JPWO2016121686A1 - カーボネート骨格を有する加水分解性シランを含むリソグラフィー用レジスト下層膜形成組成物 - Google Patents
カーボネート骨格を有する加水分解性シランを含むリソグラフィー用レジスト下層膜形成組成物 Download PDFInfo
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- JPWO2016121686A1 JPWO2016121686A1 JP2016572017A JP2016572017A JPWO2016121686A1 JP WO2016121686 A1 JPWO2016121686 A1 JP WO2016121686A1 JP 2016572017 A JP2016572017 A JP 2016572017A JP 2016572017 A JP2016572017 A JP 2016572017A JP WO2016121686 A1 JPWO2016121686 A1 JP WO2016121686A1
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- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-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
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- NBNZEBUNZGWIRJ-UHFFFAOYSA-N triphenylsulfanium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NBNZEBUNZGWIRJ-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound 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
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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Classifications
-
- 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
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Abstract
Description
また、半導体基板とフォトレジストとの間の下層膜として、シリコンやチタン等の金属元素を含むハードマスクとして知られる膜を使用することが行なわれている。この場合、レジストとハードマスクでは、その構成成分に大きな違いが有るため、それらのドライエッチングによって除去される速度は、ドライエッチングに使用されるガス種に大きく依存する。そして、ガス種を適切に選択することにより、フォトレジストの膜厚の大きな減少を伴うことなく、ハードマスクをドライエッチングによって除去することが可能となる。このように、近年の半導体装置の製造においては、反射防止効果を初め、さまざまな効果を達成するために、半導体基板とフォトレジストの間にレジスト下層膜が配置されるようになってきている。そして、これまでもレジスト下層膜用の組成物の検討が行なわれてきているが、その要求される特性の多様性などから、レジスト下層膜用の新たな材料の開発が望まれている。
(式(1)、式(2)、式(3)中、X1乃至X9はそれぞれ独立に酸素原子又はイオウ原子を示す。n、mはそれぞれ独立に1乃至4の整数を示す。nが1の場合はR1がヘテロ原子を有していてもよい炭素原子数1乃至40の炭化水素基を示し、nが2乃至4の場合はR1がヘテロ原子を有していてもよい炭素原子数2乃至40の炭化水素基を示す。
T1、T2、T3、及びT4はそれぞれ独立に炭素原子数2乃至40のヘテロ原子を有していてもよい炭化水素基を含む連結基を示す。
R3、R5、R7、及びR9はそれぞれ独立にアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、アミノ基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものである。
R2、R4、R6、及びR8はそれぞれ独立にアルコキシ基、アシルオキシ基、又はハロゲン基を示す。aはそれぞれ0乃至2の整数を示す。)で表される加水分解性シランからなる群より選ばれる少なくとも一種の加水分解性シランを含むものであるリソグラフィー用レジスト下層膜形成組成物、
第2観点として、該加水分解性シランが、式(1)、式(2)、及び式(3)で表される加水分解性シランからなる群から選ばれた少なくとも一種の加水分解性シランと、その他の加水分解性シランとの組み合わせであり、その他の加水分解性シランが式(4):
(式(4)中、R10はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものであり、R11はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、bは0乃至3の整数を示す。)で表される加水分解性シラン、及び式(5):
