CN116661243A - Photosensitive polyimide composition, cured product, and electronic component - Google Patents
Photosensitive polyimide composition, cured product, and electronic component Download PDFInfo
- Publication number
- CN116661243A CN116661243A CN202310403043.3A CN202310403043A CN116661243A CN 116661243 A CN116661243 A CN 116661243A CN 202310403043 A CN202310403043 A CN 202310403043A CN 116661243 A CN116661243 A CN 116661243A
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- China
- Prior art keywords
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- component
- photosensitive polyimide
- parts
- polyimide composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 239000004642 Polyimide Substances 0.000 title claims abstract description 58
- 125000000962 organic group Chemical group 0.000 claims abstract description 33
- 229920000642 polymer Polymers 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 6
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 5
- -1 quinone diazide compound Chemical class 0.000 claims description 38
- 239000000758 substrate Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000012670 alkaline solution Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000001174 sulfone group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000011229 interlayer Substances 0.000 claims description 5
- 230000001681 protective effect Effects 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 17
- 239000000126 substance Substances 0.000 abstract description 12
- 230000035945 sensitivity Effects 0.000 abstract description 10
- 239000003989 dielectric material Substances 0.000 abstract description 2
- 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 27
- 238000010438 heat treatment Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000032050 esterification Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 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 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000011161 development Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001408 amides Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- 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 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000010954 inorganic particle Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000003405 preventing effect Effects 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000010076 replication Effects 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- KZLDGFZCFRXUIB-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)phenol Chemical group C1=C(O)C(N)=CC(C=2C=C(N)C(O)=CC=2)=C1 KZLDGFZCFRXUIB-UHFFFAOYSA-N 0.000 description 1
- KECOIASOKMSRFT-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)C=2C=C(N)C(O)=CC=2)=C1 KECOIASOKMSRFT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UHIDYCYNRPVZCK-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C)(C)C1=CC=C(O)C(N)=C1 UHIDYCYNRPVZCK-UHFFFAOYSA-N 0.000 description 1
- KHAFBBNQUOEYHB-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(O)=C1 KHAFBBNQUOEYHB-UHFFFAOYSA-N 0.000 description 1
- JDFAWEKPFLGRAK-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(N)C(O)=CC=1C(C)(C)C1=CC=C(N)C(O)=C1 JDFAWEKPFLGRAK-UHFFFAOYSA-N 0.000 description 1
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 1
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 1
- PMJIKKNFJBDSHO-UHFFFAOYSA-N 3-[3-aminopropyl(diethoxy)silyl]oxy-3-methylpentane-1,5-diol Chemical compound NCCC[Si](OCC)(OCC)OC(C)(CCO)CCO PMJIKKNFJBDSHO-UHFFFAOYSA-N 0.000 description 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- NMGBFVPQUCLJGM-UHFFFAOYSA-N 3-ethylphthalic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1C(O)=O NMGBFVPQUCLJGM-UHFFFAOYSA-N 0.000 description 1
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 description 1
- MUBMBUGIVIAHII-UHFFFAOYSA-N 3-propylphthalic acid Chemical compound CCCC1=CC=CC(C(O)=O)=C1C(O)=O MUBMBUGIVIAHII-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RGVHBPPWCQVMDR-UHFFFAOYSA-N 4-(9h-fluoren-1-yl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C21 RGVHBPPWCQVMDR-UHFFFAOYSA-N 0.000 description 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 1
- SGPJBCCVSFQQED-UHFFFAOYSA-N 4-[(4-aminophenyl)-[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-methylsilyl]oxysilylaniline Chemical compound C=1C=C(N)C=CC=1[Si](C)(O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C)O[SiH2]C1=CC=C(N)C=C1 SGPJBCCVSFQQED-UHFFFAOYSA-N 0.000 description 1
- FNJFWOJEIGPYAS-UHFFFAOYSA-N 4-[4-(9h-fluoren-1-yl)phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C=2C3=C(C4=CC=CC=C4C3)C=CC=2)C=C1 FNJFWOJEIGPYAS-UHFFFAOYSA-N 0.000 description 1
- LVRNKEBRXQHJIN-UHFFFAOYSA-N 4-ethylphthalic acid Chemical compound CCC1=CC=C(C(O)=O)C(C(O)=O)=C1 LVRNKEBRXQHJIN-UHFFFAOYSA-N 0.000 description 1
- PRKPGWQEKNEVEU-UHFFFAOYSA-N 4-methyl-n-(3-triethoxysilylpropyl)pentan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)CC(C)C PRKPGWQEKNEVEU-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- AQVOMFPTJXMAQE-UHFFFAOYSA-N 4-propylphthalic acid Chemical compound CCCC1=CC=C(C(O)=O)C(C(O)=O)=C1 AQVOMFPTJXMAQE-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MVUXVDIFQSGECB-UHFFFAOYSA-N ethyl n-(3-triethoxysilylpropyl)carbamate Chemical compound CCOC(=O)NCCC[Si](OCC)(OCC)OCC MVUXVDIFQSGECB-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011416 infrared curing Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 210000003126 m-cell Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000011415 microwave curing Methods 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-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
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-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
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The present invention relates to the technical field of photosensitive dielectric materials, and in particular, to a photosensitive polyimide composition, a cured product and an electronic component. The photosensitive polyimide composition contains the following component (a) a block polymer soluble in an alkaline aqueous solution; selected from the compounds shown in the following structural formulaWherein R is selected from one of unsubstituted alkyl groups, ar 1 Selected from 4-valent organic groups, ar 2 Selected from 2-valent organic groups, ar 3 Selected from 4-valent organic groups; k+m=5 to 200, m/k=0.01 to 0.5; (b) a photosensitizer; (c) a thermal crosslinking agent; component (c) comprisesCrosslinking agent containing epoxy group in component (C1) and CH in component (C2) 2 A crosslinking agent for OR; (d) a silane coupling agent. The photosensitive polyimide composition has excellent sensitivity, resolution and capability of forming a reproducible fine pattern, and has low warp stress after curing, high chemical stability and adhesion.
Description
Technical Field
The present invention relates to the technical field of photosensitive dielectric materials, and in particular, to a photosensitive polyimide composition, a cured product and an electronic component.
Background
Development of photosensitive polyimide has been carried out using an organic solvent such as N-methylpyrrolidone. However, in recent years, development with an alkaline aqueous solution is considered to be less problematic due to environmental awareness and in view of treatment of waste liquid, but these photosensitive polyimide materials are poor in solubility and difficult to form patterns. In order to solve the above problems, a positive photosensitive polyimide material that can be used for development with an alkaline aqueous solution can be used, and specific methods include a method of introducing a 2-nitrobenzyl group through an ester bond in a polyimide precursor, a method of mixing diazonaphthoquinone with a soluble dihydroxyimide or polybenzoxazole precursor, and the like. However, the positive photosensitive polyimide composition has high warp stress and low sensitivity after curing at high temperature, and thus cannot be widely used.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide a photosensitive polyimide composition, a cured product and an electronic component. The photosensitive polyimide composition provided by the embodiment of the invention has excellent sensitivity, resolution and capability of forming a duplicated fine pattern, and has low warping stress after curing, high chemical stability and cohesiveness.
