JP2022058159A - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 239000000178 monomer Substances 0.000 claims abstract description 52
- 239000000463 material Substances 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 7
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000001127 nanoimprint lithography Methods 0.000 claims description 7
- 230000001588 bifunctional effect Effects 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 238000005530 etching Methods 0.000 description 41
- 239000010410 layer Substances 0.000 description 32
- 239000000523 sample Substances 0.000 description 28
- 239000000460 chlorine Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001312 dry etching Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- -1 Irgacure 1173 Chemical compound 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DLBHMXBDKPROEG-UHFFFAOYSA-N [4-(hydroxymethyl)-1-bicyclo[2.2.2]octanyl]methanol Chemical compound C1CC2(CO)CCC1(CO)CC2 DLBHMXBDKPROEG-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
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- 238000011282 treatment Methods 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- DZYDNXOWKUPZMD-UHFFFAOYSA-N C(C=C)(=O)OC1CCCC1.C(C=C)(=O)OC1CCCC1 Chemical compound C(C=C)(=O)OC1CCCC1.C(C=C)(=O)OC1CCCC1 DZYDNXOWKUPZMD-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
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- G03F7/004—Photosensitive materials
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/20—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds unconjugated
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- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/22—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having three or more carbon-to-carbon double bonds
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
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- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
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Abstract
Description
式(2)のビシクロオクタンアクリレートモノマーの調製
25g量(1mol当量)のビシクロ[2.2.2]オクタン-1,4-ジメタノール(BCO-DM)を、25.5g(1.7mol当量)のトリエチルアミンを含む200mlのジクロロメタンに溶解した。得られた溶液を氷浴に入れ、0℃に冷却した。その後、50mlのジクロロメタンに溶解した20.3g(1.5mol当量)の塩化アクリロイルを、窒素雰囲気下で、撹拌しつつ、BCOD含有溶液にゆっくりと滴下した。塩化アクリロイルの添加後、反応溶液の温度を0℃で1時間保持した。その後、氷浴を除き、反応混合物を窒素下で更に24時間撹拌した。得られた白色の反応生成物が、式(2)のモノマー(本明細書中、ビシクロ[2.2.2]オクタン-1,4-ジメチルアクリレート(BCO-DA)ともいう)であり、ろ過により分離し、蒸留水で洗浄した。反応収率は80%であった。
20wt%の式(2)のビシクロオクタンジアクリレート(BCO-DA)、35wt%のBA、10wt%のIBOA、及び50wt%のA-NPGを含む硬化性組成物(試料1)を調製した。この組成物は更に、2wt%の光重合開始剤Irgacure TPO、3wt%のIrgacure 4265、及び3wt%の離型剤FS2000M2及びFS2000M1(Daniel Lab製)を含んでいた。最終的な組成物は、23℃で6.5mPa・sの粘度を有していた。
厚さ100nmの硬化性組成物の膜をシリコンウェハ上に堆積させた。この液膜に20mW/cm2の強度の紫外光を施し、この液膜を120秒間硬化させて完全に硬化させたが、これは2.4J/cm2の硬化エネルギー投与量に相当した。
粘度は、スピンドルサイズ#18で200rpmにてブルックフィールド粘度計LVDV-II+Proを用いて23℃で各試料について測定した。粘度試験のために、スピンドルヘッドを覆うのに十分な約6mL~7mLの試料液を試料チャンバに加えた。全ての粘度試験で、少なくとも3回の測定を行い、平均値を算出した。
BCO-DAの量が5wt%であり、DCP-A/DA(ジシクロペンチルアクリレート及びジシクロペンチルジアクリレートの混合物)を更に含むこと以外は、実施例2の試料S1と同様にして、硬化性組成物(試料S3)を調製した。試料S3の粘度は7.11cpsであった。試料S3の硬化膜を、比較組成物の試料S4の硬化膜と比較した。比較組成物S4は、BCO-DAを含まなかった。試料S4の粘度は7.15cpsであった。試料S3及びS4の正確な組成は、表2にまとめている。
Claims (20)
- 前記式(1)のモノマーは、二官能性アクリレートモノマーを含む、請求項1に記載の硬化性組成物。
- 前記式(1)のモノマーの量は、前記重合性材料の総重量に対して、少なくとも5wt%かつ50wt%以下である、請求項1~3のいずれか1項に記載の硬化性組成物。
- 前記重合性材料の量は、前記硬化性組成物の総重量に対して、少なくとも5wt%かつ98wt%以下である、請求項1~4のいずれか1項に記載の硬化性組成物。
- 前記重合性材料は、前記式(1)のモノマーとは異なる、少なくとも1種の第2のアクリレートモノマーを含む、請求項1~5のいずれか1項に記載の硬化性組成物。
- 前記少なくとも1種の第2のアクリレートモノマーは、ベンジルアクリレート(BA)、又はイソボルニルアクリレート(IBOA)、又はネオペンチルグリコールジアクリレート(A-NPG)、又はこれらの任意の組み合わせを含む、請求項6に記載の硬化性組成物。
- 前記組成物は、20mPa・s以下の粘度を有する、請求項1~7のいずれか1項に記載の硬化性組成物。
- 前記組成物は、15mPa・s以下の粘度を有する、請求項8に記載の硬化性組成物。
- 光重合開始剤を更に含む、請求項1~9のいずれか1項に記載の硬化性組成物。
- 前記硬化性組成物は、ナノインプリントリソグラフィープロセスにおけるレジストとしての使用に適合している、請求項1~10のいずれか1項に記載の硬化性組成物。
- 硬化後の前記硬化性組成物の大西パラメータは3.6以下である、請求項1~11のいずれか1項に記載の硬化性組成物。
- 基板と該基板を覆う硬化層とを含む積層体であって、前記硬化層が、請求項1~12のいずれか1項に記載の硬化性組成物から形成されている、積層体。
- 前記硬化層は、3.6以下の大西パラメータを有する、請求項13に記載の積層体。
- 前記硬化性組成物の粘度は、20mPa・s以下である、請求項15に記載の方法。
- 前記式(1)のモノマーの量は、前記重合性材料の総重量に対して、少なくとも5wt%かつ50wt%以下である、請求項15または16に記載の方法。
- 前記式(1)のモノマーの量は、前記重合性材料の総重量に対して、少なくとも5wt%かつ50wt%以下であり、前記硬化性組成物の粘度は、20mPa・s以下である、請求項19に記載の方法。
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