JP6304453B2 - ノボラック型樹脂及びレジスト膜 - Google Patents
ノボラック型樹脂及びレジスト膜 Download PDFInfo
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- JP6304453B2 JP6304453B2 JP2017529405A JP2017529405A JP6304453B2 JP 6304453 B2 JP6304453 B2 JP 6304453B2 JP 2017529405 A JP2017529405 A JP 2017529405A JP 2017529405 A JP2017529405 A JP 2017529405A JP 6304453 B2 JP6304453 B2 JP 6304453B2
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- 229920003986 novolac Polymers 0.000 title claims description 99
- 229920005989 resin Polymers 0.000 claims description 124
- 239000011347 resin Substances 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000004122 cyclic group Chemical group 0.000 claims description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- HBGPNLPABVUVKZ-POTXQNELSA-N (1r,3as,4s,5ar,5br,7r,7ar,11ar,11br,13as,13br)-4,7-dihydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysen-9-one Chemical compound C([C@@]12C)CC(=O)C(C)(C)[C@@H]1[C@H](O)C[C@]([C@]1(C)C[C@@H]3O)(C)[C@@H]2CC[C@H]1[C@@H]1[C@]3(C)CC[C@H]1C(=C)C HBGPNLPABVUVKZ-POTXQNELSA-N 0.000 claims 1
- PFRGGOIBYLYVKM-UHFFFAOYSA-N 15alpha-hydroxylup-20(29)-en-3-one Natural products CC(=C)C1CCC2(C)CC(O)C3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 PFRGGOIBYLYVKM-UHFFFAOYSA-N 0.000 claims 1
- SOKRNBGSNZXYIO-UHFFFAOYSA-N Resinone Natural products CC(=C)C1CCC2(C)C(O)CC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 SOKRNBGSNZXYIO-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- -1 naphthol compound Chemical class 0.000 description 164
- 239000005011 phenolic resin Substances 0.000 description 62
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 35
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- 238000006243 chemical reaction Methods 0.000 description 29
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- 238000005227 gel permeation chromatography Methods 0.000 description 20
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- 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 16
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- 125000006239 protecting group Chemical group 0.000 description 15
- 239000003822 epoxy resin Substances 0.000 description 14
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- 235000012431 wafers Nutrition 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 238000001723 curing Methods 0.000 description 10
- 238000000434 field desorption mass spectrometry Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 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
