JPWO2015008560A1 - フェノール性水酸基含有化合物、感光性組成物、レジスト用組成物、レジスト塗膜、硬化性組成物、レジスト下層膜用組成物、及びレジスト下層膜 - Google Patents
フェノール性水酸基含有化合物、感光性組成物、レジスト用組成物、レジスト塗膜、硬化性組成物、レジスト下層膜用組成物、及びレジスト下層膜 Download PDFInfo
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- JPWO2015008560A1 JPWO2015008560A1 JP2014556288A JP2014556288A JPWO2015008560A1 JP WO2015008560 A1 JPWO2015008560 A1 JP WO2015008560A1 JP 2014556288 A JP2014556288 A JP 2014556288A JP 2014556288 A JP2014556288 A JP 2014556288A JP WO2015008560 A1 JPWO2015008560 A1 JP WO2015008560A1
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- Prior art keywords
- group
- phenolic hydroxyl
- composition
- hydroxyl group
- containing compound
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 122
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 108
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 238000000576 coating method Methods 0.000 title claims description 22
- 239000011248 coating agent Substances 0.000 title claims description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- -1 dihydroxynaphthalene compound Chemical class 0.000 claims description 137
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 45
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000001312 dry etching Methods 0.000 abstract description 19
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 18
- 230000036211 photosensitivity Effects 0.000 abstract description 18
- 238000000354 decomposition reaction Methods 0.000 abstract description 10
- 239000005011 phenolic resin Substances 0.000 description 77
- 229920005989 resin Polymers 0.000 description 59
- 239000011347 resin Substances 0.000 description 59
- 238000000034 method Methods 0.000 description 25
- 229920003986 novolac Polymers 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 150000002989 phenols Chemical class 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000003513 alkali Substances 0.000 description 15
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 14
- 229930003836 cresol Natural products 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 13
- 229910052710 silicon Inorganic materials 0.000 description 13
- 239000010703 silicon Substances 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000005979 thermal decomposition reaction Methods 0.000 description 12
