JPWO2017094860A1 - パターン形成方法、電子デバイスの製造方法、積層膜及び上層膜形成用組成物 - Google Patents
パターン形成方法、電子デバイスの製造方法、積層膜及び上層膜形成用組成物 Download PDFInfo
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- JPWO2017094860A1 JPWO2017094860A1 JP2017554188A JP2017554188A JPWO2017094860A1 JP WO2017094860 A1 JPWO2017094860 A1 JP WO2017094860A1 JP 2017554188 A JP2017554188 A JP 2017554188A JP 2017554188 A JP2017554188 A JP 2017554188A JP WO2017094860 A1 JPWO2017094860 A1 JP WO2017094860A1
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- 239000010936 titanium Substances 0.000 description 1
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- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PCFIPYFVXDCWBW-UHFFFAOYSA-N tricyclo[3.3.1.03,7]nonane Chemical compound C1C(C2)C3CC2CC1C3 PCFIPYFVXDCWBW-UHFFFAOYSA-N 0.000 description 1
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- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
- UTCOSYZEYALTGJ-UHFFFAOYSA-N tris(2-tert-butylphenyl)sulfanium Chemical compound CC(C)(C)C1=CC=CC=C1[S+](C=1C(=CC=CC=1)C(C)(C)C)C1=CC=CC=C1C(C)(C)C UTCOSYZEYALTGJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
[1]
感活性光線性又は感放射線性樹脂組成物を用いて、基板上に感活性光線性又は感放射線性膜を形成する工程、
上層膜形成用組成物を用いて、上記感活性光線性又は感放射線性膜上に上層膜を形成する工程、
上記感活性光線性又は感放射線性膜と上記上層膜を含む積層膜を露光する工程、及び
露光された上記積層膜に対して、有機溶剤を含む現像液を用いて現像を行なう工程、
を含むパターン形成方法であって、
上記上層膜形成用組成物は、樹脂(XA)、フッ素原子を含有する樹脂(XB)、塩基性化合物(XC)及び溶剤(XD)を含有し、樹脂(XA)は、フッ素原子を含有しない樹脂であるか、フッ素原子を含有する場合には、質量基準によるフッ素原子の含有率が樹脂(XB)中のフッ素原子の含有率よりも低い樹脂であるパターン形成方法。
樹脂(XB)の含有率が、上記上層膜形成用組成物の全固形分を基準として20質量%以下である、[1]に記載のパターン形成方法。
上記上層膜形成用組成物が、溶剤(XD)として少なくとも1種の2級アルコール溶剤を含有する、[1]又は[2]に記載のパターン形成方法。
上記上層膜形成用組成物が、溶剤(XD)として少なくとも1種の2級アルコール溶剤と少なくとも1種のエーテル系溶剤を含有する、[1]〜[3]のいずれかに記載のパターン形成方法。
