JP2010049247A - レジストパターン微細化組成物及びレジストパターン形成方法 - Google Patents
レジストパターン微細化組成物及びレジストパターン形成方法 Download PDFInfo
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- JP2010049247A JP2010049247A JP2009173067A JP2009173067A JP2010049247A JP 2010049247 A JP2010049247 A JP 2010049247A JP 2009173067 A JP2009173067 A JP 2009173067A JP 2009173067 A JP2009173067 A JP 2009173067A JP 2010049247 A JP2010049247 A JP 2010049247A
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- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 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
- 239000013638 trimer Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
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- 229960000604 valproic acid Drugs 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
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Abstract
【解決手段】感放射線性樹脂組成物を用いて形成したレジストパターン上に、レジストパターン微細化組成物を塗布し、ベーク後、洗浄してレジストパターンを微細化する工程、を含むレジストパターン形成方法で用いられる、酸性低分子化合物と、レジストパターンを溶解しない溶媒と、を含有するレジストパターン微細化組成物を提供する。
【選択図】なし
Description
本発明のレジストパターン微細化組成物は、後述する本発明のレジストパターン形成方法において、レジストパターンを微細化するために用いられるものであり、酸性低分子化合物と、レジストパターンを溶解しない溶媒と、を含有するものである。
酸性低分子化合物としては、カルボキシル基、スルホ基、及びスルホンイミド基からなる群より選択される少なくとも一種の官能基を有する低分子化合物であることが好ましい。
カルボキシル基を有する低分子化合物の具体例としては、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、ウンデカン酸、ラウリル酸、トリデカン酸、ミリスチン酸、ペンタデカン酸、パルミチン酸、ヘプタデカン酸、ステアリン酸、2−メチルプロパン酸、2−エチルブタン酸、2−メチルブタン酸、3−メチルブタン酸、2,2−ジメチルブタン酸、tert−ブチル酢酸、(±)−2−メチルペンタン酸、2−プロピルペンタン酸、3−メチルペンタン酸、4−メチルペンタン酸、2−メチルヘキサン酸、(±)−2−エチルヘキサン酸、2−メチルヘプタン酸、4−メチルオクタン酸、ジフルオロ酢酸、トリフルオロ酢酸、ペンタフルオロプロパン酸、ヘプタフルオロブタン酸、10−ヒドロキシデカン酸、12−ヒドロキシドデカン酸、12−ヒドロキシステアリン酸、(−)−メントキシ酢酸、チオール酢酸、チオピバリン酸、(メチルチオ)酢酸、チオジグリコール酸、2,2’,2’’,2’’’−[1,2−エタンジイリデンテトラキス(チオ)]テトラキス酢酸、(±)−3−メチル−2−オキソペンタン酸、5−オキソヘキサン酸、6−オキソヘプタン酸、シクロペンタンカルボン酸、シクロペンチル酢酸、3−シクロペンチルプロピオン酸、シクロヘキシル酢酸、ジシクロヘキシル酢酸、シクロヘキサンプロピオン酸、シクロヘキサンブタン酸、シクロヘキサンペンタン酸、(±)−2−メチル−1−シクロヘキサンカルボン酸、(±)−3−メチル−1−シクロヘキサンカルボン酸、4−メチルシクロヘキサンカルボン酸、4−tert−ブチルシクロヘキサンカルボン酸、trans−4−ペンチルシクロヘキサンカルボン酸、4−メチルシクロヘキサン酢酸、3−メトキシシクロヘキサンカルボン酸、4−メトキシシクロヘキサンカルボン酸、シクロヘプタンカルボン酸、2−ノルボルナン酢酸、[1R−(2−endo,3−exo)]−3−ヒドロキシ−4,7,7−トリメチルビシクロ[2.2.1]ヘプタン−2−酢酸、(+)−カンファーカルボン酸、(−)−カンファーカルボン酸、cis−ビシクロ[3.3.0]オクタン−2−カルボン酸、アンチ−3−オキソトリシクロ[2.2.1.02,6]ヘプタン−7−カルボン酸、3−アダマンタンカルボン酸、1−アダマンタンカルボン酸、1−アダマンタン酢酸、3−メチル−1−アダマンタン酢酸、(1S,3R)−(−)−カンファリックアシッド、安息香酸、フェニル酢酸、2−フェニルプロピオン酸、3−フェニルプロピオン酸、α−フルオロフェニル酢酸、3−フェノキシプロピオン酸、(±)−2−フェノキシプロピオン酸、(±)−α−メトキシフェニル酢酸、o−トリル酢酸、1,2−フェニレンジ酢酸、1,2,3,4−テトラヒドロ−2−ナフトイックアシッド、(α,α,α−トリフルオロ−o−トリル)酢酸、2−フルオロフェニル酢酸、2−メトキシフェニル酢酸、2−ニトロフェニル酢酸、3−(2−ニトロフェニル)−2−オキソプロパン酸、(α,α,α−トリフルオロ−m−トリル)酢酸、3−ニトロフェニル酢酸、3−フルオロフェニル酢酸、4−フルオロフェニル酢酸、(α,α,α−トリフルオロ−p−トリル)酢酸、4−ニトロフェニル酢酸、4−フルオロフェノキシ酢酸、2,6−ジフルオロフェニル酢酸、2,4−ジフルオロフェニル酢酸、2,5−ジフルオロフェニル酢酸、3,4−ジフルオロフェニル酢酸、3,5−ジフルオロフェニル酢酸、3,5−ビス(トリフルオロメチル)フェニル酢酸、3−フルオロ−4−ヒドロキシフェニル酢酸、(2,5−ジメトキシフェニル)酢酸、4−ヒドロキシ−3−ニトロフェニル酢酸、2,3,4,5,6−ペンタフルオロフェニル酢酸、1−ナフチル酢酸、2−ナフチル酢酸、(1−ナフトキシ)酢酸、(2−ナフトキシ)酢酸、2−フルオロ安息香酸、2−トリフルオロメチル安息香酸、2−ニトロ安息香酸、3−フルオロ安息香酸、3−トリフルオロメチル安息香酸、3−メトキシ安息香酸、4−フルオロ安息香酸、4−トリフルオロメチル安息香酸、4−ニトロ安息香酸、3−フルオロ−2−メチル安息香酸、2,3−ジフルオロ安息香酸、2,6−ジフルオロ安息香酸、2−フルオロ−6−トリフルオロメチル安息香酸、2−フルオロ−3−トリフルオロメチル安息香酸、2,6−ビス(トリフルオロメチル)安息香酸、2−メチル−6−ニトロ安息香酸、3−メチル−2−ニトロ安息香酸、2−メチル−3−ニトロ安息香酸、5−フルオロ−2−メチル安息香酸、3−フルオロ−4−メチル安息香酸、2,4−ビス(トリフルオロメチル)安息香酸、2,5−ビス(トリフルオロメチル)安息香酸、2,4−ジフルオロ安息香酸、3,4−ジフルオロ安息香酸、2−フルオロ−4−トリフルオロメチル安息香酸、2,5−ジフルオロ安息香酸、3−フルオロ−4−メトキシ安息香酸、5−メチル−2−ニトロ安息香酸、4−メチル−3−ニトロ安息香酸、3−メチル−4−ニトロ安息香酸、2−メチル−5−ニトロ安息香酸、2−フルオロ−5−ニトロ安息香