JP6810677B2 - 新規テトラカルボン酸二無水物、ポリイミド樹脂及びその製造方法、感光性樹脂組成物、パターン形成方法及び硬化被膜形成方法、層間絶縁膜、表面保護膜、電子部品 - Google Patents
新規テトラカルボン酸二無水物、ポリイミド樹脂及びその製造方法、感光性樹脂組成物、パターン形成方法及び硬化被膜形成方法、層間絶縁膜、表面保護膜、電子部品 Download PDFInfo
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- JP6810677B2 JP6810677B2 JP2017233394A JP2017233394A JP6810677B2 JP 6810677 B2 JP6810677 B2 JP 6810677B2 JP 2017233394 A JP2017233394 A JP 2017233394A JP 2017233394 A JP2017233394 A JP 2017233394A JP 6810677 B2 JP6810677 B2 JP 6810677B2
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- 239000011342 resin composition Substances 0.000 title claims description 147
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 title claims description 106
- 229920001721 polyimide Polymers 0.000 title claims description 102
- 239000009719 polyimide resin Substances 0.000 title claims description 82
- 125000006158 tetracarboxylic acid group Chemical group 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 31
- 230000001681 protective effect Effects 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000011229 interlayer Substances 0.000 title claims description 6
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 claims description 134
- 230000015572 biosynthetic process Effects 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 60
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 56
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 43
- 239000007864 aqueous solution Substances 0.000 claims description 41
- 239000000758 substrate Substances 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000000962 organic group Chemical group 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 30
- 150000004985 diamines Chemical class 0.000 claims description 20
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 19
- 239000003431 cross linking reagent Substances 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 13
- 238000004090 dissolution Methods 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 238000011417 postcuring Methods 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000003504 photosensitizing agent Substances 0.000 claims description 8
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 238000010894 electron beam technology Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
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- 239000002585 base Substances 0.000 description 26
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 25
- 239000007983 Tris buffer Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000004642 Polyimide Substances 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 19
