good electric insulation, heat-tolerance, solvent-tolerance, and a dry etch back property to be formed.
- a composition for forming a passivation film of the present invention includes a polymer containing a unit structure of Formula (i) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer.
- the composition for forming a passivation film of the present invention includes: a polymer containing a unit structure of Formula (i) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer; and a solvent, and may further include an additional resin, a stabilizer, a colorant, a surfactant and the like as optional components.
- a composition for forming a passivation film of the present invention includes a polymer containing a unit structure of Formula (1) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer.
- the composition for forming a passivation film of above includes: a polymer containing a unit structure of Formula (1) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer; and a solvent, and may further include an additional resin, a stabilizer, a colorant, a surfactant and the like as optional components.
- a hydroxy group or an amino group contained in the polymer is converted to an organic group containing a multiple bond consisting of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, and a polymer having a conversion rate of 100% can be used.
- the conversion rate can be within a range of, for example, 30% to 99%, 60% to 99%, or 70% to 95%.
- the solid content of a composition for forming a passivation film of the present invention is within a range of 0.1% to 80% by mass, and preferably 1% to 60% by mass.
- the solid content is a percentage of a residual after removing a solvent from the composition for forming a passivation film.
- a percentage of a polymer containing a unit structure of Formula (1) in the solid content can be 30% to 100% by mass, and preferably 50% to 100% by mass.
- a polymer used for the present invention is preferably a thermosetting resin.
- the structure of Formula (2-A) is a carbon-carbon triple bond
- the structure of Formula (2-B) is a carbon-carbon double bond.
- these structures exist as the structures of Formulae below, respectively,
- Such carbon-carbon triple bonds are considered to be dimerized or trimerized with heating (for example, at 400° C. or above) to form a sequential unsaturated bond (for example, a diene structure) or an aromatic ring structure, and whereby polymer molecules are cross-linked with each other.
- Such carbon-carbon double bonds are also considered to be dimerized with heating to form a cross-linked structure by cyclization.
- the weight-average molecular weight of the polymer used for the present invention is within a range of 500 to 5,000,000, preferably 1,000 to 1,000,000, and preferably 1,000 to 100,000.
- T 0 is a sulfonyl group, a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group.
- L 1 is an arylene group optionally having a substituent, or is a combination of an arylene group optionally having a substituent and a sulfonyl group or a carbonyl group; and T 1 is a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group.
- Examples of an arylene group having a substituent include an arylene group having a substituent that will be described later.
- a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group means a combination of a substituted or unsubstituted arylene group and a fluoroalkylene group, or a combination of a substituted or unsubstituted arylene group and a cycloalkylene group.
- Examples of an arylene group include a phenylene group, a naphthyl group, and an anthryl group. Of these, a phenylene group and a naphthyl group can preferably be used.
- the fluoroalkylene group examples include C 1-10 fluoroalkylene groups.
- the fluoroalkylene group usable includes a group completely fluorinated (perfluorinated), and an alkylene group partially fluorinated (monofluorinated, difluorinated and the like). Specific examples thereof include a fluoromethylene group, a fluoroethylene group, a fluoro-n-propylene group, a fluoroisopropylene group, a fluoropropane-2,2-diyl group, a fluoro-n-butylene group, a fluoroisobutylene group, a fluoro-s-butylene group, and a fluoro-t-butylene group.
- C 1-4 fluoroalkylene groups such as a perfluoropropane-2,2-diyl group are preferable.
- Examples of a cycloalkylene group include C 3-30 cycloalkylene groups, such as a cyclopropylene group, a cyclobutylene group, a cyclohexylene group, a 1-methyl-cyclopentylene group, a 2-methyl-cyclopentylene group, a 3-methyl-cyclopentylene group, a 1-ethyl-cyclobutylene group, a 2-ethyl-cyclobutylene group, a 3-ethyl-cyclobutylene group, a 1,2-dimethyl-cyclobutylene group, a 1,3-dimethyl-cyclobutylene group, a 2,2-dimethyl-cyclobutylene group, a 2,3-dimethyl-cyclobutylene group, a 2,4-dimethyl-cyclobutylene group, a 3,3-dimethyl-cyclobutylene group, a 1-n-propyl-cyclopropylene group, a 2-n-propy
- the above-explained functional groups can be used alone or in combination of plural types for each of L 1 and T 1 .
- the polymer used for the present invention can be used as a homopolymer having one type of unit structure, or can be used as a copolymer having two or more types of unit structures.
- the present invention can include a polymer containing a unit structure of Formula (1) where L 1 is a group of Formula (3) and/or Formula (4).
- a composition for forming a passivation film of the present invention can comprise a polymer containing a unit structure of Formula (1) where L 1 is a group of Formula (3), a unit structure of Formula (1) where L 1 is a group of Formula (4), or a combination of these unit structures.
- each of R 1 , R 2 , and R 3 is a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups;
- L 2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4.
- Examples of the C 1-10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, a 1-methyl-n-butyl group, a 2-methyl-n-butyl group, a 3-methyl-n-butyl group, a 1,1-dimethyl-n-propyl group, a 1,2-dimethyl-n-propyl group, a 2,2-dimethyl-n-propyl group, a 1-ethyl-n-propyl group, an n-hexyl group, a 1-methyl-n-pentyl group, a 2-methyl-n-pentyl group, a 3-methyl-n-pentyl group, a 4-methyl-n-pentyl group, a 1,1-
- the C 1-4 fluoroalkyl group usable includes a group completely fluorinated (perfluorinated), and an alkyl group partially fluorinated (monofluorinated, difluorinated and the like). Specific examples thereof include a fluoromethyl group, a fluoroethyl group, a fluoro-n-propyl group, a fluoroisopropyl group, a fluoro-n-butyl group, a fluoroisobutyl group, a fluoro-s-butyl group, and a fluoro-t-butyl group.
- acyl group examples include C 2-10 acyl groups, such as a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, a cyclopropylcarbonyl group, an n-butylcarbonyl group, an i-butylcarbonyl group, an s-butylcarbonyl group, a t-butylcarbonyl group, a cyclobutylcarbonyl group, a 1-methyl-cyclopropylcarbonyl group, a 2-methyl-cyclopropylcarbonyl group, an n-pentylcarbonyl group, a 1-methyl-n-butylcarbonyl group, a 2-methyl-n-butylcarbonyl group, a 3-methyl-n-butylcarbonyl group, a 1,1-dimethyl-n-propylcarbonyl group, a 1,2-dimethyl-n-propy
- acyloxy group examples include C 2-10 acyloxy groups, such as a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an i-propylcarbonyloxy group, a cyclopropylcarbonyloxy group, an n-butylcarbonyloxy group, an i-butylcarbonyloxy group, an s-butylcarbonyloxy group, a t-butylcarbonyloxy group, a cyclobutylcarbonyloxy group, a 1-methyl-cyclopropylcarbonyloxy group, a 2-methyl-cyclopropylcarbonyloxy group, an n-pentylcarbonyloxy group, a 1-methyl-n-butylcarbonyloxy group, a 2-methyl-n-butylcarbonyloxy group, a 3-methyl-n-butylcarbonyloxy group, a 1,1-dimethyl-n-propy
- a group having a tertiary carbon atom is a functional group having a tertiary carbon atom.
- the functional group is substituted with a hydrogen atom on a carbon atom to produce a quaternary carbon.
- Examples of an organic group bonded to carbon of the tertiary carbon atom include alkyl groups, such as a methyl group, an ethyl group, and a propyl group; and aryl groups such as a phenyl group.
- alkyl groups such as a methyl group, an ethyl group, and a propyl group
- aryl groups such as a phenyl group.
- a methyl group is preferably used, and a tertiary butyl group having three methyl groups is preferably used.
- Examples of a cycloalkyl group include C 3-30 cycloalkyl groups, such as a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, a 1-methyl-cyclopentyl group, a 2-methyl-cyclopentyl group, a 3-methyl-cyclopentyl group, a 1-ethyl-cyclobutyl group, a 2-ethyl-cyclobutyl group, a 3-ethyl-cyclobutyl group, a 1,2-dimethyl-cyclobutyl group, a 1,3-dimethyl-cyclobutyl group, a 2,2-dimethyl-cyclobutyl group, a 2,3-dimethyl-cyclobutyl group, a 2,4-dimethyl-cyclobutyl group, a 3,3-dimethyl-cyclobutyl group, a 1-n-propyl-cyclopropyl group, a 2-n-propy
- Examples of the substituent described above include a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, and a group having a tertiary carbon atom, a cycloalkyl group. Specific examples of these groups are the same as respective examples described above.
- a structure of Formula (3) where R 1 is a group containing at least a cyano group, and n1 is an integer of 1 to 4, can be used.
- a structure of Formula (4) where L 2 is a sulfonyl group or a carbonyl group, can be used.
- a polymer usable for the present invention may contain a unit structure of Formula (1) where T 1 is a group of Formula (5), a unit structure of Formula (1) where T 1 is a group of Formula (6), or a combination of these unit structures.
- a polymer usable may contain a unit structure of Formula (1) where L 1 is a group of Formula (3), a unit structure of Formula (1) where L 1 is a group of Formula (4), a unit structure of Formula (1) where T 1 is a group of Formula (5), a unit structure of Formula (1) where T 1 is a group of Formula (6), a unit structure of Formula (1) where L 1 is a group of Formula (3) and T 1 is a group of Formula (5), a unit structure of Formula (1) where L 1 is a group of Formula (3) and T 1 is a group of Formula (6), a unit structure of Formula (1) where L 1 is a group of Formula (4) and T 1 is a group of Formula (5), a unit structure of Formula (1) where L 1 is a group of Formula (4) and T 1 is a group of Formula (6), or a combination of any of these unit structures.
- each of R 4 , R 5 , and R 6 is a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; and each of n4, n5, and n6 is an integer of 0 to 4.
- T 2 is a fluoroalkylene group, a cycloalkylene group, or a combination of these groups.
- Examples of a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, an acyl group, an acyloxy group, a group having a tertiary carbon atom, and a cycloalkyl group are the same as respective examples described above.
- Examples of a fluoroalkylene group and a cycloalkylene group are the same as respective examples described above, and these can be used alone, or can be used in combination.
- a copolymer containing a unit structure of Formula (1) and a unit structure of Formula (7) can be used for the present invention.
- L 3 is a group of Formula (3) or Formula (4)
- T 3 is an alkylene group, a sulfonyl group, a carbonyl group, a C 6-30 arylene group optionally having a substituent, or a combination of any of these groups.
- Examples of the arylene group and the alkylene group are the same as respective examples described above.
- a substituted or unsubstituted phenylene group or a naphthylene group can be used as an arylene group.
