JP5012798B2 - 下層膜形成用組成物及びデュアルダマシン構造の形成方法 - Google Patents
下層膜形成用組成物及びデュアルダマシン構造の形成方法 Download PDFInfo
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- UACVJSDAGHJPNP-UHFFFAOYSA-M tert-butyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC=CC=C2C(OC(=O)OC(C)(C)C)=CC=C1[S+]1CCCC1 UACVJSDAGHJPNP-UHFFFAOYSA-M 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
- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical compound C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- UWIVZLWKBOZJFG-UHFFFAOYSA-N thiolan-1-ium trifluoromethanesulfonate Chemical compound C1CC[SH+]C1.[O-]S(=O)(=O)C(F)(F)F UWIVZLWKBOZJFG-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-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
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000000108 ultra-filtration Methods 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
- 239000008096 xylene Substances 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
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- H01L21/76808—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics characterised by the formation and the after-treatment of the dielectrics, e.g. smoothing by forming openings in dielectrics for dual damascene structures involving intermediate temporary filling with material
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Description
本発明の下層膜形成用組成物は、上記一般式(1)で表される繰り返し単位(i)、及び上記一般式(2)で表される繰り返し単位(ii)を含む重合体(A)と、溶剤と、を含有し、一般式(2)で表される繰り返し単位(ii)が、酸解離性基を有するものである。
重合体(A)は、上記一般式(1)で表される繰り返し単位(i)(以下「繰り返し単位(i)」と記す場合がある)、及び一般式(2)で表される繰り返し単位(ii)(以下「繰り返し単位(ii)」と記す場合がある)を含み、繰り返し単位(ii)が、酸解離性基を有するものである。このようなアセナフチレン構造を有することにより、本発明の下層膜形成用組成物により形成したレジスト下層膜をマスクパターンにして、無機被膜にパターンを転写する際の加工変換差を小さくすることができる。また、剥離液によって容易に繰り返し単位(ii)中の酸解離性基が解離するため、重合体(A)は剥離液によって容易に除去される。更に、繰り返し単位(ii)は、酸素含有量が多いため、アッシングにおけるプラズマによって良好に分解される。即ち、重合体(A)はアッシングによって容易に除去される。
繰り返し単位(i)において、R1は、水酸基、炭素数1〜6の置換可能なアルキル基、炭素数1〜6の置換可能なアルコキシ基、炭素数2〜10の置換可能なアルコキシカルボニル基、炭素数6〜14の置換可能なアリール基、または炭素数2〜6の置換可能なグリシジルエーテル基である。
本発明の下層膜形成用組成物は、重合体(A)は、繰り返し単位(i)とともに、繰り返し単位(ii)を含み、この繰り返し単位(ii)が、酸解離性基を有するものである。このように重合体(A)中に繰り返し単位(ii)を含有することによって、重合体(A)は、当初はアルカリ不溶性またはアルカリ難溶性を示すものであるが、酸または熱の作用を受けることにより、容易に、アルカリ易溶性を示すことができる。即ち、低誘電絶縁膜(無機被膜)を損傷させることなく、レジスト下層膜を剥離液によって、容易に除去することができる。また、重合体(A)に柔軟性を付与するためビアホールへの埋め込み性を向上させるという利点がある。
