JP5950069B1 - ノボラック型フェノール樹脂、その製造方法、感光性組成物、レジスト材料、及び塗膜 - Google Patents
ノボラック型フェノール樹脂、その製造方法、感光性組成物、レジスト材料、及び塗膜 Download PDFInfo
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- JP5950069B1 JP5950069B1 JP2016509802A JP2016509802A JP5950069B1 JP 5950069 B1 JP5950069 B1 JP 5950069B1 JP 2016509802 A JP2016509802 A JP 2016509802A JP 2016509802 A JP2016509802 A JP 2016509802A JP 5950069 B1 JP5950069 B1 JP 5950069B1
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- phenolic
- novolak
- compound
- resin
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- 229920003986 novolac Polymers 0.000 title claims abstract description 101
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 239000000463 material Substances 0.000 title claims abstract description 21
- 239000005011 phenolic resin Substances 0.000 title claims description 76
- 238000000034 method Methods 0.000 title claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 219
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 229920005989 resin Polymers 0.000 claims abstract description 83
- 239000011347 resin Substances 0.000 claims abstract description 83
- 150000002989 phenols Chemical class 0.000 claims abstract description 58
- 125000002887 hydroxy group Chemical class [H]O* 0.000 claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 43
- 238000006482 condensation reaction Methods 0.000 claims abstract description 33
- 238000000576 coating method Methods 0.000 claims abstract description 26
- 239000011248 coating agent Substances 0.000 claims abstract description 25
- 239000003377 acid catalyst Substances 0.000 claims abstract description 22
- 239000010680 novolac-type phenolic resin Substances 0.000 claims abstract description 9
- -1 aldehyde aldehydes Chemical class 0.000 claims description 117
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 150000001299 aldehydes Chemical class 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 229920001568 phenolic resin Polymers 0.000 claims description 24
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 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 claims description 17
- 229930003836 cresol Natural products 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000002835 absorbance Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 description 44
- 238000003786 synthesis reaction Methods 0.000 description 44
- 239000010408 film Substances 0.000 description 43
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 33
- 238000005227 gel permeation chromatography Methods 0.000 description 33
