JP6513208B2 - 光塩基発生剤を含有する光イメージ化可能なポリオレフィン組成物 - Google Patents
光塩基発生剤を含有する光イメージ化可能なポリオレフィン組成物 Download PDFInfo
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- JP6513208B2 JP6513208B2 JP2017542905A JP2017542905A JP6513208B2 JP 6513208 B2 JP6513208 B2 JP 6513208B2 JP 2017542905 A JP2017542905 A JP 2017542905A JP 2017542905 A JP2017542905 A JP 2017542905A JP 6513208 B2 JP6513208 B2 JP 6513208B2
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- 239000000203 mixture Substances 0.000 title claims description 162
- 229920000098 polyolefin Polymers 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims description 114
- 239000000178 monomer Substances 0.000 claims description 68
- -1 1- (9,10-dioxo-9,10-dihydroanthracen-2-yl) ethyl cyclohexyl Chemical group 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 35
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000000654 additive Substances 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 238000004377 microelectronic Methods 0.000 claims description 12
- DKYWVDODHFEZIM-UHFFFAOYSA-M 2-(3-benzoylphenyl)propanoate Chemical compound [O-]C(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-M 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 230000005693 optoelectronics Effects 0.000 claims description 11
- 239000004971 Cross linker Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- NIQLOLNJWXWZHX-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group C1C2C(CC(O)(C(F)(F)F)C(F)(F)F)CC1C=C2 NIQLOLNJWXWZHX-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 239000002318 adhesion promoter Substances 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- FZNZZYVWAIIDEF-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-hydroxypiperidine-1-carboxylate Chemical compound C1CC(O)CCN1C(=O)OCC1=CC=CC=C1[N+]([O-])=O FZNZZYVWAIIDEF-UHFFFAOYSA-N 0.000 claims description 4
- GXPGUGRGRLIUPX-UHFFFAOYSA-N (4,5-dimethoxy-2-nitrophenyl)methyl 2,6-dimethylpiperidine-1-carboxylate Chemical compound C1=C(OC)C(OC)=CC(COC(=O)N2C(CCCC2C)C)=C1[N+]([O-])=O GXPGUGRGRLIUPX-UHFFFAOYSA-N 0.000 claims description 4
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 claims description 4
- RYRTYXMDSKQGDT-UHFFFAOYSA-N 5-(3-methoxybutoxy)-1-methylbicyclo[2.2.1]hept-2-ene Chemical compound COC(CCOC1C2C=CC(C1)(C2)C)C RYRTYXMDSKQGDT-UHFFFAOYSA-N 0.000 claims description 4
- DVYNRDXIYSHPDC-UHFFFAOYSA-N COCCC(=O)OC1C2C=CC(C1)(C2)C Chemical compound COCCC(=O)OC1C2C=CC(C1)(C2)C DVYNRDXIYSHPDC-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 claims description 4
- UCRXZJYCOMRCER-UHFFFAOYSA-N 2-[n,n'-di(propan-2-yl)carbamimidoyl]-1,1,3,3-tetramethylguanidine Chemical compound CC(C)NC(=NC(C)C)N=C(N(C)C)N(C)C UCRXZJYCOMRCER-UHFFFAOYSA-N 0.000 claims description 3
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical group C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 39
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 38
- 239000000126 substance Substances 0.000 description 30
- 235000012431 wafers Nutrition 0.000 description 27
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 25
- 238000011161 development Methods 0.000 description 23
- 230000018109 developmental process Effects 0.000 description 23
- 230000005855 radiation Effects 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 239000000758 substrate Substances 0.000 description 19
- BEHBBKCBARHMJQ-UHFFFAOYSA-N 5-(2-phenylethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCC1=CC=CC=C1 BEHBBKCBARHMJQ-UHFFFAOYSA-N 0.000 description 18
