JPWO2015098594A1 - 第二アミノ基を有するノボラックポリマーを含むレジスト下層膜形成組成物 - Google Patents
第二アミノ基を有するノボラックポリマーを含むレジスト下層膜形成組成物 Download PDFInfo
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- JPWO2015098594A1 JPWO2015098594A1 JP2015554753A JP2015554753A JPWO2015098594A1 JP WO2015098594 A1 JPWO2015098594 A1 JP WO2015098594A1 JP 2015554753 A JP2015554753 A JP 2015554753A JP 2015554753 A JP2015554753 A JP 2015554753A JP WO2015098594 A1 JPWO2015098594 A1 JP WO2015098594A1
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- 239000011593 sulfur Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- G03F7/20—Exposure; Apparatus therefor
- G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
- G03F7/2059—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a scanning corpuscular radiation beam, e.g. an electron beam
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- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
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- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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Abstract
Description
第2観点として、ノボラックポリマーが式(1):
(式(1)中、R1は水素原子の置換基であって、ハロゲン基、ニトロ基、アミノ基、ヒドロキシ基、炭素数1乃至10のアルキル基、炭素数2乃至10のアルケニル基、炭素数6乃至40のアリール基、又はエーテル結合、ケトン結合、若しくはエステル結合を含んでいても良いそれらの組み合わせであり、R2は炭素数1乃至10のアルキル基、炭素数2乃至10のアルケニル基、炭素数6乃至40のアリール基、又はエーテル結合、ケトン結合、若しくはエステル結合を含んでいても良いそれらの組み合わせであり、R3は水素原子、又はハロゲン基、ニトロ基、アミノ基、ホルミル基、カルボキシル基、カルボン酸アルキルエステル基、ヒドロキシ基で置換されていても良い炭素数6乃至40のアリール基、又は複素環基であり、R4は水素原子、又はハロゲン基、ニトロ基、アミノ基、ホルミル基、カルボキシル基、カルボン酸アルキルエステル基、ヒドロキシ基で置換されていても良い炭素数1乃至10のアルキル基、炭素数6乃至40のアリール基、又は複素環基であり、R3とR4はそれらが結合する炭素原子と一緒になって環を形成していても良い。nは0又は1の整数であり、mはnが0のとき0から3までの整数であり、nが1のとき0から5までの整数である。)で示される単位構造を含むものである第1観点に記載のレジスト下層膜形成組成物、
第3観点として、n及びmがゼロであり、R2がメチル基又はベンジル基である第2観点に記載のレジスト下層膜形成組成物、
第4観点として、R3がフェニル基、ナフチル基、アントリル基、又はピレニル基であり、R4が水素原子である第2観点又は第3観点に記載のレジスト下層膜形成組成物、
第5観点として、更に架橋剤を含有する第1観点乃至第4観点のいずれか一つに記載のレジスト下層膜形成組成物、
第6観点として、更に酸及び/又は酸発生剤を含む第1観点乃至第5観点のいずれか一つに記載のレジスト下層膜形成組成物、
第7観点として、第1観点乃至第6観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜、
第8観点として、半導体基板上に第1観点乃至第6観点のいずれか一つに記載のレジスト下層膜形成組成物により下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法、及び
第9観点として、半導体基板上に第1観点乃至第6観点のいずれか一つに記載のレジスト下層膜形成組成物によりレジスト下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法である。
本発明において上記のリソグラフィー用レジスト下層膜形成組成物は上記ポリマーと溶剤を含む。そして、架橋剤と酸を含むことができ、必要に応じて酸発生剤、界面活性剤等の添加剤を含むことができる。この組成物の固形分は0.1乃至70質量%、または0.1乃至60質量%である。ここで、固形分はレジスト下層膜形成組成物から溶剤を除いた全成分の含有割合である。固形分中に上記ポリマーを1乃至100質量%、または1乃至99.9質量%、または50乃至99.9質量%、または50乃至95質量%、または50乃至90質量%の割合で含有することができる。
本発明に用いられるポリマーは、重量平均分子量が600乃至1000000、又は600乃至200000である。