- 238000001312 dry etching Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000003377 acid catalyst Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000005530 etching Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer 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
- 239000000047 product Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 6
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000206 photolithography Methods 0.000 description 6
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- 230000036211 photosensitivity Effects 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 5
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920002223 polystyrene Polymers 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
- 238000006467 substitution reaction Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 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
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- 230000000052 comparative effect Effects 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
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- 238000005259 measurement Methods 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
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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Description
で表される分子構造を有する環状ノボラック型樹脂(A)を含有し、樹脂中に存在するXのうち少なくとも一つが3級アルキル基、アルコキシアルキル基、アシル基、アルコキシカルボニル基、ヘテロ原子含有環状炭化水素基、トリアルキルシリル基の何れかであり、樹脂中に存在する構造部位(α)のうち少なくとも一つはlが1である構造部位(α1)であり、少なくとも一つはlが2である構造部位(α2)であることを特徴とするノボラック型樹脂に関する。
で表される構造部位(β)であり、nは2〜10の整数である。]
で表される分子構造を有する環状フェノール樹脂中間体(A’)を含有し、樹脂中に存在する構造部位(β)のうち少なくとも一つはlが1である構造部位(β1)であり、少なくとも一つはlが2である構造部位(β2)であるフェノール樹脂中間体のフェノール性水酸基の水素原子の一部乃至全部を、3級アルキル基、アルコキシアルキル基、アシル基、アルコキシカルボニル基、ヘテロ原子含有環状炭化水素基、トリアルキルシリル基の何れかで置換する、ノボラック型樹脂の製造方法に関する。
本発明のノボラック型樹脂は、下記構造式(1)
で表される構造部位(α)であり、nは2〜10の整数である。]
で表される分子構造を有する環状ノボラック型樹脂(A)を含有し、樹脂中に存在するXのうち少なくとも一つが3級アルキル基、アルコキシアルキル基、アシル基、アルコキシカルボニル基、ヘテロ原子含有環状炭化水素基、トリアルキルシリル基の何れかであり、樹脂中に存在する構造部位(α)のうち少なくとも一つはlが1である構造部位(α1)であり、少なくとも一つはlが2である構造部位(α2)であることを特徴とする。
装置:日本電子株式会社製「JNM−LA300」
溶媒:DMSO−d6
[GPCの測定条件]
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」(8.0mmФ×300mm)
+昭和電工株式会社製「Shodex KF802」(8.0mmФ×300mm)
+昭和電工株式会社製「Shodex KF803」(8.0mmФ×300mm)
+昭和電工株式会社製「Shodex KF804」(8.0mmФ×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
(標準試料: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」
で表される分子構造を有する環状フェノール樹脂中間体(A’)を含有し、樹脂中に存在する構造部位(β)のうち少なくとも一つはlが1である構造部位(β1)であり、少なくとも一つはlが2である構造部位(β2)であるフェノール樹脂中間体のフェノール性水酸基の水素原子の一部乃至全部を、3級アルキル基、アルコキシアルキル基、アシル基、アルコキシカルボニル基、ヘテロ原子含有環状炭化水素基、トリアルキルシリル基の何れかで置換する方法が挙げられる。
の何れかで表される化合物(以下「保護基導入剤」と略記する。)とを反応させる方法が挙げられる。
下記実施例において、フェノール樹脂中間体中の環状フェノール樹脂中間体(A’)の含有量は、下記条件で測定したゲルパーミエーションクロマトグラフィー(GPC)のチャート図の面積比から算出した値である。
