JP2021167949A - 着色樹脂組成物、着色膜、カラーフィルターおよび液晶表示装置 - Google Patents
着色樹脂組成物、着色膜、カラーフィルターおよび液晶表示装置 Download PDFInfo
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Abstract
フォトリソグラフィに一般的に用いられる紫外領域(波長365nm)における光透過性と、可視領域における遮光性を向上させ、高感度の着色樹脂組成物を提供する。
【解決手段】
(A)アルカリ可溶性樹脂、(B)着色材、(C)有機溶剤および(D)感光剤を含有する着色樹脂組成物であって、前記(B)着色材として少なくともジルコニア化合物粒子を含有し、前記ジルコニア化合物粒子に含まれる窒化ジルコニウムの、CuKα線をX線源としたときのX線回折スペクトルにおける(111)面に由来するピークの半値幅より求めた結晶子サイズが10nm以上60nm以下である着色樹脂組成物。
【選択図】なし
Description
「金属光沢をもち,電気と熱をよく導き,固体状態では展性,延性に富む物質.水銀以外は室温ですべて固体である.ふつう種々の機械的加工を施すことができる.液化しても光学的・電気的性質は保たれることが多い.単体の金属結晶の大部分は面心立方,六方最密,体心立方のいずれかの構造をとり,通常は微結晶の集合体をなす.結晶中の原子は*金属結合によって結ばれ,電子の一部は自由電子として存在する.金属の性質は金属結合に由来する.単体アンチモン,ビスマスなど自由電子の数が少ない金属を*半金属とよぶ.単体に限らず2種以上の金属元素,または金属元素とある種の非金属元素(ホウ素,炭素など)を含む相にも金属性を示すものがある.なお,金属の電気伝導は温度の上昇とともに減少するが,非金属では増加するので,このことから両者を明確に区別することができる.」
金属としては特に限定されず、好ましい例としては、チタン、アルミニウム、銅、銀、金、白金、パラジウム、ニッケル、錫、コバルト、ロジウム、イリジウム、鉄、ルテニウム、オスミウム、マンガン、モリブデン、タングステン、ニオブ、タンタル、カルシウム、チタン、ビスマス、アンチモン、鉛、またはこれらの合金、から選ばれる少なくとも一種を挙げることができる。さらに好ましい金属としてはチタン、アルミニウムが挙げられる。
OD値 = log10(I0/I) ・・・ 式(5)
I0:入射光強度
I:透過光強度。
[窒化ジルコニウムの結晶子サイズおよびピーク強度比ZrO2/ZrN]
製造例に用いたジルコニウム化合物粒子Zr−1〜Zr−6をアルミ製標準試料ホルダーに詰め、(株)理学製RU−200Rを用いて、X線源をCuKα1線として、広角X線回折法によりX線回折スペクトルを測定した。測定条件としては、出力は50kV/200mA、スリット系は1°−1°−0.15mm−0.45mm、測定ステップ(2θ)は0.02°、スキャン速度は2°/分とした。
製造例に用いたジルコニウム化合物粒子Zr−1〜Zr−6について、日本ベル(株)製高精度全自動ガス吸着装置“BELSORP”36を用いて、100℃で真空脱気後、N2ガスの液体窒素温度(77K)における吸着等温線を測定し、この等温線をBET法で解析し比表面積を求めた。結果を表1に示す。
ジルコニウム化合物粒子Zr−4〜Zr−6について、アルカリで溶融分解後、溶融物を塩酸で溶解し、超純水で定容して検液とした。ICP−AES(エスアイアイ・ナノテクノロジー(株)製、SPS5100型) により、検液中の元素の定量分析を行った結果を表1に示す。
各実施例および比較例により得られた着色膜について、X−Rite社製光学濃度計361TVisualを用いて、膜厚1μmあたりのOD値を算出した。
各実施例および比較例により得られた着色膜について、(株)島津製作所製紫外−可視分光光度計UV−2600を用いて、OD値が1.0となる膜厚における、波長365nmおよび550nmにおける透過率を測定した。波長365nmにおける透過率が高いほど、紫外領域における光透過性に優れる。また、波長550nmにおける光透過率に対する波長365nmにおける光透過率の比を算出した。