(式(5)中、R12はアルキル基で且つSi−C結合によりケイ素原子と結合しているものであり、R13はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、Yはアルキレン基又はアリーレン基を示し、cは0又は1の整数を示し、dは0又は1の整数である。)で表される加水分解性シランからなる群より選ばれた少なくとも一種の加水分解性シランである第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、第1観点に記載の式(1)、式(2)、及び式(3)で表される加水分解性シランからなる群より選ばれた少なくとも一種の加水分解性シランと、第2観点に記載の式(4)で表される加水分解性シランとの組み合わせからなる加水分解性シランの加水分解縮合物をポリマーとして含む第1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、更に酸を含む第1観点乃至第3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5観点として、更に水を含む第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、更に塩を含む第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の硬化物からなる、半導体基板上に形成されたレジスト下層膜、
第8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、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト膜形成組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、前記レジストパターンにより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と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、及び
第9観点として、半導体基板上に有機下層膜を形成する工程、その上に第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を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト膜形成組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、前記レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機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。
本発明では基板上に有機下層膜を介するか、又は有機下層膜を介さず、その上に本発明の組成物からのレジスト下層膜(無機系シリコン系化合物含有)を被覆し、その上にレジスト膜(有機レジスト膜)を被覆するという順序でなされる。
通常、微細なパターンを形成する上で、パターン倒れを防ぐためにレジスト膜厚を薄くする傾向がある。レジストの薄膜化によりその下層に存在する膜にパターンを転写するためのドライエッチングは、上層のレジスト膜よりもエッチング速度が高いことを要する。本発明のレジスト下層膜形成組成物はエッチングガスの選択によりレジストに対して高いドライエッチング速度を有するリソグラフィー用レジスト下層膜を提供でき、さらにより下層の基板に矩形レジストパターンを転写することを可能とするものである。
また、本発明では当該レジスト下層膜がハードマスクとして機能するものである。一般に、どの世代のリソグラフィーのどの現像プロセスにおいてもレジスト形状を制御するには下層膜の酸性度調節が必要とされる。従って本発明の組成物のように特に、KrF、ArF、EUV、EB等の各波長の光及び電子線により酸を発生する骨格はフォトレジストのコントラストをより高めることが出来、有用であると考えられる。
本発明のリソグラフィー用レジスト下層膜形成組成物ではそれに含まれる加水分解性シランがカーボネート骨格、又は炭素原子がイオウ原子に置き換わったチオカーボネート骨格を含有することで特にArF露光、EUV露光において、パターン解像性能をさらに向上させることが出来る。
固形分中に占める加水分解性シラン、その加水分解物、及びその加水分解縮合物の割合は、20質量%以上であり、例えば50乃至100質量%、60乃至99質量%、70乃至99質量%である。
T1、T2、T3、及びT4はそれぞれ独立に炭素原子数2乃至40のヘテロ原子を有していてもよい炭化水素基を含む連結基を示す。上記ヘテロ原子は酸素原子が挙げられ、酸素原子は例えばエステル基、エーテル基、カルボニル基等の形で炭化水素基と組み合わせて連結基を形成することができる。
例えば下記に例示するメチル基、エチル基、プロピル基等のアルキル基に対応するメチレン基、エチレン基、プロピレン基等のアルキレン基も2価の炭化水素基の一例である。
R2、R4、R6、及びR8はそれぞれ独立にアルコキシ基、アシルオキシ基、又はハロゲン基を示す。aはそれぞれ0乃至2の整数を示す。
上記ハロゲン化アルキル基、上記ハロゲン化アリール基としてはハロゲン基で置換された上記に例示したアルキル基、アリール基であり、該ハロゲン基としてはフッ素、塩素、臭素、ヨウ素等が挙げられる。