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」(8.0mmФ×300mm)+昭和電工株式会社製「Shodex KF802」(8.0mmФ×300mm)
+昭和電工株式会社製「Shodex KF803」(8.0mmФ×300mm)+昭和電工株式会社製「Shodex KF804」(8.0mmФ×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
(標準試料: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」
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120質量部、1―ナフトール36質量部、4−ヒドロキシベンズアルデヒド122質量部、1−ブタノール290質量部、95%硫酸1.7質量部を仕込み、100℃に昇温後12時間撹拌した。反応終了後、イオン交換水160質量部を加え、分液漏斗で下層よりpH1の水層を棄却した。有機層をイオン交換水160質量部で水洗し、これを7回繰り返した。最後の水洗で棄却される水層のpHは4であった。水洗後の有機層をエバポレータで加熱減圧乾燥しフェノール樹脂中間体(1)246質量部を得た。GPCチャート図から算出される、フェノール樹脂中間体(1)中の環状フェノール樹脂中間体(A’)含有量は74%であった。また、FD−MSスペクトルにて、下記構造式においてnの値が4である化合物の存在を示す992、1008、1024、1041のピークが検出された。フェノール樹脂中間体(1)のGPCチャートを図1に、FD−MSチャートを図2に示す。
製造例1において、1,6−ジヒドロキシナフタレン120質量部、1―ナフトール36質量部を、1,6−ジヒドロキシナフタレン90質量部、1―ナフトール72質量部に変更した以外は、製造例1と同様にしてフェノール樹脂中間体(2)237質量部を得た。GPCチャート図から算出される、フェノール樹脂中間体(2)中の環状フェノール樹脂中間体(A’)含有量は79%であった。また、FD−MSスペクトルにて、前記構造式においてnの値が4である化合物の存在を示す992、1008、1024、1041、1058のピークが検出された。フェノール樹脂中間体(2)のGPCチャートを図3に、FD−MSチャートを図4に示す。
製造例1において、1,6−ジヒドロキシナフタレン120質量部、1―ナフトール36質量部を、1,6−ジヒドロキシナフタレン40質量部、1―ナフトール108質量部に変更した以外は、製造例1と同様にしてフェノール樹脂中間体(3)231質量部を得た。GPCチャート図から算出される、フェノール樹脂中間体(3)中の環状フェノール樹脂中間体(A’)含有量は65%であった。また、FD−MSスペクトルにて、前記構造式においてnの値が4である化合物の存在を示す992、1008、1024、1041、1058のピークが検出された。フェノール樹脂中間体(3)のGPCチャートを図5に、FD−MSチャートを図6に示す。
冷却管を設置した1000ml3口フラスコに製造例1で合成したフェノール樹脂中間体(1)60質量部、保護基導入剤としてエチルビニルエーテル40質量部を仕込んだ後、1,3−ジオキソラン300質量部に溶解させた。35wt%塩酸水溶液0.1質量部を添加した後、25℃で4時間攪拌を継続し反応させた。反応中にメタノールで滴定を行い、メタノール溶解成分が消失し、水酸基のほぼすべてに保護基が導入されたことを確認した後、25wt%アンモニア水溶液1質量部を添加した。得られた溶液に水を加えて再沈殿操作を行い、沈殿物を濾別、真空乾燥を行い赤紫色粉末のノボラック型樹脂(1)71質量部を得た。
保護基導入剤として、エチルビニルエーテル40質量部に替えてジヒドロピラン44質量部とした以外は実施例1と同様の操作を行い、赤紫色粉末のノボラック型樹脂(2)68質量部を得た。
フェノール樹脂中間体(1)60質量部に替えてフェノール樹脂中間体(2)60質量部とした以外は実施例1と同様の操作を行い、赤紫色粉末のノボラック型樹脂(3)66質量部を得た。
フェノール樹脂中間体(1)60質量部に替えてフェノール樹脂中間体(3)60質量部とした以外は実施例1と同様の操作を行い、赤紫色粉末のボラック型樹脂(4)70質量部を得た。
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、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時間撹拌して反応させた。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、分液漏斗で水層を棄却した。水層のpHは1であった。有機層をイオン交換水160質量部で水洗し、これを7回繰り返した。最後の水洗で棄却される水層のpHは4であった。水洗後の有機層をエバポレータで加熱減圧乾燥し、粗生成物247質量部を得た。次いで、得られた粗生成物100質量部をメタノール100質量部に溶解した後、イオン交換水300質量部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、得られたろ過残渣を分取し、減圧乾燥器を用いて乾燥を行い、環状フェノール樹脂中間体(1’)60質量部を得た。
実施例1〜5、比較製造例1で得たノボラック型樹脂について、下記の要領で感光性組成物を調整し、各種評価を行った。結果を表1に示す。
ノボラック型樹脂19質量部をプロピレングリコールモノメチルエーテルアセテート80質量部に溶解させ、この溶液に光酸発生剤1gを加えて溶解させた。これを0.2μmのメンブランフィルターで濾過し、感光性組成物を得た。
光酸発生剤は和光純薬株式会社製「WPAG−336」[ジフェニル(4−メチルフェニル)スルフォニウムトリフルオロメタンスルフォネート]を用いた。
前記ノボラック型樹脂19gをプロピレングリコールモノメチルエーテルアセテート80gに溶解させ、これを0.2μmのメンブランフィルターで濾過し、耐熱性試験用組成物を得た。