酸、4−フルオロ−3−ニトロ安息香酸、4−メトキシ−3−ニトロ安息香酸、3−メトキシ−4−ニトロ安息香酸、3−ヒドロキシ−4−ニトロ安息香酸、2−ヒドロキシ−5−ニトロ安息香酸、2,4−ジニトロ安息香酸、3,4−ジニトロ安息香酸、3,5−ジフルオロ安息香酸、3,5−ビス(トリフルオロメチル)安息香酸、3,5−ジニトロ安息香酸、2,3,4−トリフルオロ安息香酸、2,3,6−トリフルオロ安息香酸、2,4,6−トリフルオロ安息香酸、3,4,5−トリフルオロ安息香酸、4−メチル−3,5−ジニトロ安息香酸、4−ヒドロキシ−3,5−ジニトロ安息香酸、3,5−ジニトロサリチル酸、2,4,5−トリフルオロ安息香酸、2,3,4,5−テトラフルオロ安息香酸、2,3,5,6−テトラフルオロ安息香酸、2,3,5,6−テトラフルオロ−4−メチル安息香酸、ペンタフルオロ安息香酸、2,3,4,5,6−ペンタフルオロフェノキシ酢酸、1−ナフタレンカルボン酸、2−ナフタレンカルボン酸、4−フルオロ−1−ナフタレンカルボン酸、1−ヒドロキシ−2−ナフタレンカルボン酸、2−ヒドロキシ−1−ナフタレンカルボン酸、3−ヒドロキシ−2−ナフタレンカルボン酸、1,4−ジヒドロキシ−2−ナフタレンカルボン酸、3,5−ジヒドロキシ−2−ナフタレンカルボン酸、(メタ)アクリル酸、クロトン酸、ケイ皮酸、アトロパ酸、3−アセチルオキシ(メタ)アクリル酸、3−ベンゾイルオキシ(メタ)アクリル酸、α−メトキシアクリル酸、3−シクロヘキシル(メタ)アクリル酸等のモノカルボン酸類;
スルホ基を有する低分子化合物の具体例としては、メタンスルホン酸、エタンスルホン酸、タウリン、3−[(1,1−ジメチル−2−ヒドロキシエチル)アミノ]−2−ヒドロキシ−1−プロパンスルホン酸、3−[ビス(2−ヒドロキシエチル)アミノ]−2−ヒドロキシ−1−プロパンスルホン酸、(1R)−(−)−10−カンファースルホン酸、(1S)−(+)−10−カンファースルホン酸、トリフルオロメタンスルホン酸、パーフルオロブタンスルホン酸、パーフルオロオクタンスルホン酸、(メチルアミノ)スルホン酸、(ブチルアミノ)スルホン酸、1,1,2,2−テトラフルオロ−2−(テトラシクロ[6.2.1.13,6.02,7]ドデカン−8−イル)エタンスルホン酸、1,1−ジフルオロ−2−(テトラシクロ[6.2.1.13,6.02,7]ドデカン−8−イル)エタンスルホン酸、ビニルスルホン酸、アリルスルホン酸、2−(メタ)アクリルアミド−2−メチル−1−プロパンスルホン酸、4−ビニル−1−ベンゼンスルホン酸等を挙げることができる。
スルホンイミド基を有する低分子化合物の具体例としては、ビス(トリフルオロメタンスルホニル)イミド、ビス(ヘキサフルオロエタンスルホニル)イミド、ビス(ヘプタフルオロプロパンスルホニル)イミド、ビス(ノナフルオロブタンスルホニル)イミド、シクロ−ヘキサフルオロプロパン−1,3−ビス(スルホニル)イミド等のペルフルオロアルキルスルホン酸イミドを挙げる事ができる。
溶媒としては、レジストパターンを溶解しない溶媒であり、フォトレジスト膜上に塗布するに際し、フォトレジスト膜とインターミキシングを起こさない溶媒であれば、特に制限なく使用することができる。
炭素数1〜12の1価のアルコールとしては、炭素数1〜12の直鎖状又は分岐状のアルキル由来のアルコールであることが好ましく、炭素数1〜8の直鎖状又は分岐状のアルキル由来のアルコールであることが更に好ましい。このような1価のアルコールとしては、1−プロパノール、イソプロピルアルコール、1−ブタノール、2−ブタノール、t−ブチルアルコール、1−ペンタノール、2−ペンタノール、3−ペンタノール、2−メチル−1−ブタノール、3−メチル−1−ブタノール、3−メチル−2−ブタノール、1−ヘキサノール、2−ヘキサノール、3−ヘキサノール、2−メチル−1−ペンタノール、2−メチル−2−ペンタノール、2−メチル−3−ペンタノール、3−メチル−1−ペンタノール、3−メチル−2−ペンタノール、3−メチル−3−ペンタノール、4−メチル−1−ペンタノール、4−メチル−2−ペンタノール、1−ヘプタノール、2−ヘプタノール、2−メチル−2−ヘプタノール、2−メチル−3−ヘプタノール等を挙げることができる。
