WO2023162489A1 - Composition de résine - Google Patents
Composition de résine Download PDFInfo
- Publication number
- WO2023162489A1 WO2023162489A1 PCT/JP2023/000323 JP2023000323W WO2023162489A1 WO 2023162489 A1 WO2023162489 A1 WO 2023162489A1 JP 2023000323 W JP2023000323 W JP 2023000323W WO 2023162489 A1 WO2023162489 A1 WO 2023162489A1
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- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- structural unit
- component
- group
- unit represented
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 72
- 229920005989 resin Polymers 0.000 claims abstract description 40
- 239000011347 resin Substances 0.000 claims abstract description 40
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 238000009835 boiling Methods 0.000 claims abstract description 10
- 238000002844 melting Methods 0.000 claims abstract description 10
- 230000008018 melting Effects 0.000 claims abstract description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 24
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 claims description 14
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 12
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 8
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 6
- 229940116333 ethyl lactate Drugs 0.000 claims description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 5
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 claims description 5
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 4
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 4
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 claims description 4
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- 229940117360 ethyl pyruvate Drugs 0.000 claims description 4
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 claims description 4
- 229940017144 n-butyl lactate Drugs 0.000 claims description 4
- 239000000126 substance Substances 0.000 abstract description 16
- 238000001312 dry etching Methods 0.000 abstract description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- -1 aromatic halogen compound Chemical class 0.000 description 23
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000011156 evaluation Methods 0.000 description 21
- 235000012431 wafers Nutrition 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- 229910052710 silicon Inorganic materials 0.000 description 11
- 239000010703 silicon Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 4
- 239000004734 Polyphenylene sulfide Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229920000069 polyphenylene sulfide Polymers 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 description 3
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- USHOSLIEBCEAIY-UHFFFAOYSA-N 1-methoxy-2-[(2-methoxyphenyl)disulfanyl]benzene Chemical compound COC1=CC=CC=C1SSC1=CC=CC=C1OC USHOSLIEBCEAIY-UHFFFAOYSA-N 0.000 description 2
- HIGGFWFRAWSMBR-UHFFFAOYSA-N 2-Methyl-3-hexanone Chemical compound CCCC(=O)C(C)C HIGGFWFRAWSMBR-UHFFFAOYSA-N 0.000 description 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- GYWYASONLSQZBB-UHFFFAOYSA-N 3-methylhexan-2-one Chemical compound CCCC(C)C(C)=O GYWYASONLSQZBB-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- ZCZSIDMEHXZRLG-UHFFFAOYSA-N Heptyl acetate Chemical compound CCCCCCCOC(C)=O ZCZSIDMEHXZRLG-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RGFNRWTWDWVHDD-UHFFFAOYSA-N isobutyl butyrate Chemical compound CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 235000019337 sorbitan trioleate Nutrition 0.000 description 2
- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000019086 sulfide ion homeostasis Effects 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-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
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 1
- KVWOTUDBCFBGFJ-UHFFFAOYSA-N tert-butyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C KVWOTUDBCFBGFJ-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- TWBUVVYSQBFVGZ-UHFFFAOYSA-N tert-butyl butanoate Chemical compound CCCC(=O)OC(C)(C)C TWBUVVYSQBFVGZ-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B3/00—Simple or compound lenses
Definitions
- the present invention relates to a resin composition, a resin film obtained from the resin composition, an optical member, and a microlens.
- optical members such as intralayer lenses, optical waveguides, and film substrates.
- optical members are required to have not only transparency but also long-term reliability such as excellent heat resistance, light resistance, and moisture resistance, and chemical resistance.
- the optical member is often required to have a high refractive index in order to improve the light extraction efficiency and the light condensing property.
- an etch-back method is known as one method of manufacturing microlenses for CCD/CMOS image sensors (Patent Documents 1 and 2). That is, a resist pattern is formed on the microlens resin layer formed on the color filter layer, and the resist pattern is reflowed by heat treatment to form a lens pattern. Using the lens pattern formed by reflowing this resist pattern as an etching mask, the underlying microlens resin layer is etched back, and the lens pattern shape is transferred to the microlens resin layer to fabricate the microlens.
- the microlens manufacturing by the etch-back method is generally performed on the wafer, materials suitable for the wafer process, such as EBR (edge bead removal or edge bead rinse) performed for the purpose of preventing contamination of the wafer transfer arm, are used.
