TW202238275A - 阻劑下層膜形成組成物 - Google Patents
阻劑下層膜形成組成物 Download PDFInfo
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- TW202238275A TW202238275A TW110147243A TW110147243A TW202238275A TW 202238275 A TW202238275 A TW 202238275A TW 110147243 A TW110147243 A TW 110147243A TW 110147243 A TW110147243 A TW 110147243A TW 202238275 A TW202238275 A TW 202238275A
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- 229960001826 dimethylphthalate Drugs 0.000 description 1
- PQJYOOFQDXGDDS-ZCXUNETKSA-N dinonyl (z)-but-2-enedioate Chemical compound CCCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCCC PQJYOOFQDXGDDS-ZCXUNETKSA-N 0.000 description 1
- ORPDKMPYOLFUBA-UHFFFAOYSA-M diphenyliodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ORPDKMPYOLFUBA-UHFFFAOYSA-M 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
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- 238000000609 electron-beam lithography Methods 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
- MEEWSBNOBXBASQ-UHFFFAOYSA-M fluoromethanesulfonate Chemical compound [O-]S(=O)(=O)[CH]F MEEWSBNOBXBASQ-UHFFFAOYSA-M 0.000 description 1
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- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000004811 liquid chromatography Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- LHEOFIBQZSRTNC-UHFFFAOYSA-N phenanthrene-3-carbaldehyde Chemical compound C1=CC=C2C3=CC(C=O)=CC=C3C=CC2=C1 LHEOFIBQZSRTNC-UHFFFAOYSA-N 0.000 description 1
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- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
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- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
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- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 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
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- 238000004528 spin coating Methods 0.000 description 1
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- TVJIJCPNBAPRRJ-UHFFFAOYSA-N trichlorosilylmethanol Chemical compound OC[Si](Cl)(Cl)Cl TVJIJCPNBAPRRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 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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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0395—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having a backbone with alicyclic moieties
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- 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
- C08G10/00—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08G10/02—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only of aldehydes
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- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
-
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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Abstract
Description
本發明為關於一種能夠形成埋入特性優異,表示良好之乾蝕刻速度比及光學定數,亦即對段差基板之被覆性亦良好,且平坦並進而具有優異之硬度之阻劑下層膜之阻劑下層膜形成組成物、使用該阻劑下層膜形成組成物之阻劑下層膜,以及半導體裝置之製造方法。