上記アルコキシアリール基としては上記アルコキシ基により置換したアリール基であり、例えばメトキシフェニル基、エトキシフェニル基が挙げられる。
アミノ基を有する有機基としては、アミノ基、アミノメチル基、アミノエチル基等が挙げられる。
シアノ基を有する有機基としては、シアノエチル基、シアノプロピル基等が挙げられる。
式(4)、式(5)中の官能基は上述の例を挙げることができる。
また、アリーレン基としては上記アリール基に由来するアリーレン基を挙げることができる。例えばフェニル基であればフェニレン基、ナフチル基であればナフチレン基が挙げられる。
GPCの測定条件は、例えばGPC装置(商品名HLC−8220GPC、東ソー株式会社製)、GPCカラム(商品名ShodexKF803L、KF802、KF801、昭和電工製)、カラム温度は40℃、溶離液(溶出溶媒)はテトラヒドロフラン、流量(流速)は1.0ml/min、標準試料はポリスチレン(昭和電工株式会社製)を用いて行うことができる。
また、加水分解性基の1モル当たり0.001乃至10モル、好ましくは0.001乃至1モルの加水分解触媒を用いることができる。
加水分解し縮合させる際に触媒を用いることができる。
加水分解触媒としては、金属キレート化合物、有機酸、無機酸、有機塩基、無機塩基を挙げることができる。
(但し、m1は2乃至11、n1は2乃至3の整数を、R21はアルキル基又はアリール基を、YA −は陰イオンを示す。)で示される構造を有する第4級アンモニウム塩、式(D−2):
(但し、R22、R23、R24及びR25はアルキル基又はアリール基を、Nは窒素原子を、YA −は陰イオンを示し、且つR22、R23、R24、及びR25はそれぞれC−N結合により窒素原子と結合されているものである)で示される構造を有する第4級アンモニウム塩、
式(D−3):
(但し、R26及びR27はアルキル基又はアリール基を、YA −は陰イオンを示す)で示される構造を有する第4級アンモニウム塩、
式(D−4):
(但し、R28はアルキル基又はアリール基を、YA −は陰イオンを示す)で示される構造を有する第4級アンモニウム塩、
式(D−5):
(但し、R29及びR30はアルキル基又はアリール基を、YA −は陰イオンを示す)で示される構造を有する第4級アンモニウム塩、
式(D−6):
(但し、m1は2乃至11、n1は2乃至3の整数を、Hは水素原子を、YA −は陰イオンを示す)で示される構造を有する第3級アンモニウム塩が挙げられる。
(但し、R31、R32、R33、及びR34はアルキル基又はアリール基を、Pはリン原子を、YA −は陰イオンを示し、且つR31、R32、R33、及びR34はそれぞれC−P結合によりリン原子と結合されているものである)で示される第4級ホスホニウム塩が挙げられる。
(但し、R35、R36、及びR37はアルキル基又はアリール基を、Sは硫黄原子を、YA −は陰イオンを示し、且つR35、R36、及びR37はそれぞれC−S結合により硫黄原子と結合されているものである)で示される第3級スルホニウム塩が挙げられる。
また加えるアルコールとしては塗布後の加熱により飛散しやすいものが好ましく、例えばメタノール、エタノール、プロパノール、イソプロパノール、ブタノール等が挙げられる。加えるアルコールはレジスト下層膜形成組成物100質量部に対して1乃至20質量部とすることができる。
本発明のリソグラフィー用下層膜形成組成物は、上記の成分の他、必要に応じて有機ポリマー化合物、光酸発生剤及び界面活性剤等を含むことができる。
有機ポリマー化合物にヒドロキシル基が含有されている場合は、このヒドロキシル基はポリオルガノシロキサンと架橋反応を形成することができる。
有機ポリマー化合物は一種のみを使用することができ、または二種以上を組み合わせて使用することができる。
有機ポリマー化合物が使用される場合、その割合としては、縮合物(ポリオルガノシロキサン)100質量部に対して、1乃至200質量部、または5乃至100質量部、または10乃至50質量部、または20乃至30質量部である。
酸発生剤としては、熱酸発生剤や光酸発生剤が挙げられる。
光酸発生剤は、レジストの露光時に酸を生ずる。そのため、下層膜の酸性度の調整ができる。これは、下層膜の酸性度を上層のレジストとの酸性度に合わせるための一方法である。また、下層膜の酸性度の調整によって、上層に形成されるレジストのパターン形状の調整ができる。
本発明では上記リソグラフィー用レジスト下層膜形成組成物を用いて、基板上にレジスト下層膜を塗布法により形成するか、又は基板上の有機下層膜を介してその上にレジスト下層膜を塗布法により形成し、そのレジスト下層膜上にレジスト膜(例えば、フォトレジスト、電子線レジスト、EUVレジスト)を形成する。そして、露光と現像によりレジストパターンを形成し、そのレジストパターンを用いてレジスト下層膜をドライエッチングしてパターンの転写を行い、そのパターンにより基板を加工するか、又は有機下層膜をエッチングによりパターン転写しその有機下層膜により基板の加工を行う。
従って、例えばレジストパターンが形成され、その下層に存在している本発明のレジスト下層膜をハロゲン含有ガスでドライエッチングしてレジスト下層膜にパターンを転写し、そのレジスト下層膜に転写されたパターンでハロゲン含有ガスを用いて基板加工を行う。あるいは、パターン転写されたレジスト下層膜を用いて、その下層の有機下層膜を酸素系ガスでドライエッチングして有機下層膜にパターン転写を行って、そのパターン転写された有機下層膜で、ハロゲン含有ガスを用いて基板加工を行う。
