JP6459191B2 - 感光性樹脂組成物 - Google Patents
感光性樹脂組成物 Download PDFInfo
- Publication number
- JP6459191B2 JP6459191B2 JP2014055952A JP2014055952A JP6459191B2 JP 6459191 B2 JP6459191 B2 JP 6459191B2 JP 2014055952 A JP2014055952 A JP 2014055952A JP 2014055952 A JP2014055952 A JP 2014055952A JP 6459191 B2 JP6459191 B2 JP 6459191B2
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- JP
- Japan
- Prior art keywords
- photosensitive resin
- general formula
- acid
- resin composition
- aminonaphthalene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims description 54
- -1 quinonediazide compound Chemical class 0.000 claims description 59
- 229920005989 resin Polymers 0.000 claims description 53
- 239000011347 resin Substances 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000003431 cross linking reagent Substances 0.000 claims description 20
- 125000000962 organic group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 229920006015 heat resistant resin Polymers 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000010408 film Substances 0.000 description 66
- 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 29
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 27
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 26
- 230000035945 sensitivity Effects 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000002966 varnish Substances 0.000 description 17
- 238000009835 boiling Methods 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000002243 precursor Substances 0.000 description 14
- 229920001721 polyimide Polymers 0.000 description 13
- 239000004642 Polyimide Substances 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 150000001805 chlorine compounds Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 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 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000011229 interlayer Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 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 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-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
- 239000007787 solid Substances 0.000 description 4
- 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 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-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
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 229920002577 polybenzoxazole Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- HCBNHPOQPCHHMA-UHFFFAOYSA-N 3,4-diethynylaniline Chemical compound NC1=CC=C(C#C)C(C#C)=C1 HCBNHPOQPCHHMA-UHFFFAOYSA-N 0.000 description 2
