WO2017188153A1 - Resin composition - Google Patents
Resin composition Download PDFInfo
- Publication number
- WO2017188153A1 WO2017188153A1 PCT/JP2017/016054 JP2017016054W WO2017188153A1 WO 2017188153 A1 WO2017188153 A1 WO 2017188153A1 JP 2017016054 W JP2017016054 W JP 2017016054W WO 2017188153 A1 WO2017188153 A1 WO 2017188153A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- resin composition
- resin
- film
- general formula
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 100
- 229920005989 resin Polymers 0.000 claims abstract description 96
- 239000011347 resin Substances 0.000 claims abstract description 96
- 239000002243 precursor Substances 0.000 claims abstract description 77
- 239000002253 acid Substances 0.000 claims abstract description 43
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 33
- 229920002577 polybenzoxazole Polymers 0.000 claims abstract description 27
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229920001721 polyimide Polymers 0.000 claims abstract description 22
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- 239000004642 Polyimide Substances 0.000 claims abstract description 18
- 239000004962 Polyamide-imide Substances 0.000 claims abstract description 17
- 229920002312 polyamide-imide Polymers 0.000 claims abstract description 17
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 10
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims abstract description 7
- -1 sulfonate compound Chemical class 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 62
- 239000004065 semiconductor Substances 0.000 claims description 43
- 239000000758 substrate Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000003431 cross linking reagent Substances 0.000 claims description 27
- 238000011161 development Methods 0.000 claims description 19
- 239000011229 interlayer Substances 0.000 claims description 19
- 125000000962 organic group Chemical group 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000010410 layer Substances 0.000 claims description 11
- 238000012545 processing Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 33
- 239000010408 film Substances 0.000 description 159
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 44
- 229910052751 metal Inorganic materials 0.000 description 32
- 239000002184 metal Substances 0.000 description 32
- 235000012431 wafers Nutrition 0.000 description 25
- 238000001723 curing Methods 0.000 description 23
- 238000000576 coating method Methods 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 19
- 229910052802 copper Inorganic materials 0.000 description 18
- 239000010949 copper Substances 0.000 description 18
- 238000011156 evaluation Methods 0.000 description 17
- 229910052710 silicon Inorganic materials 0.000 description 17
- 239000010703 silicon Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 230000002378 acidificating effect Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 238000007789 sealing Methods 0.000 description 11
- 206010034972 Photosensitivity reaction Diseases 0.000 description 10
- 230000036211 photosensitivity Effects 0.000 description 10
- 239000002966 varnish Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000003949 imides Chemical group 0.000 description 9
- 239000007769 metal material Substances 0.000 description 9
- 238000006798 ring closing metathesis reaction Methods 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000013256 coordination polymer Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 238000002161 passivation Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 229910000679 solder Inorganic materials 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 229910052719 titanium Inorganic materials 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 230000015654 memory Effects 0.000 description 5
- 238000011417 postcuring Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- LVXPGRWMMNASLZ-UHFFFAOYSA-N CC1=CC=CC=C1C(C=C2C=CCS2)C#N Chemical compound CC1=CC=CC=C1C(C=C2C=CCS2)C#N LVXPGRWMMNASLZ-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 4
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical group [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000004714 phosphonium salts Chemical class 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000009719 polyimide resin Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000001737 promoting effect Effects 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 3
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
- BXVXPASMKWYBFD-UHFFFAOYSA-N 2-[[2-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-6-(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CC=2C(=C(CO)C=C(C)C=2)O)=C1 BXVXPASMKWYBFD-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 2
- OLIGPHACAFRDEN-UHFFFAOYSA-N 4-naphthoquinonediazidesulfonyl group Chemical group [N-]=[N+]=C1C=C(C2=C(C=CC=C2)C1=O)S(=O)=O OLIGPHACAFRDEN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KHLBYJOGKPIERQ-UHFFFAOYSA-N 5-naphthoquinonediazidesulfonyl group Chemical group [N-]=[N+]=C1C=CC2=C(C=CC=C2S(=O)=O)C1=O KHLBYJOGKPIERQ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- 239000009261 D 400 Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000005013 aryl ether group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
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- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- FDMKCPSWFCMGEB-UHFFFAOYSA-N methyl (4-methylsulfanylphenyl) carbonate Chemical compound COC(=O)OC1=CC=C(SC)C=C1 FDMKCPSWFCMGEB-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- YUOMCRCBTBNCCS-JUKUECOXSA-N n-[(2s)-1-[[(5s)-5-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-6-hydroxyhexyl]amino]-1-oxo-3,3-diphenylpropan-2-yl]-6-methylpyridine-3-carboxamide Chemical compound N([C@H](C(=O)NCCCC[C@@H](CO)N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)C(C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)C1=CC=C(C)N=C1 YUOMCRCBTBNCCS-JUKUECOXSA-N 0.000 description 1
- YNDRMAAWTXUJPV-UHFFFAOYSA-N n-cyclohexyl-2-methylidenecyclohexan-1-amine Chemical compound C=C1CCCCC1NC1CCCCC1 YNDRMAAWTXUJPV-UHFFFAOYSA-N 0.000 description 1
- ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- VKGMUJJGIHYISW-UHFFFAOYSA-N naphthalene-1,5-dione diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1(C=CC=C2C(C=CC=C12)=O)=O VKGMUJJGIHYISW-UHFFFAOYSA-N 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- JSKSILUXAHIKNP-UHFFFAOYSA-N naphthalene-1,7-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(C(=O)O)=CC=C21 JSKSILUXAHIKNP-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920003210 poly(4-hydroxy benzoic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JRDBISOHUUQXHE-UHFFFAOYSA-N pyridine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)N=C1C(O)=O JRDBISOHUUQXHE-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- 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
-
- 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
- C08G73/14—Polyamide-imides
-
- 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
- C08G73/22—Polybenzoxazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- 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
- H01L21/18—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 the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3205—Deposition of non-insulating-, e.g. conductive- or resistive-, layers on insulating layers; After-treatment of these layers
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
- H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
- H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
- H01L23/532—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body characterised by the materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/02—Bonding areas; Manufacturing methods related thereto
- H01L2224/04—Structure, shape, material or disposition of the bonding areas prior to the connecting process
- H01L2224/04105—Bonding areas formed on an encapsulation of the semiconductor or solid-state body, e.g. bonding areas on chip-scale packages
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/10—Bump connectors; Manufacturing methods related thereto
- H01L2224/12—Structure, shape, material or disposition of the bump connectors prior to the connecting process
- H01L2224/12105—Bump connectors formed on an encapsulation of the semiconductor or solid-state body, e.g. bumps on chip-scale packages
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/18—High density interconnect [HDI] connectors; Manufacturing methods related thereto
- H01L2224/19—Manufacturing methods of high density interconnect preforms
Definitions
- the present invention relates to a resin composition suitably used for a surface protective film such as a semiconductor element, an interlayer insulating film, and an insulating layer of an organic electroluminescent element.
- resin compositions that can be cured at low temperatures include resins such as polyimide, polybenzoxazole, polybenzimidazole, and polybenzothiazole, and resin compositions containing a thermal crosslinking agent (Patent Document 1), alkali-soluble polyamideimide, light Positive type photosensitive polyamideimide resin composition containing an acid generator, a solvent and a crosslinking agent (Patent Document 2), an alkali-soluble polyimide, a quinonediazide compound, a thermal crosslinking agent, a thermal acid generator and an adhesion improver
- Patent Document 3 A photosensitive polyimide resin composition
- the resin compositions curable by heat treatment at a low temperature of 250 ° C. or lower as disclosed in Patent Documents 1 to 3 have problems in characteristics such as heat resistance and chemical resistance.
- the present invention has the following configuration. That is, (A) An alkali-soluble compound comprising at least one selected from a polybenzoxazole precursor, a polyimide precursor, a polyamideimide precursor, and a copolymer thereof, and having a benzoxazole precursor structure and an aliphatic group Resin, and (B) A resin composition containing a thermal acid generator and (E) an antioxidant.
