CN102782579A - Negative photosensitive resin composition, interlayer insulating film and method of formation of same - Google Patents
Negative photosensitive resin composition, interlayer insulating film and method of formation of same Download PDFInfo
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- CN102782579A CN102782579A CN2011800109403A CN201180010940A CN102782579A CN 102782579 A CN102782579 A CN 102782579A CN 2011800109403 A CN2011800109403 A CN 2011800109403A CN 201180010940 A CN201180010940 A CN 201180010940A CN 102782579 A CN102782579 A CN 102782579A
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- sensitive resin
- resin combination
- negative light
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- 239000011229 interlayer Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 35
- 230000015572 biosynthetic process Effects 0.000 title claims description 17
- 239000011342 resin composition Substances 0.000 title abstract 2
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 229920005672 polyolefin resin Polymers 0.000 claims abstract description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- -1 thiazolinyl carbonyl oxygen Chemical compound 0.000 claims description 76
- 229920005989 resin Polymers 0.000 claims description 58
- 239000011347 resin Substances 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 239000003513 alkali Substances 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 10
- 238000011161 development Methods 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
- 230000003252 repetitive effect Effects 0.000 claims description 3
- 238000005286 illumination Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- 239000005864 Sulphur Chemical group 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000003566 oxetanyl group Chemical group 0.000 abstract 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 abstract 1
- 239000010408 film Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- 238000010438 heat treatment Methods 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229940042596 viscoat Drugs 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 5
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 5
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000007598 dipping method Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000004492 methyl ester group Chemical group 0.000 description 3
- 229940017219 methyl propionate Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- DWSBPCLAELVSFD-UHFFFAOYSA-N (2-fluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1F DWSBPCLAELVSFD-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BBJLVBHQJYDCHY-UHFFFAOYSA-N C(C=C)(=O)O.CC(O)(C(CO)(CO)CO)C Chemical compound C(C=C)(=O)O.CC(O)(C(CO)(CO)CO)C BBJLVBHQJYDCHY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- CQHKDHVZYZUZMJ-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-prop-2-enoyloxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CO)COC(=O)C=C CQHKDHVZYZUZMJ-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- ZCZFEIZSYJAXKS-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COC(=O)C=C ZCZFEIZSYJAXKS-UHFFFAOYSA-N 0.000 description 2
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- UQRKXZOISAAYQQ-UHFFFAOYSA-N diphenylphosphorylformaldehyde Chemical compound C=1C=CC=CC=1P(=O)(C=O)C1=CC=CC=C1 UQRKXZOISAAYQQ-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- YVORRXJAVSDKSP-UHFFFAOYSA-N hydroxymethyl acetate Chemical compound CC(=O)OCO.CC(=O)OCO.CC(=O)OCO YVORRXJAVSDKSP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- YACCECLVHQLZQK-UHFFFAOYSA-N methoxyperoxyethane Chemical compound CCOOOC YACCECLVHQLZQK-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N n-Nonyl alcohol Natural products CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical compound OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical group C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F277/00—Macromolecular compounds obtained by polymerising monomers on to polymers of carbocyclic or heterocyclic monomers as defined respectively in group C08F32/00 or in group C08F34/00
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- 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
- G03F7/40—Treatment after imagewise removal, e.g. baking
- G03F7/405—Treatment with inorganic or organometallic reagents after imagewise removal
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
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- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Manufacturing & Machinery (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Inorganic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Disclosed is a negative photosensitive resin composition comprised of (A) an annual olefin resin containing repeating units represented by a general formula (1) (where R1, R2, R3 and R4 each represent an independent substituent group chosen from: a hydrogen atom, an alkyl group having 1-15 carbon atoms, an alkenyl group with 2-20 carbon atoms, a cycloalkyl group with 5-15 carbon atoms, an aryl group with 6-20 carbon atoms or an alkoxy group with 1-20 carbon atoms; or a hydrolysable silyl group, an alkoxycarbonyl group with 2-20 carbon atoms, a trialkylsiloxy carbonyl group with 4-20 carbon atoms, an alkyl carbonyl oxy group with 2-20 carbon atoms, an alkenyl carbonyl oxy group with 3-20 carbon atoms and an oxetanyl group; attached directly or via and jointly with an oxygen atom, a nitrogen atom or a sulphur atom), (B) a polyfunctional acrylic monomer and (C) a photoinitiator.
Description
Technical field
The present invention relates to a kind of negative light-sensitive resin combination, interlayer dielectric and forming method thereof.
Background technology
Thin film transistor (TFT) (below; Note work " TFT ") in the electronic unit such as type liquid crystal display cells, magnetic head element, integrated circuit component and solid-state image pickup tube elements; In order to make the wiring closet insulation of stratiform configuration, interlayer dielectric (referring to patent documentation 1) is set usually.As its material, because it is few and have the material of abundant flatness to be preferred for obtaining the process number of required pattern form, negative light-sensitive resin combination (referring to patent documentation 2) therefore is widely used.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2000-10089 communique
Patent documentation 2: No. 3650985 communique of Jap.P.
Summary of the invention
The problem that invention will solve
In above-mentioned electronic unit, TFT type liquid crystal display cells is that process forms ELD on interlayer dielectric, and the operation that forms liquid crystal orientation film is more above that made.At this moment, because this interlayer dielectric is exposed under the hot conditions, therefore need have sufficient patience in the formation operation of ELD to it.
In addition, in recent years, for TFT type liquid crystal display cells, big pictureization, high briliancyization are arranged, height becomes more meticulous and multiple technologies trend such as high-speed responseization, it is complicated that the structure of liquid crystal display cells also becomes thereupon.Therefore, for used interlayer dielectric, at low-k, high transmission rate (> 80%; Aspects such as λ=400nm) also require the high-performance that improved than in the past; Simultaneously, on the structure of liquid crystal display cells, also begin requirement and can realize the specific (special) requirements such as thick filmization to the 50 μ m.
Yet; Be generally used for the negative light-sensitive resin combination of the formation of existing interlayer dielectric; Realize that at the same time thick filmization and high permeability and high resolving power aspect are extremely difficult, a kind of can formation of strong request exploitation with the negative light-sensitive resin combination of the interlayer dielectric of such characteristic.
The present invention In view of the foregoing carries out; Even its purpose is to provide a kind of thick filmization, also can form all negative light-sensitive resin combinations of the interlayer dielectric of ten minutes excellence of various characteristicses such as resolution, the transparency, thermotolerance, heat-resisting discolouration and solvent resistance.In addition, the object of the invention also is to provide a kind of by formed interlayer dielectric of this negative light-sensitive resin combination and forming method thereof.