- 238000001723 curing Methods 0.000 description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 16
- 239000004065 semiconductor Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 14
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 229910052814 silicon oxide Inorganic materials 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000001878 scanning electron micrograph Methods 0.000 description 8
- 229920001897 terpolymer Polymers 0.000 description 8
- 230000000930 thermomechanical effect Effects 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 229920001774 Perfluoroether Polymers 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 239000002861 polymer material Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 150000001602 bicycloalkyls Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 3
- QECCQGLIYMMHCR-UHFFFAOYSA-N 2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane Chemical compound C1OC1COCC(COCC1OC1)(CC)COCC1CO1 QECCQGLIYMMHCR-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000012644 addition polymerization Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-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
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 2
- HHBBIOLEJRWIGU-UHFFFAOYSA-N 4-ethoxy-1,1,1,2,2,3,3,4,5,6,6,6-dodecafluoro-5-(trifluoromethyl)hexane Chemical compound CCOC(F)(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F HHBBIOLEJRWIGU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000011134 resol-type phenolic resin Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- 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
-
- 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
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive 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
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0395—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having a backbone with alicyclic moieties
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562117774P | 2015-02-18 | 2015-02-18 | |
| US62/117,774 | 2015-02-18 | ||
| PCT/US2016/017656 WO2016133795A1 (en) | 2015-02-18 | 2016-02-12 | Photoimageable polyolefin compositions containing photobase generators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018508824A JP2018508824A (ja) | 2018-03-29 |
| JP2018508824A5 JP2018508824A5 (https=) | 2018-08-16 |
| JP6513208B2 true JP6513208B2 (ja) | 2019-05-15 |
Family
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| JP2017542905A Active JP6513208B2 (ja) | 2015-02-18 | 2016-02-12 | 光塩基発生剤を含有する光イメージ化可能なポリオレフィン組成物 |
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| Country | Link |
|---|---|
| US (3) | US9952507B2 (https=) |
| JP (1) | JP6513208B2 (https=) |
| KR (1) | KR101998338B1 (https=) |
| CN (1) | CN107407872B (https=) |
| TW (1) | TWI652281B (https=) |
| WO (1) | WO2016133795A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2018538396A (ja) * | 2015-11-30 | 2018-12-27 | プロメラス, エルエルシー | 光酸発生剤及び塩基を含有する永久誘電体組成物 |
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| TWI732111B (zh) * | 2017-03-28 | 2021-07-01 | 日商住友電木股份有限公司 | 感光性組成物、彩色濾光片及由其衍生之微透鏡 |
| TWI758525B (zh) | 2017-08-10 | 2022-03-21 | 日商住友電木股份有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
| WO2021076131A1 (en) * | 2019-10-17 | 2021-04-22 | Promerus, Llc | Photosensitive compositions and applications thereof |
| TWI834019B (zh) * | 2020-01-09 | 2024-03-01 | 日商住友電木股份有限公司 | 作為3d列印材料之穩定本體聚合型多環烯烴組成物及其製備方法 |
