TWI653254B - 聚合物、有機層組成物以及形成圖案的方法 - Google Patents
聚合物、有機層組成物以及形成圖案的方法 Download PDFInfo
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- TWI653254B TWI653254B TW105130943A TW105130943A TWI653254B TW I653254 B TWI653254 B TW I653254B TW 105130943 A TW105130943 A TW 105130943A TW 105130943 A TW105130943 A TW 105130943A TW I653254 B TWI653254 B TW I653254B
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- -1 Methoxy, ethoxy Chemical group 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
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- 239000010703 silicon Substances 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
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- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 description 4
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- PWFLISNWYDWJHX-UHFFFAOYSA-N 9h-fluoren-1-ol Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2O PWFLISNWYDWJHX-UHFFFAOYSA-N 0.000 description 3
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
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- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
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- OEYNWAWWSZUGDU-UHFFFAOYSA-N 1-methoxypropane-1,2-diol Chemical compound COC(O)C(C)O OEYNWAWWSZUGDU-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- NJQJGRGGIUNVAB-UHFFFAOYSA-N 2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one Chemical compound BrC1=CC(Br)(Br)C=C(Br)C1=O NJQJGRGGIUNVAB-UHFFFAOYSA-N 0.000 description 1
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- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- 229910052581 Si3N4 Inorganic materials 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- ZENVDAOWLCNJHY-UHFFFAOYSA-N carbonic acid;naphthalene Chemical compound OC(O)=O.C1=CC=CC2=CC=CC=C21 ZENVDAOWLCNJHY-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
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- 239000012039 electrophile Substances 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 238000000445 field-emission scanning electron microscopy Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- 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