The method of dealing with problems
The present invention provides a kind of negative light-sensitive resin combination, and it contains: comprise (A) cyclic olefin resin, (B) multi-functional acrylic monomers of the represented repetitive of formula (1) and (C) Photoepolymerizationinitiater initiater.In the formula (1), R
1, R
2, R
3And R
4Expression independently of one another be selected from hydrogen atom, carbon number be 1～15 alkyl, carbon number be 2～20 thiazolinyl, carbon number be 5～15 naphthenic base, carbon number be 6～20 aryl or carbon number be 1～20 alkoxy, or water-disintegrable silicyl, carbon number be that 2～20 alkoxy carbonyl, carbon number are that 4～20 trialkylsiloxy carbonyl, carbon number are that 2～20 alkyl carbonyl oxy, carbon number are 3～20 the thiazolinyl carbonyl oxygen base and the substituting group of oxa-cyclobutyl, and also can directly or through oxygen atom, nitrogen-atoms or sulphur atom be connected to each other.
[changing 1]
Even have the negative light-sensitive resin combination thick filmization of above-mentioned formation, also can form all very excellent interlayer dielectric of various characteristicses such as resolution, the transparency, thermotolerance, heat-resisting discolouration and solvent resistance.
(A) cyclic olefin resin preferably comprise above-mentioned general formula (1) represented, R
1, R
2, R
3And R
4Structural unit for hydrogen atom.
In addition, (A) cyclic olefin resin preferably comprise above-mentioned general formula (1) represented, R
1, R
2, R
3And R
4Any one be the structural unit of 2～20 alkyl carbonyl oxy for carbon number.
The present invention provides a kind of negative light-sensitive resin combination; It can be used for the formation method of interlayer dielectric, and it is the ultraviolet operation below the 400nm that said method has at least a portion illumination wavelength by the formed film of this negative light-sensitive resin combination.
Negative light-sensitive resin combination of the present invention also preferably further contains (D) alkali soluble resin.
It is a kind of by the formed interlayer dielectric of above-mentioned negative light-sensitive resin combination that the present invention provides.
The present invention provides a kind of formation method of interlayer dielectric; It has the operation of developing by the operation of at least a portion irradiates light of the formed film of above-mentioned negative light-sensitive resin combination, with the aforementioned films after the rayed and the above-mentioned film after burning till development, forms the operation of interlayer dielectric.
The invention effect
According to the present invention,, also can form all negative light-sensitive resin combinations of the interlayer dielectric of ten minutes excellence of various characteristicses such as resolution, the transparency, thermotolerance, heat-resisting discolouration and solvent resistance even a kind of thick filmization can be provided.
Embodiment
Below, preferred implementation of the present invention is elaborated.
Negative light-sensitive resin combination in this embodiment contains: (A) cyclic olefin resin, (B) multi-functional acrylic monomers and (C) Photoepolymerizationinitiater initiater.Below, each composition is elaborated.
-(A) cyclic olefin resin-
(A) cyclic olefin resin of this embodiment is the polymkeric substance with the represented repetitive of formula (1).
[changing 2]
Above-mentioned R
1, R
2, R
3And R
4Expression independently of one another be selected from hydrogen atom, carbon number be 1～15 alkyl, carbon number be 2～20 thiazolinyl, carbon number be 5～15 naphthenic base, carbon number be 6～20 aryl or carbon number be 1～20 alkoxy, or water-disintegrable silicyl, carbon number be that 2～20 alkoxy carbonyl, carbon number are that 4～20 trialkylsiloxy carbonyl, carbon number are that 2～20 alkyl carbonyl oxy, carbon number are 3～20 the thiazolinyl carbonyl oxygen base and the substituting group of oxa-cyclobutyl, and also can directly or through oxygen atom, nitrogen-atoms or sulphur atom be connected to each other.
More preferably, R
1, R
2, R
3And R
4Be that 1～15 alkyl, carbon number are that 2～20 thiazolinyl, carbon number are that 6～15 aryl or carbon number are that 6～20 alkoxy and carbon number are the substituting group of 2～20 alkyl carbonyl oxy for being selected from hydrogen atom, carbon number independently of one another.Through forming such formation, can obtain the dissolubility of all kinds of solvents is improved such effect.
As water-disintegrable silicyl, specifically can enumerate trimethoxysilyl, methyl dimethoxy oxygen base silicyl here.
As carbon number is 2～20 alkyl carbonyl oxy, specifically can enumerate methyl ester group, tert-butyl group ester group, 2-ethylhexyl ester group, benzyl ester group, cyclopentyl ester group, cyclohexyl ester group and allyl ester group.Wherein, consider, especially preferably use methyl ester group and benzyl ester group etc. from stable on heating viewpoint.
Used (A) cyclic olefin resin in this embodiment is a benchmark with the total amount of the formula in the cyclic olefin (1) structural unit, preferably contains the represented R of 1 mole of above-mentioned general formula more than the % (1)
1, R
2, R
3And R
4Be the structural unit of hydrogen atom, and more preferably contain 10 moles more than the %.When this ratio is 1 mole of % when above, the tendency that exists the thermotolerance of rewarding negative light-sensitive resin combination to improve.In addition, aforementioned proportion is preferably 60 moles below the %, and more preferably 50 moles below the %.When aforementioned proportion is 60 moles of % when following, have the tendency that the solubility to the solvent that is used to modulate negative light-sensitive resin combination improves.
Used (A) cyclic olefin resin in this embodiment is a benchmark with the total amount of the formula in the cyclic olefin (1) structural unit, preferably contains the represented R of 1 mole of above-mentioned general formula more than the % (1)
1, R
2, R
3And R
4Any one be the structural unit of 2～20 alkyl carbonyl oxy for carbon number, and more preferably contain 10 moles more than the %.When this ratio is 1 mole of % when above, have the tendency that can obtain the solubility of the solvent that is used to modulate negative light-sensitive resin combination is improved such effect.Aforementioned proportion is preferably 60 moles below the %, and more preferably 50 moles below the %.When aforementioned proportion is 60 moles of % when following, the thermotolerance that has the negative light-sensitive resin combination that can obtain gained improves the tendency of such effect.
Above-mentioned (A) cyclic olefin resin can be through in solvent, in the presence of metallic catalyst, makes the represented monomer of formula (2) carry out addition copolymerization (pay add gross weight close) and makes.
[changing 3]
As the solvent that is used for making (A) cyclic olefin resin; For example, can enumerate halogenated hydrocarbons such as aromatic hydrocarbons such as clicyclic hydrocarbons such as aliphatic hydrocarbons such as pentane, hexane and heptane, cyclohexane, benzene, toluene and xylene, methylene chloride, chloroform and chlorobenzene, nitromethane, nitrobenzene and acetonitrile etc. nitrogenous is hydrocarbon and ethers such as Anaesthetie Ether 、 diox and tetrahydrofuran.These solvents can use a kind separately, perhaps can use mixing more than 2 kinds.
