JP6059791B2 - 有機膜形成用化合物、これを用いた有機膜材料、有機膜形成方法、パターン形成方法 - Google Patents
有機膜形成用化合物、これを用いた有機膜材料、有機膜形成方法、パターン形成方法 Download PDFInfo
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- JP6059791B2 JP6059791B2 JP2015232690A JP2015232690A JP6059791B2 JP 6059791 B2 JP6059791 B2 JP 6059791B2 JP 2015232690 A JP2015232690 A JP 2015232690A JP 2015232690 A JP2015232690 A JP 2015232690A JP 6059791 B2 JP6059791 B2 JP 6059791B2
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- 125000004122 cyclic group Chemical group 0.000 claims description 41
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
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- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
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- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 7
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
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- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 5
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Images
Classifications
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Description
このような化合物を半導体装置などの製造工程における微細加工に適用される多層レジスト膜形成に用いられるレジスト下層膜材料に用いることで、高いドライエッチング耐性を有するとともに、高度な埋め込み、あるいは平坦化特性を併せ持つレジスト下層膜を形成するためのレジスト下層膜材料、レジスト下層膜形成方法、パターン形成方法を提供することが可能となる。また、本発明は、多層レジストプロセス以外の半導体装置製造工程における平坦化に適用可能な、優れた埋め込み、あるいは平坦化特性を有する半導体装置製造用平坦化材料を提供することが可能となる。
(A)前記一般式(iii)で示される化合物、(B)前記一般式(iv)で示される部分構造を有する化合物、(C−1)繰り返し単位の一部として前記一般式(iv)で示される部分構造を有する高分子化合物、(C−2)前記一般式(v)で示される部分構造を有する高分子化合物、(C−3)前記一般式(vi)で示される部分構造を有する高分子化合物、又は(C−4)前記一般式(vii)で示される部分構造を有する高分子化合物のうち、いずれか一つ以上を用いたものであることを特徴とする有機膜材料を提供する。
A−CHO (4)
(式中、Aは水素原子、炭素数1〜10の炭化水素基、及び炭素数6〜20の置換又は非置換の芳香族炭化水素基のいずれかである。)
本発明で提供される化合物が有する最も重要な構造は、下記一般式(i)又は(ii)で示される部分構造である。
反応式1Aで使用されるアルコールの保護基としては一般的に知られているものでよく、アセタールやシリル基などが好ましい。
P1)有機ハロゲン化合物との縮合反応
P2)ポリオールとの縮合反応
を挙げ、以下、具体的に示す。
芳香族化合物(2A−Ia’)と有機ハロゲン化合物との縮合反応は通常、無溶媒又は溶媒中で、室温又は必要に応じて冷却又は加熱下に行う。
芳香族化合物(2A−Ia’)とポリオールとの縮合反応は通常、無溶媒又は溶媒中で、室温又は必要に応じて冷却又は加熱下に行う。
還元剤としては、水素化ホウ素ナトリウムや水素化リチウムアルミニウムなど一般的に知られている化合物を使用できる。反応温度は−70℃から150℃の間で可能であるが、反応速度等を鑑みて適宜選択可能である。