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- 238000011161 development Methods 0.000 description 15
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- 150000008065 acid anhydrides Chemical class 0.000 description 14
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 12
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000000565 sealant Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 8
- 239000004962 Polyamide-imide Substances 0.000 description 7
- 125000002723 alicyclic group Chemical group 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 150000001805 chlorine compounds Chemical class 0.000 description 7
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 7
- 229920002312 polyamide-imide Polymers 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 229910021642 ultra pure water Inorganic materials 0.000 description 7
- 239000012498 ultrapure water Substances 0.000 description 7
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 6
- CARNFEUGBMWTON-UHFFFAOYSA-N 3-(2-prop-2-enoxyethoxy)prop-1-ene Chemical compound C=CCOCCOCC=C CARNFEUGBMWTON-UHFFFAOYSA-N 0.000 description 6
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000007514 bases Chemical class 0.000 description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920005575 poly(amic acid) Polymers 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000008393 encapsulating agent Substances 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 5
- 239000011253 protective coating Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 150000003672 ureas Chemical class 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 4
- 229920002577 polybenzoxazole Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
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- 239000010703 silicon Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- PAPNRQCYSFBWDI-UHFFFAOYSA-N DMP Natural products CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000007974 melamines Chemical class 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 3
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- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 2
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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Description
(A)上記一般式(5)で示される構造単位を含むものであるポリイミド樹脂、
(B)光により酸を発生しアルカリ水溶液に対する溶解速度が増大する感光剤であって、キノンジアジド構造を有する化合物、及び
(D)溶剤、
を含むものであるポジ型感光性樹脂組成物を提供する。
(A)上記一般式(5)で示される構造単位を含むものであるポリイミド樹脂、
(B)光により酸を発生しアルカリ水溶液に対する溶解速度が増大する感光剤であって、キノンジアジド構造を有する化合物、