- the alkylene group include C 1-10 alkylene groups, such as a methylene group, an ethylene group, a propylene group, an isopropylene group, a propane-2,2-diyl group, a butylene group, an isobutylene group, a butylene group, and a butylene group.
- C 1-4 alkylene groups such as a propane-2,2-diyl group are preferable.
- each of R 7 and R 8 is a C 1-10 alkyl group, a C 1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; each of n7 and n8 is an integer of 0 to 4; and T 4 is an alkylene group, a sulfonyl group, a carbonyl group, a C 6-30 arylene group optionally having a substituent, or a combination of any of these groups.
- alkyl group examples include the C 1-4 fluoroalkyl group, the acyl group, the acyloxy group, the group having a tertiary carbon atom, the cycloalkyl group, the alkylene group, and the arylene group are the same as respective examples described above.
- Examples of the unit structure contained in a polymer used for the present invention include the unit structures of Formulae (1-1) to (1-45).
- a hydroxy group can be introduced at the end, or a functional group having a hydroxy group can be introduced in the side chain.
- a monohalogenated alkyne for example, halogen is fluorine, chlorine, bromine, and iodine
- a monohalogenated alkene for example, halogen is fluorine, chlorine, bromine, and iodine
- a carbon-carbon triple bond alkyne
- a carbon-carbon double bond alkene
- halogenated alkyne for example, halogen is fluorine, chlorine, bromine, and iodine
- a dihalogenated alkene for example, halogen is fluorine, chlorine, bromine, and iodine
- a carbon-carbon triple bond alkyne
- a carbon-carbon double bond alkene
- a composition for forming a passivation film of the present invention can be dissolved in an organic solvent to make a coating liquid for spin-coating.
- a coating liquid can be used for spin-coating when the polymer is dissolved in the organic solvent, and the solution has a viscosity within a range from 0.001 Pa ⁇ s to 5,000 Pa ⁇ s.
- the organic solvent is not particularly limited, as long as it can be used in other steps for semiconductors; organic solvents preferably used are ketones, such as cyclohexanone, methyl isoamyl ketone, and 2-heptanone; polyhydric alcohols and derivatives thereof, such as ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, and dipropylene glycol, or monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether, or monophenyl ether of dipropylene glycol monoacetate; cyclic ethers, such as dioxane; and esters, such as methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methoxypropionic acid methyl ester,
- miscible additives such as a surfactant for improving coating performance, an additional resin, a stabilizer, and a colorant, can further be added to a composition for forming a passivation film according to the embodiments of the present invention, as long as these additives do not affect essential properties of the present invention.
- surfactant examples include nonionic surfactants including polyoxyethylene alkylethers, such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether; polyoxyethylene alkylarylethers, such as polyoxyethylene octyl phenol ether and polyoxyethylene nonyl phenol ether; polyoxyethylene-polyoxypropylene block copolymers; sorbitan fatty acid esters, such as sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan tristearate; and polyoxyethylene sorbitan fatty acid esters, such as polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, and polyoxyethylene sorbitan tristearate
- Addition polymerization polymers or condensation polymerization polymers such as polyesters, polystyrenes, polyimides, acrylic polymers, methacrylic polymers, polyvinyl ethers, phenol novolacs, naphthol novolacs, polyethers, polyamides, and polycarbonates can be used as the additional resin (polymer).
- polymers having an aromatic ring structure such as a benzene ring, a naphthalene ring, an anthracene ring, a triazine ring, a quinoline ring, and a quinoxaline ring are preferably used.
- the additional resin (polymer) examples include an addition polymerization polymer having an addition polymerization monomer, such as benzyl acrylate, benzyl methacrylate, phenyl acrylate, naphthyl acrylate, anthryl methacrylate, anthrylmethyl methacrylate, styrene, hydroxy styrene, benzylvinyl ether, and N-phenyl maleimide, as a structural unit thereof; and a condensation polymerization polymer such as phenol novolac and naphthol novolac.
- an addition polymerization polymer having an addition polymerization monomer such as benzyl acrylate, benzyl methacrylate, phenyl acrylate, naphthyl acrylate, anthryl methacrylate, anthrylmethyl methacrylate, styrene, hydroxy styrene, benzylvinyl ether, and N-phenyl maleimide, as
- a polymer not having any aromatic ring structures can also be used as the additional resin (polymer).
- additional resin polymer
- examples of such a polymer include addition polymerization polymers containing only an addition polymerization monomer not having any aromatic ring structures as a structural unit thereof, such as alkyl acrylates, alkyl methacrylates, vinyl ether, alkylvinyl ethers, acrylonitrile, maleimide, N-alkyl maleimides, and maleic acid anhydride.
- an addition polymerization polymer as an additional resin (polymer)
- the polymer may be a homopolymer or a copolymer.
- Addition polymerization monomers are used for manufacturing an addition polymerization polymer.
- the addition polymerization monomer include acrylic acid, methacrylic acid, acrylic acid ester compounds, methacrylic acid ester compounds, acrylamide compounds, methacrylamide compounds, vinyl compounds, styrene compounds, maleimide compounds, maleic acid anhydride, and acrylonitrile.
- acrylic acid ester compounds include methyl acrylate, ethyl acrylate, normal hexyl acrylate, isopropyl acrylate, cyclohexyl acrylate, benzyl acrylate, phenyl acrylate, anthrylmethyl acrylate, 2-hydroxyethyl acrylate, 3-chloro-2-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 2,2,2-trifluoroethyl acrylate, 2,2,2-trichloroethyl acrylate, 2-bromoethyl acrylate, 4-hydroxybutyl acrylate, 2-methoxyethyl acrylate, tetrahydrofurfuryl acrylate, 2-methyl-2-adamantyl acrylate, 5-acryloyloxy-6-hydroxynorbomene-2-carboxylic-6-lactone, 3-acryloxypropyl triethoxysilane, and glycidyl acrylate.
- methacrylic acid ester compounds include methyl methacrylate, ethyl methacrylate, normal hexyl methacrylate, isopropyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, phenyl methacrylate, anthrylmethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2,2,2-trifluoroethyl methacrylate, 2,2,2-trichloroethyl methacrylate, 2-bromoethyl methacrylate, 4-hydroxybutyl methacrylate, 2-methoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 2-methyl-2-adamantyl methacrylate, 5-methacryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone, 3-methacryloxypropyl triethoxysilane, glycidyl
- acrylamide compounds include acrylamide, N-methyl acrylamide, N-ethyl acrylamide, N-benzyl acrylamide, N-phenyl acrylamide, N,N-dimethyl acrylamide, and N-anthryl acrylamide.
- methacrylamide compounds include methacrylamide, N-methyl methacrylamide, N-ethyl methacrylamide, N-benzyl methacrylamide, N-phenyl methacrylamide, N,N-dimethyl methacrylamide, and N-anthryl acrylamide.
- vinyl compounds include vinylalcohol, 2-hydroxyethyl vinyl ether, methyl vinyl ether, ethyl vinyl ether, benzyl vinyl ether, vinyl acetic acid, vinyltrimethoxysilane, 2-chloroethyl vinyl ether, 2-methoxyethyl vinyl ether, vinyl naphthalene, and vinyl anthracene.
- styrene compounds include styrene, hydroxystyrene, chlorostyrene, bromostyrene, methoxystyrene, cyanostyrene, and acetylstyrene.
- maleimide compounds include maleimide, N-methylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzyl maleimide, and N-hydroxyethylmaleimide.
- the weight-average molecular weight of the additional resin is, for example, 1,000 to 1,000,000, or 3,000 to 300,000; and for example, 5,000 to 200,000, or 10,000 to 100,000.
- a content thereof is, for example, 0% to 40% by mass, or 0% to 20% by mass, or 1% to 19% by mass of a solid content.
- the thickness of a passivation film that is prepared by spin-coating a substrate with a composition for forming a passivation film by using a device such as a spin coater may preferably be 0.1 ⁇ m or more and 200 ⁇ m or less.
- a thickness from 1 ⁇ m to 50 ⁇ m is preferable.
- baking may be conducted at a temperature within a range of about 100° C. to about 350° C., about 100° C. to about 300° C., or about 100° C. to about 250° C., for about 0.5 minute to about 180 minutes, about 0.5 minute to about 40 minutes, or about 0.5 minute to about 5 minutes.
- a passivation film thus obtained is also included in the scope of the present invention.
- a passivation film of the present invention can be suitably used as a film protecting an IC circuit formed on a wafer, or a film protecting an electrode formed on the rear surface of a wafer.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-16)) showed that the weight average molecular weight of the compound was 14,700 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 86%.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-1)) showed that the weight average molecular weight of the compound was 19,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-2)) showed that the weight average molecular weight of the compound was 15,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-3)) showed that the weight average molecular weight of the compound was 22,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-4)) showed that the weight average molecular weight of the compound was 26,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-5)) showed that the weight average molecular weight of the compound was 7,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-6)) showed that the weight average molecular weight of the compound was 12,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-7)) showed that the weight average molecular weight of the compound was 11,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-8)) showed that the weight average molecular weight of the compound was 40,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-14)) showed that the weight average molecular weight of the compound was 40,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-36)) showed that the weight average molecular weight of the compound was 13,400 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 88%.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-37)) showed that the weight average molecular weight of the compound was 13,900 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 88%.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-16)) showed that the weight average molecular weight of the compound was 14,700 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 52%.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-17)) showed that the weight average molecular weight of the compound was 12,700 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 50%.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-18)) showed that the weight average molecular weight of the compound was 18,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-40)) showed that the weight average molecular weight of the compound was 27,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-20)) showed that the weight average molecular weight of the compound was 23,000 in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-42)) showed that the weight average molecular weight of the compound was ND in terms of polystyrene.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-43)) showed that the weight average molecular weight of the compound was 16,000 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 79%.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-44)) showed that the weight average molecular weight of the compound was 6,600 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 52%.
- the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic.
- a litmus paper was used to confirm acidity of the solution.
- the obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated.
- the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol.
- the obtained powder was dried in a vacuum dryer for 12 hours.
- a GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-45)) showed that the weight average molecular weight of the compound was 28,000 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 84%.
- the CYCLOTENE 3022-35 (manufactured by the Dow Chemical Company), which is a benzocyclobutene resin solution, was prepared as a composition for forming a passivation film.
- polysulfone (Sigma-Aldrich Japan K.K.) was dissolved in 200 g of 1-methyl-2-pyrrolidone, and then filtered through a polyethylene microfilter having a pore size of 1.0
- Each of passivation films produced with compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was evaluated for solvent-tolerance, heat-tolerance, adhesive force, dry etching, and electrical properties.
- compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film.