- EBR edge bead removal or edge bead rinse
- the present invention has been made based on the above circumstances, and is capable of EBR, and has a high refractive index, transparency, heat resistance, light resistance, moisture resistance, chemical resistance, and a dry etching rate equivalent to that of resist. It aims at providing the resin composition which can form the resin film which has.
- the inventors of the present invention have made intensive studies to solve the above problems, and found that a composition containing polyphenylene sulfide having a phenolic hydroxy group and a specific organic solvent can solve the above problems. completed.
- the present invention provides the following resin composition.
- (A) a polymer and (B) an organic solvent The component (A) is a polymer containing a structural unit represented by the following formula (1), A resin composition in which the component (B) is an organic solvent having a melting point of 15°C or lower and a boiling point of 85°C or higher.
- R 1 independently represents a hydroxy group, methyl group, ethyl group, methoxy group or ethoxy group
- a represents an integer of 0 to 3
- n represents an integer of 1 to 4;
- the above a and n satisfy 1 ⁇ a + n ⁇ 4.
- the component (A) is a structural unit represented by the following formula (3a), a structural unit represented by the following formula (3b), a structural unit represented by the following formula (4a), and a structural unit represented by the following formula (4b).
- 1 or 2 resin composition which is a polymer containing at least one structural unit selected from the group consisting of structural units. 4.
- the component (B) is ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol mono Ethyl ether acetate, propylene glycol monomethyl ether acetate, ethyl lactate, n-butyl lactate, methyl pyruvate, ethyl pyruvate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 2-heptanone, cyclopenta Any of 1 to 3 containing at least one organic solvent selected from the group consisting of non, cyclohexanone, ⁇ -butyrolactone, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and N-ethyl-2-pyrroli
- the present invention by dissolving polyphenylene sulfide having a phenolic hydroxyl group in a specific organic solvent, EBR becomes possible, and the formed resin film exhibits a high refractive index and high transparency, and long-term reliability and It is possible to provide a resin composition suitable for use in optical members, which is also excellent in chemical resistance. Moreover, since the resin film has an appropriate dry etching rate, it is particularly suitable for microlens applications.
- the resin composition of the present invention will be described in more detail below.
- the resin composition of the present invention is characterized by containing (A) a polymer and (B) an organic solvent, which will be described later.
- solid content means components other than the solvent which comprise a resin composition.
- the polymer is not particularly limited as long as it contains a structural unit represented by the following formula (1).
- each R 1 independently represents a hydroxy group, a methyl group, an ethyl group, a methoxy group or an ethoxy group, a represents an integer of 0 to 3, and n represents an integer of 1 to 4. .
- a and n satisfy 1 ⁇ a+n ⁇ 4.
- R 1 is preferably a hydroxy group.
- the a is preferably 0 or 1, and the n is preferably 1.
- a structural unit represented by the following formula (2) is preferable as the structural unit represented by the formula (1).
- R 1 has the same definition as in formula (1) above.
- the structural unit represented by the formula (1) include a structural unit represented by the following formula (3a), a structural unit represented by the following formula (3b), and a structural unit represented by the following formula (4a).
- Structural units and structural units represented by the following formula (4b) are included.
- component (A) may contain other structural units other than the structural unit represented by the formula (1) as long as the effects of the present invention are not impaired.
- Other structural units include, for example, structural units represented by the following formula (a) and structural units represented by the following formula (b).
- n an integer of 1 to 4.
- the proportion of the structural unit represented by formula (1) in the polymer is preferably 10 mol% or more, more preferably 20 mol% or more, still more preferably 30 mol% or more, and still more preferably 50 mol%. This is the above, and 100 mol % is optimal.
- the molecular weight of the polymer is preferably 500 to 100,000, more preferably 1,000 to 30,000, and still more preferably 1,500 as a polystyrene equivalent weight average molecular weight calculated by gel permeation chromatography (GPC). ⁇ 10,000.
- polyarylene sulfide production methods polycondensation with an aromatic halogen compound and sodium sulfide, oxidation polymerization of an aromatic thiol compound or an aromatic disulfide compound, etc.
- polycondensation with an aromatic halogen compound and sodium sulfide, oxidation polymerization of an aromatic thiol compound or an aromatic disulfide compound, etc. are applied to a phenol derivative.
- various known polyarylene sulfide production methods polycondensation with an aromatic halogen compound and sodium sulfide, oxidation polymerization of an aromatic thiol compound or an aromatic disulfide compound, etc.
- it can be synthesized by deprotecting some or all of the protecting groups.
- the oxidative polymerization method using a quinone-based oxidizing agent and an acid described in Patent Documents 4 and 5 is preferably used.