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
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Abstract
本發明提供包含由化學式1表示的結構單元的聚合物,和包含所述聚合物的有機層組成物,以及形成圖案的方法。 [化學式1]
Description
本申請主張2015年10月19日在韓國智慧財產權局提交的韓國專利申請第10-2015-0145367號的優先權和權益,其全部內容以引用的方式併入本文中。
本發明公開一種新穎聚合物、包含所述聚合物的有機層組成物以及使用所述有機層組成物形成圖案的方法。
最近,根據電子裝置的尺寸下調(小型化)和複雜性的高度集成設計已加快更高級材料和其相關製程的發展,並且因此,使用常規的光阻的光刻法也需要新的圖案化材料和技術。
在圖案化製程中,稱為硬罩幕層的有機層可形成為硬夾層以將光阻的精細圖案轉移到基底上的足夠深度處而不導致所述圖案崩塌。
硬罩幕層具有通過選擇性蝕刻製程來將光阻的精細圖案轉移到材料層的間層的作用。因此,硬罩幕層需要如抗蝕刻性等的特徵以經受多蝕刻製程。
另一方面,最近已建議使用旋塗法而非化學氣相沉積(CVD)法形成硬罩幕層。一般來說,因為耐熱性和抗蝕刻性與旋塗特徵具有折衷(trade-off)關係,所以需要滿足所有特徵的有機層材料。
一個實施例提供一種具有極好的抗蝕刻性並且同時具有良好溶解度特徵的聚合物。
另一個實施例提供一種包含所述聚合物的有機層組成物。
又一個實施例提供一種使用有機層組成物形成圖案的方法。
根據一個實施例,提供一種包含由化學式1表示的結構單元的聚合物。 [化學式1]在化學式1中, A為衍生自族群1中的一個化合物的經取代或未經取代的二價環基, B為二價有機基團,以及 *為連接點。 [族群1]在族群1中, R0
和R1
獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合。
在族群1中,R1
可為經取代或未經取代的苯基。
在化學式1中,B可為經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基或其組合。
由化學式1表示結構單元可由化學式1-1和化學式1-2中的一者表示。 [化學式1-1][化學式1-2]在化學式1-1和化學式1-2中, Z1
為NR10
、氧(O)或硫(S),Z2
為氮(N), R10
、R11
以及R12
獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, R13
到R15
獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, a和b獨立地為介於0到3範圍內的整數, c為0或1,且 *為連接點。
聚合物可更包含由化學式2表示的結構單元。 [化學式2]在化學式2中, C為包含經取代或未經取代的芳環的基團, D為二價有機基團,以及 *為連接點。
在化學式2中,C可為衍生自族群2中的一個化合物的經取代或未經取代的二價環基。 [族群2]在族群2中, Q1
和Q2
獨立地為單鍵、經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基、C=O、NRa
、氧(O)、硫(S)或其組合, Q3
為氮(N)、CRb
或其組合,且 Ra
和Rb
獨立地為氫、經取代或未經取代的C1到C10烷基、鹵素原子、含鹵素的基團或其組合。
在化學式2中,D可為經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基或其組合。
由化學式2表示的結構單元可由化學式2-1到化學式2-3中的一者表示。 [化學式2-1][化學式2-2][化學式2-3]在化學式2-1到化學式2-3中, R21
和R22
獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, R23
到R26
獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, e到h獨立地為介於0到2範圍內的整數,且 *為連接點。
聚合物的重量平均分子量可為約500到約200,000。
根據另一個實施例,提供一種包含所述聚合物和溶劑的有機層組成物。
