JPWO2016072316A1 - アリーレン基を有するポリマーを含むレジスト下層膜形成組成物 - Google Patents
アリーレン基を有するポリマーを含むレジスト下層膜形成組成物 Download PDFInfo
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- JPWO2016072316A1 JPWO2016072316A1 JP2016557719A JP2016557719A JPWO2016072316A1 JP WO2016072316 A1 JPWO2016072316 A1 JP WO2016072316A1 JP 2016557719 A JP2016557719 A JP 2016557719A JP 2016557719 A JP2016557719 A JP 2016557719A JP WO2016072316 A1 JPWO2016072316 A1 JP WO2016072316A1
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Classifications
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
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- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—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
- 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
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—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
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Abstract
Description
さらに、ポリマーの主鎖中に3つ又はそれ以上縮合した芳香族環を有するポリマーを含む、スピンコート可能な反射防止膜組成物が開示されている(特許文献2)。
また、フェニルナフチルアミンを用いたノボラック樹脂が用いられている(特許文献3)。
この様なポリマーを分散剤として使用することも提案されている(特許文献4)。
(式(1)中、R1乃至R4はそれぞれ独立に水素原子又はメチル基を示す。X1はアルキル基、アミノ基、又はヒドロキシル基で置換されていても良い少なくとも一つのアリーレン基を含む二価の有機基を示す。)で表される単位構造を含むポリマーと溶剤とを含むレジスト下層膜形成組成物、
第2観点として、式(1)中、X1の定義におけるアリーレン基がフェニレン基、ビフェニレン基、ターフェニレン基、フルオレニレン基、ナフチレン基、アントリレン基、ピレニレン基、又はカルバゾリレン基である第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、式(1)中、X1が式(2):
〔式(2)中、A1はフェニレン基又はナフチレン基を表す。A2はフェニレン基、ナフチレン基、又は式(3):
(式(3)中、A3及びA4はそれぞれ独立にフェニレン基又はナフチレン基を表す。点線は結合を表す。)で示される有機基を表す。点線は結合を表す。〕で表される有機基である第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、更に架橋剤を含む第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、更に酸及び/又は酸発生剤を含む第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、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7観点として、半導体基板上に第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から下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンにより該下層膜をエッチングする工程、及びパターン化された下層膜により該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8観点として、半導体基板上に第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から下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該下層膜をエッチングする工程、及びパターン化された下層膜により該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。
そして、架橋剤と酸を含むことができ、必要に応じて酸発生剤、界面活性剤等の添加剤を含むことができる。この組成物の固形分は0.1乃至70質量%、又は0.1乃至60質量%、又は0.2乃至30質量%、又は0.3乃至15質量%である。ここで、固形分はレジスト下層膜形成組成物から溶剤を除いた全成分の含有割合である。固形分中に上記ポリマーを1乃至100質量%、または1乃至99.9質量%、または50乃至99.9質量%、または50乃至95質量%、または50乃至90質量%の割合で含有することができる。
本発明に用いられるポリマーは、重量平均分子量が600乃至1000000、又は600乃至200000、又は1500乃至15000である。
式(2)中、A1はフェニレン基又はナフチレン基を表す。A2はフェニレン基、ナフチレン基、又は式(3)で示される有機基を表す。なお、式(2)中、点線は結合を表す。
式(3)中、A3及びA4はそれぞれ独立にフェニレン基又はナフチレン基を表す。なお、式(3)中、点線は結合を表す。
上記架橋剤としては耐熱性の高い架橋剤を用いることができる。耐熱性の高い架橋剤としては分子内に芳香族環(例えば、ベンゼン環、ナフタレン環)を有する架橋形成置換基を含有する化合物を好ましく用いることができる。
上記式中、R11、R12、R13、及びR14はそれぞれ独立に水素原子又は炭素数1乃至10のアルキル基を表し、これらのアルキル基は上述の例示を用いることができる。また、n1は1乃至2の整数を表し、n2は1乃至(6−n1)の整数を表し、n3は1乃至2の整数を表し及びn4は0乃至(4−n3)の整数を表す。
GPCカラム:TSKgel SuperMultipore〔登録商標〕Hz−N(東ソー(株))
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
流量:0.35ml/分
標準試料:ポリスチレン(東ソー(株))
窒素下、300mL四口フラスコにα,α’−ジヒドロキシ−1,3−ジイソプロピルベンゼン(28.79g、0.148mol、東京化成工業(株)製)、N−フェニル−1−ナフチルアミン(30.00g、0.1368mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(5.68g、0.029mol、東京化成工業(株)製)を加え、さら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(以下本明細書ではPGMEAという略称で示すこともある。)(150.43g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。16時間後60℃まで放冷後、メタノール(1600g、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60℃、16時間乾燥させ、式(1−1)で表される構造単位を有する目的とするポリマー(38.6g)を得た。得られたポリマーの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は2000であった。