- 238000001723 curing Methods 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 238000004090 dissolution Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000005530 etching Methods 0.000 description 8
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 8
- 238000000434 field desorption mass spectrometry Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 229920002120 photoresistant polymer Polymers 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229920001568 phenolic resin Polymers 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 238000000206 photolithography Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical group COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 4
- 229940100630 metacresol Drugs 0.000 description 4
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 239000003504 photosensitizing agent Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XGQJGMGAMHFMAO-UHFFFAOYSA-N 1,3,4,6-tetrakis(methoxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound COCN1C(=O)N(COC)C2C1N(COC)C(=O)N2COC XGQJGMGAMHFMAO-UHFFFAOYSA-N 0.000 description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 3
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 3
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 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 3
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001579 optical reflectometry Methods 0.000 description 3
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 229920003987 resole Chemical group 0.000 description 3
- 229960001755 resorcinol Drugs 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 2
- BOGFHOWTVGAYFK-UHFFFAOYSA-N 1-[2-(2-propoxyethoxy)ethoxy]propane Chemical compound CCCOCCOCCOCCC BOGFHOWTVGAYFK-UHFFFAOYSA-N 0.000 description 2
- CZAVRNDQSIORTH-UHFFFAOYSA-N 1-ethenoxy-2,2-bis(ethenoxymethyl)butane Chemical compound C=COCC(CC)(COC=C)COC=C CZAVRNDQSIORTH-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- CVXYHECBHMSYDW-UHFFFAOYSA-N 2-butoxyethanol 1-methoxypropan-2-ol Chemical compound COCC(C)O.CCCCOCCO CVXYHECBHMSYDW-UHFFFAOYSA-N 0.000 description 2
- GXYCPGOCXLHIAT-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxyphenyl)-(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=C(C2CCCCC2)C=CC=1)O)C1=CC=CC(C2CCCCC2)=C1O GXYCPGOCXLHIAT-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
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- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate 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