- alkali-soluble means a pre-baked film formed by the following method, It means that the dissolution rate when immersed in an alkaline aqueous solution described below is 50 nm / min or more. Specifically, a solution in which a resin is dissolved in ⁇ -butyrolactone is applied onto a silicon wafer and prebaked at 120 ° C. for 4 minutes to form a prebaked film having a thickness of 10 ⁇ m ⁇ 0.5 ⁇ m. It means that the dissolution rate obtained from the decrease in film thickness when immersed in a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 1 ° C. for 1 minute and then rinsed with pure water is 50 nm / min or more.
- a component has a fluorine atom.
- the formed film has water repellency, and when developed with an alkaline aqueous solution, the penetration of the alkaline aqueous solution into the interface between the film and the substrate is suppressed.
- the aqueous alkaline solution used for development may be referred to as an alkaline developer.
- the fluorine atom content in the component (A) is preferably 5% by mass or more from the viewpoint of suppressing the penetration of the alkaline aqueous solution into the interface between the film and the substrate, and 20% by mass from the viewpoint of solubility in the alkaline aqueous solution. The following is preferred.
- the alkali-soluble resin as the component (A) has high heat resistance.
- excellent characteristics can be obtained as a planarizing film, an insulating layer, a partition, a protective film, and an interlayer insulating film used in organic light emitting devices, display devices, and semiconductor elements.
- a thing with little outgas amount is preferable.
- a polybenzoxazole precursor, a polyimide precursor, a polyamideimide precursor, and a copolymer thereof are preferable examples.
- the component (A) used in the present invention preferably has a structural unit represented by the following general formula (1). Moreover, you may have another structural unit further. Examples of other structural units in such a case include, but are not limited to, a structure having a skeleton in which two cyclic structures are bonded to a quaternary carbon atom constituting an imide structure or a cyclic structure, and a siloxane structure. Not. When it further has another structural unit, it is preferable to have 50 mol% or more of structural units represented by General formula (1) among the total number of structural units.
- X and Y each independently represent a divalent to octavalent organic group having 2 or more carbon atoms.
- R 1 and R 2 each independently represent hydrogen or a carbon number of 1 Represents an organic group of ⁇ 20, n represents an integer in the range of 10 to 100,000, r and s represent an integer in the range of 0 to 2, and p and q represent an integer in the range of 0 to 4. .
- the component (A) has a benzoxazole precursor structure. By having the benzoxazole precursor structure, the photosensitivity performance is improved, and high extensibility can be imparted to the cured film obtained by curing the resin composition containing the component (A). Ring closure improves heat resistance and chemical resistance.
- (A) component has an aliphatic group.
- the aliphatic group preferably has at least one organic group of an alkylene group and an oxyalkylene group. Specific examples include an alkylene group, a cycloalkylene group, an oxyalkylene group, and an oxycycloalkylene group. Moreover, it is preferable that the said aliphatic group is what is represented by following General formula (2).
- R 3 to R 6 each independently represents an alkylene group having 1 to 6 carbon atoms.
- R 7 to R 14 are each independently hydrogen, fluorine, or alkyl having 1 to 6 carbon atoms.
- X, y and z each independently represents an integer of 0 to 35.
- the aliphatic group has a low UV absorption property, the introduction of the aliphatic group improves i-ray transmission and can simultaneously realize high sensitivity.
- the weight average molecular weight of the component (A) used in the present invention is preferably 600 or more, and more preferably 900 or more, in that the cured film has high extensibility. Moreover, it is preferable that it is 2,000 or less at the point by which the solubility to an alkaline solution is maintained, It is more preferable that it is 1,800 or less, It is further more preferable that it is 1,500 or less.
- the weight average molecular weight (Mw) can be confirmed using GPC (gel permeation chromatography). For example, it can be determined by measuring using N-methyl-2-pyrrolidone (hereinafter sometimes abbreviated as NMP) as a developing solvent and calculating in terms of polystyrene.
- NMP N-methyl-2-pyrrolidone
- the component (A) used in the present invention preferably has a structural unit represented by the general formula (1).
- (OH) p -X- (COOR 1 ) r represents an acid residue.
- X is a divalent to octavalent organic group having 2 or more carbon atoms, and is preferably an organic group having 5 to 40 carbon atoms containing an aromatic ring or an aliphatic group.
- the acid component examples include dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis (carboxyphenyl) hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid.
- dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis (carboxyphenyl) hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid.
- tetracarboxylic acids such as acid, trimesic acid, diphenyl ether tricarboxylic acid, biphenyl tricarboxylic acid, pyromellitic acid, 3,3 ′, 4,4′-biphenyltetracarboxylic acid, 2,3,3 ′, 4′-biphenyl Tetracarboxylic acid, 2,2 ′, 3,3′-biphenyltetracarboxylic acid, 3,3 ′, 4,4′-diphenyl ether tetracarboxylic acid, 3,3 ′, 4,4′-benzophenone tetracarboxylic acid, 2 , 2 ', 3, 3'-Be Zophenone tetracarboxylic acid, 2,2-bis (3,4-dicarboxyphenyl) propane, 2,2-bis (2,3-dicarboxyphenyl) propane, 1,1-bis (3,4-dicarboxy) Phenyl) ethane, 1,1
- R 15 represents an oxygen atom, C (CF 3 ) 2 , or C (CH 3 ) 2 .
- R 16 and R 17 represent a hydrogen atom or a hydroxyl group.
- These acids can be used as they are or as acid anhydrides, halides or active esters.
- diamine used for component (A) examples include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 1, 4-bis (4-aminophenoxy) benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis (4-aminophenoxy) biphenyl, bis ⁇ 4- (4-aminophenoxy) phenyl ⁇ ether, 1,4-bis (4-aminophenoxy) benzene, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′- Diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'
- R 15 represents an oxygen atom, C (CF 3 ) 2 , or C (CH 3 ) 2 .
- R 16 to R 19 each independently represents a hydrogen atom or a hydroxyl group.
- diamines or the corresponding diisocyanate compounds can be used as diamines or the corresponding diisocyanate compounds, trimethylsilylated diamines.
- the component (A) used in the present invention has an aliphatic group. And it is preferable to have an aliphatic group in Y in the said General formula (1). Furthermore, the aliphatic group is more preferably an aliphatic group represented by the general formula (2).
- the component (A) used in the present invention may contain an aliphatic group having a siloxane structure as long as the heat resistance is not lowered, thereby improving the adhesion to the substrate.
- the diamine component include those obtained by copolymerizing 1 to 15 mol% of bis (3-aminopropyl) tetramethyldisiloxane, bis (p-aminophenyl) octamethylpentasiloxane, and the like. .
- the content of the acidic group at the end of the main chain of the alkali-soluble resin derived from the end-capping agent such as monoamine, acid anhydride, acid chloride, monocarboxylic acid is 100 mol% in total of the acid and amine components constituting the resin.
- the content is preferably 2 to 25 mol%.
- the cured film obtained by curing the resin composition of the present invention preferably has a ratio of the benzoxazole precursor structure ring-closed to polybenzoxazole of 30% or more due to the action of the component (B) described later.
- 30% or more is closed, the amount of outgas is small, and a cured film having high heat resistance, high chemical resistance, and high elongation at break can be obtained.
- the component (A) having a structural unit represented by the general formula (1) in the present invention preferably has a weight average molecular weight of 10,000 or more and 50,000 or less.
- a weight average molecular weight of 10,000 or more is preferable because it can improve mechanical properties after curing, and more preferably 20,000 or more.
- a weight average molecular weight of 50,000 or less is preferable because the developability with an aqueous alkali solution can be improved.
- At least one weight average molecular weight may be within the above range.
- the component (A) used in the present invention can be produced by a known method.
- the polybenzoxazole precursor used in the present invention is composed of a benzoxazole precursor, and can be obtained, for example, by a condensation reaction of a bisaminophenol compound and a dicarboxylic acid. Specifically, a dehydrating condensing agent such as dicyclohexylcarbodiimide (DCC) is reacted with an acid, and a bisaminophenol compound is added thereto, or a solution of a bisaminophenol compound added with a tertiary amine such as pyridine is added to a dicarboxylic acid. For example, a solution of dichloride is dropped. Moreover, it may have an imide precursor structure or an imide structure. In that case, when the imide precursor structure in the polybenzoxazole precursor or the imide structure is 100 parts by mass, the content ratio of the benzoxazole precursor structure Is preferably 101 to 10000 parts by mass.