半導体装置の製造に使用される基板(例えば、シリコンウエハ基板、シリコン/二酸化シリコン被覆基板、シリコンナイトライド基板、ガラス基板、ITO基板、ポリイミド基板、及び低誘電率材料(low−k材料)被覆基板等)の上に、スピナー、コーター等の適当な塗布方法により本発明のリソグラフィー用レジスト下層膜形成組成物が塗布され、その後、焼成することによりレジスト下層膜が形成される。焼成する条件としては、焼成温度80℃乃至250℃、焼成時間0.3乃至60分間の中から適宜、選択される。好ましくは、焼成温度150℃乃至250℃、焼成時間0.5乃至2分間である。ここで、形成される下層膜の膜厚としては、例えば、5乃至1000nmであり、または20乃至500nmであり、または50乃至300nmであり、または50乃至200nmである。
レジスト下層膜のドライエッチングはフッ素系ガスによることが好ましく、フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、トリフルオロメタン(CHF3)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、トリフルオロメタン(CHF3)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
最後に、半導体基板の加工が行なわれる。上記のとおり半導体基板の加工はフッ素系ガスによるドライエッチングによって行なわれることが好ましい。
本発明のリソグラフィー用レジスト下層膜形成組成物ではそれに含まれる加水分解性シランがカーボネート骨格、又は炭素原子がイオウ原子に置き換わったチオカーボネート骨格を含有することで特にArF露光、EUV露光において、パターン解像性能をさらに向上させることが出来る。
テトラエトキシシラン24.51g(シラン全体中で70mol%)、フェニルトリメトキシシラン3.33g(シラン全体中で10mol%)、トリエトキシメチルシラン3.00g(シラン全体中で10mol%)、4−(2−(トリエトキシシリル)エチル)−1,3−ジオキソラン−2−オン4.68g(シラン全体中で10mol%)、アセトン53.28gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.21gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル20/80の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように調整した。得られたポリマーは式(2−1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン23.67g(シラン全体中で70mol%)、フェニルトリメトキシシラン3.22g(シラン全体中で10mol%)、トリエトキシメチルシラン1.45g(シラン全体中で5mol%)、4−(2−(トリエトキシシリル)エチル)−1,3−ジオキソラン−2−オン4.52g(シラン全体中で10mol%)、フェニルスルホニルプロピルトリエトキシシラン2.81g(シラン全体中で5mol%)、アセトン53.51gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸10.82gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル20/80の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように調整した。得られたポリマーは式(2−2)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1600であった。
テトラエトキシシラン24.67g(シラン全体中で70mol%)、フェニルトリメトキシシラン1.68g(シラン全体中で5mol%)、トリエトキシメチルシラン1.51g(シラン全体中で5mol%)、4−(2−(トリエトキシシリル)エチル)−1,3−ジオキソラン−2−オン4.71g(シラン全体中で10mol%)、4−メトキシベンジルトリメトキシシラン2.05g(シラン全体中で5mol%)、フェニルスルホニルプロピルトリエトキシシラン2.93g(シラン全体中で5mol%)、アセトン53.23gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.28gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル20/80の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように調整した。得られたポリマーは式(2−3)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