近年來,多層阻劑製程用之阻劑下層膜材料尤其是被要求對短波長之曝光作為反射防止膜之機能,且具有適當光學定數的同時,也一併具備基板加工之蝕刻耐性,故有提案利用具有包含苯環之重複單位之聚合物(專利文獻1)。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開2004-354554
[本發明欲解決之課題]
伴隨阻劑圖型之微細化,為了所求之阻劑層之薄膜化,已熟知一種微影製程,其係至少形成2層阻劑下層膜,將該阻劑下層膜作為光罩材來使用。這是一種在半導體基板上設置至少一層有機膜(下層有機膜),與至少一層無機下層膜,並將形成在上層阻劑膜之阻劑圖型作為光罩,將無機下層膜進行圖型化,將該圖型作為光罩,進行下層有機膜之圖型化之方法,且能夠形成高長寬比之圖型。作為形成前述至少2層之材料,有舉出有機樹脂(例如丙烯酸樹脂、酚醛清漆樹脂),與無機系材料(矽樹脂(例如有機聚矽氧烷)、無機矽化合物(例如SiON、SiO
2)等)之組合。進而,近年來,為了得到1個圖型,廣泛適用進行2次微影與2次蝕刻之雙重圖型化技術,在各自步驟中,有使用上述多層製程。此時,最初之圖型形成後,成膜之有機膜必須要有將段差平坦化之特性。
然而,會有形成在被加工基板上之阻劑圖型具有高低差或疏密,亦即對段差基板,阻劑下層膜形成用組成物之被覆性較低,埋入後之膜厚差會變大,且難以形成平坦之膜之問題。
本發明係基於如此之課題解決,欲提供一種能夠形成表示較高蝕刻耐性、良好之乾蝕刻速度比及光學定數,亦即對段差基板之被覆性亦良好,且埋入後之膜厚差較小,平坦並進而具有優異之硬度之膜之阻劑下層膜形成組成物。且,本發明之目的為提供一種使用該阻劑下層膜形成組成物之阻劑下層膜,以及半導體裝置之製造方法。
[解決課題之手段]
本發明包含以下。
[1] 一種阻劑下層膜形成組成物,包含下述式(1)或式(2)表示之化合物與下述式(3)表示之化合物之反應生成物,及溶劑。
(式(1)或式(2)中,Ar
1、Ar
2各自獨立為亦可經R
1、R
2取代之苯環或萘環,R
1及R
2各自獨立為氫原子、鹵原子、硝基、胺基、羥基、碳數1至10之烷基、碳數2至10之烯基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合,R
3為氫原子、碳數1至10之烷基、碳數2至10之烯基、碳數2至10之炔基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合,n
1及n
2在Ar
1、Ar
2為苯環時,各自為1至3之整數,在Ar
1、Ar
2為萘環時,各自為1至5之整數,
式(3)中,X為單鍵結、碳數1至30之亦可包含氮原子、氧原子、硫原子之飽和或者不飽和之直鏈或環狀之有機基,或碳數6至30之伸芳基。)
[2] 如[1]之阻劑下層膜形成組成物,其中,式(1)或式(2)中,Ar
1及Ar
2為苯環。
[3] 如[1]或[2]之阻劑下層膜形成組成物,其中,式(1)中,R
1、R
2各自為氫原子。
[4] 如[1]至[3]中任1項之阻劑下層膜形成組成物,其中,式(3)中,X為單鍵結,或碳數1至30之亦可包含氮原子之飽和或者不飽和之直鏈或環狀之有機基。
[5] 如[1]至[3]中任1項之阻劑下層膜形成組成物,其中,式(3)中,X為單鍵結。
[6] 如[1]至[5]中任1項之阻劑下層膜形成組成物,其中,包含2種類以上前述式(1)或式(2)表示之化合物與前述式(3)表示之化合物之反應生成物。
[7] 如[1]至[5]中任1項之阻劑下層膜形成組成物,其中,包含前述式(1)或式(2)表示之化合物,進而為前述式(1)或式(2)表示之化合物以外之其他芳香族化合物與前述式(3)表示之化合物之反應生成物。
[8] 如[1]至[7]中任1項之阻劑下層膜形成組成物,其中,進而包含交聯劑。
[9] 如[1]至[8]中任1項之阻劑下層膜形成組成物,其中,進而包含酸及/或酸產生劑。
[10] 如[1]至[9]中任1項之阻劑下層膜形成組成物,其中,前述溶劑之沸點為160℃以上。
[11] 一種阻劑下層膜,其係包含如[1]至[10]中任1項之阻劑下層膜形成組成物之塗布膜之燒成物。
[12] 一種半導體裝置之製造方法,其係包含:
在半導體基板上使用如[1]至[10]中任1項之阻劑下層膜形成組成物,形成阻劑下層膜之步驟、
在所形成之阻劑下層膜上形成阻劑膜之步驟、
對所形成之阻劑膜,藉由光或電子線之照射與顯像,形成阻劑圖型之步驟、
介隔著所形成之阻劑圖型,將前述阻劑下層膜蝕刻並圖型化之步驟,及
介隔著經圖型化之阻劑下層膜,加工半導體基板之步驟。
[發明效果]
本發明之阻劑下層膜形成組成物不僅形成具有高蝕刻耐性、良好之乾蝕刻速度比及光學定數之膜,所得之阻劑下層膜,亦即對段差基板之被覆性亦良好,且埋入後之膜厚差較小,平坦並進而具有優異之硬度之膜,達到更微細之基板加工。
尤其是本發明之阻劑下層膜形成組成物,對於至少形成2層以阻劑膜厚之薄膜化為目的之阻劑下層膜,並將該阻劑下層膜作為蝕刻光罩使用之微影製程為有效。
[阻劑下層膜形成組成物]
本發明相關之阻劑下層膜形成組成物包含下述式(1)或式(2)表示之化合物與下述式(3)表示之化合物之反應生成物,及溶劑。
(式(1)或式(2)中,Ar
1、Ar
2各自獨立為亦可經R
1、R
2取代之苯環或萘環,R
1及R
2各自獨立為氫原子、鹵原子、硝基、胺基、羥基、碳數1至10之烷基、碳數2至10之烯基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合,R
3為氫原子、碳數1至10之烷基、碳數2至10之烯基、碳數2至10之炔基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合,n
1及n
2在Ar
1、Ar
2為苯環時,各自為1至3之整數,在Ar
1、Ar
2為萘環時,各自為1至5之整數,
式(3)中,X表示單鍵結、碳數1至30之亦可包含氮原子、氧原子、硫原子之飽和或不飽和之直鏈或環狀之有機基,或碳數6至30之伸芳基)。
前述式(1)或式(2)表示之化合物能夠使用2種類以上。以下依序來說明。
[式(1)、式(2)表示之化合物]
上述式(1)或式(2)中,Ar
1、Ar
2各自獨立為亦可經R
1、R
2取代之苯環或萘環,R
1及R
2各自獨立為氫原子、鹵原子、硝基、胺基、羥基、碳數1至10之烷基、碳數2至10之烯基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合,R
3為氫原子、碳數1~10之烷基、碳數2至10之烯基、碳數2至10之炔基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合。n
1及n
2在Ar
1、Ar
2為苯環時,各自為1至3之整數,在Ar
1、Ar
2為萘環時,各自為1至5之整數。
作為上述鹵原子,有舉出氟原子、氯原子、溴原子、碘原子。