The invention is realized in the following way:
in a first aspect, the present invention provides a photosensitive polyimide composition comprising the following components (a), (b), (c) and (d):
(a) Block polymers soluble in aqueous alkaline solutions; selected from the group consisting of compounds represented by the following formula 1
Wherein R is selected from one of unsubstituted alkyl groups, ar 1 Selected from 4-valent organic groups, ar 2 Selected from 2-valent organic groups, ar 3 Selected from 4-valent organic groups; k+m=5 to 200, m/k=0.01 to 0.5;
(b) A photosensitizer;
(c) A thermal crosslinking agent; component (C) comprises a crosslinking agent containing an epoxy group as component (C1) and CH as component (C2) 2 A crosslinking agent for OR;
(d) A silane coupling agent.
In a second aspect, the present invention provides a method for producing a pattern, comprising the steps of applying the photosensitive polyimide composition according to any one of the above embodiments to a support substrate, and drying, exposing, developing, and heating the composition;
preferably, the light source used in the exposure step is i-rays.
In a third aspect, the present invention provides a cured product formed by curing the photosensitive polyimide composition according to any one of the foregoing embodiments;
preferably, the cured product includes a surface protective film or an interlayer insulating film.
In a fourth aspect, the present invention provides an electronic component having the cured product according to the foregoing embodiment.
The invention has the following beneficial effects: the photosensitive polyimide composition provided by the embodiment of the invention has the advantages that the part exposed to ultraviolet light is easy to dissolve in alkaline aqueous solution, and the part not exposed to ultraviolet light is insoluble in alkaline aqueous solution, so that fine patterns can be effectively duplicated. The photosensitive polyimide composition has the advantages of excellent sensitivity, high resolution, low warping stress after high-temperature curing, high cohesiveness and good chemical resistance.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the embodiments will be briefly described below, it being understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and other related drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic diagram of a semiconductor package structure according to an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The embodiment of the invention provides a photosensitive polyimide composition, which comprises the following components:
(a) Block polymers soluble in aqueous alkaline solutions; (b) a photosensitizer; (c) a thermal crosslinking agent; (d) a silane coupling agent.
The portion of the photosensitive polyimide composition exposed to ultraviolet light is easily soluble in an aqueous alkaline solution, while the portion not exposed to ultraviolet light is insoluble in an aqueous alkaline solution, thus enabling efficient replication of fine patterns. The photosensitive polyimide composition of the present invention has excellent sensitivity and resolution by increasing the dissolution rate ratio (dissolution contrast) of the exposed portion of the pattern and the unexposed portion with respect to the alkaline developer. Meanwhile, the photosensitive polyimide composition has low warping stress after high-temperature curing and excellent chemical resistance and cohesiveness.
First, the following description will be made on one criterion that component (a) is soluble in an alkaline aqueous solution. A photosensitive composition obtained by dissolving the component (a) alone or together with other components in any solvent is spin-coated on a substrate such as a silicon wafer to form a coating film having a film thickness of about 5 μm, and the coating film is immersed in an aqueous tetramethylammonium hydroxide solution at 20 to 25 ℃ to form a uniform solution.
The alkaline aqueous solution refers to an aqueous tetramethylammonium hydroxide solution, an aqueous metal hydroxide solution, an aqueous organic ammonia solution, or the like.
In the block polymer soluble in an alkaline aqueous solution as the component (a), the main chain skeleton thereof is preferably a polyimide-based or polyoxazole-based polymer, and particularly preferably an alternating block polymer of two types of polymers, from the viewpoints of processability and heat resistance.
From the viewpoint of solubility in an aqueous alkaline solution, the component (a) is preferably a polymer having a plurality of phenolic hydroxyl groups, a plurality of carboxyl groups, or both groups.
Further, the component (a) is more preferably a block copolymer of polyamide ester-polyhydroxyamide, and a polymer having a structural unit represented by the following formula 1, which utilizes alkali solubility of a phenolic hydroxyl group and a part of carboxyl group, good photosensitivity and film characteristics:
wherein R is selected from one of unsubstituted alkyl groups, ar 1 Selected from 4-valent organic groups, ar 2 Selected from 2-valent organic groups, ar 3 Selected from 4-valent organic groups; k+m=5 to 200, for example, 5, 10, 15, 20, 25, 35, 40, 50, 70, 75, 80, 85, 95, 100, 110, 120, 135, 150, 160, 175, 180, 185, 190, 195, 200, and the like, and any number between 5 and 200. m/k=0.01 to 0.5; for example, any number between 0 and 0.5, such as 0.01, 0.05, 0.1, 0.15, 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, and 0.5.
The amide structure containing a hydroxyl group shown in formula 1 can be finally converted into an oxazol body by curing dehydration ring closure, and the amide ester structure can be converted into an imide by curing dealcoholization ring closure, whereby the cured film has excellent chemical resistance and low warp stress.
Further, ar 1 And is selected from any one of the 4-valent organic groups represented by the following formula 2, identically or differently at each occurrence:
wherein R is 1 -R 8 Are monovalent organic groups, and X is a divalent group.
Specifically, R 1 -R 8 Each independently selected from any one of hydrogen, halogen, C1-C5 substituted or unsubstituted alkyl; preferably, R 1 -R 8 Each independently selected from any one of hydrogen, fluorine atom, methyl group and trifluoromethyl group.
X is selected from any one of oxygen atom, C1-C5 substituted or unsubstituted alkylene, sulfur atom, sulfonyl and carbonyl, and X is selected from oxygen atom, methylene, sulfur atom, sulfonyl, carbonyl and C (CH) 3 ) 2 And C (CF) 3 ) 2 Any one of the following.
Specifically, in formula 1, ar 1 The residue derived from tetracarboxylic dianhydride or derivative thereof, which is generally an amide ester structure of tetracarboxylic dianhydride or derivative thereof and diamine, is preferably a 4-valent aromatic group, and preferably tetracarboxylic dianhydride or derivative residue thereof having the structure wherein all of 4 binding sites are present on the aromatic ring, and examples of such tetracarboxylic dianhydride include: pyromellitic dianhydride, 3',4' -biphenyl tetracarboxylic dianhydride, 2, 3',4' -biphenyl tetracarboxylic dianhydride, 2',3,3' -biphenyl tetracarboxylic dianhydride, 3',4' -benzophenone tetracarboxylic dianhydride, 2',3,3' -benzophenone tetracarboxylic dianhydride, 2-bis (3, 4-dicarboxyphenyl) propane dianhydride, 2-bis (2, 3-dicarboxyphenyl) propane dianhydride, 1-bis (3, 4-dicarboxyphenyl) ethane dianhydride, 1-bis (2, 3-dicarboxyphenyl) ethane dianhydride, bis (3, 4-dicarboxyphenyl) methane dianhydride, bis (2, 3-dicarboxyphenyl) methane dianhydride, bis (3, 4-dicarboxyphenyl) sulfone dianhydride, bis (3, 4-dicarboxyphenyl) ether dianhydride, 1,2,5, 6-naphthalene tetrahydrideAromatic tetracarboxylic acid dianhydrides such as formic acid dianhydride, 9-bis (3, 4-dicarboxyphenyl) fluorene dianhydride, 9-bis {4- (3, 4-dicarboxyphenoxy) phenyl } fluorene dianhydride, 2,3,6, 7-naphthalene tetracarboxylic acid dianhydride, 2,3,5, 6-pyridine tetracarboxylic acid dianhydride, 3,4,9, 10-perylene tetracarboxylic acid dianhydride, 2-bis (3, 4-dicarboxyphenyl) hexafluoropropane dianhydride, and aliphatic tetracarboxylic acid dianhydride such as butane tetracarboxylic acid dianhydride and 1,2,3, 4-cyclopentane tetracarboxylic acid dianhydride. These may be used alone or in combination of two or more.
