TWI589619B - 聚合物、有機層組合物、有機層以及形成圖案的方法 - Google Patents
聚合物、有機層組合物、有機層以及形成圖案的方法 Download PDFInfo
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- TWI589619B TWI589619B TW104137788A TW104137788A TWI589619B TW I589619 B TWI589619 B TW I589619B TW 104137788 A TW104137788 A TW 104137788A TW 104137788 A TW104137788 A TW 104137788A TW I589619 B TWI589619 B TW I589619B
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- 239000000203 mixture Substances 0.000 title claims description 52
- 239000012044 organic layer Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 31
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- 239000000126 substance Substances 0.000 claims description 66
- 150000001875 compounds Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 239000000463 material Substances 0.000 claims description 23
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- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 11
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
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- UVHIWKCVGUMHNB-UHFFFAOYSA-N 5,7-dihydroindolo[2,3-b]carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=C1NC3=CC=CC=C3C1=C2 UVHIWKCVGUMHNB-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000005843 halogen group Chemical group 0.000 description 1
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- VHHBCZRHMHRNTP-UHFFFAOYSA-N methoxymethylthiourea Chemical compound COCNC(N)=S VHHBCZRHMHRNTP-UHFFFAOYSA-N 0.000 description 1
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- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 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
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Description
本申請案主張2014年11月28日在韓國智慧財產權局提交的韓國專利申請案第10-2014-0169131號的優先權和權益,所述專利申請案的全部內容以引用的方式併入本文中。
本發明公開一種聚合物、包含所述聚合物的有機層組合物、由所述有機層組合物製成的有機層以及使用所述有機層組合物形成圖案的方法。
近來,半導體工業已開發具有數納米至數十納米尺寸圖案的超精細技術。所述超精細技術本質上需要有效平版印刷(lithographic)技術。典型平版印刷技術包含在半導體基底上提供材料層;在其上塗布光阻層;將其曝光和顯影以提供光阻圖案;以及使用光阻圖案作為罩幕來蝕刻材料層。如今,根據待形成圖案小型化,難以僅通過上述典型平版印刷技術提供具有極好輪廓的精細圖案。因此,可以在材料層與光阻層之間形成稱為硬罩幕
層的層以得到精細圖案。硬罩幕層發揮中間層的作用,將光阻的精細圖案通過選擇性蝕刻製程轉移到材料層。因此,硬罩幕層需要具有如耐熱性和耐蝕刻性等在多個蝕刻製程期間耐受的特徵。另一方面,近來已建議通過旋塗法代替化學氣相沉積形成硬罩幕層。旋塗法容易進行,並且也可以改善間隙填充特徵和平坦化特徵。然而,旋塗法需要溶劑的可溶性。需要開發滿足硬罩幕層特徵的有機層材料。
一個實施例提供一種同時確保溶劑可溶性、耐蝕刻性以及儲存穩定性的聚合物。
另一個實施例提供一種包含所述聚合物的有機層組合物。
又一個實施例提供一種同時確保耐蝕刻性以及平坦化特徵的有機層。
再一個實施例提供一種使用所述有機層組合物形成圖案的方法。
根據一個實施例,提供一種包含由化學式1表示的部分的聚合物。
在化學式1中,A1和A2各自獨立地是衍生自含氮原子的芳環基團的二價基
團,A3和A4各自獨立地是由化學式2表示的二價基團,以及n是0或1。
氮原子與經取代或未經取代的C1到C30烷基、被至少一個氧原子(-O-)間斷開的經取代或未經取代的C1到C30烷基、含羰基(-C(=O)-)的基團或其組合鍵結。
在化學式2中,X1和X2各自獨立地是經取代或未經取代的C6到C30芳基,以及X3是經取代或未經取代的C6到C50伸芳基。
經取代或未經取代的含氮原子的芳環基團可以是群組1中列出的化合物中的一個。
[群組1]
在群組1中,R1、R2以及R3獨立地是經取代或未經取代的C1到C30烷基、被至少一個氧原子(-O-)間斷開的經取代或未經取代的C1到C30
烷基、含羰基(-C(=O)-)的基團或其組合,Z1到Z6獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷基胺基、經取代或未經取代的C7到C20芳基烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,以及a、b、c、d、e以及f各自獨立地是0到2的整數。
R1、R2以及R3可以是包含至少三個碳的基團。
R1、R2以及R3可以是由化學式3到化學式6中的一個表示的基團。
[化學式3]-(CkH2k+1)
在化學式3到化學式6中,
k、m以及t各自獨立地是介於1到10範圍內的整數。
在化學式3中,k可以是3到10的整數。
在化學式6中,-(CkH2k+1)可以是叔丁基。
在化學式2中,X1和X2可以各自獨立地是衍生自群組2中列出的化合物中的一個的單價基團,並且X3可以是衍生自群組2中列出的化合物中的一個的二價基團。
在化學式2中,X1、X2以及X3中的至少一個可以是衍生自經取代或未經取代的萘、經取代或未經取代的聯苯、經取代或未經取代的芘、經取代或未經取代的苝、經取代或未經取代的苯並芘、經取代或未經取代的蔻或其組合的基團。
聚合物可以包含由化學式1-1到化學式1-4中的一個表示的重複單元結構。
在化學式1-1到化學式1-4中,R4和R5各自獨立地是經取代或未經取代的C1到C30烷基、被至少一個氧原子(-O-)間斷開的經取代或未經取代的C1到C30烷基、含羰基(-C(=O)-)的基團或其組合,Z11到Z22各自獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br或-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷基胺基、經取代或未經取代的C7到C20芳基烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,n11到n22各自獨立地是0到2的整數,以及n0是2到300的整數。