作為上述碳原子數1至10之烷基,有舉出甲基、乙基、n-丙基、i-丙基、環丙基、n-丁基、i-丁基、s-丁基、t-丁基、環丁基、1-甲基-環丙基、2-甲基-環丙基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、環戊基、1-甲基-環丁基、2-甲基-環丁基、3-甲基-環丁基、1,2-二甲基-環丙基、2,3-二甲基-環丙基、1-乙基-環丙基、2-乙基-環丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基、1-乙基-2-甲基-n-丙基、環己基、1-甲基-環戊基、2-甲基-環戊基、3-甲基-環戊基、1-乙基-環丁基、2-乙基-環丁基、3-乙基-環丁基、1,2-二甲基-環丁基、1,3-二甲基-環丁基、2,2-二甲基-環丁基、2,3-二甲基-環丁基、2,4-二甲基-環丁基、3,3-二甲基-環丁基、1-n-丙基-環丙基、2-n-丙基-環丙基、1-i-丙基-環丙基、2-i-丙基-環丙基、1,2,2-三甲基-環丙基、1,2,3-三甲基-環丙基、2,2,3-三甲基-環丙基、1-乙基-2-甲基-環丙基、2-乙基-1-甲基-環丙基、2-乙基-2-甲基-環丙基及2-乙基-3-甲基-環丙基等。
作為上述碳原子數2至10之烯基,有舉出乙烯基、1-丙烯基、2-丙烯基、1-甲基-1-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-n-丙基乙烯基、1-甲基-1-丁烯基、1-甲基-2-丁烯基、1-甲基-3-丁烯基、2-乙基-2-丙烯基、2-甲基-1-丁烯基、2-甲基-2-丁烯基、2-甲基-3-丁烯基、3-甲基-1-丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1-i-丙基乙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-環戊烯基、2-環戊烯基、3-環戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、1-甲基-2-戊烯基、1-甲基-3-戊烯基、1-甲基-4-戊烯基、1-n-丁基乙烯基、2-甲基-1-戊烯基、2-甲基-2-戊烯基、2-甲基-3-戊烯基、2-甲基-4-戊烯基、2-n-丙基-2-丙烯基、3-甲基-1-戊烯基、3-甲基-2-戊烯基、3-甲基-3-戊烯基、3-甲基-4-戊烯基、3-乙基-3-丁烯基、4-甲基-1-戊烯基、4-甲基-2-戊烯基、4-甲基-3-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1-甲基-2-乙基-2-丙烯基、1-s-丁基乙烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、1-i-丁基乙烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、2-i-丙基-2-丙烯基、3,3-二甲基-1-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、1-n-丙基-1-丙烯基、1-n-丙基-2-丙烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-t-丁基乙烯基、1-甲基-1-乙基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基、1-i-丙基-1-丙烯基、1-i-丙基-2-丙烯基、1-甲基-2-環戊烯基、1-甲基-3-環戊烯基、2-甲基-1-環戊烯基、2-甲基-2-環戊烯基、2-甲基-3-環戊烯基、2-甲基-4-環戊烯基、2-甲基-5-環戊烯基、2-亞甲基-環戊基、3-甲基-1-環戊烯基、3-甲基-2-環戊烯基、3-甲基-3-環戊烯基、3-甲基-4-環戊烯基、3-甲基-5-環戊烯基、3-亞甲基-環戊基、1-環己烯基、2-環己烯基及3-環己烯基等。
作為上述碳原子數6至40之芳基,有舉出苯基、o-甲基苯基、m-甲基苯基、p-甲基苯基、o-氯苯基、m-氯苯基、p-氯苯基、o-氟苯基、p-氟苯基、o-甲氧基苯基、p-甲氧基苯基、p-硝基苯基、p-氰基苯基、α-萘基、β-萘基、o-雙苯基、m-雙苯基、p-雙苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基及9-菲基。
作為碳數2至10之炔基,有舉出乙炔基、1-丙炔基、1-丁炔基、1-甲基-3-戊炔基、1-甲基-3-己炔基、2-甲基-3-己炔基等。
作為本發明之聚合物製造中所使用之上述式(1)表示之咔唑類,有舉例如咔唑、N-甲基咔唑、N-乙基咔唑、1,3,6,8-四硝基咔唑、3,6-二胺基咔唑、3,6-二溴-9-乙基咔唑、3,6-二溴-9-苯基咔唑、3,6-二溴咔唑、3,6-二氯咔唑、3-胺基-9-乙基咔唑、3-溴-9-乙基咔唑、4,4'雙(9H-咔唑-9-基)雙苯基、9-乙基咔唑、4-環氧丙基咔唑、4-羥基咔唑、9-(1H-苯并三吡咯-1-基甲基)-9H-咔唑、9-乙醯基-3,6-二碘咔唑、9-苯并基咔唑、9-苯并基咔唑-6-二羧基醛、9-芐基咔唑-3-羧基醛、9-甲基咔唑、9-苯基咔唑、9-乙烯咔唑、咔唑鉀、咔唑-N-氯化羰、N-乙基咔唑-3-羧基醛、N-((9-乙基咔唑-3-基)亞甲基)-2-甲基-1-吲哚啉基胺等。此等能夠單獨使用,亦可組合2種以上來使用。
上述一般式(3)表示之二醛化合物之一例能夠由以下式表示。
較佳之式(3)表示之二醛化合物為X表示單鍵結或碳數1至30之亦可包含氮原子之飽和或者不飽和之直鏈或環狀之有機基之二醛化合物。特別佳為X為單鍵結之二醛化合物。
此等之二醛化合物由於能夠容易取得,能夠抑制所得之阻劑下層膜組成物之製造成本。
進而,亦能夠使用於此所示之二醛化合物之等價物。例如,作為上述一般式(3)之等價物,下述一般式
(X與前述X相同定義,R'為亦可各自相同或相異之碳數1~10之一價烴基),
(X與前述X相同定義,R"為碳數1~10之二價烴基),
或甲醯基之α-碳原子有鍵結氫原子時,為
(X'為比前述X少1個氫原子之有機基,R'為碳數1~10之一價烴基)等。
式(1)或式(2)之化合物與式(3)之二醛化合物之比率,相對於式(1)或式(2)之化合物1莫耳,為0.01~5莫耳較佳,再較佳為0.1~2莫耳。
本發明之阻劑下層膜材料亦可含有將上述式(1)或式(2)表示之1種類或2種類以上之化合物,與上述一般式(3)表示之1種以上之化合物及/或其等價物縮合所得之聚合物。
[其他芳香族化合物]
本發明之阻劑下層膜材料在不損害本發明之效果之範圍,能夠添加上述式(1)或式(2)表示之化合物以外之芳香族化合物作為第三成分,亦能夠與上述式(3)表示之化合物縮合。
作為如此之芳香族化合物之例,有舉出酚類、萘酚類、雙酚類、多元酚類等。
[反應生成物]
將上述式(1)或式(2)表示之化合物,與因應必要之上述其他芳香族化合物與上述式(3)表示之化合物縮合之聚合物會成為反應生成物。且,如上述,上述式(1)或式(2)表示之化合物及上述其他芳香族化合物能夠選擇採用1種或2種以上,因此上述聚合物亦能夠為多元共聚合物。
且,上述式(1)或式(2)表示之化合物與上述式(3)表示之化合物以外之單體,亦可以不損害本發明之效果之範圍之量(例如未滿50莫耳%,未滿30莫耳%,未滿20莫耳%,未滿10莫耳%,或未滿5莫耳%)使其共聚合。