使用できる溶媒は、ジエチルエーテル、ジブチルエーテル、テトラヒドロフラン、1,4−ジオキサン、シクロペンチルメチルエーテル等のエーテル類、ベンゼン、トルエン、キシレン、メシチレン、ヘキサン、ヘプタン、オクタン、イソオクタン等の炭化水素類、N,N,N’,N’−テトラメチルエチレンジアミン、ヘキサメチルホスホリックトリアミド、N,N−ジメチルホルムアミド等の非プロトン性極性溶媒類を単独又は混合して用いることができる。
P1)有機ハロゲン化合物との縮合反応
P2)ポリオールとの縮合反応
を挙げ、説明をする。
前記一般式(iii)で示される化合物と有機ハロゲン化合物との縮合反応は通常、無溶媒又は溶媒中で、室温又は必要に応じて冷却又は加熱下に行う。
前記一般式(iii)で示される化合物とポリオールとの縮合反応は通常、無溶媒又は溶媒中で、室温又は必要に応じて冷却又は加熱下に行う。
A−CHO (4)
(式中、Aは水素原子、炭素数1〜10の炭化水素基、及び炭素数6〜20の置換又は非置換の芳香族炭化水素基のいずれかである。)
ラジカル開始剤としては、アゾビスイソブチロニトリル、アゾビスイソブタン酸ジメチル等のアゾ化合物、過酸化ベンゾイル等の過酸化物等を用いることができる。
(F)酸発生剤は熱分解によって酸を発生するものや、光照射によって酸を発生するものがあるが、いずれのものも添加することができる。具体的には、特開2007−199653号公報中の(0061)〜(0085)段落に記載されている材料を添加することができる。
ベーク中の雰囲気としては空気中でもよいし、N2、Ar、He等の不活性ガスを封入してもよい。また、ベーク温度等は、上記と同様とすることができる。
また、露光光としては、波長300nm以下の高エネルギー線、具体的には248nm、193nm、157nmのエキシマレーザー、3〜20nmの軟X線、電子ビーム、X線等を挙げることができる。
なお、被加工基板としては、特に限定されるものではなく、Si、α−Si、p−Si、SiO2、SiN、SiON、W、TiN、Al等の基板や、該基板上に被加工層が成膜されたもの等が用いられる。被加工層としては、Si、SiO2、SiON、SiN、p−Si、α−Si、W、W−Si、Al、Cu、Al−Si等種々のLow−k膜及びそのストッパー膜が用いられ、通常50〜10,000nm、特に100〜5,000nm厚さに形成し得る。なお、被加工層を成膜する場合、基板と被加工層とは、異なる材質のものが用いられる。
3層レジストプロセスの場合、図1(A)に示したように、基板1の上に積層された被加工層2上に本発明の有機膜材料を用いてレジスト下層膜3を形成した後、レジスト中間層膜4を形成し、その上にレジスト上層膜5を形成する。
なお、分子量の測定法は具体的に下記の方法により行った。テトラヒドロフランを溶離液としたゲルパーミエーションクロマトグラフィー(GPC)によるポリスチレン換算の重量平均分子量(Mw)、数平均分子量(Mn)を求め、分散度(Mw/Mn)を求めた。
IR(ATR法):ν=3288、3065、3039、2933、2861、1608、1586、1466、1447、1376、1315、1285、1248、1194、1156、1106、1072、1031、952、940、829、777、739、732cm−1。
1H−NMR(600MHz in DMSO−d6):δ=0.59(4H、m)、1.77(4H、m)、5.38(2H、−OH)、7.22(4H、t)、7.29(4H、t)、7.35(4H、d)、7.66(4H、d)ppm。
13C−NMR(150MHz in DMSO−d6):δ=23.83、39.63、80.93、119.69、123.43、127.48、128.09、139.00、149.62ppm。
IR(ATR法):ν=3527、3056、2932、2856、1704、1634、1603、1506、1475、1446、1376、1347、1278、1215、1175、1145、1032、952、895、861、807、769、754、738cm−1。
1H−NMR(600MHz in DMSO−d6):δ=0.49(4H、m)、2.31(4H、t)、6.58(2H、d−d)、6.93(2H、s−d)、6.98(2H、d−d)、7.16(4H、d)、7.22(4H、t−d)、7.30(2H、d)、7.34(4H、t−d)、7.64(2H、d)、7.73(s−d)、7.86(4H、d)、9.60(2H、−OH)ppm。
13C−NMR(150MHz in DMSO−d6):δ=24.27、36.62、58.10、108.15、118.39、120.08、123.90、124.17、125.75、125.78、127.19、127.51、127.65、129.32、133.05、138.86、140.25、151.28、155.07ppm。