聚合物的重量平均分子量可以是約1,000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合物。
以所述有機層組合物的總量計,所述聚合物可以約0.1重量%到約30重量%的量存在。
根據又一個實施例,提供一種通過固化所述有機層組合物獲得的有機層。
根據另一個實施例,形成圖案的方法包含在基底上提供材料層,在所述材料層上施用所述有機層組合物,熱處理所述有機層組合物以形成硬罩幕層,在所述硬罩幕層上形成含矽薄層,在所述含矽薄層上形成光阻層,將所述光阻層曝光和顯影以形成光阻圖案,使用所述光阻圖案選擇性去除所述含矽薄層以暴露所述材料層的一部分,以及蝕刻所述材料層的暴露部分。
所述有機層組合物可以使用旋塗法來施用。
所述有機層可以通過在約100℃到約500℃下熱處理形成。
所述方法可以還包含在形成所述光阻層之前形成底部抗反射塗層(bottom antireflective coating,BARC)。
所述含矽薄層可以包含SiCN、SiOC、SiON、SiOCN、SiC、SiN或其組合。
可以提供具有改善的溶解性、耐蝕刻性以及儲存穩定性的有機層材料。
本發明的示例性實施例將在下文中加以詳細描述,並且可以輕易地由相關技術領域的一般技術人員執行。然而,本發明可以許多不同形式實施並且不應視為局限於本文中陳述的示例性實施例。
當並未另外提供定義時,本文所用的術語「經取代」可以指代由從以下各物中選出的取代基代替化合物的氫原子而經取代者:鹵素原子(F、Br、Cl或I)、羥基、烷氧基、硝基、氰基、氨基、疊氮基、脒基、肼基、亞肼基、羰基、胺甲醯基、硫醇基、酯基、羧基或其鹽、磺酸基或其鹽、磷酸或其鹽、C1到C20烷基、C2到C20烯基、C2到C20炔基、C6到C30芳基、C7到C30芳基烷基、C1到C30烷氧基、C1到C20雜烷基、C3到C20雜芳基烷基、C3到C30環烷基、C3到C15環烯基、C6到C15環炔基、C3到C30雜環烷基以及其組合。
當並未另外提供定義時,本文所用的術語「雜」是指包含1到3個從B、N、O、S以及P中選出的雜原子。
當並未另外提供定義時,本文所用的‘*’指示化合物或化合物的部分的連接點。
此外,衍生自A化合物的「單價基團」是指取代A化合物中一個氫的單價基團。舉例來說,衍生自苯基團的單價基團變成苯基。此外,衍生自A化合物的「二價基團」是指取代A化合物中兩個氫以形成兩個連接點的二價基團。舉例來說,衍生自苯
基團的二價基團變成伸苯基。
在下文中,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表示的部分。
在化學式1中,A1和A2各自獨立地是衍生自含氮原子的芳環基團的二價基團,A3和A4各自獨立地是由化學式2表示的二價基團,以及n是0或1。
氮原子與經取代或未經取代的C1到C30烷基、被至少一個氧原子(-O-)間斷開的經取代或未經取代的C1到C30烷基、含羰基(-C(=O)-)的基團或其組合鍵結。
在化學式2中,X1和X2各自獨立地是經取代或未經取代的C6到C30芳基,X3是經取代或未經取代的C6到C50伸芳基。
聚合物可以包含多個由化學式1表示的部分,並且所述多個部分可以具有相同的結構或彼此不同的結構。
化學式1具有包含由A1和A2表示的含氮原子的芳環基團部分以及由A3和A4表示的無氮原子的芳環基團部分的結構。
首先,描述含氮原子的芳環基團部分。
聚合物包含衍生自含氮原子的芳環基團的二價基團,並且所述氮原子與除氫原子以外的預先確定的取代基鍵結。
舉例來說,經取代或未經取代的含氮原子的芳環基團可以是群組1中列出的化合物中的一個。
[群組1]
在群組1中,R1、R2以及R3獨立地是經取代或未經取代的C1到C30烷基、被至少一個氧原子(-O-)間斷開的經取代或未經取代的C1到C30