作為反應中使用之酸觸媒,有使用例如硫酸、磷酸、過氯酸等之礦酸類、p-甲苯磺酸、p-甲苯磺酸一水和物、甲磺酸等之有機磺酸類、蟻酸、草酸等之羧酸類。酸觸媒之使用量會因使用之酸類之種類來進行各種選擇。通常,相對於上述式(1)或式(2)表示之化合物100質量份,為0.001至10000質量份,較佳為0.01至1000質量份,再較佳為0.1至100質量份。
上述縮合反應與加成反應在無溶媒中也能夠進行,但通常使用溶媒來進行。作為溶媒,只要不阻礙反應者,全部都能夠使用。有舉例如1,2-二甲氧基乙烷、二乙二醇二甲基醚、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、四氫呋喃、二氧雜環等之醚類。
反應時,因應必要,亦可添加聚合禁止劑(自由基捕集劑)。作為聚合起始劑之具體例,有舉出2,6-二異丁基酚、3,5-二-tert-丁基酚、3,5-二-tert-丁基甲酚、氫醌、氫醌單甲基醚、鄰苯三酚、tert-丁基兒茶酚、4-甲氧基-1-萘酚等。添加聚合禁止劑時,其添加量相對於全固形分,為1質量%以下較佳。
反應溫度通常為40℃至200℃。反應時間因應反應溫度而進行各種選擇,但通常為30分鐘至50小時左右。
如以上所得之聚合物之重量平均分子量Mw通常為500至1,000,000,或為600至500,000。
本發明中,關於適合使用之反應生成物,以實施例來說明。
[溶劑]
作為本發明相關之阻劑下層膜形成組成物之溶劑,只要是能夠溶解上述反應生成物之溶劑即可,能夠無特別限制地來使用。尤其是,本發明相關之阻劑下層膜形成組成物是以均勻的溶液狀態來使用,因此若考慮其塗布性能,推薦與微影步驟中一般所使用之溶劑來併用。
作為如此之溶劑,能夠舉例如甲基賽路蘇乙酸酯、乙基賽路蘇乙酸酯、丙二醇、丙二醇單甲基醚、丙二醇單乙基醚、甲基異丁基甲醇、丙二醇單丁基醚、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、丙二醇單丁基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯、丙酮酸甲酯、丙酮酸乙酯、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚、乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、乙二醇單丙基醚乙酸酯、乙二醇單丁基醚乙酸酯、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二丙基醚、二乙二醇二丁基醚、丙二醇二甲基醚、丙二醇二乙基醚、丙二醇二丙基醚、丙二醇二丁基醚、乳酸乙酯、乳酸丙酯、乳酸異丙酯、乳酸丁酯、乳酸異丁酯、甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸異丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊酯、甲酸異戊酯、乙酸甲酯、乙酸乙酯、乙酸戊酯、乙酸異戊酯、乙酸己基、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、丙酸丁酯、丙酸異丁酯、酪酸甲酯、酪酸乙酯、酪酸丙酯、酪酸異丙酯、酪酸丁酯、酪酸異丁酯、羥基乙酸乙酯、2-羥基-2-甲基丙酸乙酯、3-甲氧基-2-甲基丙酸甲酯、2-羥基-3-甲基酪酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲氧基丙基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基丙酸酯、3-甲基-3-甲氧基丁基丁酸酯、乙醯乙酸甲酯、甲苯、二甲苯、甲基乙基酮、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、N,N-二甲基甲醯胺、N-甲基乙醯醯胺、N,N-二甲基乙醯醯胺、N-甲基吡咯烷酮、4-甲基-2-戊醇及γ-丁內酯等。此等之溶劑亦可單獨或組合二種以上來使用。
且,亦能夠使用WO2018/131562A1中記載之下述化合物。
(式(i)中之R
4、R
5及R
6各自表示亦可經氫原子、氧原子、硫原子或醯胺鍵結中斷之碳原子數1至20之烷基,亦可互相相同或相異,且亦可互相鍵結形成環構造)。
作為碳原子數1至20之烷基,有舉出亦可具有或不具有取代基之直鏈或具有分支之烷基,有舉例如甲基、乙基、n-丙基、異丙基、n-丁基、sec-丁基、tert-丁基、n-戊基、異戊基、新戊基、n-己基、異己基、n-庚基、n-辛基、環己基、2-乙基己基、n-壬基、異壬基、p-tert-丁基環己基、n-癸基、n-十二基壬基、十一基、十二基、十三基、十四基、十五基、十六基、十七基、十八基、十九基及二十基等。較佳為碳原子數1至12之烷基,再較佳為碳原子數1至8之烷基,更較佳為碳原子數1至4之烷基。
作為經氧原子、硫原子或醯胺鍵結中斷之碳原子數1至20之烷基,有舉例如含有構造單位-CH
2-O-、
-CH
2-S-、-CH
2-NHCO-或-CH
2-CONH-者。-O-、-S-、
-NHCO-或-CONH-在前述烷基中亦可為一單位或二單位以上。經-O-、-S-、-NHCO-或-CONH-單位中斷之碳原子數1至20之烷基之具體例,為甲氧基、乙氧基、丙氧基、丁氧基、甲基硫基、乙基硫基、丙基硫基、丁基硫基、甲基羰基胺基、乙基羰基胺基、丙基羰基胺基、丁基羰基胺基、甲基胺基羰基、乙基胺基羰基、丙基胺基羰基、丁基胺基羰基等,進而亦可為甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二基或十八基,其各自經甲氧基、乙氧基、丙氧基、丁氧基、甲基硫基、乙基硫基、丙基硫基、丁基硫基、甲基羰基胺基、乙基羰基胺基、甲基胺基羰基、乙基胺基羰基等取代。較佳為甲氧基、乙氧基、甲基硫基、乙基硫基,再較佳為甲氧基、乙氧基。
此等之溶劑為比較高之沸點,故阻劑下層膜形成組成物用於賦予高埋入性或高平坦化性較有效。
此等之溶劑能夠以單獨或組合二種以上來使用。此等之溶劑中,沸點為160℃以上者較佳,為丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、乳酸乙酯、乳酸丁酯、環己酮、3-甲氧基-N,N-二甲基丙醯胺、N,N-二甲基異丁基醯胺、2,5-二甲基己烷-1,6-二基二乙酸酯(DAH;cas,89182-68-3)及1,6-二乙醯氧基己烷(cas,6222-17-9)等較佳。尤其是為丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、N,N-二甲基異丁基醯胺較佳。
[交聯劑成分]
本發明之阻劑下層膜形成組成物能夠包含交聯劑成分。作為其交聯劑,有舉出三聚氰胺系、取代尿素系,或此等之聚合物系等。較佳為具有至少2個交聯形成取代基之交聯劑,為甲氧基甲基化乙炔脲(例如四甲氧基甲基乙炔脲)、丁氧甲基化乙炔脲、甲氧基甲基化三聚氰胺、丁氧甲基化三聚氰胺、甲氧基甲基化苯并胍胺、丁氧甲基化苯并胍胺、甲氧基甲基化尿素、丁氧甲基化尿素,或甲氧基甲基化硫基尿素等之化合物。且,也能夠使用此等之化合物之縮合物。