As the catalyzer (E) that is used for the polymerization of (A) cyclic olefin resin, preferred cyclopentadiene base system part at least and the complex compound that is selected from a kind of transition-metal coordination gained of periodic table the 8th family's element, the 9th family's element and the 10th family's element.As object lesson, can enumerate iron (Fe), cobalt (Co), nickel (Ni), ruthenium (Ru), rhodium (Rh), palladium (Pd) and platinum (Pt).Wherein, consider that from improving the active viewpoint of polymerization catalyst preferred element is cobalt, nickel, palladium and platinum, and especially preferably uses palladium.
As the promotor (F) that is used for the polymerization of (A) cyclic olefin resin, the material that dissociates of the part of the complex compound of preferred promotion formation catalyzer (E).For example, can enumerate the ionic compound that following non-coordination property negative ion of giving an example and kation are combined.
As non-coordination property negative ion; For example; Can enumerate four (phenyl) borate (ボ レ one ト), four (fluoro phenyl) borate, four (difluorophenyl) borates, four (trifluorophenyl) borate, four (tetrafluoro phenyl) borate, four (pentafluorophenyl group) borates, four (trifluoromethyl phenyl) borate, four (toluyl (ト リ イ Le)) borate, four (xylyl) borate, (triphenyl; Pentafluorophenyl group) borate, [three (pentafluorophenyl groups); Phenyl] borate and 13 hydrogen-7, the two carbon 11-borate roots (ト リ デ カ Ha イ De ラ イ De-7,8-ジ カ Le バ ウ Application デ カ ボ レ one ト) of 8-.
As above-mentioned kation, can enumerate carbocation, oxygen kation, ammonium cation 、 phosphonium cation, cycloheptatriene kation (シ Network ロ ヘ プ チ Le ト リ エ ニ Le カ チ オ Application) and have ferrocene cation (Off エ ロ セ ニ ウ system カ チ オ Application) of transition metal etc.
As the object lesson of carbocation, can enumerate triphenylcarbenium kation and tri-substituted phenyl carbocation etc. three and replace carbocation.As the object lesson of tri-substituted phenyl carbocation, can enumerate three (aminomethyl phenyl) carbocations and three (3,5-dimethylphenyl) carbocation.
Object lesson as ammonium cation; Can enumerate trialkyl ammonium kation, N such as trimethyl ammonium kation, triethyl ammonium kation, tripropyl ammonium cation, tributyl ammonium kation and three (normal-butyl) ammonium cation, N-diethylaniline (ア ニ リ ニ ウ system) kation and N, N-2; 4; N such as 6-pentamethylaminobenzene kation, N-dialkyl aniline kation, and dialkyl ammonium kations such as two (isopropyl) ammonium cations and dicyclohexyl ammonium cation.
The object lesson of Zuo Wei phosphonium cation can be enumerated triphenyl phosphonium kation, three (aminomethyl phenyl) phosphonium cation and three (San Fang Ji phosphonium cation such as 3,5-dimethylphenyl) phosphonium cation.
As above-mentioned ionic compound; For example be trityl four (pentafluorophenyl group) borate, triphenylcarbenium four (fluoro phenyl) borate, N; Accelerine four (pentafluorophenyl group) borate and 1,1 '-dimethyl ferrocene four (pentafluorophenyl group) borate.
In this embodiment; Catalyzer (E) is different along with the variation of various conditions with the ratio of promotor (F); Therefore can not decide without exception; But be preferably 1/0.1～1/10000 in E/F (mol ratio) usually, more preferably 1/0.5～1/5000, and further be preferably 1/1～1/2000.
The polystyrene conversion weight-average molecular weight of (A) cyclic olefin resin in this embodiment (below, be called " Mw ") be preferably 2 * 10
3To 2 * 10
5, and more preferably 2 * 10
4To 1.8 * 10
5If Mw is less than 2 * 10
3, the thermotolerance of gained tunicle and the tendency that skin hardness descends are then arranged.On the other hand, if Mw surpasses 2 * 10
5, development property is then arranged, photosensitive polymer combination is modulated the tendency with the decreased solubility of solvent.
-(B) multi-functional acrylic monomers-
As (B) multi-functional acrylic monomers of this embodiment, can use above multifunctional (methyl) acrylic ester of 2 officials ability.Specifically; Can enumerate dipentaerythritol acrylate, dipentaerythritol hexamethyl acrylic ester, dipentaerythritol five acrylic ester, dipentaerythritol pentamethyl acrylic ester, tetramethylol methane tetraacrylate, pentaerythrite tetramethyl acrylic ester, pentaerythritol triacrylate, pentaerythritol acrylate trimethyl, pentaerythritol diacrylate, dimethyl pentaerythritol acrylate, tetra methylol propane tetraacrylate, tetra methylol propane tetramethyl acrylic ester, tetramethylol methane tetraacrylate, tetramethylol methane tetramethyl acrylic ester, trimethylolpropane triacrylate, trimethylol-propane trimethacrylate, 1; 3; 5-triacryl six hydrogen-S-triazine, 1; 3; 5-trimethyl acryloyl group six hydrogen-S-triazine, three (hydroxyethyl acryloyl group) isocyanuric acid ester, three (hydroxyethyl methacryl) isocyanuric acid ester, triacryl dimethoxym ethane, trimethyl acryloyl group dimethoxym ethane, 1; 6-hexanediol acrylic ester, 1; 6-hexanediol methacrylate, neopentylglycol diacrylate, neopentylglycol dimethacrylate, glycol diacrylate, ethylene glycol dimethacrylate, 2-hydroxyl propylene glycol diacrylate, 2-hydroxyl propylene glycol dimethylacrylate, diethylene glycol diacrylate, diethylene glycol dimethylacrylate, Isopropanediol diacrylate, Isopropanediol dimethylacrylate, triethylene glycol diacrylate, triethylene glycol dimethylacrylate, N; N '-two (acryloyl group) halfcystine, N, N '-two (methacryl) halfcystine, sulphur support diethanol diacrylate, sulphur support diethanol dimethylacrylate, bisphenol a diacrylate, bisphenol a dimethacrylate, Bisphenol F diacrylate, Bisphenol F dimethylacrylate, bisphenol S diacrylate, bisphenol S dimethylacrylate, two phenoxetol fluorenes diacrylates, two phenoxetol fluorenes dimethylacrylates, diallyl ether bisphenol-A, adjacent diallyl bisphenol, diallyl maleate and triallyl trimellitate.Through using above multifunctional (methyl) acrylic ester of 2 officials ability, can obtain physical strength and strengthen such effect.