烷基、含羰基(-C(=O)-)的基團或其組合,Z1到Z6獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷基胺基、經取代或未經取代的C7到C20芳基烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,以及a、b、c、d、e以及f各自獨立地是0到2的整數。
舉例來說,在群組1中,R1、R2以及R3可以是由化學式3到化學式6中的一個表示的基團,但不限於此。
[化學式3]-(CkH2k+1)
在化學式3到化學式6中,k、m以及t各自獨立地是介於1到10範圍內的整數。
以這種方式,聚合物包含衍生自含氮原子的芳環基團的二價基團,具有環基團的苄基氫減到最少而環參數達到最大的結構,並且因此可以保證極好的耐蝕刻性。
此外,由於芳環基團中所含的氮原子經單價有機基團而非氫原子取代,所以聚合物可以保證溶解性以及維持耐蝕刻性。
舉例來說,R1、R2以及R3可以是包含至少三個碳的基團。在化學式3中,k可以是例如3到10的整數。
舉例來說,在化學式6中,-(CkH2k+1)可以是叔丁基。
在下文中,在化學式1中,提供由A3和A4表示的無氮原子的芳環基團部分。
如上所述,在化學式1中,A3和A4是由化學式2表示。
在化學式2中,X1和X2各自獨立地是經取代或未經取代的C6到C30芳基,例如衍生自群組2中列出的化合物中的一個的單價基團。在化學式2中,X3可以是經取代或未經取代的C6到C50伸芳基,例如衍生自群組2中列出的化合物中的一個的二價基團。
[群組2]
由化學式2表示的無氮原子的芳環基團部分可以包含多環芳環基團。在化學式2中,X1、X2以及X3中的至少一個可以是例如衍生自經取代或未經取代的萘、經取代或未經取代的聯苯、經取代或未經取代的芘、經取代或未經取代的苝、經取代或未經取代的苯並芘、經取代或未經取代的蔻或其組合的基團,但不限於此。
舉例來說,聚合物可以包含由化學式1-1到化學式1-4中的一個表示的重複單元結構。
[化學式1-1]
[化學式1-4]
在化學式1-1到化學式1-4中,R4和R5各自獨立地是經取代或未經取代的C1到C30烷基、被至少一個氧原子(-O-)間斷開的經取代或未經取代的C1到C30烷基、含羰基(-C(=O)-)的基團或其組合,Z11到Z22各自獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷基胺基、經取代或未經取代的C7到C20芳基烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,n11到n22各自獨立地是0到2的整數,以及n0是2到300的整數。
聚合物的重量平均分子量可以是約1,000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合物(例如硬罩幕組合物)可以通過調節碳的量和在溶
劑中的溶解度而優化。
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合物。
溶劑可以是對所述聚合物具有足夠可溶性或分散性的任何溶劑,並且可以是例如從以下各物中選出的至少一個:丙二醇、丙二醇二乙酸酯、甲氧基丙二醇、二乙二醇、二乙二醇丁基醚、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、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、甲基吡咯烷酮(methylpyrrolidone)、甲基吡咯烷酮(methylpyrrolidinone)、乙醯丙酮以及3-乙氧基丙酸乙酯。
以所述有機層組合物的總量計,所述聚合物可以約0.1重量%到約30重量%的量存在。當包括所述範圍內的聚合物時,可以控制有機層的厚度、表面粗糙度以及平坦化。
有機層組合物可以還包含介面活性劑、交聯劑、熱酸產生劑、塑化劑等添加劑。
介面活性劑可以包含例如烷基苯磺酸鹽、烷基吡啶鹽、聚乙二醇或季銨鹽,但不限於此。
