TW201403245A - 高密著性阻劑下層膜形成用組成物 - Google Patents
高密著性阻劑下層膜形成用組成物 Download PDFInfo
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- TW201403245A TW201403245A TW102108059A TW102108059A TW201403245A TW 201403245 A TW201403245 A TW 201403245A TW 102108059 A TW102108059 A TW 102108059A TW 102108059 A TW102108059 A TW 102108059A TW 201403245 A TW201403245 A TW 201403245A
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- VTGARNNDLOTBET-UHFFFAOYSA-N gallium antimonide Chemical compound [Sb]#[Ga] VTGARNNDLOTBET-UHFFFAOYSA-N 0.000 description 1
- HZXMRANICFIONG-UHFFFAOYSA-N gallium phosphide Chemical compound [Ga]#P HZXMRANICFIONG-UHFFFAOYSA-N 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000004060 quinone imines Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
〔課題〕提供一種形成使與阻劑之密著性提高之阻劑下層膜用的組成物。〔解決手段〕含有於主鏈具有以下述式(1)所表示之重複結構單元之聚合物及有機溶劑之微影用阻劑下層膜形成組成物。□(式中,R1為表示氫原子或甲基,Q1為以下述式(2)或式(3)所表示之基,v1及v2分別獨立地表示為0或1)。□(式中,R2、R3、R5及R6分別獨立地示表示為氫原子或碳原子數1~4之直鏈狀或分支鏈狀之烴基,R4表示氫原子或甲基,R7表示碳原子數1~6之直鏈狀或分支鏈狀之烴基、碳原子數1~4之烷氧基、碳原子數1~4之烷硫基、鹵素原子、氰基或硝基,w1為表示0~3之整數,w2為表示0~2之整數、x表示0~3之整數)。
Description
本發明係關於在微影步驟中,形成一種為了提高與阻劑間的密著性之阻劑下層膜及於其上方形成所期望之形狀的阻劑圖型之有用的阻劑下層膜之組成物。再者,本發明係關於用該組成物的半導體元件之製作方法。
在ArF液浸微影及超紫外線(EUV)微影中,阻劑線寬度之加工尺寸的微細化為所求。在如此微細的阻劑圖型之形成中,由於隨著阻劑圖型與基底間的接觸面積變小,因長寬比(阻劑的高度/阻劑的線寬度)會變大,有容易發生阻劑圖型崩倒之疑慮。因此,在與阻劑接觸之阻劑下層膜(反射防止膜)中,不使阻劑圖型的崩倒發生之高密著性的阻劑為其所求。
有報告指出,在阻劑下層膜中,為了展現與阻劑間之高密著性,藉由將內酯結構作為阻劑下層膜形成組成物的構成成分來使用,對於所得的阻劑圖型之密著性會提高(專利文獻1)。亦即,藉由使用將含有如內酯結
構之極性部位之結構作為阻劑下層膜形成組成物的構成成分,可提高對阻劑圖型的密著性,也期待能夠防止在微細的阻劑圖型中阻劑圖型的崩倒。
然而,ArF液浸微影,如超紫外線(EUV)微影,在要求更加微細的阻劑圖型之的微影過程中,無法斷言僅將含有內酯結構作為阻劑下層膜形成組成物的構成成分,就能夠防止阻劑圖型的崩倒。
[專利文獻1]國際公開第03/017002號
作為展現與阻劑間的高密著性之手法,可舉例有控制阻劑與阻劑下層膜間的界面化學狀態之方法。亦即,在正型阻劑中,阻劑與阻劑下層膜之界面化學狀態為酸性狀態時,所得之阻劑圖型形狀會成為底切形狀,由於阻劑圖型的接觸面積會極度地降低下,因此容易發生阻劑圖型的崩倒。另一方面,若阻劑與阻劑下層膜之界面化學狀態為鹼性狀態,能夠抑制阻劑圖型形狀成為底切形狀,藉由導入如內酯結構之極性部位,以展現相對於所得之阻劑密著性更加強固的密著性。
本發明之目地係提供一種增大與於阻劑下層
膜上所形成之阻劑圖型的該阻劑下層膜間的密著性,且為了抑制該阻劑圖型的底切形狀,將阻劑下層膜表面狀態變質為鹼性狀態之阻劑下層膜形成組成物。
本發明的第一形態係含有於主鏈上具有以下述式(1)所表示的重複結構單元之聚合物及有機溶劑之微影用阻劑下層膜形成組成物。
以式(1)所表示的重複結構單元為,當Q1係式(2)所表示之基時,以下述式(1’)表示,Q1係式(3)所表示之基時,以下述式(1”)表示。