炭素数1〜10のアルキル基を有するエーテルの具体例としては、ジプロピルエーテル、ジイソプロピルエーテル、ブチルメチルエーテル、ブチルエチルエーテル、ブチルプロピルエーテル、ジブチルエーテル、ジイソブチルエーテル、tert−ブチルメチルエーテル、tert−ブチルエチルエーテル、tert−ブチルプロピルエーテル、ジ−tert−ブチルエーテル、ジペンチルエーテル、ジイソアミルエーテル、シクロペンチルメチルエーテル、シクロヘキシルメチルエーテル、シクロペンチルエチルエーテル、シクロヘキシルエチルエーテル、シクロペンチルプロピルエーテル、シクロペンチル−2−プロピルエーテル、シクロヘキシルプロピルエーテル、シクロヘキシル−2−プロピルエーテル、シクロペンチルブチルエーテル、シクロペンチル−tert−ブチルエーテル、シクロヘキシルブチルエーテル、シクロヘキシル−tert−ブチルエーテル等を挙げることができる。
炭素数6〜12の直鎖状、分岐状、又は環状の飽和炭化水素の具体例としては、オクタン、イソオクタン、ノナン、デカン、メチルシクロヘキサン、デカリン等を挙げることができる。
芳香族炭化水素類の具体例としては、キシレン、アミルベンゼン、エチルベンゼン、ジエチルベンゼン、クメン、sec−ブチルベンゼン等を挙げることができる。
テルペン化合物の具体例としては、サイメン、ジペンテン等を挙げることができる。
レジストパターン微細化組成物をフォトレジスト膜上に塗布する際の塗布性を調整する目的で、溶媒は、上述した溶媒以外に他の溶媒を含んでも良い。前記他の溶媒としては、フォトレジスト膜を浸食せず、かつレジストパターン微細化組成物を均一に塗布する作用があるものであれば、特に制限なく用いることができる。
本発明のレジストパターン微細化組成物には、塗布性、消泡性、レベリング性等を向上させる目的で界面活性剤を更に含有させることができる。
本発明のレジストパターン形成方法は、感放射線性樹脂組成物を用いて形成したレジストパターン上に、前述の本発明のレジストパターン微細化組成物を塗布し、ベーク後、洗浄してレジストパターンを微細化する工程、を含む方法である。
図1は、本発明に係るレジストパターン形成方法における、レジストパターンを形成した後の状態の一例を示す模式図である。レジストパターンは、例えば、図1に示すように、基板10上に感放射線性樹脂組成物を用いてレジスト層を形成し、形成したレジスト層を、必要に応じて液浸媒体を用いて、マスクを介して選択的に露光した後、現像することにより形成することができる。
レジスト層は、後述する感放射線性樹脂組成物を溶剤に溶解させて調製した樹脂組成物溶液を、回転塗布、流延塗布、ロール塗布等の適宜の塗布手段によって、例えば、シリコンウェハ、二酸化シリコンで被覆されたウェハ等の基板10上に、所定の膜厚となるように塗布することにより、フォトレジスト膜を形成し、その後、PBすることにより塗膜中の溶剤を揮発させて形成することができる。
露光は、形成したレジスト層を、必要に応じて水等の液浸媒体を用い、所定のパターンを有するマスクを介して、放射線を照射することにより行う。