Above-mentioned multi-functional acrylic monomers; Can be easy to as commodity obtain; For example, can enumerate KYARAD T-1420, KYARAD DPHA, KYARAD DPHA-2C, KYARAD D-310, KYARAD D-330, KYARAD DPCA-20, KYARAD DPCA-30, KYARAD DPCA-60, KYARAD DPCA-120, KYARAD DN-0075, KYARAD DN-2475, KYARAD R-526, KYARAD NPGDA, KYARAD PEG400DA, KYARAD MANDA, KYARAD R-167, KYARAD HX-220, KYARAD HX620, KYARAD R-551, KYARAD R-712, KYARAD R-604, KYARAD R-684, KYARAD GPO-303, KYARAD TMPTA, KYARAD THE-330, KYARAD TPA-320, KYARAD TPA-330, KYARAD PET-30, KYARAD RP-1040 (above is Japanese chemical drug (strain) manufacturing), Aronix (ア ロ ニ Star Network ス) M-210, Aronix M-240, Aronix M-6200, Aronix M-305, Aronix M-309, Aronix M-400, Aronix M-402, Aronix M-405, Aronix M-450, Aronix M-7100, Aronix M-8030, AronixM-8060, Aronix M-1310, Aronix M-1600, Aronix M-1960, Aronix M-8100, Aronix M-8530, Aronix M-8560, Aronix M-9050 (above is that make in East Asia synthetic (strain)), Viscoat (PVC ス コ one ト) 295, Viscoat 300, Viscoat 360, Viscoat GPT, Viscoat 3PA, Viscoat 400, Viscoat 260, Viscoat 312 and Viscoat 335HP (above is that Osaka organic chemistry industrial (strain) is made).In addition, these multi-functional acrylic monomerss can use a kind separately, perhaps can use mixing more than 2 kinds.
In these multi-functional acrylic monomerss; From the dissolubility and the transparency to developer solution, preferred especially dipentaerythritol acrylate, dipentaerythritol hexamethyl acrylic ester, dipentaerythritol five acrylic ester, dipentaerythritol pentamethyl acrylic ester, tetramethylol methane tetraacrylate, pentaerythrite tetramethyl acrylic ester, pentaerythritol triacrylate, pentaerythritol acrylate trimethyl, pentaerythritol diacrylate and dimethyl pentaerythritol acrylate.
-(C) Photoepolymerizationinitiater initiater-
As (C) Photoepolymerizationinitiater initiater in this embodiment, can enumerate the photonasty radical polymerization initiator.As the photonasty radical polymerization initiator; For example; Can enumerate acyloin ethers, thioxanthones, 2 such as acyloin classes such as α such as benzil and diacetyl-two ketone, benzoin, benzoin methyl ether, benzoin ethylether and benzoin isopropyl ether; 4-diethyl thioxanthone, thioxanthones-4-sulfonic acid, benzophenone, 4, benzophenone, acetophenone, p-dimethylamino benzoylformaldoxime, α such as 4 '-two (dimethylamino) benzophenone and 4,4 '-two (diethylamino) benzophenone; α '-dimethoxy acetoxyl group benzophenone, 2; 2 '-dimethoxy-2-phenyl acetophenone, p-methoxyacetophenone, 2-methyl (4-(methyl mercapto) phenyl)-2-morpholino (モ Le Off オ リ ノ)-1-acetone and 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butane-acetophenones, anthraquinones and 1 such as 1-ketone, quinones such as 4-naphthoquinones, phenacyl chloride, trisbromomethyl phenyl sulfone and three (trichloromethyl)-halogen compounds, 2,4 such as s-triazine; 6-trimethylbenzene formyl diphenyl phosphine oxide, two (2; 6-dimethoxy benzoyl)-2,4,4-trimethyl-amyl group phosphine oxide and two (2; 4,6-trimethylbenzene formyl) superoxide such as acylphosphine oxide such as phenyl phosphine oxide and di-tert-butyl peroxide etc.Through usability photosensitiveness radical polymerization initiator, can obtain the susceptibility raising such effect of negative light-sensitive resin combination to light.
Commercially available article as these photonasty radical polymerization initiators; For example, can enumerate IRGACURE-184, IRGACURE-369, IRGACURE-500, IRGACURE-651, IRGACURE-907, IRGACURE-1700, IRGACURE-819, IRGACURE-124, IRGACURE-1000, IRGACURE-2959, IRGACURE-149, IRGACURE-1800, IRGACURE-1850, IRGACURE-OXE-01, Darocur-1173, Darocur-1116, Darocur-2959, Darocur-1664, Darocur-4043 (above is the Ciba manufactured), KAYACURE-DETX, KAYACURE-MBP, KAYACURE-DMBI, KAYACURE-EPA, KAYACURE-OA (above is Japanese chemical drug (strain) manufacturing), LUCIRINTPO (BASFCo.LTD manufacturing), VICURE-10, VICURE-55 (the above STAUFFER Co.LTD of being makes), TRIGONALP1 (AKZO Co.LTD manufacturing), SANDORAY1000 (SANDOZ Co.LTD manufacturing), DEAP (APJOHN Co.LTD manufacturing), QUANTACURE-PDO, QUANTACURE-ITX and QUANTACURE-EPD (the above WARDBLEKINSOP Co.LTD of being makes).In addition, through and with these photonasty radical polymerization initiators and sensitization sensitizer, the negative light-sensitive resin combination of the high sensitivity that the inactivation that can also obtain causing because of oxygen is less.
In above-mentioned photonasty radical polymerization initiator; From to the transparency after the dissolubility of photosensitive polymer combination modulating liquid, the exposure; Be preferably α especially, α '-dimethoxy acetoxyl group benzophenone, 2-methyl (4-(methyl mercapto) phenyl)-2-morpholino-1-acetone and 2-methyl (4-(methyl mercapto) phenyl)-2-morpholino-1-acetone.
-(D) alkali soluble resin-
Alkali soluble resin as this embodiment; Can be from being suitably selection in the alkali soluble resin that has at least one group (for example, carboxyl, phosphate and sulfonic group etc.) that promotes alkali-soluble wire organic high molecular polymer, the molecule (being preferably with acrylic acid series copolymer, styrene based copolymer is the molecule of main chain).Wherein, the material that more preferably dissolves in organic solvent and can develop through weak base aqueous solution.
In the manufacturing of alkali soluble resin, for example, can be suitable for the method that adopts known radical polymerization.In radical polymerization; The kind and the amount of the temperature when making alkali soluble resin, pressure, radical polymerization initiator; And polymerizing condition such as solvent types, can set at an easy rate to those skilled in the art, and can form and confirm condition experimentally.