各実施例および比較例により得られた着色膜について、接触式膜厚計(“DEKTAK”(登録商標)150;アルバック社販売)を用いて、触針圧5mgでの表面粗度(nm)を測定した。
各実施例および比較例により得られた着色膜に、フォトマスクを介して、紫外線を200mJ/cm2を最大露光量として、10mJ/cm2ごとに露光量を下げて露光し、0.045重量%水酸化カリウム水溶液のアルカリ現像液でシャワー現像した後のパターン表面の荒れの有無を目視にて観察した。現像後のパターン表面に荒れが生じない最低露光量を感度とした。ただし、最大露光量においても現像後にパターンが残存していない場合は「欠落」とした。
各実施例および比較例により得られた着色膜に、パターン幅の異なる、ライン・アンド・スペースパターンが1対1の間隔で配置されたフォトマスクを介して、紫外線を200mJ/cm2露光し、所定のアルカリ現像液でシャワー現像した後に、パターンを顕微鏡にて観察した。現像後のパターンが解像している最小の線幅を最小解像度とした。
各実施例および比較例により得られた着色膜に、線幅20μm、間隔1対1のライン・アンド・スペースパターンが配置されたフォトマスクを介して200mJ/cm2を最大露光量として、10mJ/cm2ごとに露光量を下げて露光し、所定のアルカリ現像液でシャワー現像した後に、パターンおよびスペースの線幅を顕微鏡にて観察した。ライン・アンド・スペースパターンを1対1で形勢できる最低露光量を感度とした。ただし、最大露光量においても現像後にスペースパターン部に未溶解物が残存している場合は「残渣」とした。
各実施例および比較例により得られた遮光パターンについて、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、「PGMEA」と記載する)に浸した不織布で15秒間表面をふき取った後のOD値を、前述の[遮光性]と同様に測定した。ふき取り後のOD値がふき取り前のOD値(4.0)に近いほど、耐溶剤性に優れる。
特許第3120476号明細書の実施例1に記載の方法により、メチルメタクリレート/メタクリル酸/スチレン共重合体(重量比30/40/30)を合成した。得られた共重合体100重量部に対し、グリシジルメタクリレート40重量部を付加させ、精製水で再沈し、濾過および乾燥することにより、重量平均分子量15,000、酸価110mgKOH/gのアルカリ可溶性のアクリル樹脂(P−1)を得た。
2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(セントラル硝子(株)製)18.3g(0.05モル)をアセトン100mL、プロピレンオキシド(東京化成(株)製)17.4g(0.3モル)に溶解させ、−15℃に冷却した。ここに3−ニトロベンゾイルクロリド(東京化成(株)製)20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、−15℃で4時間撹拌し、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)、21.22g(0.05モル)と5−ナフトキノンジアジドスルホン酸クロリド(東洋合成(株)製、NAC−5)26.8g(0.1モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合したトリエチルアミン12.65gを、系内が35℃以上にならないように滴下した。滴下後40℃で2時間撹拌した。トリエチルアミン塩を濾過し、濾液を水に投入した。その後、析出した沈殿を濾過で集め、さらに1%塩酸水1Lで洗浄した。その後、さらに水2Lで2回洗浄した。この沈殿を真空乾燥機で乾燥し、下記式(7)で表されるキノンジアジド化合物(b−1)を得た。
着色材として、熱プラズマ法により製造したジルコニア化合物粒子Zr−1(日清エンジニアリング(株)製)を用いた。Zr−1 200g、アクリルポリマー(P−1)の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)35重量%溶液114g、高分子分散剤として3級アミノ基と4級アンモニウム塩を有する“DISPERBYK”(登録商標)LPN−2111625gおよびPGMEA661gをタンクに仕込み、ホモミキサーで20分撹拌し、予備分散液を得た。0.05mmφジルコニアビーズを75体積%充填した遠心分離セパレーターを具備した寿工業(株)製分散機ウルトラアペックスミルに、得られた予備分散液を供給し、回転速度8m/sで3時間分散を行い、固形分濃度25重量%、着色材/樹脂(重量比)=80/20の着色材分散液DC−1を得た。