テトラエトキシシラン24.01g(シラン全体中で70mol%)、フェニルトリメトキシシラン1.63g(シラン全体中で5mol%)、トリエトキシメチルシラン1.47g(シラン全体中で5mol%)、4−(2−(トリエトキシシリル)エチル)−1,3−ジオキソラン−2−オン2.29g(シラン全体中で5mol%)、4−メトキシベンジルトリメトキシシラン1.99g(シラン全体中で5mol%)、フェニルスルホニルプロピルトリエトキシシラン2.85g(シラン全体中で5mol%)、5−(トリエトキシシリル)ヘキサヒドロ‐4,7−メタノイソベンゾフラン‐1,3−ジオン2.70g(シラン全体中で5mol%)、アセトン52.43gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸10.98gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル20/80の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように調整した。得られたポリマーは式(2−4)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1700であった。
テトラエトキシシラン24.72g(シラン全体中で70mol%)、トリエトキシメチルシラン6.04g(シラン全体中で20mol%)、4−(2−(トリエトキシシリル)エチル)−1,3−ジオキソラン−2−オン4.72g(シラン全体中で10mol%)、アセトン53.22gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.30gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル20/80の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように調整した。得られたポリマーは式(2−5)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン24.63g(シラン全体中で70mol%)、トリエトキシメチルシラン6.02g(シラン全体中で20mol%)、トリメトキシシリルプロピルメチルトリチオカーボネート4.83g(シラン全体中で10mol%)、アセトン53.24gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.26gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル20/80の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように調整した。得られたポリマーは式(2−6)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン25.81g(シラン全体中で70mol%)、メチルトリエトキシシラン9.47g(シラン全体中で30mol%)、アセトン52.92gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.80gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル20/80の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように調整した。得られたポリマーは式(3−1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1700であった。
上記合成例1乃至合成例6および比較合成例1で得られたケイ素含有ポリマー、酸、硬化触媒、添加剤、溶媒、水を表1に示す割合で混合し、0.1μmのフッ素樹脂製のフィルターで濾過することによって、レジスト下層膜形成用組成物の溶液をそれぞれ調製した。表1中のポリマーの添加割合はポリマー溶液の添加量ではなく、ポリマー自体の添加量を示した。
表1中でマレイン酸はMA、N−(3−トリエトキシシリルプロピル)−4,5−ジヒドロイミダゾールはIMIDETEOS、トリフェニルスルホニウム硝酸塩はTPSNO3、マレイン酸モノトリフェニルスルフォニウムはTPSMA、トリフェニルスルホニウムトリフルオロ酢酸塩はTPSTFA、トリフェニルスルホニウムクロリドはTPSCl、トリフェニルスルホニウムカンファースルホン酸塩はTPSCS、トリフェニルスルホニウムトリフルオロメタンスルホン酸塩はTPSTf、トリフェニルスルホニウムアダマンタンカルボキシ−1,1,2−トリフルオロブタンスルホン酸塩はTPSAdTF、プロピレングリコールモノメチルエーテルアセテートはPGMEA、プロピレングリコールモノエチルエーテルはPGEE、プロピレングリコールモノメチルエーテルはPGMEと略した。水は超純水を用いた。各添加量は質量部で示した。
窒素下、100mLの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(4−1)、以下PCzFLと略す)9.37gを得た。
PCzFLの1H−NMRの測定結果は以下の通りであった。
1H−NMR(400MHz,DMSO−d6):δ7.03−7.55(br,12H)、δ7.61−8.10(br,4H)、δ11.18(br,1H)
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。
得られた樹脂20gに、架橋剤としてテトラメトキシメチルグリコールウリル(三井サイテック(株)製、商品名パウダーリンク1174)3.0g、触媒としてピリジニウムパラトルエンスルホネート0.30g、界面活性剤としてメガファックR−30N(DIC(株)製、商品名)0.06g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88g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有機下層膜形成組成物の溶液を調製した。