As above-mentioned wire organic high molecular polymer, be preferably the polymkeric substance that on side chain, has carboxylic acid.For example; Can enumerate methacrylic acid copolymer, acrylic copolymer, itaconic acid copolymer, butenoic acid multipolymer, maleic acid, the partial esterification of that kind of being put down in writing in each communique of japanese kokai publication sho 59-44615 number, special public clear 54-34327 number of Japan, special public clear 58-12577 number of Japan, special public clear 54-25957 number of Japan, japanese kokai publication sho 59-53836 number and japanese kokai publication sho 59-71048 number maleic acid, on side chain, have the acid cellulose derivant of carboxylic acid and make acid anhydrides and polymkeric substance carry out addition and the high molecular polymer that obtains etc. with hydroxyl; In addition; As preferred high molecular polymer, can also be set forth on the side chain high molecular polymer with (methyl) acryloyl group.
Among these, (methyl) benzyl acrylate/(methyl) acrylic copolymer and the multiple copolymer that comprises (methyl) benzyl acrylate/(methyl) acrylic acid/other monomer are particularly suitable.In addition, as useful material, the polymkeric substance of methacrylic acid 2-hydroxyl ethyl ester of can also having enumerated copolymerization.This polymkeric substance can use with amount mixing arbitrarily.
Except above-mentioned, can also enumerate (methyl) acrylic acid 2-hydroxypropyl acrylate/polystyrene macromolecular monomer/benzyl methacrylate/methacrylic acid copolymer, 2-hydroxyl-3-phenoxy propyl acrylic ester/polymethylmethacrylate macromonomer/benzyl methacrylate/methacrylic acid copolymer, methacrylic acid 2-hydroxyl ethyl ester/polystyrene macromolecular monomer/methyl methacrylate/methacrylic acid copolymer and the methacrylic acid 2-hydroxyl ethyl ester/polystyrene macromolecular monomer/benzyl methacrylate/methacrylic acid copolymer etc. put down in writing in the japanese kokai publication hei 7-140654 communique.
For the concrete structural unit of (D) alkali soluble resin, (methyl) acrylic acid with can be particularly suitable with the multipolymer of other monomer of its copolymerization.As can with other monomer of above-mentioned (methyl) acrylic acid copolymer, can enumerate (methyl) alkyl acrylate, (methyl) acrylic acid aryl ester and vinyl compound etc.Here, the hydrogen atom of alkyl and aryl also can be substituted base and replace.
As the object lesson of above-mentioned (methyl) alkyl acrylate and (methyl) acrylic acid aryl ester, can enumerate (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) butyl acrylate, (methyl) isobutyl acrylate, (methyl) acrylic acid pentyl ester, (methyl) Hexyl 2-propenoate, (methyl) 2-ethyl hexyl acrylate, (methyl) phenyl acrylate, benzyl acrylate, CA, acrylic acid naphthalene ester and cyclohexyl acrylate.
In addition; As above-mentioned vinyl compound; For example, can enumerate styrene, AMS, vinyltoluene, GMA, vinyl cyanide, vinyl acetate, N-vinyl pyrrolidone, tetrahydrofurfuryl methacrylate, polystyrene macromolecular monomer, polymethylmethacrylate macromonomer, CH
2=CR
5R
6[R here,
5Expression hydrogen atom or carbon number are 1～5 alkyl, R
6The expression carbon number is 6～10 aromatic hydrocarbon ring.] and CH
2=C (R
5) (COOR
7) [R here,
5Expression hydrogen atom or carbon number are 1～5 alkyl, R
7The expression carbon number is that 1～8 alkyl or carbon number are 6～12 aralkyl.]。These can copolymerization other monomer, can use a kind separately, perhaps can combination more than 2 kinds be used.
Other monomer that preferably can copolymerization is to be selected from CH
2=CR
5R
6, CH
2=C (R
5) (COOR
7), (methyl) phenyl acrylate, (methyl) benzyl acrylate and cinnamic at least a, and be preferably CH especially
2=CR
5R
6And/or CH
2=C (R
5) (COOR
7).
The modulation of-negative light-sensitive resin combination-
Negative light-sensitive resin combination in this embodiment is modulated through above-mentioned (A) cyclic olefin resin, (B) multi-functional acrylic monomers and (C) each composition of Photoepolymerizationinitiater initiater are mixed.Above-mentioned negative light-sensitive resin combination is dissolved in aptly in the appropriate solvent and with solution state and uses.For example, can through will (A) cyclic olefin resin, (B) multi-functional acrylic monomers, (C) Photoepolymerizationinitiater initiater and other compounding ingredient as required with the regulation mixed, and modulate the negative light-sensitive resin combination of solution state.
For the negative light-sensitive resin combination in this embodiment, with respect to (A) cyclic olefin resin 10 weight portions, preferably with 10～150 weight portions, and more preferably the ratio of 40～120 weight portions contain (B) multi-functional acrylic monomers.When (B) multi-functional acrylic monomers during, have and fully to obtain photosensitive tendency less than 10 weight portions.On the other hand, when surpassing 150 weight portions, the tendency that then has fracture strength to descend.In addition, (C) Photoepolymerizationinitiater initiater preferably with 1～40 weight portion, and more preferably the ratio of 3～35 weight portions contain.When (C) Photoepolymerizationinitiater initiater during, have the tendency that can't obtain thermotolerance, skin hardness and resistance to chemical reagents less than 1 weight portion.On the other hand, when surpassing 40 weight portions, the tendency that then has the transparency to descend.
As the solvent of the negative light-sensitive resin combination that is used to modulate this embodiment, can use dissolving (A) cyclic olefin resin, (B) multi-functional acrylic monomers and (C) each composition of Photoepolymerizationinitiater initiater, and not with the solvent of each composition reaction.Specifically, can enumerate that propylene glycol alkyl ether acetic acid ester class, toluene and xylene etc. such as propylene glycol alkyl ether acetic acid ester class, methyl proxitol propionic ester, propylene glycol ethylether propionic ester, propylene glycol propyl ether propionic ester and propylene glycol butyl ether propionic esters such as propylene-glycol monoalky lether classes such as diethylene glycol classes such as monoethylene glycol alkyl ether acetate esters, diethylene glycol monomethyl ether, TC, diethylene glycol dimethyl ether, diethylene glycol ethyl-methyl ether and diethylene glycol diethyl ether, methyl proxitol, propylene glycol ethylether, propylene glycol propyl ether and propylene glycol butyl ether such as glycol ethers such as ethers such as alcohols such as methyl alcohol and ethanol, tetrahydrofuran, glycol monomethyl methyl ether and ethylene glycol monomethyl ether, methylcellosolve acetate and ethyl cellosolve acetate, methyl proxitol acetate, propylene glycol ethylether acetic acid esters, propylene glycol propyl ether acetic acid esters and propylene glycol butyl ether acetic acid esters are aromatic hydrocarbon based, ketone and ester classes such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl methyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy methyl acetate, hydroxyl ethyl acetate, glycolic acid butyl ester, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, 3-hydroxy methyl propionate, 3-hydracrylic acid ethyl ester, 3-hydracrylic acid propyl ester, 3-hydroxy methyl propionate, 3-butoxy ethyl propionate, 3-butoxy propyl propionate and 3-butoxy butyl propionate such as MEK, cyclohexanone and 4-hydroxy-4-methyl-2 pentanone.