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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Abstract
Description
で表される分子構造を有することを特徴とするフェノール性水酸基含有化合物に関する。
で表される分子構造を有することを特徴とする。
で表される分子構造を有することがより好ましい。
で表される構造部位が挙げられ、具体的には、フェニル基、ヒドロキシフェニル基、ジヒドロキシフェニル基、ヒドロキシアルコキシフェニル基、アルコキシフェニル基、トリル基、キシリル基、ナフチル基、ヒドロキシナフチル基、ジヒドロキシナフチル基等が挙げられる。
の何れかで表される化合物が挙げられる。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテックジャパン株式会社製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(単分散ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A-2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
装置:日本電子(株)製 AL−400
溶媒:ジメチルスルホキシド−d6、TMS基準
試料濃度 :30wt%
測定モード:SGNNE(NOE消去の1H完全デカップリング法)
パルス角度:45°パルス
積算回数 :10000回
の条件で1H−NMR、13C−NMRを測定した。
日本電子株式会社製の二重収束型質量分析装置AX505H(FD505H)を用いて測定した。
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに、1,6−ジヒドロキシナフタレン48質量部(0.30モル)、42質量%ホルムアルデヒド水溶液26質量部(0.36モル)、イソプロピルアルコール50質量部、48%水酸化カリウム12.8質量部(0.11モル)を仕込み、室温下、窒素を吹き込みながら撹拌した。その後、80℃に昇温して1時間撹拌した。反応終了後、第1リン酸ソーダ8質量部を添加して中和した後、冷却して結晶物を濾別した。濾別した結晶物を水50質量部で3回洗浄した後、加熱減圧乾燥してフェノール樹脂(1)20質量部を得た。フェノール樹脂(1)のGPCチャートを図1に、13C−NMRチャートを図2に、MSスペクトルを図3に示す。MSスペクトルから下記構造式(i)で表されるフェノール性水酸基含有化合物に相当する688のピークが検出された。また、GPCチャートから算出されるフェノール樹脂(1)中の下記構造式(i)で表されるフェノール性水酸基含有化合物(I)の含有量は36%であった。
製造例1において48%水酸化カリウム12.8質量部(0.11モル)の代わりに水酸化ナトリウム9.4質量部(0.11モル)を用いた以外は実施例1と同様にしてフェノール樹脂(2)19質量部を得た。フェノール樹脂(2)のMSスペクトルから前記構造式(i)で表されるフェノール性水酸基含有化合物(I)に相当する688のピークが検出された。また、GPCチャートから算出されるフェノール樹脂(2)中の前記構造式(i)で表されるフェノール性水酸基含有化合物(I)の含有量は36%であった。
製造例1において42質量%ホルムアルデヒド水溶液26質量部(0.36モル)の代わりに92%パラホルムアルデヒド11.8質量部(0.36モル)を用いた以外は製造例1と同様にしてフェノール樹脂(3)17質量部を得た。フェノール樹脂(3)のMSスペクトルから前記構造式(i)で表されるフェノール性水酸基含有化合物(I)に相当する688のピークが検出された。また、GPCチャートから算出されるフェノール樹脂(3)中の前記構造式(i)で表されるフェノール性水酸基含有化合物(I)の含有量は33%であった。
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに、1,6−ジヒドロキシナフタレン160質量部、パラアルデヒド44質量部、2−エトキシエタノール320質量部、95%硫酸1.6質量部を仕込み、80℃に昇温後8時間撹拌した。反応終了後、酢酸エチル300質量部、イオン交換水160質量部を加えた後、分液漏斗で下層よりpH1の水層を棄却した。イオン交換水160質量部を用いた有機層洗浄を7回実施し、棄却される水層がpH4であることを確認した。エバポレータを用いて有機層を加熱減圧条件下で濃縮したのち乾燥させ、フェノール樹脂(4)174質量部(収率94質量%)を得た。フェノール樹脂(4)のGPCチャートを図4に示す。フェノール樹脂(4)のMSスペクトルから前記構造式(ii)で表されるフェノール性水酸基含有化合物(II)に相当する744のピークが検出された。また、GPCチャートから算出される、フェノール樹脂(4)中の下記構造式(ii)で表されるフェノール性水酸基含有化合物(II)の含有量は34%であった。