根據又一個實施例,一種形成圖案的方法包含:在基底上提供材料層,在材料層上塗覆有機層組成物,熱處理有機層組成物以形成硬罩幕層,在硬罩幕層上形成含矽薄層,在含矽薄層上形成光阻層,使光阻層曝光並且顯影以形成光阻圖案,使用光阻圖案選擇性地去除含矽薄層和硬罩幕層以使材料層的一部分暴露,以及蝕刻材料層的暴露部分。有機層組成物可使用旋塗法塗覆。
新穎聚合物具有令人滿意的溶解度特徵以及極好的機械特徵、抗蝕刻性以及抗熱性且因此適用於旋塗法中。
本發明的示例性實施例將在下文中進行詳細描述,並且可以容易地由相關領域中具有通常知識者執行。然而,本發明可按多種不同形式實施,並且不理解為限於本文中所闡述的示例性實施例。
如本文所使用,當未另外提供定義時,術語「取代」可指由選自以下的取代基代替化合物的氫而經取代者:鹵素原子(F、Br、Cl或I)、羥基、烷氧基、硝基、氰基、氨基、疊氮基、甲脒基、肼基、亞肼基、羰基、氨甲醯基、硫醇基、酯基、羧基或其鹽、磺酸基或其鹽、磷酸基或其鹽、C1到C20烷基、C2到C20烯基、C2到C20炔基、C6到C30芳基、C7到C30芳烷基、C1到C30烷氧基、C1到C20雜烷基、C2到C20雜芳基、C3到C20雜芳烷基、C3到C30環烷基、C3到C15環烯基、C6到C15環炔基、C2到C30雜環烷基以及其組合。
如本文所用,當未另外提供定義時,術語「雜」是指包含1到3個由以下各者中選出的雜原子:N、O、S以及P。
下文中,描述根據一個實施例的聚合物。
根據一個實施例的聚合物包含由化學式1表示的結構單元。 [化學式1]在化學式1中, A為包含至少一個雜原子的烴環基且由族群1中選出,B為二價有機基團,以及*為連接點。 [族群1]在族群1中, R0
和R1
獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合。
由化學式1表示的結構單元中由族群1中選出的環基的連接點不受特定限制。另外,由族群1中選出的環基中的氫可經取代基置換,且在本文中,取代基的類別和數目不受特定限制。
聚合物包含在由化學式1表示的結構單元中包含雜原子的烴環基。
聚合物在結構單元中包含雜原子,如氮、氧或硫,因此可不僅確保抗蝕刻性,而且基於極性通過雜原子增加而提高溶解度。另外,聚合物在結構單元中包含烴環基,因此由使用聚合物形成的有機層可確保極好的膜密度。
舉例來說,在化學式1中,當A為、或時,R1
可為經取代或未經取代的芳環基,例如經取代或未經取代的苯基。
在化學式1中,由B表示的二價有機基團可例如為經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基或其組合的鍵聯基團。
舉例來說,在化學式1中,B可為未經取代的C1到C20伸烷基,或C1到C20伸烷基,其中至少一個氫經羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合置換,但不限於此。
舉例來說,由化學式1表示的結構單元可由化學式1-1和化學式1-2中的一者表示,但不限於此。 [化學式1-1][化學式1-2]在化學式1-1和化學式1-2中, Z1
為NR10
、氧(O)或硫(S),Z2
為氮(N), R10
、R11
以及R12
獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, R13
到R15
獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, a和b獨立地為介於0到3範圍內的整數, c為0或1,且 *為連接點。
聚合物可更包含由化學式2表示的結構單元。 [化學式2]在化學式2中, C為包含經取代或未經取代的芳環的基團, D為二價有機基團,以及 *為連接點。
舉例來說,在化學式2中,C可為衍生自族群2中的一個化合物的經取代或未經取代的二價環基。 [族群2]在族群2中, Q1
和Q2
獨立地為單鍵、經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基、C=O、NRa
、氧(O)、硫(S)或其組合, Q3
為氮(N)、CRb
或其組合,且 Ra
和Rb
獨立地為氫、經取代或未經取代的C1到C10烷基、鹵素原子、含鹵素的基團或其組合。
舉例來說,在化學式2中,D可為以下的鍵聯基團:經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基或其組合。
舉例來說,在化學式2中,D可為未經取代的C1到C20伸烷基或C1到C20伸烷基,其中至少一個氫經羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合置換,但不限於此。
舉例來說,由化學式2表示的結構單元可由化學式2-1到化學式2-3中的一者表示,但不限於此。 [化學式2-1][化學式2-2][化學式2-3]在化學式2-1到化學式2-3中, R21