樹脂(XA)中のフッ素原子の含有率が0質量%〜5質量%である、[1]〜[4]のいずれかに記載のパターン形成方法。
樹脂(XB)中のフッ素原子の含有率が15質量%以上である、[1]〜[5]のいずれかに記載のパターン形成方法。
樹脂(XA)中のフッ素原子の含有率と、樹脂(XB)中のフッ素原子の含有率との差が10質量%以上である、[1]〜[6]のいずれかに記載のパターン形成方法。
樹脂(XA)がフッ素原子を含有しない樹脂である、[1]〜[7]のいずれかに記載のパターン形成方法。
上記上層膜形成用組成物が、塩基性化合物(XC)として、少なくともアミン化合物又はアミド化合物のいずれかを含有する、[1]〜[8]のいずれかに記載のパターン形成方法。
上記露光が液浸露光である、[1]〜[9]のいずれかに記載のパターン形成方法。
[1]〜[10]のいずれかにパターン形成方法を含む電子デバイスの製造方法。
感活性光線性又は感放射線性膜と、上記感活性光線性又は感放射線性膜上に上層膜とを含む積層膜であって、上記上層膜が、樹脂(XA)、フッ素原子を含有する樹脂(XB)、塩基性化合物(XC)及び溶剤(XD)を含有する上層膜形成用組成物であって、樹脂(XA)は、フッ素原子を含有しない樹脂であるか、フッ素原子を含有する場合には、質量基準によるフッ素原子の含有率が樹脂(XB)中のフッ素原子の含有率よりも低い樹脂である上層膜形成用組成物を用いて形成された膜である積層膜。
感活性光線性又は感放射線性膜の上に形成される上層膜形成用組成物であって、樹脂(XA)、フッ素原子を含有する樹脂(XB)、塩基性化合物(XC)及び溶剤(XD)を含有し、樹脂(XA)は、フッ素原子を含有しない樹脂であるか、フッ素原子を含有する場合には、質量基準によるフッ素原子の含有率が樹脂(XB)中のフッ素原子の含有率よりも低い樹脂である上層膜形成用組成物。
尚、本明細書における基(原子団)の表記において、置換及び無置換を記していない表記は、置換基を有さないものと共に置換基を有するものをも包含するものである。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含するものである。
[パターン形成方法]
本発明のパターン形成方法は、感活性光線性又は感放射線性樹脂組成物を用いて、基板上に感活性光線性又は感放射線性膜を形成する工程aと、上層膜形成用組成物を用いて、上記感活性光線性又は感放射線性膜上に上層膜を形成する工程bと、上記感活性光線性膜と上層膜を含む積層膜に対して露光を行う工程cと、露光された上記積層膜に対して、有機溶剤を含む現像液を用いて現像する工程dとを含む。
<工程a>
工程aでは、本発明の感活性光線性又は感放射線性樹脂組成物を用いて、基板上に感活性光線性又は感放射線性膜を形成する。基板上に感活性光線性又は感放射線性膜を形成する方法としては、例えば、感活性光線性又は感放射線性樹脂組成物を基板上に塗布する方法が挙げられる。塗布方法としては、特に限定されず、従来公知のスピンコート法、スプレー法、ローラーコート法、浸漬法などを用いることができ、好ましくはスピンコート法である。
<工程b>
工程bでは、工程aで形成した感活性光線性又は感放射線性膜上に、上層膜形成用組成物(トップコート組成物)を用いて上層膜を形成する。上層膜を形成する方法としては、例えば、上層膜形成用組成物を感活性光線性又は感放射線性膜上に塗布する方法が挙げられる。塗布方法としては、特に限定されず、上述した感活性光線性又は感放射線性樹脂組成物の塗布方法と同様の方法が挙げられる。
上層膜の屈折率は、解像性の観点から、感活性光線性又は感放射線性膜の屈折率に近いことが好ましい。
上層膜は液浸液に不溶であることが好ましく、水に不溶であることがより好ましい。
<工程c>