前述聚合物為更於主鏈上具有以下述式(4)所表示之至少1種(例如、1種、2種或3種)之結構單元也可。
在前述式(4)中,Q2為例如以下述式(5)所表示的二價有機基。
作為本說明書中所記載之烷基,可舉例如甲基、乙基、丙基,作為鹵素原子可舉例如氟原子、氯原子、溴原子、碘原子。作為上述烷氧基可舉例如、甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、sec-丁氧基、tert-丁氧基。作為上述伸烷基可舉例如亞甲基、伸乙基、伸丙基、丁烯基。作為上述伸烯基,可舉例如-CH=CH-基。作為上述脂環式烴環,可舉例如環丙烷環、環丁烷環、環戊烷環、環己烷環。作為上述芳香族烴環,可舉例如苯環、萘環、蒽環。上述二價有機基具有2個伸烷基、脂環式烴環或芳香族烴環時,該2個伸烷基、2個脂環式烴環或2個之芳香族烴環可為介由磺醯基、二硫醚基、硫醚基、羰基、-C(=O)O-基、-O-基、-C(CH3)2-基、-C(CF3)2-基等連結基鍵結。作為後述之烯基,可舉例如烯丙基。
於前述式(4)中,Q2為以下述式(6)所表示的二價有機基也可。
於前述式(4)中,Q2也表示以下述式(9)所示的二價有機基,
(式中,R10示為碳原子數1~6之烷基、碳原子數3~6之烯基、苄基或苯基,前述苯基可經碳原子數1~6之烷基、
鹵素原子、碳原子數1~6之烷氧基、硝基、氰基及碳原子數1~6之烷硫基所成之群中所選出的至少1種所取代)。
本發明之第一形態的阻劑下層膜形成組成物為,更含有交聯劑及交聯觸媒。
本發明的第二形態為,於具有加工對象膜之基板上,塗佈本發明第一形態之阻劑下層膜形成組成物再烘烤形成阻劑下層膜,於前述阻劑下層膜上覆蓋阻劑,對覆蓋有前述阻劑之基板,照射由KrF準分子雷射、ArF準分子雷射、超紫外線及電子線所成之群選出之放射線,之後顯影以形成阻劑圖型,將前述阻劑圖型作為遮罩並藉由乾蝕刻,將前述加工對象膜進行圖型化並製作出半導體元件之方法。
將本發明之阻劑下層膜形成組成物適用在微影過程中,可有效地抑制形成在由該組成物所形成之阻劑
下層膜上之微細的線寬之阻劑圖型的崩倒。
本發明的微影用阻劑下層膜形成組成物為含有於主鏈上具有以tert-丁氧基羰基(以下簡稱Boc基)。所保護之胺基的前述式(1)所表示的重複結構單元之聚合物。該聚合物之重量平均分子量為例如1000~50000。前述式(1)的Q1為前述式(2)所表示時,被Boc基保
護的胺基為和與表示氫原子或甲基之R4鍵結之碳原子鍵結。前述式(1)之Q1為前述式(3)所表示時,被Boc基保護之胺基為與伸苯基鍵結。
作為於主鏈上具有前述式(1)所表示的重複結構單元之聚合物的原料單體,可舉例如具有下述式(10-a)~式(10-h)所表示之被Boc基保護的胺基之化合物。
具有前述式(1)所表示的結構單元及前述式(4)所表示的結構單元之聚合物,可舉例如於末端上具有環氧基之化合物與、具有如與該環氧基反應之羧基的取代基之單體進行反應後所得之。作為如此之單體,可舉例
如以前述式(10-a)~式(10-h)所表示的化合物,亦即,N-(tert-丁氧基羰基)天冬胺酸、N-(tert-丁氧基羰基)麩胺酸、2-N-(tert-丁氧基羰基)胺基已二酸、2-N-(tert-丁氧基羰基)胺基庚二酸、5-N-(tert-丁氧基羰基)胺基異苯二甲酸、6-N-(tert-丁氧基羰基)胺基對苯二甲酸、4-N-(tert-丁氧基羰基)胺基苯二甲酸、5-N-(tert-丁氧基羰基)胺基-2,4,6-三碘異苯二甲酸。此等化合物中較佳為式(10-a)所表示的N-(tert-丁氧基羰基)天冬胺酸。
作為具有前述環氧基之化合物,可例舉如下述式(11-a)~式(11-k)所表示的具有2個環氧基之化合物,
亦即,可舉例如1,4-對苯二甲酸二環氧丙酯、2,6-萘二羧酸二環氧丙酯、1,6-二羥基萘二環氧丙酯、1,2-環己烷二羧酸二環氧丙酯、2,2-雙(4-羥基苯基)丙烷二環氧丙酯、2,2-雙(4-羥基環己烷)丙烷二環氧丙酯、1,4-丁烷二醇二環氧丙酯、單丙烯基異三聚氰酸二環氧丙酯、單甲基異三聚氰酸二環氧丙酯、5,5-二乙基巴比妥酸二環氧丙酯、5,5-二甲基乙內醯脲二環氧丙酯等,但不限定於此等之例。
具有前述式(1)所表示的結構單元及前述式(4)所表示的結構單元之聚合物為,除了具有前述環氧基之化合物,也可使用與具有該環氧基之化合物反應之其他化合物所得之。作為該其他化合物,可舉例如下述式(12-a)~式(12-s)所表示的具有2個羧基、羥基苯基或醯亞胺基之化合物、及酸二酐,