- 230000035945 sensitivity Effects 0.000 description 28
- 239000003960 organic solvent Substances 0.000 description 21
- 238000005259 measurement Methods 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000003513 alkali Substances 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000002904 solvent Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 12
- 239000011572 manganese Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 11
- 229920002120 photoresistant polymer Polymers 0.000 description 11
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229940093475 2-ethoxyethanol Drugs 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 6
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 6
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 238000001226 reprecipitation Methods 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 229940116315 oxalic acid Drugs 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-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
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 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
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 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 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229940100630 metacresol Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 230000036211 photosensitivity Effects 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
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
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- PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
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- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
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- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical class N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
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- 239000000049 pigment Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
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- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
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- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QVQDALFNSIKMBH-UHFFFAOYSA-N 2-pentoxyethanol Chemical compound CCCCCOCCO QVQDALFNSIKMBH-UHFFFAOYSA-N 0.000 description 2
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
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- WXYSZTISEJBRHW-UHFFFAOYSA-N 4-[2-[4-[1,1-bis(4-hydroxyphenyl)ethyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(C(C)(C=2C=CC(O)=CC=2)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WXYSZTISEJBRHW-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
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- MPNBXFXEMHPGTK-UHFFFAOYSA-N pyrimidine-4,5,6-triamine Chemical compound NC1=NC=NC(N)=C1N MPNBXFXEMHPGTK-UHFFFAOYSA-N 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 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
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- VZUBRRXYUOJBRS-UHFFFAOYSA-N trichloromethylsulfonylbenzene Chemical compound ClC(Cl)(Cl)S(=O)(=O)C1=CC=CC=C1 VZUBRRXYUOJBRS-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
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
本発明はさらに、前記ノボラック型フェノール樹脂を含有する感光性組成物、前記感光性組成物からなるレジスト材料、及び前記レジスト材料からなる塗膜に関する。
測定装置:東ソー株式会社製「HLC−8220 GPC」
カラム:昭和電工株式会社製「Shodex KF802」(8.0mmI.D.×300mm)+昭和電工株式会社製「Shodex KF802」(8.0mmI.D.×300mm)+昭和電工株式会社製「Shodex KF803」(8.0mmI.D.×300mm)+昭和電工株式会社製「Shodex KF804」(8.0mmI.D.×300mm)、
カラム温度:40℃、
検出器: RI(示差屈折計)、
データ処理:東ソー株式会社製「GPC−8020モデルIIバージョン4.30」、
展開溶媒:テトラヒドロフラン、
流速:1.0mL/分、
試料:樹脂固形分換算で0.5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、
注入量:0.1mL、
標準試料:下記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−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」
樹脂の分子量分布は、GPCにより、ポリスチレン標準法において、以下の測定条件にて測定した。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:昭和電工株式会社製「Shodex KF802」(8.0mmI.D.×300mm)+昭和電工株式会社製「Shodex KF802」(8.0mmI.D.×300mm)+昭和電工株式会社製「Shodex KF803」(8.0mmI.D.×300mm)+昭和電工株式会社製「Shodex KF804」(8.0mmI.D.×300mm)、
検出器: RI(示差屈折計)、
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)、
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」、
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。
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」
樹脂の13C−NMRスペクトルの測定は、日本電子株式会社製「JNM−LA300」を用い、試料のDMSO−d6溶液を分析して構造解析を行った。以下に、13C−NMRスペクトルの測定条件を示す。
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
試料濃度:30wt%
積算回数:10000回
冷却管を取り付けた2L容4つ口フラスコに、2,5−キシレノール293.2g(2.4モル)、4−ヒドロキシベンズアルデヒド122g(1モル)、及び2−エトキシエタノール500mLを仕込み、2−エトキシエタノールに2,5−キシレノール及び4−ヒドロキシベンズアルデヒドを溶解させた。続いて、当該4つ口フラスコ内の反応溶液に、氷浴中で冷却しながら硫酸10mLを添加した後、マントルヒーターで100℃、2時間加熱し、攪拌しながら反応させた。反応終了後の反応溶液に水を添加して再沈殿操作を行い、粗生成物を得た。当該粗生成物をアセトンに再溶解させた後、さらに水で再沈殿操作を行った。再沈殿操作により得られた生成物を濾別し、真空乾燥を行い、白色結晶の前駆体化合物(フェノール系3核体化合物(1))213gを得た。フェノール系3核体化合物(1)について、GPC及び13C−NMRスペクトル測定を行ったところ、目的の化合物であり、純度はGPCの面積比で98.2質量%であることを確認した。フェノール系3核体化合物(1)のGPCのチャート図を図1に、13C−NMRスペクトルのチャート図を図2に、それぞれ示す。