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| US5563011A (en) * | 1993-04-21 | 1996-10-08 | Shipley Company Inc. | Color filter assembly |
| JP4054477B2 (ja) * | 1998-04-08 | 2008-02-27 | キヤノン株式会社 | 同一相手に対して複数の通信チャネルを用いた通信を行なうことが可能な通信装置、及びその制御方法 |
| US6849377B2 (en) * | 1998-09-23 | 2005-02-01 | E. I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| KR100481601B1 (ko) * | 1999-09-21 | 2005-04-08 | 주식회사 하이닉스반도체 | 광산 발생제와 함께 광염기 발생제를 포함하는 포토레지스트 조성물 |
| AU1603101A (en) * | 1999-11-17 | 2001-05-30 | E.I. Du Pont De Nemours And Company | Nitrile/fluoroalcohol-containing photoresists and associated processes for microlithography |
| EP1246013A3 (en) * | 2001-03-30 | 2003-11-19 | E.I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| US6737215B2 (en) * | 2001-05-11 | 2004-05-18 | Clariant Finance (Bvi) Ltd | Photoresist composition for deep ultraviolet lithography |
| US8030425B2 (en) * | 2002-07-03 | 2011-10-04 | Promerus Llc | Photosensitive compositions based on polycyclic polymers for low stress, high temperature films |
| CN101031595A (zh) * | 2003-10-31 | 2007-09-05 | 普罗米鲁斯有限责任公司 | 用于环烯烃潜聚合的单组分阳离子钯前引发剂 |
| KR101252321B1 (ko) * | 2005-06-30 | 2013-04-08 | 도레이 카부시키가이샤 | 감광성 수지 조성물 및 접착 개량제 |
| WO2010113813A1 (ja) * | 2009-03-31 | 2010-10-07 | 大日本印刷株式会社 | 塩基発生剤、感光性樹脂組成物、当該感光性樹脂組成物からなるパターン形成用材料、当該感光性樹脂組成物を用いたパターン形成方法並びに物品 |
| US20150007950A1 (en) * | 2011-12-27 | 2015-01-08 | Allure Home Creations Co., Inc. | Curtain hanging assembly |
| KR101572049B1 (ko) * | 2012-09-25 | 2015-11-26 | 프로메러스, 엘엘씨 | 사이클로올레핀성 중합체를 함유하는 말레이미드 및 그의 용도 |
| JP5803957B2 (ja) * | 2013-03-05 | 2015-11-04 | 信越化学工業株式会社 | パターン形成方法及びレジスト組成物 |
| WO2014176490A1 (en) * | 2013-04-26 | 2014-10-30 | Promerus, Llc | Photosensitive compositions and applications thereof |
| JP2015007770A (ja) * | 2013-05-29 | 2015-01-15 | 住友ベークライト株式会社 | 感光性樹脂組成物および電子装置 |
| JP6369132B2 (ja) * | 2013-06-28 | 2018-08-08 | 住友ベークライト株式会社 | ネガ型感光性樹脂組成物、硬化膜、電子装置およびポリマー |
| JP6306296B2 (ja) | 2013-07-09 | 2018-04-04 | 太陽インキ製造株式会社 | 感光性熱硬化性樹脂組成物およびフレキシブルプリント配線板 |
| WO2015038412A2 (en) * | 2013-09-16 | 2015-03-19 | Promerus, Llc | Amine treated maleic anhydride polymers with pendent silyl group, compositions and applications thereof |
| JP2015184325A (ja) * | 2014-03-20 | 2015-10-22 | 住友ベークライト株式会社 | 感光性樹脂組成物および電子装置 |
| KR20180088652A (ko) * | 2015-11-30 | 2018-08-06 | 프로메러스, 엘엘씨 | 광산발생제 및 염기 함유 영구유전체조성물 |
-
2016
- 2016-02-02 TW TW105103252A patent/TWI652281B/zh active
- 2016-02-12 CN CN201680018462.3A patent/CN107407872B/zh active Active
- 2016-02-12 WO PCT/US2016/017656 patent/WO2016133795A1/en not_active Ceased
- 2016-02-12 KR KR1020177025264A patent/KR101998338B1/ko active Active
- 2016-02-12 US US15/042,240 patent/US9952507B2/en active Active
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2018
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018538396A (ja) * | 2015-11-30 | 2018-12-27 | プロメラス, エルエルシー | 光酸発生剤及び塩基を含有する永久誘電体組成物 |
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|---|---|
| WO2016133795A1 (en) | 2016-08-25 |
| TW201634502A (zh) | 2016-10-01 |
| US20160238932A1 (en) | 2016-08-18 |
| US10634998B2 (en) | 2020-04-28 |
| CN107407872A (zh) | 2017-11-28 |
| US20180203349A1 (en) | 2018-07-19 |
| KR101998338B1 (ko) | 2019-10-01 |
| JP2018508824A (ja) | 2018-03-29 |
| CN107407872B (zh) | 2020-08-07 |
| US10409160B2 (en) | 2019-09-10 |
| KR20170117468A (ko) | 2017-10-23 |
| US9952507B2 (en) | 2018-04-24 |
| TWI652281B (zh) | 2019-03-01 |
| US20190369492A1 (en) | 2019-12-05 |
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