TWI652281B - 含有光產鹼劑的光可成像聚烯烴組成物 - Google Patents
含有光產鹼劑的光可成像聚烯烴組成物 Download PDFInfo
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- TWI652281B TWI652281B TW105103252A TW105103252A TWI652281B TW I652281 B TWI652281 B TW I652281B TW 105103252 A TW105103252 A TW 105103252A TW 105103252 A TW105103252 A TW 105103252A TW I652281 B TWI652281 B TW I652281B
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- 239000000203 mixture Substances 0.000 title claims abstract description 144
- 229920000098 polyolefin Polymers 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 103
- 238000004377 microelectronic Methods 0.000 claims abstract description 11
- 230000005693 optoelectronics Effects 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 58
- -1 norbornenyl propionic acid Chemical compound 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 35
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000654 additive Substances 0.000 claims description 17
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000004593 Epoxy Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- NIQLOLNJWXWZHX-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1C2C(CC(O)(C(F)(F)F)C(F)(F)F)CC1C=C2 NIQLOLNJWXWZHX-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 4
- RYYYTOGKTKBJDJ-UHFFFAOYSA-N 2-(3-benzylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(CC=2C=CC=CC=2)=C1 RYYYTOGKTKBJDJ-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
- ZSRIIBBLZOXFPK-UHFFFAOYSA-N 5-(3-methoxypropoxy)-1-methylbicyclo[2.2.1]hept-2-ene Chemical compound COCCCOC1C2C=CC(C1)(C2)C ZSRIIBBLZOXFPK-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 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 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- OQQXGCLLMDQESN-UHFFFAOYSA-N cyclohexylcarbamic acid Chemical compound OC(=O)NC1CCCCC1 OQQXGCLLMDQESN-UHFFFAOYSA-N 0.000 claims 1
- ZILRSGXFDURMQD-UHFFFAOYSA-N ethyl 3-(3-bicyclo[2.2.1]hept-2-enyl)propanoate Chemical compound C1CC2C(CCC(=O)OCC)=CC1C2 ZILRSGXFDURMQD-UHFFFAOYSA-N 0.000 claims 1
- 230000000930 thermomechanical effect Effects 0.000 abstract description 9
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 40
- 239000010410 layer Substances 0.000 description 36
- 235000012431 wafers Nutrition 0.000 description 32
- 238000000034 method Methods 0.000 description 31
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 22
- 238000000576 coating method Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 239000011248 coating agent Substances 0.000 description 19
- 239000000758 substrate Substances 0.000 description 19
- 238000011161 development Methods 0.000 description 18
- 230000005855 radiation Effects 0.000 description 18
- 230000014509 gene expression Effects 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000004065 semiconductor Substances 0.000 description 15
- 229910052814 silicon oxide Inorganic materials 0.000 description 15
- 238000004090 dissolution Methods 0.000 description 14
- 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 13
- 229920001577 copolymer Polymers 0.000 description 13
- 238000003384 imaging method Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 238000001878 scanning electron micrograph Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 238000000879 optical micrograph Methods 0.000 description 7
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 239000002861 polymer material Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229920001774 Perfluoroether Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 239000003513 alkali Substances 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
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 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
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010073306 Exposure to radiation Diseases 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
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 238000012644 addition polymerization Methods 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 230000000712 assembly Effects 0.000 description 3
- 238000000429 assembly Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001747 exhibiting 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
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000411 inducer Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 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
- 238000002161 passivation Methods 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 2
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-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
- ZJJWOHVTXHKFAP-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoate 2,3,4,5,6,7,8,9-octahydropyrimido[1,2-a]pyrimidin-5-ium Chemical compound C1CNC2=NCCC[NH+]2C1.CC(C([O-])=O)c1cccc(c1)C(=O)c1ccccc1 ZJJWOHVTXHKFAP-UHFFFAOYSA-N 0.000 description 2
- OPRBIXRROSYFNV-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enyl)oxirane Chemical compound C1OC1C1C(C=C2)CC2C1 OPRBIXRROSYFNV-UHFFFAOYSA-N 0.000 description 2
- GBNPJBBNCBLPQT-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enylmethoxymethyl)oxirane Chemical compound C1C(C=C2)CC2C1COCC1CO1 GBNPJBBNCBLPQT-UHFFFAOYSA-N 0.000 description 2
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 2
- FJGYVBYNJSSXOE-UHFFFAOYSA-N 2-[[2-hydroxy-3-[(4-hydroxy-3-methylphenyl)methyl]-5-methylphenyl]methyl]-6-[(4-hydroxy-3-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(CC=2C(=C(CC=3C=C(C)C(O)=CC=3)C=C(C)C=2)O)=CC(C)=CC=1CC1=CC=C(O)C(C)=C1 FJGYVBYNJSSXOE-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
- 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
- UDOJACSDSIHAAT-UHFFFAOYSA-N 5-benzylbicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CC1=CC=CC=C1 UDOJACSDSIHAAT-UHFFFAOYSA-N 0.000 description 2
- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 description 2
- GOLQZWYZZWIBCA-UHFFFAOYSA-N 5-octylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCC)CC1C=C2 GOLQZWYZZWIBCA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-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
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- 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)
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| US201562117774P | 2015-02-18 | 2015-02-18 | |
| US62/117,774 | 2015-02-18 |
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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 |
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| US20180203349A1 (en) | 2018-07-19 |
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| 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 |
| US20190369492A1 (en) | 2019-12-05 |
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