KR101012569B1 - 감광성 수지 전구체 조성물 - Google Patents
감광성 수지 전구체 조성물 Download PDFInfo
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- KR101012569B1 KR101012569B1 KR1020030053681A KR20030053681A KR101012569B1 KR 101012569 B1 KR101012569 B1 KR 101012569B1 KR 1020030053681 A KR1020030053681 A KR 1020030053681A KR 20030053681 A KR20030053681 A KR 20030053681A KR 101012569 B1 KR101012569 B1 KR 101012569B1
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- resin precursor
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- 239000002243 precursor Substances 0.000 title claims abstract description 81
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 229920005989 resin Polymers 0.000 title claims abstract description 35
- 239000011347 resin Substances 0.000 title claims abstract description 35
- -1 quinonediazide compound Chemical class 0.000 claims abstract description 112
- 229920000642 polymer Polymers 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000002904 solvent Substances 0.000 claims abstract description 35
- 229920006015 heat resistant resin Polymers 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 230000005855 radiation Effects 0.000 claims abstract description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 6
- 125000000962 organic group Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 150000008065 acid anhydrides Chemical class 0.000 claims description 14
- 150000001805 chlorine compounds Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000007789 sealing Methods 0.000 claims description 9
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 9
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 claims description 7
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 238000005538 encapsulation Methods 0.000 claims description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000004010 onium ions Chemical class 0.000 claims 1
- 125000005490 tosylate group Chemical class 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 31
- 239000011248 coating agent Substances 0.000 abstract description 29
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 38
- 239000002966 varnish Substances 0.000 description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 35
- 229920001721 polyimide Polymers 0.000 description 33
- 239000004642 Polyimide Substances 0.000 description 30
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 26
- 235000012431 wafers Nutrition 0.000 description 26
- 239000002253 acid Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 23
- 229910052710 silicon Inorganic materials 0.000 description 23
- 239000010703 silicon Substances 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 22
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 21
- 239000012528 membrane Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000005259 measurement Methods 0.000 description 17
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 239000013585 weight reducing agent Substances 0.000 description 14
- 150000004985 diamines Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229920005575 poly(amic acid) Polymers 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000001153 fluoro group Chemical group F* 0.000 description 10
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 229940116333 ethyl lactate Drugs 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000013256 coordination polymer Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000036211 photosensitivity Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 5
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 5
- 239000008393 encapsulating agent Substances 0.000 description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229920002577 polybenzoxazole Polymers 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- CFTSORNHIUMCGF-UHFFFAOYSA-N (1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1 CFTSORNHIUMCGF-UHFFFAOYSA-N 0.000 description 4