(C)ホルムアルデヒド又はホルムアルデヒド−アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基又はグリシジル基を有する基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(C−1)で示される置換基に置換した化合物、及び下記式(C−2)又は(C−2´)で示される基を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤、及び
(D)溶剤、
を含むものであるポジ型感光性樹脂組成物を提供する。
(A’)上記一般式(5)で示される構造単位を含むものであるポリイミド樹脂、
(B’)光酸発生剤、
(C’)ホルムアルデヒド又はホルムアルデヒド−アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基又はグリシジル基を有する基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(C−1)で示される置換基に置換した化合物、及び下記式(C−2)又は(C−2´)で示される基を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤、及び
を含むものであるネガ型感光性樹脂組成物を提供する。
(1)上述のポジ型感光性樹脂組成物を基板上に塗布し、感光材皮膜を形成する工程、
(2)加熱処理後、フォトマスクを介して波長190〜500nmの高エネルギー線もしくは電子線で感光材皮膜を露光する工程、及び
(3)アルカリ水溶液の現像液を用いて現像する工程、
を含むパターン形成方法を提供する。
(I)上述のネガ型感光性樹脂組成物を基板上に塗布し、感光材皮膜を形成する工程、
(II)加熱処理後、フォトマスクを介して波長190〜500nmの高エネルギー線もしくは電子線で感光材皮膜を露光する工程、及び
(III)アルカリ水溶液の現像液を用いて現像する工程、
を含むパターン形成方法を提供する。
本発明のテトラカルボン酸二無水物は下記一般式(1)で示されるものである。
本発明のテトラカルボン酸二無水物の製造方法としては、まず下記一般式(10)又は(11)で示されるアルケニル基含有カルボン酸無水物と下記一般式(12)で示されるジヒドロオルガノシロキサンとを触媒の存在下においてヒドロシリル化反応を行うことによって下記一般式(13)又は(14)で示されるカルボン酸無水物含有ヒドロオルガノシロキサンを得る。次に得られた下記一般式(13)又は(14)で示されるカルボン酸無水物含有ヒドロオルガノシロキサンと下記一般式(15)で示されるアルケニル基を少なくとも二つ以上含有する化合物とを触媒の存在下においてヒドロシリル化反応を行うことで本発明のテトラカルボン酸二無水物を得ることができる。
また、本発明では、上述の本発明のポリイミド樹脂を製造する方法を提供する。上記一般式(5)で示される構造単位を含むポリイミド樹脂を製造するには、まず下記一般式(1)で示されるテトラカルボン酸二無水物と下記一般式(9)で示されるジアミンとを反応させポリアミック酸を得る。
構造単位(5)を含むポリイミド樹脂、あるいは、構造単位(5)及び構造単位(17)を含むものであるポリイミド樹脂の好適な分子量は、好ましくは5,000〜100,000、より好ましくは7,000〜50,000である。分子量が5,000以上であれば、基板上に上記ポリイミド樹脂をベース樹脂に用いた感光性樹脂組成物を所望な膜厚に成膜することが容易になり、分子量が100,000以下であれば、感光性樹脂組成物の粘度が著しく高いものとはならず、成膜できなくなる恐れがない。
次に、本発明のポリイミド樹脂をベース樹脂とした感光性樹脂組成物に関して、説明する。本発明では、上述した本発明のポリイミド樹脂をベース樹脂として用いることにより、ポジ型感光性樹脂組成物やネガ型感光性樹脂組成物を得ることができる。
まず、本発明のポリイミド樹脂をベース樹脂とした感光性樹脂組成物において、アルカリ現像可能なポジ型感光性樹脂組成物について説明する。本発明のポジ型感光性樹脂組成物は、例えば以下に説明する2つの形態とすることができるが、これらに限定されない。
(A)上記一般式(5)で示される構造単位を含むものであるポリイミド樹脂、
(B)光により酸を発生しアルカリ水溶液に対する溶解速度が増大する感光剤であって、キノンジアジド構造を有する化合物、及び
(D)溶剤、
を含むものである。
本発明のポジ型感光性樹脂組成物の第2の形態は、
(A)構造単位(5)を含むポリイミド樹脂、
(B)光により酸を発生しアルカリ水溶液に対する溶解速度が増大する感光剤であって、キノンジアジド構造を有する化合物、
(C)ホルムアルデヒド又はホルムアルデヒド−アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基又はグリシジル基を有する基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(C−1)で示される置換基に置換した化合物、及び下記式(C−2)又は(C−2´)で示される基を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤、及び
(D)溶剤、
を含むものである。
次に、本発明のポリイミド樹脂をベース樹脂とした感光性樹脂組成物において、アルカリ現像可能なネガ型感光性樹脂組成物について説明する。本発明のネガ型感光性樹脂組成物は、例えば以下に説明する形態とすることができるが、これに限定されない。
(A’)構造単位(5)を含むものであるポリイミド樹脂、
(B’)光酸発生剤、
(C’)ホルムアルデヒド又はホルムアルデヒド−アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基又はグリシジル基を有する基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(C−1)で示される置換基に置換した化合物、及び下記式(C−2)又は(C−2´)で示される基を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤、及び