- Specific production methods thereof include a method of oxidative polymerization using a quinone-based oxidizing agent and an acid using an aromatic thiol compound containing a hydroxy group or an aromatic disulfide compound containing a hydroxy group as a monomer; An aromatic thiol compound containing a hydroxy group or an aromatic disulfide compound containing a protected hydroxy group is used as a monomer and oxidatively polymerized using a quinone-based oxidizing agent and an acid, and then some or all of the protective groups are deprotected.
- the protected hydroxy group is not particularly limited as long as the polymerization proceeds, but from the viewpoint of stability that does not interfere with a quinone-based oxidizing agent or acid, an alkoxy group is preferred, a methoxy group or an ethoxy group is more preferred, and a methoxy group is preferred. , is particularly preferred because the deprotection reaction can proceed more easily.
- the alkoxy group can be converted to a hydroxy group by removing the alkyl group by the action of an acid or the like.
- the acid examples include Lewis acids such as trisubstituted boron compounds (such as boron tribromide) and aluminum chloride, and Bronsted acids such as thiol compounds (such as dodecanethiol) and hydrogen bromide. It is not particularly limited as long as it is a convertible acid. All protecting groups may be deprotected or some may be left. Optical properties and solubility can be controlled by appropriately adjusting the deprotection rate.
- Lewis acids such as trisubstituted boron compounds (such as boron tribromide) and aluminum chloride
- Bronsted acids such as thiol compounds (such as dodecanethiol) and hydrogen bromide. It is not particularly limited as long as it is a convertible acid. All protecting groups may be deprotected or some may be left. Optical properties and solubility can be controlled by appropriately adjusting the deprotection rate.
- the monomers used to synthesize the component (A) may be used singly or in combination of two or more. From the viewpoint of adjusting optical properties and solubility, if necessary, an aromatic thiol compound or aromatic disulfide compound containing no hydroxy group, or an aromatic thiol compound or aromatic disulfide containing no protected hydroxy group.
- the compound may be polymerized using the compound as a comonomer. That is, the polymer may contain at least one structural unit represented by the formula (1), and may be a homopolymer or a copolymer.
- the polymer is a copolymer
- its repeating structure is not particularly limited, and may be an alternating copolymer, a block copolymer, a gradient copolymer or a random copolymer.
- the polymer may be branched depending on the polymerization conditions.
- the organic solvent is an organic solvent having a melting point of 15° C. or lower and a boiling point of 85° C. or higher.
- the melting point and boiling point refer to those at 1 atmospheric pressure. Since the melting point is 15° C. or lower, the resin composition has excellent handleability at room temperature.
- the melting point is preferably 10° C. or lower, more preferably 5° C. or lower, from the viewpoint of storability in a cold place.
- the lower limit of the melting point is not particularly limited, but is preferably -150° C. or higher, for example.
- the boiling point is 85° C. or higher, the coating film formed by coating the resin composition on a substrate is less likely to whiten.
- the boiling point is preferably 100° C. or higher, more preferably 115° C. or higher, from the viewpoint of facilitating the formation of a uniform coating film.
- the upper limit of the boiling point is preferably 300° C. or lower, more preferably 250° C. or lower, and even more preferably 220° C. or lower, from the viewpoint of organic solvent removability.
- component (B) include methylcyclohexane, ethylcyclohexane, n-heptane, toluene, o-xylene, m-xylene, mesitylene, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, anisole, phenetol, di- n-propyl ether, di-n-butyl ether, diisobutyl ether, di-n-pentyl ether, diisopentyl ether, di-n-hexyl ether, n-butyl ethyl ether, methyl-n-pentyl ether, cyclopentyl methyl ether, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, 1-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-p
- the component (B) includes ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, and propylene from the viewpoint of improving the leveling properties of the coating film formed by coating the resin composition on a substrate.
- the component (B) may be used singly or in combination of two or more. In addition, it may be appropriately mixed with a solvent other than the component (B).In that case, the content of the component (B) is preferably 50 to 100% by mass of the total solvent including the component (B) and other solvents. More preferably 60 to 100% by mass, still more preferably 70 to 100% by mass.
- the other solvents include methanol, ethanol, 2-propanol, dichloromethane, 1,2-dichloroethane, chloroform, acetone, 2-butanone, dimethylsulfoxide (DMSO), tetrahydrofuran, ethyl acetate, and acetonitrile. mentioned.