亦即,可舉例如異苯二甲酸、5-羥基異苯二甲酸、2,4-雙羥基安息香酸、2,2-雙(4-羥基苯基)碸丁二酸、琥珀酸、福馬酸、酒石酸、3,3’-雙硫基雙丙酸、1,4-環己烷二羧酸、環丁烷酸二酐、環戊烷酸二酐、單丙烯基異三聚氰酸、5,5-二乙基巴比妥酸、雙乙醇酸、丙酮二羧酸、2,2’-硫基雙乙醇酸、4-羥基安息香酸-4-羥基苯基、2,2-雙(4-羥基苯基)丙烷、2,2-雙(4-羥基苯基)六氟丙烷,但不只限定於此等。
前述式(1)所表示的結構單元及前述式(4)所表示的結構單元之重複數為,例如10以上10000
以下之範圍。
作為具有前述式(1)所表示的結構單元及前述式(4)所表示的結構單元之聚合物,可舉例如下述式(13-a)~式(13-f)之例示,但不限定於此等之例。
具有上述式(13-a)所表示的結構單元之聚合
物為,使用式(10-a)所表示的化合物與、式(11-a)所表示的化合物與、式(12-a)所表示的化合物之原料,使之聚合所得之。具有上述式(13-d)所表示的重複結構單元之聚合物為,使用式(10-b)所表示的化合物與、式(11-a)所表示的化合物與、式(12-c)及式(12-d)所表示的化合物之原料,使之聚合所得之。
式(13-a)、式(13-b)、式(13-c)、式(13-e)及式(13-f)的a所表示的結構單元與b所表示的結構單元與c所表示的結構單元之莫耳比為滿足a:(b+c)=1:1之關係。式(13-d)的a所表示的結構單元與b所表示的結構單元與b’所表示的結構單元與c所表示的結構單元之莫耳比為滿足a:(b+b’+c)=1:1的關係。
在關於式(13-a)、式(13-b)、式(13-c)、式(13-e)及式(13-f)之前述莫耳比a:(b+c)=1:1中,b與c的莫耳比表示為b:c=(1-x):x。在關於式(13-d)之前述莫耳比a:(b+b’+c)=1:1中,b+b’與c的莫耳比表示為(b+b’):c=(1-x):x。但是,莫耳比x為0.01~1,更佳為0.03~0.5。
作為本發明之阻劑下層膜形成組成物中所含之有機溶劑,可舉例如自丙二醇單甲基醚(PGME)、丙二醇單甲基醚乙酸酯(PGMEA)、丙二醇單乙基醚、丙二醇單丙基醚、甲基乙基酮、乳酸乙基酯、環己酮、γ-丁內酯、N-甲基吡咯啶酮、及此等之有機溶劑中所選出2種以上的混合物。且,相對於本發明之阻劑下層膜形成組成
物,有機溶劑的比例為例如50質量%以上99.9質量%以下。
於本發明之阻劑下層膜形成組成物中所含之聚合物,相對於該阻劑下層膜形成組成物為例如0.1質量%~50質量%。
本發明之阻劑下層膜形成組成物除了含有聚合物及有機溶劑之外,含有促進交聯劑、及交聯反應的化合物之交聯觸媒也可。將從本發明之阻劑下層膜形成組成物除去有機溶劑之成分定義為固體成分,此固體成分含有聚合物及、因應必要所添加之交聯劑、交聯觸媒等的添加物。此添加劑的含有比例為,相對於本發明之阻劑下層膜形成組成物的固體成分為例如0.1質量%~50質量%,更佳為1質量%~30質量%。
作為在本發明之阻劑下層膜形成組成物中任意成分之所含有的交聯劑,可舉例如六甲氧基甲基三聚氰胺、四甲氧基甲基苯胍胺、1,3,4,6-四(甲氧基甲基)乙炔脲(POWDERLINK[註冊商標]1174)、1,3,4,6-四(丁氧基甲基)乙炔脲、1,3,4,6-四(羥基甲基)乙炔脲、1,3-雙(羥基甲基)尿素、1,1,3,3-四(丁氧基甲基)尿素及1,1,3,3-四(甲氧基甲基)尿素。使用上述交聯劑時,該交聯劑的含有比例為相對於前述聚合物,可舉例如1質量%~50質量%,較佳為5質量%~30質量%。
作為在本發明之阻劑下層膜形成組成物中任意成分之所含有的交聯觸媒,可舉例如p-甲苯磺酸、三氟
甲烷磺酸、吡啶陽離子-p-甲苯磺酸酯、水楊酸、樟腦磺酸、5-磺酸基水楊酸、4-氯苯磺酸、4-羥基苯磺酸、苯雙磺酸、1-萘磺酸、檸檬酸、安息香酸、羥基安息香酸等的磺酸化合物及羧酸化合物。使用上述交聯觸媒時,該交聯觸媒的含有比例為,相對於前述交聯劑,例如0.1質量%~50質量%,更佳為1質量%~30質量%。
作為本發明之第二形態之半導體元件製作方法中,所使用之基板雖為代表性的矽晶圓,但使用SOI(Silicon on Insulator)基板、或砒化鎵(GaAs)、磷化銦(InP)、磷化鎵(GaP)等之化合物半導體晶片也可。於前述基板上,作為加工對象膜,有形成例如氧化矽膜、含氮之氧化矽膜(SiON膜)、含碳之氧化矽膜(SiOC膜)、含氟之氧化矽膜(SiOF膜)等之絕緣膜。此時,阻劑下層膜為在加工對象膜上被形成。
在製作本發明之半導體元件的方法中,為了在阻劑下層膜上覆蓋阻劑,所使用之阻劑溶液為正型、負型皆可,可以使用在由KrF準分子雷射、ArF準分子雷射、超紫外線及電子線所構成的群中所選出的放射線感光下的化學增幅型阻劑。在前述放射線照射後所進行的顯影中,所使用之顯影液,可舉例使用如四甲基氫氧化銨(TMAH)水溶液之鹼性顯影液。
以下,關於本發明之合成例及實施例,進行具體的說明。但是,本發明不限定於下述合成例及實施例所記載者。