(D)溶剤、
を含むネガ型感光性樹脂組成物である。
次に、本発明のポジ型感光性樹脂組成物及びネガ型感光性樹脂組成物を用いたパターン形成方法に関して、説明を行う。
撹拌機、温度計を具備した1Lのフラスコ内に水素化ナトリウム26.4g(1.1mol)、テトラヒドロフラン100g、を加え、室温で撹拌しているところにエチレングリコール31.0g(0.5mol)を滴下後、室温下で2時間撹拌した。その後、アリルブロマイド242.0g(2.0mol)を滴下し、滴下終了後1時間撹拌した。次に塩化アンモニウムの飽和水溶液100gを加え反応を停止させた。反応液に酢酸エチル
200g、超純水100gを加え分液水洗後、有機層を分取した後、さらに超純水100gで4回洗浄した。得られた有機層の溶媒を留去し、蒸留精製することでエチレングリコールジアリルエーテル60gを得た。
合成例1においてエチレングリコールをジエチレングリコール53.1gに代え、それ以外は同様の処方でジエチレングリコールジアリルエーテル82.0gを得た。
合成例1においてエチレングリコールをプロピレングリコール38.1gに代え、それ以外は同様の処方でプロピレングリコールジアリルエーテル70.3gを得た。
合成例1においてエチレングリコールを1,3−プロパンジオール38.1gに代え、それ以外は同様の処方で1,3−ジアリロキシプロパン68.7gを得た。
撹拌機、温度計、還流冷却器を具備した1Lのフラスコ内に5−ノルボルネン−2,3−ジカルボン酸無水物50g(0.31mol)、1,1,3,3−テトラメチルジシロキサン492g(3.66mol)、塩化白金酸の白金2質量%2−プロパノール溶液0.6g(0.6×10−4mol)、キシレン150gを仕込み、内温80℃まで加熱し、7時間撹拌した。室温まで冷却後、過剰の1,1,3,3−テトラメチルジシロキサンとキシレンを留去後、蒸留精製することで酸無水物含有シロキサン(S−1)77.3gを得た。
合成例5において5−ノルボルネン−2,3−ジカルボン酸無水物をアリルコハク酸無水物42.7gに代え、それ以外は同様の処方で酸無水物含有シロキサン(S−2)77.0gを得た。
撹拌機、温度計、還流冷却器を具備した500mlのフラスコ内に合成例5で得られた酸無水物含有シロキサン(S−1)50g(168mmol)、塩化白金酸の白金2質量%2−プロパノール溶液0.16g(0.16×10−4mol)、キシレン200gを仕込み、80℃まで昇温後、合成例1で得られたエチレングリコールジアリルエーテル11.6g(82mmol)を滴下した。滴下終了後、90℃まで昇温し、2時間撹拌した。室温まで冷却し、活性炭0.6gを加え、1時間撹拌後、活性炭を濾別し、溶媒を留去することでテトラカルボン酸二無水物(X−1)を59.1g得た。
合成例7においてエチレングリコールジアリルエーテルを合成例2で得られたジエチレングリコールジアリルエーテル15.2gに代え、それ以外は同様の処方でテトラカルボン酸二無水物(X−2)62.6gを得た。
合成例7においてエチレングリコールジアリルエーテルを合成例3で得られたプロピレングリコールジアリルエーテル12.7gに代え、それ以外は同様の処方でテトラカルボン酸二無水物(X−3)60.2gを得た。
合成例7においてエチレングリコールジアリルエーテルを合成例4で得られた1,3−ジアリロキシプロパン12.7gに代え、それ以外は同様の処方でテトラカルボン酸二無水物(X−4)60.8gを得た。
合成例7において酸無水物含有シロキサン(S−1)を合成例6で得られた酸無水物含有シロキサン(S−2)46.1gに代え、それ以外は同様の処方でテトラカルボン酸二無水物(X−5)55.3gを得た。
撹拌機、温度計を具備した500mlのフラスコ内に2,2―ビス(3―アミノ―4―ヒドロキシフェニル)ヘキサフルオロプロパン30g(81.9mmol)、N−メチル−2−ピロリドン120gを加え、室温で撹拌し溶解した。次に室温下、3,3’,4,4’−オキシジフタル酸二無水物(ODPA)15.2g(49.1mmol)と合成例7で合成したテトラカルボン酸二無水物(X−1)24.2g(32.8mmol)をN−メチル−2−ピロリドン155gに溶解した溶液を滴下し、滴下終了後室温下3時間撹拌した。その後、この反応液にキシレン40gを加え、180℃で生成する水を系外へ除きながら6時間加熱還流を行った。室温まで冷却後、この反応液を超純水2Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリイミド樹脂(A−1)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量32,000であった。
合成例12においてテトラカルボン酸二無水物(X−1)を合成例8で得られたテトラカルボン酸二無水物(X−2)25.7g(32.8mmol)に代え、それ以外は同様の処方でポリイミド樹脂(A−2)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量33,000であった。
合成例12においてテトラカルボン酸二無水物(X−1)を合成例9で得られたテトラカルボン酸二無水物(X−3)24.7g(32.8mmol)に代え、それ以外は同様の処方でポリイミド樹脂(A−3)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量30,000であった。
合成例12においてテトラカルボン酸二無水物(X−1)を合成例10で得られたテトラカルボン酸二無水物(X−4)24.7g(32.8mmol)に代え、それ以外は同様の処方でポリイミド樹脂(A−4)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量31,000であった。
合成例12においてテトラカルボン酸二無水物(X−1)を合成例11で得られたテトラカルボン酸二無水物(X−5)22.7g(32.8mmol)に代え、それ以外は同様の処方でポリイミド樹脂(A−5)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量29,000であった。