TG−DTA(−5%重量減少温度、Air中):263℃
TG−DTA(−5%重量減少温度、He中):282℃
DSC(ガラス転移温度):107℃
IR(ATR法):ν=3091、2957、2927、2874、1878、1636、1588、1575、1486、1466、1445、1408、1387、1316、1299、1287、1240、1199、1170、1116、1102、1071、1050、1001、975、824、804、744cm−1。
1H−NMR(600MHz in CDCL3):δ=1.96(4H、quint)、3.99(4H、quint)、6.77(4H、d−t)、7.36(4H、d−t)ppm。
13C−NMR(150MHz inCDCL3):δ=25.86、67.63、112.76、116.24、132.23、158.02ppm。
IR(ATR法):ν=3381、3174、3053、2955、2861、160、1581、1508、1472、1448、1413、1381、1292、1243、1166、1114、1097、1011、985、947、920、824、774、752、736cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.78(4H、m)、3.92(4H、m)、6.19(2H、−OH)、6.73(4H、d−t)、7.11(4H、d−t)、7.20〜7.22(8H、m)、7.33(4H、m)、7.78(4H、d)ppm。
13C−NMR(150MHz in DMSO−d6):δ=25.38、66.99、82.22、113.85、120.00、124.57、126.25、127.95、128.33、136.88、139.01、151.47、157.42ppm。
IR(ATR法):ν=3403、3033、2950、2871、1609、1506、1472、1446、1293、1243、1175、1106、1049、1013、971、915、821、747、729cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.76(4H、m)、3.90(4H、m)、6.62(4H、d−t)、6.75(4H、d−t)、6.89(4H、d−t)、6.96(4H、d−t)、7.26(4H、t−d)、7.34(8H、m)、7.87(4H、d)、9.30(2H、−OH)ppm。
13C−NMR(150MHz in DMSO−d6):δ=25.35、63.55、66.94、114.06、114.92、120.33、125.85、127.30、127.66、128.59、128.63、135.67、137.68、139.29、151.44、156.00、157.20ppm。
TG−DTA(−5%重量減少温度、Air中):348℃
TG−DTA(−5%重量減少温度、He中):339℃
DSC(ガラス転移温度):112℃
IR(ATR法):ν=3526、3055、2964、1634、1605、1578、1504、1474、1446、1390、1289、1277、1245、1179、1120、1013、979、959、945、898、860、829、812、752、738cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.77(4H、m)、3.92(4H、m)、6.77(4H、d−t)、6.99(2H、d−d)、7.02(4H、m)、7.04(2H、s−d)、7.19(2H、d−d)、7.28(4H、t)、7.34〜7.38(6H、m)、7.44(2H、d)、7.52(2H、d)、7.56(2H、d)、7.90(4H、d)、9.67(2H、−OH)ppm。
13C−NMR(150MHz in DMSO−d6):δ=25.45、61.98、66.96、108.30、114.19、118.69、120.45、125.05、125.96、126.19、126.85、127.12、127.49、127.73、128.72、129.28、133.29、137.25、139.44、139.66、151.00、155.30、157.32ppm。
TG−DTA(−5%重量減少温度、Air中):395℃
TG−DTA(−5%重量減少温度、He中):368℃
DSC(ガラス転移温度):138℃
IR(ATR法):ν=3091、2942、2910、2864、1885、1637、1589、1576、1490、1474、1398、1290、1248、1175、1119、1105、1076、1025、1001、830、809、733cm−1。