- a dehydrating condensing agent such as dicyclohex
- a benzoxazole precursor structure is introduced into the polyimide precursor by using a diamine having a benzoxazole precursor in advance or by applying the method for producing the polybenzoxazole precursor. Can do.
- the imide precursor structure in the polyimide precursor is 100 parts by mass
- the content of the benzoxazole precursor structure is preferably 1 to 99 parts by mass.
- a method for producing the polyamideimide precursor used in the present invention for example, first, tricarboxylic acid is converted to acid anhydride, and the remaining carboxylic acid is reacted with an acid chloride or a dehydrating condensing agent such as dicyclohexylcarbodiimide (DCC). It can be synthesized by a method of reacting.
- a benzoxazole precursor structure is introduced into the polyamideimide precursor by using a diamine having a benzoxazole precursor in advance or by applying the method for producing the polybenzoxazole precursor. be able to.
- the imide precursor structure in the polyamideimide precursor is 100 parts by mass
- the content of the benzoxazole precursor structure is preferably 50 to 10,000 parts by mass.
- the thermal acid generator (B) used in the present invention has a thermal decomposition starting temperature of 140 ° C. or higher. Moreover, it is preferable that thermal decomposition start temperature is 220 degrees C or less, and it is more preferable that it is 200 degrees C or less.
- the thermal decomposition start temperature here means a boiling point or a decomposition temperature, and the decomposition temperature is a temperature at which thermal decomposition starts before reaching the melting point.
- thermal acid generator examples include sulfonic acid ester compounds and onium salts such as sulfonium salts.
- the acid generated from the thermal acid generator has an acid dissociation constant of 2.0 from the viewpoint of the function as a catalyst for promoting the cyclization of the imide precursor and benzoxazole precursor of the component (A) and the crosslinking reaction.
- the following strong acids are preferred.
- sulfonic acid As the acid generated by thermal decomposition, sulfonic acid, boric acid and the like are preferable.
- boric acid examples include tetrafluoroboric acid and tetrakis (pentafluorophenyl) boric acid.
- R 20 to R 22 each independently represents an aliphatic group having 1 to 12 carbon atoms or an aromatic group having 4 to 12 carbon atoms.
- R 20 to R 22 each independently represents an aliphatic group having 1 to 12 carbon atoms or an aromatic group having 4 to 12 carbon atoms.
- the group may have some hydrogen atoms substituted, and examples of the substituent include halogen groups such as an alkyl group, an acyl group, and a fluorine group.
- onium salts include sulfonium salts and iodonium salts.
- benzenesulfonic acid (4-hydroxyphenyl) dimethylsulfonium
- benzenesulfonic acid (4-((methoxycarbonyl) oxy) phenyl) dimethylsulfonium
- benzenesulfonic acid benzyl (4-hydroxyphenyl) methylsulfonium
- benzene Benzyl sulfonate (4-((methoxycarbonyl) oxy) phenyl) methylsulfonium sulfonate
- camphorsulfonic acid (4-hydroxyphenyl) dimethylsulfonium
- Camphorsulfonic acid (4-((methoxycarbonyl) oxy) phenyl) dimethylsulfonium
- (C) Preferred examples of the compound having at least two oxetanyl groups as the thermal crosslinking agent include “Denacol” ® EX-212L, Denacol EX-214L, Denacol EX-216L, Denacol EX-850L, Denacol EX -321L (above, manufactured by Nagase ChemteX Corporation), GAN, GOT (above, manufactured by Nippon Kayaku Co., Ltd.), “Epicoat” (registered trademark) 828, Epicoat 1002, Epicoat 1750, Epicoat 1007, YX8100-BH30 , E1256, E4250, E4275 (above, manufactured by Japan Epoxy Resins Co., Ltd.), “Epicron” (registered trademark) 850-S, Epicron HP-4032, Epicron HP-7200, Epicron HP-820, Epicron HP-4700, Epicron HP-4 70, Epicron HP4032 (above, manufactured by Dainippon Ink & Chemicals,
- thermal crosslinking agents Two or more thermal crosslinking agents may be used in combination.
- the resin composition of the present invention preferably further contains (D) a photosensitive compound.
- (D) Photosensitivity can be imparted to the resin composition by containing a photosensitive compound.
- Examples of the photosensitive compound include compounds having a group having a naphthoquinone diazide structure (hereinafter sometimes referred to as naphthoquinone diazide compounds), sulfonium salts, phosphonium salts, diazonium salts, iodonium salts, and the like. Furthermore, it can also contain a sensitizer etc. as needed.
- both a 5-naphthoquinone diazide sulfonyl group and a 4-naphthoquinone diazide sulfonyl group are preferably used.
- the 5-naphthoquinonediazide sulfonyl ester compound has an absorption extending to the g-line region of a mercury lamp and is suitable for g-line exposure and full-wavelength exposure.
- the 4-naphthoquinonediazide sulfonyl ester compound has absorption in the i-line region of a mercury lamp and is suitable for i-line exposure.
- the content of the adhesion improving agent after development is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of component (A). By setting it as such a range, the effect of each post-development adhesion improving agent can be fully expressed.
- Examples of the compound represented by the general formula (7) include the following, but are not limited to the following structures.
- the resin composition of the present invention may contain other post-curing adhesion improver in addition to the compound represented by the general formula (7).
- Other post-cure adhesion improvers include alkoxysilane-containing aromatic amine compounds, aromatic amide compounds, or non-aromatic silane compounds. Two or more of these may be contained. By containing these compounds, it is possible to improve the adhesion to the base material after firing or curing.
- alkoxysilane-containing aromatic amine compound and aromatic amide compound are shown below.
- a compound obtained by reacting an aromatic amine compound and an alkoxy group-containing silicon compound may be used.
- an aromatic amine compound and a group that reacts with an amino group such as an epoxy group or a chloromethyl group may be used.
- the content of the other post-curing adhesion improver is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the component (A). By setting it as such a range, adhesiveness with the base material after baking or hardening can be improved. Further, it can also contain a compound that acts as an adhesion improving agent after development and an adhesion improving agent after curing, such as vinyltrimethoxysilane and vinyltriethoxysilane.
- the resin composition of the present invention may contain other alkali-soluble resins in addition to the component (A).
- alkali-soluble polyimide, polybenzoxazole, acrylic polymer copolymerized with acrylic acid, novolac resin, resole resin, polymer containing radical polymerizable monomer having alkali-soluble group, siloxane resin, cyclic olefin resin examples thereof include a resin having a cardo structure, that is, a skeleton structure in which two cyclic structures are bonded to a quaternary carbon atom constituting the cyclic structure.
- Such a resin is soluble in an alkaline solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, and sodium carbonate.
- an alkaline solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, and sodium carbonate.
- the resin composition of the present invention preferably contains a solvent.
- Solvents include N-methyl-2-pyrrolidone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2 -Polar aprotic solvents such as imidazolidinone, N, N'-dimethylpropyleneurea, N, N-dimethylisobutyramide, methoxy-N, N-dimethylpropionamide, tetrahydrofuran, dioxane, propylene glycol monomethyl ether, propylene Ethers such as glycol monoethyl ether, ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, ethyl acetate, butyl acetate, isobutyl acetate, prop
- the dissolution order of each component is not particularly limited, and for example, there is a method of sequentially dissolving compounds having low solubility.
- the rotational speed is preferably set within a range not impairing the performance of the photosensitive colored resin composition, and is usually 200 rpm to 2000 rpm. Even in the case of stirring, it may be heated as necessary, and is usually room temperature to 80 ° C.
- components that tend to generate bubbles when stirring and dissolving such as surfactants and some post-development adhesion improvers, are added after the other components are dissolved, so that Dissolution failure can be prevented.
- the resin film When the resin film has photosensitivity, it is irradiated with actinic radiation through a mask having a desired pattern on the film.
- actinic radiation used for exposure includes ultraviolet rays, visible rays, electron beams, X-rays, etc., but in the present invention, g-rays (436 nm), h-rays (405 nm), i-rays (365 nm), which are general exposure wavelengths. It is preferable to use.
- these alkaline aqueous solutions may contain polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol,
- polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol,
- One or more alcohols such as isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, ketones such as cyclopentanone, cyclohexanone, isobutyl ketone and methyl isobutyl ketone may be contained.