- UZSIKPMYGUPSKG-UHFFFAOYSA-N 3,4-diethynylbenzoic acid Chemical compound OC(=O)C1=CC=C(C#C)C(C#C)=C1 UZSIKPMYGUPSKG-UHFFFAOYSA-N 0.000 description 2
- XRGBJBOYNHXWPA-UHFFFAOYSA-N 3,5-diethynylaniline Chemical compound NC1=CC(C#C)=CC(C#C)=C1 XRGBJBOYNHXWPA-UHFFFAOYSA-N 0.000 description 2
- KUZBIUTZPWIHSI-UHFFFAOYSA-N 3,5-diethynylbenzoic acid Chemical compound OC(=O)C1=CC(C#C)=CC(C#C)=C1 KUZBIUTZPWIHSI-UHFFFAOYSA-N 0.000 description 2
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 2
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 2
- UCFMKTNJZCYBBJ-UHFFFAOYSA-N 3-[1-(2,3-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)C1=CC=CC(C(O)=O)=C1C(O)=O UCFMKTNJZCYBBJ-UHFFFAOYSA-N 0.000 description 2
- PAHZZOIHRHCHTH-UHFFFAOYSA-N 3-[2-(2,3-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)(C)C1=CC=CC(C(O)=O)=C1C(O)=O PAHZZOIHRHCHTH-UHFFFAOYSA-N 0.000 description 2
- GIMFLOOKFCUUOQ-UHFFFAOYSA-N 3-amino-4-hydroxy-1,2-dihydropyrimidin-6-one Chemical compound NN1CN=C(O)C=C1O GIMFLOOKFCUUOQ-UHFFFAOYSA-N 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- KFFUEVDMVNIOHA-UHFFFAOYSA-N 3-aminobenzenethiol Chemical compound NC1=CC=CC(S)=C1 KFFUEVDMVNIOHA-UHFFFAOYSA-N 0.000 description 2
- NNKQLUVBPJEUOR-UHFFFAOYSA-N 3-ethynylaniline Chemical compound NC1=CC=CC(C#C)=C1 NNKQLUVBPJEUOR-UHFFFAOYSA-N 0.000 description 2
- MNUOZFHYBCRUOD-UHFFFAOYSA-N 3-hydroxyphthalic acid Chemical compound OC(=O)C1=CC=CC(O)=C1C(O)=O MNUOZFHYBCRUOD-UHFFFAOYSA-N 0.000 description 2
- RSFDFESMVAIVKO-UHFFFAOYSA-N 3-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S)=C1 RSFDFESMVAIVKO-UHFFFAOYSA-N 0.000 description 2
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 2
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- IJJNNSUCZDJDLP-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 IJJNNSUCZDJDLP-UHFFFAOYSA-N 0.000 description 2
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-UHFFFAOYSA-N 0.000 description 2
- GEYAGBVEAJGCFB-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GEYAGBVEAJGCFB-UHFFFAOYSA-N 0.000 description 2
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 2
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 2
- ABJQKDJOYSQVFX-UHFFFAOYSA-N 4-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=C1 ABJQKDJOYSQVFX-UHFFFAOYSA-N 0.000 description 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 2
