JP7097424B2 - 化合物、化合物の合成方法、ハードマスク組成物およびパターン形成方法 - Google Patents
化合物、化合物の合成方法、ハードマスク組成物およびパターン形成方法 Download PDFInfo
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- JP7097424B2 JP7097424B2 JP2020195855A JP2020195855A JP7097424B2 JP 7097424 B2 JP7097424 B2 JP 7097424B2 JP 2020195855 A JP2020195855 A JP 2020195855A JP 2020195855 A JP2020195855 A JP 2020195855A JP 7097424 B2 JP7097424 B2 JP 7097424B2
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- 239000000203 mixture Substances 0.000 title claims description 48
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- 238000001308 synthesis method Methods 0.000 title 1
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- 125000000217 alkyl group Chemical group 0.000 claims description 133
- 239000000126 substance Substances 0.000 claims description 106
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- 238000005530 etching Methods 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 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 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 230000005641 tunneling Effects 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
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- C01B32/15—Nano-sized carbon materials
- C01B32/182—Graphene
- C01B32/184—Preparation
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Description
R1およびR2は、それぞれ独立して、置換または非置換の炭素数3~20の分枝状のアルキル基であり、
R3は、それぞれ独立して、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~30のアルキニル基、置換もしくは非置換の炭素数6~30のアリール基、置換もしくは非置換の炭素数3~30のヘテロ環基、ハロゲン原子、シアノ基、またはこれらの組み合わせであり、
nは、0~3の整数である。
Rx~Rzは、それぞれ独立して、置換もしくは非置換の炭素数3~20の分枝状アルキル基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数6~30のアリール基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のシクロアルキル基、または少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のヘテロ環基である。
R1およびR2は、それぞれ独立して、置換または非置換の炭素数3~20の分枝状アルキル基であり、
R3は、それぞれ独立して、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~30のアルキニル基、置換もしくは非置換の炭素数6~30のアリール基、置換もしくは非置換の炭素数3~30のヘテロ環基、またはこれらの組み合わせであり、
nは、0~3の整数である。
Rx~Rzは、それぞれ独立して、置換もしくは非置換の炭素数3~20の分枝状アルキル基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数6~30のアリール基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のシクロアルキル基、または少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のヘテロ環基である。
R1およびR2は、それぞれ独立して、置換もしくは非置換の炭素数3~20の分枝状アルキル基であり、
R3は、それぞれ独立して、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~30のアルキニル基、置換もしくは非置換の炭素数6~30のアリール基、置換もしくは非置換の炭素数3~30のヘテロ環基、またはこれらの組み合わせであり、
nは、0~3の整数である。
A1およびA2は、それぞれ独立して、置換または非置換のフェニル基であり、