和R22
獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, R23
到R26
獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合, e到h獨立地為介於0到2範圍內的整數,且 *為連接點。
聚合物可更包含由化學式2表示的結構單元,且進而聚合物可具有改進的抗蝕刻性。
舉例來說,聚合物可通過使用作為親核試劑的雜芳環結構和作為親電子試劑的多芳環結構單體的縮合聚合來製備。舉例來說,包含於由化學式1表示的結構單元中的如氮、氧或硫的雜原子可在形成聚合物之後起阻燃劑的作用,因此改進聚合物的抗蝕刻性以及在縮合聚合期間起還原劑的作用。
舉例來說,聚合物的重量平均分子量可為約500到約200,000。當聚合物的重量平均分子量在所述範圍內時,包含所述聚合物的有機層組成物(例如硬罩幕組成物)可通過調節碳的量和溶劑中的溶解度而最優化。
當聚合物用作有機層材料時,可不僅在下部基底(或膜)中存在梯級時或形成圖案時提供極好的間隙填充和平坦化特徵,而且還可在於烘烤期間不形成針孔和空隙或不使厚度分佈劣化的情況下形成均一薄膜。
根據另一個實施例,提供一種包含所述聚合物和溶劑的有機層組成物。
溶劑可為足以溶解或分散聚合物的任何溶劑,並且可為例如由以下各者中選出的至少一者:丙二醇、二乙酸丙二醇酯、甲氧基丙二醇、二甘醇、二甘醇丁基醚、三(乙二醇)單甲基醚、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、環己酮、乳酸乙酯、γ-丁內酯、甲基吡咯烷酮、乙醯丙酮以及3-乙氧基丙酸乙酯。
聚合物可按有機層組成物的總量計約1重量%到50重量%的量包含在內。當聚合物以所述範圍被包含時,可控制有機層的厚度、表面粗糙度以及平坦化。
有機層組成物可更包含表面活性劑、交聯劑、熱酸產生劑、塑化劑等添加劑。
表面活性劑可包含例如烷基苯磺酸鹽、烷基吡啶鎓鹽、聚乙二醇或季銨鹽,但並不限於此。
交聯劑可例如為三聚氰胺類試劑、經取代的脲類試劑或聚合物類試劑。在一個實施例中,具有至少兩個交聯形成取代基的交聯劑可例如為如甲氧基甲基化甘脲、丁氧基甲基化甘脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯並胍胺、丁氧基甲基化苯並胍胺、甲氧基甲基化脲、丁氧基甲基化脲、甲氧基甲基化硫脲或丁氧基甲基化硫脲等的化合物。
交聯劑可以是具有較高耐熱性的交聯劑。具有較高耐熱性的交聯劑可以是在分子中包括含芳族環(例如苯環或萘環)的交聯取代基的化合物。
熱酸產生劑可以是例如酸性化合物,如對甲苯磺酸、三氟甲磺酸、對甲苯磺酸吡啶鎓、水楊酸、磺基水楊酸、檸檬酸、苯甲酸、羥基苯甲酸、萘碳酸等或/和2,4,4,6-四溴環己二烯酮、安息香甲苯磺酸酯、2-硝基苯甲基甲苯磺酸酯、其它有機磺酸烷基酯等,但不限於此。
以100重量份的有機層組成物計,添加劑可以約0.001重量份到40重量份的量存在。當添加劑以所述範圍被包含時,可在不改變有機層組成物光學特性的情況下改進溶解度。
根據另一個實施例,提供使用有機層組成物製造的有機層。有機層可例如由在基底上塗布有機層組成物並且對其進行熱處理以固化來形成,並且可包含例如硬罩幕層、平坦化層、犧牲層、填充物等以用於電子裝置。
下文描述一種通過使用有機層組成物形成圖案的方法。
根據一個實施例,形成圖案的方法包含:在基底上提供材料層,塗覆包含聚合物和溶劑的有機層組成物,熱處理包含單體和溶劑的有機層組成物以形成硬罩幕層,在硬罩幕層上形成含矽薄層,在含矽薄層上形成光阻層,使光阻層曝光並且顯影以形成光阻圖案,使用光阻圖案選擇性地去除含矽薄層和硬罩幕層以使材料層的一部分暴露,以及蝕刻材料層的暴露部分。
基底可以是例如矽晶圓、玻璃基底或聚合物基底。
材料層為最終將圖案化的材料,例如,金屬層,如鋁層和銅層;半導體層,如矽層;或絕緣層,如氧化矽層和氮化矽層。材料層可通過如化學氣相沉積(chemical vapor deposition;CVD)製程的方法來形成。
有機層組成物與上文所述的相同,並且可按溶液形式通過旋塗法來塗覆。本文中,有機層組成物的厚度不受特別限制,但可以是例如約50埃到約100,000埃。
可在例如約100℃到約500℃下進行有機層組成物的熱處理約10秒到約1小時。
含矽薄層可由例如SiCN、SiOC、SiON、SiOCN、SiC、SiO和/或SiN形成。
所述方法可更包含在於含矽薄層上形成光阻層之前形成底部抗反射塗層(BARC)。
光阻層的曝光可使用例如ArF、KrF或EUV進行。在曝光之後,熱處理可在約100℃到約500℃下進行。
可經由使用蝕刻氣體的乾式蝕刻製程對材料層的暴露部分實施蝕刻製程,且蝕刻氣體可為例如(但不限於)CHF3