実施例1乃至14、比較例1で調製したSi含有レジスト下層膜形成組成物を、スピナーを用いてシリコンウエハ上にそれぞれ塗布した。ホットプレート上で200℃1分間加熱し、Si含有レジスト下層膜(膜厚0.05μm)を形成した。そして、これらのレジスト下層膜を分光エリプソメーター(J.A.Woollam社製、VUV−VASEVU−302)を用い、波長193nmでの屈折率(n値)及び光学吸光係数(k値、減衰係数とも呼ぶ)を測定した。
ドライエッチング速度の測定に用いたエッチャー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
RIE−10NR(サムコ製):O2
実施例1乃至14、比較例1で調製したSi含有レジスト下層膜形成組成物の溶液を、スピナーを用いてそれぞれシリコンウエハ上に塗布した。ホットプレート上で240℃1分間加熱し、Si含有レジスト下層膜をそれぞれ形成した(CF4ガスでのエッチング速度測定用として膜厚0.08μm、O2ガスでのエッチング速度測定用として膜厚0.05μm)。また、同様に有機下層膜形成組成物をスピナーを用い、シリコンウエハ上に塗膜を形成(膜厚0.20μm)した。
フッ素系ガスエッチングレートは、エッチングガスとしてCF4ガスを使用し実施例1乃至13、比較例1のSi含有レジスト下層膜のエッチングレートを測定した(単位はオングストローム/分)である。
酸素系ガス耐性の試験はエッチングガスとしてO2ガスを使用してドライエッチング速度を測定し、有機下層膜のドライエッチング速度に対する、実施例1乃至13、比較例1のSi含有レジスト下層膜のドライエッチング速度を比較し、その速度比を示した。
上記式で得られた有機下層膜(A層)形成組成物をシリコンウエハ上に塗布し、ホットプレート上で240℃で60秒間ベークし、膜厚200nmの有機下層膜(A層)を得た。その上に、実施例1乃至14、比較例1で得られたSi含有レジスト下層膜(B層)形成組成物をそれぞれ塗布し、ホットプレート上で240℃で60秒間ベークし、Si含有レジスト下層膜(B層)を得た。Si含有レジスト下層膜(B層)の膜厚は30nmであった。
B層の上に市販のフォトレジスト溶液(富士フイルム(株)製、商品名FAiRS−9521NT05)をスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて1分間加熱し、膜厚85nmのフォトレジスト膜(C層)を形成した。
(株)ニコン製NSR−S307Eスキャナー(波長193nm、NA、σ:0.85、0.93/0.85)を用い、現像後にフォトレジストのライン幅及びそのライン間の幅が0.062μm、すなわち0.062μmのラインアンドスペース(L/S)=1/1のデンスラインが形成されるように設定されたマスクに通して露光を行った。その後、ホットプレート上100℃で60秒間ベークし、冷却後、酢酸ブチル(溶剤現像液)を用いて60秒現像し、レジスト下層膜(B層)上にネガ型のパターンを形成した。レジスト裾形状の評価は、得られたフォトレジストパターンについて、パターン倒れ、大きなパターン剥がれやアンダーカット、ライン底部の太り(フッティング)が発生しないものを良好として評価した。
上記有機下層膜(A層)形成組成物をシリコンウエハ上に塗布し、ホットプレート上で215℃で60秒間ベークし、膜厚90nmの有機下層膜(A層)を得た。その上に、本発明の実施例13、比較例1で調製されたレジスト下層膜形成組成物溶液をそれぞれスピンコートし、240℃で1分間加熱することにより、レジスト下層膜(B)層(20nm)を形成した。そのハードマスク上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をそれぞれスピンコートし加熱を行い、EUVレジスト層(C)層を形成し、EUV露光装置(Micro Exposure Tool 略称MET)を用い、NA=0.30、σ=0.36/0.93 Quadropoleの条件で露光する。露光後、PEBを行い、クーリングプレート上で室温まで冷却し、現像及びリンス処理をし、レジストパターンを形成した。評価は、24nmのラインアンドスペースの形成可否、パターン断面観察によるパターン形状を評価した。
表3で良好とはフッティングやアンダーカットがなく矩形な形状であり、かつスペース部に著しい残渣がないという状態を示し、倒れとはレジストパターンが剥がれ倒壊しているという好ましくない状態を示し、ブリッジとはレジストパターンの上部もしくは下部同士が接触しているという好ましくない状態を示す。
上記有機下層膜(A層)形成組成物をシリコンウエハ上に塗布し、ホットプレート上で240℃で60秒間ベークし、膜厚90nmの有機下層膜(A層)を得た。その上に、本発明の実施例13、比較例1で調製されたレジスト下層膜形成組成物溶液をそれぞれスピンコートし、240℃で1分間加熱することにより、レジスト下層膜(B)層(20nm)を形成した。そのハードマスク上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をそれぞれスピンコートし加熱を行い、EUVレジスト層(C)層を形成し、EUV露光装置(Micro Exposure Tool、略称MET)を用い、NA=0.30、σ=0.36/0.93、Quadropoleの条件で露光する。露光後、PEBを行い、クーリングプレート上で室温まで冷却し、酢酸ブチル(溶剤現像液)を用いて60秒現像し、レジストパターンを形成した。評価は、24nmのラインアンドスペースの形成可否、パターン断面観察によるパターン形状を評価した。