交聯劑可以是例如三聚氰胺系交聯劑、經取代的脲系交聯劑或其聚合物系交聯劑。優選地,具有至少兩個交聯形成取代基的交聯劑可以是例如以下化合物,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。
此外,交聯劑可具有高抗熱性。具有高抗熱性的交聯劑
可以是在其分子中含有具有芳香環(如,苯環、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、吡啶對甲苯磺酸、水楊酸、磺基水楊酸、檸檬酸、苯甲酸、羥基苯甲酸、萘甲酸等或/和2,4,4,6-四溴環己二烯酮、苯偶姻甲苯磺酸酯、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。
以所述有機層組合物的100重量份計,添加劑可以約0.001重量份到40重量份的量存在。當包含所述範圍內的添加劑時,可以提高溶解度而不改變所述有機層組合物的光學特性。
根據另一個實施例,提供一種使用所述有機層組合物製造的有機層。所述有機層可以例如通過將所述有機層組合物塗布在基底上並且將其熱處理以便固化而形成,並且可以包含例如用於電子裝置的硬罩幕層、平坦化層、犧牲層、填充劑等。
下文描述通過使用所述有機層組合物形成圖案的方法。
根據另一個實施例的形成圖案的方法包含在基底上提供材料層,施用包含聚合物和溶劑的有機層組合物,熱處理所述有機層組合物以形成硬罩幕層,在所述硬罩幕層上形成含矽薄層,在所述含矽薄層上形成光阻層,將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去除所述含矽薄層和所述硬罩幕層以暴露一部分所述材料層,以及蝕刻所述材料層的暴露部分。
基底可以是例如矽晶圓、玻璃基底或聚合物基底。
材料層是有待最後圖案化的材料,例如金屬層,如鋁層
和銅層;半導體層,如矽層;或絕緣層,如二氧化矽層和氮化矽層。材料層可以通過如化學氣相沉積(chemical vapor deposition,CVD)製程的方法形成。
有機層組合物與上文所述相同,並且可以通過以溶液形式旋塗來施用。在本文中,有機層組合物的厚度並未特別受限,而是可以是例如約50Å到約10,000Å。
熱處理有機層組合物可以例如在約100℃到約500℃下進行約10秒到1小時。
含矽薄層可以由例如以下材料形成,如SiCN、SiOC、SiON、SiOCN、SiC和/或SiN等。
所述方法可以還包含在含矽薄層上形成光阻層之前形成底部抗反射塗層(BARC)。
光阻層的曝光可以使用例如ArF、KrF或EUV來執行。
在曝光後,熱處理可以在約100℃到約500℃下進行。
材料層的暴露部分的蝕刻製程可以通過使用蝕刻氣體的乾式蝕刻製程來進行,並且蝕刻氣體可以是例如CHF3、CF4、Cl2、BCl3以及其混合氣體。
蝕刻的材料層可以按多個圖案形成,並且所述多個圖案可以是金屬圖案、半導體圖案、絕緣圖案等,例如半導體積體電路裝置的各種圖案。
在下文中參照實例更詳細地說明本發明。然而,這些實例是示例性的,並且本發明並不限於此。
將20g(0.1mol)芘和38g(0.2mol)萘甲醯氯置於配備有機械攪拌器和冷卻管的500ml 2頸燒瓶中並且溶解於219g 1,2-二氯乙烷中。十五分鐘後,向其中緩慢添加30g(0.22mol)三氯化鋁並且使反應溶液在室溫下反應5小時。當反應完成時,使用水去除三氯化鋁,並且使用蒸發器濃縮殘餘物。接著,將80g四氫呋喃添加到所獲得的化合物,從而獲得溶液。隨後,將10g(0.26mol)硼氫化鈉水溶液緩慢添加到溶液中,並且在室溫下攪拌混合物12小時。當反應完成時,所得物用7%氯化氫溶液酸化成小於或等於pH 5並且用乙酸乙酯萃取,在減壓下從其中去除有機溶劑,從而獲得單體。
將6.08g(0.01mol)所述單體、1.15g(0.01mol)咔唑、1.9g(0.01mol)對甲苯磺酸水合物以及25g 1,4-二噁烷置於燒瓶中並且在100℃下攪拌。當每小時從聚合反應物獲取樣品並且樣品的重量平均分子量範圍介於2500到4500時,反應完成。當反應完成時,向其中添加100g己烷以萃取1,4-二噁烷,向其中添加水和甲醇,過濾其中的沉澱,並且通過使用甲醇去除剩餘的單體,從而獲得具有由化學式X表示的重複單元的聚合物(重量平均分子量=約4300)。