Further, ar 2 And is selected from any one of the 2-valent organic groups represented by formula 3, identically or differently at each occurrence:
wherein R is 9 -R 20 Are monovalent organic groups, and Y is a divalent group;
specifically, R 9 -R 20 Each independently selected from any one of hydrogen, halogen, C1-C5 substituted or unsubstituted alkyl; preferably, R 9 -R 20 Each independently selected from any one of hydrogen, fluorine atom, methyl group and trifluoromethyl group.
Y is selected from any one of oxygen atom, C1-C5 substituted or unsubstituted alkylene, sulfur atom, sulfonyl and carbonyl; y is selected from oxygen atom, methylene, sulfur atom, sulfonyl, carbonyl, C (CH) 3 ) 2 And C (CF) 3 ) 2 Any one of the following.
Further, in formula 1, ar 2 The amino acid residue derived from an amino acid, which is an amide structure formed by an amino acid and a diamine, is generally a 2-valent organic group, and is preferably a 2-valent aromatic group, and amino acid residues having a structure in which 2 binding sites are present on an aromatic ring are preferable, and examples of such amino acids include p-aminobenzoic acid, m-aminobenzoic acid, and o-aminobenzoic acid. One kind of them may be used alone, or two or more kinds may be combined.
Further, ar 3 Each occurrence is identically or differently selected from the 4-valent values represented by formula 4Any one of the groups:
wherein R is 21 -R 26 Are monovalent organic groups, and Q is a divalent group;
preferably, R 21 -R 26 Each independently selected from any one of hydrogen, halogen, C1-C5 substituted or unsubstituted alkyl; preferably, R 21 -R 26 Each independently selected from any one of hydrogen, fluorine atom, methyl group and trifluoromethyl group.
Q is selected from any one of oxygen atom, C1-C5 substituted or unsubstituted alkylene, sulfur atom, sulfonyl and carbonyl; q is selected from oxygen atom, methylene, sulfur atom, sulfonyl, carbonyl, C (CH) 3 ) 2 And C (CF) 3 ) 2 Any one of the following.
Specifically, in formula 1, ar 3 The 4-valent organic group is generally a residue derived from a dihydroxydiamine having an amide structure formed by reacting a hydroxyl-containing diamine with an amino acid, and is preferably a 4-valent aromatic group, and the carbon number of the residue is preferably 6 to 40, more preferably a 6 to 40-valent aromatic group. The above-mentioned 4-valent aromatic group is preferably a residue of a diamine having a structure in which 4 binding sites are all on an aromatic ring and 2 hydroxyl groups are each located at an ortho position to the bond with W. As the diamine compound(s) such as these, examples thereof include 3,3 '-diamino-4, 4' -dihydroxybiphenyl, 4 '-diamino-3, 3' -dihydroxybiphenyl, bis (3-amino-4-hydroxyphenyl) propane, bis (4-amino-3-hydroxyphenyl) propane, and bis (3-amino-4-hydroxyphenyl) sulfone, bis (4-amino-3-hydroxyphenyl) sulfone bis (3-amino-4-hydroxyphenyl) 1, 3-hexafluoropropane, bis (4-amino-3-hydroxyphenyl) 1, 3-hexafluoropropane, and the like. The residue of such diamine is not limited to these, and the residue of these compounds may be two or more kinds alone or in combination.
In addition, ar is not required to deteriorate heat resistance in order to improve adhesion to a substrate 3 Part of the composition may be selected to have a siloxane structureAliphatic group copolymerization, preferably 1 to 10 mol% of bis (3-aminopropyl) tetramethyldisiloxane, bis (p-aminophenyl) octamethylpentasiloxane, and the like.
The terminal group of the aromatic polyamide represented by formula 1 is according to Ar 1 、Ar 2 And Ar is a group 3 The ratio of (2) is carboxylic acid or amine. One or two kinds of blocking agents may be reacted with the polymer terminals as needed to make one terminal or both terminals each be a saturated aliphatic group, an unsaturated aliphatic group, a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group, a mercapto group, or the like. In this case, the end capping rate is preferably 30 to 100%.
It should be noted that: (1) R is as described above 1 -R 26 The halogen mentioned in (b) is not limited to F, but may be bromine, chlorine, or the like.
(2) R is as described above 1 -R 26 The C1-C5 substituted or unsubstituted alkyl group mentioned in (1) may be a C1-C3 substituted or unsubstituted alkyl group, and may be, for example, an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, an n-butyl group, an isopropyl group, an isobutyl group, a tert-butyl group, or the like, or a substituted alkyl group such as a trifluoromethyl group, a trifluoroethyl group, a difluoromethyl group, a trichloromethyl group, or the like.
(3) R is as described above 1 -R 26 The C1-C5 substituted or unsubstituted alkylene group mentioned in (a) may be a C1-C3 unsubstituted alkylene group such as methylene, ethylene, propylene or the like, or a C1-C3 substituted alkylene group such as halogen (fluorine, bromine, chlorine) substituted methylene, halogen substituted ethylene or the like.
The solubility of the polymer in an alkaline aqueous solution is derived from a phenolic hydroxyl group and a carboxyl group, and therefore, it is preferable to contain a structure in a proportion of or above. More preferably: m is an amide unit containing a carboxyl group, and the molar ratio of m to k is m=1 to 33 mol%, and k=67 to 99 mol%. Too large an m-cell can result in a loss of film thickness in the exposed area, resulting in an inefficient replication of the pattern. Therefore, by adjusting the amounts of the alkali-soluble groups of the phenolic hydroxyl groups and the carboxyl groups, the dissolution rate of the polymer in the alkali aqueous solution is changed, and thus a photosensitive polyimide composition having an appropriate dissolution rate can be obtained.
Further, the polymer m+k is the number of repeating structural units of the component (a), and the value of m+k is 5 to 200. When m+k is less than 5, the viscosity of the composition is too small, resulting in the composition not being used as a thick film, and when m+k is greater than 200, the composition becomes insoluble in an alkaline aqueous solution.