表4で良好とはフッティングやアンダーカットがなく矩形な形状であり、かつスペース部に著しい残渣がないという状態を示し、倒れとはレジストパターンが剥がれ倒壊しているという好ましくない状態を示し、ブリッジとはレジストパターンの上部もしくは下部同士が接触しているという好ましくない状態を示す。
Claims (9)
- シランとして加水分解性シラン、その加水分解物、その加水分解縮合物、又はそれらの組み合わせを含み、該加水分解性シランが式(1)、式(2)、及び式(3):
(式(1)、式(2)、式(3)中、X1乃至X9はそれぞれ独立に酸素原子又はイオウ原子を示す。n、mはそれぞれ独立に1乃至4の整数を示す。nが1の場合はR1がヘテロ原子を有していてもよい炭素原子数1乃至40の炭化水素基を示し、nが2乃至4の場合はR1がヘテロ原子を有していてもよい炭素原子数2乃至40の炭化水素基を示す。
T1、T2、T3、及びT4はそれぞれ独立に炭素原子数2乃至40のヘテロ原子を有していてもよい炭化水素基を含む連結基を示す。
R3、R5、R7、及びR9はそれぞれ独立にアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、アミノ基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものである。
R2、R4、R6、及びR8はそれぞれ独立にアルコキシ基、アシルオキシ基、又はハロゲン基を示す。aはそれぞれ0乃至2の整数を示す。)で表される加水分解性シランからなる群より選ばれる少なくとも一種の加水分解性シランを含むものであるリソグラフィー用レジスト下層膜形成組成物。 - 該加水分解性シランが、式(1)、式(2)、及び式(3)で表される加水分解性シランからなる群から選ばれた少なくとも一種の加水分解性シランと、その他の加水分解性シランとの組み合わせであり、その他の加水分解性シランが式(4):
(式(4)中、R10はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものであり、R11はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、bは0乃至3の整数を示す。)で表される加水分解性シラン、及び式(5):
(式(5)中、R12はアルキル基で且つSi−C結合によりケイ素原子と結合しているものであり、R13はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、Yはアルキレン基又はアリーレン基を示し、cは0又は1の整数を示し、dは0又は1の整数である。)で表される加水分解性シランからなる群より選ばれた少なくとも一種の加水分解性シランである請求項1に記載のレジスト下層膜形成組成物。 - 請求項1に記載の式(1)、式(2)、及び式(3)で表される加水分解性シランからなる群より選ばれた少なくとも一種の加水分解性シランと、請求項2に記載の式(4)で表される加水分解性シランとの組み合わせからなる加水分解性シランの加水分解縮合物をポリマーとして含む請求項1に記載のレジスト下層膜形成組成物。
- 更に酸を含む請求項1乃至請求項3のいずれか1項に記載のレジスト下層膜形成組成物。
- 更に水を含む請求項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。
- 更に塩を含む請求項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の硬化物からなる、半導体基板上に形成されたレジスト下層膜。
- 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、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト膜形成組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、前記レジストパターンにより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と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。
- 半導体基板上に有機下層膜を形成する工程、その上に請求項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を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト膜形成組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、前記レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機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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