- the resin composition of the present invention may further contain (C) a polyfunctional epoxy compound for the purpose of improving chemical resistance.
- the component (C) is not particularly limited as long as it is a compound having at least two oxirane rings in the molecule.
- the following products and compounds can be used.
- TEPIC (registered trademark)-G, -L, -VL, -S, -SP, -SS, -HP (manufactured by Nissan Chemical Co., Ltd.), Marproof (registered trademark) G- 01100, G-0105SA, G-0130SF, G-0130SP, G-0150M, G-0250SF, G-0250SP, G-05100, G-2050M, G-017581 (above, Japan Oil Co., Ltd.), OGSOL (registered trademark) PG-100, CG-500, EG-200, EG-280 (manufactured by Osaka Gas Chemicals Co., Ltd.), GTR-1800 (manufactured by Nippon Kagaku Pharmaceutical Co., Ltd.), EPICLON (registered trademark) 830, 830-S, 835, 840, 840-S, 850, 850-S, 850-LC, HP-820 (above, DIC Corporation), DENACOL (registered trademark
- the (C) component may be used singly or in combination of two or more.
- the content of component (C) is preferably 5 to 50 parts by mass, more preferably 10 to 30 parts by mass, per 100 parts by mass of component (A). Department.
- the resin composition of the present invention may optionally contain a surfactant for the purpose of improving coatability.
- surfactants include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether; polyoxyethylene octylphenyl ether and polyoxyethylene polyoxyethylene alkylaryl ethers such as nonylphenyl ether; polyoxyethylene/polyoxypropylene block copolymers; sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan trioleate; Sorbitan fatty acid esters such as stearates; Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters; , F-173, R-30, R-40, R-40-LM (manufactured by stearates.
- the content of the surfactant is preferably 0.001 to 3 parts by mass, more preferably 0.005 to 1 part by mass, relative to 100 parts by mass of the total solid content. parts, more preferably 0.01 to 0.5 parts by weight.
- the resin composition of the present invention may optionally contain a curing aid, an antioxidant, a light stabilizer (HALS), an ultraviolet absorber, a plasticizer, an adhesion aid, and the like. Agents can be further included.
- a curing aid an antioxidant, a light stabilizer (HALS), an ultraviolet absorber, a plasticizer, an adhesion aid, and the like.
- HALS light stabilizer
- Agents can be further included.
- the method for preparing the resin composition of the present invention is not particularly limited, but examples thereof include a method of mixing components (A) and (B), and optionally component (C) and other components to form a uniform solution. be done. Moreover, if necessary, the obtained solution may be filtered using a filter with a pore size of 0.1 to 10 ⁇ m.
- the solid content concentration of the resin composition thus obtained is usually 1 to 50% by mass from the viewpoint of coatability on substrates.
- a substrate for example, a PET film, a TAC film, a semiconductor substrate, a glass substrate, a quartz substrate, a silicon wafer, and a substrate having various metal films or color filters formed thereon
- an appropriate spinner or coater After applying the resin composition of the present invention by a coating method, a resin film is produced by baking using a heating means such as a hot plate or an oven. Baking conditions are appropriately selected from a baking temperature of 50 to 300° C. and a baking time of 0.1 to 360 minutes. The baking process for producing the resin film may be performed in two or more steps.
- the film thickness of the resin film to be formed is 0.001 to 1,000 ⁇ m, preferably 0.01 to 100 ⁇ m, more preferably 0.1 to 10 ⁇ m.
- a resist is applied onto the resin film produced through the above [Method for producing a resin film], the resist is exposed through a predetermined mask, post-exposure baking (PEB) is performed as necessary, alkali development is performed, A resist pattern is formed on the resin film by rinsing and drying.
- PEB post-exposure baking
- the resist pattern is reflowed by heat treatment to form a lens pattern.
- the resin film under the lens pattern is etched back, and the shape of the lens pattern is transferred to the resin film to form a microlens.
- the precipitate generated by the dropping is collected, washed with ethanol, methanol, an aqueous potassium hydroxide solution having a concentration of 3% by mass, and pure water in this order, and then dried at 80° C. under reduced pressure to obtain the following formula (6). 4 g of polymer containing the represented structural unit was obtained (yield 72%). The polystyrene-equivalent weight average molecular weight Mw of the obtained polymer was 3,000.
- the precipitate generated by the dropping is collected, washed with ethanol, methanol, an aqueous potassium hydroxide solution having a concentration of 3% by mass, and pure water in that order, and then dried at 80° C. under reduced pressure to obtain the following formula (8).