工程cでは、感活性光線性又は感放射線性膜と、その上に形成された上層膜とを含む積層膜に対して露光を行う。工程cにおける露光は、一般的に知られている方法により行うことができ、例えば、上層膜が形成された感活性光線性又は感放射線性膜に対して、所定のマスクを通して、活性光線又は放射線を照射する。このとき、好ましくは、活性光線又は放射線を、液浸液を介して照射するが、これに限定されるものではない。露光量は適宜設定できるが、通常1〜100mJ/cm2である。
<工程d>
工程dにおいて、有機溶剤を含む現像液を用いて現像することにより、ネガ型のパターンを形成する。工程dは、感活性光線性又は感放射線性膜の可溶部分を同時に除去する工程であることが好ましい。
アルカリ現像液のアルカリ濃度は、通常0.01〜20質量%である。
アルカリ現像液を用いて現像を行う時間は、通常10〜300秒である。
アルカリ現像液のアルカリ濃度(及びpH)及び現像時間は、形成するパターンに応じて、適宜調整することができる。
[上層膜形成用組成物]
次に、本発明のパターン形成方法において用いられる上層膜形成用組成物について説明する。
本発明の上層膜形成用組成物は、少なくとも2種の樹脂(XA)及び樹脂(XB)を含有する。ここで、樹脂(XB)はフッ素原子を含有する樹脂であり、樹脂(XA)は、フッ素原子を含有しない樹脂であるか、フッ素原子を含有する場合には、質量基準によるフッ素原子の含有率が、樹脂(XB)中のフッ素原子の含有率よりも低い樹脂である。上述の通り、フッ素原子の含有率が互いに異なる2種の樹脂(XA)及び樹脂(XB)を併用することにより、上層膜の表面がフッ素原子含有率のより高い樹脂(XB)の疎水膜で覆われるため、塩基性化合物の揮発が抑制される。その結果、感活性光線性又は感放射線性膜の未露光部への塩基性化合物の移動が効率よく起こるため、EL及びDOFを飛躍的に向上させることが可能となる。
樹脂(XA)は、露光時に光が上層膜を通して感活性光線性又は感放射線性膜に到達するため、使用する露光光源に対して透明であることが好ましい。ArF液浸露光に使用する場合は、ArF光への透明性の点から上記樹脂は実質的に芳香族基を有さないことが好ましい。
ここで、樹脂(XA)中の側鎖部分が有するCH3部分構造(以下、単に「側鎖CH3部分構造」ともいう)は、エチル基、プロピル基等が有するCH3部分構造を包含するものである。
R57〜R64は、それぞれ独立に、水素原子、フッ素原子又はアルキル基を表す。但し、R57〜R61及びR62〜R64の内、少なくとも1つは、フッ素原子又は少なくとも1つの水素原子がフッ素原子で置換されたアルキル基(好ましくは炭素数1〜4)を表す。R57〜R61は、全てがフッ素原子であることが好ましい。R62及びR63は、少なくとも1つの水素原子がフッ素原子で置換されたアルキル基(好ましくは炭素数1〜4)が好ましく、炭素数1〜4のパーフルオロアルキル基であることがさらに好ましい。R62とR63は、互いに連結して環を形成してもよい。
R10及びR11は、水素原子、フッ素原子、炭素数1〜4個の、直鎖もしくは分岐のアルキル基、または炭素数1〜4個の、直鎖もしくは分岐のフッ素化アルキル基を表す。
樹脂(XA)の含有率は、上層膜形成用組成物中の全固形分を基準として、0.5〜10.0質量%が好ましく、より好ましくは1.0〜6.0質量%、更に好ましくは1.5〜5.0質量%である。
樹脂(XB)は、上述した樹脂(XA)と同様、ArF液浸露光に使用する場合は、ArF光への透明性の点から上記樹脂は芳香族基を有さないことが好ましい。
R57〜R64は、それぞれ独立に、水素原子、フッ素原子又はアルキル基を表す。但し、R57〜R61及びR62〜R64の内、少なくとも1つは、フッ素原子又は少なくとも1つの水素原子がフッ素原子で置換されたアルキル基(好ましくは炭素数1〜4)を表す。R57〜R61は、全てがフッ素原子であることが好ましい。R62及びR63は、少なくとも1つの水素原子がフッ素原子で置換されたアルキル基(好ましくは炭素数1〜4)が好ましく、炭素数1〜4のパーフルオロアルキル基であることがさらに好ましい。R62とR63は、互いに連結して環を形成してもよい。