When the structures represented by formula 1 each contain 10% by weight or more of fluorine atoms, water repellency to a proper extent is exhibited at the interface of the film during development with an alkaline aqueous solution, preventing permeation at the interface. However, when the fluorine atom content exceeds 20% by weight, the solubility in an aqueous alkaline solution is reduced. The fluorine atom content is therefore preferably 10 to 20% by weight.
The molecular weight of the component (a) is preferably 3000 to 200000, more preferably 5000 to 100000 in terms of weight average molecular weight. The molecular weight herein is a value measured by gel permeation chromatography and converted from a standard polystyrene standard curve.
In the embodiment of the invention, the block polymer with the structural unit shown in the formula 1 is generally obtained by preparing a diacid chloride compound by esterifying dianhydride and alcohol and then acylating and chloridizing, condensing hydroxyl diamine and dianhydride into an oligomer, and polymerizing the oligomer with the prepared diacid chloride compound.
Specifically, in the first step, a diacid diester can be prepared by reacting an alcohol with a dianhydride, and then preparing a diacid chloride diester by acid chlorination. And secondly, carrying out polycondensation reaction on a diamine compound containing hydroxyl and dianhydride to prepare the amino-terminated polyhydroxyamide oligomer. And thirdly, preparing the block polymer by condensation reaction of the diacyl chloride diester prepared in the first step and the amino-terminated polyhydroxyamide.
In the present invention, as the quinone diazide compound of the component (b), a diazidonaphthoquinone-5-sulfonyl group, a diazidonaphthoquinone-4-sulfonyl group, or the like can be preferably used. In the present invention, a diazidonaphthoquinone sulfonyl ester compound in which a diazidonaphthoquinone-5-sulfonyl group and a diazidonaphthoquinone-4-sulfonyl group are used together in the same molecule may be obtained, or a mixture of a diazidonaphthoquinone-5-sulfonyl ester compound and a diazidonaphthoquinone-4-sulfonyl ester compound may be used.
Wherein (b) the quinone diazide compound more preferably comprises an ester formed from a phenol compound and a diazide naphthoquinone-5-sulfonyl group. Thus, high sensitivity can be obtained under i-line exposure.
The content of the quinone diazide compound (b) is preferably 5 to 20 parts, more preferably 8 to 15 parts, for example, 5 to 20 parts, 8 parts, 10 parts, 12 parts, 15 parts, 16 parts, 18 parts, 20 parts, or the like, based on 100 parts by weight of the polyimide as the component (a). By setting the content of the quinone diazide compound to the above range, higher sensitivity can be achieved, and further a sensitizer or the like can be added as needed.
The photosensitive polyimide composition according to the embodiment of the present invention may contain (c) a thermal crosslinking agent for the purpose of easily obtaining a cured film. As component (c 1), a crosslinking agent having an epoxy group, and as component (c 2), a crosslinking agent having-CH 2 A crosslinking agent having an OR (R is a hydrogen atom OR a 1-valent organic group) group, which is crosslinked by reacting with the polymer as the component (a) in the heat treatment step after the photosensitive polymer composition of the present invention is applied, exposed and developed, OR which is a compound which is self-polymerized in the heat treatment step. In addition, the crosslinking agent as the component (c 2) has affinity for the alkaline aqueous solution, and can increase the dissolution rate of the alkaline aqueous solution.
In the present invention, component (c 1) is a crosslinking agent having an epoxy group in its structure. Wherein component (c 1) is selected from the group consisting of compounds represented by the following formula 5-1,
specific examples of the compound represented by the following formula 5-1 include, for example, epiclon (registered trademark) 850-S, epiclon HP-4032, epiclon HP-7200, epiclon HP-820, epiclon HP-4700, epiclon EXA-4710, epiclon HP-4770, epiclon EXA-859CRP, epiclon EXA-4810, epiclon EXA-4850, epiclon EXA-4816, epiclon EXA-4822 (above, trade name, dainippon Ink and Chemicals, manufactured by Inc.), rikaresin (registered trademark) BPO-20E, rikaresin BEO-60E (above, trade name, manufactured by New Japanese chemical Co., ltd.), EP-4003S, EP-4000S (above, trade name, manufactured by ADEKA) and the like. They may be used alone or in combination of 2 or more. In addition, two or more of these compounds may be used singly or in combination.
In the present invention, component (c 2) is a compound having a structure of-CH 2 OR (R is a hydrogen atom OR a 1-valent organic group). The number of the groups in the compound may be one or more, but is preferably two or more. Wherein component (c 2) is selected from the compounds represented by the following formula 5-2.
In formula 5-2, R 29 Selected from hydrogen atoms or monovalent organic radicals, R 30 Selected from monovalent organic groups, n is an integer from 1 to 4, and X is selected from single bonds or organic groups of 1 to 4 valences. a is an integer of 1 to 4, b is an integer of 0 to 3, when a is 2,3 or 4, R 29 Identical or different, R when b is 2 or 3 30 The same or different.
The following formula 5-2-1 represents a specific example of the compound represented by formula 5-2, and these compounds may be used singly or in combination.
Examples of the 1-4 valent organic group of X in the formula 5-2 include an alkyl group having 1 to 10 carbon atoms, an alkylene group having 2 to 10 carbon atoms (e.g., ethylene group, etc.), an arylene group having 6 to 30 carbon atoms (e.g., phenylene group, etc.), or a group obtained by substituting some or all of these hydroxyl hydrogen atoms with halogen atoms such as fluorine atoms, and these groups may further contain phenyl groups, sulfone groups, carbonyl groups, ether linkages, thioether linkages, amide linkages, etc. R is R 29 Preferably hydrogen, alkyl or alkenyl. The number of carbon atoms of the alkyl group or alkenyl group is preferably 1 to 20.R is R 30 Preferably alkyl, alkenyl, alkoxyalkyl or hydroxymethyl, and the number of carbon atoms is preferably 1 to 20.
The purity of the compound represented by the above formula 5-2 is preferably 75% or more, more preferably 85% or more. When the purity is 85% or more, the storage stability is excellent, and the crosslinking reaction of the polyimide composition can be sufficiently performed. Further, since unreacted groups which become water-absorbent groups can be reduced, the water absorption of the polyimide composition can be reduced. Examples of the method for obtaining the high-purity thermal crosslinking agent include recrystallization and distillation. The purity of the thermal crosslinking agent can be determined by liquid chromatography.
The content of the thermal crosslinking agent in the component (c) is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, based on 100 parts by mass of the polyimide in the component (a). When the amount is 5 parts by weight or more, the crosslinking density of the cured film is increased, the chemical resistance is high, and the cured film has low curing warpage properties, and when it is 10 parts by weight or more, the chemical resistance is higher, the low curing warpage properties are better, and at the same time, higher mechanical properties can be obtained. In addition, from the viewpoint of the storage stability and mechanical strength of the composition, it is preferably 30 parts by mass or less.