、CF4
、Cl2
、BCl3
以及其混合氣體。
經蝕刻的材料層可以多個圖案形成,並且多個圖案可以是金屬圖案、半導體圖案、絕緣圖案以及其類似圖案,例如半導體積體電路裝置的不同圖案。
在下文中,參考實例對本發明進行更詳細地說明。然而,這些實例是示例性的,並且本發明並不限於此。合成實例 合成實例 1
將吲哚(3.5克,30莫耳)、芘(6克,30莫耳)以及多聚甲醛(1.8克,20莫耳)放入250毫升燒瓶中。隨後,將通過溶解對甲苯磺酸單水合物(0.57克,3毫莫耳)於100克丙二醇單甲基醚乙酸酯(propylene glycol monomethyl ether acetate,PGMEA)中獲得的溶液放入燒瓶中,且在90℃下攪拌混合物。接著,每小時從聚合反應物獲取樣品,且當樣品具有3,000到3,500的重量平均分子量時,反應完成。
當反應完成時,將反應物冷卻到室溫並且添加到300克蒸餾水和300克甲醇中,並將混合物劇烈攪拌並使其靜置。在自其去除上清液之後,其中的沉澱溶解於100克丙二醇單甲基醚乙酸酯(PGMEA)中,且溶液與300克甲醇和300克蒸餾水一起劇烈攪拌並使其靜置(第一製程)。在再次自其去除獲得的上清液之後,其中的沉澱溶解於80克丙二醇單甲基醚乙酸酯(PGMEA)中(第二製程)。第一製程和第二製程被視為一個純化製程,並且這一純化製程重複三次。
使純化聚合物溶解於80克丙二醇單甲基醚乙酸酯(PGMEA)中,並且在減壓下去除殘存於溶液中的甲醇和蒸餾水,獲得包含由化學式1a表示的結構單元的聚合物。 [化學式1a](重量平均分子量:2,800和多分散性:1.51)合成實例 2
根據與合成實例1相同的方法製備由化學式1b表示的聚合物,不同之處在於使用羥基芘代替合成實例1中的芘。 [化學式1b](重量平均分子量:3,150和多分散性:1.59)合成實例 3
根據與合成實例1相同的方法製備包含由化學式1c表示的結構單元的聚合物,不同之處在於使用1-萘酚代替合成實例1中的芘。 [化學式1c](重量平均分子量:1,890和多分散性:1.45)合成實例 4
根據與合成實例1相同的方法製備包含由化學式1d表示的結構單元的聚合物,不同之處在於使用2-苯基苯並噁唑代替吲哚且使用1-萘酚代替合成實例1中的芘。 [化學式1d](重量平均分子量:2,630和多分散性:1.70)合成實例 5
根據與合成實例1相同的方法製備包含由化學式1e表示的結構單元的聚合物,不同之處在於使用2-苯基苯並噁唑代替吲哚且使用羥基芘代替合成實例1中的芘。 [化學式1e](重量平均分子量:3,080和多分散性:1.41)合成實例 6
根據與合成實例1相同的方法製備包含由化學式1f表示的結構單元的聚合物,不同之處在於使用2-苯基苯並噁唑代替吲哚且使用1-萘酚代替合成實例1中的芘。 [化學式1f](重量平均分子量:3,650和多分散性:1.38)合成實例 7
根據與合成實例1相同的方法製備包含由化學式1g表示的結構單元的聚合物,不同之處在於使用2-苯基苯並噁唑代替吲哚且使用羥基芘代替合成實例1中的芘 [化學式1g](重量平均分子量:3,810和多分散性:1.72)合成實例 8
根據與合成實例1相同的方法製備包含由化學式1h表示的結構單元的聚合物,不同之處在於使用4,4'-(9H-芴-9,9-二基)二酚代替合成實例1中的芘。 [化學式1h](重量平均分子量:3,900和多分散性:1.69)合成比 較 例 1
將9,9-雙(4-羥基苯基)-9H-芴(21克,0.057莫耳)和4,4-甲氧基甲苯(9.6克,0.057莫耳)依序放入500毫升燒瓶中且溶解於51克丙二醇單甲基醚乙酸酯(PGMEA)中,將對甲苯磺酸單水合物(0.001莫耳)添加到其中,且在100℃下攪拌混合物5小時。接著,每小時從聚合反應物獲取樣品,且當樣品具有3,500到4,000的重量平均分子量時,反應完成。接著,通過與合成實例1相同的純化製程獲得包含由化學式A表示的結構單元的聚合物。 [化學式A] 合成比較例 2
將9,9-雙(4-羥基苯基)-9H-芴(35克,0.1莫耳)、1-萘酚(14.4克,0.1莫耳)以及三聚甲醛(1.2克,0.034莫耳)放入500毫升燒瓶中。隨後,將通過溶解對甲苯磺酸單水合物(0.19克,0.34莫耳)於162克丙二醇單甲基醚乙酸酯(PGMEA)中獲得的溶液添加到燒瓶中。在100℃下攪拌混合物5小時。接著,每小時從聚合反應物獲取樣品,且當樣品具有3,500到4,000的重量平均分子量時,反應完成。接著,通過與合成比較例1相同的純化製程獲得包含由化學式B表示的結構單元的聚合物。 [化學式B] 製 備 硬罩幕 組 成物 實例 1
根據合成實例1的聚合物溶解於丙二醇單甲基醚乙酸酯(PGMEA)和乳酸乙酯(EL)(7:3(v/v))的混合溶劑中,且用0.1 μm鐵氟龍(TEFLON)(四氟乙烯)過濾器過濾溶液,製備硬罩幕組成物。取決於所要厚度,在關於按硬罩幕組成物的總重量計3.0重量%到15.0重量%範圍內的重量調節聚合物。實例 2 到實例 8