- JXYITCJMBRETQX-UHFFFAOYSA-N 4-ethynylaniline Chemical compound NC1=CC=C(C#C)C=C1 JXYITCJMBRETQX-UHFFFAOYSA-N 0.000 description 2
- SJXHLZCPDZPBPW-UHFFFAOYSA-N 4-ethynylbenzoic acid Chemical compound OC(=O)C1=CC=C(C#C)C=C1 SJXHLZCPDZPBPW-UHFFFAOYSA-N 0.000 description 2
- CCTOEAMRIIXGDJ-UHFFFAOYSA-N 4-hydroxy-2-benzofuran-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)OC2=O CCTOEAMRIIXGDJ-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 2
- HWAQOZGATRIYQG-UHFFFAOYSA-N 4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1 HWAQOZGATRIYQG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 2
- FSBRKZMSECKELY-UHFFFAOYSA-N 5-aminonaphthalen-2-ol Chemical compound OC1=CC=C2C(N)=CC=CC2=C1 FSBRKZMSECKELY-UHFFFAOYSA-N 0.000 description 2
- FPKNJPIDCMAIDW-UHFFFAOYSA-N 5-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1C(O)=O FPKNJPIDCMAIDW-UHFFFAOYSA-N 0.000 description 2
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- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- NRTMJDNEXVMKPP-UHFFFAOYSA-N NC1=C(C=CC2=CC=CC=C12)O.OC1=CC2=CC=CC=C2C=C1N Chemical compound NC1=C(C=CC2=CC=CC=C12)O.OC1=CC2=CC=CC=C2C=C1N NRTMJDNEXVMKPP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NZGDYFIFDIDVNE-UHFFFAOYSA-N SC1=C(C=CC2=CC=CC=C12)N.SC1=CC(=CC2=CC=CC=C12)N Chemical compound SC1=C(C=CC2=CC=CC=C12)N.SC1=CC(=CC2=CC=CC=C12)N NZGDYFIFDIDVNE-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000010599 Verbascum thapsus Nutrition 0.000 description 1
- 244000178289 Verbascum thapsus Species 0.000 description 1
- CQHKDHVZYZUZMJ-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-prop-2-enoyloxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CO)COC(=O)C=C CQHKDHVZYZUZMJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 1
- HSUIVCLOAAJSRE-UHFFFAOYSA-N bis(2-methoxyethyl) benzene-1,2-dicarboxylate Chemical compound COCCOC(=O)C1=CC=CC=C1C(=O)OCCOC HSUIVCLOAAJSRE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004202 carbamide Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
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- 229920001577 copolymer Polymers 0.000 description 1