本発明の下層膜形成用組成物は、溶剤を含有するものである。溶剤は、重合体(A)を溶解しうるものである。例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル等のエチレングリコールモノアルキルエーテル類;エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノ−n−プロピルエーテルアセテート、エチレングリコールモノ−n−ブチルエーテルアセテート等のエチレングリコールモノアルキルエーテルアセテート類;ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジ−n−プロピルエーテル、ジエチレングリコールジ−n−ブチルエーテル等のジエチレングリコールジアルキルエーテル類;トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテル等のトリエチレングリコールジアルキルエーテル類;
酸発生剤は、露光または加熱により酸を発生する成分である。本発明の下層膜形成用埋め込み組成物は、酸発生剤を含有することにより、光及び/または熱の刺激によってレジスト下層膜中に発生した酸が、繰り返し単位(ii)を剥離液により更に容易に除去されるという利点がある。
架橋剤は、得られるレジスト下層膜と、その上に形成されるフォトレジスト膜との間のインターミキシングを防止し、更には該レジスト下層膜のクラックを防止する作用を有する成分である。このような架橋剤としては、多核フェノール類や、種々の市販の硬化剤を使用することができる。
本発明のデュアルダマシン構造の形成方法は、基板上に、この基板側から順に低誘電絶縁膜、レジスト下層膜、及びフォトレジスト膜を形成した後、露光及び現像によりフォトレジスト膜、レジスト下層膜、及び低誘電絶縁膜の順にレジストパターンを形成するデュアルダマシン構造の形成方法であって、レジスト下層膜は、上記下層膜形成用組成物により形成し、低誘電絶縁膜にレジストパターンを形成した後にレジスト下層膜を剥離液により除去するものである。
還流管を装着したセパラブルフラスコに、窒素気流下で、8−メチル−8−t−ブトキシカルボニルメトキシカルボニルテトラシクロ[4.4.0.12,5.17,10]ドデカ−3−エン(単量体(α))29質量部、8−メチル−8−ヒドロキシテトラシクロ[4.4.0.12,5.17,10]ドデカ−3−エン(単量体(β))10質量部、無水マレイン酸(単量体(γ))18質量部、2,5−ジメチル−2,5−ヘキサンジオールジアクリレート4質量部、t−ドデシルメルカプタン1質量部、アゾビスイソブチロニトリル4質量部及び1,2−ジエトキシエタン60質量部を仕込み、攪拌しつつ70℃で6時間重合した。その後、反応溶液を大量のn−ヘキサン/i−プロピルアルコール(質量比=1/1)混合溶媒中に注いで、反応溶液中の樹脂を凝固させた。凝固した樹脂を上記混合溶媒で数回洗浄した後、真空乾燥して、上記単量体(α)、(β)、及び(γ)のそれぞれに由来する下記繰り返し単位(a)、(b)、及び(c)を有する樹脂を得た(収率60質量%)。なお、この樹脂は、モル比が64:18:18であり、Mwが27,000であった。
以下の各合成例において得られる重合体、及び上記調製例1で得られた樹脂(この樹脂については重量平均分子量(Mw)のみ)の重量平均分子量(Mw)及び数平均分子量(Mn)は、東ソー社製GPCカラム(G2000HXL:2本、G3000HXL:1本)を用い、流量:1.0ml/分、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、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフ(検出器:示差屈折計)により測定した。
[重合体(A−1)の合成]:
予め、以下に示す単量体(M1−1)22.75g(50モル%)、以下に示す単量体(M2−1)27.25g(50モル%)を2−ブタノン200gに溶解し、この溶解液に、更にジメチル2,2’−アゾビス(2−メチルプロピオネート)10.20gを投入した単量体溶液を準備した。一方、100gの2−ブタノンを投入した1000mlの三口フラスコを30分窒素パージした後、反応釜を攪拌しながら80℃に加熱しつつ、上記三口フラスコに上記単量体溶液を滴下漏斗により3時間かけて滴下した。滴下開始を重合開始時間とし、重合反応を6時間実施した。重合終了後、重合溶液を水冷して30℃以下に冷却し、2000gのメタノールへ投入した後、析出する白色粉末を濾別した。濾別された白色粉末を2℃に保持した400gのメタノールにてスラリー状態のまま洗浄した後、濾別し、50℃にて17時間乾燥して黄白色粉末である重合体を得た(36.5g、収率73%)。この重合体はMwが2000、Mw/Mnが1.50であった。この重合体(A)を重合体(A−1)とする。
[重合体(A−2)の合成]:
単量体(M1−1)50モル%、単量体(M2−1)30モル%、単量体(M3−1)20モル%を用いる以外は合成例1と同等の手法により黄白色粉末である重合体を得た(収率68%)。この重合体は、Mwが1500、Mw/Mnが1.80であった。この重合体(A)を重合体(A−2)とする。
[重合体(A−3)の合成]:
単量体(M1−1)40モル%、単量体(M2−1)30モル%、単量体(M2−2)30モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率77%)。この重合体はMwが2200、Mw/Mnが1.82であった。この重合体(A)を重合体(A−3)とする。
[重合体(A−4)の合成]:
単量体(M1−1)40モル%、単量体(M2−1)30モル%、単量体(M2−3)30モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率78%)。この重合体はMwが1800、Mw/Mnが1.47であった。この重合体(A)を重合体(A−4)とする。
[重合体(A−5)の合成]:
単量体(M1−2)40モル%、単量体(M2−1)60モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率81%)。この重合体はMwが1760、Mw/Mnが1.55であった。この重合体(A)を重合体(A−5)とする。
[重合体(A−6)の合成]:
単量体(M1−2)40モル%、単量体(M2−1)40モル%、単量体(M3−1)20モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率65%)。この重合体はMwが2520、Mw/Mnが1.77であった。この重合体(A)を重合体(A−6)とする。
[重合体(A−7)の合成]:
単量体(M1−2)40モル%、単量体(M2−1)30モル%、単量体(M2−2)30モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率82%)。この重合体はMwが1700、Mw/Mnが1.46であった。この重合体(A)を重合体(A−7)とする。
[重合体(A−8)の合成]:
単量体(M1−2)40モル%、単量体(M2−1)30モル%、単量体(M2−3)30モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率79%)。この重合体はMwが1930、Mw/Mnが1.75であった。この重合体(A)を重合体(A−8)とする。
[重合体(A−9)の合成]:
単量体(M1−1)40モル%、単量体(M1−3)40モル%、単量体(M2−1)20モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率48%)。この重合体はMwが1340、Mw/Mnが2.10であった。この重合体(A)を重合体(A−9)とする。
[重合体(A−10)の合成]:
単量体(M1−1)40モル%、単量体(M1−3)50モル%、単量体(M2−1)10モル%を用いる以外は合成例1と同等の手法で黄白色粉末の重合体を得た(収率48%)。この重合体はMwが1400、Mw/Mnが2.00であった。この重合体(A)を重合体(A−10)とする。
上記重合体(A−1)〜重合体(A−10)の各モノマーの組成比を表1に示す。
上記重合体(A−1)10質量部、酸発生剤としてビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート(商品名「BBI−109」、ミドリ化学社製、表2中「C−1」と示す)0.5質量部及び架橋剤として下記式D−1に示すテトラメトキシメチルグリコールウリル(商品名「ニカラックMX−270」、日本カーバイド工業社製、表2中「D−1」と示す)0.5質量部を、プロピレングリコールモノメチルアセテート89質量部に溶解した後、溶液を孔径0.1μmのメンブランフィルターでろ過して、下層膜形成用組成物(I)を調製した。なお、表2は、重合体(A)、酸発生剤、及び架橋剤の種類を示す。また、表2中、「C−2」は、4−n−ブトキシ−1−ナフチ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(商品名「TORAX」、旭電化工業社製)を、「D−2」は、ヘキサメトキメチルトリアジン(商品名「ニカラックMW−100LM」、日本カーバイド工業社製)を示す。
ビアサイズ:140nm、ビアピッチ:1H/1.2S、深さ:1000nmに加工されたテトラエチルオルソシリケート(TEOS)基板上に下層膜形成用組成物(I)をスピンコートした後、180℃で60秒間、その後300℃で60秒間ホットプレート上で加熱して、ビアホール内とTEOS基板の表面上に膜厚が300nmであるレジスト下層膜を作製した。下層膜形成用組成物(I)のビアホール内への埋め込みの有無を走査型電子顕微鏡により観察して評価した。評価基準は、ビアホール内に埋め込まれている場合を良好(「○」)とし、そうでない場合を不良(「×」)とした。なお、表3中、「埋め込み性」は、本評価(ビアへの埋め込み性)を示す。
また、下層膜形成用組成物(I)により形成されるレジスト下層膜の各種評価を行うため、以下のように、ArF用ポジ型レジストパターンを形成した。
下層膜形成用組成物により形成したレジスト下層膜の反射防止膜としての機能を評価するため、上記ポジ型レジストパターンのパターン形状を走査型電子顕微鏡により観察して評価した。評価基準は、パターン形状が矩形の場合を良好(「○」)、そうでない場合を不良(「×」)とした。なお、表3、5中、「レジスト形状」は、本評価(現像後のパターン形状)を示す。
また、下層膜形成用組成物により形成したレジスト下層膜の反射防止膜としての機能を評価するため、上記ポジ型レジストパターンの定在波の影響の有無を走査型電子顕微鏡により観察して評価した。評価基準は、定在波が無い場合を良好(「○」)、ある場合を不良(「×」)とした。なお、表3、5中、「定在波防止効果」は、本評価(定在波防止効果)を示す。