根據實例2到實例8的每一硬罩幕組成物根據與實例1相同的方法製備,不同之處在於分別使用根據合成實例2到合成實例8的聚合物代替根據合成實例1的化合物。比較例 1 和比較例 2
每一硬罩幕組成物根據與實例1相同的方法製備,不同之處在於分別使用根據合成比較例1和合成比較例2的聚合物代替根據合成實例1的聚合物。評 估 1 :膜密度
根據實例1到實例8和比較例1和比較例2的每一硬罩幕組成物旋塗於矽晶圓上,在400℃下熱處理2分鐘,形成約1000埃厚的薄膜。通過使用由帕納科(PANalytical)製造的X射線繞射設備測量薄膜的膜密度。
結果在表1中示出。 [表1]
參看表1,分別由根據實例1到實例8的硬罩幕組成物形成的每一薄膜比分別由根據比較例1和比較例2的硬罩幕組成物形成的每一薄膜顯示更高膜密度。
換句話說,相比於根據比較例1和比較例2的硬罩幕組成物,根據實例1到實例8的硬罩幕組成物全部形成緻密且堅實的薄膜。評估 2 : 逸氣
根據實例1到實例8和比較例1和比較例2的硬罩幕組成物分別在矽晶圓上塗布為約2000埃厚且在400℃下烘烤5分鐘,且通過使用石英晶體微天平(Quartz Crystal Microbalance;QCM)測量在烘烤期間產生的逸氣,且根據圖1中的計算方程式1計算逸氣的量(奈克)。
結果示出在表2中。 [表2]
參看表2,相比於分別由根據比較例1和比較例2的硬罩幕組成物形成的每一薄膜,分別由根據實例1到實例8的硬罩幕組成物形成的每一薄膜在烘烤期間在400℃的高溫下產生相對較小量的逸氣。因此,確認根據實例1到實例8的硬罩幕組成物有利地應用於高溫製程。評估 3 : 抗蝕刻性
根據實例1到實例8和比較例1和比較例2的硬罩幕組成物分別旋塗於矽晶圓上且在400℃下在熱板上烘烤2分鐘,形成約4000埃厚的薄膜。通過使用K-MAC製造的薄膜厚度測量設備來測量薄膜的厚度。
隨後,分別用CF4
氣體和N2
/O2
混合氣體乾式蝕刻薄膜60秒和100秒,且接著測量薄膜的厚度。
從如計算方程式2中所示的整體蝕刻速率(BER)評估薄膜的抗蝕刻性。 [計算方程式2] 整體蝕刻速率(BER)= (薄膜初始厚度-蝕刻後薄膜厚度)/蝕刻時間(埃/秒)
結果示於表3中。 [表3]
參看表3,分別由根據實例1到實例8的硬罩幕組成物形成的每一薄膜比分別由根據比較例1和比較例2的硬罩幕組成物形成的每一薄膜顯示更低整體蝕刻速率。
因此,相比於根據比較例1和比較例2的硬罩幕組成物,根據實例1到實例8的硬罩幕組成物顯示高抗蝕刻性。評估 4 : 間隙填充和平坦化特徵
根據實例1到實例8和比較例1和比較例2的硬罩幕組成物分別旋塗於圖案化矽晶圓上且在400℃下烘烤2分鐘,且接著通過使用FE-SEM設備檢查間隙填充特徵和平坦化特徵。
通過用電子掃描顯微鏡(SEM)檢查圖案的橫截面以查看是否存在空隙來評估間隙填充特徵,且通過從圖案橫截面的SEM圖像測量硬罩幕層的厚度且將其放入圖2的計算方程式3中評估平坦化特徵。本文中,平坦化特徵極好,因為厚度h1與厚度h2之間的差異較小。
另一方面,通過調節包含於根據實例1到實例8和比較例1和比較例2的硬罩幕組成物中的聚合物的量,烘烤之後的厚度h1為2000埃。
結果示於表4中。 [表4]
參看表4,根據實例1到實例8的硬罩幕組成物顯示相比於根據比較例1和比較例2的硬罩幕組成物的極好平坦化,以及深圖案深度(縱橫比=1:15)的條件下的無空隙,因此間隙填充特徵極好。
雖然已經結合目前視為實用示例性實施例的內容來描述本發明,但應理解本發明不限於所公開的實施例,而是相反,本發明旨在涵蓋包含在所附申請專利範圍的精神和範圍內的各種修改和等效佈置。
無
圖1為解釋計算逸氣量的計算方程式1的參考圖式。 圖2為解釋評估平坦化特徵的計算方程式3的參考圖式。
Claims (14)
- 一種聚合物,包括由化學式1-1和化學式1-2中的一者表示的結構單元: 其中,在化學式1-1和化學式1-2中,Z1為NR10、氧或硫,Z2為氮,R10、R11以及R12獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,R13到R15獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,a和b獨立地為介於0到3範圍內的整數,c為0或1,以及*為連接點。
- 如申請專利範圍第1項所述的聚合物,其中所述聚合物更包括由化學式2表示的結構單元:其中,在化學式2中,C為包含經取代或未經取代的芳環的基團,D為二價有機基團,以及*為連接點。