將27.64g(0.1mol)苯並芘、17.06g(0.1mol)4-甲氧基苯甲醯氯以及19g(0.1mol)萘甲醯氯置於配備有機械攪拌器和冷卻管的250ml 2頸燒瓶中並且溶解於178.12g 1,2-二氯乙烷中。十五分鐘後,向其中緩慢添加15g(0.11mol)三氯化鋁並且使反應溶液在室溫下反應5小時。當反應完成時,使用水去除三氯化鋁,並且使用蒸發器濃縮殘餘物。接著,將30.4g(0.15mol)1-十二烷硫醇、11.23g(0.2mol)氫氧化鉀以及229g 1-甲基-2-吡咯烷酮(NMP)添加到所獲得的化合物,並且在85℃下攪拌混合物。三小時後,當反應完成時,向其中添加具有1當量濃度的鹽酸水溶液和乙酸乙酯,從其中分離乙酸乙酯層,並且從其中去除鹼和催化劑。在減壓下濃縮乙酸乙酯層,並且向其中添加80g四氫呋喃,從而獲得溶液。接著,將10g(0.26mol)硼氫化鈉水溶液緩慢添加到溶液中,並且在室溫下攪拌混合物12小時。當反應完成時,所得物用7%氯化氫溶液酸化成小於或等於pH 5並且用乙酸乙酯萃取,在減壓下去除有機溶劑,從而獲得單體。
將6.08g(0.01mol)所述單體、1.15g(0.01mol)9H-二苯並[a,c]咔唑、1.9g(0.01mol)對甲苯磺酸水合物以及25g 1,4-二噁烷置於燒瓶中並且在100℃下攪拌。當每小時從聚合反應物獲取樣品並且樣品的重量平均分子量範圍介於2500到3500時,反應完成。當反應完成時,向其中添加100g己烷以萃取1,4-二噁烷,向其中添加水和甲醇,過濾其中的沉澱,並且通過使用甲醇去除剩餘的單體,從而獲得具有由化學式Y表示的重複單元的聚合物(重量平均分子量=約2600)。
將40.4g(0.2mol)芘和20g(0.1mol)對苯二甲醯氯置於配備有機械攪拌器和冷卻管的500ml 2頸燒瓶中並且溶解於300g 1,2-二氯乙烷中。十五分鐘後,向其中緩慢添加30g(0.22mol)三氯化鋁並且使反應溶液在室溫下反應5小時。當反應完成時,使用水去除三氯化鋁,並且使用蒸發器濃縮殘餘物。接著,將160g四氫呋喃添加到化合物,從而獲得溶液。隨後,將16g(0.42mol)硼氫化鈉水溶液緩慢添加到溶液中,並且在室溫下攪拌混合物12小時。當反應完成時,所得物用7%氯化氫溶液酸化成小於或等於pH 5並且用乙酸乙酯萃取,在減壓下去除有機溶劑,從而獲得單體。
將6.08g(0.01mol)所述單體、1.93g(0.01mol)5,7-二氫-吲哚並[2,3-b]咔唑、1.9g(0.01mol)對甲苯磺酸水合物以及25g 1,4-二噁烷置於燒瓶中並且在100℃下攪拌。當每小時從聚合反應物獲取的樣品的重量平均分子量是2500到3500時,反應完成。當反應完成時,向其中添加100g己烷以萃取1,4-二噁烷,
向其中添加水和甲醇,過濾其中的沉澱,並且通過使用甲醇去除其中剩餘的單體,從而獲得聚合物。
將7.79g(0.01mol)所述聚合物、3.05g(0.02mol)1-(2-氯乙氧基)-2-乙氧基乙烷、2.16g(0.09mol)氫化鈉以及48.17g四氫呋喃置於燒瓶中並且在室溫下攪拌。三小時後,反應完成。當反應完成時,使用飽和狀態的氯化銨水溶液和二氯甲烷去除氫化鈉,並且去除二氯甲烷層。將殘餘物在減壓下濃縮並且添加到己烷中,過濾其中的沉澱,從而獲得具有由化學式A表示的重複單元的聚合物(重量平均分子量=約3300)。
將30.0g(0.1mol)苝和34g(0.2mol)苯甲醯氯置於配備有機械攪拌器和冷卻管的500ml 2頸燒瓶中並且溶解於300g 1,2-二氯乙烷中。十五分鐘後,向其中緩慢添加30g(0.22mol)三氯化鋁並且使反應溶液在室溫下反應5小時。當反應完成時,使用水去除三氯化鋁,並且使用蒸發器濃縮殘餘物。接著,將160g四氫呋喃添加到化合物,從而獲得溶液。隨後,將16g(0.42mol)硼氫化鈉水溶液緩慢添加到溶液中,並且在室溫下攪拌混合物12小時。當反應完成時,所得物用7%氯化氫溶液酸化成小於或等於
pH 5並且用乙酸乙酯萃取,在減壓下從其中去除有機溶劑,從而獲得單體。