Further, the content of c1 is any value between 5 and 15 parts by weight, for example, 5 parts, 6 parts, 7 parts, 8 parts, 9 parts, 10 parts, 11 parts, 12 parts, 13 parts, 14 parts, 15 parts, etc.; the content of c2 is any value between 0.1 and 15 parts, for example, 0.1 part, 0.5 part, 1 part, 2 parts, 5 parts, 7 parts, 8 parts, 10 parts, 13 parts, 14 parts, 15 parts, etc., and 0.1 to 15 parts.
The polyimide composition of the present invention further contains (d) a silane coupling agent, typically an organosilane compound, and examples of the organosilane compound include: gamma-aminopropyl trimethoxysilane, gamma-aminopropyl triethoxysilane, vinyl trimethoxysilane, gamma-glycidoxypropyl triethoxysilane, gamma-glycidoxypropyl trimethoxysilane, gamma-methacryloxypropyl trimethoxysilane, gamma-acryloxypropyl trimethoxysilane, gamma-ureidopropyl triethoxysilane, 3-mercaptopropyl trimethoxysilane, 3-isocyanatopropyl triethoxysilane, bis (2-hydroxyethyl) -3-aminopropyl triethoxysilane, triethoxysilylpropyl ethyl carbamate, 3- (triethoxysilyl) propylsuccinic anhydride, phenyltriethoxysilane, phenyltrimethoxysilane, N-phenyl-3-aminopropyl trimethoxysilane, 3-triethoxysilyl-N- (l, 3-dimethylbutylidene) propylamine, 2- (3, 4-epoxycyclohexyl) ethyl trimethoxysilane, and the like.
When the organic silane compound is contained, the adhesion of the photosensitive polyimide composition to the substrate after curing can be improved. When the organosilane compound is contained, the content of the organosilane compound is more preferably 0.5 to 15 parts by mass, still more preferably 0.5 to 10 parts by mass, based on 100 parts by mass of the component (a). For example, 0.5 to 15 parts such as 0.5 parts, 1 part, 2 parts, 3 parts, 4 parts, 5 parts, 6 parts, 7 parts, 8 parts, 9 parts, 1 part, 11 parts, 12 parts, 13 parts, 14 parts, and 15 parts.
The polyimide composition of the present invention further contains (e) a solvent, preferably an organic solvent. For example, ketones, esters, lactones, ethers, halogenated hydrocarbons, hydrocarbons and the like can be used. Specific examples thereof include: polar solvents such as gamma-butyrolactone, N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N-dimethylacetamide, N-dimethylsulfoxide, hexamethylphosphoric triamide, dimethylimidazolidinone, tetraethylurea, tetramethylurea, ethyl lactate, 3-methoxy-N, N-dimethylpropaneamide, and N-acetyl-epsilon-caprolactam. It is also possible to use: acetone, diethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl acetate, ethyl acetate, butyl acetate, diethyl oxalate, diethyl malonate, diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran, methylene chloride, 1, 2-dichloroethane, 1, 4-dichlorobutane, trichloroethane, chlorobenzene, o-dichlorobenzene, hexane, heptane, octane, benzene, toluene, xylene, 1-methoxy-2-propanol, 1-methoxy-2-acetoxypropane, propylene glycol 1-monomethyl ether 2-acetate, and the like. The component (e) may be used alone or in combination of two or more.
When component (e) is contained, the blending amount of component (e) is preferably 50 to 1000 parts by mass, more preferably 100 to 200 parts by mass, per 100 parts by mass of component (a). For example, 50 parts, 60 parts, 70 parts, 100 parts, 150 parts, 200 parts, 300 parts, 400 parts, 500 parts, 600 parts, 700 parts, 800 parts, 900 parts and 1000 parts of any number between 50 and 1000 parts of the peak.
The invention may further comprise (f) a leveling agent, which may be a surfactant, thereby improving the coatability with the substrate. Examples of the surfactant include fluorine-based surfactants such as fluoroad (trade name, manufactured by Sumitomo 3M (Co., ltd.), megafac (trade name, manufactured by DIC (Co., ltd.), surflon (trade name, manufactured by Asahi Kabushiki Kaisha); organosiloxane surfactants such as KP341 (trade name, manufactured by Xinyue chemical industry Co., ltd.), DBE (trade name, manufactured by Chisso Corporation), polyflow, glanol (trade name, manufactured by Kagaku chemical Co., ltd.), BYK (trade name, manufactured by BYK-Chemie GmbH);
and acrylic polymer surfactants such as Polyflow (trade name, manufactured by Kyowa Kagaku Co., ltd.).
Next, a method for producing the photosensitive polyimide composition according to the embodiment of the present invention will be described. For example, the photosensitive polyimide composition can be obtained by uniformly mixing the above-mentioned components (a) to (d) and, if necessary, the components (e) to (f) and the like. The dissolution method includes stirring and heating. When heating is performed, the heating temperature is preferably set within a range that does not deteriorate the performance of the polyimide composition, and is usually room temperature to 80 ℃. The dissolution order of the components is not particularly limited, and includes, for example, a method of sequentially dissolving compounds having low solubility. In addition, as for the components such as the surfactant and a part of the adhesion improver which are liable to generate bubbles when dissolved by stirring, it is possible to prevent dissolution failure of other components due to generation of bubbles by adding them last after dissolving other components.
The photosensitive polyimide composition thus obtained is preferably filtered using a filter to remove impurities and particles. The filter pore size is 0.5 to 0.02. Mu.m, for example, but not limited to, 0.5. Mu.m, 0.2. Mu.m, 0.1. Mu.m, 0.05. Mu.m, 0.02. Mu.m, etc. The filter material includes polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE), etc., preferably polyethylene or nylon. When inorganic particles are contained in the photosensitive polyimide composition, a filter having a larger pore diameter than the particle diameter of the inorganic particles is preferably used.
The cured product provided by the embodiment of the invention can be obtained by curing the positive photosensitive polyimide composition. The cured product of the present invention can be used as a patterned cured film or an unpatterned cured film.
The method for producing a pattern cured film includes: a step (film forming step) of forming a photosensitive polyimide film by applying the positive photosensitive polyimide composition on a substrate and drying the composition; a step of exposing the photosensitive polyimide film (exposure step); a step (developing step) of developing the photosensitive polyimide film after exposure with an aqueous alkali solution to form a patterned polyimide film; and a step of heating the patterned polyimide film (heating step). The method for producing the unpatterned cured film includes, for example, the film forming step and the heating step. The method may further comprise an exposure step.
In the film forming step, the positive photosensitive polyimide composition is applied to a metal substrate such as Cu, a glass substrate, a semiconductor, a metal oxide insulator (e.g., tiO) by, for example, dipping, spraying, screen printing, spin coating, or the like 2 、SiO 2 Etc.), silicon nitride, etc. From the viewpoint of operability, the applied positive photosensitive polyimide composition may be dried by heating (for example, 90 to 150 ℃ C. For 1 to 5 minutes) using a hot plate, an oven or the like. The support substrate may be cleaned with acetic acid or the like before coating. The film thickness of the photosensitive polyimide film obtained is preferably 5 to 20. Mu.m.