- 如申請專利範圍第2項所述的聚合物,其中C為衍生自族群2中的一個化合物的經取代或未經取代的二價環基:[族群2]其中,在族群2中,Q1和Q2獨立地為單鍵、經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基、C=O、NRa、氧、硫或其組合,Q3為氮、CRb或其組合,以及Ra和Rb獨立地為氫、經取代或未經取代的C1到C10烷基、鹵素原子、含鹵素的基團或其組合。
- 如申請專利範圍第2項所述的聚合物,其中D為經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基或其組合。
- 如申請專利範圍第2項所述的聚合物,其中由化學式2表示的結構單元由化學式2-1到化學式2-3中的一者表示: 其中,在化學式2-1到化學式2-3中,R21和R22獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,R23到R26獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,e到h獨立地為介於0到2範圍內的整數,以及*為連接點。
- 如申請專利範圍第1項所述的聚合物,其中所述聚合物的重量平均分子量為500到200,000。
- 一種有機層組成物,包括包含由化學式1-1和化學式1-2中的一者表示的結構單元的聚合物以及溶劑: 其中,在化學式1-1和化學式1-2中,Z1為NR10、氧或硫,Z2為氮,R10、R11以及R12獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,R13到R15獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,a和b獨立地為介於0到3範圍內的整數,c為0或1,以及*為連接點。
- 如申請專利範圍第7項所述的有機層組成物,其中所述聚合物更包括由化學式2表示的結構單元:其中,在化學式2中,C為包含經取代或未經取代的芳環的基團,D為二價有機基團,以及*為連接點。
- 如申請專利範圍第8項所述的有機層組成物,其中C為衍生自族群2中的一個化合物的經取代或未經取代的二價環基:[族群2]其中,在族群2中,Q1和Q2獨立地為單鍵、經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基、C=O、NRa、氧、硫或其組合,Q3為氮、CRb或其組合,以及Ra和Rb獨立地為氫、經取代或未經取代的C1到C10烷基、鹵素原子、含鹵素的基團或其組合。
- 如申請專利範圍第8項所述的有機層組成物,其中D為經取代或未經取代的C1到C20伸烷基、經取代或未經取代的C3到C20伸環烷基、經取代或未經取代的C6到C20伸芳基、經取代或未經取代的C2到C20伸雜芳基、經取代或未經取代的C2到C20伸烯基、經取代或未經取代的C2到C20伸炔基或其組合。
- 如申請專利範圍第8項所述的有機層組成物,其中由化學式2表示的結構單元由化學式2-1到化學式2-3中的一者表示: 其中,在化學式2-1到化學式2-3中,R21和R22獨立地為氫、羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,R23到R26獨立地為羥基、甲氧基、乙氧基、鹵素原子、含鹵素的基團、經取代或未經取代的C1到C30烷基、經取代或未經取代的C6到C30芳基或其組合,e到h獨立地為介於0到2範圍內的整數,以及*為連接點。
- 如申請專利範圍第7項所述的有機層組成物,其中所述聚合物的重量平均分子量為500到200,000。
- 一種形成圖案的方法,包括:在基底上提供材料層,在所述材料層上塗覆如申請專利範圍第7項到第12項中任一項所述的有機層組成物,熱處理所述有機層組成物以提供硬罩幕層,在所述硬罩幕層上提供含矽薄層,在所述含矽薄層上提供光阻層,使所述光阻層曝光並且顯影以形成光阻圖案,使用所述光阻圖案選擇性地去除所述含矽薄層和所述硬罩幕層以使所述材料層的一部分暴露,以及蝕刻所述材料層的暴露部分。
- 如申請專利範圍第13項所述的形成圖案的方法,其中所述有機層組成物使用旋塗法塗覆。
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US20170110328A1 (en) | 2017-04-20 |
CN107337776A (zh) | 2017-11-10 |
TW201714912A (zh) | 2017-05-01 |
KR20170045592A (ko) | 2017-04-27 |
KR101829750B1 (ko) | 2018-02-19 |
CN107337776B (zh) | 2019-12-31 |
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