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical group OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 4
- QNHYFFOMUQQWPR-UHFFFAOYSA-N 2-[1,1,1,3,3,3-hexafluoro-2-(2-hydroxyphenyl)propan-2-yl]phenol Chemical group OC1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1O QNHYFFOMUQQWPR-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 4
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- JXYITCJMBRETQX-UHFFFAOYSA-N 4-ethynylaniline Chemical compound NC1=CC=C(C#C)C=C1 JXYITCJMBRETQX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 4
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 4
- 238000007689 inspection Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 150000000000 tetracarboxylic acids Chemical group 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 3
- TWEVQGUWCLBRMJ-UHFFFAOYSA-N 3-hydroxycyclohexanone Chemical compound OC1CCCC(=O)C1 TWEVQGUWCLBRMJ-UHFFFAOYSA-N 0.000 description 3
- GULNLSGTYCQLLM-UHFFFAOYSA-N 3-hydroxycyclopentan-1-one Chemical compound OC1CCC(=O)C1 GULNLSGTYCQLLM-UHFFFAOYSA-N 0.000 description 3
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DLEPYXFUDLQGDW-UHFFFAOYSA-N FC(F)(F)NC1=CC=C(C2=CC=C(NC(F)(F)F)C=C2)C=C1 Chemical compound FC(F)(F)NC1=CC=C(C2=CC=C(NC(F)(F)F)C=C2)C=C1 DLEPYXFUDLQGDW-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 206010047571 Visual impairment Diseases 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- VKGMUJJGIHYISW-UHFFFAOYSA-N naphthalene-1,5-dione diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1(C=CC=C2C(C=CC=C12)=O)=O VKGMUJJGIHYISW-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000009719 polyimide resin Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- 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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/108—Polyolefin or halogen containing
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
Claims (11)
- (a) 내열성 수지 전구체 중합체, (b) 감방사선성 화합물, (c) 하기 화학식 1a로 표시되는 용제를 함유하며, (a) 내열성 수지 전구체 중합체가 하기 화학식 3 또는 하기 화학식 4로 표시되는 구조 단위를 주성분으로 하는 중합체이며, (b) 감방사선성 화합물이 오늄 화합물, 퀴논디아지드 화합물, 이미드술포네이트 유도체, 토실레이트 화합물, 벤질 유도체의 카르보네이토 화합물 및 트리아진 유도체의 할로겐 화합물에서 선택되는 하나 이상의 화합물이며, (c) 하기 화학식 1a로 표시되는 용제의 함량이 용제 전량의 30 중량% 이상 40 중량% 이하인 것을 특징으로 하는 감광성 수지 전구체 조성물.<화학식 1a>식 중, R1은 탄소수 1 내지 3의 알킬기를 나타내고, R4, R5는 각각 독립적으로 수소 또는 탄소수 1 내지 3의 알킬기를 나타내며,<화학식 3>식 중 R11, R12는 2개 이상의 탄소 원자를 갖는 2가 내지 8가의 유기기이고, R13 , R14는 수소 또는 탄소수 1 내지 20의 유기기 중 어느 하나를 나타내며, n은 10 내지 100000의 범위이고, m, f는 0 내지 2의 정수이며, p, q는 0 내지 4의 정수를 나타내되, 단 p+q>0이며,<화학식 4>식 중, R15는 2개 이상의 탄소 원자를 갖는 2가 내지 8가의 유기기이고, R16은 2개 이상의 탄소 원자를 갖는 2가 내지 6가의 유기기이며, R17은 화학선에 의해 이량화 또는 중합 가능한 탄소-탄소 불포화 이중 결합을 갖는 탄소수 1 내지 30의 유기기를 나타내고, h는 10 내지 100000의 범위이다.
- 제1항에 있어서, (b) 감방사선성 화합물이 퀴논디아지드 화합물인 것을 특징으로 하는 감광성 수지 전구체 조성물.
- 제1항에 있어서, 화학식 3의 m, f, p가 0인 것을 특징으로 하는 감광성 수지 전구체 조성물.
- 제1항에 있어서, 화학식 3의 m이 2이고, f가 1 또는 2인 것을 특징으로 하는 감광성 수지 전구체 조성물.
- 제1항에 있어서, (a) 내열성 수지 전구체 중합체가 하기 화학식 9 내지 16으로 표시되는 구조를 갖는 수지로부터 선택되는 수지인 것을 특징으로 하는 감광성 수지 전구체 조성물.<화학식 9><화학식 10><화학식 11><화학식 12><화학식 13><화학식 14><화학식 15><화학식 16>화학식 9 내지 12 중, R11, R12는 2개 이상의 탄소 원자를 갖는 2가 내지 8가의 유기기이고, R13, R14는 수소 또는 탄소수 1 내지 20의 유기기 중 어느 하나를 나타내며, n은 10 내지 100000의 범위이고, m, f는 0 내지 2의 정수이며, p, q는 0 내지 4의 정수를 나타내되, 단 p+q>0이며,화학식 13 내지 16 중, R15는 2개 이상의 탄소 원자를 갖는 2가 내지 8가의 유기기이고, R16은 2개 이상의 탄소 원자를 갖는 2가 내지 6가의 유기기이며, R17은 화학선에 의해 이량화 또는 중합 가능한 탄소-탄소 불포화 이중 결합을 갖는 탄소수 1 내지 30의 유기기를 나타내고, h는 10 내지 100000의 범위이며,화학식 9 내지 16 중, R31은 -CR32R33-, -CH2O- 및 -CH2SO2-로부터 선택되는 2가의 기를 나타내고, R32, R33은 수소 원자 및 탄소수 1 내지 10의 탄화수소기로부터 선택되는 1가의 기를 나타내며, g는 0 내지 10의 정수이며,X 및 Y는 유기기이고, 화학식 9, 10, 13, 14에서의 -NH-(R31)g-X는 말단 봉지제인 1급 모노아민으로부터 유래하는 성분이며, 화학식 11, 12, 15, 16에서의 -CO-(R31)g-Y는 말단 봉지제인 산 무수물, 모노카르복실산, 모노산 클로라이드 화합물 또는 모노 활성 에스테르 화합물로부터 유래하는 성분이다.