本說明書之下述合成例1~合成例17所表示之聚合物之重量平均分子量為以凝膠透過色譜法(以下,簡稱GPC)所測定之結果。測定為使用TOSOH(股份公司)所製之GPC裝置,測定條件等為如以下所述。
GPC管柱:Shodex[註冊商標].Asahipak[註冊商標](昭和電工(股))
管柱溫度:40℃
溶劑:N,N-二甲基甲醯胺(DMF)
流量:0.6ml/分
標準試料:聚苯乙烯(TOSOH(股))
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))14.00g、異苯二甲酸8.08g、乙基三苯基溴化物0.90g及丙二醇單甲基醚91.94g混合,一邊攪拌一邊進行4小時的加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))23g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))23g,於室溫下進行4小時的離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分
子量為17800。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))5.00g、異苯二甲酸2.60g、N-(tert-丁氧基羰基)-L-天冬胺酸0.41g、乙基三苯基溴化物0.32g及丙二醇單甲基醚33.30g混合,一邊攪拌一邊進行4小時的加熱回流。在所得之的聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))8g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))8g,於室溫進行4小時離子交換處理。GPC分析之結果,所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為13600。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))5.00g、異苯二甲酸2.02g、N-(tert-丁氧基羰基)-L-天冬胺酸1.22g、乙基三苯基溴化物0.32g及丙二醇單甲基醚34.23g混合,一邊攪拌一邊進行4小時的加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))8g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))8g,並在室溫下進行4小時離子交換處理。GPC分析的結果,所得之聚合物溶液以
標準聚苯乙烯換算之重量平均分子量為8000。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))5.00g、異苯二甲酸2.60g、N-(tert-丁氧基羰基)-L-麩胺酸0.43g、乙基三苯基溴化物0.32g及丙二醇單甲基醚33.40g混合,一邊攪拌一邊進行4小時的加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))8g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))8g,在室溫下進行4小時的離子交換處理。GPC分析的結果,所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為16400。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))5.00g、異苯二甲酸2.02g、N-(tert-丁氧基羰基)-L-麩胺酸1.29g、乙基三苯基溴化物0.32g及丙二醇單甲基醚34.53g混合,一邊攪拌一邊進行4小時的加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))8g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))8g,在室溫下進行4小時離子交換處理。GPC分析的結果,所得之聚合物溶液以標
準聚苯乙烯換算之重量平均分子量為13900。