4−ヒドロキシベンズアルデヒド122g(1モル)に代えて、ベンズアルデヒド106.1g(1モル)を用いた以外は合成例1と同様にして、白色結晶の前駆体化合物(フェノール系3核体化合物(2))206gを得た。フェノール系3核体化合物(2)について、GPC及び13C−NMRスペクトル測定を行ったところ、目的の化合物であり、純度はGPCの面積比で98.7質量%であることを確認した。フェノール系3核体化合物(2)のGPCのチャート図を図3に、13C−NMRスペクトルのチャート図を図4に、それぞれ示す。
冷却管を取り付けた300mL容4つ口フラスコに、合成例1で得たフェノール系3核体化合物(1)4.2g(0.012モル)と合成例2で得たフェノール系3核体化合物(2)12.6g(0.038モル)、92%パラホルムアルデヒド1.6g(0.05モル)、2−エトキシエタノール15mL、及び酢酸15mLを仕込み、2−エトキシエタノールと酢酸の混合溶媒中にフェノール系3核体化合物(1)及びパラホルムアルデヒドを溶解させた(フェノール系3核体化合物(1):フェノール系3核体化合物(2)=25:75)。続いて、当該4つ口フラスコ内の反応溶液に、氷浴中で冷却しながら硫酸10mLを添加した後、オイルバスで80℃に昇温し、4時間加熱し、攪拌しながら反応させた。反応終了後の反応溶液に水を添加して再沈殿操作を行い、粗生成物を得た。当該粗生成物をアセトンに再溶解させた後、さらに水で再沈殿操作を行った。再沈殿操作により得られた生成物を濾別し、真空乾燥を行い、淡赤色粉末のノボラック型フェノール樹脂(ノボラック樹脂(3−a))16.5gを得た。ノボラック樹脂(3−a)のGPCチャートを図5に示す。ノボラック樹脂(3−a)について、GPCを行ったところ、GPCを行ったところ、数平均分子量(Mn)=3,654、重量平均分子量(Mw)=18,798、多分散度(Mw/Mn)=5.144であった。
合成例1で得たフェノール系3核体化合物(1)4.2g(0.012モル)と合成例2で得たフェノール系3核体化合物(2)12.6g(0.038モル)に代えて、合成例1で得たフェノール系3核体化合物(1)8.7g(0.025モル)と合成例2で得たフェノール系3核体化合物(2)8.3g(0.025モル)を用いた(フェノール系3核体化合物(1):フェノール系3核体化合物(2)=50:50)以外は合成例3と同様にして、淡赤色粉末のノボラック型フェノール樹脂(ノボラック樹脂(3−b))16.2gを得た。ノボラック樹脂(3−b)のGPCチャートを図6に示す。ノボラック樹脂(3−b)について、GPCを行ったところ、数平均分子量(Mn)=2,529、重量平均分子量(Mw)=11,421、多分散度(Mw/Mn)=4.516であった。
合成例1で得たフェノール系3核体化合物(1)4.2g(0.012モル)と合成例2で得たフェノール系3核体化合物(2)12.6g(0.038モル)に代えて、合成例1で得たフェノール系3核体化合物(1)13.2g(0.038モル)と合成例2で得たフェノール系3核体化合物(2)4.0g(0.012モル)を用いた(フェノール系3核体化合物(1):フェノール系3核体化合物(2)=75:25)以外は合成例3と同様にして、淡赤色粉末のノボラック型フェノール樹脂(ノボラック樹脂(3−c))16.7gを得た。ノボラック樹脂(3−c)のGPCチャートを図7に示す。ノボラック樹脂(3−c)、GPCを行ったところ、数平均分子量(Mn)=3,313、重量平均分子量(Mw)=25,435、多分散度(Mw/Mn)=7.678であった。
合成例1で得たフェノール系3核体化合物(1)4.2g(0.012モル)と合成例2で得たフェノール系3核体化合物(2)12.6g(0.038モル)に代えて、合成例1で得たフェノール系3核体化合物(1)17.4g(0.05モル)を用いた(フェノール系3核体化合物(1):フェノール系3核体化合物(2)=100:0)以外は合成例3と同様にして、淡赤色粉末のノボラック型フェノール樹脂(ノボラック樹脂(3−d))16.8gを得た。ノボラック樹脂(3−d)のGPCチャートを図8に示す。ノボラック樹脂(3−d)について、GPCを行ったところ、数平均分子量(Mn)=2,733、重量平均分子量(Mw)=10,984、多分散度(Mw/Mn)=4.019であった。
温度計及び撹拌装置を備えた2L容4つ口フラスコに、m−クレゾール648g(6モル)、p−クレゾール432g(4モル)、シュウ酸2.5g(0.2モル)、42%ホルムアルデヒド492gを仕込み、100℃まで昇温させ、反応させた。反応終了後の反応溶液を常圧で200℃まで脱水して蒸留した後、230℃で6時間減圧蒸留を行って、黄色固形のノボラック樹脂(ノボラック樹脂(3−e))736gを得た。ノボラック樹脂(3−e)のGPCチャートを図9に示す。ノボラック樹脂(3−e)について、GPCを行ったところ、数平均分子量(Mn)=1,450、重量平均分子量(Mw)=10,316、多分散度(Mw/Mn)=7.116であった。
合成例3〜5及び比較合成例1〜2で合成したノボラック樹脂(3−a)〜(3−e)について、ノボラック樹脂と感光剤「P−200」(4,4’−[1−[4−[1−(4−ヒドロキシフェニル)−1メチルエチル]フェニル]エチリデン]ビスフェノール(1モル)と1,2−ナフトキノン−2−ジアジド−5−スルホニルクロリド(2モル)の縮合物)(東洋合成工業製)、及びプロピレングリコールモノメチルエーテルアセテート(PGMEA)を20/5/75(質量部)で混合して溶解させた後、0.2μmメンブランフィルターを用いて濾過し、感光性組成物とした。
感度測定のためには、感光剤なしの感光性組成物として、ノボラック樹脂をPGMEAに溶解した組成物(ノボラック樹脂/PGMEA=20/80(質量部))を調製した。
感光性組成物を、5インチシリコンウェハー上にスピンコーターで塗布し、110℃のホットプレート上で60秒間乾燥させ、約1μmの厚さの薄膜を得た。得られたウェハーを、現像液(2.38%水酸化テトラメチルアンモニウム水溶液)に60秒間浸漬させた後、110℃のホットプレート上で60秒間乾燥させた。当該感光性組成物の塗膜の膜厚を、現像液浸漬前後で測定し、その差分を60で除した値をアルカリ溶解速度(ADR(nm/秒))とし、アルカリ現像性を評価した。塗膜の膜厚は、膜厚計(フィルメトリクス株式会社製「F−20」)を用いて測定した。