將6.08g(0.01mol)所述單體、1.93g(0.01mol)2,3’-聯吲哚、1.9g(0.01mol)對甲苯磺酸水合物以及25g 1,4-二噁烷置於燒瓶中並且在100℃下攪拌。當每小時從聚合反應物獲取的樣品的重量平均分子量是2500到3500時,反應完成。當反應完成時,向其中添加100g己烷以萃取1,4-二噁烷,向其中添加水和甲醇,過濾其中的沉澱,並且通過使用甲醇去除存在的剩餘單體,從而獲得聚合物。
將6.81g(0.01mol)所述聚合物、2.42g(0.02mol)1-氯己烷、2.16g(0.09mol)氫化鉀以及48.37g二甲基甲醯胺置於燒瓶中並且在室溫下攪拌。兩小時後,反應完成。當反應完成時,使用飽和狀態的氯化銨水溶液和二氯甲烷去除氫化鉀,去除二氯甲烷層,將殘餘物在減壓下濃縮並且添加到己烷中,並且過濾其中的沉澱,從而獲得具有由化學式B表示的重複單元的聚合物(重量平均分子量=約3100)。
將6.63g(0.01mol)比較合成實例1的聚合物、3.27g(0.015mol)二碳酸二叔丁酯(BOC)、3.27g(0.003mol)4-
二甲基氨基吡啶(4-dimethylaminopyridine,DMAP)以及37.09g二氯甲烷置於燒瓶中並且在室溫下攪拌。二十四小時後,反應完成。當反應完成時,向其中添加水,並且分離二氯甲烷層以去除DMAP。將萃取的二氯甲烷層添加到硫酸鈉中,並且通過過濾混合物去除水。將殘餘物在減壓下濃縮並且添加到己烷中,並且過濾其中的沉澱,從而獲得具有由化學式C表示的重複單元的聚合物(重量平均分子量=約4200)。
將8.04g(0.01mol)比較合成實例2的聚合物、1.35g(0.01mol)己醯氯、2.25g(0.04mol)氫氧化鉀以及42.58g二甲基甲醯胺置於燒瓶中並且在室溫下攪拌。四小時後,反應完成。當反應完成時,使用飽和狀態的氯化銨水溶液和二氯甲烷去除氫氧化鉀。接著,獲得二氯甲烷層並且在減壓下濃縮,接著添加到己烷中。隨後,過濾反應物中的沉澱,從而獲得具有由化學式D表示的重複單元的聚合物(重量平均分子量=約2730)。
[化學式D]
在25℃下,將根據比較合成實例1和比較合成實例2以及合成實例1到合成實例4的每一聚合物溶解於20g乳酸乙酯(ethyllactate,EL)溶劑中,並且檢查溶解於其中的化合物的質量。
隨後,通過使用20g丙二醇單甲基醚乙酸酯(propylene glycolmonomethyl ether acetate,PGMEA)和20g丙二醇單甲基醚(propylene glycolmonomethylether,PGME)代替乳酸乙酯(EL)來重複所述製程。
每一聚合物的溶解度是由在25℃下溶解於20g每一溶劑中的聚合物的質量百分比評估。
溶解度(%)=聚合物質量(g)/溶劑質量(g)
結果提供於表1中。
參照表1,與根據比較合成實例1和比較合成實例2的聚
合物相比,根據合成實例1到合成實例4的聚合物顯示極好的溶解特徵。
將合成實例1的化合物溶解於丙二醇單甲基醚乙酸酯(PGMEA)和環己酮(7:3(v/v))的混合溶劑中並且過濾,從而製備硬罩幕組合物。
除使用合成實例2的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組合物。
除使用合成實例3的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組合物。
除使用合成實例4的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組合物。
除使用比較合成實例1的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組合物。
除使用比較合成實例1的化合物代替合成實例2的化合物以外,根據與實例1相同的方法製備硬罩幕組合物。
將根據實例1到實例4以及比較實例1的每一硬罩幕組
合物(化合物含量:12重量%到15重量%)旋塗於矽晶圓上達到4,000Å厚並且在加熱板上在400℃下熱處理90秒,從而形成薄膜。