在5-胺基異苯二甲酸5.00g中,添加將1,4-二噁烷80mL及氫氧化鈉2.21g溶解之水溶液80mL後,加入二(tert-丁基)二碳酸酯9.04g,於室溫下攪拌19小時。於反應液中添加飽和檸檬酸水溶液至成酸性,將析出固體過濾。藉由將過濾物減壓乾燥,而得回收率90%之5-(tert-丁氧基羰基)胺基異苯二甲酸7.01g。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))5.00g、異苯二甲酸2.60g、合成例6所得之5-(tert-丁氧基羰基)胺基異苯二甲酸0.49g、乙基三苯基溴化物0.32g及丙二醇單甲基醚33.63g混合,一邊攪拌一邊進行4小時的加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))8g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))8g,於室溫下進行4小時的離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為18000。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))5.00g、異苯二甲酸2.02g、5-(tert-丁氧基羰基)胺基異苯二甲酸1.47g、乙基三苯基溴化物0.32g及丙二醇單甲基醚35.23g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))8g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))8g,於室溫下進行4小時離子交換處理。GPC分析之結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為17900。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))12.00g、2,4-二羥基安息香酸3.21g、雙(4-羥基苯基)碸5.22g、乙基三苯基溴化物0.77g及丙二醇單甲基醚84.82g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))22g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))22g,於室溫下進行4小時離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為5500。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))6.00g、2,4-雙羥基安息香酸1.45g、雙(4-羥基苯基)碸2.35g、N-(tert-丁氧基羰基)-L-麩胺酸0.52g、乙基三苯基溴化物0.39g及丙二醇單甲基醚42.78g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))11g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))11g,於室溫下進行4小時離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為4500。
將1,4-對苯二甲酸二環氧丙酯(製品名:EX-711[註冊商標]、nagasechemtex(股))6.00g、2,4-雙羥基安息香酸1.12g、雙(4-羥基苯基)碸1.83g、N-(tert-丁氧基羰基)-L-麩胺酸1.55g、乙基三苯基溴化物0.39g及丙二醇單甲基醚43.54g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))11g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))11g,於室溫下進行4小時離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為3200。
將單丙烯基二縮水甘油異三聚氰酸(製品名:MA-DGIC[註冊商標]、四國化成工業(股))13.00g、5,5-二乙基巴比妥酸8.65g、苄基三乙基氯化銨0.53g及丙二醇單甲基醚88.72g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))22g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))22g,於室溫下進行4小時離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為8000。