- the formed film was immersed in 1-methyl-2-pyrrolidone at 23° C. for 1 minute, and then solvent-tolerance of the film was evaluated with a percentage of a residual film.
- compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film.
- the temperature of the formed film in a TG-DTA (manufactured by Bruker AXS K.K., TG/DTA2010SR) was elevated at 10° C./minute, and the heat-tolerance was evaluated from a temperature at which the amount decreases by 3% by mass.
- the wafer was also placed on a hot plate heated at 260° C., and evaluated for whether the film has tackiness by touching with forceps.
- compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater under the condition of 1,500 rpm, 30 seconds, and cured at 200° C. for 30 minutes to form a passivation film.
- the cross-cut adhesion test JIS K5400 was conducted to the formed film, and adhesiveness was evaluated with the number of squares remained on the wafer.
- compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film. Etching was conducted for 2 minutes, by using a reactive ion etching device (RIE-10NR, manufactured by SAMCO INC.) under the oxygen flux of 50 sccm, the pressure of 12 Pa, and the RF output of 250 W, and the dry etching property of the formed film was evaluated as a reduced amount of a film thickness per 1 minute.
- RIE-10NR reactive ion etching device
- Diluted solutions were prepared by adding solvents to compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3, so that films formed on silicon wafers by using a spin coater have film thicknesses of 1 ⁇ m.
- Each of the prepared diluted solutions was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film.
- a voltage of 2 MV/cm was applied to the passivation film by using a mercury probe (CVmap 92-B, manufactured by Four Dimensions Inc.), and a leak current value and permittivity (converted to relative permittivity) were measured to evaluate electrical properties.
- the passivation films obtained from the present invention showed good values for all of solvent-tolerance, heat-tolerance, adhesiveness, O 2 dry etching properties, and electrical properties.
- a passivation film obtained from a composition for forming a passivation film of the present invention has excellent solvent-tolerance, heat-tolerance, adhesiveness, O 2 dry etching properties, electrical properties and the like.
- a passivation film of the present invention can be used as a film protecting an IC circuit formed on a wafer, a film protecting an electrode formed on the rear surface of a wafer, and the like.
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- General Chemical & Material Sciences (AREA)
- Ceramic Engineering (AREA)
- Formation Of Insulating Films (AREA)
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Abstract
There is provided a composition for forming a passivation film that satisfies electric insulation, heat-tolerance, solvent-tolerance, and a dry etch back property at the same time. A composition for forming a passivation film, including: a polymer containing a unit structure of Formula (i):
T0-O Formula (i)
(where T0 is a sulfonyl group, a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group), wherein the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at an end, in a side chain, or in a main chain of the polymer:
The polymer may contain a unit structure of Formula (1):
L1-O-T1-O Formula (1)
Description
- The present invention relates to an insulating film and particularly to a passivation film protecting an electrode on the rear surface of a wafer formed by the through silicon via (TSV) technology in a step in which lamination bodies such as semiconductor products, for example, IC chips, and optical products are formed.
- In recent years, highly integrated semiconductor devices, smaller mounted areas, and lowering interconnection resistances by reducing interconnection distances have been in high demand due to high-performance and compact electron equipment, such as cell-phones and IC cards. To obtain these, stack structures in which semiconductor elements are stacked in a vertical direction have been developed.
- One example of methods for producing stack structures is a method including steps of: thinning a wafer on which a semiconductor element is formed; providing a through-hole with a technique such as anisotropic dry etching (through silicon via: TSV technique); forming an electrode on the rear surface of the wafer by filling the through-hole with a conductive material such as copper; forming a passivation film on the rear surface having an electrode; and electrically joining the wafer and a chip or the surface of a wafer on which another semiconductor element is formed.
- In the steps above, the insulating film formed on the rear surface of a wafer is required to be electrically insulative to prevent current leakage and migration of a conductive material, to be solvent-tolerant and have a good dry etch back property in a photolithography step that is to open an electrode portion after forming a passivation film, and to be heat-tolerant in an electrode-joining step.
- Examples of well-known passivation films include benzocyclobutene resins, polyimides, and fully aromatic polyethers.
- However, benzocyclobutene resins require a fluorine gas to be used for dry etch back in a photolithography step, and thus electrodes and wafers may be damaged. In addition, cross-linking reaction does not sufficiently proceed at a curing temperature around 200° C., and a good solvent-tolerance cannot be obtained.
- In contrast, as for polyimides, thinned wafers may be damaged because the film-forming temperature is 300° C. or higher, and shrinkage of films upon curing results in remaining stresses.
- Fully aromatic polyethers have no heat cross-linking portion, and thus are not highly tolerant of solvents. In addition, resins may be melted in joining electrodes because the resins have low softening points.
- A substrate for a thick film technique has been disclosed (Patent Document 1). In the substrate, an undercoat film containing 30% by volume to 45% by volume of a polyether ether ketone resin powder and a thermosetting resin is formed on an inorganic insulating substrate that is a glass base material impregnated with a silicone resin.
- Covering products, such as an adhesive for flexible printed-circuit boards, that contain a polymer having a main chain composed of a polyimide, and having a functional group having a carbon-carbon triple bond at an end thereof, have been disclosed (Patent Document 2).
- Covering products, such as an adhesive composition containing a polymer having a main chain containing a functional group having a phenyl group, urea, an amido group and the like, and a carbon-carbon triple bond, have been disclosed (Patent Document 3).
- Covering products, such as an adhesive composition containing a polymer containing polyether ether sulfone having a sulfonic acid group, and containing polyether ether ketone, have been disclosed (Patent Document 4).
- Patent Document 1: Japanese Patent Application Publication No. 2009-070875 (JP 2009-070875 A)
- Patent Document 2: WO 2006-137369
- Patent Document 3: Japanese Patent Application Publication No. 2010-065097 (JP 2010-065097 A)
- Patent Document 4: Japanese Patent Application Publication No. 2005-264008 (JP 2005-264008 A)
- In view of the above-described disadvantages, it is an object of the present invention to provide a composition for forming a passivation film that satisfies electric insulation, heat-tolerance, solvent-tolerance, and a dry etch back property at the same time.
- The present invention provides: as a first aspect, a composition for forming a passivation film, comprising: a polymer containing a unit structure of Formula (i):
-
T0-O Formula (i) - (where T0 is a sulfonyl group, a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group), in which the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at an end, in a side chain, or in a main chain of the polymer:
- as a second aspect, a composition for forming a passivation film, comprising: a polymer containing a unit structure of Formula (1):
-
L1-O-T1-O Formula (1) - (where L1 is an arylene group optionally having a substituent, or is a combination of an arylene group optionally having a substituent and a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and T1 is a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group, or is a combination of an arylene group optionally having a substituent, a fluoroalkylene group, and a cycloalkylene group), in which the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at an end, in a side chain, or in a main chain of the polymer:
- as a third aspect, the composition for forming a passivation film according to the first aspect or the second aspect, in which the arylene group is a phenylene group, a naphthylene group, or an anthrylene group;
- as a fourth aspect, the composition for forming a passivation film according to any one of the first aspect to the third aspect, in which the polymer is a homopolymer having one type of unit structure;
- as a fifth aspect, the composition for forming a passivation film according to any one of the first aspect to the third aspect, in which the polymer is a copolymer having at least two types of unit structures;
- as a sixth aspect, the composition for forming a passivation film according to any one of the second aspect to the fifth aspect, comprising: a polymer containing a unit structure of Formula (1) where L1 is a group of Formula (3) below, a unit structure of Formula (1) where L1 is a group of Formula (4) below, or a combination of these unit structures:
- (where each of R1, R2, and R3 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; L2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4);
- as a seventh aspect, the composition for forming a passivation film according to any one of the second aspect to the sixth aspect, comprising: a polymer containing a unit structure of Formula (1) where T1 is a group of Formula (5) below, a unit structure of Formula (1) where T1 is a group of Formula (6) below, or a combination of these unit structures:
- (where each of R4, R5, and R6 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; T2 is a fluoroalkylene group, a cycloalkylene group, or a combination of these groups; and each of n4, n5, and n6 is an integer of 0 to 4);
- as an eighth aspect, the composition for forming a passivation film according to the sixth aspect, in which, in Formula (3), R1 is a group containing at least a cyano group, and n1 is an integer of 1 to 4;
- as a ninth aspect, the composition for forming a passivation film according to the sixth aspect, in which, in Formula (4), L2 is a sulfonyl group or a carbonyl group;
- as a tenth aspect, the composition for forming a passivation film according to any one of the first aspect to the ninth aspect, further comprising: a polymer containing a unit structure of Formula (7):
-
L3-O-T3-O Formula (7) - (where L3 is Formula (3) or Formula (4):
- (where each of R1, R2, and R3 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; L2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4), T3 is an alkylene group, a sulfonyl group, a carbonyl group, a C6-30 arylene group optionally having a substituent, or a combination of any of these groups);
- as a eleventh aspect, the composition for forming a passivation film according to any one of the first aspect to the tenth aspect, in which the arylene group is a phenylene group, a naphthylene group, or an anthrylene group;
- as a twelfth aspect, the composition for forming a passivation film according to the tenth aspect or the eleventh aspect, in which T3 is a group of Formula (8):
- (where each of R7 and R8 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; each of n7 and n8 is an integer of 0 to 4; and T4 is an alkylene group, a sulfonyl group, a carbonyl group, a C6-30 arylene group optionally having a substituent, or a combination of any of these groups);
- as a thirteenth aspect, the composition for forming a passivation film according to any one of the sixth aspect to the eleventh aspect, in which the group having a tertiary carbon atom is a tertiary butyl group;
- as a fourteenth aspect, the composition for forming a passivation film according to any one of the first aspect to the twelfth aspect, in which weight-average molecular weight of the polymer is from 500 to 5,000,000;
- as a fifteenth aspect, the composition for forming a passivation film according to any one of the first aspect to the fourteenth aspect, further comprising: a solvent;
- as a sixteenth aspect, a passivation film obtained by applying the composition for forming a passivation film as described in any one of the first aspect to the fifteenth aspect to a substrate, and baking the substrate;
- as a seventeenth aspect, the passivation film according to the sixteenth aspect, in which the passivation film is used as a film protecting an IC circuit formed on a wafer; and
- as an eighteenth aspect, the passivation film according to the sixteenth aspect, in which the passivation film is used as a film protecting an electrode formed on a rear surface of a wafer.
- According to the present invention, the use of the above-described composition including a polymer having a polyether structure, such as a polyether ether ketone, a polyether ether sulfone, and a polyether ether arylene as a composition for forming a passivation film, allows an insulating film having good electric insulation, heat-tolerance, solvent-tolerance, and a dry etch back property to be formed.