RxおよびRyは、それぞれ独立して、置換もしくは非置換の炭素数3~20の分枝状アルキル基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数6~30のアリール基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のシクロアルキル基、または少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のヘテロ環基である。
R1およびR2は、それぞれ独立して、置換または非置換の炭素数3~20の分枝状のアルキル基であり、
R3は、それぞれ独立して、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~30のアルキニル基、置換もしくは非置換の炭素数6~30のアリール基、置換もしくは非置換の炭素数3~30のヘテロ環基、ハロゲン原子、シアノ基、またはこれらの組み合わせであり、
nは、0~3の整数である。
Rx~Rzは、それぞれ独立して、置換もしくは非置換の炭素数3~20の分枝状アルキル基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数6~30のアリール基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のシクロアルキル基、または少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のヘテロ環基である。ここで、置換もしくは非置換の炭素数3~20の分枝状アルキル基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数6~30のアリール基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のシクロアルキル基、または少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のヘテロ環基は、前述の通りである。
Rx~Rzは、それぞれ独立して、置換もしくは非置換の炭素数3~20の分枝状アルキル基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数6~30のアリール基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のシクロアルキル基、または少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のヘテロ環基である。ここで、置換もしくは非置換の炭素数3~20の分枝状アルキル基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数6~30のアリール基、少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のシクロアルキル基、または少なくとも1つの置換もしくは非置換の炭素数3~20の分枝状アルキル基で置換された炭素数3~30のヘテロ環基は、前述の通りである。
A1およびA2は、それぞれ独立して、置換または非置換のフェニル基であり、
RxおよびRyの定義は、前述の通りである。
(合成例1)
真空オーブンで乾燥された1L丸底フラスコに攪拌子を入れ、1,2-ビス(3,5-ジ-ターシャリーブチルフェニル)エチン(1,2-bis(3,5-di-tert-butylphenyl)ethyne、40.3g、分子量:402.67)およびヨウ素(12.7g)を入れ、ジメチルスルホキシド(DMSO、0.5L)を入れた後、コンデンサを連結し、6時間還流した。その後、混合物をチオ硫酸ナトリウム 1M水溶液 0.5Lおよび酢酸エチル 1Lで順次に希釈し、蒸留水(1回1L、計3回)で抽出した。有機層を無水硫酸ナトリウムで乾燥しろ過した後に濃縮して、1,2-ビス(3,5-ジ-ターシャリーブチルフェニル)エタン-1,2-ジオン(39.5g)を得た。1,2-ビス(3,5-ジ-ターシャリーブチルフェニル)エタン-1,2-ジオンは、下記化学式1aで表される化合物である(収率91%、分子量:434.66、1H NMR(300MHz、CDCl3)δ(ppm):7.82(d、4JHH=1.8Hz、4H)、7.74(t、4JHH=1.8Hz、2H)、1.34(s、36H))。
真空オーブンで乾燥され、滴下ロートとコンデンサとを装着した1L丸底フラスコに攪拌子を入れ、合成例1で得られた化学式1aで表される化合物(39.5g)、1,3-ジフェニル-2-プロパノン(20.1g、分子量:210.28)、およびメタノール(700mL)を入れ、1時間還流しながら攪拌した。その後、水酸化カリウム(10.7g)をメタノール(100mL)に溶かした溶液を、滴下ロートを使用して30分間滴下した後、50分間還流しながら攪拌した。その後、混合物を常温に冷却させた後、生成された赤い沈殿物をろ過し、冷たいエタノール(1回300mL、計3回)で洗浄した後に乾燥して、3,4-ビス(3,5-ジ-ターシャリーブチルフェニル)-2,5-ジフェニルシクロペンタ-2,4-ジエン-1-オン(40.0g)を得た。3,4-ビス(3,5-ジ-ターシャリーブチルフェニル)-2,5-ジフェニルシクロペンタ-2,4-ジエン-1-オンは、下記化学式1bで表される化合物である(収率72%、分子量:608.91、1H-NMR(300MHz、CDCl3)δ(ppm):7.15-7.35(m、12H)、6.72(d、4JHH=1.8Hz、4H)、1.05(s、36H))。
コンデンサを装着した250mL丸底フラスコに攪拌子を入れ、1,3,5-トリエチニルベンゼン(1,3,5-Triethynylbenzene、分子量:150.18、1.64g)、合成例2で得られた上記化学式1bで表される化合物(20.0g)、およびPGMEA(プロピレングリコールモノメチルエーテルアセテート、100m)を入れた後、150℃で24時間攪拌しながら反応させた。その後、混合物を常温に冷却し、濃縮して当量の下記化学式1cで表される化合物(20.7g)を得た(分子量:1892.88、MALDI-TOF[M+H]+=1892.5154m/z)。