式(1)中、R1は水素原子の置換基であって、ハロゲン基、ニトロ基、アミノ基、ヒドロキシ基、炭素数1乃至10のアルキル基、炭素数2乃至10のアルケニル基、炭素数6乃至40のアリール基、又はエーテル結合、ケトン結合、若しくはエステル結合を含んでいても良いそれらの組み合わせであり、R2は炭素数1乃至10のアルキル基、炭素数2乃至10のアルケニル基、炭素数6乃至40のアリール基、又はエーテル結合、ケトン結合、若しくはエステル結合を含んでいても良いそれらの組み合わせであり、R3は水素原子、又はハロゲン基、ニトロ基、アミノ基、ホルミル基、カルボキシル基、カルボン酸アルキルエステル基、ヒドロキシ基で置換されていても良い炭素数6乃至40のアリール基、又は複素環基であり、R4は水素原子、又はハロゲン基、ニトロ基、アミノ基、ホルミル基、カルボキシル基、カルボン酸アルキルエステル基、ヒドロキシ基で置換されていても良い炭素数1乃至10のアルキル基、炭素数6乃至40のアリール基、又は複素環基であり、R3とR4はそれらが結合する炭素原子と一緒になって環を形成していても良い。nは0又は1の整数であり、mはnが0のとき0から3までの整数であり、nが1のとき0から5までの整数である。
そして、R3がフェニル基、ナフチル基、アントリル基、又はピレニル基であり、R4が水素原子である場合の単位構造を用いることができる。さらに、R3とR4において、それらが結合する炭素原子と一緒になって形成する環は、例えばフルオレン環が挙げられる。
また、本発明のポリマーの製造に用いられるケトン類としてはジアリールケトン類であり、例えばジフェニルケトン、フェニルナフチルケトン、ジナフチルケトン、フェニルトリルケトン、ジトリルケトン、9−フルオレノン等が挙げられる。
上記縮合反応で用いられる酸触媒としては、例えば硫酸、リン酸、過塩素酸等の鉱酸類、p−トルエンスルホン酸、p−トルエンスルホン酸一水和物等の有機スルホン酸類、蟻酸、シュウ酸等のカルボン酸類が使用される。酸触媒の使用量は、使用する酸類の種類によって種々選択される。
通常、第二アミノ基を有する芳香族化合物100質量部に対して、酸触媒を0.001乃至10000質量部、好ましくは、0.01乃至1000質量部、より好ましくは0.1乃至100質量部の割合で加えることができる。
縮合時の反応温度は通常40℃乃至200℃である。反応時間は反応温度によって種々選択されるが、通常30分乃至50時間程度である。
以上のようにして得られる重合体の重量平均分子量Mwは、通常500乃至1000000、又は600乃至200000である。
式(4)中、R10及びR11はそれぞれ水素原子、炭素数1乃至10のアルキル基、又は炭素数6乃至20のアリール基であり、n10は1乃至4の整数であり、n11は1乃至(5−n10)の整数であり、(n10+n11)は2乃至5の整数を示す。
式(5)中、R12は水素原子又は炭素数1乃至10のアルキル基であり、R13は炭素数1乃至10のアルキル基であり、n12は1乃至4の整数であり、n13は0乃至(4−n12)であり、(n12+n13)は1乃至4の整数を示す。オリゴマー及びポリマーは繰り返し単位構造の数が2乃至100、又は2乃至50の範囲で用いることができる。
これらのアルキル基及びアリール基は、上記アルキル基及びアリール基を例示することができる。
架橋剤の添加量は、使用する塗布溶剤、使用する下地基板、要求される溶液粘度、要求される膜形状などにより変動するが、全固形分に対して0.001乃至80質量%、好ましくは0.01乃至50質量%、さらに好ましくは0.05乃至40質量%である。これら架橋剤は自己縮合による架橋反応を起こすこともあるが、本発明の上記のポリマー中に架橋性置換基が存在する場合は、それらの架橋性置換基と架橋反応を起こすことができる。
さらに、プロピレングリコールモノブチルエーテル、プロピレングリコールモノブチルエーテルアセテート等の高沸点溶剤を混合して使用することができる。これらの溶剤の中でプロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノブチルエーテル、乳酸エチル、乳酸ブチル、及びシクロヘキサノン等がレベリング性の向上に対して好ましい。
本発明におけるリソグラフィー用レジスト下層膜の上部に塗布されるフォトレジストとしてはネガ型、ポジ型いずれも使用でき、ノボラック樹脂と1,2−ナフトキノンジアジドスルホン酸エステルとからなるポジ型フォトレジスト、酸により分解してアルカリ溶解速度を上昇させる基を有するバインダーと光酸発生剤からなる化学増幅型フォトレジスト、アルカリ可溶性バインダーと酸により分解してフォトレジストのアルカリ溶解速度を上昇させる低分子化合物と光酸発生剤からなる化学増幅型フォトレジスト、酸により分解してアルカリ溶解速度を上昇させる基を有するバインダーと酸により分解してフォトレジストのアルカリ溶解速度を上昇させる低分子化合物と光酸発生剤からなる化学増幅型フォトレジスト、骨格にSi原子を有するフォトレジスト等があり、例えば、ロームアンドハーツ社製、商品名APEX−Eが挙げられる。
本発明では、半導体基板上に本発明のレジスト下層膜形成組成物により該レジスト下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンにより該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を経て半導体装置を製造することができる。
100mL四口フラスコにN−メチルアニリン(4.50g、0.042mol、東京化成工業(株)製)、1−ナフトアルデヒド(6.56g、0.042mol、東京化成工業(株)製)、メタンスルホン酸(1.21g、0.0126mol、関東化学(株)製)を加え、プロピレングリコールモノメチルエーテル(18.41g、関東化学(株)製)を仕込み撹拌し、120℃まで昇温し溶解させ重合を開始した。30時間後室温まで放冷後、メタノール(800g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、10時間乾燥し、目的とするポリマー(式(2−2)、以下PMA−NAと略す)4.2gを得た。