着色材として、特開2009−91205に記載の方法により製造されたジルコニウム化合物粒子Zr−2を用いた以外は製造例1と同様にして、着色材分散液(DC−2)を得た。
着色材として、熱プラズマ法により製造した窒化ジルコニウムとアルミニウム粒子からなる複合微粒子であるジルコニア化合物粒子Zr−4(アルミ含有量=4wt%、BET表面積=29.0m2/g)を用いた以外は製造例1と同様にして、着色材分散液(DC−3)を得た。
着色材として、熱プラズマ法により製造した窒化ジルコニウムとアルミニウム粒子からなる複合微粒子であるジルコニア化合物粒子Zr−5(アルミ含有量=4wt%、BET表面積=58.5m2/g)を用いた以外は製造例1と同様にして、着色材分散液(DC−4)を得た。
着色材として、熱プラズマ法により製造した窒化ジルコニウムとアルミニウム粒子からなる複合微粒子であるジルコニア化合物粒子Zr−6(アルミ含有量=8wt%、BET表面積=23.0m2/g)を用いた以外は製造例1と同様にして、着色材分散液(DC−5)を得た。
熱プラズマ法により製造したジルコニア化合物粒子Zr−1(日清エンジニアリング(株)製)200g、ポリアミドエステル樹脂(P−3)の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)35重量%溶液114g、高分子分散剤としてアミド基を有する“DISPERBYK”(登録商標)−2200gおよびPGMEA661gをタンクに仕込み、ホモミキサーで20分撹拌し、予備分散液を得た。0.05mmφジルコニアビーズを75体積%充填した遠心分離セパレーターを具備した寿工業(株)製分散機ウルトラアペックスミルに、得られた予備分散液を供給し、回転速度8m/sで3時間分散を行い、固形分濃度25重量%、着色材/樹脂(重量比)=80/20の着色材分散液DC−6を得た。
着色材として、熱プラズマ法により製造した窒化ジルコニウムとアルミニウム粒子からなる複合微粒子であるジルコニア化合物粒子Zr−4(アルミ含有量=4wt%、BET表面積=29.0m2/g)を用いた以外は製造例6と同様にして、着色材分散液(DC−7)を得た。
着色材として有機紫顔料PV23(クラリアント社製)を用いた以外は製造例1と同様にして、着色材分散液(DC−8)を得た。
着色材として市販の窒化ジルコニウム粒子Zr−3(日本新金属(株)製)を用いた以外は製造例1と同様にして、着色材分散液(DC−9)を得た。
着色材としてチタン窒化物粒子(日清エンジニアリング(株)製)を用いた以外は製造例1と同様にして、着色材分散液(DC−10)を得た。
着色材としてスルホン酸基により表面が修飾されたカーボンブラック(キャボット製TPK1227)を用いた以外は製造例1と同様にして、着色材分散液(DC−11)を得た。
着色材としてスルホン酸基により表面が修飾されたカーボンブラック(キャボット製TPK1227)を用いた以外は製造例6と同様にして、着色材分散液(DC−12)を得た。
283.1gの着色材分散液(DC−1)に、アクリルポリマー(P−1)のPGMEA35重量%溶液を184.4g、多官能モノマーとしてジペンタエリスリトールヘキサアクリレート(日本化薬(株)製)を50.1g、光重合開始剤として“Irgacure”(登録商標)907(BASF社製)を7.5gおよび“KAYACURE”(登録商標)DETX−S”(日本化薬(株)製)を3.8g、密着改良剤としてKBM5103(信越化学(株)製)を12.0g、界面活性剤としてシリコーン系界面活性剤“BYK”(登録商標)333(ビックケミー社製)のPGMEA10重量%溶液3gを456.1gのPGMEAに溶解した溶液を添加して、全固形分濃度20重量%、着色材/樹脂(重量比)=30/70のネガ型感光性着色樹脂組成物PC−1を得た。