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- 150000004775 coumarins Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- CMDHNEAPXOZXBI-UHFFFAOYSA-N n-[4-[4-(hydroxyamino)phenyl]phenyl]hydroxylamine Chemical compound C1=CC(NO)=CC=C1C1=CC=C(NO)C=C1 CMDHNEAPXOZXBI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JSKSILUXAHIKNP-UHFFFAOYSA-N naphthalene-1,7-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(C(=O)O)=CC=C21 JSKSILUXAHIKNP-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920003210 poly(4-hydroxy benzoic acid) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JRDBISOHUUQXHE-UHFFFAOYSA-N pyridine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)N=C1C(O)=O JRDBISOHUUQXHE-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- RKFCDGOVCBYSEW-AUUKWEANSA-N tmeg Chemical compound COC=1C(OC)=CC(C(OC(C=2OC)=C34)=O)=C3C=1OC(=O)C4=CC=2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RKFCDGOVCBYSEW-AUUKWEANSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
Images
Description
(一般式(2)中、R 6 は炭素数1〜20の1価の有機基、Cl、Br、IまたはFを示す。R 7 およびR 8 は、CH 2 OR 10 (R 10 は水素原子または炭素数1〜6の1価の炭化水素基)を示す。R 9 は水素原子、メチル基またはエチル基を示す。hは0〜2の整数、iは1〜4の整数を示す。iが2〜4の場合、複数のR 6 〜R 9 はそれぞれ同じでも異なってもよいが、同一のベンゼン環がR 6 を2つ有する場合は、R 6 は同じである。R 11 〜R 33 は水素原子、炭素数1〜20の1価の有機基、Cl、Br、IまたはFを示す。)
また、本発明は、上記の感光性樹脂組成物を基板上に塗布し感光性樹脂膜を形成する工程、該感光性樹脂膜を乾燥する工程、該感光性樹脂膜を露光する工程、露光された感光性樹脂膜を現像する工程、および、加熱処理をする工程を含む耐熱性樹脂膜の製造方法である。
上記の一般式(1)で表される構造単位を有する樹脂を、以下(a)成分と呼ぶ。(a)成分は、加熱あるいは適当な触媒により、イミド環、オキサゾール環、またはその他の環状構造を有するポリマーとなり得るものである。環構造となることで、耐熱性、耐溶剤性が飛躍的に向上する。(a)成分としては、耐熱性に優れ、有機電界発光素子の絶縁層、あるいは、半導体素子の表面保護膜や層間絶縁膜として優れた特性を示すことから、ポリイミド前駆体またはポリベンゾオキサゾール前駆体が好ましい。すなわち、(a)成分は耐熱性樹脂前駆体であり、(a)成分を加熱することによって耐熱性樹脂が得られる。ここで、耐熱性樹脂とは、ポリイミド樹脂、ポリベンゾオキサゾール樹脂等のイミド環、オキサゾール環、またはその他の環状構造を有するポリマーのことである。
本発明の(b)感光剤としては、ポジ型感光剤とネガ型感光剤のいずれも用いることができる。本発明に用いる感光剤としては、キノンジアジド化合物が好ましい。キノンジアジド化合物は、樹脂組成物にポジ型の感光特性を与える感光剤である。樹脂組成物がポジ型の感光特性を有すると、パターン加工に際して、露光部の塗膜内部への放射線有効強度が、塗膜の表面から底部に向かって次第に小さくなり、図1に示すように順テーパー状の断面形状を有する絶縁層を形成することが容易であるので好ましい。
本発明の感光性樹脂組成物は、(c)アルキレンオキサイド鎖を含有する化合物を含有する。(c)アルキレンオキサイド鎖を含有する化合物を含有することで、感光性樹脂組成物の感度を向上させることができる。(c)の構造は一般式(3)で表されるものが好ましい。
一般式(3)中、lおよびzはそれぞれ独立に0または1、好ましくはl=z=1である。nおよびxは、それぞれ独立に1〜20の整数を示し、好ましくは1〜4である。mおよびyは、それぞれ独立に1〜20の整数を示し、好ましくはm+yが4〜16である。R35の構造として(A−1)〜(A−13)が挙げられる。特に(A−7)、(A−9)、(A−10)が好ましい。また、R34およびR36の構造としては(B−1)〜(B−6)が挙げられ、特に(B−1)、(B−4)、(B−5)が好ましい。
本発明の樹脂組成物は、(d)一般式(2)で表される熱架橋剤を含有する。かかる熱架橋剤は従来公知の尿素・メラミン系熱架橋剤に比べて架橋反応温度が高く、かつ架橋反応性が高いため、パターン加工時のプリベーク工程での架橋反応を防ぐことができ、かつ、得られる硬化膜の耐薬品性を向上させることができる。特に、250℃以下の低温で焼成した場合にも、十分な耐薬品性を有する硬化膜を得ることができる。また、本発明においては、(c)アルキレンオキサイド鎖を含有する化合物を添加した感光性樹脂組成を用いてパターン形成する場合において、キュアした際に生じる高テーパー角化を防ぐことができる。
大日本スクリーン製造(株)製ラムダエースSTM−602を使用し、プリベーク後および現像後の膜は、屈折率1.629として測定した。
東京エレクトロン(株)製の塗布現像装置ACT−8を用いて、8インチシリコンウエハー上に、ワニスを現像後の膜厚が3.6μmとなるように塗布し、ついで120℃で2分ベークすることにより、プリベーク膜を得た。