- A composition for forming a passivation film of the present invention includes a polymer containing a unit structure of Formula (i) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer.
- The composition for forming a passivation film of the present invention includes: a polymer containing a unit structure of Formula (i) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer; and a solvent, and may further include an additional resin, a stabilizer, a colorant, a surfactant and the like as optional components.
- A composition for forming a passivation film of the present invention includes a polymer containing a unit structure of Formula (1) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer.
- The composition for forming a passivation film of above includes: a polymer containing a unit structure of Formula (1) where the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at the end, in the side chain, or in the main chain of the polymer; and a solvent, and may further include an additional resin, a stabilizer, a colorant, a surfactant and the like as optional components.
- As described later, in a polymer used for the present invention, a hydroxy group or an amino group contained in the polymer (at the end, or in the side chain) is converted to an organic group containing a multiple bond consisting of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, and a polymer having a conversion rate of 100% can be used. However, considering an electrical property, solubility to a solvent, adhesiveness and the like, the conversion rate can be within a range of, for example, 30% to 99%, 60% to 99%, or 70% to 95%.
- The solid content of a composition for forming a passivation film of the present invention is within a range of 0.1% to 80% by mass, and preferably 1% to 60% by mass. The solid content is a percentage of a residual after removing a solvent from the composition for forming a passivation film. A percentage of a polymer containing a unit structure of Formula (1) in the solid content can be 30% to 100% by mass, and preferably 50% to 100% by mass.
- A polymer used for the present invention is preferably a thermosetting resin.
- The structure of Formula (2-A) is a carbon-carbon triple bond, and the structure of Formula (2-B) is a carbon-carbon double bond. At the end, or in the side chain of a polymer, these structures exist as the structures of Formulae below, respectively,
-
—C≡CH—CH═CH2 - and in the main chain of a polymer, these structures exist as a structure of Formula (2-A) and a structure of Formula (2-B), respectively.
- Such carbon-carbon triple bonds are considered to be dimerized or trimerized with heating (for example, at 400° C. or above) to form a sequential unsaturated bond (for example, a diene structure) or an aromatic ring structure, and whereby polymer molecules are cross-linked with each other.
- Such carbon-carbon double bonds are also considered to be dimerized with heating to form a cross-linked structure by cyclization.
- The weight-average molecular weight of the polymer used for the present invention is within a range of 500 to 5,000,000, preferably 1,000 to 1,000,000, and preferably 1,000 to 100,000.
- In Formula (i), T0 is a sulfonyl group, a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group.
- In Formula (1), L1 is an arylene group optionally having a substituent, or is a combination of an arylene group optionally having a substituent and a sulfonyl group or a carbonyl group; and T1 is a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group.
- Examples of an arylene group having a substituent include an arylene group having a substituent that will be described later.
- A combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group means a combination of a substituted or unsubstituted arylene group and a fluoroalkylene group, or a combination of a substituted or unsubstituted arylene group and a cycloalkylene group.
- Examples of an arylene group include a phenylene group, a naphthyl group, and an anthryl group. Of these, a phenylene group and a naphthyl group can preferably be used.
- Examples of the fluoroalkylene group include C1-10 fluoroalkylene groups. The fluoroalkylene group usable includes a group completely fluorinated (perfluorinated), and an alkylene group partially fluorinated (monofluorinated, difluorinated and the like). Specific examples thereof include a fluoromethylene group, a fluoroethylene group, a fluoro-n-propylene group, a fluoroisopropylene group, a fluoropropane-2,2-diyl group, a fluoro-n-butylene group, a fluoroisobutylene group, a fluoro-s-butylene group, and a fluoro-t-butylene group. Among them, C1-4 fluoroalkylene groups such as a perfluoropropane-2,2-diyl group are preferable.
- Examples of a cycloalkylene group include C3-30 cycloalkylene groups, such as a cyclopropylene group, a cyclobutylene group, a cyclohexylene group, a 1-methyl-cyclopentylene group, a 2-methyl-cyclopentylene group, a 3-methyl-cyclopentylene group, a 1-ethyl-cyclobutylene group, a 2-ethyl-cyclobutylene group, a 3-ethyl-cyclobutylene group, a 1,2-dimethyl-cyclobutylene group, a 1,3-dimethyl-cyclobutylene group, a 2,2-dimethyl-cyclobutylene group, a 2,3-dimethyl-cyclobutylene group, a 2,4-dimethyl-cyclobutylene group, a 3,3-dimethyl-cyclobutylene group, a 1-n-propyl-cyclopropylene group, a 2-n-propyl-cyclopropylene group, a 1-i-propyl-cyclopropylene group, a 2-i-propyl-cyclopropylene group, a 1,2,2-trimethyl-cyclopropylene group, a 1,2,3-trimethyl-cyclopropylene group, a 2,2,3-trimethyl-cyclopropylene group, a 1-ethyl-2-methyl-cyclopropylene group, a 2-ethyl-1-methyl-cyclopropylene group, a 2-ethyl-2-methyl-cyclopropylene group, and a 2-ethyl-3-methyl-cyclopropylene group. A divalent organic group derived from adamantan or norbornene can also be used.
- In the polymer containing a unit structure of Formula (1), which is used for the present invention, the above-explained functional groups can be used alone or in combination of plural types for each of L1 and T1.
- The polymer used for the present invention can be used as a homopolymer having one type of unit structure, or can be used as a copolymer having two or more types of unit structures.
- The present invention can include a polymer containing a unit structure of Formula (1) where L1 is a group of Formula (3) and/or Formula (4).
- Specifically, a composition for forming a passivation film of the present invention can comprise a polymer containing a unit structure of Formula (1) where L1 is a group of Formula (3), a unit structure of Formula (1) where L1 is a group of Formula (4), or a combination of these unit structures.
- In Formulae (3) and (4), each of R1, R2, and R3 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; L2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4.
- Examples of the C1-10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, a 1-methyl-n-butyl group, a 2-methyl-n-butyl group, a 3-methyl-n-butyl group, a 1,1-dimethyl-n-propyl group, a 1,2-dimethyl-n-propyl group, a 2,2-dimethyl-n-propyl group, a 1-ethyl-n-propyl group, an n-hexyl group, a 1-methyl-n-pentyl group, a 2-methyl-n-pentyl group, a 3-methyl-n-pentyl group, a 4-methyl-n-pentyl group, a 1,1-dimethyl-n-butyl group, a 1,2-dimethyl-n-butyl group, a 1,3-dimethyl-n-butyl group, a 2,2-dimethyl-n-butyl group, a 2,3-dimethyl-n-butyl group, a 3,3-dimethyl-n-butyl group, a 1-ethyl-n-butyl group, a 2-ethyl-n-butyl group, a 1,1,2-trimethyl-n-propyl group, a 1,2,2-trimethyl-n-propyl group, a 1-ethyl-1-methyl-n-propyl group, and a 1-ethyl-2-methyl-n-propyl group.
- The C1-4 fluoroalkyl group usable includes a group completely fluorinated (perfluorinated), and an alkyl group partially fluorinated (monofluorinated, difluorinated and the like). Specific examples thereof include a fluoromethyl group, a fluoroethyl group, a fluoro-n-propyl group, a fluoroisopropyl group, a fluoro-n-butyl group, a fluoroisobutyl group, a fluoro-s-butyl group, and a fluoro-t-butyl group.
- Examples of the acyl group include C2-10 acyl groups, such as a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, a cyclopropylcarbonyl group, an n-butylcarbonyl group, an i-butylcarbonyl group, an s-butylcarbonyl group, a t-butylcarbonyl group, a cyclobutylcarbonyl group, a 1-methyl-cyclopropylcarbonyl group, a 2-methyl-cyclopropylcarbonyl group, an n-pentylcarbonyl group, a 1-methyl-n-butylcarbonyl group, a 2-methyl-n-butylcarbonyl group, a 3-methyl-n-butylcarbonyl group, a 1,1-dimethyl-n-propylcarbonyl group, a 1,2-dimethyl-n-propylcarbonyl group, a 2,2-dimethyl-n-propylcarbonyl group, a 1-ethyl-n-propylcarbonyl group, a cyclopentylcarbonyl group, a 1-methyl-cyclobutylcarbonyl group, a 2-methyl-cyclobutylcarbonyl group, a 3-methyl-cyclobutylcarbonyl group, a 1,2-dimethyl-cyclopropylcarbonyl group, a 2,3-dimethyl-cyclopropylcarbonyl group, a 1-ethyl-cyclopropylcarbonyl group, a 2-ethyl-cyclopropylcarbonyl group, an n-hexylcarbonyl group, a 1-methyl-n-pentylcarbonyl group, a 2-methyl-n-pentylcarbonyl group, a 3-methyl-n-pentylcarbonyl group, a 4-methyl-n-pentylcarbonyl group, a 1,1-dimethyl-n-butylcarbonyl group, a 1,2-dimethyl-n-butylcarbonyl group, a 1,3-dimethyl-n-butylcarbonyl group, a 2,2-dimethyl-n-butylcarbonyl group, a 2,3-dimethyl-n-butylcarbonyl group, a 3,3-dimethyl-n-butylcarbonyl group, a 1-ethyl-n-butylcarbonyl group, a 2-ethyl-n-butylcarbonyl group, and a 1,1,2-trimethyl-n-propylcarbonyl group.
- Examples of the acyloxy group include C2-10 acyloxy groups, such as a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an i-propylcarbonyloxy group, a cyclopropylcarbonyloxy group, an n-butylcarbonyloxy group, an i-butylcarbonyloxy group, an s-butylcarbonyloxy group, a t-butylcarbonyloxy group, a cyclobutylcarbonyloxy group, a 1-methyl-cyclopropylcarbonyloxy group, a 2-methyl-cyclopropylcarbonyloxy group, an n-pentylcarbonyloxy group, a 1-methyl-n-butylcarbonyloxy group, a 2-methyl-n-butylcarbonyloxy group, a 3-methyl-n-butylcarbonyloxy group, a 1,1-dimethyl-n-propylcarbonyloxy group, a 1,2-dimethyl-n-propylcarbonyloxy group, a 2,2-dimethyl-n-propylcarbonyloxy group, a 1-ethyl-n-propylcarbonyloxy group, a cyclopentylcarbonyloxy group, a 1-methyl-cyclobutylcarbonyloxy group, a 2-methyl-cyclobutylcarbonyloxy group, a 3-methyl-cyclobutylcarbonyloxy group, a 1,2-dimethyl-cyclopropylcarbonyloxy group, a 2,3-dimethyl-cyclopropylcarbonyloxy group, a 1-ethyl-cyclopropylcarbonyloxy group, a 2-ethyl-cyclopropylcarbonyloxy group, an n-hexylcarbonyloxy group, a 1-methyl-n-pentylcarbonyloxy group, a 2-methyl-n-pentylcarbonyloxy group, a 3-methyl-n-pentylcarbonyloxy group, a 4-methyl-n-pentylcarbonyloxy group, a 1,1-dimethyl-n-butylcarbonyloxy group, a 1,2-dimethyl-n-butylcarbonyloxy group, a 1,3-dimethyl-n-butylcarbonyloxy group, a 2,2-dimethyl-n-butylcarbonyloxy group, a 2,3-dimethyl-n-butylcarbonyloxy group, a 3,3-dimethyl-n-butylcarbonyloxy group, a 1-ethyl-n-butylcarbonyloxy group, a 2-ethyl-n-butylcarbonyloxy group, and a 1,1,2-trimethyl-n-propylcarbonyloxy group.