着色材分散液(DC−1)の代わりに着色材分散液(DC−2)を用いた以外は実施例1と同様にして、ネガ型感光性着色樹脂組成物PC−2を得た。得られた着色樹脂組成物PC−2を用いて、実施例1と同様の評価をした。結果を表2に示す。
187.0gの着色材分散液(DC−1)に、アクリルポリマー(P−1)のPGMEA35重量%溶液を226.8g、多官能モノマーとしてジペンタエリスリトールヘキサアクリレート(日本化薬(株)製)を57.6g、光重合開始剤として“Irgacure”(登録商標)907(BASF社製)を8.6gおよび“KAYACURE”(登録商標)DETXを4.3g、密着改良剤としてKBM5103(信越化学(株)製)を12.0g、界面活性剤としてシリコーン系界面活性剤“BYK”(登録商標)333(ビックケミー社製)の10重量%PGMEA溶液3gを500.7gのPGMEAに溶解した溶液を添加して、全固形分濃度20重量%、着色材/樹脂(重量比)=20/80のネガ型感光性着色樹脂組成物PC−3を得た。得られた着色樹脂組成物PC−3を用いて、実施例1と同様の評価をした。結果を表2に示す。
380.9gの着色材分散液(DC−1)に、アクリルポリマー(P−1)のPGMEA35重量%溶液を141.2g、多官能モノマーとしてジペンタエリスリトールヘキサアクリレート(日本化薬(株)製)を42.5g、光重合開始剤として“Irgacure”(登録商標)907(BASF社製)を6.4gおよび“KAYACURE”(登録商標)DETXを3.2g、密着改良剤としてKBM5103(信越化学(株)製)を12.0g、界面活性剤としてシリコーン系界面活性剤“BYK”(登録商標)333(ビックケミー社製)10重量%PGMEA溶液3gを410.8gのPGMEAに溶解した溶液を添加して、全固形分濃度20重量%、着色材/樹脂(重量比)=40/60のネガ型感光性着色樹脂組成物PC−4を得た。得られた着色樹脂組成物PC−4を用いて、実施例1と同様の評価をした。結果を表2に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−3)を用いた以外は実施例1と同様にして、ネガ型感光性着色樹脂組成物PC−5を得た。得られた着色樹脂組成物PC−5を用いて、実施例1と同様の評価をした。結果を表2に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−4)を用いた以外は実施例1と同様にして、ネガ型感光性着色樹脂組成物PC−6を得た。得られた着色樹脂組成物PC−6を用いて、実施例1と同様の評価をした。結果を表2に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−5)を用いた以外は実施例1と同様にして、ネガ型感光性着色樹脂組成物PC−7を得た。得られた着色樹脂組成物PC−7を用いて、実施例1と同様の評価をした。結果を表2に示す。
着色材分散液として、212.3gの着色材分散液(DC−1)および70.8gの着色材分散液(DC−8)の混合液を用いた以外は実施例1と同様にしてネガ型感光性着色樹脂組成物PC−8を得た。得られた着色樹脂組成物PC−8を用いて、実施例1と同様の評価をした。結果を表2に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−9)を用いた以外は実施例1と同様にして、ネガ型感光性着色樹脂組成物PC−9を得た。得られた着色樹脂組成物PC−9を用いて、実施例1と同様の評価をした。結果を表2に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−10)を用いた以外は実施例1と同様にして、ネガ型感光性着色樹脂組成物PC−10を得た。得られた着色樹脂組成物PC−10を用いて、実施例1と同様の評価をした。結果を表2に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−11)を用いた以外は実施例1と同様にして、ネガ型感光性着色樹脂組成物PC−11を得た。得られた着色樹脂組成物PC−11を用いて、実施例1と同様の評価をした。結果を表2に示す。