感光性樹脂膜に、20μmラインのフォトマスクを介して露光および現像し得られたパターンの開溝寸法を、レーザー顕微鏡を用いて測長した。開溝寸法が20μmを越える最小の露光量を感度とした。感度が120mJ/cm2以下の場合を合格(○)とし、120mJ/cm2より大きく150mJ/cm2以下の場合を△、150mJ/cm2を超える場合を不合格(×)とした。
光洋サーモシステム(株)製イナートオーブンINH−21CDを用いて、窒素気流下(酸素濃度20ppm以下)、250℃で1時間キュアし、耐熱性樹脂被膜(キュア膜)を作製した。得られたキュア膜の10μmラインを日立ハイテクノロジーズ(株)製電界放出型走査電子顕微鏡S−4800を用いて撮影し、テーパー角を測定した。テーパー角とは、パターン側面と基板表面のなす角度を指し、図1においてθで示す角をいう。テーパー角の測定はパターン断面の電子顕微鏡観察により行う。テーパー角が55°以下の場合を合格(○)とし、55°よりも大きい場合を不合格(×)とした。
乾燥窒素気流下、2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(BAHF)18.3g(0.05モル)とアリルグリシジルエーテル34.2g(0.3モル)をγ−ブチロラクトン100gに溶解させ、−15℃に冷却した。ここにγ−ブチロラクトン50gに溶解させた無水トリメリット酸クロリド22.1g(0.11モル)を反応液の温度が0℃を越えないように滴下した。滴下終了後、0℃で4時間反応させた。この溶液をロータリーエバポレーターで濃縮した後、トルエン1lに投入して酸無水物(a) を得た。
2−アミノ−4−ニトロフェノール15.4g(0.1モル)をアセトン50mlおよびプロピレンオキシド30g(0.34モル)に溶解させ、−15℃に冷却した。ここに2,2ビス−(4−ベンゾイルクロリド)ヘキサフルオロプロパン23.6g(0.055モル)をアセトン60mlに溶解させた溶液を徐々に滴下した。滴下終了後、−15℃で4時間反応させた。その後、室温に戻して生成している沈殿をろ過で集めた。
BAHF18.3g(0.05モル)をアセトン100mlおよびプロピレンオキシド17.4g(0.3モル)に溶解させ、−15℃に冷却した。ここに4−ニトロベンゾイルクロリド20.4g(0.11モル)をアセトン100mlに溶解させた溶液を滴下した。滴下終了後、−15℃で4時間反応させ、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)21.23g(0.05モル)と5−ナフトキノンジアジドスルホニル酸クロリド33.58g(0.125モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合させたトリエチルアミン12.65g(0.125モル)を系内が35℃以上にならないように滴下した。滴下後30℃で2時間撹拌した。トリエチルアミン塩を濾過し、ろ液を水に投入させた。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、キノンジアジド化合物(d)を得た。
乾燥窒素気流下、合成例1で得られた水酸基含有酸無水物(a)12.01g(0.02モル)をN−メチル−2−ピロリドン(NMP)100gに溶解させた。ここに合成例2で得られた水酸基含有ジアミン(b)9.6g(0.016モル)をNMP25gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。次に4−アミノフェノール0.87g(0.008モル)を加え50℃で2時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール7.15g(0.06モル)をNMP10g で希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。反応終了後、溶液を水1lに投入して、沈殿した樹脂(樹脂A)をろ過で集めた。樹脂Aを80℃の真空乾燥機で40時間乾燥した。
実施例1で得た樹脂A 10g、合成例4で得られたキノンジアジド化合物(d)1.5g、MX−280 0.3gおよびPDBE−450A 0.01gをプロピレングリコールモノメチルエーテル(沸点118−119℃)35gとγ−ブチロラクトン(沸点204℃)15gの混合溶媒に溶解して、感光性ポリイミド前駆体樹脂組成物のワニスW2を得た。得られたワニスW2を用いて、実施例1と同様に評価を行った。得られた結果を表1に示す。
実施例1で得た樹脂A 10g 、合成例4で得られたキノンジアジド化合物(d)1.5g、MX−280 0.3gおよびPDBE−450A 1gをプロピレングリコールモノメチルエーテル(沸点118−119℃)35gとγ−ブチロラクトン(沸点204℃)15gの混合溶媒に溶解して、感光性ポリイミド前駆体樹脂組成物のワニスW3を得た。得られたワニスW3を用いて、実施例1と同様に評価を行った。得られた結果を表1に示す。
乾燥窒素気流下、合成例3で得られた水酸基含有ジアミン化合物(c)9.67g(0.016モル)、1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン0.50g(0.002モル)、末端封止剤として3−アミノフェノール0.44g(0.004モル)をN−メチル−2−ピロリドン(NMP)50gに溶解させた。ここにビス(3,4−ジカルボキシフェニル)エーテル二無水物6.2g(0.02モル)をNMP14gとともに加えて、20℃で1時間反応させ、次いで50℃で4時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール7.15g(0.06モル)をNMP5gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。反応終了後、溶液を水1lに投入して、沈殿した樹脂(樹脂B)をろ過で集めた。樹脂Bを70℃の真空乾燥機で60時間乾燥した。