先で得た感光性組成物を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秒乾燥させた。このウェハーを2枚用意し、一方を「露光なしサンプル」とした。他方を「露光有サンプル」としてghi線ランプ(ウシオ電機株式会社製「マルチライト」)を用いて100mJ/cm2のghi線を照射したのち、140℃、60秒間の条件で加熱処理を行った。
「露光なしサンプル」と「露光有サンプル」の両方をアルカリ現像液(2.38%水酸化テトラメチルアンモニウム水溶液)に60秒間浸漬した後、110℃のホットプレート上で60秒乾燥させた。各サンプルの現像液浸漬前後の膜厚を測定し、その差分を60で除した値をアルカリ現像性[ADR(nm/s)]とした。
先で得た感光性組成物を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秒乾燥させた。このウェハー上にラインアンドスペースが1:1であり、ライン幅が1〜10μmまで1μmごとに設定されたレジストパターン対応のマスクを密着させた後、ghi線ランプ(ウシオ電機株式会社製「マルチライト」)を用いてghi線を照射し、140℃、60秒間の条件で加熱処理を行った。次いで、アルカリ現像液(2.38%水酸化テトラメチルアンモニウム水溶液)に60秒間浸漬した後、110℃のホットプレート上で60秒乾燥させた。
ghi線露光量を30mJ/cm2から5mJ/cm2毎に増加させた場合の、ライン幅3μmを忠実に再現することのできる露光量(Eop露光量)を評価した。
先で得た感光性組成物を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秒乾燥させた。得られたウェハー上にフォトマスクを乗せ、先のアルカリ現像性評価の場合と同様の方法でghi線200mJ/cm2を照射し、アルカリ現像操作を行った。レーザーマイクロスコープ(株式会社キーエンス製「VK−X200」)を用いてパターン状態を確認し、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×として評価した。
先で得た耐熱性試験用組成物を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秒乾燥させた。得られたウェハーより樹脂分をかきとり、そのガラス転移温度(Tg)を測定した。ガラス転移温度(Tg)の測定は示差走査熱量計(DSC)(株式会社TAインスツルメント製「Q100」)を用いて、窒素雰囲気下、温度範囲−100〜200℃、昇温温度10℃/分の条件で行った。ガラス転移温度が170℃以上の場合を○、170℃未満の場合を×として評価した。
実施例1〜4、比較製造例1で得たノボラック型樹脂について、下記の要領で硬化性組成物を調整し、各種の評価試験を行った。結果を表2に示す。
ノボラック型樹脂16g、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」)4gをプロピレングリコールモノメチルエーテルアセテート30gに溶解させ、これを0.2μmのメンブランフィルターで濾過し、硬化性組成物を得た。
先で得た硬化性組成物を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秒乾燥させた。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、更に、350℃で120秒間加熱して、膜厚0.3μmの硬化塗膜月シリコンウェハーを得た。ウェハー上の硬化塗膜を、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 (9)
- 下記構造式(1)
で表される構造部位(α)であり、nは2〜10の整数である。]
で表される分子構造を有する環状ノボラック型樹脂(A)と、前記構造部位(α)を繰り返し単位として有する非環状ノボラック型樹脂(B)とを含有し、樹脂中に存在するXのうち少なくとも一つが3級アルキル基、アルコキシアルキル基、アシル基、アルコキシカルボニル基、ヘテロ原子含有環状炭化水素基、トリアルキルシリル基の何れかであり、樹脂中に存在する構造部位(α)のうち少なくとも一つはlが1である構造部位(α1)であり、少なくとも一つはlが2である構造部位(α2)であることを特徴とするノボラック型樹脂。 - ノボラック型樹脂中の前記環状ノボラック型樹脂(A)の含有率が30〜95%の範囲である請求項1記載のノボラック型樹脂。
- 前記構造式(2)中のR1が置換基を有していても良いアリール基である請求項1記載のノボラック型樹脂。
- 前記構造式(2)中のR1が、−OXで表される構造部位(Xは水素原子、3級アルキル基、アルコキシアルキル基、アシル基、アルコキシカルボニル基、ヘテロ原子含有環状炭化水素基、トリアルキルシリル基の何れかである)を有するアリール基である請求項1記載のノボラック型樹脂。
- 請求項1〜4の何れか一つに記載のノボラック型樹脂と光酸発生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膜。
- 請求項1〜4の何れか一つに記載のノボラック型樹脂と硬化剤とを含有する硬化性組成物。
- 請求項7記載の硬化性組成物の硬化物。
- 請求項7記載の硬化性組成物からなるレジスト膜。
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US10179828B2 (en) * | 2015-01-16 | 2019-01-15 | Dic Corporation | Curable composition for permanent resist films, and permanent resist film |
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