PMA−NAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは1800、多分散度Mw/Mnは1.48であった。
100mL四口フラスコにN−メチルアニリン(3.50g、0.033mol、東京化成工業(株)製)、1−ピレンカルボキシアルデヒド(7.52g、0.033mol、東京化成工業(株)製)、メタンスルホン酸(0.94g、0.0098mol、関東化学(株)製)を加え、プロピレングリコールモノメチルエーテル(17.95g、関東化学(株)製)を仕込み撹拌し、120℃まで昇温し溶解させ重合を開始した。30時間後室温まで放冷後、メタノール(800g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、10時間乾燥し、目的とするポリマー(式(2−7)、以下PMA−PcAと略す)7.6gを得た。
PMA−PcAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは1100、多分散度Mw/Mnは1.43であった。
100mL四口フラスコにN−ベンジルアニリン(8.00g、0.044mol、東京化成工業(株)製)、1−ナフトアルデヒド(6.82g、0.044mol、東京化成工業(株)製)、メタンスルホン酸(1.26g、0.0131mol、関東化学(株)製)を加え、プロピレングリコールモノメチルエーテルアセテート(24.12g、関東化学(株)製)を仕込み撹拌し、120℃まで昇温し溶解させ重合を開始した。30時間後室温まで放冷後、メタノール(800g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、10時間乾燥し、目的とするポリマー(式(3−2)、以下PPBA−NAと略す)6.8gを得た。
PPBA−NAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは1400、多分散度Mw/Mnは1.25であった。
100mL四口フラスコにN−ベンジルアニリン(8.00g、0.044mol、東京化成工業(株)製)、1−ピレンカルボキシアルデヒド(10.05g、0.044mol、東京化成工業(株)製)、メタンスルホン酸(1.26g、0.0131mol、関東化学(株)製)を加え、プロピレングリコールモノメチルエーテルアセテート(28.97g、関東化学(株)製)を仕込み撹拌し、120℃まで昇温し溶解させ重合を開始した。30時間後室温まで放冷後、メタノール(800g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、10時間乾燥し、目的とするポリマー(式(3−7)、以下PPBA−PcAと略す)10.8gを得た。
PPBA−PcAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは1300、多分散度Mw/Mnは1.25であった。
窒素下、100mL四口フラスコにカルバゾール(6.69g、0.040mol、東京化成工業(株)製)、9−フルオレノン(7.28g、0.040mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.76g、0.0040mol、東京化成工業(株)製)を加え、1,4−ジオキサン(6.69g、関東化学(株)製)を仕込み撹拌し、100℃まで昇温し溶解させ重合を開始した。24時間後60℃まで放冷後、クロロホルム(34g、関東化学(株)製)を加え希釈し、メタノール(168g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥し、目的とするポリマー(式(6−1)、以下PCzFLと略す)9.37gを得た。
PCzFLのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2800、多分散度Mw/Mnは1.77であった。
合成例1で得た樹脂2gに、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.006gを混合し、シクロヘキサノン8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例2で得た樹脂2gに、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.006gを混合し、シクロヘキサノン8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例3で得た樹脂2gに、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.006gを混合し、プロピレングリコールモノメチルエーテルアセテート8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例4で得た樹脂2gに、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.006gを混合し、シクロヘキサノン8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
市販のクレゾールノボラック樹脂(クレゾールとホルムアルデヒドを用いて得られたノボラック樹脂)2gに、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.006gを混合し、プロピレングリコールモノメチルエーテルアセテート8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