隨後,測量薄膜的厚度。接著,通過分別使用CHF3/CF4混合氣體和N2/O2混合氣體對薄膜進行100秒和60秒乾式蝕刻,並且接著再次測量薄膜的厚度。使用乾式蝕刻前後的薄膜厚度和蝕刻時間根據計算方程式1計算主體蝕刻率(bulk etch rate,BER)。
[計算方程式1](初始薄膜厚度-蝕刻後的薄膜厚度)/蝕刻時間(Å/s)
結果提供於表2中。
參照表2,分別由實例1到實例4的硬罩幕組合物形成的薄膜具有關於蝕刻氣體的足夠耐蝕刻性,並且與由根據比較實例1的硬罩幕組合物形成的薄膜相比,顯示改善的主體蝕刻特徵。
將根據實例1到實例4以及比較實例2的硬罩幕組合物(化合物含量:10重量%)分別溶解於乳酸乙酯(EL)中並且儲存於阻擋紫外線(ultraviolet,UV)並且設定在23℃下的清潔室中一個月,通過使用凝膠滲透色譜法(gel permeation chromatography,GPC)研究其在趨勢曲線中的變化。將趨勢曲線中的變化評估為無儲存穩定性(‘X’),而將趨勢曲線中無變化評估為儲存穩定性(‘O’)。
結果提供於表3中。
參照表3,根據實例1到實例4的硬罩幕組合物與根據比較實例2的硬罩幕組合物相比顯示極好的儲存穩定性。
雖然本發明已結合目前視為實用的示例性實施例加以描述,但應瞭解,本發明不限於所公開的實施例,而是相反地希望涵蓋包含在隨附申請專利範圍的精神和範圍內的各種修改和等效配置。
Claims (17)
- 一種聚合物,包含由化學式1表示的部分:
- 如申請專利範圍第1項所述的聚合物,其中所述含氮原子的芳環基團是群組1中列出的化合物中的一個:[群組1]
- 如申請專利範圍第2項所述的聚合物,其中R1、R2以及R3是包含至少三個碳的基團。
- 如申請專利範圍第2項所述的聚合物,其中R1、R2以及R3是由化學式3到化學式6中的一個表示的基團:[化學式3]-(CkH2k+1)
- 如申請專利範圍第4項所述的聚合物,其中在化學式3中,k是3到10的整數。
- 如申請專利範圍第4項所述的聚合物,其中在化學式6中,-(CkH2k+1)是叔丁基。
- 如申請專利範圍第1項所述的聚合物,其中在化學式2中,X1和X2各自獨立地是衍生自群組2中列出的化合物中的一個的單價基團,並且X3是衍生自群組2中列出的化合物中的一個的二價基團:
- 如申請專利範圍第1項所述的聚合物,其中在化學式2中,X1、X2以及X3中的至少一個是衍生自經取代或未經取代的 萘、經取代或未經取代的聯苯、經取代或未經取代的芘、經取代或未經取代的苝、經取代或未經取代的苯並芘、經取代或未經取代的蔻或其組合的基團。
- 如申請專利範圍第1項所述的聚合物,其包括由化學式1-1到化學式1-4中的一個表示的重複單元結構:
- 如申請專利範圍第1項所述的聚合物,其重量平均分子量是1,000到200,000。
- 一種有機層組合物,包括如申請專利範圍第1項所述的聚合物,以及溶劑。
- 如申請專利範圍第11項所述的有機層組合物,其中以所述有機層組合物的總量計,所述聚合物是以0.1重量%到30重量%的量存在。
- 一種形成圖案的方法,包括在基底上提供材料層,在所述材料層上施用如申請專利範圍第11項所述的有機層組合物,熱處理所述有機層組合物以形成硬罩幕層,在所述硬罩幕層上形成含矽薄層,在所述含矽薄層上形成光阻層,將所述光阻層曝光和顯影以形成光阻圖案,使用所述光阻圖案選擇性去除所述含矽薄層以暴露所述材料層的一部分,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,其中所述有機層組合物是使用旋塗法來施用。
- 如申請專利範圍第13項所述的形成圖案的方法,其中所述硬罩幕層是通過在100℃到500℃下熱處理形成。
- 如申請專利範圍第13項所述的形成圖案的方法,還包括在形成所述光阻層之前形成底部抗反射塗層。
- 如申請專利範圍第13項所述的形成圖案的方法,其中所述含矽薄層包括SiCN、SiOC、SiON、SiOCN、SiC、SiN或其組合。
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