且,作為上述交聯劑,能夠使用耐熱性較高之交聯劑。作為耐熱性較高之交聯劑,能夠使用分子內具有芳香族環(例如苯環、萘環)且含有交聯形成取代基之化合物較佳。
此化合物有舉出具有下述式(4)之部分構造之化合物,或具有下述式(5)之重複單位之聚合物或寡聚物。
上述R
11、R
12、R
13及R
14為氫原子或碳數1至10之烷基,此等之烷基能夠使用上述例示。n3為1~4之整數,n4為1~(5-n3)之整數,(n3+n4)表示2~5之整數。n5為1~4之整數,n6為0~(4-n5),(n5+n6)表示1~4之整數。寡聚物及聚合物能夠在重複單位構造之數為2~100,或2~50之範圍內來使用。
上述化合物能夠作為旭有機材工業股份公司、本州化學工業股份公司之製品來取得。例如上述交聯劑中,式(4-24)之化合物能夠作為旭有機材工業股份公司、商品名TM-BIP-A來取得。
交聯劑之添加量會因使用之塗布溶媒、使用之基底基板、要求之溶液黏度、要求之膜形狀等而有所變動,但相對於全固形分,為0.001至80質量%,較佳為 0.01至50質量%,更較佳為0.05至40質量%。此等交聯劑會藉由自我縮合而引起交聯反應,但本發明之上述反應生成物中,有存在交聯性取代基時,能夠與此等之交聯性取代基引起交聯反應。
[酸及/或酸產生劑]
本發明之阻劑下層膜形成組成物能夠含有酸及/或酸產生劑。
作為酸,有舉例如p-甲苯磺酸、三氟甲磺酸、吡啶p-甲苯磺酸、吡啶酚磺酸、水楊酸、5-磺柳酸、4-酚磺酸、樟腦磺酸、4-氯苯磺酸、苯二磺酸、1-萘磺酸、檸檬酸、安息香酸、羥基安息香酸、萘羧酸等。
酸僅能夠使用一種,或組合二種以上來使用。摻混量相對於全固形分,通常為0.0001至20質量%,較佳為0.0005至10質量%,更較佳為0.01至3質量%。
作為酸產生劑,有舉出熱酸產生劑或光酸產生劑。
作為熱酸產生劑,有舉出2,4,4,6-四溴環己二烯酮、安息香甲苯磺酸酯、2-硝基芐基甲苯磺酸酯、K-PURE[註冊商標]CXC-1612、同CXC-1614、同TAG-2172、同TAG-2179、同TAG-2678、同TAG2689、同TAG2700(King Industries公司製)及SI-45、SI-60、SI-80、SI-100、SI-110、SI-150(三新化學工業(股)製)其他有機磺酸烷基酯等。
光酸產生劑會在阻劑曝光時產生酸。因此,能夠調整下層膜之酸性度。這是一種用於使下層膜之酸性度合於上層阻劑之酸性度之一方法。且,藉由下層膜之酸性度之調整,能夠調整形成於上層之阻劑之圖型形狀。
作為本發明之阻劑下層膜形成組成物中包含之光酸產生劑,有舉出鎓鹽化合物、磺基醯亞胺化合物及二磺醯基二偶氮甲烷化合物等。
作為鎓鹽化合物,有舉出二苯基錪鎓六氟磷酸酯、二苯基錪鎓三氟甲烷磺酸酯、二苯基錪鎓九氟正丁烷磺酸酯、二苯基錪鎓全氟正辛烷磺酸酯、二苯基錪鎓樟腦磺酸酯、雙(4-tert-丁基苯基)錪鎓樟腦磺酸酯及雙(4-tert-丁基苯基)錪鎓三氟甲烷磺酸酯等之錪鎓塩化合物及三苯基鋶六氟銻酸酯、三苯基鋶九氟正丁烷磺酸酯、三苯基鋶樟腦磺酸酯及三苯基鋶三氟甲烷磺酸酯等之鋶鹽化合物等。
作為磺基醯亞胺化合物,有舉例如N-(三氟甲烷磺醯基氧基)琥珀醯亞胺、N-(九氟正丁烷磺醯基氧基)琥珀醯亞胺、N-(樟腦磺醯基氧基)琥珀醯亞胺及N-(三氟甲烷磺醯基氧基)萘醯亞胺等。
作為二磺醯基二偶氮甲烷化合物,有舉例如雙(三氟甲基磺醯基)二偶氮甲烷、雙(環己基磺醯基)二偶氮甲烷、雙(苯基磺醯基)二偶氮甲烷、雙(p-甲苯磺醯基)二偶氮甲烷、雙(2,4-二甲基苯磺醯基)二偶氮甲烷及甲基磺醯基-p-甲苯磺醯基二偶氮甲烷等。
酸產生劑能夠僅使用一種,或組合二種以上來使用。
使用酸產生劑時,作為其比例,相對於阻劑下層膜形成組成物之固形分100質量份,為0.01至5質量份,或0.1至3質量份,或0.5至1質量份。
[其他成分]
本發明之阻劑下層膜形成組成物中,為了不產生針孔或紋路等,且進而提升對表面不均之塗布性,能夠摻混界面活性劑。作為界面活性劑,能夠舉例如聚氧乙烯月桂基醚、聚氧乙烯硬脂醯醚、聚氧乙烯鯨蠟醚、聚氧乙烯油醯醚等之聚氧乙烯烷基醚類、聚氧乙烯辛基酚醚、聚氧乙烯壬基酚醚等之聚氧乙烯烷基丙烯基醚類、聚氧乙烯・聚氧丙烯嵌段共聚合物類、山梨糖醇單月桂酸酯、山梨糖醇單棕櫚酸酯、山梨糖醇單硬脂酸酯、山梨糖醇單油酸酯、山梨糖醇三油酸酯、山梨糖醇三硬脂酸酯等之山梨糖醇脂肪酸酯類、聚氧乙烯山梨糖醇單月桂酸酯、聚氧乙烯山梨糖醇單棕櫚酸酯、聚氧乙烯山梨糖醇單硬脂酸酯、聚氧乙烯山梨糖醇三油酸酯、聚氧乙烯山梨糖醇三硬脂酸酯等之聚氧乙烯山梨糖醇脂肪酸酯類等之非離子系界面活性劑、F-top EF301、EF303、EF352(股份公司Tochem Products製,商品名)、MegaFuck F171、F173、R-40、R-40N、R-40LM(DIC股份公司製,商品名)、Florard FC430、FC431 (住友3M股份公司製,商品名)、Asahi Guard AG710、Surflon S-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子股份公司製,商品名)等之氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業股份公司製)等。此等之界面活性劑之摻混量相對於阻劑下層膜材料之全固形分,通常為2.0質量%以下,較佳為1.0質量%以下。此等之界面活性劑亦可單獨使用,或組合二種以上來使用。使用界面活性劑時,作為其比例,相對於阻劑下層膜形成組成物之固形分100質量份,為0.0001至5質量份,或0.001至1質量份,或0.01至0.5質量份。
本發明之阻劑下層膜形成組成物中能夠添加吸光劑、流動性調整劑、接著補助劑等。流動性調整劑有效於提升下層膜形成組成物之流動性。接著補助劑有效於提升半導體基板或阻劑與下層膜之密著性。
作為吸光劑,能夠使用例如「工業用色素之技術與市場」(CMC出版)或「染料便覧」(有機合成化學協會編)中記載之市售吸光劑,例如C.I.Disperse Yellow 1、3、4、5、7、8、13、23、31、49、50、51、54、60、64、66、68、79、82、88、90、93、102、114及124;C.I.Disperse Orange1、5、13、25、29、30、31、44、57、72及73;C.I.Disperse Red 1、5、7、13、17、19、43、50、54、58、65、72、73、88、117、137、143、199及210;C.I.Disperse Violet 43;C.I.Disperse Blue 96;C.I.Fluorescent Brightening Agent 112、135及163;C.I.Solvent Orange2及45;C.I.Solvent Red 1、3、8、23、24、25、27及49;C.I.Pigment Green 10;C.I.Pigment Brown 2等較適合。上述吸光劑通常相對於阻劑下層膜形成組成物之全固形分,為10質量%以下,較佳為5質量%以下之比例來摻混。