In these solvents, from dissolubility, with the reactive of each composition and the easy degree of filming and forming, can preferably use propylene glycol alkyl ether acetic acid ester class, propylene glycol alkyl ether acetic acid ester class and aromatic hydrocarbon based.
Further, can also and use above-mentioned solvent and high boiling solvent.As can and the high boiling solvent of usefulness; For example; Can enumerate N-NMF, N; Dinethylformamide, N-methyl N-formailide, N-methylacetamide, DMAC N,N, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), benzylisoeugenol, hexyl ether, acetonyl acetone, isophorone, caproic acid, sad, 1-octanol, 1 nonyl alcohol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethy-aceto oxalate, diethyl maleate, gamma-butyrolacton, ethylene carbonate, carbonic allyl ester and ethylene glycol monophenyl ether acetic acid esters.The negative light-sensitive resin combination of this embodiment can also contain above-mentioned other composition in addition as required in the scope of not damaging the object of the invention.
The negative light-sensitive resin combination of modulation can also be after millipore filter etc. about 0.2～0.5 μ m filters use to be provided again using the aperture as stated.
The formation method of-interlayer dielectric-
The formation method of the interlayer dielectric of this embodiment comprises following at least operation.(1) the operation of the film that forms above-mentioned negative light-sensitive resin combination on the substrate, (2) at least a portion irradiates light of above-mentioned film (below be sometimes referred to as " exposure ".) operation, (4) of operation, (3) the above-mentioned film development after will making public burn till above-mentioned film after the development (below be sometimes referred to as " curing (ベ one Network) ".), the operation of formation interlayer dielectric.
Here, so-called in this embodiment " light " is meant and comprises ultraviolet ray, far ultraviolet, X ray, electron beam, molecular beam, gamma-rays, synchrotron light (シ Application Network ロ ト ロ Application light) and proton beam etc.
Below, these operations are elaborated.
-(1) operation-
In (1) operation, negative light-sensitive resin combination preferably as liquid composition, is formed film on substrate surface, and carry out prebake except that desolvating, form the film of negative light-sensitive resin combination.
As the kind of operable substrate, the substrate etc. that can enumerate glass substrate, silicon wafer and on their surface, form various metals.As the method for the film that forms composition solution, not special the qualification is preferably the method that adopts coating.As coating process, can adopt spray-on process, rolling method, spin-coating method, slit die rubbing method, rod to be coated with proper methods such as method and ink-jet method.
The condition of prebake is according to the kind of the constituent of negative light-sensitive resin combination and usage ratio etc. and different, for example, can under 60～130 ℃, carry out 30 second～15 minute.Thickness as the above-mentioned film that forms is preferably 5～20 μ m as the value after the prebake.
-(2) operation-
In (2) operation, at least a portion of the above-mentioned film that forms is made public.At this moment, when only the part of above-mentioned film being made public, make public through photomask usually with regulation shape pattern.
As the used light of exposure, for example, can enumerate i line (wavelength is 365nm) and wait X ray such as far ultraviolet, synchrotron light such as ultraviolet, KrF PRK and ArF PRK, and charged particle beam such as electron beam.In these light, preferred ultraviolet ray, more preferably wavelength is the ultraviolet ray below the 400nm, and further preferably comprises the ultraviolet ray of i line.Exposure preferably is made as 50～10000J/m
2About.
-(3) operation-
In (3) operation, the above-mentioned film after the exposure is developed, remove unexposed portion, form the pattern of regulation shape thus.
As used developer solution in developing; Be preferably NaOH, potassium hydroxide, sodium carbonate, sodium silicate (ケ イ acid Na ト リ ウ system), sodium silicate (メ タ ケ イ acid Na ト リ ウ system), ammonia, ethamine, n-propylamine, diethylamine, DEAE diethylaminoethanol, di-n-propylamine, triethylamine, methyl-diethyl-amine, dimethylethanolamine, triethanolamine, TMAH, tetraethyl ammonium hydroxide, pyrroles, piperidines, 1; 8-diazabicyclo [5; 4,0]-and 7-undecylene and 1,5-diazabicyclo [4; 3,0]-WS of alkali compounds such as 5-nonene.In the WS of above-mentioned alkali compounds, can add water-miscible organic solvent and surfactants such as amount of methanol and ethanol.
In addition, in this embodiment, when not containing insoluble composition such as filler, pigment when negative light-sensitive resin combination,, can also use the various organic solvents of dissolving constituent as developer solution.
As developing method, can adopt the liquid method of containing (liquid is contained the り method), infusion process, shake infusion process and towards pouring method proper methods such as (シ ヤ ワ one methods).
Development time is formed and difference according to the cooperation of negative light-sensitive resin combination, for example, and can be for establishing for 30～300 seconds.In addition, be used to form the negative light-sensitive resin combination of interlayer dielectric, if development time surpasses more than 20 seconds from top condition all the time; The pattern that then forms can produce and defective such as peel off; Therefore need strictly control development time, and under the situation of negative light-sensitive resin combination of the present invention, even be more than 30 seconds from the overtime of optimum development time; Also can form good pattern, and the yield rate of product improves.
-(4) operation-
In (4) operation, after carrying out post-exposure as required, the above-mentioned film after developing is cured through heating arrangements such as hot plate and baking ovens, thereby above-mentioned film is solidified, form interlayer dielectric.As the light that is used for post-exposure, for example, can enumerate X ray such as far ultraviolet, synchrotron light such as ultraviolet ray such as i line (wavelength is 365nm), KrF PRK and ArF PRK, and charged particle beam such as electron beam.
In these light, preferred ultraviolet ray, more preferably wavelength is the ultraviolet ray below the 400nm, and further more preferably comprises the ultraviolet ray of i line.The exposure of post-exposure preferably is made as 50～10000J/m
2The condition of curing is according to the kind of the constituent of negative light-sensitive resin combination and usage ratio, desirable pattern form and used heating arrangement etc. and different; And under the situation of hot plate; For example being 150～240 ℃ descended 10～30 minutes; Under the situation of baking oven, for example be 150～240 ℃ and descended 30～90 minutes.In addition, when curing, can also adopt substep baking process that carries out heat treated more than 2 times etc.