R10及びR11は、水素原子、フッ素原子、炭素数1〜4個の、直鎖もしくは分岐のアルキル基、または炭素数1〜4個の、直鎖もしくは分岐のフッ素化アルキル基を表す。
塩基性化合物(XC)として、フェノキシ基を有するアミン化合物も適宜用いることができる。
塩基性化合物(XC)として、アンモニウム塩も適宜用いることができる。アンモニウム塩のアニオンとしては、例えば、ハライド、スルホネート、ボレート及びフォスフェートが挙げられる。これらのうち、ハライド及びスルホネートが特に好ましい。
本発明の組成物は、塩基性化合物(XC)として、窒素原子を有し、酸の作用により脱離する基を有する低分子化合物(以下において、「低分子化合物(D)」又は「化合物(D)」ともいう)を含有することができる。低分子化合物(D)は、酸の作用により脱離する基が脱離した後は、塩基性を有することが好ましい。
R’は、それぞれ独立に、水素原子、直鎖状又は分岐状アルキル基、シクロアルキル基、アリール基、アラルキル基、又はアルコキシアルキル基を表す。R’は相互に結合して環を形成していても良い。
例えば、メタン、エタン、プロパン、ブタン、ペンタン、ヘキサン、ヘプタン、オクタン、ノナン、デカン、ウンデカン、ドデカン等の直鎖状、分岐状のアルカンに由来する基、これらのアルカンに由来する基を、例えば、シクロブチル基、シクロペンチル基、シクロヘキシル基等のシクロアルキル基の1種以上或いは1個以上で置換した基、
シクロブタン、シクロペンタン、シクロヘキサン、シクロヘプタン、シクロオクタン、ノルボルナン、アダマンタン、ノラダマンタン等のシクロアルカンに由来する基、これらのシクロアルカンに由来する基を、例えば、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、2−メチルプロピル基、1−メチルプロピル基、t−ブチル基等の直鎖状、分岐状のアルキル基の1種以上或いは1個以上で置換した基、
ベンゼン、ナフタレン、アントラセン等の芳香族化合物に由来する基、これらの芳香族化合物に由来する基を、例えば、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、2−メチルプロピル基、1−メチルプロピル基、t−ブチル基等の直鎖状、分岐状のアルキル基の1種以上或いは1個以上で置換した基、
ピロリジン、ピペリジン、モルホリン、テトラヒドロフラン、テトラヒドロピラン、インドール、インドリン、キノリン、パーヒドロキノリン、インダゾール、ベンズイミダゾール等の複素環化合物に由来する基、これらの複素環化合物に由来する基を直鎖状、分岐状のアルキル基或いは芳香族化合物に由来する基の1種以上或いは1個以上で置換した基、直鎖状、分岐状のアルカンに由来する基・シクロアルカンに由来する基をフェニル基、ナフチル基、アントラセニル基等の芳香族化合物に由来する基の1種以上或いは1個以上で置換した基等或いは上記の置換基がヒドロキシル基、シアノ基、アミノ基、ピロリジノ基、ピペリジノ基、モルホリノ基、オキソ基等の官能基で置換された基等が挙げられる。
(塩基発生剤)
上述したように、塩基性化合物(XC)には、ClogP値が1.30以下である塩基発生剤も含まれる。
感活性光線性又は感放射線性膜を溶解せずに良好なパターンを形成するために、本発明における上層膜形成用組成物は、感活性光線性又は感放射線性膜を溶解しない溶剤を含有することが好ましく、有機系現像液とは異なる成分の溶剤を用いることがより好ましい。
1000cP=1Pa・s
上記以外の溶剤を混合する場合、その混合比は、感活性光線性又は感放射線性組成物の全溶剤量に対して、通常0〜30質量%、好ましくは0〜20質量%、更に好ましくは0〜10質量%である。上記以外の溶剤を混合することで、感活性光線性又は感放射線性膜に対する溶解性、上層膜形成用組成物中の樹脂の溶解性、感活性光線性又は感放射線性膜からの溶出特性、などを適宜調整することができる。