- In the present invention, a group having a tertiary carbon atom is a functional group having a tertiary carbon atom. The functional group is substituted with a hydrogen atom on a carbon atom to produce a quaternary carbon. Examples of an organic group bonded to carbon of the tertiary carbon atom include alkyl groups, such as a methyl group, an ethyl group, and a propyl group; and aryl groups such as a phenyl group. Among them, a methyl group is preferably used, and a tertiary butyl group having three methyl groups is preferably used.
- Examples of a cycloalkyl group include C3-30 cycloalkyl groups, such as a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, a 1-methyl-cyclopentyl group, a 2-methyl-cyclopentyl group, a 3-methyl-cyclopentyl group, a 1-ethyl-cyclobutyl group, a 2-ethyl-cyclobutyl group, a 3-ethyl-cyclobutyl group, a 1,2-dimethyl-cyclobutyl group, a 1,3-dimethyl-cyclobutyl group, a 2,2-dimethyl-cyclobutyl group, a 2,3-dimethyl-cyclobutyl group, a 2,4-dimethyl-cyclobutyl group, a 3,3-dimethyl-cyclobutyl group, a 1-n-propyl-cyclopropyl group, a 2-n-propyl-cyclopropyl group, a 1-i-propyl-cyclopropyl group, a 2-i-propyl-cyclopropyl group, a 1,2,2-trimethyl-cyclopropyl group, a 1,2,3-trimethyl-cyclopropyl group, a 2,2,3-trimethyl-cyclopropyl group, a 1-ethyl-2-methyl-cyclopropyl group, a 2-ethyl-1-methyl-cyclopropyl group, a 2-ethyl-2-methyl-cyclopropyl group, and a 2-ethyl-3-methyl-cyclopropyl group. A monovalent organic group derived from adamantan or norbornene can also be used.
- Examples of the substituent described above include a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, and a group having a tertiary carbon atom, a cycloalkyl group. Specific examples of these groups are the same as respective examples described above.
- A structure of Formula (3) where R1 is a group containing at least a cyano group, and n1 is an integer of 1 to 4, can be used.
- A structure of Formula (4) where L2 is a sulfonyl group or a carbonyl group, can be used.
- With or without the choice for L1 described above, a polymer usable for the present invention may contain a unit structure of Formula (1) where T1 is a group of Formula (5), a unit structure of Formula (1) where T1 is a group of Formula (6), or a combination of these unit structures.
- Specifically, a polymer usable may contain a unit structure of Formula (1) where L1 is a group of Formula (3), a unit structure of Formula (1) where L1 is a group of Formula (4), a unit structure of Formula (1) where T1 is a group of Formula (5), a unit structure of Formula (1) where T1 is a group of Formula (6), a unit structure of Formula (1) where L1 is a group of Formula (3) and T1 is a group of Formula (5), a unit structure of Formula (1) where L1 is a group of Formula (3) and T1 is a group of Formula (6), a unit structure of Formula (1) where L1 is a group of Formula (4) and T1 is a group of Formula (5), a unit structure of Formula (1) where L1 is a group of Formula (4) and T1 is a group of Formula (6), or a combination of any of these unit structures.
- In Formulae (5) and (6), each of R4, R5, and R6 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; and each of n4, n5, and n6 is an integer of 0 to 4. T2 is a fluoroalkylene group, a cycloalkylene group, or a combination of these groups.
- Examples of a C1-10 alkyl group, a C1-4 fluoroalkyl group, an acyl group, an acyloxy group, a group having a tertiary carbon atom, and a cycloalkyl group are the same as respective examples described above.
- Examples of a fluoroalkylene group and a cycloalkylene group are the same as respective examples described above, and these can be used alone, or can be used in combination.
- A copolymer containing a unit structure of Formula (1) and a unit structure of Formula (7) can be used for the present invention.
- In Formula (7), L3 is a group of Formula (3) or Formula (4), and T3 is an alkylene group, a sulfonyl group, a carbonyl group, a C6-30 arylene group optionally having a substituent, or a combination of any of these groups. Examples of the arylene group and the alkylene group are the same as respective examples described above.
- In Formula (7), a substituted or unsubstituted phenylene group or a naphthylene group can be used as an arylene group. In Formula (7), examples of the alkylene group include C1-10 alkylene groups, such as a methylene group, an ethylene group, a propylene group, an isopropylene group, a propane-2,2-diyl group, a butylene group, an isobutylene group, a butylene group, and a butylene group. Among them, C1-4 alkylene groups such as a propane-2,2-diyl group are preferable.
- In Formula (7), a group of Formula (8) can be used as T3. In Formula (8), each of R7 and R8 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; each of n7 and n8 is an integer of 0 to 4; and T4 is an alkylene group, a sulfonyl group, a carbonyl group, a C6-30 arylene group optionally having a substituent, or a combination of any of these groups. Examples of the alkyl group, the C1-4 fluoroalkyl group, the acyl group, the acyloxy group, the group having a tertiary carbon atom, the cycloalkyl group, the alkylene group, and the arylene group are the same as respective examples described above.
- Examples of the unit structure contained in a polymer used for the present invention include the unit structures of Formulae (1-1) to (1-45).
- In a step for synthesizing a polymer containing a unit structure of Formula (i) or a unit structure of Formula (1), a hydroxy group can be introduced at the end, or a functional group having a hydroxy group can be introduced in the side chain.
- When the hydroxy group is reacted with a monohalogenated alkyne (for example, halogen is fluorine, chlorine, bromine, and iodine) or a monohalogenated alkene (for example, halogen is fluorine, chlorine, bromine, and iodine), a carbon-carbon triple bond (alkyne) or a carbon-carbon double bond (alkene) is formed at an end or in a side chain by a dehydrohalogenation reaction.
- When a polymer having a hydroxy group at the end or in the side chain thereof is reacted with a dihalogenated alkyne (for example, halogen is fluorine, chlorine, bromine, and iodine) or a dihalogenated alkene (for example, halogen is fluorine, chlorine, bromine, and iodine), a carbon-carbon triple bond (alkyne) or a carbon-carbon double bond (alkene) is formed in the main chain of the molecule by a dehydrohalogenation reaction.
- Further, when an amino group is contained in a polymer (at an end or in a side chain), the above-mentioned multiple bonds are formed also by similar reactions.
- A composition for forming a passivation film of the present invention can be dissolved in an organic solvent to make a coating liquid for spin-coating. Such a coating liquid can be used for spin-coating when the polymer is dissolved in the organic solvent, and the solution has a viscosity within a range from 0.001 Pa·s to 5,000 Pa·s.
- The organic solvent is not particularly limited, as long as it can be used in other steps for semiconductors; organic solvents preferably used are ketones, such as cyclohexanone, methyl isoamyl ketone, and 2-heptanone; polyhydric alcohols and derivatives thereof, such as ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, and dipropylene glycol, or monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether, or monophenyl ether of dipropylene glycol monoacetate; cyclic ethers, such as dioxane; and esters, such as methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methoxypropionic acid methyl ester, and ethoxypropionic acid ethyl ester. These can be used alone, or two or more of them can be used in combination.
- Conventionally used miscible additives, such as a surfactant for improving coating performance, an additional resin, a stabilizer, and a colorant, can further be added to a composition for forming a passivation film according to the embodiments of the present invention, as long as these additives do not affect essential properties of the present invention.
- Examples of the surfactant include nonionic surfactants including polyoxyethylene alkylethers, such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether; polyoxyethylene alkylarylethers, such as polyoxyethylene octyl phenol ether and polyoxyethylene nonyl phenol ether; polyoxyethylene-polyoxypropylene block copolymers; sorbitan fatty acid esters, such as sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan tristearate; and polyoxyethylene sorbitan fatty acid esters, such as polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, and polyoxyethylene sorbitan tristearate; fluorine surfactants including Eftop (registered trademark) EF301, EF303, and EF352 (manufactured by JEMCO Co., Ltd.), MEGAFAC (registered trademark) F171, F173, and R30 (manufactured by DIC Corporation), Fluorad FC430 and FC431 (manufactured by Sumitomo 3M Limited), and AsahiGuard (registered trademark) AG710, SURFLON (registered trademark) S-382, SC101, SC102, SC103, SC104, SC105, and SC106 (manufactured by Asahi Glass Co., Ltd.); and organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.). These surfactants can be added alone, or two or more surfactants can be added in combination. The mixing amount of the surfactant is, for example, 0.01% to 10% by mass of the whole solid content.
- Addition polymerization polymers or condensation polymerization polymers, such as polyesters, polystyrenes, polyimides, acrylic polymers, methacrylic polymers, polyvinyl ethers, phenol novolacs, naphthol novolacs, polyethers, polyamides, and polycarbonates can be used as the additional resin (polymer). Among them, polymers having an aromatic ring structure such as a benzene ring, a naphthalene ring, an anthracene ring, a triazine ring, a quinoline ring, and a quinoxaline ring are preferably used.
- Examples of the additional resin (polymer) include an addition polymerization polymer having an addition polymerization monomer, such as benzyl acrylate, benzyl methacrylate, phenyl acrylate, naphthyl acrylate, anthryl methacrylate, anthrylmethyl methacrylate, styrene, hydroxy styrene, benzylvinyl ether, and N-phenyl maleimide, as a structural unit thereof; and a condensation polymerization polymer such as phenol novolac and naphthol novolac.
- A polymer not having any aromatic ring structures can also be used as the additional resin (polymer). Examples of such a polymer include addition polymerization polymers containing only an addition polymerization monomer not having any aromatic ring structures as a structural unit thereof, such as alkyl acrylates, alkyl methacrylates, vinyl ether, alkylvinyl ethers, acrylonitrile, maleimide, N-alkyl maleimides, and maleic acid anhydride.