下層膜形成用組成物により形成したレジスト下層膜のパターン転写性能及びエッチング選択性を評価するため、上記ポジ型レジストパターンの形成に用いたレジスト下層膜のエッチング耐性を以下の方法により評価した。スピンコート法によりレジスト下層膜を形成し、エッチング装置EXAM(神鋼精機社製)を使用して、CF4/Ar/O2(CF4:40mL/分、Ar:20mL/分、O2:5mL/分;圧力:20Pa;RFパワー:200W;処理時間:40秒;温度:15℃)で上記レジスト下層膜をエッチング処理し、エッチング処理前後のレジスト下層膜の膜厚を測定して、エッチングレートを算出した。
下層膜形成用組成物により形成したレジスト下層膜の剥離容易性を評価するため、上記ポジ型レジストパターンの形成に用いたレジスト下層膜のF化処理後の剥離性を以下の方法により評価した。基板上に、スピンコート法によりレジスト下層膜を形成し、エッチング装置EXAM(神鋼精機社製)を用いて、CF4(CF4:100mL/分、;圧力:30Pa;RFパワー:200W;処理時間:60秒;温度:15℃)でレジスト下層膜をフッ化処理し、フッ化処理したレジスト下層膜を備えた基板を得た。得られた基板を2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で浸漬し(現像液による剥離を行い)、水洗し、乾燥して行った。評価は、剥離処理後のレジスト下層膜の膜厚を測定して行った。評価基準は、剥離処理後10分以内に膜厚が0nmとなる場合を「◎」、10分〜30分で膜厚が0nmとなる場合を「○」、30分以上経過しても膜厚が0nmにならない場合を「×」とした。なお、表3、5中、「現像液剥離性」は、本評価(現像液剥離性)を示す。
上記現像液剥離性の評価と同様にしてフッ化処理したレジスト下層膜を備えた基板を得た。得られた基板をNH3プラズマアッシング条件(圧力:0.1Torr、高周波電力:550W、NH3=150sccm、基板温度:20℃)でアッシング処理し、アッシング処理後のレジスト下層膜の膜厚を測定して行った。評価基準は、剥離処理後5分未満に膜厚が0nmとなる場合を「○」、5分以上経過しても膜厚が0nmにならない場合を「×」とした。なお、表3、5中、「アッシング剥離性」は、本評価(アッシング剥離性)を示す。
実施例1は、ビアへの埋め込み性が○、現像後のパターン形状が○、定在波防止効果が○、エッチング耐性が◎、及び現像液剥離性が○、アッシング剥離性が○であり、全ての評価において良好な結果が得られることが確認できた。
表2に示す成分を用いること以外は、上述した実施例1と同様の配合量及び方法として実施例2〜20の組成物(II)〜(XX)を調製し、各種評価を行った。評価結果を表3に示す。
表4に示す成分を用いること以外は、上述した実施例1と同様の配合量及び方法として比較例1〜3の組成物を調製し、各種評価を行った。評価結果を表5に示す。なお、表4中、「R−1」はポリアセナフチレン(JSR社製)、「R−2」はポリヒドロキシスチレン(商品名:マルカリンカー、丸善石油化学社製)、「R−3」はポリメタクリル酸(JSR社製)、「NFC1400」(商品名:NFC1400、JSR社製)、「NFC1500」(商品名:NFC1500、JSR社製)を示す。
表3により、本発明の下層膜形成用組成物により形成したレジスト下層膜は、反射防止膜として優れた反射防止効果を有することが確認できた。本発明の下層膜形成用組成物は、繰り返し単位(ii)を有する重合体(A)を含有するため、この重合体(A)の柔軟性が付与され、ビアホールへの埋め込み性の悪さが改善されており、良好な埋め込み性能を有することが確認できた。また、上記レジスト下層膜は、アッシング及び剥離液によって容易に除去が可能であることが確認できた。更に、上記レジスト下層膜は、高いエッチング耐性が確認できた。これは、重合体(A)が繰り返し単位(i)を有するためであると考えられる。
Claims (4)
- 下記一般式(1)で表される繰り返し単位(i)、及び下記一般式(2)で表される繰り返し単位(ii)を含む重合体(A)と、
溶剤と、を含有し、前記一般式(2)で表される繰り返し単位(ii)が、酸解離性基を有するものである下層膜形成用組成物。
- 更に、酸発生剤及び/または架橋剤を含有する請求項1に記載の下層膜形成用組成物。
- 基板上に、この基板側から順に低誘電絶縁膜、レジスト下層膜、及びフォトレジスト膜を形成した後、露光及び現像により前記フォトレジスト膜、前記レジスト下層膜、及び前記低誘電絶縁膜の順にレジストパターンを形成するデュアルダマシン構造の形成方法であって、
前記レジスト下層膜は、請求項1または2に記載の下層膜形成用組成物により形成し、
前記低誘電絶縁膜に前記レジストパターンを形成した後に前記レジスト下層膜を剥離液により除去するデュアルダマシン構造の形成方法。 - 前記剥離液が、水溶性アミン及び/または第4級アンモニウム水酸化物を含有する請求項3に記載のデュアルダマシン構造の形成方法。
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JP2002244297A (ja) * | 2001-02-21 | 2002-08-30 | Shin Etsu Chem Co Ltd | レジスト材料及びパターン形成方法 |
JP2004168748A (ja) * | 2002-07-31 | 2004-06-17 | Jsr Corp | アセナフチレン誘導体、重合体および反射防止膜形成組成物 |
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