128.9gの着色材分散液(DC−1)に、アクリルポリマー(P−1)のPGMEA35重量%溶液を273.6g、多官能モノマーとしてジペンタエリスリトールヘキサアクリレート(日本化薬(株)製)を67.1g、光重合開始剤として“アデカアークルズ”(登録商標)NCI−831(ADEKA社製)を1.7g、密着改良剤としてKBM5103(信越化学(株)製)を3.0g、界面活性剤としてシリコーン系界面活性剤“BYK”(登録商標)333(ビックケミー社製)のPGMEA10重量%溶液3gを522.8gのPGMEAに溶解した溶液を添加して、全固形分濃度20重量%、着色材/樹脂(重量比)=13/87のネガ型感光性着色樹脂組成物PC−12を得た。
アクリルポリマー(P−1)のPGMEA35重量%溶液273.6gの代わりにカルド樹脂V−259ME(新日鉄住金(株)製、PGMEA45重量%溶液)(P−2)212.8gを用いた以外は実施例9と同様にして、ネガ型感光性着色樹脂組成物PC−13を得た。得られた着色樹脂組成物PC−13を用いて、実施例9と同様の評価をした。結果を表3に示す。
49.5gの着色材分散液(DC−1)に、カルド樹脂V−259ME(新日鉄住金(株)製、PGMEA45重量%溶液)(P−2)241.7g、多官能モノマーとしてジペンタエリスリトールヘキサアクリレート(日本化薬(株)製)を73.7g、光重合開始剤として“アデカアークルズ”(登録商標)NCI−831(ADEKA社製)を1.8g、密着改良剤としてKBM5103(信越化学(株)製)を3.0g、界面活性剤としてシリコーン系界面活性剤“BYK”(登録商標)333(ビックケミー社製)のPGMEA10重量%溶液3gを627.3gのPGMEAに溶解した溶液を添加して、全固形分濃度20重量%、着色材/樹脂(重量比)=5/95のネガ型感光性着色樹脂組成物PC−14を得た。得られた着色樹脂組成物PC−14を用いて、実施例9と同様の評価をした。結果を表3に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−3)を用いた以外は実施例10と同様にして、ネガ型感光性着色樹脂組成物PC−15を得た。得られた着色樹脂組成物PC−15を用いて、実施例9と同様の評価をした。結果を表3に示す。
着色材分散液(DC−1)の代わりに着色材分散液(DC−11)を用いた以外は実施例10と同様にして、ネガ型感光性着色樹脂組成物PC−16を得た。得られた着色樹脂組成物PC−16を用いて、実施例9と同様の評価をした。結果を表3に示す。
170.0gの着色材分散液(DC−6)に、ポリアミドエステル樹脂(P−3)97.2gに合成例3で得られたキノンジアジド化合物(b−1)28.6g、フェノール化合物ビスフェノール−AF(東京化成工業(株)製)28.6g、シリコーン系界面活性剤“BYK”(登録商標)333(ビックケミー社製)のPGMEA10重量%溶液3gを645.5gのPGMEAに溶解した溶液を添加して、全固形分濃度20重量%、着色材/樹脂(重量比)=17/83のポジ型感光性着色樹脂組成物PC−17を得た。
着色材分散液(DC−6)の代わりに着色材分散液(DC−7)を用いた以外は実施例13と同様にして、ポジ型感光性着色樹脂組成物PC−18を得た。得られた着色樹脂組成物PC−18を用いて、実施例13と同様の評価をした。結果を表4に示す。
着色材分散液(DC−6)の代わりに着色材分散液(DC−12)を用いた以外は実施例13と同様にして、ポジ型感光性着色樹脂組成物PC−19を得た。得られた着色樹脂組成物PC−19を用いて、実施例13と同様の評価をした。結果を表4に示す。
実施例1にて作成した着色膜C−1について、耐溶剤性の結果を表5に示す。
着色膜C−1について、ポストベイクの条件を230℃×30分から100℃×60分に変えた以外は実施例1と同様にして、着色膜C−20を得た。得られた着色膜C−20について、参考例1と同様の評価をした。結果を表5に示す。
着色膜C−1について、現像後のパターンに対して、i線露光量が500mJ/cm2となるよう、浜松ホトニクス(株)製LEDランプ(GC−77)を用いて、出力50%、照射距離3cmの条件で、無アルカリガラスを介して1.66秒間露光した以外は参考例2)と同様にして、着色膜C−21を得た。得られた着色膜C−21について、参考例1と同様の評価をした。結果を表5に示す。