本発明の上層膜形成用組成物は、更に界面活性剤を含有していてもよい。
界面活性剤としては特に制限はなく、上層膜形成用組成物を均一に成膜することができ、かつ、上層膜形成用組成物の溶剤に溶解することができれば、アニオン性界面活性剤、カチオン性界面活性剤、ノニオン性界面活性剤のいずれも用いることができる。
<上層膜形成用組成物の調製方法>
本発明の上層膜形成用組成物は、上述した各成分を溶剤に溶解し、フィルター濾過することが好ましい。フィルターとしては、ポアサイズ0.1μm以下、より好ましくは0.05μm以下、更に好ましくは0.03μm以下のポリテトラフロロエチレン製、ポリエチレン製、ナイロン製のものが好ましい。なお、フィルターは、複数種類を直列又は並列に接続して用いてもよい。また、組成物を複数回濾過してもよく、複数回濾過する工程が循環濾過工程であってもよい。さらに、フィルター濾過の前後で、組成物に対して脱気処理などを行ってもよい。本発明の上層膜形成用組成物は、金属等の不純物を含まないことが好ましい。これら材料に含まれる金属成分の含有量としては、10ppm以下が好ましく、5ppm以下がより好ましく、1ppm以下が更に好ましく、実質的に含まないこと(測定装置の検出限界以下であること)が特に好ましい。
[感活性光線性又は感放射線性樹脂組成物]
次に、本発明のパターン形成方法に好適に用い得る感活性光線性又は感放射線性樹脂組成物について説明する。
本発明の感活性光線性又は感放射線性樹脂組成物は、典型的には、酸の作用により極性が増大して有機溶剤を含む現像液に対する溶解度が減少する樹脂を含有する。
シマレーザー光を照射する場合に好適に使用できる。
る繰り返し単位を含有する樹脂であることが好ましい。
R11は、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基又はsec−ブチル基を表し、Zは、炭素原子とともにシクロアルキル基を形成するのに必要な原子団を表す。
本発明の感活性光線性又は感放射線性樹脂組成物は、典型的には、活性光線又は放射線の照射により酸を発生する化合物(「光酸発生剤」ともいう)を含有する。
(カチオン)
一般式(3)中、X+は、カチオンを表す。
X+は、カチオンであれば特に制限されないが、好適な態様としては、例えば、後述する一般式(ZI)、(ZII)又は(ZIII)中のカチオン(Z-以外の部分)が挙げられる。
(好適な態様)
特定酸発生剤の好適な態様としては、例えば、下記一般式(ZI)、(ZII)又は(ZIII)で表される化合物が挙げられる。
R1c〜R5cは、各々独立に、水素原子、アルキル基、シクロアルキル基、アリール基、アルコキシ基、アリールオキシ基、アルコキシカルボニル基、アルキルカルボニルオキシ基、シクロアルキルカルボニルオキシ基、ハロゲン原子、水酸基、ニトロ基、アルキルチオ基又はアリールチオ基を表す。
R13は水素原子、フッ素原子、水酸基、アルキル基、シクロアルキル基、アルコキシ基、アルコキシカルボニル基、又はシクロアルキル基を有する基を表す。これらの基は置換基を有してもよい。
上記各成分を溶解させて感活性光線性又は感放射線性樹脂組成物を調製する際に使用することができる溶剤としては、例えば、アルキレングリコールモノアルキルエーテルカルボキシレート、アルキレングリコールモノアルキルエーテル、乳酸アルキルエステル、アルコキシプロピオン酸アルキル、炭素数4〜10の環状ラクトン、炭素数4〜10の、環を含有していてもよいモノケトン化合物、アルキレンカーボネート、アルコキシ酢酸アルキル、ピルビン酸アルキル等の有機溶剤を挙げることができる。
本発明の感活性光線性又は感放射線性樹脂組成物は、露光から加熱までの経時による性能変化を低減するために、塩基性化合物を含有することが好ましい。