將單丙烯基二縮水甘油異三聚氰酸(製品名:MA-DGIC[註冊商標]、四國化成工業(股))7.00g、5,5-二乙基巴比妥酸4.19g、N-(tert-丁氧基羰基)-L-天冬胺酸0.59g、乙基三苯基溴化物0.47g及丙二醇單甲基醚48.99g混合,一邊攪拌一邊進行4小時加熱回流。於所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))12g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))12g,於室溫下進行4小時離子交換處理。GPC分析的結果,所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為
7600。
將單丙烯基二縮水甘油異三聚氰酸(製品名:MA-DGIC[註冊商標]、四國化成工業(股))7.00g、5,5-二乙基巴比妥酸3.26g、N-(tert-丁氧基羰基)-L-天冬胺酸1.77g、乙基三苯基溴化物0.47g及丙二醇單甲基醚49.98g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))12g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))12g,於室溫下進行4小時離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為4200。
將單丙烯基二縮水甘油異三聚氰酸(製品名:MA-DGIC[註冊商標]、四國化成工業(股))6.00g、1,2,3,4-環丁烷四羧酸二酐4.25g、苄基三乙基氯化銨0.25g及丙二醇單甲基醚41.98g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))10g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))10g,於室溫下進行4小時離子交換處理。
GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為10000。
將單丙烯基二縮水甘油異三聚氰酸(製品名:MA-DGIC[註冊商標]、四國化成工業(股))6.00g、1,2,3,4-環丁烷四羧酸二酐3.82g、N-(tert-丁氧基羰基)-L-麩胺酸0.54g、乙基三苯基溴化物0.40g及丙二醇單甲基醚43.04g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))11g及陰離子交換樹脂(製品名:安百來[註冊商標]15JWET、organo(股))11g,於室溫下進行4小時離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為18900。
將單丙烯基二縮水甘油異三聚氰酸(製品名:MA-DGIC[註冊商標]、四國化成工業(股))6.00g、1,2,3,4-環丁烷四羧酸二酐2.97g、N-(tert-丁氧基羰基)-L-麩胺酸1.61g、乙基三苯基溴化物0.40g及丙二醇單甲基醚43.93g混合,一邊攪拌一邊進行4小時加熱回流。在所得之聚合物溶液中,加入陽離子交換樹脂(製品名:DOWEXTM[註冊商標]550A、murotec(股))11g及陰離子交換樹脂(製
品名:安百來[註冊商標]15JWET、organo(股))11g,於室溫下進行4小時離子交換處理。GPC分析的結果所得之聚合物溶液以標準聚苯乙烯換算之重量平均分子量為13200。
藉由將上述合成例2所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚44.20g及丙二醇單乙基醚5.14g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例3所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚40.39g及丙二醇單乙基醚4.72g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例4所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商
標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚44.34g及丙二醇單乙基醚5.16g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例5所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚42.77g及丙二醇單乙基醚4.99g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例7所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚44.54g及丙二醇單乙基醚5.18g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例8所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商