乾燥窒素気流下、4,4’−ジアミノジフェニルエーテル9.08g(0.045モル)、1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)をN−メチル−2−ピロリドン(NMP)20gに溶解させた。ここに合成例1で得られた水酸基含有酸二無水物(a) 24.02g(0.04モル)をNMP15gとともに加えて、20℃ で1時間反応させ、次いで50℃で2時間反応させた。反応後、末端封止剤として無水マレイン酸1.96g(0.02モル)を加えさらに50℃で2時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール15.19g(0.127モル)をNMP4gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。反応終了後、溶液を水1lに投入して、沈殿した樹脂(樹脂C)をろ過で集めた。樹脂Cを70℃の真空乾燥機で60時間乾燥した。
実施例1で得た樹脂A 10g、合成例4で得られたキノンジアジド化合物(d)1.5g、MX−280 0.3g、およびMTG−A 0.1gをプロピレングリコールモノメチルエーテル(沸点118−119℃)35gとγ−ブチロラクトン(沸点204℃)15gの混合溶媒に溶解して、感光性ポリイミド前駆体樹脂組成物のワニスW6を得た。得られたワニスW6を用いて、実施例1と同様に評価を行った。得られた結果を表1に示す。
乾燥窒素気流下、BAHF18.3g(0.05モル)をNMP50g、グリシジルメチルエーテル26.4g(0.3モル)に溶解させ、溶液の温度を−15℃まで冷却した。ここにジフェニルエーテルジカルボン酸ジクロリド14.7g(0.050モル)をγ−ブチロラクトン25gに溶解させた溶液を内部の温度が0℃を越えないように滴下した。滴下終了後、−15℃で6時間撹拌を続けた。反応終了後、溶液を水3Lに投入して白色の沈殿を集めた。この沈殿をろ過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥し、樹脂Dを得た。
実施例7で得た樹脂D 10g、合成例5で得られたキノンジアジド化合物(d)1.5g 、および熱架橋剤HMOM 0.3gおよびMTG−A 0.1gをプロピレングリコールモノメチルエーテル(沸点118−119℃)25gとγ−ブチロラクトン(沸点204℃)25gの混合溶媒に溶解して、感光性ポリイミド前駆体樹脂組成物のワニスW8を得た。得られたワニスW8を用いて、実施例1と同様に評価を行った。得られた結果を表1に示す。
実施例1において熱架橋剤を加えない以外は、同様の評価を行ったところ、感度は120mJ/cm2と良好であったが、テーパー角が65°となり、低テーパー角とならなかった。
実施例1でアルキレンオキサイド鎖を有する化合物を加えない以外は、同様の評価を行ったところ、低テーパー角であったが、感度が150mJ/cm2を超える結果となり、高感度を示さなかった。
実施例7で熱架橋剤を加えない以外は、同様の評価を行ったところ、感度は120mJ/cm2と良好であったが、テーパー角が65°となり、低テーパー角とならなかった。
実施例7でアルキレンオキサイド鎖を有する化合物を加えない以外は、同様の評価を行ったところ、低テーパー角であったが、感度が150mJ/cm2を超える結果となり、高感度を示さなかった。
2.第一電極
3.絶縁層
Claims (5)
- (a)一般式(1)で表される構造単位を有する樹脂、(b)キノンジアジド化合物、(c)一般式(3)で表されるアルキレンオキサイド鎖を含有する化合物、および(d)一般式(2)で表される熱架橋剤を含有することを特徴とする感光性樹脂組成物。
(上記一般式(2)中、R6は炭素数1〜20の1価の有機基、Cl、Br、IまたはFを示す。R7およびR8は、CH2OR10(R10は水素原子または炭素数1〜6の1価の炭化水素基)を示す。R9は水素原子、メチル基またはエチル基を示す。hは0〜2の整数、iは1〜4の整数を示す。iが2〜4の場合、複数のR6〜R9はそれぞれ同じでも異なってもよいが、同一のベンゼン環がR6を2つ有する場合は、R6は同じである。)
(上記一般式(2)中、R11〜R33はそれぞれ独立に水素原子、炭素数1〜20の1価の有機基、Cl、Br、IまたはFを示す。)
- 前記(c)一般式(3)で表されるアルキレンオキサイド鎖を含有する化合物の含有量が、前記(a)一般式(1)で表される構造単位を有する樹脂100重量部に対して0.01〜1重量部であることを特徴とする請求項1に記載の感光性樹脂組成物。
- 請求項1または2に記載の感光性樹脂組成物を用いた電子部品。
- 請求項1または2に記載の感光性樹脂組成物を基板上に塗布し感光性樹脂膜を形成する工程、該感光性樹脂膜を乾燥する工程、該感光性樹脂膜を露光する工程、露光された感光性樹脂膜を現像する工程、および、加熱処理をする工程を含む耐熱性樹脂膜の製造方法。
- 請求項1または2に記載の感光性樹脂組成物を、第一電極が形成された基板上に塗布し感光性樹脂膜を形成する工程、該感光性樹脂膜を乾燥、露光、現像および加熱処理して絶縁層を形成する工程、発光層を形成する工程、および、第二電極を形成する工程を少なくとも含む有機電界発光装置の製造方法。
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