- alcohols such as ethanol and isopropyl alcohol, and esters such as eth
- the resin film thus obtained is subjected to a thermal crosslinking reaction by applying a temperature of 140 ° C. to 280 ° C. to improve heat resistance and chemical resistance (this process may be referred to as a heat treatment process).
- This heat treatment is carried out for 5 minutes to 5 hours by selecting the temperature and raising the temperature stepwise, or by selecting a temperature range and continuously raising the temperature. As an example, heat treatment is performed at 130 ° C. and 200 ° C. for 30 minutes each.
- the curing conditions in the present invention are preferably 140 ° C. or higher and 280 ° C. or lower.
- the curing condition is preferably 140 ° C. or higher, and more preferably 160 ° C. or higher in order to advance the thermal crosslinking reaction.
- the present invention is particularly preferably 280 ° C. or lower in order to provide a cured film excellent by curing at a low temperature, and to suppress a malfunction caused by a thermal history of a semiconductor device to be described later and improve the yield.
- the following is more preferable, and 220 ° C. or lower is further preferable.
- a display device including a first electrode formed on a substrate and a second electrode provided to face the first electrode, specifically, for example, an LCD, an ECD, an ELD, an organic electroluminescent element It can be used for an insulating layer of the display device (organic electroluminescence device) used.
- the cured film formed by curing the resin composition of the present invention has high adhesion to a semiconductor chip on which metal wiring is applied, and is also used as a sealing resin to an epoxy resin or the like. Since it has a high adhesive strength, it is suitably used as an interlayer insulating film provided on an adjacent base material (substrate) composed of two or more materials.
- the resin composition of the present invention is also suitably used for coil parts of inductor devices.
- the heating temperature for obtaining the cured film (B) is preferably heated at 320 ° C. unless the cured film is thermally decomposed.
- the thermal decomposition temperature of the cured film can be analyzed by thermogravimetry (TGA).
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Abstract
Description
(A)ポリベンゾオキサゾール前駆体、ポリイミド前駆体、ポリアミドイミド前駆体、およびそれらの共重合体、から選ばれる1種類以上を含んでなり、かつベンゾオキサゾール前駆体構造および脂肪族基を有するアルカリ可溶性樹脂、ならびに、
(B)熱酸発生剤および(E)酸化防止剤を含有する、樹脂組成物である。 The present invention has the following configuration. That is,
(A) An alkali-soluble compound comprising at least one selected from a polybenzoxazole precursor, a polyimide precursor, a polyamideimide precursor, and a copolymer thereof, and having a benzoxazole precursor structure and an aliphatic group Resin, and
(B) A resin composition containing a thermal acid generator and (E) an antioxidant.
次に記すアルカリ水溶液に浸漬した場合の溶解速度が50nm/分以上であることをいう。詳細には、γ-ブチロラクトンに樹脂を溶解した溶液をシリコンウエハ上に塗布し、120℃で4分間プリベークを行って膜厚10μm±0.5μmのプリベーク膜を形成し、前記プリベーク膜を23±1℃の2.38質量%テトラメチルアンモニウムヒドロキシド水溶液に1分間浸漬した後、純水でリンス処理したときの膜厚減少から求められる溶解速度が50nm/分以上であることをいう。 In the present invention, alkali-soluble means a pre-baked film formed by the following method,
It means that the dissolution rate when immersed in an alkaline aqueous solution described below is 50 nm / min or more. Specifically, a solution in which a resin is dissolved in γ-butyrolactone is applied onto a silicon wafer and prebaked at 120 ° C. for 4 minutes to form a prebaked film having a thickness of 10 μm ± 0.5 μm. It means that the dissolution rate obtained from the decrease in film thickness when immersed in a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 1 ° C. for 1 minute and then rinsed with pure water is 50 nm / min or more.
また、(A)成分は、ベンゾオキサゾール前駆体構造を有する。ベンゾオキサゾール前駆体構造を有することで、感光性能が向上するとともに、(A)成分を含有する樹脂組成物を硬化した硬化膜に対して高伸度性を付与でき、さらに、ベンゾオキサゾール前駆体が閉環することで、耐熱性、耐薬品性が向上する。 (In the general formula (1), X and Y each independently represent a divalent to octavalent organic group having 2 or more carbon atoms. R 1 and R 2 each independently represent hydrogen or a carbon number of 1 Represents an organic group of ˜20, n represents an integer in the range of 10 to 100,000, r and s represent an integer in the range of 0 to 2, and p and q represent an integer in the range of 0 to 4. .)
The component (A) has a benzoxazole precursor structure. By having the benzoxazole precursor structure, the photosensitivity performance is improved, and high extensibility can be imparted to the cured film obtained by curing the resin composition containing the component (A). Ring closure improves heat resistance and chemical resistance.
(A)成分が、脂肪族基を有することにより、(A)成分を含有する樹脂組成物を硬化した硬化膜が高伸度性を有するものとなる。また、(A)成分が脂肪族基を有することにより、樹脂に柔軟性が生まれ、樹脂のベンゾオキサゾール前駆体構造が閉環する場合に発生する応力の増加を抑制できる。このため、ベンゾオキサゾール前駆体構造の脱水閉環に伴う基板ウエハへの応力の増加を抑制することができる。また、脂肪族基は低紫外線吸収性であるため、その導入によりi線透過性が向上し高感度化も同時に実現できる。 (In the general formula (2), R 3 to R 6 each independently represents an alkylene group having 1 to 6 carbon atoms. R 7 to R 14 are each independently hydrogen, fluorine, or alkyl having 1 to 6 carbon atoms. (However, the structures shown in parentheses are different. X, y and z each independently represents an integer of 0 to 35.)
When the component (A) has an aliphatic group, the cured film obtained by curing the resin composition containing the component (A) has high extensibility. In addition, since the component (A) has an aliphatic group, the resin has flexibility, and an increase in stress generated when the benzoxazole precursor structure of the resin is closed can be suppressed. For this reason, it is possible to suppress an increase in stress on the substrate wafer accompanying dehydration and ring closure of the benzoxazole precursor structure. In addition, since the aliphatic group has a low UV absorption property, the introduction of the aliphatic group improves i-ray transmission and can simultaneously realize high sensitivity.
一般式(3)および(4)中、R20~R22はそれぞれ独立に炭素数1~12の脂肪族基、または炭素数4~12の芳香族基を示すが、脂肪族基および芳香族基はその一部の水素原子が置換されていてもよく、置換基としては、アルキル基、アシル基、フッ素基などのハロゲン基が挙げられる。 (In the general formulas (3) and (4), R 20 to R 22 each independently represents an aliphatic group having 1 to 12 carbon atoms or an aromatic group having 4 to 12 carbon atoms.)
In the general formulas (3) and (4), R 20 to R 22 each independently represents an aliphatic group having 1 to 12 carbon atoms or an aromatic group having 4 to 12 carbon atoms. The group may have some hydrogen atoms substituted, and examples of the substituent include halogen groups such as an alkyl group, an acyl group, and a fluorine group.
(C)熱架橋剤が上記一般式(5)で表される構造単位を有することにより、熱架橋剤自体に、柔軟なアルキレン基と剛直な芳香族基を有するため、耐熱性を有しながら、得られる硬化膜の伸度向上と低応力化が可能である。架橋基としては、アクリル基やメチロール基、アルコキシメチル基、エポキシ基が上げられるがこれに限定されない。この中でも、(A)成分のフェノール性水酸基と反応し、硬化膜の耐熱性を向上することができる点と、脱水せずに反応することができる点から、エポキシ基が好ましい。 (In General Formula (5), R 24 and R 25 each independently represent a hydrogen atom or a methyl group. R 23 is a divalent organic group having an alkylene group having 2 or more carbon atoms, and is linear. , branched, and cyclic either good .R 23 is an alkylene group, a cycloalkylene group, an oxyalkylene group, an alkyl silylene group, alkoxy silylene group, an arylene group, oxyarylene group, oxycarbonyl group, a carbonyl group, an arylene group , Vinylene groups, linking groups containing a heterocyclic ring, combinations thereof, and the like, which may further have a substituent.)