撹拌機、温度計を具備した500mlのフラスコ内に2,2―ビス(3―アミノ―4―ヒドロキシフェニル)ヘキサフルオロプロパン27.0g(73.7mmol)、1,3−ビス(3−アミノフェノキシ)ベンゼン2.4g(8.2mmol)、N−メチル−2−ピロリドン120gを加え、室温で撹拌し溶解した。次に室温下、3,3’,4,4’−オキシジフタル酸二無水物(ODPA)15.2g(49.1mmol)と合成例7で合成したテトラカルボン酸二無水物(X−1)24.2g(32.8mmol)をN−メチル−2−ピロリドン155gに溶解した溶液を滴下し、滴下終了後室温下3時間撹拌した。その後、この反応液にキシレン40gを加え、180℃で生成する水を系外へ除きながら6時間加熱還流を行った。室温まで冷却後、この反応液を超純水2Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリイミド樹脂(A−6)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量34,000であった。
撹拌機、温度計を具備した500mlのフラスコ内に2,2―ビス(3―アミノ―4―ヒドロキシフェニル)ヘキサフルオロプロパン30g(81.9mmol)、N−メチル−2−ピロリドン170gを加え、室温で撹拌し溶解した。次に室温下、3,3’,4,4’−オキシジフタル酸二無水物(s−ODPA)15.2g(49.1mmol)をN−メチル−2−ピロリドン154gに溶解した溶液を滴下し、滴下終了後室温下3時間撹拌した。その後、この反応液にキシレン40gを加え、160℃で生成する水を系外へ除きながら3時間加熱還流を行った。室温まで冷却後、セバシン酸ジクロライド7.8g(32.8mmol)の混合液を5℃以下に保つように滴下した。滴下終了後、室温まで戻し、この反応液を超純水2Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリアミドイミド樹脂(A−7)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量35,000であった。
撹拌機、温度計を具備した500mlのフラスコ内に2,2―ビス(3―アミノ―4―ヒドロキシフェニル)ヘキサフルオロプロパン24g(65.5mmol)、1,3−ビス(3−アミノフェノキシ)ベンゼン4.8g(16.4mmol)、N−メチル−2−ピロリドン170gを加え、室温で撹拌し溶解した。次に室温下、3,3’,4,4’−オキシジフタル酸二無水物(s−ODPA)15.2g(49.1mmol)をN−メチル−2−ピロリドン154gに溶解した溶液を滴下し、滴下終了後室温下3時間撹拌した。その後、この反応液にキシレン40gを加え、160℃で生成する水を系外へ除きながら3時間加熱還流を行った。室温まで冷却後、セバシン酸ジクロライド7.8g(32.8mmol)の混合液を5℃以下に保つように滴下した。滴下終了後、室温まで戻し、この反応液を超純水2Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリアミドイミド樹脂(A−8)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量37,000であった。
上記合成例12〜合成例17及び比較合成例1、2で合成した重合体を使用して、表1〜3に記載した組成と配合量で、樹脂換算40質量%の樹脂組成物を調製した。その後、撹拌、混合、溶解した後、テフロン(登録商標)製0.5μmフィルターで精密濾過を行って感光性樹脂組成物を得た。表中溶剤のGBLはγ−ブチロラクトンを示す。
上記の感光性樹脂組成物1〜18、比較感光性樹脂組成物1〜6をシリコン基板上へ5mLディスペンスした後に基板を回転することによって、即ち、スピンコート法によって、パターン形成後施す後硬化の加熱後に膜厚が10μmとなるように塗布した。即ち、後硬化工程後、膜厚が減少することを予め検討し、後硬化後の仕上がり膜厚が10μmとなるように塗布時の回転数を調整した。
良好:ホールが矩形又は順テーパー形状(ホール上部の寸法が底部の寸法より大きい形状)が観察されたもの
不良:逆テーパー形状(ホール上部の寸法が底部の寸法より小さい形状)、オーバーハン形状(ホール上部が張り出した形状)、又はホール底部に残渣が観察されたもの
上記の感光性樹脂組成物1〜18、比較感光性樹脂組成物1〜6をシリコーンウェハ上へ硬化後の仕上がり膜厚が10μmとなるようにスピンコートした。次に、ホットプレート上120℃、3分間のプリベークを施し、感光性樹脂膜を得た。次に、得られた樹脂の膜厚を光学式膜厚計(大日本スクリーン製VM−1210)で測定した。
上記の感光性樹脂組成物7〜18、比較感光性樹脂組成物3〜6を銅めっき基板上へ硬化後の仕上がり膜厚が10μmとなるようにスピンコートした。次に、ホットプレート上120℃、3分間のプリベークを施した。その後、オーブンを用いて200℃で2時間、窒素パージしながら硬化を行い、感光性樹脂硬化膜を得た。
3…接着剤付きアルミピン、 4…支持台、
5…つかみ、 6…引張方向。
Claims (16)
- (A)請求項3から請求項5のいずれか一項に記載のポリイミド樹脂、
(B)光により酸を発生しアルカリ水溶液に対する溶解速度が増大する感光剤であって、キノンジアジド構造を有する化合物、及び
(D)溶剤、
を含むものであることを特徴とするポジ型感光性樹脂組成物。 - (A)請求項3から請求項5のいずれか一項に記載のポリイミド樹脂、
(B)光により酸を発生しアルカリ水溶液に対する溶解速度が増大する感光剤であって、キノンジアジド構造を有する化合物、