R200 、R201及びR202 は、同一でも異なってもよく、水素原子、アルキル基(好ましくは炭素数1〜20)、シクロアルキル基(好ましくは炭素数3〜20)又はアリール基(炭素数6〜20)を表し、ここで、R201とR202は、互いに結合して環を形成してもよい。
塩基性化合物の使用量は、本発明の感活性光線性又は感放射線性樹脂組成物の固形分を基準として、通常、0.001〜10質量%、好ましくは0.01〜5質量%である。
本発明の感活性光線性又は感放射線性樹脂組成物は、疎水性樹脂(E)を含有してもよい。疎水性樹脂としては、例えば、上層膜形成用組成物が含有する上述した樹脂(XB)を好適に使用できる。また、例えば、特開2014−149409号公報の段落[0389]〜[0474]に記載された「[4]疎水性樹脂(D)」等も好適に挙げられる。
本発明の感活性光線性又は感放射線性樹脂組成物は、更に(F)界面活性剤を含有することが好ましく、フッ素系及び/又はシリコン系界面活性剤(フッ素系界面活性剤、シリコン系界面活性剤、フッ素原子と珪素原子の両方を有する界面活性剤)のいずれか、あるいは2種以上を含有することがより好ましい。
本発明の感活性光線性又は感放射線性樹脂組成物は、(G)カルボン酸オニウム塩を含有してもよい。カルボン酸オニウム塩としては、カルボン酸スルホニウム塩、カルボン酸ヨードニウム塩、カルボン酸アンモニウム塩などを挙げることができる。特に、(G)カルボン酸オニウム塩としては、ヨードニウム塩、スルホニウム塩が好ましい。更に、(G)カルボン酸オニウム塩のカルボキシレート残基が芳香族基、炭素−炭素2重結合を含有しないことが好ましい。特に好ましいアニオン部としては、炭素数1〜30の、直鎖、分岐または環状(単環または多環)のアルキルカルボン酸アニオンが好ましい。さらに好ましくはこれらのアルキル基の一部または全てがフッ素置換されたカルボン酸のアニオンが好ましい。アルキル鎖中に酸素原子を含んでいてもよい。これにより220nm以下の光に対する透明性が確保され、感度、解像力が向上し、疎密依存性、露光マージンが改良される。
本発明の感活性光線性又は感放射線性樹脂組成物には、必要に応じてさらに染料、可塑剤、光増感剤、光吸収剤、アルカリ可溶性樹脂、溶解阻止剤及び現像液に対する溶解性を促進させる化合物(例えば、分子量1000以下のフェノール化合物、カルボキシル基を有する脂環族、又は脂肪族化合物)等を含有させることができる。
[電子デバイスの製造方法]
本発明は、上述した本発明のパターン形成方法を含む、電子デバイスの製造方法にも関する。
<<レジスト組成物>>
<合成例1:樹脂(1)の合成)>
シクロヘキサノン102.3質量部を窒素気流下、80℃に加熱した。この液を攪拌しながら、下記構造式LM−2で表されるモノマー22.2質量部、下記構造式PM−1で表されるモノマー22.8質量部、下記構造式PM−9で表されるモノマー6.6質量部、シクロヘキサノン189.9質量部、及び、2,2’−アゾビスイソ酪酸ジメチル〔V−601、和光純薬工業(株)製〕2.40質量部の混合溶液を5時間かけて滴下した。滴下終了後、80℃で更に2時間攪拌した。反応液を放冷後、多量のヘキサン/酢酸エチル(質量比9:1)で再沈殿、ろ過し、得られた固体を真空乾燥することで、樹脂(1)を41.1質量部得た。
<樹脂(2)〜(13)の合成)>
合成例1と同様の操作を行い、酸分解性樹脂として後掲の樹脂(2)〜(13)を合成した。
下記表2に示す成分を同表に示す溶剤に溶解させ、固形分濃度3.5質量%の溶液を調製し、これを0.03μmのポアサイズを有するポリエチレンフィルターでろ過して、レジスト組成物Re−1〜Re−16を調製した。
疎水性樹脂として、以下の樹脂を用いた。各繰り返し単位の組成比、重量平均分子量(Mw)、分散度(Mw/Mn)と共に示す。これらは上述したレジスト組成物における樹脂(1)と同様の方法により求めた。