窒素下、500mL四口フラスコにα,α’−ジヒドロキシ−1,3−ジイソプロピルベンゼン(37.33g、0.1921mol東京化成工業(株)製)、N,N’−ジフェニル−1,4−フェニレンジアミン(50.00g、0.1921mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.53g、0.008mol、東京化成工業(株)製)を加え、さら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(PGMEA)207.33g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。16時間後60℃まで放冷後、メタノール(1600g、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50℃、16時間乾燥させ、式(1−2)で表される構造単位を有する目的とするポリマー(56.04g)を得た。得られたポリマーの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は2700であった。
窒素下、100mL四口フラスコにα,α’−ジヒドロキシ−1,3−ジイソプロピルベンゼン(3.23g、0.017mol、東京化成工業(株)製)、N,N’−ジ−2−ナフチル−1,4−フェニレンジアミン(6.00g、0.017mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.50g、0.003mol、東京化成工業(株)製)を加え、さら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(PGMEA)22.70g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。16時間後60℃まで放冷後、メタノール(800g、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60℃、16時間乾燥させ、式(1−3)で表される構造単位を有する目的とするポリマー(5.8g)を得た。得られたポリマーの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は1700であった。
窒素下、200mL四口フラスコにα,α’−ジヒドロキシ−1,3−ジイソプロピルベンゼン(5.97g、0.031mol、東京化成工業(株)製)、N−フェニル−1−ナフチルアミン(3.37g、0.015mol、東京化成工業(株)製)、N,N’−ジフェニル−1,4−フェニレンジアミン(4.00g、0.015mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.25g、0.001mol、東京化成工業(株)製)を加え、さら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(PGMEA)31.70g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。16時間後60℃まで放冷後、メタノール(1000g、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60℃、16時間乾燥させ、式(1−4)で表される構造単位を有する目的とするポリマー(7.1g)を得た。得られたポリマーの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は2800であった。
窒素下、100mL四口フラスコにα,α’−ジヒドロキシ−1,3−ジイソプロピルベンゼン(6.65g、0.034mol、東京化成工業(株)製)、N−フェニル−1−ナフチルアミン(3.68g、0.017mol、東京化成工業(株)製)、2,2−ビフェノール(3.00g、0.016mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.34g、0.007mol、東京化成工業(株)製)を加え、さら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(PGMEA)34.23g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。16時間後60℃まで放冷後、メタノール(1000g、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60℃、16時間乾燥させ、式(1−5)で表される構造単位を有する目的とするポリマー(7.1g)を得た。得られたポリマーの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は2800であった。
窒素下、100mL四口フラスコに1,4−ビス(メトキシメチル)ベンゼン(5.00g、0.030mol、東京化成工業(株)製)、N−フェニル−1−ナフチルアミン(3.23g、0.015mol、東京化成工業(株)製)、1−ナフトール(2.04g、0.014mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.18g、0.006mol、東京化成工業(株)製)を加え、さら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(PGMEA)26.71g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。16時間後60℃まで放冷後、メタノール(1000g、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60℃、16時間乾燥させ、式(1−6)で表される構造単位を有する目的とするポリマー(7.6g)を得た。得られたポリマーの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は2000であった。
窒素下、500mL四口フラスコに3−ヒドロキシジフェニルアミン(5.00g、0.324mol、東京化成工業(株)製)、1,4−ベンゼンジメタノール(44.76g、0.324mol、東京化成工業(株)製)、メタンスルホン酸(6.23g、0.065mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(以下本明細書ではPGMEという略称で示すこともある。)(206.11g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。17時間後60℃まで放冷後、メタノール(3200g、関東化学(株)製)純水(800g)の混合溶媒へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、16時間乾燥させ、式(1−7)で表される構造単位を有する目的とするポリマー(62.9g)を得た。得られたポリマーの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は3300であった。
窒素下、200mL四口フラスコに2,2−ビフェノール(5.00g、0.027mol、東京化成工業(株)製)、α,α’−ジヒドロキシ−1,3−ジイソプロピルベンゼン(5.97g、0.031mol東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.09g、0.006mol、東京化成工業(株)製)を加え、さら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(PGMEA)26.88g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。16時間後60℃まで放冷後、水/メタノール=1/1(1000g、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60℃、16時間乾燥させ、式(1−8)で表される構造単位を有する目的とするポリマー(7.6g)を得た。得られたポリマーの、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は3400であった。
窒素下、100mL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、さらに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時間乾燥させ、下記式(7−1)で表される構造単位を有する目的とするポリマー(9.37g)を得た。得られたポリマーの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は2800であった。