1H−NMR(600MHz in CDCL3):δ=1.53(4H、quint)、1.80(4H、quint)、3.93(4H、t)、6.77、(4H、d−t)、7.36(4H、d−t)ppm。
13C−NMR(150MHz inCDCL3):δ=25.78、29.07、68.02、112.61、116.25、132.18、158.15ppm。
IR(ATR法):ν=3529、3443、3038、2935、2868、1608、1582、1471、1448、1415、1385、1295、1248、1166、1115、1099、1031、1010、995、946、919、827、770、750、734cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.39(4H、m)、1.64(4H、m)、3.86(4H、t)、6.18(2H、−OH)、6.76(4H、d−t)、7.11(4H、d−t)、7.21〜7.25(8H、m)、7.34(4H、m)、7.77(4H、d)ppm。
13C−NMR(150MHz in DMSO−d6):δ=25.23、28.59、67.19、82.22、113.82、119.99、124.57、126.24、127.93、128.32、136.80、139.01、151.48、157.48ppm。
IR(ATR法):ν=3540、3414、3062、2940、2866、1609、1506、1474、1447、1394、1330、1292、1266、1238、1181、1171、1118、1105、1017、917、823、803、746、731cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.38(4H、m)、1.64(4H、m)、3.85(4H、t)、6.61(4H、d−t)、6.75(4H、d−t)、6.89(4H、d−t)、6.96(4H、d−t)、7.27(4H、t−d)、7.32〜7.36(8H、m)、7.87(4H、m)、9.30(2H、−OH)ppm。
13C−NMR(150MHz in DMSO−d6):δ=25.22、28.58、63.56、67.19、114.03、114.93、120.35、125.86、127.32、127.65、128.61、128.64、135.69、137.61、139.30、151.45、156.02、157.27ppm。
TG−DTA(−5%重量減少温度、Air中):350℃
TG−DTA(−5%重量減少温度、He中):356℃
DSC(ガラス転移温度):109℃
IR(ATR法):ν=3545、3361、3062、2941、2874、1634、1605、1580、1505、1475、1447、1390、1348、1278、1250、1223、1204、1180、1147、1122、1021、959、923、898、884、862、839、823、807、751、737cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.40(4H、m)、1.65(4H、m)、3.87(4H、t)、6.79(4H、d)、6.97(4H、d−d)、7.00〜7.04(6H、m)、7.18(2H、d−d)、7.29(4H、t)、7.34〜7.39(6H、m)、7.44(4H、d)、7.51(2H、d)、7.56(2H、d)、7.91(4H、d)、9.67(2H、−OH)ppm。
13C−NMR(150MHz in DMSO−d6):δ=25.22、28.58、64.14、67.20、108.30、114.15、118.70、120.48、125.05、125.98、126.21、126.87、127.12、127.52、127.76、128.73、129.30、133.29、137.19、139.45、139.68、151.01、155.30、157.39ppm。
TG−DTA(−5%重量減少温度、Air中):388℃
TG−DTA(−5%重量減少温度、He中):398℃
DSC(ガラス転移温度):132℃
GPC(RI):Mw=2070、Mn=1390、Mw/Mn=1.49
n=〜1.8(Mnから算出)、〜2.0(1H−NMRから算出)。
IR(ATR法):ν=3546、3035、2944、1607、1506、1472、1447、1390、1292、1243、1176、1115、1013、915、823、745、729cm-1。
TG−DTA(−5%重量減少温度、Air中):361℃
TG−DTA(−5%重量減少温度、He中):366℃
DSC(ガラス転移温度):136℃
GPC(RI):Mw=2510、Mn=1490、Mw/Mn=1.68
n=〜3.8(Mnから算出)、〜4.0(1H−NMRから算出)。