標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚43.40g及丙二醇單乙基醚5.06g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例10所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.11g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚36.44g及丙二醇單甲基醚乙酸酯16.50g進行混合,以調製阻劑下層膜形成組成物調製。
藉由將上述合成例11所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚34.40g及丙二醇單甲基醚乙酸酯15.64g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例13所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商
標]1174、日本Nihon Cytec Industries Inc.(股)製)0.11g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚35.50g及丙二醇單甲基醚乙酸酯16.10g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例14所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.11g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚35.05g及丙二醇單甲基醚乙酸酯15.91g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例16所得之聚合物溶液2.00g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.11g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚37.73g及丙二醇單甲基醚乙酸酯16.84g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例17所得之聚合物溶液2.00g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商
標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚34.62g及丙二醇單甲基醚乙酸酯15.52g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例1所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.11g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚46.21g及丙二醇單乙基醚5.36g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例9所得之聚合物溶液2.00g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.10g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚32.72g及丙二醇單甲基醚乙酸酯14.72g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例12所得之聚合物溶液2.50g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商
標]1174、日本Nihon Cytec Industries Inc.(股)製)0.11g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚35.70g及丙二醇單甲基醚乙酸酯16.19g進行混合,以調製阻劑下層膜形成組成物。
藉由將上述合成例15所得之聚合物溶液2.00g、四甲氧基甲基乙炔脲(製品名:POWDERLINK[註冊商標]1174、日本Nihon Cytec Industries Inc.(股)製)0.12g、5-磺酸基水楊酸0.01g、丙二醇單甲基醚40.34g及丙二醇單甲基醚乙酸酯17.94g進行混合,以調製阻劑下層膜形成組成物。
於含氮之氧化矽膜(SiON)被氣相蒸鍍(膜厚31.5nm)之矽晶圓上,將由本說明書之實施例1~實施例12、及比較例1~比較例4所調製之各阻劑下層膜形成組成物控制膜厚在10nm,藉由於205℃加熱60秒,形成阻劑下層膜。於此阻劑下層膜上,將ArF準分子雷射用正型阻劑溶液(JSR(股)製、製品名:AR2772JN)旋塗,進行於110℃下90秒的加熱,使用ArF準分子雷射用曝光裝置((股)nikon製、NSR-S307E),以特定的條件曝光。曝光後,於110℃下進行90秒的加熱(PEB),於冷卻盤上冷卻至室溫,處理顯影及水洗處理,以形成阻劑圖型。
將目的之線寬調整為80nm線與間隔(線為80nm、間隔為100nm),為了檢討於最適當之焦距時的曝光量變化與阻劑圖型崩倒之關係,將阻劑圖型不發生崩倒之最高曝光量(臨界曝光量)與此時之阻劑圖型尺寸(圖型崩倒之臨界尺寸)以測長SEM進行確認。因此,藉由使用本發明之阻劑下層膜形成組成物,可以防止高曝光量領域中阻劑圖型的崩倒,能夠確認是否能形成微細的阻劑圖型。又,將在目的線寬之80nm線與間隔中阻劑圖型的剖面形狀,以斷面SEM進行確認。因此,藉由使用本發明之阻劑下層膜形成組成物,能夠判斷由阻劑圖型崩倒之原因所造成的阻劑形狀。
所得之阻劑圖型的臨界曝光量與圖型崩倒臨界尺寸、阻劑圖型的剖面形狀之結果表示於下述表1~表4。此臨界曝光量之值越大,圖型崩倒臨界尺寸之值越小,越不容易發生阻劑圖型的崩倒,並能夠完成阻劑下層膜與阻劑間的高密著性。
由表1所示,使用實施例1~實施例6之阻劑下層膜形成組成物來形成阻劑下層膜時,比使用比較例1之阻劑下層膜形成組成物來形成阻劑下層膜時,其臨界曝光量更高,由於且圖型崩倒臨界尺寸變小,形成微細的阻劑圖型時,能夠防止阻劑圖型之崩倒。又,使用實施例1~實施例6之阻劑下層膜形成組成物來形成阻劑下層膜時,所得之阻劑圖型的剖面形狀為楔形形狀(台形形
狀)。另一方面,使用比較例1之阻劑下層膜形成組成物來形成阻劑下層膜時為底切形狀。阻劑圖型與阻劑下層膜之接觸面積增大之楔形形狀能夠防止阻劑圖型的崩倒。同樣的,如表2~表4所示,分別比較實施例7及實施例8與比較例2、實施例9及實施例10與比較例3、實施例11及實施例12與比較例4後,不管使用哪個實施例所示之阻劑下層膜形成組成物來形成阻劑下層膜,比使用比較例示所阻劑下層膜形成組成物來形成阻劑下層膜,其臨界曝光量更高,且也顯示圖型崩倒臨界尺寸變小。亦即,實施例1~實施例12之阻劑下層膜形成組成物為了防止阻劑圖型崩倒,顯示其有用之效果。
以上,雖將本發明之實施形態進行說明,但本發明之技術的範圍並不限定於上述實施形態所記載之範圍。於上述實施形態中,能夠增加多樣的變更或改良。
Claims (7)
- 一種微影用阻劑下層膜形成組成物,其係包含於主鏈具有下述式(1)所示的重複結構單元之聚合物及有機溶劑,
- 如請求項1之微影用阻劑下層膜形成組成物,其中前述聚合物係進一步於主鏈具有下述式(4)所示的至少1種的結構單元,
- 如請求項2之微影用阻劑下層膜形成組成物,其中前述式(4)中,Q2示為下述式(5)所示的二價有機基,
- 如請求項2之微影用阻劑下層膜形成組成物,其中前述式(4)中,Q2示為下述式(6)所示的二價有機基,
- 如請求項2之微影用阻劑下層膜形成組成物,其中前述式(4)中,Q2示為下述式(9)所示的二價有機基,
- 如請求項1~請求項5中任一項之微影用阻劑下層膜形成組成物,其係進一步包含交聯劑及交聯觸媒。
- 一種製作半導體元件之方法,其係將如請求項1~請求項6中任一項之阻劑下層膜形成組成物塗佈於具有加工對象膜之基板上,烘烤而形成阻劑下層膜,將阻劑被覆於前述阻劑下層膜上,對以前述阻劑所被覆之基板照射由 KrF準分子雷射、ArF準分子雷射、超紫外線及電子線所成之群選出之放射線,之後顯影而形成阻劑圖型,將前述阻劑圖型作為遮罩,藉由乾蝕刻而使前述加工對象膜圖型化。
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KR102374269B1 (ko) * | 2016-03-09 | 2022-03-15 | 닛산 가가쿠 가부시키가이샤 | 레지스트 하층막 형성 조성물 및 이것을 이용한 레지스트 패턴의 형성방법 |
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