流動性調整劑主要是為了提升阻劑下層膜形成組成物之流動性,尤其是在烘烤步驟中,以提升阻劑下層膜之膜厚均一性,或提高阻劑下層膜形成組成物對孔洞內部之充填性之目的來添加。作為具體例,能夠舉出二甲基苯二甲酸酯、二乙基苯二甲酸酯、二異丁基苯二甲酸酯、二己基苯二甲酸酯、丁基異癸基苯二甲酸酯等之苯二甲酸衍生物、二正丁基己二酸酯、二異丁基己二酸酯、二異辛基己二酸酯、辛基癸基己二酸酯等之己二酸衍生物、二正丁基馬來酸酯、二乙基馬來酸酯、二壬基馬來酸酯等之馬來酸衍生物、甲基油酸酯、丁基油酸酯、四氫呋喃甲基油酸酯等之油酸衍生物,或正丁基硬脂酸酯、甘油基硬脂酸酯等之硬脂酸衍生物。此等之流動性調整劑相對於阻劑下層膜形成組成物之全固形分,通常以未滿30質量%之比例來摻混。
接著補助劑主要是提升基板或阻劑與阻劑下層膜形成組成物之密著性,尤其是在顯像中為了使阻劑較難剝離之目的而添加。作為具體例,能夠舉出三甲基氯矽烷、二甲基羥甲基氯矽烷、甲基二苯基氯矽烷、氯甲基二甲基氯矽烷等之氯矽烷類、三甲基甲氧基矽烷、二甲基二乙氧基矽烷、甲基二甲氧基矽烷、二甲基羥甲基乙氧基矽烷、二苯基二甲氧基矽烷、苯基三乙氧基矽烷等之烷氧基矽烷類、六甲基二矽氮烷、N,N'-雙(三甲基矽烷基)脲、二甲基三甲基矽烷基胺、三甲基矽烷基咪唑等之矽氮烷類、羥甲基三氯矽烷、γ-氯丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷等之矽烷類、苯并三吡咯、苯并咪唑、吲唑、咪唑、2-氫硫基苯并咪唑、2-氫硫基苯并噻唑、2-氫硫基苯并噁唑、脲唑、硫基脲嘧啶、氫硫基咪唑、氫硫基嘧啶等之雜環式化合物,或1,1-二甲基脲、1,3-二甲基脲等之尿素,或硫基尿素化合物。此等之接著補助劑相對於阻劑下層膜形成組成物之全固形分,通常未滿5質量%,較佳以未滿2質量%之比例來摻混。
本發明相關之阻劑下層膜形成組成物之固形分通常為0.1至70質量%,較佳為0.1至60質量%。固形分為自阻劑下層膜形成組成物去除溶劑之全成分之含有比例。固形分中上述反應生成物之比例依序以1至100質量%,1至99.9質量%,50至99.9質量%,50至95質量%,50至90質量%較佳。
評價阻劑下層膜形成組成物是否為均勻之溶液狀態之量表之一為觀察特定微濾器之通過性,但本發明相關之阻劑下層膜形成組成物會通過孔徑0.1μm之微濾器,且呈現均勻之溶液狀態。
作為上述微濾器材質,有舉出PTFE(聚四氟乙烯)、PFA(四氟乙烯・全氟烷基乙烯醚共聚合物)等之氟系樹脂、PE(聚乙烯)、UPE(超高分子量聚乙烯)、PP(聚丙烯)、PSF(聚碸)、PES(聚醚碸)、尼龍,但為PTFE(聚四氟乙烯)製較佳。
[阻劑下層膜及半導體裝置之製造方法]
以下關於使用本發明相關之阻劑下層膜形成組成物之阻劑下層膜及半導體裝置之製造方法進行說明。
於製造半導體裝置時所使用的基板(例如矽晶圓基板、矽/二氧化矽被覆基板、矽氮化物基板、玻璃基板、ITO基板、聚醯亞胺基板,及低介電係數材料(low-k材料)被覆基板等)上,使用旋轉塗布器、條狀塗布器等適當的塗布方法塗布本發明之光阻下層膜形成組成物,隨後,經由燒結而形成光阻下層膜。作為燒成條件,燒成溫度為適當地自80℃至400℃,燒成時間為適當地自0.3至60分鐘來選擇。較佳為燒成溫度為150℃至350℃,燒成時間0.5至2分鐘。於此,做為形成之下層膜之膜厚,例如為10至1000nm,或20至500nm,或30至400nm,或50至300nm。
且,本發明相關之有機阻劑下層膜上也能夠形成無機阻劑下層膜(硬光罩)。例如除了將WO2009/104552A1記載之含矽之阻劑下層膜(無機阻劑下層膜)形成組成物以旋轉塗布來形成之方法外,能夠將Si系之無機材料膜以CVD法等來形成。
且,將本發明相關之阻劑下層膜形成組成物塗布於具有段差之部分與不具有段差之部分之半導體基板(所謂段差基板)上,藉由燒成,能夠形成具有該段差之部分與不具有段差之部分之段差在3~70nm之範圍內之阻劑下層膜。
接著,在其阻劑下層膜上,形成阻劑膜,例如光阻之層。光阻之層之形成能夠藉由周知方法,亦即塗布於光阻組成物溶液之下層膜上及燒成來進行。作為光阻之膜厚,例如為50至10000nm,或100至2000nm,或200至1000nm。
作為形成於阻劑下層膜之上的光阻,只要可感受曝光所使用之光線者即可,並未有特別之限定。其可使用負型光阻及正型光阻中之任一種。例如,由酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所形成之正型光阻、由具有經酸分解而提高鹼溶解速度之基的黏結劑與光酸產生劑所形成之化學增寬度型光阻、由經酸而分解而提高光阻的鹼溶解速度之低分子化合物與鹼可溶性黏結劑與光酸產生劑所形成之化學增寬度型光阻,及由具有經酸分解而提高鹼溶解速度之基的黏結劑與經酸分解而提高光阻的鹼溶解速度之低分子化合物與光酸產生劑所形成之化學增寬度型光阻等。有舉例如CHYPRE公司製商品名APEX-E、住友化學工業股份公司製商品名PAR710及信越化學工業股份公司製商品名SEPR430等。且,能夠舉例如如Proc. SPIE, Vol. 3999, 330-334(2000)、Proc. SPIE, Vol. 3999, 357-364(2000),或Proc.SPIE,Vol.3999,365-374(2000)中記載之如含氟原子聚合物系光阻。
接著,以光或電子線之照射與顯像來形成阻劑圖型。首先,通過特定之光罩來進行曝光。曝光有使用近紫外線、遠紫外線,或極端紫外線(例如、EUV(波長13.5nm))等。具體來說能夠使用KrF準分子雷射(波長248nm)、ArF準分子雷射(波長193nm)及F
2準分子雷射(波長157nm)等。此等中,為ArF準分子雷射(波長193nm)及EUV(波長13.5nm)較佳。曝光後,因應必要,也能夠進行曝光後加熱(post exposure bake)。曝光後加熱之加熱溫度為適當地選自70℃至150℃,加熱時間為適當地選自0.3至10分鐘,以此條件來進行。
且,本發明中,作為阻劑能夠使用電子線微影用阻劑來取代光阻。作為電子線阻劑,能夠使用負型、正型之任一者。由具有經酸產生劑與酸而分解,而使鹼溶解速度產生變化之基的黏結劑所形成之化學增寬度型光阻、由具有經鹼可溶性黏結劑與酸產生劑與酸而分解,使阻劑的鹼溶解速度產生變化的低分子化合物所形成之化學增寬度型光阻、由具有經酸產生劑與酸而分解,而使鹼溶解速度產生變化之基的黏結劑與經酸分解而使阻劑的鹼溶解速度產生變化之低分子化合物所形成之化學增寬度型光阻、由具有經電子線分解而使鹼溶解速度產生變化之基的黏結劑所形成之非化學增寬度型光阻、由具有被電子線切斷而使鹼溶解速度產生變化之部位的黏結劑所形成之非化學增寬度型光阻等。使用該些電子線阻劑的情形可與使用照射源為使用電子線的光阻的情形同樣地可形成阻劑圖型。
接著,藉由顯像液來進行顯像。藉此,例如使用正型光阻時,經曝光部分之光阻會被去除,形成光阻之圖型。
作為顯像液,能夠舉出羥化鉀、羥化鈉等之鹼金屬羥化物之水溶液、羥化四甲基銨、羥化四乙基銨、膽鹼等之羥化四級銨之水溶液、乙醇胺、丙基胺、乙二胺等之胺水溶液等之鹼性水溶液作為例子。進而,此等之顯像液中能夠添加界面活性劑等。作為顯像之條件,溫度為適當地選自5℃至50℃,時間為適當地選自10至600秒。