(C) Since the thermal crosslinking agent has a structural unit represented by the above general formula (5), the thermal crosslinking agent itself has a flexible alkylene group and a rigid aromatic group, so that it has heat resistance. Thus, it is possible to improve the elongation and reduce the stress of the obtained cured film. Examples of the crosslinking group include, but are not limited to, an acrylic group, a methylol group, an alkoxymethyl group, and an epoxy group. Among these, an epoxy group is preferable because it can react with the phenolic hydroxyl group of the component (A) to improve the heat resistance of the cured film and can react without dehydration.
上記構造の中でも、耐熱性と伸度向上を両立する点から、mは1~2、lは3~7であることが好ましい。 (In the formula, m is an integer of 1 to 5, and l is 1 to 20.)
Among the above structures, m is preferably 1 to 2, and l is preferably 3 to 7 from the viewpoint of achieving both heat resistance and improvement in elongation.
一般式(6)で表される化合物は、例としては以下のものが挙げられるが、これに限定されない。 (In the general formula (6), R 26 represents a hydrogen atom or an alkyl group having 2 or more carbon atoms, R 27 represents an alkylene group having 2 or more carbon atoms, R 28 represents an alkylene group having 2 or more carbon atoms, O A monovalent to tetravalent organic group containing at least one of an atom and an N atom, k represents an integer of 1 to 4. Examples of the monovalent organic group suitable as R 28 include an alkyl group and a cycloalkyl group. Group, alkoxy group, alkyl ether group, alkylsilyl group, alkoxysilyl group, aryl group, aryl ether group, carboxyl group, allyl group, vinyl group, heterocyclic group and the like are divalent organic groups such as carbonyl group, -O -, - NH -, - NHNH -, - NHCO -, - suitable trivalent or tetravalent organic groups as .R 28 which like COO-, organic monovalent or divalent described above Examples include groups in which hydrogen of a group is replaced with a bonding point, and combinations of these groups, which may further have substituents, among which solubility in a developer and metal It is preferable to have an alkyl ether or —NH— from the viewpoint of adhesion, and —NH— is more preferable from the viewpoint of interaction with the component (A) and metal adhesion due to metal complex formation.
Examples of the compound represented by the general formula (6) include, but are not limited to, the following.
一般式(7)で表される化合物を含有することで、加熱硬化後の膜と金属材料、とりわけ銅との密着性を著しく向上させ、剥離を抑制することができる。これは、一般式(7)で表される化合物のS原子やN原子が金属表面と効率良く相互作用することに由来しており、さらに金属面と相互作用しやすい立体構造となっていることに起因する。これらの効果により、本発明の樹脂組成物は、金属材料との接着性に優れた硬化膜を得ることができる。 (In the general formula (7), R 29 ~ R 31 are, O atom or S atom, one of the N atoms, R 29 ~ .t is 0 or 1 indicating the least one S atom of R 31 U and v each represent an integer of 1 or 2. R 32 to R 34 each independently represents a hydrogen atom or an organic group having 1 to 20 carbon atoms, and R 32 to R 34 represent a hydrogen atom. , Alkyl group, cycloalkyl group, alkoxy group, alkyl polyether group, alkylsilyl group, alkoxysilyl group, aryl group, aryl ether group, carboxyl group, carbonyl group, allyl group, vinyl group, heterocyclic group, and combinations thereof And may further have a substituent.)
By containing the compound represented by the general formula (7), adhesion between the heat-cured film and the metal material, particularly copper, can be remarkably improved and peeling can be suppressed. This is derived from the fact that the S atom and N atom of the compound represented by the general formula (7) interact efficiently with the metal surface, and has a three-dimensional structure that easily interacts with the metal surface. caused by. By these effects, the resin composition of this invention can obtain the cured film excellent in adhesiveness with a metal material.
図4に示すように、基板12には絶縁膜13、その上にパターンとして絶縁膜14が形成される。基板12としてはフェライト等が用いられる。本発明の感光性を有する樹脂組成物は絶縁膜13と絶縁膜14のどちらに使用してもよい。このパターンの開口部に金属(Cr、Ti等)膜15が形成され、この上に金属配線(Ag、Cu等)16がめっき形成される。金属配線16(Ag、Cu等)はスパイラル上に形成されている。13~16を形成する工程を複数回繰り返し、積層させることでコイルとしての機能を持たせることができる。最後に金属配線16(Ag、Cu等)は金属配線17(Ag、Cu等)によって電極18に接続され、封止樹脂19により封止される。 FIG. 4 is a cross-sectional view of a coil component of the inductor device showing the embodiment of the present invention.
As shown in FIG. 4, an insulating
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT-8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行った。温度が50℃以下になったところでシリコンウエハを取り出し、硬化膜(A)を得た。また、300~350℃で加熱した硬化膜(B)を得た。これらの硬化膜(A)、および硬化膜(B)の赤外吸収スペクトルを測定し、1050cm-1付近のC-O伸縮振動に起因するピークの吸光度を求めた。赤外吸収スペクトルの測定は、測定装置として「FT-720」(商品名、株式会社堀場製作所製)を使用した。硬化膜(B)の閉環率を100%として、次の式から硬化膜(A)の閉環率を算出した。ここでいう閉環率とは、ポリ(o-ヒドロキシアミド)構造単位の閉環率のことである。 (1) Calculation of the ring closure rate of the cured film A spin coat method using a coating and developing apparatus ACT-8 so that the film thickness after pre-baking for 3 minutes at 120 ° C. on an 8-inch silicon wafer is 11 μm. After coating and pre-baking, the temperature was raised to 200 ° C. or 220 ° C. at 4.0 ° C./min at an oxygen concentration of 20 ppm or less using an inert oven CLH-21CD-S (manufactured by Koyo Thermo System Co., Ltd.). Alternatively, heat treatment was performed at 220 ° C. for 1 hour. When the temperature reached 50 ° C. or lower, the silicon wafer was taken out to obtain a cured film (A). Further, a cured film (B) heated at 300 to 350 ° C. was obtained. The infrared absorption spectra of these cured film (A) and cured film (B) were measured, and the absorbance of the peak due to CO stretching vibration near 1050 cm −1 was determined. For the measurement of the infrared absorption spectrum, “FT-720” (trade name, manufactured by Horiba, Ltd.) was used as a measuring apparatus. The ring closure rate of the cured film (A) was calculated from the following formula, assuming that the ring closure rate of the cured film (B) was 100%. The term “ring closure rate” as used herein refers to the ring closure rate of a poly (o-hydroxyamide) structural unit.
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT-8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行った。温度が50℃以下になったところでシリコンウエハを取り出し、45質量%のフッ化水素酸に5分間浸漬することで、ウエハより樹脂組成物の硬化膜を剥がした。この膜を幅0.5cm、長さ10cmの短冊状に切断し、熱重量測定装置TGDTA6200((株)日立ハイテクサイエンス製)を用いて、室温から400℃まで昇温速度10℃/分で加熱した際の5%重量減少温度を測定した。 (2) Evaluation of heat resistance The varnish is applied and prebaked on an 8-inch silicon wafer by spin coating using a coating / developing apparatus ACT-8 so that the film thickness after prebaking at 120 ° C. for 3 minutes is 11 μm. Then, using an inert oven CLH-21CD-S (manufactured by Koyo Thermo System Co., Ltd.), the temperature was raised to 200 ° C. or 220 ° C. at 4.0 ° C./min at an oxygen concentration of 20 ppm or less, and 200 ° C. or 220 ° C. For 1 hour. When the temperature became 50 ° C. or lower, the silicon wafer was taken out and immersed in 45% by mass of hydrofluoric acid for 5 minutes to peel off the cured film of the resin composition from the wafer. This film is cut into strips having a width of 0.5 cm and a length of 10 cm and heated from room temperature to 400 ° C. at a heating rate of 10 ° C./min using a thermogravimetric measuring device TGDTA6200 (manufactured by Hitachi High-Tech Science Co., Ltd.). The 5% weight loss temperature was measured.