W−2:トロイゾルS−366(トロイケミカル(株)製;シリコン系)
W−3:ポリシロキサンポリマーKP−341(信越化学工業(株)製、シリコン系)
<溶剤>
溶剤として下記を用いた。
SL−2:シクロヘキサノン
SL−3:プロピレングリコールモノメチルエーテル(PGME)
SL−4:γ−ブチロラクトン
SL−5:プロピレンカーボネート
SL−6:2−エチルブタノール
SL−7:パーフルオロブチルテトラヒドロフラン
<<上層膜形成用組成物>>
<合成例2:樹脂X−1の合成>
窒素気流下シクロヘキサノン26.1gを3つ口フラスコに入れ、これを85℃に加熱した。これに下記構造式XM−2で表されるモノマー10.67g、下記構造式XM−3で表されるモノマー10.71g、下記構造式XM−8で表されるモノマー3.03g、及び、重合開始剤V−601(和光純薬製、0.553g)をシクロヘキサノン47.6gに溶解させた溶液を6時間かけて滴下した。滴下終了後、更に85℃で2時間反応させた。反応液を放冷後メタノール1140gに20分かけて滴下し、析出した粉体をろ取、乾燥すると、下記に示す樹脂X−1(20.9g)が得られた。得られた樹脂X−1の重量平均分子量は標準ポリスチレン換算で8000、分散度(Mw/Mn)は1.69であった。13C−NMRにより測定した組成比はモル比で40/30/30であった。
[各モノマー中のフッ素原子の分子量/モノマーの分子量]×100 式(1)
・樹脂中のフッ素原子の含有率RF(質量%)
=Σ(各モノマーの分子量×各モノマー中のフッ素原子の含有率MF×各モノマーの組成比)/Σ(各モノマーの分子量×各モノマーの組成比) 式(2)
下記表4に示す成分を同表に示す溶剤に溶解させ、固形分濃度3.0質量%の溶液を調製し、これを0.04μmのポアサイズを有するポリエチレンフィルターで濾過して、上層膜形成用組成物(T−1)〜(T−31)及び(TC−1)〜(TC−5)を調製した。下記の表4中、化合物及び界面活性剤の含有率(質量%)は、上層膜形成用組成物の全固形分を基準とするものである。
W−2:トロイゾルS−366(トロイケミカル(株)製;シリコン系)
W−3:ポリシロキサンポリマーKP−341(信越化学工業(株)製、シリコン系)
[後退接触角]
上記で調製した上層膜形成用組成物により上層膜を形成した場合における、上層膜の水に対する後退接触角を、下記方法により測定した。
[画像性能試験]
上記で調製したレジスト組成物及び上層膜形成用組成物を用いて、レジストパターンを形成し、下記の方法で評価を行った。
<ホールパターンの形成>
シリコンウエハ上に有機反射防止膜ARC29SR(Brewer社製)を塗布し、205℃で60秒間ベークを行い膜厚86nmの反射防止膜を形成した。その上に、下記表5に示すレジスト組成物を塗布し、100℃で60秒間に亘ってベークを行い、同表に記載の膜厚を有するレジスト膜を形成した。
<フォーカス余裕度(DOF:Depth of Focus)>
上記(ホールパターンの形成)の露光及び現像条件において孔径50nmのホールパターンを形成する露光量において、フォーカス方向に20nm刻みで、露光フォーカスの条件を変更して露光及び現像を行い、得られる各パターンのホール径(CD)を線幅測長走査型電子顕微鏡SEM((株)日立製作所S−9380)を使用して測定し、上記の各CDをプロットして得られる曲線の極小値又は極大値に対応するフォーカスをベストフォーカスとした。このベストフォーカスを中心にフォーカスを変化させた際に、ホール径が50nm±10%を許容するフォーカスの変動幅、すなわち、フォーカス余裕度(DOF、単位:nm)を算出した。値が大きいほど良好な性能であることを示す。結果を下記表6に示す。
<露光ラチチュード(EL:Exposure Latitude)>