合成例1で得たポリマー2.0gに、架橋剤として商品名TMOM−BP(本州化学工業(株)製、式(6−23))0.4g、触媒としてピリジニウムパラトルエンスルホン酸0.05g、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.003gを混合し、PGMEA(プロピレングリコールモノメチルエーテルアセテート)16.71gとPGME(プロピレングリコールモノメチルエーテル)4.18g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例2で得たポリマー2.0gに、架橋剤として商品名TMOM−BP(本州化学工業(株)製)0.4g、触媒としてピリジニウムフェノールスルホン酸0.06g、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.004gを混合し、PGMEA14.70gとPGME4.44gとシクロヘキサノン4.44g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例3で得たポリマー2.0gに、架橋剤として商品名TMOM−BP(本州化学工業(株)製)0.4g、触媒としてピリジニウムフェノールスルホン酸0.06g、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.004gを混合し、PGMEA13.31gとPGME4.44gとシクロヘキサノン4.44g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例4で得たポリマー2.0gに、架橋剤として商品名TMOM−BP(本州化学工業(株)製)0.4g、触媒としてピリジニウムフェノールスルホン酸0.06g、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.004gを混合し、PGMEA15.52gとPGME6.65g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例5で得たポリマー2.0gに、架橋剤として商品名TMOM−BP(本州化学工業(株)製)0.4g、触媒としてピリジニウムフェノールスルホン酸0.06g、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.004gを混合し、PGMEA15.52gとPGME6.65g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例6で得たポリマー2.0gに、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.004gを混合し、PGMEA12.63gとPGME5.41g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例7で得たポリマー2.0gに、架橋剤として商品名TMOM−BP(本州化学工業(株)製)0.3g、触媒としてピリジニウムフェノールスルホン酸0.03g、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.004gを混合し、PGMEA12.60gとPGME8.40g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例8で得たポリマー2.0gに、架橋剤として商品名TMOM−BP(本州化学工業(株)製)0.4g、触媒としてピリジニウムフェノールスルホン酸0.06g、界面活性剤として商品名メガファックR−40LM(DIC(株)製)0.004gを混合し、PGMEA15.52gとPGME6.65g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
比較合成例1で得たポリマー20gに、架橋剤としてテトラメトキシメチルグリコリールウリル3.0g、触媒としてピリジニウムパラトルエンスルホン酸0.02g、界面活性剤として商品名メガファックR−40(DIC(株)製)0.006gを混合し、PGMEA16.71gとPGME4.18g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ろ過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
実施例1乃至実施例8と比較例1で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハ上に塗布した。ホットプレート上で400℃90秒間ベークし、レジスト下層膜(膜厚0.2μm)を形成した。これらのレジスト下層膜をシリコンウェハから削り取り、粉末体を得た。得られた粉末体の400℃での熱重量現象をTG/DTA(BRUKER社製 TG−DTA2010SR)にて測定した。その結果を表1に示す。
材料の平坦化性と埋め込み性を評価するために次の様なウェハをArF露光機とドライエッチングを用いて作成した。ホール径75nm、ホール深さ500nm、ホールとホールのスペースが105nmとなるパターンをTEOSウェハに作成した。そのTEOSウェハ上に実施例1乃至実施例8及び比較例1で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いて塗布した。それらをホットプレート上で400℃90秒間ベークし、レジスト下層膜(膜厚220nm)を形成した。次いで電子顕微鏡にてウェハの断面を観察して、ホール密集地エリアのTEOS表面上のレジスト下層膜の膜厚を測定した。また、パターンエリアの横に位置するフラットなエリアの膜厚も測定した。得られた測定値に基づいて以下の計算式により平坦化性を数値化した。
平坦化性(%)={(フラットエリアの膜厚)−(ホールエリアの膜厚)}/(フラットエリアの膜厚)×100
この平坦化性が20%以下であるものを良好とし、それ以上を不良とした。測定結果を表2に示す。
Claims (8)
- 式(1)中、X1の定義におけるアリーレン基がフェニレン基、ビフェニレン基、ターフェニレン基、フルオレニレン基、ナフチレン基、アントリレン基、ピレニレン基、又はカルバゾリレン基である請求項1に記載のレジスト下層膜形成組成物。
- 更に架橋剤を含む請求項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。
- 更に酸及び/又は酸発生剤を含む請求項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。
- 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。
- 半導体基板上に請求項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から下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンにより該下層膜をエッチングする工程、及びパターン化された下層膜により該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から下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該下層膜をエッチングする工程、及びパターン化された下層膜により該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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CN107077071B (zh) | 2020-10-02 |
CN107077071A (zh) | 2017-08-18 |
US20170315445A1 (en) | 2017-11-02 |
KR102454445B1 (ko) | 2022-10-14 |
TW201631400A (zh) | 2016-09-01 |
JP6652747B2 (ja) | 2020-02-26 |
SG11201703411TA (en) | 2017-05-30 |
TWI687771B (zh) | 2020-03-11 |
WO2016072316A1 (ja) | 2016-05-12 |
KR20170081166A (ko) | 2017-07-11 |
US10394124B2 (en) | 2019-08-27 |
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