ワニスを、シリコンウエハ上に120℃で3分間プリベークを行った後の膜厚が10μmとなるように塗布現像装置ACT-8を用いてスピンコート法で塗布し、プリベークした後、イナートオーブンCLH-21CD-Sを用いて、窒素気流下において酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行なった。温度が50℃以下になったところでシリコンウエハを取り出し、その硬化膜を有機薬液(ジメチルスルホキシド:25%水酸化テトラメチルアンモニウム水溶液=92:2)に65℃で100分間浸漬させ、パターンの剥がれや溶出の有無を観察した。 (3) Evaluation of chemical resistance The varnish was applied by spin coating using a coating / developing apparatus ACT-8 so that the film thickness after pre-baking on a silicon wafer at 120 ° C. for 3 minutes would be 10 μm. After pre-baking, using an inert oven CLH-21CD-S, the temperature was raised to 200 ° C. or 220 ° C. at 4.0 ° C./min with an oxygen concentration of 20 ppm or less and heated at 200 ° C. or 220 ° C. for 1 hour. Processing was performed. When the temperature is 50 ° C. or lower, the silicon wafer is taken out, and the cured film is immersed in an organic chemical solution (dimethyl sulfoxide: 25% tetramethylammonium hydroxide aqueous solution = 92: 2) at 65 ° C. for 100 minutes. The presence or absence of elution was observed.
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT-8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行なった。温度が50℃以下になったところでシリコンウエハを取り出し、45質量%のフッ化水素酸に5分間浸漬することで、ウエハより樹脂組成物の硬化膜を剥がした。この膜を幅1cm、長さ9cmの短冊状に切断し、テンシロンRTM-100((株)オリエンテック製)を用いて、室温23.0℃、湿度45.0%RH下で引張速度50mm/分で引っ張り、破断点伸度の測定を行なった。測定は1検体につき10枚の短冊について行ない、結果から上位5点の平均値を求めた。 (4) -1. Evaluation of elongation at break After coating and pre-baking varnish on an 8-inch silicon wafer by spin coating using coating / developing apparatus ACT-8 so that the film thickness after pre-baking at 120 ° C. for 3 minutes is 11 μm Using an inert oven CLH-21CD-S (manufactured by Koyo Thermo System Co., Ltd.), the temperature was raised to 200 ° C. or 220 ° C. at 4.0 ° C./min at an oxygen concentration of 20 ppm or less, and 1 at 200 ° C. or 220 ° C. Heat treatment was performed for a time. When the temperature became 50 ° C. or lower, the silicon wafer was taken out and immersed in 45% by mass of hydrofluoric acid for 5 minutes to peel off the cured film of the resin composition from the wafer. This film was cut into strips having a width of 1 cm and a length of 9 cm, and using Tensilon RTM-100 (manufactured by Orientec Co., Ltd.) at a room temperature of 23.0 ° C. and a humidity of 45.0% RH, a tensile rate of 50 mm / The sample was pulled in minutes and the elongation at break was measured. The measurement was performed on 10 strips per specimen, and the average value of the top 5 points was obtained from the results.
銅配線での剥離評価を行うにあたり、以下の評価基板を準備した。 (4) -2. Peeling evaluation with copper wiring after high temperature storage test (High Temperature Storage, HTS) In performing peeling evaluation with copper wiring, the following evaluation substrates were prepared.
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(セントラル硝子(株)製、以下、BAHFとする。)18.3g(0.05モル)をアセトン100mL、プロピレンオキシド(東京化成(株)製)17.4g(0.3モル)に溶解させ、-15℃に冷却した。ここに3-ニトロベンゾイルクロリド(東京化成(株)製)20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、-15℃で4時間撹拌し、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。 <Synthesis Example 1 Synthesis of Hydroxyl Group-Containing Diamine Compound>
18.3 g (0.05 mol) of 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (manufactured by Central Glass Co., Ltd., hereinafter referred to as BAHF) 100 mL of acetone, propylene oxide (Tokyo) The product was dissolved in 17.4 g (0.3 mol) manufactured by Kasei Co., Ltd. and cooled to -15 ° C. A solution prepared by dissolving 20.4 g (0.11 mol) of 3-nitrobenzoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) in 100 mL of acetone was added dropwise thereto. After completion of dropping, the mixture was stirred at −15 ° C. for 4 hours and then returned to room temperature. The precipitated white solid was filtered off and vacuum dried at 50 ° C.
乾燥窒素気流下、3,3’,4,4’-ジフェニルエーテルテトラカルボン酸二無水物(以降ODPAと呼ぶ)31.0g(0.10モル)をNMP500gに溶解させた。ここに合成例1で得られたヒドロキシル基含有ジアミン化合物39.30g(0.065モル)と1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)をNMP50gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。続いて、プロピレンオキシド及びテトラメチレンエーテルグリコール構造を含むRT-1000(10.00g、0.010モル)をNMP10gとともに加えて、50℃で1時間反応させた。次に末端封止剤として4-アミノフェノール4.36g(0.04モル)をNMP5gとともに加え、50℃で2時間反応させた。その後、N,N-ジメチルホルムアミドジメチルアセタール28.6g(0.24モル)をNMP50gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のアルカリ可溶性樹脂であるポリイミド前駆体(A-1)を得た。 <Synthesis Example 2 Synthesis of Polyimide Precursor (A-1)>
Under a dry nitrogen stream, 31.0 g (0.10 mol) of 3,3 ′, 4,4′-diphenyl ether tetracarboxylic dianhydride (hereinafter referred to as ODPA) was dissolved in 500 g of NMP. Here, 39.30 g (0.065 mol) of the hydroxyl group-containing diamine compound obtained in Synthesis Example 1 and 1.24 g (0.005 mol) of 1,3-bis (3-aminopropyl) tetramethyldisiloxane were mixed with 50 g of NMP. And reacted at 20 ° C. for 1 hour and then at 50 ° C. for 2 hours. Subsequently, RT-1000 (10.00 g, 0.010 mol) containing propylene oxide and a tetramethylene ether glycol structure was added together with 10 g of NMP and reacted at 50 ° C. for 1 hour. Next, 4.36 g (0.04 mol) of 4-aminophenol as an end-capping agent was added together with 5 g of NMP, and reacted at 50 ° C. for 2 hours. Thereafter, a solution obtained by diluting 28.6 g (0.24 mol) of N, N-dimethylformamide dimethylacetal with 50 g of NMP was added dropwise over 10 minutes. After dropping, the mixture was stirred at 50 ° C. for 3 hours. After completion of the stirring, the solution was cooled to room temperature, and then the solution was poured into 3 L of water to obtain a white precipitate. This precipitate was collected by filtration, washed 3 times with water, and then dried for 24 hours in a vacuum dryer at 80 ° C. to obtain a polyimide precursor (A-1) which was the target alkali-soluble resin.
乾燥窒素気流下、BAHF27.47g、(0.075モル)をNMP257gに溶解させた。ここに、1,1’-(4,4’-オキシベンゾイル)ジイミダゾール(以降PBOMと呼ぶ)(17.20g、0.048モル)をNMP20gとともに加えて、85℃で3時間反応させた。続いて、プロピレンオキシド及びテトラメチレンエーテルグリコール構造を含むRT-1000(20.00g、0.020モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(1.24g、0.005モル)、PBOM(14.33g、0.044モル)をNMP50gとともに加えて、85℃で1時間反応させた。さらに、末端封止剤として、5-ノルボルネン-2,3-ジカルボン酸無水物(3.94g、0.024モル)をNMP10gとともに加えて、85℃で30分反応させた。反応終了後、室温まで冷却し、酢酸(52.82g、0.50モル)をNMP87gとともに加えて、室温で1時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリベンゾオキサゾール前駆体(A-2)の粉末を得た。 <Synthesis Example 3 Synthesis of Polybenzoxazole Precursor (A-2)>
Under a dry nitrogen stream, 27.47 g of BAHF (0.075 mol) was dissolved in 257 g of NMP. To this was added 1,1 ′-(4,4′-oxybenzoyl) diimidazole (hereinafter referred to as PBOM) (17.20 g, 0.048 mol) together with 20 g of NMP, and the mixture was reacted at 85 ° C. for 3 hours. Subsequently, RT-1000 containing propylene oxide and tetramethylene ether glycol structures (20.00 g, 0.020 mol), 1,3-bis (3-aminopropyl) tetramethyldisiloxane (1.24 g, 0.005). Mol), PBOM (14.33 g, 0.044 mol) was added together with 50 g of NMP and reacted at 85 ° C. for 1 hour. Further, 5-norbornene-2,3-dicarboxylic acid anhydride (3.94 g, 0.024 mol) was added as a terminal blocking agent together with 10 g of NMP and reacted at 85 ° C. for 30 minutes. After completion of the reaction, the reaction solution was cooled to room temperature, acetic acid (52.82 g, 0.50 mol) was added together with 87 g of NMP, and the mixture was stirred at room temperature for 1 hour. After stirring, the solution was poured into 3 L of water to obtain a white precipitate. The precipitate was collected by filtration, washed with water three times, and then dried for 3 days in a ventilating dryer at 50 ° C. to obtain a polybenzoxazole precursor (A-2) powder.