露光されたレジスト層を現像することにより、線幅がW1であるレジストパターン1を形成することができる。現像に使用される現像液の具体例としては、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、けい酸ナトリウム、メタけい酸ナトリウム、アンモニア、エチルアミン、n−プロピルアミン、ジエチルアミン、ジ−n−プロピルアミン、トリエチルアミン、メチルジエチルアミン、エチルジメチルアミン、トリエタノールアミン、テトラメチルアンモニウムヒドロキシド、ピロール、ピペリジン、コリン、1,8−ジアザビシクロ−[5.4.0]−7−ウンデセン、1,5−ジアザビシクロ−[4.3.0]−5−ノネン等のアルカリ性化合物の少なくとも一種を溶解したアルカリ性水溶液が好ましい。なお、アルカリ性水溶液の濃度としては、10質量%以下であることが好ましい。アルカリ性水溶液の濃度が10質量%超であると、非露光部も現像液に溶解するおそれがある。
図2は、本発明に係るレジストパターン形成方法における、レジストパターン微細化組成物を塗布し、ベークした後の状態の一例を示す模式図である。また、図3は、本発明に係るレジストパターン形成方法における、レジストパターンを微細化した後の状態の一例を示す模式図である。レジストパターンの微細化は、例えば、レジストパターン1上に、前述した本発明のレジストパターン微細化組成物を塗布し、ベーク後、洗浄することにより行うことができる。
感放射線性樹脂組成物は、化学増幅型レジストとして有用である。化学増幅型レジストにおいては、露光により酸発生剤から発生した酸の作用によって、樹脂成分中の酸解離性基が解離して、カルボキシル基を生じ、その結果、レジストの露光部がアルカリ現像液に対する溶解性が高くなり、この露光部がアルカリ現像液によって溶解、除去され、ポジ型のレジストパターンが得られる。
樹脂(A)は、酸の作用によりアルカリ可溶性となる樹脂である。
樹脂(A)は、酸の作用によりアルカリ可溶性となるものである。即ち、樹脂(A)は、酸の作用によりアルカリ可溶性を発現する構造を有する繰り返し単位を含む樹脂である。このような繰り返し単位として、下記一般式(1)で表される基を有する繰り返し単位(以下、「繰り返し単位(1)」と記載する)が好ましい。
樹脂(A)は、ラジカル重合等の常法に従って調製することができるが、好適な調製方法として、各単量体とラジカル開始剤を含有する反応溶液を、反応溶媒又は単量体を含有する反応溶液に滴下して重合反応させる方法、各単量体を含有する反応溶液とラジカル開始剤を含有する反応溶液とを、各々別々に、反応溶媒又は単量体を含有する反応溶液に滴下して重合反応させる方法、各単量体を各々別々に含有する反応溶液とラジカル開始剤を含有する反応溶液とを、各々別々に、反応溶媒又は単量体を含有する反応溶液に滴下して重合反応させる方法等を挙げることができる。
樹脂(A)のMwは、特に限定されないが、1,000〜100,000であることが好ましく、1,000〜30,000であることが更に好ましく、1,000〜20,000であることが特に好ましい。樹脂(A)のMwが1,000未満であると、レジストとしたときの耐熱性が低下する傾向にある。一方、樹脂(A)のMwが100,000超であると、レジストとした際の現像性が低下する傾向にある。
感放射線性樹脂組成物に含有される感放射線性酸発生剤(B)(以下、単に「酸発生剤(B)」と記載する)は、露光により酸を発生するものであり、光酸発生剤として機能する。酸発生剤(B)は、露光により発生した酸によって、樹脂(A)中に存在する酸解離性基を解離させ(保護基を脱離させ)、樹脂(A)をアルカリ可溶性とする。その結果、レジスト膜の露光部がアルカリ現像液に易溶性となり、現像することによりポジ型のレジストパターンが形成される。
酸拡散制御剤(C)は、露光により酸発生剤(B)から生じる酸のレジスト膜中における拡散現象を制御し、非露光領域における好ましくない化学反応を抑制する成分である。
このような酸拡散制御剤(C)を含有することにより、感放射線性樹脂組成物の貯蔵安定性が向上し、またレジストとしての解像度が更に向上するとともに、露光から露光後の加熱処理までの引き置き時間(PED)の変動によるレジストパターンの線幅変化を抑えることができ、プロセス安定性に極めて優れた組成物を得ることができる。