In the exposure step, for example, the photosensitive polyimide film formed on the substrate is irradiated with the active light beam through a mask. From the viewpoint of transparency of the component (a), irradiation with i-rays can be suitably used. After exposure, post-exposure heating (PEB) may be performed as needed. The post-exposure heating temperature is preferably 70-140 ℃, and the post-exposure heating time is preferably 1-5 minutes.
In the developing step, for example, the exposed portion of the photosensitive polyimide film after the exposing step is removed with a developing solution, thereby patterning the photosensitive polyimide film. In the case of the alkali-soluble photosensitive polyimide composition, for example, an aqueous alkali solution such as sodium hydroxide, potassium hydroxide, sodium silicate, ammonia, ethylamine, diethylamine, triethylamine, triethanolamine, tetramethylammonium hydroxide (TMAH) or the like can be suitably used as the developer. The alkali concentration of these aqueous solutions is preferably set to 0.1 to 10 mass%. Further, alcohols or surfactants may be added to the developer. These may be blended in a range of preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the developer. The patterned photosensitive polyimide film is referred to as a patterned polyimide film.
In the heating step, the patterned polyimide film or the photosensitive polyimide film is heated to cure the photosensitive polyimide composition. Particularly, a film obtained by curing a patterned polyimide film is called a patterned cured film. The heating temperature is preferably 100 to 500 ℃, preferably 400 ℃ or less, more preferably 375 ℃ or less, and still more preferably 300 to 350 ℃. The heating time is preferably 20 minutes to 6 hours, more preferably 30 minutes to 3 hours. Multi-stage heating may also be performed. The heat treatment may be performed using, for example, an oven such as a quartz tube oven, a hot plate, a rapid annealing furnace (rapid thermal anneal), a vertical diffusion furnace, an infrared curing furnace, an electron beam curing furnace, or a microwave curing furnace. In addition, although either the atmosphere or an inert atmosphere such as nitrogen may be selected, the inert atmosphere such as nitrogen is preferable because oxidation of the pattern can be prevented when the pattern is performed under nitrogen.
The cured product of the present invention can be used as an interlayer insulating film, a surface protective film, or the like.
The interlayer insulating film and the surface protective film of the present invention can be used for electronic components and the like, and the electronic components of the present invention can be used for semiconductor devices and the like. The semiconductor device can be used for various electronic equipment and the like, and a schematic view of the semiconductor package structure of the present invention is shown in fig. 1.
This gives excellent rust preventing effect and adhesion effect to the support substrate (particularly copper substrate and copper alloy substrate), and can suppress discoloration of the cured film and the support substrate (particularly copper substrate and copper alloy substrate).
Examples of the semiconductor device include a semiconductor package such as a Wafer Level Chip Size Package (WLCSP) and a fan-out wafer level package (FOWLP). The interlayer insulating film and the surface protective film of the present invention can be used for a circuit-forming substrate which can be used for a suspension for a hard disk drive, a flexible wiring board, or the like.
The features and capabilities of the present invention are described in further detail below in connection with the examples.
Bis-AP-AF:2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane
PNDC: p-nitrobenzoyl chloride
SiDA:1, 3-bis (3-aminopropyl) tetramethyldisiloxane
ODPA:4,4' -Oxyphthalic anhydride
MAP: m-aminophenol
NMP: n-methyl-2-pyrrolidone
GBL; gamma-butyrolactone
TMAH: tetramethyl ammonium hydroxide
SOCl 2 : thionyl chloride
Synthesis example 1
The present embodiment provides a method for producing a diamine containing a hydroxyl group, comprising:
18.3g (0.05 mol) of Bis-AP-AF were dissolved in 100g of acetone under a stream of dry nitrogen, and the resulting solution was subsequently cooled to-10 ℃. Subsequently, 18.56g (0.1 mol) of PNDC in 50g of acetone was added dropwise thereto so that the temperature of the reaction solution did not exceed 0 ℃. After the addition was completed, the reaction mixture was returned to room temperature, and the precipitated white solid was filtered off and dried under vacuum at 50 ℃.
30g of the solid was charged into a 300mL stainless steel autoclave, dispersed in 250mL of a methyl-fiber-melting agent, 2g of 5% palladium on carbon was added thereto, and hydrogen gas was introduced thereto with a balloon, and the reduction reaction was carried out at room temperature. After about 2 hours, it was confirmed that the balloon did not shrink any further, and the reaction was terminated. After the completion of the reaction, the catalyst was removed by filtration, and the resultant was concentrated under reduced pressure to obtain a diamine compound (I), and the obtained solid was directly used for the reaction.
Diamine compound (I)
Synthesis example 2
The embodiment provides a method for synthesizing a polymer A, which comprises the following steps:
under a dry nitrogen flow, 28.08g (0.09 mol) of ODPA, 8.3g (0.18 mol) of ethanol, 14.24g (0.18 mol) of pyridine, 300g of tetrahydrofuran were charged and reacted at 60℃for 8 hours. Then the system was cooled to 0℃and 23.4g (0.198 mol) of SOCl2 was added dropwise, followed by further reaction for 1 hour, and the diacid dichlorides were obtained by evaporation.
54.4g (0.09 mol) of diamine (I) was dissolved in 220g of NMP, to which 3.1g (0.01 mol) of ODPA was added and 12g of NMP were reacted at 20℃for 3 hours. 2.2g (0.02 mol) MAP and 14.24g (0.198 mol) pyridine were then added. Then cooling to-10 ℃, dropping the obtained diacyl chloride diester after evaporation, and continuously reacting for 1 hour at-10 ℃. After the reaction was completed, the solution was poured into 5L of water, and the polymer solid precipitate was collected by filtration. The polymer solid was dried in a vacuum dryer at 80℃for 72 hours to give polymer A. Polymer A was subjected to molecular weight measurement and esterification rate measurement, and had a molecular weight of 21000 and an esterification degree of 90%.
The specific test method is as follows:
(1) Determination of molecular weight
The number average molecular weight was determined under the following conditions by Gel Permeation Chromatography (GPC) based on standard polystyrene conversion. The number average molecular weight of polymer A was 39,000. The measurement was performed using 1mL of a solution with respect to 0.5mg a of the solvent [ Tetrahydrofuran (THF)/Dimethylformamide (DMF) =1/1 (volume ratio) ].
Measurement device: l4000UV manufactured by Hitachi of Detector Co., ltd
And (3) a pump: l6000 manufactured by Hitachi Co., ltd
C-R4A Chromatopac manufactured by Shimadzu corporation
Measurement conditions: chromatographic column Gelpack GL-S300 MDT-5X 2
Eluent: THF/DMF=1/1 (volume ratio), liBr (0.03 mol/L), H 3 PO 4 (0.06 mol/L) flow rate: 1.0mL/min, detector: UV270nm
(2) Determination of esterification Rate
Further, the esterification ratio of a (the reaction esterification ratio of carboxyl groups of ODPA and HEMA was 80 mol% with respect to all carboxyl groups of polyamic acid (the remaining 20 mol% is carboxyl groups) was calculated by NMR measurement under the following conditions.