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに、1,6−ジヒドロキシナフタレン160質量部、4−ヒドロキシベンズアルデヒド122質量部、2−エトキシエタノール290質量部、95%硫酸1.7質量部を仕込み、80℃に昇温後8時間撹拌した。反応終了後、酢酸エチル300質量部、イオン交換水160質量部を加えた後、分液漏斗で下層よりpH1の水層を棄却した。イオン交換水160質量部を用いた有機層洗浄を7回実施し、棄却される水層がpH4であることを確認した。エバポレータを用いて有機層を加熱減圧条件下で濃縮したのち乾燥させ、フェノール樹脂(5)247質量部(収率93質量%)を得た。フェノール樹脂(5)のGPCチャートを図5に示す。FD−MSスペクトルから下記構造式(iii)で表されるフェノール性水酸基含有化合物(III)に相当する1156のピークが検出された。また、GPCチャート図から算出される、フェノール樹脂(5)中の下記構造式(iii)で表されるフェノール性水酸基含有化合物(III)の含有量は89%であった。
実施例5で得られたフェノール樹脂(5)20質量部をメタノール20質量部に溶解した後、イオン交換水60質量部中に撹拌しながら滴下し、再沈殿操作を行った。生成した沈殿をフィルターでろ過し、得られたろ残を分取したのちに減圧乾燥器を用いて乾燥を行い、フェノール性水酸基含有化合物(III)12質量部を単離精製した。得られたフェノール性水酸基含有化合物(1)のGPCチャートを図6に、1H−NMRチャートを図7に、IRチャートを図8に、FD−MSチャートを図9に示す。
実施例5の4−ヒドロキシベンズアルデヒドをサリチルアルデヒド122質量部とした以外は実施例1と同様の操作を行い、フェノール樹脂(6)252質量部(収率95質量%)を得た。フェノール樹脂(6)のGPCチャートを図10に示す。FD−MSスペクトルから下記構造式(iv)で表されるフェノール性水酸基含有化合物(IV)に相当する1156のピークが検出された。また、GPCチャート図から算出される、フェノール樹脂(6)中の前記構造式(iv)で表されるフェノール性水酸基含有化合物(IV)の含有量は65%であった。
実施例7で得られたフェノール樹脂(6)20質量部を使用した以外は実施例6と同様の操作を行い、フェノール性水酸基含有化合物(IV)10質量部を単離精製した。得られたフェノール性水酸基含有化合物(IV)のGPCチャートを図11に、1H−NMRチャートを図12に、IRチャートを図13に、FD−MSチャートを図14に示す。
温度計、冷却管、撹拌器を取り付けたフラスコに、1,6−ジヒドロキシナフタレン160質量部(1.0モル)、メチルイソブチルケトン400質量部、水96質量部、及び92%パラホルムアルデヒド27.7質量部(0.85モル)を仕込み、室温下で撹拌した。更に、50%濃度に調整したパラトルエンスルホン酸水溶液4.8質量部を添加し、撹拌しながら80℃に昇温して2時間反応させた。反応終了後、系内の溶液を分液ロートに移し水層を有機層から分離除去した。次いで洗浄水が中性を示すまで水洗後、有機層から溶媒を加熱減圧下で除去し、フェノール樹脂(1’)を162質量部得た。
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに、α-ナフトール48質量部(0.30モル)、42質量%ホルムアルデヒド水溶液26質量部(0.36モル)、イソプロピルアルコール50質量部、48%水酸化ナトリウム9.4質量部(0.11モル)を仕込み、室温下、窒素を吹き込みながら撹拌した。その後、80℃に昇温して1時間撹拌した。反応終了後、第1リン酸ソーダ8質量部を添加して中和し、冷却して結晶物をろ別した。該結晶物を水50質量部で3回洗浄した後、加熱減圧乾燥してフェノール樹脂(2’)47質量部を得た。
コンデンサー、温度計、攪拌装置を備えた反応装置に、9,9−ビス(4−ヒドロキシフェニル)フルオレン100質量部とプロピレングリコールモノメチルエーテルアセテート100質量部及びパラホルムアルデヒド50質量部を仕込み、シュウ酸2質量部を添加し、脱水しながら120℃に昇温して、5時間反応させることにより、下記式で表される構造単位からなるフェノール樹脂(3’)98質量部を得た。
先で得たフェノール樹脂(1)〜(4)、フェノール性水酸基含有化合物(III)、(IV)、及びフェノール樹脂(1’)〜(3’)それぞれについて、下記要領で溶剤溶解性と耐熱性とを評価した。結果を表1に示す。
フェノール樹脂又はフェノール性水酸基含有化合物20質量部と、プロピレングリコールモノメチルエーテルアセテート(以下、「PGMEA」と略記する。)100質量部とを配合し、25℃の温度条件下、振とう機で撹拌した。撹拌後、容器内の溶剤の状態を目視で確認し、均一で透明な状態であったものを○、固形成分が析出または沈殿した状態であったものを×とした。
フェノール樹脂又はフェノール性水酸基含有化合物それぞれについて、示差熱熱重量同時測定装置(TG/DTA)を用い、下記条件で、一定速度で昇温した場合の重量減少を測定し、熱分解開始温度を求めた。熱分解開始温度が高いほど耐熱性に優れる。
測定機器:セイコーインスツールメント社製TG/DTA 6200
測定範囲:RT〜400℃
昇温速度:10℃/分
雰囲気:窒素
先で得たフェノール樹脂(1)〜(4)、フェノール性水酸基含有化合物(III)、(IV)、及びフェノール樹脂(1’)それぞれについて、下記要領で感光性組成物を調整し、光感度と解像度の評価試験を行った。結果を表2に示す。
・塗膜の作成
フェノール樹脂又はフェノール性水酸基含有化合物16質量部をPGMEA80質量部に溶解させ、更に感光剤(東洋合成工業株式会社製「P−200」)4質量部を加えて混合したものを0.2μmのメンブランフィルターでろ過し、感光性組成物(a)を得た。同様に、フェノール性水酸基含有化合物又はフェノール樹脂20質量部をPGMEA80質量部に溶解させたものを0.2μmのメンブランフィルターでろ過し、感光剤を含有しない組成物(b)を得た。