感光性組成物を約1μmの厚さで塗布して乾燥せしめたウェハー上に、ラインアンドスペースが1:1の1〜10μmレジストパターン対応のマスクを密着させた後、g・h・i線ランプ(ウシオ電機株式会社製、マルチライト)でL/S=3μmを忠実に再現することのできる露光量(Eop露光量)を求めた。
感光性組成物を塗布して乾燥したシリコンウェハー上にフォトマスクを乗せ、g・h・i線ランプ(ウシオ電機株式会社製、マルチライト)で200mJ/cm2照射し感光せしめた。照射後の塗膜を、ADR測定と同様にして現像し乾燥させた。現像後のウェハー上のレジストパターンのパターン状態を、キーエンス社製レーザーマイクロスコープ(VK−X200)を用いて評価した。評価は、L/S=5μmで解像できているものを「○」、L/S=5μmで解像できていないものを「×」とした。
耐熱性評価には、ノボラック樹脂をPGMEAに溶解し、固形分40質量%にしたPGMEA溶液を感光性組成物として用いた。 感光性組成物を5インチシリコンウェハー上に約1μmの厚さになるようにスピンコーターで塗布し、110℃のホットプレート上で60秒間乾燥させた。得られたウェハーより樹脂分をかきとり、Tgを測定した。Tgの測定は、示差走査熱量計「(DSC)Q100」(株式会社TAインスツルメント製)を用いて、窒素雰囲気下、温度範囲:−100〜200℃、昇温温度:10℃/分の条件で、走査を行い、測定結果をガラス転移温度(Tg)とした。
ノボラック樹脂をPGMEAに溶解し、固形分1質量%にしたPGMEA溶液を調製した。調製したPGMEA溶液について、可視領域にあたる365nm、405nm、436nmの各波長において、吸光度を測定した。吸光度測定は、紫外可視光光度計「UV−1600」(島津製作所株式会社製)に、石英製の測定セル(光路長:10mm、光路幅:10mm)を設置したもので測定した。設定パラメーターは、スペクトルバンド幅を2nm、測定波長範囲を190〜750nm、波長スケールを25nm/cm、スキャンスピードを100nm/分とした。
Claims (14)
- 下記一般式(1)
で表されるフェノール系3核体化合物(A1)と、
下記一般式(2−1)、(2−2)、(2−3)、及び(2−4)
で表される化合物からなる群から選ばれる1種以上のフェノール系3核体化合物(A2)と、アルデヒドアルデヒド類(B)とを必須の反応原料とするノボラック化反応物であり、前記フェノール系3核体化合物(A1)と前記フェノール系3核体化合物(A2)のモル比が20:80〜90:10であることを特徴とする、ノボラック型フェノール樹脂。 - 前記一般式(1−1)、(1−2)、(1−7)、(1−8)、(1−13)、及び(1−14)中のR1及びR2が共にメチル基又は共にエチル基であり、かつr1及びr2が0であり、
前記一般式(2−1)、(2−2)、(2−3)、及び(2−4)中のRがメチル基又はエチル基であり、かつ、tが0である、請求項2記載のノボラック型フェノール樹脂。 - 繰り返し単位として、下記一般式(I−1)
で表される構造部位(I−1)、及び下記一般式(II−1)
で表される構造部位(II−1)からなる群より選択される1種以上の構造部位を有する、請求項1に記載のノボラック型フェノール樹脂。 - 重量平均分子量が5,000〜35,000である、請求項1に記載のノボラック型フェノール樹脂。
- ジアルキル置換フェノールと水酸基含有芳香族アルデヒドとの縮合反応を行い、得られた縮合物から、フェノール系3核体化合物(A1)を単離精製する工程と、
2,3位、2,5位、3,4位、又は3,5位の位置にアルキル基を有するジアルキル置換フェノールと水酸基を有さない芳香族アルデヒドとの縮合反応を行い、得られた縮合物から、フェノール系3核体化合物(A2)を単離精製する工程と、
単離精製されたフェノール系3核体化合物(A1)とフェノール系3核体化合物(A2)をモル比が20:80〜90:10となるように混合し、得られた混合物とアルデヒド類(B)との縮合反応を酸触媒下で行い、ノボラック型フェノール樹脂を得る工程と、
を有することを特徴とする、ノボラック型フェノール樹脂の製造方法。 - 請求項1〜5の何れか一項に記載のノボラック型フェノール樹脂と感光剤とを含有する、感光性組成物。
- 下記一般式(1)
で表されるフェノール系3核体化合物(A1)とアルデヒド類(B)とのノボラック化反応物であるノボラック型フェノール樹脂(A1)と、
下記一般式(2−1)、(2−2)、(2−3)、及び(2−4)
で表される化合物からなる群から選ばれる1種以上のフェノール系3核体化合物(A2)とアルデヒド類(B)とのノボラック化反応物であるノボラック型フェノール樹脂(A2)とを含有することを特徴とする、ノボラック型フェノール樹脂組成物。 - 前記ノボラック型フェノール樹脂(A1)と前記ノボラック型フェノール樹脂(A2)の含有比率が、フェノール系3核体化合物(A1)に由来する構成単位と、フェノール系3核体化合物(A2)に由来する構成単位のモル比で20:80〜90:10となる範囲である、請求項8記載のノボラック型フェノール樹脂組成物。
- 請求項8又は9に記載のノボラック型フェノール樹脂組成物と感光剤とを含有する、感光性組成物。
- さらに、クレゾールノボラック樹脂を含有する、請求項7又は10記載の感光性組成物。
- 請求項7、10、11のいずれか一項に記載の感光性組成物からなるレジスト材料。
- 請求項12に記載のレジスト材料からなる塗膜。
- 膜厚が2μm以上である、請求項13に記載の塗膜。
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