Measurement device: AV400M manufactured by Bruker Biospin Co
Magnetic field strength: 400MHz
Reference substance: tetramethylsilane (TMS)
Solvent: dimethyl sulfoxide (DMSO)
Synthesis example 3
With respect to Synthesis example 2, the number of moles of the diacid chloride diester was changed to 0.8mol and the number of moles of the ODPA was changed to 0.2mol, to obtain a polymer C having a molecular weight of 22000 and an esterification degree of 80%. m/k=2/8.
Synthesis example 4
With respect to Synthesis example 2, the number of moles of the diacid chloride diester was changed to 0.7mol and the number of moles of the ODPA was changed to 0.3mol, to obtain a polymer D having a molecular weight of 21000 and an esterification degree of 70%. m/k=3/7.
Synthesis example 5
The molar number of the diacid chloride diester was changed to 0.6mol, and the molar number of the odpa was changed to 0.4mol, to obtain a polymer E having a molecular weight of 21000 and an esterification degree of 60%. m/k=4/6.
Synthesis example 6
The mole number of the diacid chloride diester was changed to 1mol, and the mole number of the ODPA was changed to 0mol, to obtain a polymer F having a molecular weight of 22000 and an esterification degree of 100%. m/k=0.
Synthesis example 7
The molar number of the diacid chloride diester was changed to 0mol, the molar number of the ODPA was changed to 1mol, and polymer G having a molecular weight of 20000 and an esterification degree of 0% was obtained.
Examples 1 to 10 and comparative examples 1 to 2
Photosensitive polyimide compositions of examples 1 to 5 and comparative example 1 were prepared according to the components and blending amounts shown in tables 1 to 2. The blending amount in table 1 is the mass parts of each component per 100 mass parts of component (a).
The components used are as follows.
Component (b): photosensitizers
Component (c): thermal crosslinking agent
Component (d): solvent(s)
d1: GBL (gamma-butyrolactone)
d2: EL (ethyl lactate)
Component (e): silane coupling agent
e1: gamma-ureidopropyltriethoxysilane
e2: vinyl triethoxysilane
TABLE 1
TABLE 2
The photosensitive polyimide compositions produced in examples and comparative examples were evaluated for performance by the following methods:
(1) Production of developing film
The photosensitive polyimide compositions (varnishes) produced in examples and comparative examples were spin-coated on 8-inch silicon wafers, and then heat-treated (prebaked) at 120℃for 3 minutes using a hot plate (manufactured by Tokyo Electron Ltd., coating and developing apparatus Mark-7) to produce prebaked films having a thickness of 6. Mu.m. Using an i-line stepper (manufactured by Nikon Corporation, NSR-2005i 9C) at a rate of 50 to 400mJ/cm 2 Exposure of 10mJ/cm 2 The resulting pre-baked film is exposed to light. After exposure, the photosensitive polyimide composition was baked after exposure to 100℃for 1 minute. After the photosensitive polyimide composition was subjected to post-exposure baking, it was developed with a 2.38 wt% aqueous solution of Tetramethylammonium (TMAH) (manufactured by mitsubishi gas chemistry, ELM-D) for 90 seconds, and then rinsed with pure water to obtain a developed film.
(2) Method for measuring film thickness
The film thicknesses after pre-baking and development were measured at refractive indices of 1.63 using a light interference film thickness measuring device LAMBDA ACE STM-602 manufactured by Dainippon Screen mfg.Co., ltd.
(3) Calculation of developing film loss amount
The amount of loss of the developing film was calculated according to the following formula. Since the film thickness after prebaking is 6 μm, the loss amount of the developing film is preferably less than 1 μm. A case where the loss amount of the developing film was less than 1 μm was judged as "A", a case where 1 to 1.5 μm was judged as "B", and a case where 2 μm or more was judged as "C".
Development film loss amount (μm) =film thickness after prebaking-film thickness after development. The results are shown in Table 3.
(4) Measurement of warp
The varnish was applied by spin coating using an application developing device ACT-8, prebaked to a film thickness of 10 μm after 3 minutes of prebaking at 120 ℃ and then heated to 200 ℃ at a rate of 3.5 ℃/min for 1 hour at 200 ℃ using an inert oven under conditions of an oxygen concentration of 20ppm or less. When the temperature was 50℃or lower, the wafer was taken out, and the cured film was measured by using a pressure device FLX2908 (manufactured by KLA Tencor Co.). As a result, the case of 35MPa or more was regarded as insufficient (D), the case of 30MPa or more and less than 35MPa was regarded as good (C), the case of 20MPa or more and less than 30MPa was regarded as better (B), and the case of less than 20MPa was regarded as best (A).
(5) Sensitivity evaluation
After exposure and development, an exposure amount (referred to as an optimal exposure amount Eop) of a line and space pattern (1L/1S) of 20 μm was formed with a width of 1 to 1 as sensitivity. If the Eth is 200mJ/cm 2 Hereinafter, it can be determined as high sensitivity. More preferably 150mJ/cm 2 The following is given. The results are shown in Table 3.
(6) Evaluation of chemical resistance
The cured product was applied by pipette. The coated cured product was placed in a nitrogen oven at 200 ℃ and held for 60 minutes. Thereafter, the solidified material was transferred from the heating plate and cooled to room temperature. The cooled solidified product was washed with a 25% naoh aqueous solution, and dried, and then the film thickness was measured.
The film thickness change rate (%) was calculated from the film thickness change. If the value is positive, this means that the membrane swells, and if the value is negative, this means that the membrane dissolves. The results are shown in Table 3.
(7) Evaluation of adhesion
With the above method for producing a cured product, a cured product was produced on a Cu substrate, and the obtained cured product was cut into 10×10 checkered cuts by a shearing blade using a cross cut guide (manufactured by COAT-TECH corporation), thereby dividing the cured product into 100 pieces.
An adhesive tape (manufactured by 3M japan corporation) was attached to the cured product, and the adhesive tape was peeled off. The adhesiveness was evaluated as follows based on the number of chips of the cured product peeled from the substrate when the adhesive tape was peeled off.
A: the residual lattice is 100 to 80.
B: the remaining lattice is less than 80.
The results are shown in Table 3.
TABLE 3 Table 3
As can be seen from Table 3, the photosensitive polyimide compositions provided in examples 1 to 10 of the present invention each have a small loss amount of the developing film, excellent low warp stress, and excellent chemical resistance. The warp stress of comparative example 1 is higher than that of the example. And the developing film of comparative example 2 has large loss, high warp stress and poor chemical resistance.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A photosensitive polyimide composition comprising the following components (a), (b), (c) and (d):
(a) Block polymers soluble in aqueous alkaline solutions; selected from the group consisting of compounds represented by the following formula 1
Wherein R is selected from one of unsubstituted alkyl groups, ar 1 Selected from 4-valent organic groups, ar 2 Selected from 2-valent organic groups, ar 3 Selected from 4-valent organic groups; k+m=5 to 200, m/k=0.01 to 0.5;
(b) A photosensitizer;
(c) A thermal crosslinking agent; component (C) comprises a crosslinking agent containing an epoxy group as component (C1) and CH as component (C2) 2 A crosslinking agent for OR;
(d) A silane coupling agent.