測長走査型電子顕微鏡(SEM(株)日立製作所S−9380II)によりホールサイズを観察し、ホール部分が平均50nmのコンタクトホールパターンを解像する時の最適露光量を感度(Eopt)(mJ/cm2)とした。求めた最適露光量(Eopt)を基準とし、次いでホールサイズが目的の値である50nmの±10%(即ち、45nm及び55nm)となるときの露光量を求めた。そして、次式で定義される露光ラチチュード(EL、単位:%)を算出した。ELの値が大きいほど、露光量変化による性能変化が小さく、良好である。結果を下記表6に示す。
Claims (13)
- 感活性光線性又は感放射線性樹脂組成物を用いて、基板上に感活性光線性又は感放射線性膜を形成する工程、
上層膜形成用組成物を用いて、前記感活性光線性又は感放射線性膜上に上層膜を形成する工程、
前記感活性光線性又は感放射線性膜と前記上層膜を含む積層膜を露光する工程、及び
露光された前記積層膜に対して、有機溶剤を含む現像液を用いて現像を行なう工程、
を含むパターン形成方法であって、
前記上層膜形成用組成物は、樹脂(XA)、フッ素原子を含有する樹脂(XB)、塩基性化合物(XC)及び溶剤(XD)を含有し、樹脂(XA)は、フッ素原子を含有しない樹脂であるか、フッ素原子を含有する場合には、質量基準によるフッ素原子の含有率が樹脂(XB)中のフッ素原子の含有率よりも低い樹脂であるパターン形成方法。 - 樹脂(XB)の含有率が、前記上層膜形成用組成物の全固形分を基準として20質量%以下である、請求項1に記載のパターン形成方法。
- 前記上層膜形成用組成物が、溶剤(XD)として少なくとも1種の2級アルコール溶剤を含有する、請求項1又は2に記載のパターン形成方法。
- 前記上層膜形成用組成物が、溶剤(XD)として少なくとも1種の2級アルコール溶剤と少なくとも1種のエーテル系溶剤を含有する、請求項1〜3のいずれか1項に記載のパターン形成方法。
- 樹脂(XA)中のフッ素原子の含有率が0質量%〜5質量%である、請求項1〜4のいずれか1項に記載のパターン形成方法。
- 樹脂(XB)中のフッ素原子の含有率が15質量%以上である、請求項1〜5のいずれか1項に記載のパターン形成方法。
- 樹脂(XA)中のフッ素原子の含有率と、樹脂(XB)中のフッ素原子の含有率との差が10質量%以上である、請求項1〜6のいずれか1項に記載のパターン形成方法。
- 樹脂(XA)がフッ素原子を含有しない樹脂である、請求項1〜7のいずれか1項に記載のパターン形成方法。
- 前記上層膜形成用組成物が、塩基性化合物(XC)として、少なくともアミン化合物又はアミド化合物のいずれかを含有する、請求項1〜8のいずれか1項に記載のパターン形成方法。
- 前記露光が液浸露光である、請求項1〜9のいずれか1項に記載のパターン形成方法。
- 請求項1〜10のいずれか1項にパターン形成方法を含む電子デバイスの製造方法。
- 感活性光線性又は感放射線性膜と、前記感活性光線性又は感放射線性膜上に上層膜とを含む積層膜であって、前記上層膜が、樹脂(XA)、フッ素原子を含有する樹脂(XB)、塩基性化合物(XC)及び溶剤(XD)を含有する上層膜形成用組成物であって、樹脂(XA)は、フッ素原子を含有しない樹脂であるか、フッ素原子を含有する場合には、質量基準によるフッ素原子の含有率が樹脂(XB)中のフッ素原子の含有率よりも低い樹脂である上層膜形成用組成物を用いて形成された膜である積層膜。
- 感活性光線性又は感放射線性膜の上に形成される上層膜形成用組成物であって、樹脂(XA)、フッ素原子を含有する樹脂(XB)、塩基性化合物(XC)及び溶剤(XD)を含有し、樹脂(XA)は、フッ素原子を含有しない樹脂であるか、フッ素原子を含有する場合には、質量基準によるフッ素原子の含有率が樹脂(XB)中のフッ素原子の含有率よりも低い樹脂である上層膜形成用組成物。
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