- In the use of an addition polymerization polymer as an additional resin (polymer), the polymer may be a homopolymer or a copolymer. Addition polymerization monomers are used for manufacturing an addition polymerization polymer. Examples of the addition polymerization monomer include acrylic acid, methacrylic acid, acrylic acid ester compounds, methacrylic acid ester compounds, acrylamide compounds, methacrylamide compounds, vinyl compounds, styrene compounds, maleimide compounds, maleic acid anhydride, and acrylonitrile.
- Examples of acrylic acid ester compounds include methyl acrylate, ethyl acrylate, normal hexyl acrylate, isopropyl acrylate, cyclohexyl acrylate, benzyl acrylate, phenyl acrylate, anthrylmethyl acrylate, 2-hydroxyethyl acrylate, 3-chloro-2-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 2,2,2-trifluoroethyl acrylate, 2,2,2-trichloroethyl acrylate, 2-bromoethyl acrylate, 4-hydroxybutyl acrylate, 2-methoxyethyl acrylate, tetrahydrofurfuryl acrylate, 2-methyl-2-adamantyl acrylate, 5-acryloyloxy-6-hydroxynorbomene-2-carboxylic-6-lactone, 3-acryloxypropyl triethoxysilane, and glycidyl acrylate.
- Examples of methacrylic acid ester compounds include methyl methacrylate, ethyl methacrylate, normal hexyl methacrylate, isopropyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, phenyl methacrylate, anthrylmethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2,2,2-trifluoroethyl methacrylate, 2,2,2-trichloroethyl methacrylate, 2-bromoethyl methacrylate, 4-hydroxybutyl methacrylate, 2-methoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 2-methyl-2-adamantyl methacrylate, 5-methacryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone, 3-methacryloxypropyl triethoxysilane, glycidyl methacrylate, 2-phenylethyl methacrylate, hydroxyphenyl methacrylate, and bromophenyl methacrylate.
- Examples of acrylamide compounds include acrylamide, N-methyl acrylamide, N-ethyl acrylamide, N-benzyl acrylamide, N-phenyl acrylamide, N,N-dimethyl acrylamide, and N-anthryl acrylamide.
- Examples of methacrylamide compounds include methacrylamide, N-methyl methacrylamide, N-ethyl methacrylamide, N-benzyl methacrylamide, N-phenyl methacrylamide, N,N-dimethyl methacrylamide, and N-anthryl acrylamide.
- Examples of vinyl compounds include vinylalcohol, 2-hydroxyethyl vinyl ether, methyl vinyl ether, ethyl vinyl ether, benzyl vinyl ether, vinyl acetic acid, vinyltrimethoxysilane, 2-chloroethyl vinyl ether, 2-methoxyethyl vinyl ether, vinyl naphthalene, and vinyl anthracene.
- Examples of styrene compounds include styrene, hydroxystyrene, chlorostyrene, bromostyrene, methoxystyrene, cyanostyrene, and acetylstyrene.
- Examples of maleimide compounds include maleimide, N-methylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzyl maleimide, and N-hydroxyethylmaleimide.
- When an additional resin (polymer) is used in a composition for forming a passivation film of the present invention, the weight-average molecular weight of the additional resin is, for example, 1,000 to 1,000,000, or 3,000 to 300,000; and for example, 5,000 to 200,000, or 10,000 to 100,000.
- When an additional resin (polymer) is contained in a composition for forming a passivation film of the present invention, a content thereof is, for example, 0% to 40% by mass, or 0% to 20% by mass, or 1% to 19% by mass of a solid content.
- In the present invention, the thickness of a passivation film that is prepared by spin-coating a substrate with a composition for forming a passivation film by using a device such as a spin coater, may preferably be 0.1 μm or more and 200 μm or less. When the thickness is excessively small, concavity and convexity of the surface cannot be followed, and thus a void may be formed in the film. In contrast, when the thickness is excessively large, an adhesive layer may be cracked. Accordingly, a thickness from 1 μm to 50 μm is preferable.
- After the substrate is coated, baking may be conducted at a temperature within a range of about 100° C. to about 350° C., about 100° C. to about 300° C., or about 100° C. to about 250° C., for about 0.5 minute to about 180 minutes, about 0.5 minute to about 40 minutes, or about 0.5 minute to about 5 minutes.
- A passivation film thus obtained is also included in the scope of the present invention.
- A passivation film of the present invention can be suitably used as a film protecting an IC circuit formed on a wafer, or a film protecting an electrode formed on the rear surface of a wafer.
- Hereinafter, the present invention will be explained more specifically according to the examples and the comparative examples; however, the present invention is not limited thereto.
- GPC analyses of macromolecular compounds obtained in the synthesis examples described below were conducted with the following device under the following measuring conditions.
- Device: All-in-one high-speed GPC system, HLC-8220GPC, manufactured by Tosoh Corporation
- Column: KF-G, KF804L
- Column temperature: 40° C.
- Solvent: THF
- Flux: 1.0 mL/minute
- Standard sample: polystyrene
- Detector: RI
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 9.27 g of 4,4′-difluorobenzophenone, 9.16 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and 8.66 g of 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene were dissolved in 81.27 g of l-methyl-2-pyrrolidinone. 20.73 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 50.56 g of propargyl bromide dissolved in 39.73 g of 1-methyl-2-pyrrolidinone, and 20.73 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-16)) showed that the weight average molecular weight of the compound was 14,700 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 86%.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 54.56 g of 4,4′-dichlorodiphenylsulfone and 67.25 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane were dissolved in 753.46 g of 1-methyl-2-pyrrolidone. 28.88 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 190° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-1)) showed that the weight average molecular weight of the compound was 19,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 40.37 g of 4,4′-difluorobenzophenone and 69.11 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane were dissolved in 558.56 g of 1-methyl-2-pyrrolidone. 76.71 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 190° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-2)) showed that the weight average molecular weight of the compound was 15,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 25.83 g of 4,4′-difluorobenzophenone, 50.43 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, and 2.75 g of 2,2′-bis(4-hydroxy-3,5-dihydroxymethylphenyl)propane were dissolved in 504.22 g of 1-methyl-2-pyrrolidone. 21.82 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-3)) showed that the weight average molecular weight of the compound was 22,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 43.07 g of 4,4′-dichlorodiphenylsulfone, 50.43 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, and 2.75 g of 2,2′-bis(4-hydroxy-3,5-dihydroxymethylphenyl)propane were dissolved in 590.40 g of 1-methyl-2-pyrrolidone. 21.82 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-4)) showed that the weight average molecular weight of the compound was 26,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 10.43 g of 2,4-fluorobenzonitrile and 26.54 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane were dissolved in 204.22 g of 1-methyl-2-pyrrolidone. 31.10 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 190° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-5)) showed that the weight average molecular weight of the compound was 7,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 10.76 g of 2,5-fluorobenzonitrile and 26.54 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane were dissolved in 204.22 g of 1-methyl-2-pyrrolidone. 31.10 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 190° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-6)) showed that the weight average molecular weight of the compound was 12,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 10.76 g of 2,6-fluorobenzonitrile and 26.54 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane were dissolved in 204.22 g of 1-methyl-2-pyrrolidone. 31.10 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 190° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-7)) showed that the weight average molecular weight of the compound was 11,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 25.84 g of 4,4′-dichlorodiphenylsulfone and 26.54 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane were dissolved in 204.22 g of 1-methyl-2-pyrrolidone. 31.10 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 190° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 12.44 g of potassium carbonate and 22.54 g of propargyl bromide were added, and reacted at 80° C. for 20 hours.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-8)) showed that the weight average molecular weight of the compound was 40,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 10.21 g of 2,4′-dichlorobenzotrifluoride, 9.16 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and 8.41 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane were dissolved in 204.22 g of 1-methyl-2-pyrrolidinone. 20.73 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 190° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 14.14 g of propargyl bromide was added, and reacted at 80° C. for 20 hours.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-14)) showed that the weight average molecular weight of the compound was 40,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 10.81 g of bis(4-fluorophenyl)sulfone, 9.16 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and 6.71 g of 1,1-bis(4-hydroxyphenyl)cyclohexane were dissolved in 80.01 g of 1-methyl-2-pyrrolidinone. 20.73 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 66.54 g of allyl bromide dissolved in 43.31 g of 1-methyl-2-pyrrolidinone, and 20.73 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-36)) showed that the weight average molecular weight of the compound was 13,400 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 88%.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 37.09 g of 4,4′-difluorobenzophenone, 36.63 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and 34.65 g of 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene were dissolved in 325.10 g of 1-methyl-2-pyrrolidinone. 82.93 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 193.57 g of allyl bromide dissolved in 156.76 g of 1-methyl-2-pyrrolidinone, and 138.21 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-37)) showed that the weight average molecular weight of the compound was 13,900 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 88%.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 9.27 g of 4,4′-difluorobenzophenone, 9.16 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and 8.66 g of 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene were dissolved in 81.27 g of 1-methyl-2-pyrrolidinone. 20.73 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 12.64 g of propargyl bromide dissolved in 39.73 g of 1-methyl-2-pyrrolidinone, and 20.73 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-16)) showed that the weight average molecular weight of the compound was 14,700 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 52%.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 6.61 g of 2,4-difluorobenzonitrile, 9.16 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and 8.66 g of 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene were dissolved in 73.28 g of 1-methyl-2-pyrrolidinone. 20.73 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 14.13 g of propargyl bromide dissolved in 27.96 g of 1-methyl-2-pyrrolidinone was added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-17)) showed that the weight average molecular weight of the compound was 12,700 in terms of polystyrene, and a reaction rate of a phenol group and an amino group existed at the end was 50%.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 20.86 g of 2,6-difluorobenzonitrile, 54.91 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, and 1.16 g of 2,2′-bis(4-hydroxy-3,5-dihydroxymethylphenyl)propane were dissolved in 489.50 g of 1-methyl-2-pyrrolidone. 20.93 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.69 g of propargyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-18)) showed that the weight average molecular weight of the compound was 18,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 29.05 g of 4,4′-difluorobenzophenone, 50.43 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, and 1.06 g of 2,2′-bis(4-hydroxy-3,5-dihydroxymethylphenyl)propane were dissolved in 519.13 g of 1-methyl-2-pyrrolidone. 21.82 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 2.16 g of potassium carbonate and 1.97 g of allyl bromide were added and reacted for 20 hours under reflux. The obtained reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the obtained solution until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-40)) showed that the weight average molecular weight of the compound was 27,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 20.44 g of 2,6-difluorobenzonitrile, 50.44 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, and 1.12 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane were dissolved in 528.50 g of 1-methyl-2-pyrrolidone. 63.43 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours.
