JP5544242B2 - レジスト下層膜用芳香族環含有重合体、これを含むレジスト下層膜組成物、およびこの組成物を用いた素子のパターン形成方法 - Google Patents
レジスト下層膜用芳香族環含有重合体、これを含むレジスト下層膜組成物、およびこの組成物を用いた素子のパターン形成方法 Download PDFInfo
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- 229910052731 fluorine Inorganic materials 0.000 description 7
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 5
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- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
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- 125000005577 anthracene group Chemical group 0.000 description 2
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- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 150000007974 melamines Chemical class 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000005581 pyrene group Chemical group 0.000 description 2
- QKYIPVJKWYKQLX-UHFFFAOYSA-N pyrene-2,7-diol Chemical compound C1=C(O)C=C2C=CC3=CC(O)=CC4=CC=C1C2=C43 QKYIPVJKWYKQLX-UHFFFAOYSA-N 0.000 description 2
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- NJQJGRGGIUNVAB-UHFFFAOYSA-N 2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one Chemical compound BrC1=CC(Br)(Br)C=C(Br)C1=O NJQJGRGGIUNVAB-UHFFFAOYSA-N 0.000 description 1
- NXKOSHBFVWYVIH-UHFFFAOYSA-N 2-n-(butoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCCCOCNC1=NC(N)=NC(N)=N1 NXKOSHBFVWYVIH-UHFFFAOYSA-N 0.000 description 1
- KFVIYKFKUYBKTP-UHFFFAOYSA-N 2-n-(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCNC1=NC(N)=NC(N)=N1 KFVIYKFKUYBKTP-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- STOLYTNTPGXYRW-UHFFFAOYSA-N [nitro(phenyl)methyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC([N+]([O-])=O)C1=CC=CC=C1 STOLYTNTPGXYRW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000003667 anti-reflective effect Effects 0.000 description 1
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
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- 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
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- ZAADUWCLWTWDSZ-UHFFFAOYSA-N dichloro-dodecyl-methylsilane Chemical compound CCCCCCCCCCCC[Si](C)(Cl)Cl ZAADUWCLWTWDSZ-UHFFFAOYSA-N 0.000 description 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
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- 229940116333 ethyl lactate Drugs 0.000 description 1
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- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical class N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Silicon Polymers (AREA)
Description