- 삭제
- 삭제
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EP (1) | EP1388758A1 (ko) |
KR (1) | KR101012569B1 (ko) |
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KR101020164B1 (ko) | 2003-07-17 | 2011-03-08 | 허니웰 인터내셔날 인코포레이티드 | 진보된 마이크로전자적 응용을 위한 평탄화 막, 및 이를제조하기 위한 장치 및 방법 |
US7211728B2 (en) * | 2004-08-17 | 2007-05-01 | Jds Uniphase Corporation | Optical cage system preventing insertion of incorrect module |
EP1662322B1 (en) * | 2004-11-26 | 2017-01-11 | Toray Industries, Inc. | Positive type photo-sensitive siloxane composition, curing film formed by the composition and device with the curing film |
JP2006206756A (ja) * | 2005-01-28 | 2006-08-10 | Sony Chem Corp | ポリイミド化合物及びフレキシブル配線板 |
CN101253449A (zh) * | 2005-08-30 | 2008-08-27 | 日立化成工业株式会社 | 感光性树脂组合物及感光性组件 |
KR100944135B1 (ko) * | 2005-09-05 | 2010-02-24 | 아사히 가세이 이-매터리얼즈 가부시키가이샤 | 포지티브형 감광성 수지 조성물 |
TWI407255B (zh) * | 2005-09-22 | 2013-09-01 | Hitachi Chem Dupont Microsys | 負片型感光性樹脂組成物、圖案形成方法以及電子零件 |
KR101438857B1 (ko) * | 2007-03-12 | 2014-09-05 | 히다치 가세이듀퐁 마이쿠로시스데무즈 가부시키가이샤 | 감광성 수지 조성물, 그 수지 조성물을 이용한 패턴 경화막의 제조방법 및 전자부품 |
JP5061792B2 (ja) * | 2007-08-21 | 2012-10-31 | 住友ベークライト株式会社 | ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置。 |
JP5176872B2 (ja) * | 2007-10-29 | 2013-04-03 | 日立化成デュポンマイクロシステムズ株式会社 | ポジ型感光性樹脂組成物、パタ−ンの製造方法及び電子部品 |
CN101770169B (zh) * | 2008-12-30 | 2012-03-21 | 乐凯集团第二胶片厂 | 一种高分辨力高感光度的阳图平印版感光组合物 |
JP5796712B2 (ja) * | 2009-04-23 | 2015-10-21 | 日産化学工業株式会社 | ポリヒドロキシイミドの製造方法 |
KR20120066924A (ko) * | 2010-12-15 | 2012-06-25 | 제일모직주식회사 | 오르토-니트로벤질 에스테르 화합물 및 이를 포함하는 포지티브형 감광성 수지 조성물 |
CN113820920B (zh) | 2016-03-31 | 2023-07-04 | 旭化成株式会社 | 感光性树脂组合物、固化浮雕图案的制造方法和半导体装置 |
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CN112409998B (zh) * | 2020-11-26 | 2021-10-29 | 汕头大学 | 一种含有n,n,n,n-四甲基对苯二胺的光热转化共晶材料及其制备方法 |
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- 2003-08-04 KR KR1020030053681A patent/KR101012569B1/ko active IP Right Grant
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CN1267501C (zh) | 2006-08-02 |
TWI310396B (en) | 2009-06-01 |
KR20040014249A (ko) | 2004-02-14 |
US20040053156A1 (en) | 2004-03-18 |
US6887643B2 (en) | 2005-05-03 |
EP1388758A1 (en) | 2004-02-11 |
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