酸拡散制御剤(C)として使用できる3級アミン化合物の具体例としては、トリエチルアミン、トリ−n−プロピルアミン、トリ−n−ブチルアミン、トリ−n−ペンチルアミン、トリ−n−ヘキシルアミン、トリ−n−ヘプチルアミン、トリ−n−オクチルアミン、シクロヘキシルジメチルアミン、ジシクロヘキシルメチルアミン、トリシクロヘキシルアミン等のトリ(シクロ)アルキルアミン類等を挙げることができる。
酸拡散制御剤(C)として使用できる4級アンモニウムヒドロキシド化合物の具体例としては、テトラ−n−プロピルアンモニウムヒドロキシド、テトラ−n−ブチルアンモニウムヒドロキシド等を挙げることができる。
酸拡散制御剤(C)として使用できる含窒素複素環化合物の具体例としては、ピリジン、2−メチルピリジン、4−メチルピリジン、2−エチルピリジン、4−エチルピリジン、2−フェニルピリジン、4−フェニルピリジン、2−メチル−4−フェニルピリジン、ニコチン、ニコチン酸、ニコチン酸アミド、キノリン、4−ヒドロキシキノリン、8−オキシキノリン、アクリジン等のピリジン類;ピペラジン、1−(2−ヒドロキシエチル)ピペラジン等のピペラジン類の他、ピラジン、ピラゾール、ピリダジン、キノザリン、プリン、ピロリジン、ピペリジン、3−ピペリジノ−1,2−プロパンジオール、モルホリン、4−メチルモルホリン、1,4−ジメチルピペラジン、1,4−ジアザビシクロ[2.2.2]オクタン、イミダゾール、4−メチルイミダゾール、1−ベンジル−2−メチルイミダゾール、4−メチル−2−フェニルイミダゾール、ベンズイミダゾール、2−フェニルベンズイミダゾール等を挙げることができる。
酸拡散制御剤(C)として使用できるその他の含窒素化合物の具体例としては、アニリン、N−メチルアニリン、N,N−ジメチルアニリン、2−メチルアニリン、3−メチルアニリン、4−メチルアニリン、4−ニトロアニリン、2,6−ジメチルアニリン、2,6−ジイソプロピルアニリン等の芳香族アミン類;トリエタノールアミン、N,N−ジ(ヒドロキシエチル)アニリン等のアルカノールアミン類;N,N,N’,N’−テトラメチルエチレンジアミン、N,N,N’,N’−テトラキス(2−ヒドロキシプロピル)エチレンジアミン、1,3−ビス[1−(4−アミノフェニル)−1−メチルエチル]ベンゼンテトラメチレンジアミン、ビス(2−ジメチルアミノエチル)エーテル、ビス(2−ジエチルアミノエチル)エーテル等を挙げることができる。
感放射線性樹脂組成物は、必要に応じて、脂環式骨格含有添加剤(d1)、界面活性剤(d2)、増感剤(d3)等の各種の添加剤(D)を含有することができる。これら各種の添加剤(D)の含有割合は、その目的に応じて適宜選定することができる。
脂環式骨格含有添加剤(d1)は、ドライエッチング耐性、パターン形状、基板との接着性等を更に改善する作用を示す成分である。
界面活性剤(d2)は、塗布性、ストリエーションの抑制、現像性等を改善する作用を示す成分である。
増感剤(d3)は、放射線のエネルギーを吸収して、そのエネルギーを酸発生剤(B)に伝達し、酸の生成量を増加させる作用を示すものであり、感放射線性樹脂組成物のみかけの感度を向上させる効果を有する。
溶剤(E)としては、樹脂(A)、酸発生剤(B)を溶解しうる溶剤であれば、特に限定されるものではない。なお、感放射線性樹脂組成物が酸拡散制御剤(C)及び添加剤(D)を更に含有する場合には、酸拡散制御剤(C)及び添加剤(D)も溶解しうる溶剤であることが好ましい。
東ソー社製GPCカラム(G2000HXL2本、G3000HXL1本、G4000HXL1本)を用い、流量1.0mL/min、溶出溶剤テトラヒドロフラン、カラム温度40℃の分析条件で、ゲルパーミエーションクロマトグラフィ(GPC)により、単分散ポリスチレンを標準として測定した。