比較合成例1で得た樹脂2gに、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.006gを混合し、プロピレングリコールモノメチルエーテルアセテート8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
実施例1乃至4及び比較例1で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で400℃2分間焼成し、レジスト下層膜(膜厚0.30μm)を形成した。このレジスト下層膜をレジストに使用する溶剤、例えば乳酸エチル、ならびにプロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、シクロヘキサノンに浸漬し、それらの溶剤に不溶であることを確認した。
ドライエッチング速度の測定に用いたエッチャ−及びエッチングガスは以下のものを用いた。
ES401(日本サイエンティフィック製):CF4
実施例1乃至4及び比較例1で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で240℃1分間、または400℃2分間焼成し、レジスト下層膜(膜厚0.30μm)を形成した。エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定した。
また、同様にフェノ−ルノボラック樹脂(市販品、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2000、多分散度Mw/Mnは2.5)溶液を、スピンコーターを用いてシリコンウェハー上に塗布し、205℃1分間焼成して塗膜を形成した。エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定した。205℃1分間焼成して得られたフェノールノボラック樹脂膜(膜厚0.2μm)のエッチング速度を1.00とした時の実施例1乃至4及び比較例1のレジスト下層膜のドライエッチング速度との比較を行った。結果を表1に示した。速度比は(レジスト下層膜)/(フェノ−ルノボラック樹脂膜)のドライエッチング速度比である。
実施例1乃至4及び比較例2で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてホールウェハー上に塗布した。ホットプレート上で400℃2分間焼成し、レジスト下層膜(膜厚0.25μm)を形成した。ホールウェハーとして直径100nm、高さ400nmのホールパターンを用いた。
実施例1乃至4で調製されたレジスト下層膜形成組成物の溶液を、スピンコーターを用いてホールウェハー上に塗布し、400℃2分間の焼成を行った後の基板を切断し、電子顕微鏡で観察した図1乃至4の写真からは、ホール内部まで十分に充填されていることが分かる。
一方、比較例2で調製されたレジスト下層膜形成組成物の溶液を、スピンコーターを用いてホールウェハー上に塗布し、400℃2分間の焼成を行った後の基板を切断し、電子顕微鏡で観察した図5の写真からは、ホール内部にわずかではあるが部分的に空洞が存在していた。
Claims (9)
- 第二アミノ基を有する芳香族化合物とアルデヒド化合物との反応により得られるノボラックポリマーを含む、リソグラフィー工程に用いるレジスト下層膜形成組成物。
- ノボラックポリマーが式(1):
(式(1)中、R1は水素原子の置換基であって、ハロゲン基、ニトロ基、アミノ基、ヒドロキシ基、炭素数1乃至10のアルキル基、炭素数2乃至10のアルケニル基、炭素数6乃至40のアリール基、又はエーテル結合、ケトン結合、若しくはエステル結合を含んでいても良いそれらの組み合わせであり、R2は炭素数1乃至10のアルキル基、炭素数2乃至10のアルケニル基、炭素数6乃至40のアリール基、又はエーテル結合、ケトン結合、若しくはエステル結合を含んでいても良いそれらの組み合わせであり、R3は水素原子、又はハロゲン基、ニトロ基、アミノ基、ホルミル基、カルボキシル基、カルボン酸アルキルエステル基、ヒドロキシ基で置換されていても良い炭素数6乃至40のアリール基、又は複素環基であり、R4は水素原子、又はハロゲン基、ニトロ基、アミノ基、ホルミル基、カルボキシル基、カルボン酸アルキルエステル基、ヒドロキシ基で置換されていても良い炭素数1乃至10のアルキル基、炭素数6乃至40のアリール基、又は複素環基であり、R3とR4はそれらが結合する炭素原子と一緒になって環を形成していても良い。nは0又は1の整数であり、mはnが0のとき0から3までの整数であり、nが1のとき0から5までの整数である。)で示される単位構造を含むものである請求項1に記載のレジスト下層膜形成組成物。 - n及びmがゼロであり、R2がメチル基又はベンジル基である請求項2に記載のレジスト下層膜形成組成物。
- R3がフェニル基、ナフチル基、アントリル基、又はピレニル基であり、R4が水素原子である請求項2又は請求項3に記載のレジスト下層膜形成組成物。
- 更に架橋剤を含有する請求項1乃至請求項4のいずれか1項に記載のレジスト下層膜形成組成物。
- 更に酸及び/又は酸発生剤を含む請求項1乃至請求項5のいずれか1項に記載のレジスト下層膜形成組成物。
- 請求項1乃至請求項6のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜。
- 半導体基板上に請求項1乃至請求項6のいずれか1項に記載のレジスト下層膜形成組成物により下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 半導体基板上に請求項1乃至請求項6のいずれか1項に記載のレジスト下層膜形成組成物によりレジスト下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
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