コーティング工程、下層膜の厚さ、ベーキング温度、および時間は前記範囲に限定されることはなく、互いに異なる多様な形態で製造されてもよい。本発明が属する技術分野において通常の知識を有する者は、本発明の技術的な思想や必須の特徴を変更せずに他の具体的な形態で実施される可能性があることを理解することができるであろう。
機械撹拌機、冷却管、10Lのフラスコが設けられた反応器内で、9,9’−ビスフェノールフルオレン350.4g(1.0mol)、フェニルメチルジクロロシラン191.1g(1.0mol)およびトリエチルアミン202.4g(2.0mol)を3500gのトルエンに溶解した。この溶液を撹拌機で攪拌して60℃で10時間反応を実施した後に反応を終了した。
機械撹拌機、冷却管、10Lフラスコが設けられた反応器内で、9,9’−ビスフェノールフルオレン350.4g(1.0mol)、ジフェニルジクロロシラン253.2g(1.0mol)および、トリエチルアミン202.4g(2.0mol)を3500gのトルエンに溶解した。この溶液を撹拌機で攪拌して60℃で10時間反応を実施した後に反応を終了した。
機械撹拌機、冷却管、10Lのフラスコが設けられた反応器に、9,9−ビス(1−ナフトール)フルオレン450.5g(1.0mol)、ジメチルジクロロシラン129.1g(1.0mol)および、トリエチルアミン202.4g(2.0mol)を4000gのトルエンに溶解した。この溶液を撹拌機で攪拌して60℃で12時間反応を実施した後に反応を終了した。
機械撹拌機、冷却管、および10Lのフラスコが設けられた反応器内で、9,9−ビス(1−ナフトール)フルオレン450.5g(1.0mol)、ジフェニルジクロロシラン253.2g(1.0mol)および、トリエチルアミン202.4g(2.0mol)を4000gのトルエンに溶解した。この溶液を撹拌機で攪拌して60℃で12時間反応を実施した後に反応を終了した。
機械撹拌機、冷却管、および10Lのフラスコが設けられた反応器内で、9,9−ビス(1−ナフトール)フルオレン450.5g(1.0mol)、ジクロロドデシルメチルシラン283.4g(1.0mol)および、トリエチルアミン202.4g(2.0mol)を4000gのトルエンに溶解した。この溶液を撹拌機で攪拌して60℃で12時間反応を実施した後に反応を終了した。
実施例1〜4で製造した重合体をそれぞれ0.8gずつ計量して、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とする)9gに入れて溶解させた。この溶液を濾過し、それぞれ実施例5〜8のレジスト下層膜組成物とした。
実施例1〜4の重合体の代わりに比較例1の重合体を使用したことを除いては、実施例5〜9と同様にレジスト下層膜を形成した。形成された下層膜のnおよびkの値をそれぞれ求めて下記表1に示した。
<実施例9〜12>
実施例5〜8で製造したレジスト下層膜組成物をそれぞれ、SiNが塗布されたシリコンウエハ上に、スピンコーティング法によってコーティングし、60秒間400℃でベーキングして厚さ2500Åの下層膜を形成した。
実施例5〜8のレジスト下層膜組成物の代わりに比較例2のレジスト下層膜組成物を用いたことを除いては、実施例9〜12と同じ過程でパターン化された試片を製造してパターンのELマージン、DoFマージン、パターンプロファイルの観察結果をそれぞれ求めた。その結果を下記表2に示した。
実施例5〜8でパターン化された試片を、CHF3およびCF4混合ガスを用いて下層膜に対するドライエッチングを行い、続いて混合比を異にしたCHF3およびCF4混合ガスを用いて、シリコンナイトライドに対するドライエッチングを再び行った。
比較例3で製造されたパターン化された試片を用いたことを除いては、実施例13〜16と同様にしてエッチングを行った後に、断面を観察し、その結果を下記表3に示した。
Claims (11)
- 下記化学式(1)で表示される繰り返し単位:
前記Aは下記化学式(1a):
で表された芳香族化合物から誘導された作用基である、
を含むレジスト下層膜用芳香族環含有重合体。 - 前記ヘテロ原子はN、O、S、またはPである請求項1に記載のレジスト下層膜用芳香族環含有重合体。
- 前記芳香族環含有重合体は重量平均分子量が2,000〜20,000である請求項1または2に記載のレジスト下層膜用芳香族環含有重合体。
- (a)下記化学式(1)で表示される繰り返し単位:
前記Aは下記化学式(1a)および化学式(1b):
のうちのいずれか1つの化学式で表された芳香族化合物から誘導された作用基である、
を含む芳香族環含有重合体;および
(b)有機溶媒
を含むレジスト下層膜組成物。 - 前記(a)芳香族環含有重合体の含有量は1〜20質量%であり、前記(b)有機溶媒の含有量は80〜99質量%である請求項4に記載のレジスト下層膜組成物。
- 前記レジスト下層膜組成物は界面活性剤をさらに含む請求項4または5に記載のレジスト下層膜組成物。
- 前記レジスト下層膜組成物は架橋成分をさらに含む請求項4〜6のいずれか一項に記載のレジスト下層膜組成物。
- (a)基板上に材料層を形成する段階;
(b)前記材料層上に請求項4〜7のいずれか一項に記載のレジスト下層膜組成物を用いてレジスト下層膜を形成する段階;
(c)前記レジスト下層膜上にレジスト層を形成する段階;
(d)前記レジスト層が形成された基板を露光する段階;
(e)前記露光された基板を現像する段階;および
(f)前記現像した後の基板をエッチングする段階
を含む素子のパターン形成方法。 - 前記(c)レジスト層を形成する段階の前にシリコン含有レジスト下層膜を形成させる段階をさらに含む請求項8に記載の素子のパターン形成方法。
- 前記シリコン含有レジスト下層膜を形成させる段階後、前記(c)レジスト層を形成する段階の前に反射防止層を形成する段階をさらに含む請求項9に記載の素子のパターン形成方法。
- 請求項8〜10のいずれか一項に記載の素子のパターン形成方法を用いた半導体集積回路デバイスの製造方法。
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