着色樹脂組成物(PC−1)の代わりに着色樹脂組成物(PC−9)を用いた以外は実施例16と同様にして、着色膜C−22を得た。得られた着色膜C−22を用いて、参考例1と同様の評価をした。結果を表5に示す。
着色樹脂組成物(PC−1)の代わりに着色樹脂組成物(PC−10)を用いた以外は実施例16と同様にして、着色膜C−23を得た。得られた着色膜C−23について、参考例1と同様の評価をした。結果を表5に示す。
着色樹脂組成物(PC−1)の代わりに着色樹脂組成物(PC−11)を用いた以外は実施例16と同様にして、着色膜C−24を得た。得られた着色膜C−24について、参考例1と同様の評価をした。結果を表5に示す。
Claims (15)
- (A)アルカリ可溶性樹脂、(B)着色材、(C)有機溶剤および(D)感光剤を含有する着色樹脂組成物であって、前記(B)着色材として少なくともジルコニア化合物粒子を含有し、前記ジルコニア化合物粒子に含まれる窒化ジルコニウムの、CuKα線をX線源としたときのX線回折スペクトルにおける(111)面に由来するピークの半値幅より求めた結晶子サイズが10nm以上60nm以下である着色樹脂組成物。
- 前記ジルコニア化合物粒子が、窒化ジルコニウムと金属粒子からなる複合微粒子を含む請求項1記載の着色樹脂組成物。
- 前記ジルコニア化合物粒子が、前記ジルコニア化合物粒子の比表面積が20.0m2/gよりも大きい請求項1または2に記載の着色樹脂組成物
- 前記ジルコニア化合物粒子が、熱プラズマ法により製造された請求項1〜3のいずれか1項に記載の着色樹脂組成物
- 前記(B)着色材として紫着色材をさらに含有する請求項1〜4のいずれか1項記載の着色樹脂組成物。
- 光学濃度(OD値)が1となるように着色膜を形成したときの、前記着色膜の波長365nmにおける光透過率が20%以上となる請求項1〜5のいずれか1項に記載の着色樹脂組成物。
- 前記(D)感光剤として光重合開始剤を含有し、(E)ラジカル重合性化合物をさらに含有する請求項1〜6のいずれか1項に記載の着色樹脂組成物。
- 前記(D)感光剤として光酸発生剤を含有する請求項1〜6のいずれか1項に記載の着色樹脂組成物。
- 請求項1〜8のいずれか一項記載の着色樹脂組成物の硬化物からなる、着色膜。
- 透明基板上に請求項1〜8のいずれか1項記載の着色樹脂組成物を塗布して塗布膜を得る工程、得られた塗布膜を乾燥して乾燥膜を得る工程、得られた乾燥膜を露光および現像することにより所望の形状にパターニングする工程、および、得られたパターンを、前記透明基板を介して露光する工程を有する遮光パターン付き基板の製造方法。
- 請求項9記載の着色膜を具備する、カラーフィルター。
- 請求項11記載のカラーフィルターを具備する、液晶表示装置。
- 請求項9記載の着色膜からなる着色隔壁。
- 請求項13記載の着色隔壁を具備する、固体撮像素子。
- 請求項13記載の着色隔壁間に色変換材料を有する表示装置。
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JP2019112275A (ja) * | 2017-12-26 | 2019-07-11 | 三菱マテリアル電子化成株式会社 | 黒色遮光膜形成用粉末及びその製造方法 |
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KR20200055708A (ko) | 2020-05-21 |
TWI757548B (zh) | 2022-03-11 |
WO2019059359A1 (ja) | 2019-03-28 |
JPWO2019059359A1 (ja) | 2020-09-03 |
TW201920000A (zh) | 2019-06-01 |
US11634555B2 (en) | 2023-04-25 |
KR102548102B1 (ko) | 2023-06-28 |
US20210115219A1 (en) | 2021-04-22 |
CN111095044B (zh) | 2022-08-12 |
CN111095044A (zh) | 2020-05-01 |
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