- 3.5 g of a copolymer containing the two types of structural units represented was obtained (yield 74%).
- the polystyrene-equivalent weight average molecular weight Mw of the obtained copolymer was 2,500.
- the precipitate generated by the dropping is collected, washed with ethanol, methanol, an aqueous potassium hydroxide solution having a concentration of 3% by mass, and pure water in this order, and then dried at 80° C. under reduced pressure to obtain the following formula (11). 1.8 g of a copolymer containing the two types of structural units represented was obtained (yield 33%).
- the polystyrene-equivalent weight average molecular weight Mw of the obtained copolymer was 6,300.
- Example 2 A resin composition (solid concentration: 18% by mass) was obtained in the same manner as in Example 1, except that 9.8 g of ⁇ -butyrolactone and 6.6 g of methyl pyruvate were used as the component (B).
- Example 3 A resin composition (solid concentration: 18% by mass) was obtained in the same manner as in Example 1, except that 8.2 g of ethyl lactate and 8.2 g of ethyl 3-ethoxypropionate were used as the component (B). Ta.
- Example 4 A resin composition (solid content concentration 18 mass% ).
- Example 5 A resin composition (solid concentration: 18% by mass) was obtained in the same manner as in Example 1, except that 16.4 g of cyclopentanone was used as the component (B).
- Example 6 Example 1 except that 20.5 g of cyclopentanone was used as component (B) and 0.9 g of ethylene glycol diglycidyl ether was used as component (C) (25 parts by mass per 100 parts by mass of component (A)). A resin composition (solid concentration: 18% by mass) was obtained in the same manner.
- Example 7 Same as Example 1 except that 23.0 g of cyclopentanone was used as component (B) and 1.4 g of resorcinol diglycidyl ether was used as component (C) (40 parts by mass per 100 parts by mass of component (A)). A resin composition (solid content concentration 18% by mass) was obtained by the procedure of.
- Example 8 Same as Example 1 except that 19.7 g of cyclopentanone was used as component (B) and 0.7 g of triglycidyl isocyanurate was used as component (C) (20 parts by mass per 100 parts by mass of component (A)). A resin composition (solid content concentration 18% by mass) was obtained by the procedure of.
- Example 9 A resin composition (solid concentration: 18% by mass) was obtained in the same manner as in Example 5, except that the surfactant was not included.
- Example 10 A resin composition was prepared in the same manner as in Example 1 except that 3.6 g of the copolymer obtained in Synthesis Example 4 was used as the component (A) and 16.4 g of cyclopentanone was used as the component (B). (solid content concentration 18% by mass) was obtained.
- Example 11 A resin composition was prepared in the same manner as in Example 1 except that 3.0 g of the copolymer obtained in Synthesis Example 6 was used as the component (A) and 17.0 g of cyclopentanone was used as the component (B). (solid content concentration 15% by mass) was obtained.
- Example 1 The procedure of Example 1 was repeated except that 3.6 g of the polymer obtained in Synthesis Example 1 was used as the polymer not corresponding to component (A), and 16.4 g of cyclopentanone was used as component (B). , to obtain a resin composition (solid concentration: 18% by mass).
- ⁇ Comparative Example 4> 3.6 g of the polymer obtained in Synthesis Example 2 was used as component (A), and 16.4 g of dimethyl sulfoxide (melting point: 18°C, boiling point: 189°C) was used as an organic solvent that did not correspond to component (B). A resin composition (solid concentration: 18% by mass) was obtained in the same procedure as in Example 1. When the obtained resin composition was stored in a refrigerator with an interior temperature of 5° C., it solidified.
- a resist solution THMR-iP1800 (manufactured by Tokyo Ohka Kogyo Co., Ltd.) is applied onto a silicon wafer using a spin coater, and placed on a hot plate at 90°C for 1.5 minutes, 110°C for 1.5 minutes, and then at 180°C. C. for 1 minute to form a resist film with a thickness of 1 .mu.m.
- the resist film was dry etched using a dry etching apparatus RIE-10NR (manufactured by Samco Ltd.) (etching gas: CF 4 ), and the dry etching rate of the resist film was measured.
- each of the resin compositions prepared in Examples 1 to 11 was applied onto a silicon wafer using a spin coater and baked on a hot plate at 100° C. for 1 minute. Thereafter, Examples 1 to 4 were baked at 260° C. for 5 minutes, and Examples 5 to 11 were baked at 200° C. for 5 minutes to form a resin film having a thickness of 1 ⁇ m, and the dry etching rate was similarly measured. Then, the dry etching rate ratio of the resin films obtained from the resin compositions prepared in Examples 1 to 11 to the resist film was calculated. Table 1 shows the results.