前記合成例3に従って、BAHF(27.47g、0.075モル)、PBOM(30.10g、0.084モル)、プロピレンオキシド及びエチレングリコール構造を含むED-900(9.00g、0.020モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(1.24g、0.0050モル)、5-ノルボルネン-2,3-ジカルボン酸無水物(5.25g、0.032モル)、酢酸(48.02g、0.80モル)、NMP409gを用いて同様に行い、ポリベンゾオキサゾール前駆体(A-3)の粉末を得た。 <Synthesis Example 4 Synthesis of Polybenzoxazole Precursor (A-3)>
According to Synthesis Example 3, BAHF (27.47 g, 0.075 mol), PBOM (30.10 g, 0.084 mol), ED-900 (9.00 g, 0.020 mol) containing propylene oxide and ethylene glycol structures. ), 1,3-bis (3-aminopropyl) tetramethyldisiloxane (1.24 g, 0.0050 mol), 5-norbornene-2,3-dicarboxylic anhydride (5.25 g, 0.032 mol) , Acetic acid (48.02 g, 0.80 mol) and NMP 409 g were used in the same manner to obtain a polybenzoxazole precursor (A-3) powder.
前記合成例3に従って、BAHF(32.96g、0.090モル)、PBOM(29.38g、0.082モル)、RT-1000(10.00g、0.010モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(1.49g、0.0060モル)、5-ノルボルネン-2,3-ジカルボン酸無水物(5.91g、0.036モル)、HFHA(0.60g、0.0010モル)、ODPA(2.17g、0.0070モル)、酢酸(49.22g、0.82モル)、NMP360gを用いて同様に行い、ポリベンゾオキサゾール前駆体(A-4)の粉末を得た。 <Synthesis Example 5 Synthesis of Polybenzoxazole Precursor (A-4)>
According to Synthesis Example 3, BAHF (32.96 g, 0.090 mol), PBOM (29.38 g, 0.082 mol), RT-1000 (10.00 g, 0.010 mol), 1,3-bis ( 3-aminopropyl) tetramethyldisiloxane (1.49 g, 0.0060 mol), 5-norbornene-2,3-dicarboxylic anhydride (5.91 g, 0.036 mol), HFHA (0.60 g, 0 .0010 mol), ODPA (2.17 g, 0.0070 mol), acetic acid (49.22 g, 0.82 mol), and NMP 360 g, and the polybenzoxazole precursor (A-4) powder was obtained. Obtained.
乾燥窒素気流下、無水ジフェニルエーテルトリカルボン酸クロリド27.5g(0.10モル)をNMP500gに溶解させた。ここに合成例1で得られたヒドロキシル基含有ジアミン化合物39.30g(0.065モル)と1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)をNMP50gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。続いて、プロピレンオキシド及びテトラメチレンエーテルグリコール構造を含むRT-1000(10.00g、0.010モル)をNMP10gとともに加えて、50℃で1時間反応させた。次に末端封止剤として4-アミノフェノール4.36g(0.04モル)をNMP5gとともに加え、50℃で2時間反応させた。その後、N,N-ジメチルホルムアミドジメチルアセタール28.6g(0.24モル)をNMP50gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリアミドイミド前駆体(A-5)を得た。 <Synthesis Example 6 Synthesis of Polyamideimide Precursor (A-5)>
Under a dry nitrogen stream, 27.5 g (0.10 mol) of anhydrous diphenyl ether tricarboxylic acid chloride was dissolved in 500 g of NMP. Here, 39.30 g (0.065 mol) of the hydroxyl group-containing diamine compound obtained in Synthesis Example 1 and 1.24 g (0.005 mol) of 1,3-bis (3-aminopropyl) tetramethyldisiloxane were mixed with 50 g of NMP. And reacted at 20 ° C. for 1 hour and then at 50 ° C. for 2 hours. Subsequently, RT-1000 (10.00 g, 0.010 mol) containing propylene oxide and a tetramethylene ether glycol structure was added together with 10 g of NMP and reacted at 50 ° C. for 1 hour. Next, 4.36 g (0.04 mol) of 4-aminophenol as an end-capping agent was added together with 5 g of NMP, and reacted at 50 ° C. for 2 hours. Thereafter, a solution obtained by diluting 28.6 g (0.24 mol) of N, N-dimethylformamide dimethylacetal with 50 g of NMP was added dropwise over 10 minutes. After dropping, the mixture was stirred at 50 ° C. for 3 hours. After completion of the stirring, the solution was cooled to room temperature, and then the solution was poured into 3 L of water to obtain a white precipitate. This precipitate was collected by filtration, washed with water three times, and then dried in a vacuum dryer at 80 ° C. for 24 hours to obtain the target polyamideimide precursor (A-5).
得られた(A)成分(A-1~5)10gに(B)熱酸発生剤として3-(5-(((フェニルスルホニルオキシ)イミノ)チオフェン-2(5H)-イリデン-2-(o-トリル)プロパンニトリル(B-1)を0.2g(0.52ミリモル)、またはSI-200(B-2)を0.2g(0.53ミリモル)、(C)熱架橋剤としてHMOM-TPHAP(C-1)を2.4g(4.2ミリモル)とMW-100LM(C-2)を1.0g(2.6ミリモル)、(D)感光性化合物として下記式で表される感光性化合物を2.0g(1.8ミリモル)加え、溶剤としてγ-ブチロラクトンを20g加えてワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表1に示す。 [Reference Examples 1 to 15]
To 10 g of the obtained component (A) (A-1 to 5), (B) 3- (5-(((phenylsulfonyloxy) imino) thiophene-2 (5H) -ylidene-2- ( o-Tolyl) propanenitrile (B-1) 0.2 g (0.52 mmol), or SI-200 (B-2) 0.2 g (0.53 mmol), (C) HMOM as thermal crosslinker -TPHAP (C-1) 2.4 g (4.2 mmol) and MW-100LM (C-2) 1.0 g (2.6 mmol), (D) represented by the following formula as a photosensitive compound 2.0 g (1.8 mmol) of a photosensitive compound was added, 20 g of γ-butyrolactone was added as a solvent to prepare a varnish, and these characteristics were measured by the above evaluation methods.
(B)熱酸発生剤を用いない以外は参考例1~15と同様にワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表1に示す。 [Reference Examples 16 to 20]
(B) Varnishes were prepared in the same manner as in Reference Examples 1 to 15 except that no thermal acid generator was used, and these characteristics were measured by the above evaluation methods. The obtained results are shown in Table 1.
得られた(A)成分(A-1~5)10gに(B)熱酸発生剤として3-(5-(((フェニルスルホニルオキシ)イミノ)チオフェン-2(5H)-イリデン-2-(o-トリル)プロパンニトリル(B-1)を0.2g(0.52ミリモル)、またはSI-200(B-2)を0.2g(0.53ミリモル)、または0.5g(1.3ミリモル)、または0.8g(2.1ミリモル)(C)熱架橋剤としてHMOM-TPHAP(C-1)を2.4g(4.2ミリモル)とMW-100LM(C-2)を1.0g(2.6ミリモル)、または下記式で表される熱架橋剤(C-3)を0.2g(0.25ミリモル)、または1.5g(1.9ミリモル)、または5.1g(6.5ミリモル)(D)感光性化合物として下記式で表される感光性化合物を2.0g(1.8ミリモル)、(E)酸化防止剤として下記式で表される化合物(E-1)を0.15g(0.26ミリモル)または(E-2)を0.15g(0.27ミリモル)加え、溶剤としてγ-ブチロラクトンを20g加えてワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表2に示す。 [Examples 1 to 8, Comparative Examples 1 to 9]
To 10 g of the obtained component (A) (A-1 to 5), (B) 3- (5-(((phenylsulfonyloxy) imino) thiophene-2 (5H) -ylidene-2- ( o-tolyl) propanenitrile (B-1) 0.2 g (0.52 mmol), or SI-200 (B-2) 0.2 g (0.53 mmol), or 0.5 g (1.3 Mmol), or 0.8 g (2.1 mmol) (C) 2.4 g (4.2 mmol) of HMOM-TPHAP (C-1) and 1. MW-100LM (C-2) as thermal crosslinkers. 0 g (2.6 mmol), or 0.2 g (0.25 mmol), or 1.5 g (1.9 mmol), or 5.1 g of a thermal crosslinking agent (C-3) represented by the following formula: 6.5 mmol) (D) Photosensitivity represented by the following formula as a photosensitive compound 2.0 g (1.8 mmol) of the compound, 0.15 g (0.26 mmol) of the compound (E-1) represented by the following formula (E) as an antioxidant, or 0.02 of (E-2). 15 g (0.27 mmol) was added, and 20 g of γ-butyrolactone was added as a solvent to prepare a varnish, and these characteristics were measured by the above evaluation method, and the results obtained are shown in Table 2.