レジストパターン微細化組成物を塗布する前の線幅が75nm又は90nmであるレジストパターンの寸法を、微細化処理後、走査型電子顕微鏡(商品名「S−9380」、日立ハイテクノロジーズ社製)で測定し、下記式(11)により線幅微細化度を算出した。なお、微細化処理前の線幅が75nmであるレジストパターンについて算出した場合を「線幅微細化度(75LS)」とし、微細化処理前の線幅が90nmであるレジストパターンについて算出した場合を「線幅微細化度(90LS)」とした。
線幅微細化度(%)=(処理前の線幅(nm)−処理後の線幅(nm))/(処理前の線幅(nm))×100 ・・・(11)
微細化処理の前後でレジストパターンが形成されていない部分の基板の膜厚をラムダエース(KLAテンコール社製)にて測定し、微細化処理の前後での膜厚の差を膜減り量として算出した。
下記式(M−1)〜(M−3)で表される、化合物(M−1)53.93g(50mol%)、化合物(M−2)35.38g(40mol%)、及び化合物(M−3)10.69g(10mol%)を200gの2−ブタノンに溶解し、更にジメチル2,2’−アゾビス(2−メチルプロピオネート)5.58gを投入した単量体溶液(1)を調製した。一方、温度計及び滴下漏斗を備えた500mLの三口フラスコに100gの2−ブタノンを投入し、30分間窒素パージした。窒素パージ後、フラスコ内をマグネティックスターラーで攪拌しながら80℃になるように加熱した。滴下漏斗を用い、予め調製しておいた単量体溶液(1)を3時間かけて滴下した。滴下開始時刻を重合反応開始時刻とし、重合反応を6時間実施した。重合反応終了後、重合溶液を水冷により30℃以下に冷却した。冷却後、2,000gのメタノールに投入し、析出した白色粉末を濾別した。濾別した白色粉末を400gのメタノールにてスラリー状で2度洗浄した後、再度濾別し、50℃にて17時間乾燥して、白色粉末の共重合体(1)を得た。収量は74gであり、収率は74%であった。
下記式(M−1)、(M−2)、及び(M−4)で表される、化合物(M−1)47.54g(46mol%)、化合物(M−2)12.53g(15mol%)、及び化合物(M−4)39.93g(39mol%)を200gの2−ブタノンに溶解し、更に2,2’−アゾビス(イソブチロニトリル)4.08gを投入して単量体溶液(2)を調製した。一方、温度計及び滴下漏斗を備えた1,000mLの三口フラスコに100gの2−ブタノンを投入し、30分間窒素パージした。窒素パージ後、フラスコ内をマグネティックスターラーで攪拌しながら80℃になるように加熱した。滴下漏斗を用い、予め調製しておいた単量体溶液(2)を3時間かけて滴下した。滴下開始時刻を重合反応開始時刻とし、重合反応を6時間実施した。重合反応終了後、重合溶液を水冷により30℃以下に冷却した。冷却後、2,000gのメタノールに投入し、析出した白色粉末を濾別した。濾別した白色粉末を400gのメタノールにてスラリー状で2度洗浄した後、再度濾別し、50℃にて17時間乾燥して、白色粉末の共重合体(2)を得た。収量は73gであり、収率は73%であった。
樹脂(A)として合成例1で合成した樹脂(a−1)30部及び合成例2で合成した樹脂(a−2)70部、酸発生剤(B)としてトリフェニルスルホニウム・ノナフルオロ−n−ブタンスルホネート4部及び1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム・ノナフルオロ−n−ブタンスルホネート5部、並びに酸拡散制御剤(C)としてR−(+)−(tert−ブトキシカルボニル)−2−ピペリジンメタノール0.83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1710部及びシクロヘキサノン730部からなる溶剤(E)に溶解し、孔径0.2μmのメンブランフィルターでろ過することにより、フォトレジスト膜形成用の感放射線性樹脂組成物溶液(a)を調製した。