IR(ATR法):ν=3526、3034、2948、1606、1505、1427、1446、1388、1290、1242、1175、1113、1013、915、822、744、729cm−1。
TG−DTA(−5%重量減少温度、Air中):363℃
TG−DTA(−5%重量減少温度、He中):368℃
DSC(ガラス転移温度):139℃
GPC(RI):Mw=3880、Mn=1570、Mw/Mn=2.47
GPC(RI):Mw=2320、Mn=1350、Mw/Mn=1.72
GPC(RI):Mw=3410、Mn=1880、Mw/Mn=1.81
GPC(RI):Mw=4040、Mn=2580、Mw/Mn=1.57
IR(ATR法):ν=3332、2955、2929、2908、2870、1612、1586、1512、1474、1448、1386、1303、1249、1212、1198、1174、1167、1110、1052、1039、1009、997、977、929、827、808、790cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.84(4H、m)、3.99(4H、t)、4.39(4H、d)、5.02(−OH、t)、6.87(4H、d−t)、7.20(4H、d−t)ppm。
13C−NMR(150MHz in DMSO−d6):δ=26.00、63.12、67.63、114.57、128.45、135.01、158.04ppm。
GPC(RI):Mw=1720、Mn=880、Mw/Mn=1.95
GPC(RI):Mw=6960、Mn=1250、Mw/Mn=5.57
GPC(RI):Mw=20530、Mn=1160、Mw/Mn=17.70
GPC(RI):Mw=18110、Mn=1840、Mw/Mn=9.84
GPC(RI):Mw=3580、Mn=1350、Mw/Mn=2.64
IR(ATR法):ν=3206、2959、2914、2873、1601、1590、1493、1472、1455、1396、1375、1305、1282、1156、1111、1060、1039、1016、945、926、850、838、749cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.88(4H、m)、4.02(4H、t)、4.52(4H、d)、4.95(−OH、t)、6.90〜6.95(4H、m)、7.18(2H、t−d)、7.38(2H、d)ppm。
13C−NMR(150MHz in DMSO−d6):δ=25.75、57.98、67.29、111.11、120.18、127.02、127.66、130.68、155.44ppm。
GPC(RI):Mw=3800、Mn=2190、Mw/Mn=1.74
IR(ATR法):ν=3327、2936、2921、2852、1611、1582、1512、1475、1464、1395、1300、1171、1113、1049、1016、836、820、800cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.24〜1.36(8H、m)、1.38(4H、quint)、1.67(4H、quint)、3.90(4H、t)、4.39(4H、d)、5.01(−OH、t)、6.84(4H、d−t)、7.18(4H、d)ppm。
GPC(RI):Mw=6020、Mn=1230、Mw/Mn=4.89
GPC(RI):Mw=13250、Mn=2410、Mw/Mn=5.50
GPC(RI):Mw=8760、Mn=2460、Mw/Mn=3.56
上記化合物(A1)〜(A20)、液状添加剤(B1)、(R1)〜(R3)で示される芳香環含有ベース樹脂、CR1、CR2で示される架橋剤、AG1で示される酸発生剤、溶剤を、FC−4430(住友スリーエム(株)製)0.1質量%を含む溶媒中に表1に示す割合で溶解させ、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材料(ULD−1〜23、比較UDL−1〜5)をそれぞれ調製した。
上記で調製したレジスト下層膜材料(UDL−1〜23、比較UDL−1〜5)をシリコン基板上に塗布し、表2に記載の条件で焼成した後、膜厚を測定し、その上にPGMEA溶媒をディスペンスし、30秒間放置しスピンドライ、100℃で60秒間ベークしてPGMEAを蒸発させ、膜厚を測定しPGMEA処理前後の膜厚差を求めた。
上記と同様にレジスト下層膜を形成し、下記条件でCF4/CHF3系ガスでのエッチング試験を行った。
エッチング条件
チャンバー圧力 40.0Pa
RFパワー 1,300W
CHF3ガス流量 30ml/min
CF4ガス流量 30ml/min
Arガス流量 100ml/min
時間 60sec