- After the reaction was completed, the system was cooled until the temperature became 80° C., and then 17.84 g of propargyl bromide dissolved in 53.53 g of 1-methyl-2-pyrrolidinone, 6.02 g of potassium iodide, and 22.80 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-20)) showed that the weight average molecular weight of the compound was 23,000 in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 20.67 g of 4,4′-difluorobenzophenone, 33.62 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, and 1.92 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane were dissolved in 361.12 g of 1-methyl-2-pyrrolidone. 20.67 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours.
- The reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 1N-hydrochloric acid and 1-methyl-2-pyrrolidone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- 10 g of the obtained powder was dissolved in 100 g of tetrahydrofuran, and then 0.45 g of triethylamine was added. The mixture was cooled to a temperature of 0° C., and 0.36 g of acrylic acid chloride dissolved in 10 g of tetrahydrofuran was dropped thereto over 10 minutes. After that, the mixture was left to let the temperature increase, and reacted for 20 hours. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-42)) showed that the weight average molecular weight of the compound was ND in terms of polystyrene.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 74.19 g of 4,4′-difluorobenzophenone, 73.25 g of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and 50.05 g of 4,4′-dihydroxydiphenylsulfone were dissolved in 592.48 g of 1-methyl-2-pyrrolidinone. 165.85 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 104.68 g of propargyl bromide dissolved in 223.67 g of 1-methyl-2-pyrrolidinone, and 165.85 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-43)) showed that the weight average molecular weight of the compound was 16,000 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 79%.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 18.55 g of 4,4′-difluorobenzophenone, 14.02 g of 3,3′-diamino-4,4′-dihydroxydiphenylsulfone, and 17.32 g of 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene were dissolved in 149.67 g of 1-methyl-2-pyrrolidinone. 41.46 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 26.17 g of propargyl bromide dissolved in 56.43 g of 1-methyl-2-pyrrolidinone, and 41.46 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-44)) showed that the weight average molecular weight of the compound was 6,600 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 52%.
- In a three-neck flask equipped with a stirrer, a thermometer, and a Dimroth condenser, 18.55 g of 4,4′-difluorobenzophenone, 16.22 g of 1,3-bis(4-amino-3-hydroxyphenoxy)benzene, and 17.32 g of 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene were dissolved in 149.67 g of 1-methyl-2-pyrrolidinone. 41.46 g of potassium carbonate was then added, the air in the system was replaced with a nitrogen gas, and the mixture was reacted in an oil bath at 160° C. for 20 hours. After the reaction was completed, the system was cooled until the temperature became 80° C., and then 26.17 g of propargyl bromide dissolved in 56.43 g of 1-methyl-2-pyrrolidinone, and 41.46 g of potassium carbonate were added. The mixture was stirred at 80° C. for 20 hours to react with a phenol group and an amino group that are at the end of a polymer.
- After the reaction was completed, the reaction solution was filtrated by using a Kiriyama funnel under suction, and a solution, in which 2N-hydrochloric acid and 1-methyl-2-pyrrolidinone were mixed with a ratio of 1:9, was added to the filtrate until it became acidic. A litmus paper was used to confirm acidity of the solution. The obtained solution was dropped into a mixed solution, in which water and methanol were mixed with a ratio of 1:9, and was reprecipitated. After the dropping was completed, the mixture was filtrated by using a Buchner funnel under suction, and then washed for three times with methanol, for two times with water, and finally for three times with methanol. The obtained powder was dried in a vacuum dryer for 12 hours.
- A GPC analysis of the obtained macromolecular compound (corresponding to a compound of Formula (1-45)) showed that the weight average molecular weight of the compound was 28,000 in terms of polystyrene, and the rate of a reaction from a phenol group and an amino group existed at the end to an organic group containing a triple bond was 84%.
- 50 g of a macromolecular compound obtained in Synthesis Example 1 was dissolved in 93 g of cyclohexanone, and then filtered through a polyethylene microfilter having a pore size of 1.0 μm to prepare a composition for forming a passivation film having a solid content of 35% by mass.
- 50 g of a macromolecular compound obtained in Synthesis Example 19 was dissolved in 93 g of cyclohexanone, and then filtered through a polyethylene microfilter having a pore size of 1.0 μm to prepare a composition for forming a passivation film having a solid content of 35% by mass.
- 50 g of a macromolecular compound obtained in Synthesis Example 20 was dissolved in 93 g of cyclohexanone, and then filtered through a polyethylene microfilter having a pore size of 1.0 μm to prepare a composition for forming a passivation film having a solid content of 35% by mass.
- 50 g of a macromolecular compound obtained in Synthesis Example 21 was dissolved in 93 g of cyclohexanone, and then filtered through a polyethylene microfilter having a pore size of 1.0 μm to prepare a composition for forming a passivation film having a solid content of 35% by mass.
- The CYCLOTENE 3022-35 (manufactured by the Dow Chemical Company), which is a benzocyclobutene resin solution, was prepared as a composition for forming a passivation film.
- 50 g of a poly(pyromellitic dianhydride-co-4,4′-oxydianiline) amic acid solution (Pyre-ML RC-5019, a 1-methyl-2-pyrrolidone solution having a solid content of 16% by mass, Sigma-Aldrich Japan K.K.), which is a polyimide precursor, was prepared as a composition for forming a passivation film.
- 50 g of polysulfone (Sigma-Aldrich Japan K.K.) was dissolved in 200 g of 1-methyl-2-pyrrolidone, and then filtered through a polyethylene microfilter having a pore size of 1.0 A polysulfone solution having a solid content of 25% by mass, which is an aromatic polyether, was prepared as a composition for forming a passivation film.
- <Evaluation of Passivation Film>
- Each of passivation films produced with compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was evaluated for solvent-tolerance, heat-tolerance, adhesive force, dry etching, and electrical properties.
- <Solvent-Tolerance>
- Each of compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film. The formed film was immersed in 1-methyl-2-pyrrolidone at 23° C. for 1 minute, and then solvent-tolerance of the film was evaluated with a percentage of a residual film.
- <Evaluation of Heat-Tolerance>
- Each of compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film. The temperature of the formed film in a TG-DTA (manufactured by Bruker AXS K.K., TG/DTA2010SR) was elevated at 10° C./minute, and the heat-tolerance was evaluated from a temperature at which the amount decreases by 3% by mass. The wafer was also placed on a hot plate heated at 260° C., and evaluated for whether the film has tackiness by touching with forceps.
- <Evaluation of Adhesiveness>
- Each of compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater under the condition of 1,500 rpm, 30 seconds, and cured at 200° C. for 30 minutes to form a passivation film. The cross-cut adhesion test (JIS K5400) was conducted to the formed film, and adhesiveness was evaluated with the number of squares remained on the wafer.
- <Evaluation of O2 Dry Etching Property>
- Each of compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3 was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film. Etching was conducted for 2 minutes, by using a reactive ion etching device (RIE-10NR, manufactured by SAMCO INC.) under the oxygen flux of 50 sccm, the pressure of 12 Pa, and the RF output of 250 W, and the dry etching property of the formed film was evaluated as a reduced amount of a film thickness per 1 minute.
- <Evaluation of Electrical Property>
- Diluted solutions were prepared by adding solvents to compositions for forming passivation films obtained in Examples 1 to 4 and Comparative Examples 1 to 3, so that films formed on silicon wafers by using a spin coater have film thicknesses of 1 μm. Each of the prepared diluted solutions was applied onto a silicon wafer by using a spin coater, and cured at 200° C. for 30 minutes to form a passivation film. A voltage of 2 MV/cm was applied to the passivation film by using a mercury probe (CVmap 92-B, manufactured by Four Dimensions Inc.), and a leak current value and permittivity (converted to relative permittivity) were measured to evaluate electrical properties.
- The evaluation results of Examples 1 to 4 and Comparative Examples 1 to 3 are shown in Table 1.
-
TABLE 1 Evaluation Items O2 Dry Etching Heat-tolerance Property Solvent- Temperature Reduced Electrical Property tolerance of 3% by Adhesiveness Amount Leak Percentage of mass Number of of Film Current a Residual Decrease 260° C. Remained Thickness Value Film (° C.) Tackiness Squares (nm) (A/cm2) Permittivity Example 1 95% 371 No 100 501 3.94 × 3.02 or greater 10−10 Example 2 95% 359 No 100 592 3.65 × 3.17 or greater 10−10 Example 3 95% 338 No 100 507 3.91 × 3.32 or greater 10−10 Example 4 95% 346 No 100 490 4.68 × 3.13 or greater 10−10 Comparative 79% 400 No 100 51 2.27 × 2.71 Example 1 10−9 Comparative 95% 272 No 0 703 7.08 × 4.29 Example 2 or greater 10−6 Comparative 0% 481 Yes 100 347 — — Example 3 - As shown in Table 1, the passivation films obtained from the present invention showed good values for all of solvent-tolerance, heat-tolerance, adhesiveness, O2 dry etching properties, and electrical properties.
- The passivation films using polymers obtained in Synthesis Examples 2 to 18 also showed results comparable to those from Examples 1 to 4.
- By contrast, with the benzocyclobutene resin of Comparative Example 1, sufficient solvent-tolerance was not obtained by curing at a low temperature and a short time, that is, 200° C. and 30 minutes. In addition, the O2 dry etching property was also insufficient with this resin.
- With the polyimide resin of Comparative Example 2, imidization was not sufficiently proceeded, and thus dehydration resulting from moisture absorption and progress of imidization markedly decreased thermogravimetry. Electrical properties were extremely poor with this resin, and adhesiveness to the wafer was also not obtained because of high internal stress resulting from heat shrinkage.
- Since the aromatic polyether of Comparative Example 3 does not have any thermal cross-linking groups, solvent-tolerance was not obtained at all, and moreover, the film was melted at 260° C.
- A passivation film obtained from a composition for forming a passivation film of the present invention has excellent solvent-tolerance, heat-tolerance, adhesiveness, O2 dry etching properties, electrical properties and the like. By utilizing such properties, a passivation film of the present invention can be used as a film protecting an IC circuit formed on a wafer, a film protecting an electrode formed on the rear surface of a wafer, and the like.