(実施例1)
ビニルスルホン酸0.03部を4−メチル−2−ペンタノール99.97部に溶解した後、孔径0.2μmのメンブランフィルターでろ過することにより、レジストパターン微細化組成物(1)を調製した。
メタクリル酸3.70部を4−メチル−2−ペンタノール96.3部に溶解した後、孔径0.2μmのメンブランフィルターでろ過することにより、レジストパターン微細化組成物(2)を調製した。
ビス(ノナフルオロブタンスルホニル)イミド0.03部を4−メチル−2−ペンタノール99.97部に溶解した後、孔径0.2μmのメンブランフィルターでろ過することにより、レジストパターン微細化組成物(3)を調製した。
ビス(ノナフルオロブタンスルホニル)イミド0.03部を水99.97部に溶解した後、孔径0.2μmのメンブランフィルターでろ過することにより、レジストパターン微細化組成物(4)を調製した。
8インチシリコンウェハ上に、下層反射防止膜(商品名「ARC29A」、ブルワーサイエンス社製)を商品名「CLEAN TRACK ACT8」(東京エレクトロン社製)を用いてスピンコートすることにより、膜厚77nmとなるように塗布し、PB(205℃、60秒)を行い塗膜を形成した。形成した塗膜上に、合成例3で調製した感放射線性樹脂組成物溶液(a)を、商品名「CLEAN TRACK ACT8」(東京エレクトロン社製)を用いてスピンコートし、PB(125℃、60秒)を行い膜厚120nmのレジスト膜を形成した。形成したレジスト膜を、ArFエキシマレーザー露光装置(商品名「NSR S306C」、ニコン社製、照明条件;NA0.78、σ0/σ1=0.93/0.62、Dipole)を用い、マスクパターンを介して露光量34mJ/cm2にて露光し、PB(115℃、60秒)を行った後、2.38%のテトラメチルアンモニウムヒドロキシド水溶液によって、23℃、30秒の条件で現像した。水洗した後、乾燥することによりポジ型のレジストパターンを形成した。なお、露光には、本実施例の条件における最適露光量(34mJ/cm2)を用いた。ここで、最適露光量とは、上記条件下で、マスクパターンの設計通りの寸法のレジストパターンが得られる露光量のことをいう。
レジストパターン微細化組成物(1)の代わりに、下記表1に記載したレジストパターン微細化組成物を用いたこと以外は、実施例5と同様にして各評価用基板を得た。得られた各評価用基板の評価結果をあわせて下記表1に示す。
Claims (4)
- 感放射線性樹脂組成物を用いて形成したレジストパターン上に、レジストパターン微細化組成物を塗布し、ベーク後、洗浄して前記レジストパターンを微細化する工程、を含むレジストパターン形成方法で用いられる、
酸性低分子化合物と、
前記レジストパターンを溶解しない溶媒と、
を含有するレジストパターン微細化組成物。 - 前記酸性低分子化合物が、カルボキシル基、スルホ基、及びスルホンイミド基からなる群より選択される少なくとも一種の官能基を有する請求項1に記載のレジストパターン微細化組成物。
- 前記溶媒が、水、炭素数1〜12の1価のアルコール、炭素数1〜10のアルキル基を有するエーテル、炭素数6〜12の直鎖状、分岐状又は環状の飽和炭化水素、芳香族炭化水素、及びテルペン化合物からなる群より選択される少なくとも一種を含む請求項1又は2に記載のレジストパターン微細化組成物。
- 感放射線性樹脂組成物を用いて形成したレジストパターン上に、請求項1〜3のいずれか一項に記載のレジストパターン微細化組成物を塗布し、ベーク後、洗浄して前記レジストパターンを微細化する工程、を含むレジストパターン形成方法。
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