(C)ホルムアルデヒド又はホルムアルデヒド−アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基又はグリシジル基を有する基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(C−1)で示される置換基に置換した化合物、及び下記式(C−2)又は(C−2´)で示される基を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤、及び
(D)溶剤、
を含むものであることを特徴とするポジ型感光性樹脂組成物。 - (A’)請求項3から請求項5のいずれか一項に記載のポリイミド樹脂、
(B’)光酸発生剤、
(C’)ホルムアルデヒド又はホルムアルデヒド−アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基又はグリシジル基を有する基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(C−1)で示される置換基に置換した化合物、及び下記式(C−2)又は(C−2´)で示される基を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤、及び
(D)溶剤、
を含むものであることを特徴とするネガ型感光性樹脂組成物。 - (1)請求項7又は請求項8に記載のポジ型感光性樹脂組成物を基板上に塗布し、感光材皮膜を形成する工程、
(2)加熱処理後、フォトマスクを介して波長190〜500nmの高エネルギー線もしくは電子線で感光材皮膜を露光する工程、及び
(3)アルカリ水溶液の現像液を用いて現像する工程、
を含むことを特徴とするパターン形成方法。 - (I)請求項9に記載のネガ型感光性樹脂組成物を基板上に塗布し、感光材皮膜を形成する工程、
(II)加熱処理後、フォトマスクを介して波長190〜500nmの高エネルギー線もしくは電子線で感光材皮膜を露光する工程、及び
(III)アルカリ水溶液の現像液を用いて現像する工程、
を含むことを特徴とするパターン形成方法。 - 前記工程(II)と前記工程(III)との間に、露光後加熱工程を含むことを特徴とする請求項11に記載のパターン形成方法。
- 請求項10から請求項12のいずれか一項に記載のパターン形成方法により得られたパターン形成された被膜を、温度100〜300℃において加熱して後硬化する工程を含むことを特徴とする硬化被膜形成方法。
- 請求項7又は請求項8に記載のポジ型感光性樹脂組成物、又は請求項9に記載のネガ型感光性樹脂組成物が硬化してなる硬化被膜からなるものであることを特徴とする層間絶縁膜。
- 請求項7又は請求項8に記載のポジ型感光性樹脂組成物、又は請求項9に記載のネガ型感光性樹脂組成物が硬化してなる硬化被膜からなるものであることを特徴とする表面保護膜。
- 請求項14に記載の層間絶縁膜又は請求項15に記載の表面保護膜を有するものであることを特徴とする電子部品。
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US16/196,281 US10919918B2 (en) | 2017-12-05 | 2018-11-20 | Tetracarboxylic dianhydride, polyimide resin and method for producing the same, photosensitive resin compositions, patterning process, method for forming cured film, interlayer insulating film, surface protective film, and electronic parts |
EP18208547.2A EP3495434B1 (en) | 2017-12-05 | 2018-11-27 | Novel tetracarboxylic dianhydride, polyimide resin and method for producing the same, photosensitive resin compositions, patterning process, method for forming cured film, interlayer insulating film, surface protective film, and electronic parts |
TW107143209A TWI681965B (zh) | 2017-12-05 | 2018-12-03 | 新穎之四羧酸二酐、聚醯亞胺樹脂與其製造方法、感光性樹脂組成物、圖案形成方法與硬化被覆膜形成方法、層間絕緣膜、表面保護膜及電子零件 |
KR1020180154393A KR102141739B1 (ko) | 2017-12-05 | 2018-12-04 | 신규 테트라카르복실산이무수물, 폴리이미드 수지 및 그 제조 방법, 감광성 수지 조성물, 패턴 형성 방법 및 경화 피막 형성 방법, 층간 절연막, 표면 보호막, 전자 부품 |
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US11572442B2 (en) | 2020-04-14 | 2023-02-07 | International Business Machines Corporation | Compound, polyimide resin and method of producing the same, photosensitive resin composition, patterning method and method of forming cured film, interlayer insulating film, surface protective film, and electronic component |
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