In this wise, can on substrate, form the target interlayer dielectric.Even the interlayer dielectric thick filmization of gained; Various characteristicses such as its resolution, the transparency, thermotolerance, heat-resisting discolouration and solvent resistance are also all excellent; For example, can be used to electronic units such as various liquid crystal display cells, magnetic head element, integrated circuit component and solid-state imager that comprise TFT type liquid crystal display cells etc. in extremely suitable ground.In addition, the formation method according to the interlayer dielectric of this embodiment can form the interlayer dielectric with excellent specific property easily with high finished product rate.
Embodiment
Below, show that embodiment does explanation more specifically to the present invention, but the present invention is not limited thereto.
(embodiment 1)
The modulation of-negative light-sensitive resin combination-
With Aronix M-305 (East Asia synthetic (strain) manufacturing of 10g as (B) multi-functional acrylic monomers; Trade name) is dissolved in the 36.4g toluene; In the solution of gained, add 1g (A) cyclic olefin resin and 0.6g 2-methyl isophthalic acid-(4-methyl mercapto phenyl)-2-morpholino propane-1-ketone (Ciba manufactured as (C) Photoepolymerizationinitiater initiater; Trade name: IRGACURE-907), wherein said (A) cyclic olefin resin is R
1, R
2And R
4Be hydrogen atom, R
3Monomer and R for the methyl ester group
1, R
2, R
3And R
4Carry out the material of copolymerization gained with 1:1 (mol ratio) for the monomer of hydrogen atom; Using the aperture then is that the film filter of 0.5 μ m filters, and modulating overall solid component concentration is the negative light-sensitive resin combination (S-1) of the such solution state of 30 quality %.
The formation of-interlayer dielectric-
Use table to go up a coating machine negative light-sensitive resin combination (S-1) is coated on the glass substrate, prebake 10 minutes in 80 ℃ explosion-proof dryer then, formation is filmed.Then, be 100mJ/cm through photomask with the cumulative exposure amount with regulation shape pattern
2Mode be the ultraviolet ray of 365nm to this exposure wavelength of filming.Then, use the tetramethylammonium hydroxide aqueous solution of 2.38 quality %, after 5 minutes,, remove unwanted part, obtain the pattern-like film with pure water washing 1 minute 25 ℃ of following immersion development.
Then, the pattern-like film of gained was cured in 200 ℃ baking oven 30 minutes, it is solidified, thereby the thickness that obtains having the predetermined pattern shape is the interlayer dielectric of 50 μ m.
-estimate-
Then, estimate according to following main points.The thickness of evaluation result and interlayer dielectric is shown in table 1 (down together) in the lump.
The evaluation of-resolution-
For the interlayer dielectric of gained, using diameter is the mask pattern evaluation resolution of 50 μ m.In the time can differentiating the square sectional hole patterns of 50 μ m, be evaluated as good (A), in the time can't differentiating the square sectional hole patterns of 50 μ m, be evaluated as bad (B).
The evaluation of-the transparency-
For the continuous film part of the interlayer dielectric of gained, use the transmitance of double beam spectrophotometer U-2900 ((strain) Hitachi makes, trade name) when measuring wavelength 400nm, and estimate.When this transmitance surpasses 90%, we can say the transparency good (A).
-stable on heating evaluation-
The interlayer dielectric of gained was heated 60 minutes in 220 ℃ baking oven, and the digital display scale (digimatic indicator) that uses (strain) mitsutoyo to make is measured the Thickness Variation rate (%) [thickness before=(thickness after the thickness-heating before the heating) * 100/ heating] before and after the heating and is estimated.When this rate of change is in 5% the time, we can say thermotolerance good (A).
The evaluation of-heat-resisting discolouration-
With nitrogen 250 ℃ baking oven is removed; The interlayer dielectric of gained was heated 60 minutes therein; And to the continuous film part of interlayer dielectric; Use the transmitance of double beam spectrophotometer U-2900 ((strain) Hitachi makes, trade name) when measuring wavelength 400nm, and estimate through the rate of change (%) [transmitance before=(transmitance after the transmitance-heating before the heating) * 100/ heating] of transmitance before and after the heating.When this rate of change is in 5% the time, we can say heat-resisting discolouration good (A).
The evaluation of-solvent resistance-
The glass substrate that has formed interlayer dielectric was flooded 15 minutes in 50 ℃ N-Methyl pyrrolidone, and the digital display scale that uses (strain) mitsutoyo to make is measured the Thickness Variation rate (%) [thickness before the dipping of=(thickness before the thickness-dipping behind the dipping) * 100/] of dipping front and back interlayer dielectric and is estimated.When this rate of change is in ± 10% the time, we can say solvent resistance good (A).
(embodiment 2)
Except in embodiment 1; (East Asia synthetic (strain) makes to use 10g Aronix M-402; Trade name) replaces beyond the 10gAronix M-305; Likewise modulate the negative light-sensitive resin combination (S-2) of solution state with embodiment 1, the thickness that obtains having the pattern form of regulation is the interlayer dielectric of 40 μ m.Evaluation result is shown in table 1.
[table 1]
| Thickness (μ m) | Resolution | The transparency | Thermotolerance | Heat-resisting discolouration | Solvent resistance | |
| Embodiment 1 | 50 | A | A | A | A | A |
| Embodiment 2 | 40 | A | A | A | A | A |
Can confirm embodiment 1 and 2 any one interlayer dielectrics, even thick filmization, its resolution, the transparency, thermotolerance, heat-resisting discolouration and solvent resistance are also all excellent.
Claims (7)
1. negative light-sensitive resin combination, it contains:
Comprise the represented repetitive of formula (1) (A) cyclic olefin resin,
(B) multi-functional acrylic monomers and
(C) Photoepolymerizationinitiater initiater,
In the formula, R
1, R
2, R
3And R
4Expression independently of one another be selected from hydrogen atom, carbon number be 1～15 alkyl, carbon number be 2～20 thiazolinyl, carbon number be 5～15 naphthenic base, carbon number be 6～20 aryl or carbon number be 1～20 alkoxy, or water-disintegrable silicyl, carbon number be that 2～20 alkoxy carbonyl, carbon number are that 4～20 trialkylsiloxy carbonyl, carbon number are that 2～20 alkyl carbonyl oxy, carbon number are 3～20 the thiazolinyl carbonyl oxygen base and the substituting group of oxa-cyclobutyl, and also can directly or through oxygen atom, nitrogen-atoms or sulphur atom be connected to each other.
2. negative light-sensitive resin combination as claimed in claim 1, wherein (A) cyclic olefin resin comprises the represented R of said general formula (1)
1, R
2, R
3And R
4Structural unit for hydrogen atom.