且,將如此所形成之光阻(上層)之圖型作為保護膜,進行無機下層膜(中間層)之去除,接著,將含有經圖型化之光阻及無機下層膜(中間層)之膜作為保護膜,進行有機下層膜(下層)之去除。最後,將經圖型化之無機下層膜(中間層)及有機下層膜(下層)作為保護膜,進行半導體基板之加工。
首先,將去除光阻部分之無機下層膜(中間層)以乾蝕刻去除,使半導體基板露出。無機下層膜之乾蝕刻中能夠使用四氟甲烷(CF
4)、全氟環丁烷(C
4F
8)、全氟丙烷(C
3F
8)、三氟甲烷、一氧化碳、氬、氧、氮、六氟化硫、二氟甲烷、三氟化氮及三氟化氯、氯、三氯化硼及二氯化硼等之氣體。無機下層膜之乾蝕刻係使用鹵素系氣體較佳,為氟系氣體再較佳。作為氟系氣體,有舉例如四氟甲烷(CF
4)、全氟環丁烷(C
4F
8)、全氟丙烷(C
3F
8)、三氟甲烷及二氟甲烷(CH
2F
2)等。
之後,將含有經圖型化之光阻及無機下層膜之膜作為保護膜,來進行有機下層膜之去除。有機下層膜(下層)以氧系氣體之乾蝕刻來進行較佳。這是因為包含較多矽原子之無機下層膜以氧系氣體之乾蝕刻會較難去除。
最後,進行半導體基板之加工。半導體基板之加工藉由氟系氣體之乾蝕刻來進行較佳。
作為氟系氣體,有舉例如四氟甲烷(CF
4)、全氟環丁烷(C
4F
8)、全氟丙烷(C
3F
8)、三氟甲烷及二氟甲烷(CH
2F
2)等。
且,阻劑下層膜之上層在光阻之形成前,能夠形成有機系之反射防止膜。作為於此使用之反射防止膜組成物,並無特別限制,能夠從至今在微影製程中所慣用者中任意地選擇來使用,且慣用之方法,能夠例如以旋轉塗布器、塗布機之塗布及燒成來進行反射防止膜之形成。
本發明中,在基板上將有機下層膜成膜後,能夠於其上方將無機下層膜成膜,進而於其上方被覆光阻。藉此,光阻之圖型寬度會變窄,為了防止圖型倒塌,而薄薄地被覆光阻時,藉由選擇適當的蝕刻氣體,能夠加工基板。例如將對光阻具有十分快速的蝕刻速度之氟系氣體作為蝕刻氣體,能夠對阻劑下層膜加工,將對無機下層膜具有十分快速蝕刻速度之氟系氣體作為蝕刻氣體,能夠加工基板,進而,將對有機下層膜具有十分快速蝕刻速度之氧系氣體作為蝕刻氣體,能夠進行基板之加工。
由阻劑下層膜形成組成物形成之阻劑下層膜有時會進而因微影製程中所使用之光之波長,具有對其光之吸收能。且,此時,能夠具有作為反射防止膜之功能,其係具有防止自基板之反射光之效果。進而,由本發明之阻劑下層膜形成組成物形成之下層膜也能夠具有作為硬光罩之功能。本發明之下層膜也能夠作為用來防止基板與光阻之相互作用之層、具有防止對光阻中使用之材料或光阻曝光時所生成之物質對基板的不良作用之功能之層、具有防止加熱燒成時自基板生成之物質對上層光阻之擴散之功能之層,及用來減少半導體基板誘電體層之光阻層之毒害效果之障蔽層等。
且,由阻劑下層膜形成組成物形成之下層膜適用在有形成雙鑲嵌製程所使用之穿孔之基板上,且能夠作為無空隙地填充孔洞之埋入材來使用。且,也能夠作為用來將具有凹凸之半導體基板表面平坦化之平坦化材來使用。
[實施例]
以下,使用下述實施例來說明本發明之阻劑下層膜形成組成物之具體例,但本發明不限定於此等。
本說明書之下述合成例所示之重量平均分子量為凝膠滲透層析(以下,在本說明書中簡稱為GPC)所得之測定結果。測定為使用TOSOH股份公司製GPC裝置(HLC-8320GPC),且測定條件等如下述。
GPC管柱:TSKgelSuperH-RC,TSKgelSuperMultipore HZ-N,TSKgelSuperMultipore HZ-N(TOSOH股份公司製)
管柱溫度:40℃
溶媒:四氫呋喃(關東化學,高速液體層析用)
標準試料:聚苯乙烯(Shodex製)
且,下述合成例中記載之簡稱表示以下意義。
Cz:咔唑
ECz:9-乙基咔唑
Glyoxal:乙二醛
1Na:1-萘酚
2,3-DMP:2,3-二甲基酚
Glutalaldehyde:戊二醛
EHA:2-乙基己醛
<合成例1>
(聚合物(A)之合成)(Cz/Glyoxal=100/30)
於具備攪拌棒、冷卻管之200毫升容量之四口燒瓶中,添加咔唑(東京化成工業(股)製)20.00g(119.61mmol)、乙二醛(39%水溶液,約8.8mol/L,東京化成工業(股)製)5.34g(35.88mmol)、p-甲苯磺酸一水和物(東京化成工業(股)製)0.07g(0.36mmol)、1,4-二氧雜環(關東化學、鹿特級)33.97g,升溫至90℃,於90℃下攪拌13小時。降溫至60℃以下後,添加四氫呋喃(關東化學,特級)56.68g來稀釋,冷卻至30℃以下。將所得之反應混合物滴入1L之甲醇(關東化學,特級)/水(8/2)混合溶媒中,使聚合物沉澱。過濾所得之沉澱物,將過濾物以250mL之甲醇/水(8/2)分三次來洗淨,真空乾燥後得到聚合物。將此聚合物之分子量以GPC(標準聚苯乙烯換算)來測定,重量平均分子量(Mw)為1617,且收率為38.1%。此聚合物具有下述式(A)表示之重複單位構造。將所得之聚合物以丙二醇單甲基醚乙酸酯稀釋成固形分濃度30%,各自添加與固形分量同量之陽離子交換樹脂與陰離子交換樹脂,攪拌4小時。將離子交換樹脂過濾,得到聚合物(A)溶液。
<合成例2>
(聚合物(B)之合成)(ECz/Glyoxal=100/70)
於具備攪拌棒、冷卻管之200毫升容量之四口燒瓶中,添加9-乙基咔唑(東京化成工業(股)製)19.00g (97.30 mmol)、乙二醛(39%水溶液,約8.8mol/L,東京化成工業(股)製)10.14g(68.11mmol)、p-甲苯磺酸一水和物(東京化成工業(股)製)1.30g(6.81mmol)、1,4-二氧雜環(關東化學,鹿特級)26.95g,升溫至90℃,於90℃下攪拌15小時。降溫至60℃以下後,添加四氫呋喃(關東化學,特級)57.38g來稀釋,冷卻至30℃以下。將所得之反應混合物滴入1L之2-丙醇(關東化學,特級),使聚合物沉澱。過濾所得之沉澱物,將過濾物以250mL之2-丙醇分三次來洗淨,真空乾燥後得到聚合物。將此聚合物之分子量以GPC(標準聚苯乙烯換算)來測定,重量平均分子量(Mw)為768,且收率為44.8%。此聚合物具有下述式(B)表示之重複單位構造。將所得之聚合物以丙二醇單甲基醚乙酸酯稀釋成固形分濃度30%,各自添加與固形分量同量之陽離子交換樹脂與陰離子交換樹脂,攪拌4小時。將離子交換樹脂過濾,得到聚合物(B)溶液。
<合成例3>
(聚合物(C)之合成)(ECz/Cz/Glyoxal=70/30/70)
於具備攪拌棒、冷卻管之200毫升容量之四口燒瓶中,添加9-乙基咔唑(東京化成工業(股)製)13.00g(66.57 mmol)、咔唑(東京化成工業(股)製)4.77g(28.53mmol)、乙二醛(39%水溶液,約8.8mol/L,東京化成工業(股)製)9.91g(66.57mmol)、p-甲苯磺酸一水和物(東京化成工業(股)製)1.27g(6.66mmol)、1,4-二氧雜環(關東化學,鹿特級)25.14g,升溫至90℃,於90℃下攪拌24小時。降溫至60℃以下後,添加四氫呋喃(關東化學、特級)54.09g來稀釋,冷卻至30℃以下。將所得之反應混合物滴入1L之甲醇(關東化學,特級)/水(8/2)混合溶媒中,使聚合物沉澱。過濾所得之沉澱物,將過濾物以250mL之甲醇/水(8/2)分三次來洗淨,真空乾燥後得到聚合物。將此聚合物之分子量以GPC(標準聚苯乙烯換算)來測定,重量平均分子量(Mw)為1358,且收率為75.7%。此聚合物具有下述式(C)表示之重複單位構造。將所得之聚合物以丙二醇單甲基醚乙酸酯稀釋成固形分濃度30%,各自添加與固形分量同量之陽離子交換樹脂與陰離子交換樹脂,攪拌4小時。將離子交換樹脂過濾,得到聚合物(C)溶液。