コンデンサを装着した250mL丸底フラスコに攪拌子を入れ、3,3’,5’,5’-テトラエチニルビフェニル(3,3’,5’,5’-Tetraethynylbiphenyl、2.06g、分子量:250.30)、合成例2で得られた上記化学式1bで表される化合物(20.0g)、およびPGMEA(100m)を入れた後、150℃で24時間攪拌しながら反応させた。その後、混合物を常温に冷却し、濃縮して当量の下記化学式1dで表される化合物(21.1g)を得た(分子量:2573.90、MALDI-TOF[M+H]+=2574.0427m/z)。
真空オーブンで乾燥された1L丸底フラスコに、合成例3で得られた上記化学式1cで表される化合物(10.0g)およびジクロロメタン(500mL)を入れ、氷浴に入れて攪拌した。フラスコに設置された滴下ロートに、塩化鉄(III)(25.7g)およびニトロメタン(nitromethane、200mL)で作った溶液を入れ、30分間滴下しながら攪拌した。滴下後、氷浴を除去し、追加的に2時間攪拌した。その後、混合物にメタノール(100mL)と水(100mL)とを入れて攪拌した後、混合物を濃縮した。濃縮された混合物を、酢酸エチル(1L)で希釈し、0.5N塩化水素(HCl)水溶液(1回1L、計2回)で洗浄し、水(1回1L、計5回)で洗浄した後、濃縮して当量の下記化学式1eで表される化合物(9.9g)を得た(分子量:1874.74、MALDI-TOF[M+H]+=1868.2833m/z)。
真空オーブンで乾燥された1L丸底フラスコに、合成例4で得られた上記化学式1dで表される化合物(10.0g)およびジクロロメタン(dichloromethane、500mL)を入れ、氷浴に入れて攪拌した。フラスコに設置された滴下ロートに、塩化鉄(III)(、31.5g)およびニトロメタン(nitromethane、200mL)で作った溶液を入れ、30分間滴下しながら攪拌した。滴下後、氷浴を除去し、追加的に2時間攪拌した。その後、混合物にメタノール(100mL)と水(100mL)とを入れて攪拌した後、混合物を濃縮した。濃縮された混合物を、酢酸エチル(1L)で希釈し、0.5N塩化水素(HCl)水溶液(1回1L、計2回)で洗浄し、水(1回1L、計5回)で洗浄した後、濃縮して当量の下記化学式1fで表される化合物(9.8g)を得た(MALDI-TOF[M+H]+=2479.6055m/z)。
コンデンサを装着した500mL二口丸底フラスコに、1-ヒドロキシピレン(1-hydroxypyrene、21.8g、0.10mol)、1-ナフトール(14.5g、0.10mol)、パラホルムアルデヒド(6.0g、0.2mol)、ジエチルスルフェート(15.4g、0.10mol)、およびPGMEA 115gを入れた後、110℃で5時間~48時間攪拌して重合反応を行い、重量平均分子量が1,000~1,500となった時点で反応を終了させた。重合反応終了後、常温まで徐々に冷却させ、酢酸エチル500mlで希釈し、蒸留水500mlで10回洗浄した。有機層を減圧濃縮した後、テトラヒドロフラン(THF、200ml)で希釈し、ヘキサン 1.5Lに徐々に滴下して沈殿物を得た。沈殿物をろ過した後、再びテトラヒドロフラン200mlに溶かし、ヘキサン 1.5Lに徐々に滴下して再び沈殿物を得た。沈殿物をろ過および乾燥後、下記化学式Aで表される構造単位を含む重合体を得た(Mw:1,500)。
1-ヒドロキシピレン(1-hydroxypyrene、21.8g、0.10mol)、1-ナフトール(14.5g、0.10mol)、パラホルムアルデヒド(6.0g、0.2mol)、ジエチルスルフェート(15.4g、0.10mol)、およびPGMEA(115g)の代わりに、4,4’-(9H-フルオレン-9-イリデン)ビスフェノール(4,4’-(9H-fluoren-9-ylidene)bisphenol、35.0g、0.10mol)、1,4-ビス(メトキシメチル)ベンゼン(1,4-bis(methoxymethyl)benzene、16.6g、0.10mol)、ジエチルスルフェート(15.4g、0.10mol)、およびPGMEA(134g)を使用したことを除いては、比較合成例1と同様の方法で、下記化学式Bで表される構造単位を含む重合体を得た(Mw:1,700)。
上記合成例3~6、比較合成例1、および比較合成例2で得られたそれぞれの化合物および重合体を、PGMEA、シクロヘキサノン、または1:10~10:1体積比のPGMEA/シクロヘキサノンなどの適切な溶媒に均一に溶かして、15質量%濃度の実施例1~4、比較例1、および比較例2のハードマスク組成物を製造した。
実施例1~4、比較例1、および比較例2で得られたハードマスク組成物を、それぞれシリコンウエハーにスピンコーティングした後、ホットプレート上で、530℃で2分間熱処理して、3,000~4,000Å厚さの有機膜を形成した。次いで、得られた有機膜にCFx混合ガス(100mT/600W/42CF4/18CHF3/600Ar/15O2)を使用して、100秒間乾式エッチングを行った後、有機膜の厚さを再び測定した。
Claims (5)
- 前記化学式2中のRzは、置換または非置換の炭素数3~20の分枝状アルキル基である、請求項1または2に記載の化合物。
- 請求項1~3のいずれか1項に記載の化合物および溶媒を含むハードマスク組成物。
- 材料層の上に、請求項4に記載のハードマスク組成物を塗布し熱処理してハードマスク層を形成する段階、
前記ハードマスク層の上にフォトレジスト層を形成する段階、
前記フォトレジスト層を露光および現像してフォトレジストパターンを形成する段階、
前記フォトレジストパターンを用いて前記ハードマスク層を選択的に除去し前記材料層の一部を露出する段階、ならびに
前記材料層の露出された部分をエッチングする段階、
を含む、パターン形成方法。
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