3. according to claim 1 or claim 2 negative light-sensitive resin combination, wherein (A) cyclic olefin resin comprises the represented R of said general formula (1)
1, R
2, R
3And R
4Any one be the structural unit of 2～20 alkyl carbonyl oxy for carbon number.
4. like each described negative light-sensitive resin combination of claim 1～3; It can be used for the formation method of interlayer dielectric, and it is the ultraviolet operation below the 400nm that said method has at least a portion illumination wavelength by the formed film of this negative light-sensitive resin combination.
5. like each described negative light-sensitive resin combination of claim 1～4, it further contains (D) alkali soluble resin.
6. by the formed interlayer dielectric of each described negative light-sensitive resin combination of claim 1～5.
7. the formation method of an interlayer dielectric, its have to by the operation of at least a portion irradiates light of the formed film of each described negative light-sensitive resin combination of claim 1～5,
The operation that said film after the rayed is developed and
Burn till the said film after the development, form the operation of interlayer dielectric.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010040341 | 2010-02-25 | ||
| JP2010-040341 | 2010-02-25 | ||
| PCT/JP2011/054019 WO2011105443A1 (en) | 2010-02-25 | 2011-02-23 | Negative photosensitive resin composition, interlayer insulating film and method of formation of same |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201510087880.5A Division CN104597712A (en) | 2010-02-25 | 2011-02-23 | Negative photo sensitive resin composition, interlayer insulating film and forming method thereof |
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| CN201510087880.5A Pending CN104597712A (en) | 2010-02-25 | 2011-02-23 | Negative photo sensitive resin composition, interlayer insulating film and forming method thereof |
| CN2011800109403A Pending CN102782579A (en) | 2010-02-25 | 2011-02-23 | Negative photosensitive resin composition, interlayer insulating film and method of formation of same |
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| Country | Link |
|---|---|
| JP (2) | JP5333581B2 (en) |
| KR (1) | KR20120132509A (en) |
| CN (2) | CN104597712A (en) |
| TW (1) | TWI413861B (en) |
| WO (1) | WO2011105443A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105867069A (en) * | 2015-02-10 | 2016-08-17 | 东友精细化工有限公司 | Negative-type photosensitive resin composition, photocuring pattern formed by using the same and image display device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5640864B2 (en) * | 2011-03-31 | 2014-12-17 | 日本ゼオン株式会社 | Negative photosensitive resin composition and electronic component |
| JP6065750B2 (en) * | 2013-05-29 | 2017-01-25 | 住友ベークライト株式会社 | Photosensitive resin composition and electronic device |
| JP6065749B2 (en) * | 2013-05-29 | 2017-01-25 | 住友ベークライト株式会社 | Photosensitive resin composition and electronic device |
| JP6183029B2 (en) * | 2013-07-25 | 2017-08-23 | 日本ゼオン株式会社 | Negative photosensitive resin composition and electronic component |
| US20160297181A1 (en) * | 2013-11-28 | 2016-10-13 | Zeon Corporation | Laminate |
| JP6477492B2 (en) * | 2013-12-03 | 2019-03-06 | 住友ベークライト株式会社 | Negative photoresist resin composition, cured film and electronic device |
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| CN1666150A (en) * | 2002-07-03 | 2005-09-07 | 住友电木株式会社 | Photosensitive compositions based on polycyclic polymers |
| JP2006293094A (en) * | 2005-04-12 | 2006-10-26 | Mitsubishi Chemicals Corp | Photopolymerizable composition, image forming material and imaging material |
| JP2008076860A (en) * | 2006-09-22 | 2008-04-03 | Showa Highpolymer Co Ltd | Photosensitive resin composition |
| CN101308327A (en) * | 2007-05-16 | 2008-11-19 | Jsr株式会社 | Radiation-sensed resin composition, layer insulation film, microlens and forming method thereof |
| JP2009216728A (en) * | 2008-03-06 | 2009-09-24 | Sumitomo Chemical Co Ltd | Photosensitive resin composition, pattern obtained from it, and display device |
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|---|---|---|---|---|
| TW200628981A (en) * | 2004-09-29 | 2006-08-16 | Sumitomo Bakelite Co | Semiconductor device |
| JP5224764B2 (en) * | 2007-09-28 | 2013-07-03 | 富士フイルム株式会社 | Pigment dispersion composition, photocurable composition, color filter, liquid crystal display device and solid-state imaging device |
-
2011
- 2011-02-23 JP JP2011509751A patent/JP5333581B2/en not_active Expired - Fee Related
- 2011-02-23 KR KR1020127024435A patent/KR20120132509A/en not_active Application Discontinuation
- 2011-02-23 WO PCT/JP2011/054019 patent/WO2011105443A1/en active Application Filing
- 2011-02-23 CN CN201510087880.5A patent/CN104597712A/en active Pending
- 2011-02-23 CN CN2011800109403A patent/CN102782579A/en active Pending
- 2011-02-25 TW TW100106488A patent/TWI413861B/en not_active IP Right Cessation
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1666150A (en) * | 2002-07-03 | 2005-09-07 | 住友电木株式会社 | Photosensitive compositions based on polycyclic polymers |
| JP2006293094A (en) * | 2005-04-12 | 2006-10-26 | Mitsubishi Chemicals Corp | Photopolymerizable composition, image forming material and imaging material |
| JP2008076860A (en) * | 2006-09-22 | 2008-04-03 | Showa Highpolymer Co Ltd | Photosensitive resin composition |
| CN101308327A (en) * | 2007-05-16 | 2008-11-19 | Jsr株式会社 | Radiation-sensed resin composition, layer insulation film, microlens and forming method thereof |
| JP2009216728A (en) * | 2008-03-06 | 2009-09-24 | Sumitomo Chemical Co Ltd | Photosensitive resin composition, pattern obtained from it, and display device |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105867069A (en) * | 2015-02-10 | 2016-08-17 | 东友精细化工有限公司 | Negative-type photosensitive resin composition, photocuring pattern formed by using the same and image display device |
| CN105867069B (en) * | 2015-02-10 | 2019-10-08 | 东友精细化工有限公司 | Negative light-sensitive resin combination, the photocuring pattern and image display device formed using it |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120132509A (en) | 2012-12-05 |
| JP2013101365A (en) | 2013-05-23 |
| JP5333581B2 (en) | 2013-11-06 |
| CN104597712A (en) | 2015-05-06 |
| WO2011105443A1 (en) | 2011-09-01 |
| TW201133144A (en) | 2011-10-01 |
| TWI413861B (en) | 2013-11-01 |
| JPWO2011105443A1 (en) | 2013-06-20 |
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