2. The photosensitive polyimide composition according to claim 1, wherein R is selected from the group consisting of C1-C10 unsubstituted alkyl groups, preferably C1-C5 unsubstituted alkyl groups, more preferably C1-C3 unsubstituted alkyl groups, and most preferably CH 3 、CH 2 CH 3 、CH(CH 3 ) 2 Any one of the following.
3. The photosensitive polyimide composition according to claim 1, wherein Ar 1 And is selected from any one of the 4-valent organic groups represented by formulas 2-1 to 2-9, identically or differently at each occurrence:
wherein R is 1 -R 8 Are monovalent organic groups, X is a divalent group,
preferably, R 1 -R 8 Each independently selected from any one of hydrogen, halogen, C1-C5 substituted or unsubstituted alkyl; preferably, R 1 -R 8 Each independently selected from any one of hydrogen, fluorine atom, methyl group and trifluoromethyl group;
preferably, X is selected from any one of an oxygen atom, a C1-C5 substituted or unsubstituted alkylene group, a sulfur atom, a sulfone group, and a carbonyl group;
preferably, X is selected from the group consisting of an oxygen atom, a methylene group, a sulfur atom, a sulfone group, a carbonyl group, C (CH) 3 ) 2 And C (CF) 3 ) 2 Any one of them;
preferably Ar 2 And is selected from any one of the 2-valent organic groups represented by formulas 3-1 to 3-12, identically or differently at each occurrence:
wherein R is 9 -R 20 Are monovalent organic groups, and Y is a divalent group;
preferably, R 9 -R 20 Each independently selected from any one of hydrogen, halogen, C1-C5 substituted or unsubstituted alkyl; preferably, R 9 -R 20 Each independently selected from any one of hydrogen, fluorine atom, methyl group and trifluoromethyl group;
preferably, Y is selected from any one of an oxygen atom, a C1-C5 substituted or unsubstituted alkylene group, a sulfur atom, a sulfone group, and a carbonyl group;
preferably, Y is selected from the group consisting of an oxygen atom, a methylene group, a sulfur atom, a sulfone group, a carbonyl group, C (CH) 3 ) 2 And C (CF) 3 ) 2 Any one of them;
preferably Ar 3 And is selected from any one of the 4-valent organic groups represented by formulas 4-1 to 4-6, identically or differently at each occurrence:
wherein R is 21 -R 26 Are monovalent organic groups, and Q is a divalent group;
preferably, R 21 -R 26 Each independently selected from any one of hydrogen, halogen, C1-C5 substituted or unsubstituted alkyl; preferably, R 21 -R 26 Each independently selected from any one of hydrogen, fluorine atom, methyl group and trifluoromethyl group;
preferably, Q is selected from any one of an oxygen atom, a C1-C5 substituted or unsubstituted alkylene group, a sulfur atom, a sulfone group, and a carbonyl group;
preferably, Q is selected from the group consisting of an oxygen atom, a methylene group, a sulfur atom, a sulfone group, a carbonyl group, C (CH) 3 ) 2 And C (CF) 3 ) 2 Any one of them;
preferably, the weight average molecular weight of the block polymer is 3000-200000, preferably 5000-100000.
4. The photosensitive polyimide composition according to claim 1, wherein the photosensitizer is a quinone diazide compound.
5. The photosensitive polyimide composition according to claim 1, wherein the component (c) is selected from the group consisting of compounds represented by the formula 5-1 and the formula 5-2,
wherein, in formula 5-1, U is selected from divalent organic groups containing alicyclic or aromatic rings;
in formula 5-2, R 29 Selected from hydrogen atoms or monovalent organic radicals, R 30 Selected from monovalent organic groups, n is an integer from 1 to 4, X is selected from single bonds or organic groups of 1 to 4 valences; a is an integer of 1 to 4, b is an integer of 0 to 3, when a is 2,3 or 4, R 29 Identical or different, R when b is 2 or 3 30 The same or different.
6. The photosensitive polyimide composition according to any one of claims 1 to 5, wherein the component (b) is contained in an amount of 5 to 20 parts by weight, the component (c) is contained in an amount of 5 to 30 parts by weight, the content of c1 is 5 to 15 parts by weight, the content of c2 is 0.1 to 15 parts by weight, and the content of the component (d) is 0.5 to 10 parts by weight, based on 100 parts by weight of the content of the component (a).
7. The photosensitive polyimide composition according to any one of claims 1 to 5, further comprising any one or a combination of at least two of a solvent and a leveling agent;
preferably, the solvent is contained in an amount of 100 to 200 parts by weight and the leveling agent is contained in an amount of 100 to 1000ppm based on 100 parts by weight of the component (a).
8. A method for producing a pattern, comprising the steps of applying the photosensitive polyimide composition according to any one of claims 1 to 7 to a support substrate, and drying, exposing, developing and heat-treating the same;
preferably, the light source used in the exposure step is i-rays.
9. A cured product formed by curing the photosensitive polyimide composition according to any one of claims 1 to 7;
preferably, the cured product includes a surface protective film or an interlayer insulating film.
10. An electronic component, characterized in that the electronic component has the cured product according to claim 9.
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| CN102292675A (en) * | 2009-12-28 | 2011-12-21 | 东丽株式会社 | Positive-type photosensitive resin composition |
| JP2012181273A (en) * | 2011-02-28 | 2012-09-20 | Sumitomo Bakelite Co Ltd | Photosensitive resin composition, cured film, protective film, insulator film, semiconductor device, and display device |
| CN114539524A (en) * | 2022-01-11 | 2022-05-27 | 吉林奥来德光电材料股份有限公司 | Photosensitive resin precursor polymer, photosensitive resin composition paste and use thereof |
| CN115826360A (en) * | 2022-12-23 | 2023-03-21 | 江苏艾森半导体材料股份有限公司 | Photosensitive polyimide composition, method for producing pattern, cured product, and electronic component |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102292675A (en) * | 2009-12-28 | 2011-12-21 | 东丽株式会社 | Positive-type photosensitive resin composition |
| JP2012181273A (en) * | 2011-02-28 | 2012-09-20 | Sumitomo Bakelite Co Ltd | Photosensitive resin composition, cured film, protective film, insulator film, semiconductor device, and display device |
| CN114539524A (en) * | 2022-01-11 | 2022-05-27 | 吉林奥来德光电材料股份有限公司 | Photosensitive resin precursor polymer, photosensitive resin composition paste and use thereof |
| CN115826360A (en) * | 2022-12-23 | 2023-03-21 | 江苏艾森半导体材料股份有限公司 | Photosensitive polyimide composition, method for producing pattern, cured product, and electronic component |
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