図2のように、前記のレジスト下層膜材料をそれぞれ、密集ホールパターン(ホール直径0.16μm、ホール深さ0.50μm、隣り合う二つのホールの中心間の距離0.32μm)を有するSiO2ウエハー基板上に塗布し、ホットプレートを用いて180℃で60秒間加熱し、レジスト下層膜8を形成した。使用した基板は図2(G)(俯瞰図)及び(H)(断面図)に示すような密集ホールパターンを有する下地基板7(SiO2ウエハー基板)である。得られた各ウエハー基板の断面形状を、走査型電子顕微鏡(SEM)を用いて観察し、ホール内部にボイド(空隙)なく、レジスト下層膜で充填されているかどうかを確認した。結果を表4に示す。埋め込み特性に劣るレジスト下層膜材料を用いた場合は、本評価において、ホール内部にボイドが発生する。埋め込み特性が良好なレジスト下層膜材料を用いた場合は、本評価において、図2(I)に示されるようにホール内部にボイドなくレジスト下層膜が充填される。
前記のレジスト下層膜材料をそれぞれ、巨大孤立トレンチパターン(図3(J)、トレンチ幅10μm、トレンチ深さ0.50μm)を有する下地基板9(SiO2ウエハー基板)上に塗布し、表5に記載の条件で焼成した後、トレンチ部分と非トレンチ部分のレジスト下層膜10の膜厚の差(図3(K)中のdelta 10)を、走査型電子顕微鏡(SEM)を用いて観察した。結果を表5に示す。本評価において、膜厚の差が小さいほど、平坦化特性が良好であるといえる。なお、本評価では、深さ0.50μmのトレンチパターンを、通常膜厚約0.3μmのレジスト下層膜材料を用いて平坦化しており、平坦化特性の優劣を評価するために、特殊な厳しい評価条件となっている。
レジスト下層膜材料(UDL−1〜23)を、それぞれ、トレンチパターン(トレンチ幅10μm、トレンチ深さ0.10μm)を有するSiO2ウエハー基板上に塗布し、表8に記載の条件で焼成することにより、レジスト下層膜を形成した。その上にレジスト中間層膜材料SOG1を塗布して200℃で60秒間ベークして膜厚35nmのレジスト中間層膜を形成し、その上にレジスト上層膜材料のArF用SLレジストを塗布し、105℃で60秒間ベークして膜厚100nmのフォトレジスト膜を形成した。フォトレジスト膜上に液浸保護膜材料(TC−1)を塗布し90℃で60秒間ベークし膜厚50nmの保護膜を形成した。
チャンバー圧力 10.0Pa
RFパワー 1,500W
CF4ガス流量 75sccm
O2ガス流量 15sccm
時間 15sec
チャンバー圧力 2.0Pa
RFパワー 500W
Arガス流量 75sccm
O2ガス流量 45sccm
時間 120sec
チャンバー圧力 2.0Pa
RFパワー 2,200W
C5F12ガス流量 20sccm
C2F6ガス流量 10sccm
Arガス流量 300sccm
O2 60sccm
時間 90sec
Claims (18)
- 下記一般式(i)で示される部分構造を有するものであり、下記一般式(vi)で示される繰り返し単位を有する高分子化合物であることを特徴とする有機膜形成用化合物。
- 下記一般式(i)で示される部分構造を有するものであり、下記一般式(vii)で示される繰り返し単位を有する高分子化合物であることを特徴とする有機膜形成用化合物。
- 請求項1又は請求項2に記載の有機膜形成用化合物を用いた有機膜材料であって、
(C−3)前記一般式(vi)で示される繰り返し単位を有する高分子化合物、又は(C−4)前記一般式(vii)で示される繰り返し単位を有する高分子化合物のうち、いずれか一つ以上を用いたものであることを特徴とする有機膜材料。 - 更に、前記(C−3)及び(C−4)とは異なる芳香環含有樹脂(D)を含有するものであることを特徴とする請求項3に記載の有機膜材料。
- 前記(D)芳香環含有樹脂が、ナフタレン環を含有するものであることを特徴とする請求項4に記載の有機膜材料。
- 前記(D)芳香環含有樹脂が、下記一般式(3a)及び(3b)で示される化合物のいずれか1種以上と、下記一般式(4)で示される化合物との重縮合物である樹脂(D−1)を含有するものであることを特徴とする請求項4に記載の有機膜材料。
A−CHO (4)
(式中、Aは水素原子、炭素数1〜10の炭化水素基、又は炭素数6〜20の置換又は非置換の芳香族炭化水素基のいずれかである。) - 更に、(E)フェノール性水酸基含有化合物、(F)酸発生剤、(G)架橋剤、(H)界面活性剤、(I)有機溶媒のうち少なくとも1種以上を含有するものであることを特徴とする請求項3から請求項7のいずれか一項に記載の有機膜材料。
- 請求項3から請求項8のいずれか一項に記載の有機膜材料であって、レジスト下層膜材料又は半導体装置製造用平坦化材料として用いられるものであることを特徴とする有機膜材料。