(B)熱酸発生剤を用いない以外は比較例2および6~9と同様にワニスを作製(比較例10~14)、または、(B)熱酸発生剤としてSI-200(B-2)を1.2g(3.2ミリモル)加えた以外は比較例2と同様にワニスを作製(比較例15)し、これらの特性を上記評価方法により測定した。得られた結果を表2に示す。 [Comparative Examples 10 to 15]
(B) Varnishes were prepared in the same manner as Comparative Examples 2 and 6 to 9 except that no thermal acid generator was used (Comparative Examples 10 to 14), or (B) SI-200 (B-2 as a thermal acid generator) ) Was added in the same manner as in Comparative Example 2 except that 1.2 g (3.2 mmol) was added (Comparative Example 15), and these characteristics were measured by the above evaluation method. The obtained results are shown in Table 2.
2 Alパッド
3 パッシベーション膜
4 絶縁膜
5 金属(Cr、Ti等)膜
6 金属配線(Al、Cu等)
7 絶縁膜
8 バリアメタル
9 スクライブライン
10 ハンダバンプ
11 封止樹脂
12 基板
13 絶縁膜
14 絶縁膜
15 金属(Cr、Ti等)膜
16 金属配線(Ag、Cu等)
17 金属配線(Ag、Cu等)
18 電極
19 封止樹脂 1
7 Insulating
17 Metal wiring (Ag, Cu, etc.)
18
Claims (20)
- (A)ポリベンゾオキサゾール前駆体、ポリイミド前駆体、ポリアミドイミド前駆体、およびそれらの共重合体、から選ばれる1種類以上を含んでなり、かつベンゾオキサゾール前駆体構造および脂肪族基を有するアルカリ可溶性樹脂、ならびに、
(B)熱酸発生剤および(E)酸化防止剤を含有する、樹脂組成物。 (A) An alkali-soluble compound comprising at least one selected from a polybenzoxazole precursor, a polyimide precursor, a polyamideimide precursor, and a copolymer thereof, and having a benzoxazole precursor structure and an aliphatic group Resin, and
(B) A resin composition containing a thermal acid generator and (E) an antioxidant. - 前記(A)ポリベンゾオキサゾール前駆体、ポリイミド前駆体、ポリアミドイミド前駆体、およびそれらの共重合体、から選ばれる1種類以上を含んでなり、かつベンゾオキサゾール前駆体構造および脂肪族基を有するアルカリ可溶性樹脂が、
一般式(1)で表される構造単位を有する、請求項1に記載の樹脂組成物。
The resin composition of Claim 1 which has a structural unit represented by General formula (1).
- 前記脂肪族基が、アルキレン基およびオキシアルキレン基のうち少なくともいずれかの有機基を有する、請求項1または2に記載の樹脂組成物。 The resin composition according to claim 1 or 2, wherein the aliphatic group has at least one organic group of an alkylene group and an oxyalkylene group.
- 前記脂肪族基が、下記一般式(2)で表される、請求項1~3のいずれかに記載の樹脂組成物。
- 前記一般式(1)におけるYが、下記一般式(2)で表される脂肪族基を有する、請求項2に記載の樹脂組成物。
- 前記(B)熱酸発生剤が、下記一般式(3)で表されるスルホン酸エステル化合物、一般式(4)で表されるスルホン酸エステル化合物、およびオニウム塩、から選ばれる1種類以上の化合物を含む、請求項1~5のいずれかに記載の樹脂組成物。
- 前記(B)熱酸発生剤の熱分解開始温度が、140℃以上220℃以下である、請求項1~6のいずれかに記載の樹脂組成物。 The resin composition according to any one of claims 1 to 6, wherein the thermal decomposition starting temperature of the thermal acid generator (B) is 140 ° C or higher and 220 ° C or lower.
- さらに、(C)熱架橋剤および(D)感光性化合物を含有する、請求項1~7のいずれかに記載の樹脂組成物。 The resin composition according to any one of claims 1 to 7, further comprising (C) a thermal crosslinking agent and (D) a photosensitive compound.
- 前記(C)熱架橋剤が、一般式(5)で表される構造単位を有する熱架橋剤を含む、請求項8に記載の樹脂組成物。
- 前記(E)酸化防止剤が、一般式(6)で表される化合物を含有する、請求項1~9のいずれかに記載の樹脂組成物。
- 請求項1~10のいずれかに記載の樹脂組成物から形成された樹脂シート。 A resin sheet formed from the resin composition according to any one of claims 1 to 10.
- 請求項1~10のいずれかに記載の樹脂組成物を硬化した硬化膜。 A cured film obtained by curing the resin composition according to any one of claims 1 to 10.
- 請求項11に記載の樹脂シートを硬化した硬化膜。 A cured film obtained by curing the resin sheet according to claim 11.
- ベンゾオキサゾール前駆体構造がポリベンゾオキサゾールに閉環している割合が30%以上である、請求項12または13に記載の硬化膜。 The cured film according to claim 12 or 13, wherein the ratio of the benzoxazole precursor structure ring-closed to the polybenzoxazole is 30% or more.
- 請求項1~10のいずれかに記載の樹脂組成物を基板上に塗布し、または請求項11に記載の樹脂シートを基材上にラミネートし、乾燥して樹脂膜を形成する工程、
乾燥した樹脂膜を露光する露光工程、露光した樹脂膜を現像する現像工程、
および現像した樹脂膜を加熱処理する加熱処理工程を含むことを特徴とする硬化膜の製造方法。 Applying the resin composition according to any one of claims 1 to 10 on a substrate, or laminating the resin sheet according to claim 11 on a substrate and drying to form a resin film;
An exposure step of exposing the dried resin film, a development step of developing the exposed resin film,
And a method for producing a cured film, comprising a heat treatment step of heat-treating the developed resin film. - 前記現像した樹脂膜を加熱処理する加熱処理工程が、140℃以上220℃以下で加熱処理する工程を含む、請求項15に記載の硬化膜の製造方法。 The manufacturing method of the cured film of Claim 15 in which the heat processing process which heat-processes the said developed resin film includes the process of heat-processing at 140 degreeC or more and 220 degrees C or less.
- 請求項12~14のいずれかに記載の硬化膜が配置された、層間絶縁膜または半導体保護膜。 An interlayer insulating film or a semiconductor protective film on which the cured film according to any one of claims 12 to 14 is disposed.
- 請求項12~14のいずれかに記載の硬化膜が再配線の間の層間絶縁膜として配置された、半導体電子部品または半導体装置。 15. A semiconductor electronic component or a semiconductor device, wherein the cured film according to claim 12 is disposed as an interlayer insulating film between rewirings.
- 前記再配線と層間絶縁膜が2~10層繰り返し配置された、請求項18に記載の半導体電子部品または半導体装置。 The semiconductor electronic component or semiconductor device according to claim 18, wherein the rewiring and the interlayer insulating film are repeatedly arranged in 2 to 10 layers.
- 請求項12~14のいずれかに記載の硬化膜が2種以上の材料で構成される隣接する基板の層間絶縁膜として配置された、半導体電子部品または半導体装置。 A semiconductor electronic component or a semiconductor device, wherein the cured film according to any one of claims 12 to 14 is disposed as an interlayer insulating film of an adjacent substrate made of two or more materials.
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