- the resin composition of the present invention can be subjected to EBR using PGMEA, and nevertheless, the resin film obtained after baking has resistance to PGMEA.
- component (C) further improved chemical resistance (Examples 6 to 8).
- the resin film exhibited excellent transparency, heat resistance, light resistance and moisture resistance while having a high refractive index of 1.75 or more. Furthermore, it was confirmed that the resin film has a dry etching rate suitable for the etch-back method and that it is possible to fabricate a microlens.
- Comparative Examples 1 and 2 in which polyphenylene sulfide having no phenolic hydroxy group was used instead of component (A), EBR was not possible, and the refractive index of the resulting resin film was less than 1.75. Met. In addition, even if the component (C) was added, no chemical resistance improvement effect was observed (Comparative Example 2).
- the resin composition of the present invention can be used as an optical member such as a protective film, a planarizing film, an insulating film, an antireflection film, a refractive index control film, a microlens, an intralayer lens, an optical waveguide, and a film substrate. It is useful as a resin composition for forming.
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyethers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
La présente invention concerne une composition de résine à partir de laquelle il est possible de constituer un film de résine pouvant subir un traitement EBR, présentant un indice de réfraction, une transparence, une résistance à la chaleur, une résistance à la lumière, une résistance à l'humidité et une résistance chimique élevés, ainsi qu'une vitesse de gravure à sec comparable à celle d'une réserve. La composition de résine contient (A) un polymère et (B) un solvant organique. Le composant (A) est un polymère comprenant un motif structural de formule (1). Le composant (B) est un solvant organique présentant un point de fusion de 15 °C ou moins et un point d'ébullition de 85 °C ou plus. (Dans la formule, chaque R1 représente indépendamment un groupe hydroxy, un groupe méthyle, un groupe éthyle, un groupe méthoxy ou un groupe éthoxy, a représente un nombre entier de 0 à 3 et n représente un nombre entier de 1 à 4. Cependant, a et n satisfont 1 ≤ a + n ≤ 4).
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CN202380022645.2A CN118742607A (zh) | 2022-02-22 | 2023-01-10 | 树脂组合物 |
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JP2022025906 | 2022-02-22 | ||
JP2022-025906 | 2022-02-22 | ||
JP2022158355 | 2022-09-30 | ||
JP2022-158355 | 2022-09-30 |
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WO2023162489A1 true WO2023162489A1 (fr) | 2023-08-31 |
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PCT/JP2023/000323 WO2023162489A1 (fr) | 2022-02-22 | 2023-01-10 | Composition de résine |
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TW (1) | TW202346418A (fr) |
WO (1) | WO2023162489A1 (fr) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52104550A (en) * | 1976-02-28 | 1977-09-02 | Bridgestone Corp | Compositions for rapid adhesion |
JPH08511050A (ja) * | 1993-06-14 | 1996-11-19 | アクゾ ノーベル ナムローゼ フェンノートシャップ | 加硫ゴム組成物中のスルフィド樹脂 |
JP2011162602A (ja) * | 2010-02-05 | 2011-08-25 | Taoka Chem Co Ltd | 新規サルファイド樹脂 |
JP2014084380A (ja) * | 2012-10-22 | 2014-05-12 | Sumitomo Rubber Ind Ltd | インナーライナージョイントストリップ用ゴム組成物及び空気入りタイヤ |
-
2023
- 2023-01-10 WO PCT/JP2023/000323 patent/WO2023162489A1/fr active Application Filing
- 2023-01-31 TW TW112103234A patent/TW202346418A/zh unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52104550A (en) * | 1976-02-28 | 1977-09-02 | Bridgestone Corp | Compositions for rapid adhesion |
JPH08511050A (ja) * | 1993-06-14 | 1996-11-19 | アクゾ ノーベル ナムローゼ フェンノートシャップ | 加硫ゴム組成物中のスルフィド樹脂 |
JP2011162602A (ja) * | 2010-02-05 | 2011-08-25 | Taoka Chem Co Ltd | 新規サルファイド樹脂 |
JP2014084380A (ja) * | 2012-10-22 | 2014-05-12 | Sumitomo Rubber Ind Ltd | インナーライナージョイントストリップ用ゴム組成物及び空気入りタイヤ |
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TW202346418A (zh) | 2023-12-01 |
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