- リソグラフィーで用いられる多層レジスト膜のレジスト下層膜又は半導体製造用平坦化膜として機能する有機膜の形成方法であって、被加工基板上に請求項3から請求項9のいずれか一項に記載の有機膜材料をコーティングし、該材料を100℃以上600℃以下の温度で、10秒〜600秒間の範囲で熱処理することによって硬化膜を形成することを特徴とする有機膜形成方法。
- リソグラフィーで用いられる多層レジスト膜のレジスト下層膜又は半導体製造用平坦化膜として機能する有機膜の形成方法であって、被加工基板上に請求項3から請求項9のいずれか一項に記載の有機膜材料をコーティングし、該材料を、酸素濃度0.1%以上21%以下の雰囲気中で焼成することによって硬化膜を形成することを特徴とする有機膜形成方法。
- 前記被加工基板として、高さ30nm以上の構造体又は段差を有する被加工基板を用いることを特徴とする請求項10又は請求項11に記載の有機膜形成方法。
- 被加工基板にパターンを形成する方法であって、少なくとも、被加工基板上に請求項3から請求項9のいずれか一項に記載の有機膜材料を用いてレジスト下層膜を形成し、該レジスト下層膜上にケイ素原子を含有するレジスト中間層膜材料を用いてレジスト中間層膜を形成し、該レジスト中間層膜上にフォトレジスト組成物からなるレジスト上層膜材料を用いてレジスト上層膜を形成して多層レジスト膜とし、前記レジスト上層膜のパターン回路領域を露光した後、現像液で現像して前記レジスト上層膜にレジストパターンを形成し、該得られたレジストパターンをエッチングマスクにして前記レジスト中間層膜をエッチングし、該得られたレジスト中間層膜パターンをエッチングマスクにして前記レジスト下層膜をエッチングし、更に、該得られたレジスト下層膜パターンをエッチングマスクにして前記被加工基板をエッチングして前記被加工基板にパターンを形成することを特徴とするパターン形成方法。
- 前記レジスト中間層膜をエッチングマスクにして行う前記レジスト下層膜のエッチングを、酸素ガス又は水素ガスを主体とするエッチングガスを用いて行うことを特徴とする請求項13に記載のパターン形成方法。
- 被加工基板にパターンを形成する方法であって、少なくとも、被加工基板上に請求項3から請求項9のいずれか一項に記載の有機膜材料を用いてレジスト下層膜を形成し、該レジスト下層膜上にケイ素酸化膜、ケイ素窒化膜及びケイ素酸化窒化膜から選ばれる無機ハードマスク中間膜を形成し、該無機ハードマスク中間膜上にフォトレジスト組成物からなるレジスト上層膜材料を用いてレジスト上層膜を形成して多層レジスト膜とし、前記レジスト上層膜のパターン回路領域を露光した後、現像液で現像して前記レジスト上層膜にレジストパターンを形成し、該得られたレジストパターンをエッチングマスクにして前記無機ハードマスク中間膜をエッチングし、該得られた無機ハードマスク中間膜パターンをエッチングマスクにして前記レジスト下層膜をエッチングし、更に、該得られたレジスト下層膜パターンをエッチングマスクにして前記被加工基板をエッチングして前記被加工基板にパターンを形成することを特徴とするパターン形成方法。
- 被加工基板にパターンを形成する方法であって、少なくとも、被加工基板上に請求項3から請求項9のいずれか一項に記載の有機膜材料を用いてレジスト下層膜を形成し、該レジスト下層膜上にケイ素酸化膜、ケイ素窒化膜及びケイ素酸化窒化膜から選ばれる無機ハードマスク中間膜を形成し、該無機ハードマスク中間膜上に有機反射防止膜を形成し、該有機反射防止膜上にフォトレジスト組成物からなるレジスト上層膜材料を用いてレジスト上層膜を形成して多層レジスト膜とし、前記レジスト上層膜のパターン回路領域を露光した後、現像液で現像して前記レジスト上層膜にレジストパターンを形成し、該得られたレジストパターンをエッチングマスクにして前記有機反射防止膜と前記無機ハードマスク中間膜をエッチングし、該得られた無機ハードマスク中間膜パターンをエッチングマスクにして前記レジスト下層膜をエッチングし、更に、該得られたレジスト下層膜パターンをエッチングマスクにして前記被加工基板をエッチングして前記被加工基板にパターンを形成することを特徴とするパターン形成方法。
- 前記無機ハードマスク中間膜が、CVD法又はALD法によって形成されることを特徴とする請求項15又は請求項16に記載のパターン形成方法。
- 前記被加工基板として高さ30nm以上の構造体又は段差を有する被加工基板を用いることを特徴とする請求項13から請求項17のいずれか一項に記載のパターン形成方法。
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US20160018735A1 (en) | 2016-01-21 |
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