Claims (18)
1. A composition for forming a passivation film, comprising:
a polymer containing a unit structure of Formula (i):
T0-O Formula (i)
T0-O Formula (i)
(where T0 is a sulfonyl group, a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group), wherein
the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at an end, in a side chain, or in a main chain of the polymer:
2. A composition for forming a passivation film, comprising:
a polymer containing a unit structure of Formula (1):
L1-O-T1-O Formula (1)
L1-O-T1-O Formula (1)
(where L1 is an arylene group optionally having a substituent, or is a combination of an arylene group optionally having a substituent and a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and T1 is a fluoroalkylene group, a cycloalkylene group, or an arylene group having a substituent, or is a combination of an arylene group optionally having a substituent and a fluoroalkylene group or a cycloalkylene group, or is a combination of an arylene group optionally having a substituent, a fluoroalkylene group, and a cycloalkylene group), wherein
the polymer has at least one of a group having a structure of Formula (2-A), a group having a structure of Formula (2-B), or a group having both of the structures, at an end, in a side chain, or in a main chain of the polymer:
3. The composition for forming a passivation film according to claim 1 , wherein
the arylene group is a phenylene group, a naphthylene group, or an anthrylene group.
4. The composition for forming a passivation film according to claim 1 , wherein
the polymer is a homopolymer having one type of unit structure.
5. The composition for forming a passivation film according to claim 1 , wherein
the polymer is a copolymer having at least two types of unit structures.
6. The composition for forming a passivation film according to claim 2 , comprising:
a polymer containing a unit structure of Formula (1) where L1 is a group of Formula (3) below, a unit structure of Formula (1) where L1 is a group of Formula (4) below, or a combination of these unit structures:
(where each of R1, R2, and R3 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; L2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4).
7. The composition for forming a passivation film according to claim 2 , comprising:
a polymer containing a unit structure of Formula (1) where T1 is a group of Formula (5) below, a unit structure of Formula (1) where T1 is a group of Formula (6) below, or a combination of these unit structures:
(where each of R4, R5, and R6 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; T2 is a fluoroalkylene group, a cycloalkylene group, or a combination of these groups; and each of n4, n5, and n6 is an integer of 0 to 4).
8. The composition for forming a passivation film according to claim 6 , wherein
in Formula (3), R1 is a group containing at least a cyano group, and n1 is an integer of 1 to 4.
9. The composition for forming a passivation film according to claim 6 , wherein
in Formula (4), L2 is a sulfonyl group or a carbonyl group.
10. The composition for forming a passivation film according to claim 1 , further comprising:
a polymer containing a unit structure of Formula (7):
L3-O-T3-O Formula (7)
L3-O-T3-O Formula (7)
(where L3 is Formula (3) or Formula (4):
(where each of R1, R2, and R3 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; L2 is a sulfonyl group, a carbonyl group, an ester group, an amido group, a sulfinyl group, or a sulfonamide group; and each of n1, n2, and n3 is an integer of 0 to 4), T3 is an alkylene group, a sulfonyl group, a carbonyl group, a C6-30 arylene group optionally having a substituent, or a combination of any of these groups).
11. The composition for forming a passivation film according to claim 1 , wherein
the arylene group is a phenylene group, a naphthylene group, or an anthrylene group.
12. The composition for forming a passivation film according to claim 10 , wherein
T3 is a group of Formula (8):
(where each of R7 and R8 is a C1-10 alkyl group, a C1-4 fluoroalkyl group, a hydroxy group, an allyl group, an allyloxy group, an amino group, a cyano group, a nitro group, an acyl group, an acyloxy group, a carboxy group, a group having a tertiary carbon atom, a cycloalkyl group, or a combination of any of these groups; each of n7 and n8 is an integer of 0 to 4; and T4 is an alkylene group, a sulfonyl group, a carbonyl group, a C6-30 arylene group optionally having a substituent, or a combination of any of these groups).
13. The composition for forming a passivation film according to claim 6 , wherein
the group having a tertiary carbon atom is a tertiary butyl group.
14. The composition for forming a passivation film according to claim 1 , wherein
weight-average molecular weight of the polymer is from 500 to 5,000,000.
15. The composition for forming a passivation film according to claim 1 , further comprising:
a solvent.
16. A passivation film obtained by applying the composition for forming a passivation film as claimed in claim 1 to a substrate, and baking the substrate.
17. The passivation film according to claim 16 , wherein
the passivation film is used as a film protecting an IC circuit formed on a wafer.
18. The passivation film according to claim 16 , wherein
the passivation film is used as a film protecting an electrode formed on a rear surface of a wafer.
Applications Claiming Priority (3)
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JP2012026075 | 2012-02-09 | ||
JP2012-026075 | 2012-02-09 | ||
PCT/JP2013/053067 WO2013118871A1 (en) | 2012-02-09 | 2013-02-08 | Composition for forming passivation film, including resin having carbon-carbon multiple bond |
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PCT/JP2013/053067 A-371-Of-International WO2013118871A1 (en) | 2012-02-09 | 2013-02-08 | Composition for forming passivation film, including resin having carbon-carbon multiple bond |
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US15/202,133 Division US10174168B2 (en) | 2012-02-09 | 2016-07-05 | Composition for forming passivation film, including resin having carbon-carbon multiple bond |
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US14/374,668 Abandoned US20140374887A1 (en) | 2012-02-09 | 2013-02-08 | Composition for forming passivation film, including resin having carbon-carbon multiple bond |
US15/202,133 Active US10174168B2 (en) | 2012-02-09 | 2016-07-05 | Composition for forming passivation film, including resin having carbon-carbon multiple bond |
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US (2) | US20140374887A1 (en) |
JP (1) | JP6311863B2 (en) |
KR (1) | KR102088868B1 (en) |
CN (1) | CN103946271B (en) |
SG (1) | SG11201404585XA (en) |
TW (1) | TWI617592B (en) |
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Cited By (2)
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US20180081273A1 (en) * | 2015-03-30 | 2018-03-22 | Nissan Chemical Industries, Ltd. | Resin composition, method for forming pattern using the same, and method for synthesizing polymer |
US11798810B2 (en) | 2017-01-13 | 2023-10-24 | Nissan Chemical Corporation | Resist underlayer film-forming composition containing amide solvent |
Families Citing this family (2)
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US10253210B2 (en) | 2014-09-17 | 2019-04-09 | Nissan Chemical Industries, Ltd. | Film-forming composition including thermosetting resin |
CN115073740B (en) * | 2022-07-19 | 2023-08-29 | 宁夏清研高分子新材料有限公司 | Polysulfone polymer and preparation method thereof |
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JP2625856B2 (en) * | 1988-04-15 | 1997-07-02 | 東ソー株式会社 | Polyarylene thioether copolymer and method for producing the same |
US5179188A (en) * | 1990-04-17 | 1993-01-12 | Raychem Corporation | Crosslinkable fluorinated aromatic ether composition |
EP0467847A1 (en) * | 1990-07-20 | 1992-01-22 | Ciba-Geigy Ag | Polyarylene ether with tetraphenylethylene units |
DE4110460A1 (en) * | 1991-03-30 | 1992-10-01 | Basf Ag | MODIFIED POLYARYLENETHER WITH IMPROVED ADHESIVE STRENGTH |
JPH09214141A (en) * | 1995-11-29 | 1997-08-15 | Nec Corp | Wiring construction |
TW341022B (en) * | 1995-11-29 | 1998-09-21 | Nippon Electric Co | Interconnection structures and method of making same |
TW561167B (en) * | 1999-09-09 | 2003-11-11 | Sumitomo Chemical Co | Polyether resin and coating solution for forming insulation film |
JP2001151884A (en) * | 1999-11-24 | 2001-06-05 | Sumitomo Chem Co Ltd | Thermosetting polyether resin and production method, thereof and coating solution for forming insulation film layer |
JP5011600B2 (en) * | 2000-09-13 | 2012-08-29 | 住友化学株式会社 | Polyether resin, method for producing the same, and insulating material |
US6716955B2 (en) * | 2002-01-14 | 2004-04-06 | Air Products And Chemicals, Inc. | Poly(arylene ether) polymer with low temperature crosslinking grafts and adhesive comprising the same |
JP2003268101A (en) * | 2002-03-15 | 2003-09-25 | Sumitomo Chem Co Ltd | Polyether resin and method for manufacturing it |
TW562837B (en) * | 2002-05-24 | 2003-11-21 | Ind Tech Res Inst | PPE copolymers, the process of preparing the same and resin composition having the same |
JP2005264008A (en) | 2004-03-19 | 2005-09-29 | Toyobo Co Ltd | Crosslinkable sulfo-containing polyarylene ether compound |
TWI387623B (en) | 2005-06-20 | 2013-03-01 | Manac Inc | Reactive monomer and resin composition including them |
US20080097027A1 (en) * | 2006-10-23 | 2008-04-24 | General Electric Company | Varnish composition for insulating electrical machinery |
JP2009070875A (en) | 2007-09-11 | 2009-04-02 | Alps Electric Co Ltd | Substrate for thick film technology and circuit board |
JP2010065097A (en) | 2008-09-09 | 2010-03-25 | Fujifilm Corp | Polymer, preparation method thereof, composition containing the same and cured product thereof |
JP5790945B2 (en) * | 2010-08-10 | 2015-10-07 | 日産化学工業株式会社 | Adhesive composition containing resin having multiple bonds of carbon and carbon |
JP2013035959A (en) * | 2011-08-09 | 2013-02-21 | Nippon Shokubai Co Ltd | Fluorine-containing aromatic polymer |
JP2013049762A (en) * | 2011-08-30 | 2013-03-14 | Nippon Shokubai Co Ltd | Fluorine-containing aromatic polymer-containing composition |
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2013
- 2013-02-08 WO PCT/JP2013/053067 patent/WO2013118871A1/en active Application Filing
- 2013-02-08 SG SG11201404585XA patent/SG11201404585XA/en unknown
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- 2013-02-08 CN CN201380003965.XA patent/CN103946271B/en active Active
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US20180081273A1 (en) * | 2015-03-30 | 2018-03-22 | Nissan Chemical Industries, Ltd. | Resin composition, method for forming pattern using the same, and method for synthesizing polymer |
US10048585B2 (en) * | 2015-03-30 | 2018-08-14 | Nissan Chemical Industries, Ltd. | Resin composition, method for forming pattern using the same, and method for synthesizing polymer |
US11798810B2 (en) | 2017-01-13 | 2023-10-24 | Nissan Chemical Corporation | Resist underlayer film-forming composition containing amide solvent |
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CN103946271A (en) | 2014-07-23 |
KR102088868B1 (en) | 2020-03-13 |
JPWO2013118871A1 (en) | 2015-05-11 |
TW201348291A (en) | 2013-12-01 |
US10174168B2 (en) | 2019-01-08 |
US20160311979A1 (en) | 2016-10-27 |
JP6311863B2 (en) | 2018-04-18 |
SG11201404585XA (en) | 2014-10-30 |
CN103946271B (en) | 2019-04-12 |
TWI617592B (en) | 2018-03-11 |
WO2013118871A1 (en) | 2013-08-15 |
KR20140128948A (en) | 2014-11-06 |
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