得られた組成物(a)、(b)それぞれを、直径5インチのシリコンウェハー上にスピンコーターを用いて塗布後、110℃で60秒乾燥し、厚さ約1μmの塗膜(A)及び(B)を得た。
得られた塗膜(A)、(B)をアルカリ溶液(2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液)に60秒浸漬させ、浸漬後の膜厚を膜厚計(フィルメトリクス社製「F−20」)にて測定し、アルカリ溶解速度(ADR)を評価した。塗膜(A)におけるアルカリ溶液溶解速度が低く、また、塗膜(B)におけるアルカリ溶解速度が高いほど、光感度に優れるレジスト用組成物である。
・塗膜の作成
フェノール樹脂又はフェノール性水酸基含有化合物16質量部をPGMEA80質量部に溶解させ、更に感光剤(東洋合成工業株式会社製「P−200」)4質量部を加えて混合したものを0.2μmのメンブランフィルターでろ過し、レジスト用組成物を得た。得られた感光性樹脂組成物を直径5インチのシリコンウェハー上にスピンコーターを用いて塗布した後、110℃で60秒乾燥させ、塗膜付きシリコンウェハーを作成した。
・解像度の評価
得られた塗膜付きシリコンウェハーの塗膜面にフォトマスクを乗せ、ウシオ電機株式会社製マルチライト(g・h・i線)で100mJ/cm2照射し感光させた。感光後のシリコンウェハーをアルカリ溶液(2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液)に60秒浸漬させた後、パターン表面を純水で洗い、スピンコーターでスピン乾燥した後、100℃で60秒乾燥させた。得られたシリコンウェハー上のレジストパターンの状態をレーザーマイクロスコープ(株式会社キーエンス製「VK−8500」)で確認し評価した。
○:L/S=5μmで解像できているもの、×:L/S=5μmで解像できていないもの。
先で得たフェノール樹脂(1)、(4)、フェノール性水酸基含有化合物(III)、(IV)、及びフェノール樹脂(3’)それぞれについて、下記要領で硬化性組成物を調整し、アルカリ溶液溶解速度とドライエッチング耐性の評価試験を行った。結果を表3に示す。
・塗膜の作成
フェノール性水酸基含有化合物又はフェノール樹脂20質量部と、硬化剤(東京化成工業株式会社製「1,3,4,6−テトラキス(メトキシメチル)グリコールウリル」)1質量部、をPGMEA100質量部に溶解させ、0.2μmのメンブランフィルターでろ過し、硬化性組成物を得た。これを直径5インチのシリコンウェハー上にスピンコーターを用いて塗布後、110℃で60秒乾燥し、厚さ約1μmの塗膜付きシリコンウェハーを得た。
・アルカリ溶液溶解速度の測定
得られた塗膜付きシリコンウェハーをアルカリ溶液(2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液)に60秒浸漬させ、浸漬後の膜厚を膜厚計(フィルメトリクス社製「F−20」)にて測定し、アルカリ溶解速度(ADR)を評価した。
・塗膜の作成
フェノール樹脂又はフェノール性水酸基含有化合物20質量部、硬化剤(東京化成工業株式会社製「1,3,4,6−テトラキス(メトキシメチル)グリコールウリル」)1質量部をPGMEA100質量部に加えて混合したものを0.2μmのメンブランフィルターでろ過し、硬化性組成物を得た。
・ドライエッチング耐性の評価
得られたレジスト下層膜用組成物を直径5インチのシリコンウェハー上にスピンコーターを用いて塗布した後、酸素濃度20容量%のホットプレート内にて、180℃で60秒間加熱した。更に、350℃で120秒間加熱して、膜厚0.3μmのレジスト下層膜付きシリコンウェハーを得た。形成したレジスト下層膜を、エッチング装置(神鋼精機社製の「EXAM」)を使用して、CF4/Ar/O2(CF4:40mL/分、Ar:20mL/分、O2:5mL/分 圧力:20Pa RFパワー:200W 処理時間:40秒 温度:15℃)の条件でエッチング処理した。このときのエッチング処理前後の膜厚を測定して、エッチングレートを算出し、エッチング耐性を評価した。評価基準は以下の通りである。
○:エッチングレートが150nm/分以下の場合
×:エッチングレートが150nm/分を超える場合
Claims (11)
- ジヒドロキシナフタレン化合物とホルムアルデヒドとを塩基性触媒の存在下で反応させて得られる請求項1記載のフェノール性水酸基含有化合物。
- ジヒドロキシナフタレン化合物と、炭素原子数が2つ以上の脂肪族アルデヒド化合物又は芳香族アルデヒド化合物とを、酸性触媒の存在下で反応させて得られる請求項1記載のフェノール性水酸基含有化合物。
- 請求項1〜4の何れか一つに記載のフェノール性水酸基含有化合物と感光剤とを含有する感光性組成物。
- 請求項5記載の感光性組成物からなるレジスト用組成物。
- 請求項5記載のレジスト用組成物からなるレジスト塗膜。
- 請求項1〜4の何れか一つに記載のフェノール性水酸基含有化合物と硬化剤とを含有する硬化性組成物。
- 請求項8記載の硬化性組成物を硬化させてなる硬化物。
- 請求項8記載の硬化性組成物からなるレジスト下層膜用組成物。
- 請求項10記載のレジスト下層膜用組成物からなるレジスト下層膜。
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