<合成例4>
(聚合物(D)之合成)(Cz/1Na/Glyoxal=50/50/50)
於具備攪拌棒、冷卻管之200毫升容量之四口燒瓶中,添加咔唑(東京化成工業(股)製)11.00g(65.79mmol)、1-萘酚(東京化成工業(股)製)9.48g(65.79mmol)、乙二醛(39%水溶液,約8.8mol/L,東京化成工業(股)製)5.87g (39.47mmol)、p-甲苯磺酸一水和物(東京化成工業(股)製)0.75g(3.95mmol)、1,4-二氧雜環(關東化學,鹿特級)29.83g,升溫至90℃,於90℃下攪拌21小時。降溫至60℃以下後,添加四氫呋喃(關東化學,特級)56.94g來稀釋,冷卻至30℃以下。將所得之反應混合物滴入1L之甲醇(關東化學,特級)/水(5/5)混合溶媒,使聚合物沉澱。過濾所得之沉澱物,將過濾物以250mL之甲醇/水(5/5)混合溶媒分三次來洗淨,真空乾燥後得到聚合物。將此聚合物之分子量以GPC(標準聚苯乙烯換算)來測定,重量平均分子量(Mw)為1053,且收率為66.3%。此聚合物具有下述式(D)表示之重複單位構造。將所得之聚合物以丙二醇單甲基醚乙酸酯稀釋成固形分濃度30%,各自添加與固形分量同量之陽離子交換樹脂與陰離子交換樹脂,攪拌4小時。將離子交換樹脂過濾,得到聚合物(D)溶液。
<合成例5>
(聚合物(E)之合成)(2,3-DMP/Glutalaldehyde=100/30)
於具備攪拌棒、冷卻管之200毫升容量之四口燒瓶中,添加2,3-二甲基酚(東京化成工業(股)製)17.00g (139.15mmol)、戊二醛(東京化成工業(股)製、約50%水溶液)8.37g(341.75mmol)、p-甲苯磺酸一水和物(東京化成工業(股)製)0.80g(4.2mmol)、1,4-二氧雜環59.28g,升溫至90℃,於90℃下攪拌97.5小時。將反應液冷卻至30℃以下,添加四氫呋喃(關東化學,特級)21.18g來稀釋。將所得之反應混合物滴入950mL之甲醇(關東化學,特級)/水(7/3)混合溶媒,使聚合物沉澱。過濾所得之沉澱物,將過濾物以240mL之甲醇/水(7/3)混合溶媒分三次來洗淨,真空乾燥後得到聚合物。將此聚合物之分子量以GPC(標準聚苯乙烯換算)來測定,重量平均分子量(Mw)為1920,且收率為56.9%。此聚合物具有下述式(E)表示之重複單位構造。將所得之聚合物以丙二醇單甲基醚乙酸酯稀釋成固形分濃度30%,各自添加與固形分量同量之陽離子交換樹脂與陰離子交換樹脂,攪拌4小時。將離子交換樹脂過濾,得到聚合物(E)溶液。
<合成例6>
(聚合物(F)之合成)(Cz/EHA=50/50)
於具備攪拌棒、冷卻管之200毫升容量之四口燒瓶中,添加咔唑(東京化成工業(股)製)12.00g(71.77mmol)、2-乙基己醛(東京化成工業(股)製)9.21g(71.77mmol)、甲磺酸(東京化成工業(股)製)1.40g(14.36mmol)、丙二醇單甲基醚乙酸酯49.13g,升溫至120℃,於120℃下攪拌38.5小時。將反應液冷卻至30℃以下,將所得之反應混合物滴入640mL之甲醇(關東化學,特級),使聚合物沉澱。過濾所得之沉澱物,將過濾物以160mL之甲醇分三次來洗淨,真空乾燥後得到聚合物。將此聚合物之分子量以GPC(標準聚苯乙烯換算)來測定,重量平均分子量(Mw)為19476,且收率為72.6%。此聚合物具有下述式(F)表示之重複單位構造。將所得之聚合物以丙二醇單甲基醚乙酸酯稀釋成固形分濃度30%,各自添加與固形分量同量之陽離子交換樹脂與陰離子交換樹脂,攪拌4小時。將離子交換樹脂過濾,得到聚合物(F)溶液。
<實施例1>
於合成例1所得之樹脂2.94g中混合包含2%之吡啶p-羥基苯磺酸酯之丙二醇單甲基醚0.82g、TMOM-BP(本州化學工業(股)製,交聯劑)0.16g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.08g、丙二醇單甲基醚1.00g、丙二醇單甲基醚乙酸酯1.39g、環己酮3.60g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
<實施例2>
於合成例1所得之樹脂2.82g中混合包含2%之吡啶p-羥基苯磺酸酯之丙二醇單甲基醚0.98g、四甲氧基甲基乙炔脲0.2g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.08g、丙二醇單甲基醚0.84g、丙二醇單甲基醚乙酸酯1.49g、環己酮3.60g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
<實施例3>
於合成例2所得之樹脂1.79g中混合包含2%之吡啶p-羥基苯磺酸酯之丙二醇單甲基醚0.23g、TMOM-BP(本州化學工業(股)製,交聯劑)0.05g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.05g、丙二醇單甲基醚0.68g、丙二醇單甲基醚乙酸酯0.41g、環己酮1.80g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
<實施例4>
於合成例3所得之樹脂1.50g中混合包含2%之吡啶p-羥基苯磺酸酯之丙二醇單甲基醚0.23g、TMOM-BP(本州化學工業(股)製,交聯劑)0.05g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.05g、丙二醇單甲基醚0.68g、丙二醇單甲基醚乙酸酯1.76g、環己酮0.75g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
<實施例5>
於合成例3所得之樹脂1.37g中混合包含2%之吡啶p-羥基苯磺酸酯之丙二醇單甲基醚0.23g、四甲氧基甲基乙炔脲0.08g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.04g、丙二醇單甲基醚0.50g、丙二醇單甲基醚乙酸酯1.76g、環己酮0.84g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
<實施例6>
於合成例4所得之樹脂1.76g中混合包含2%之吡啶p-羥基苯磺酸酯之丙二醇單甲基醚0.41g、四甲氧基甲基乙炔脲0.08g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.04g、丙二醇單甲基醚0.95g、丙二醇單甲基醚乙酸酯1.76g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
<比較例1>
於合成例5所得之樹脂2.87g中混合包含1%之吡啶p-甲苯磺酸酯之丙二醇單甲基醚0.77g、四甲氧基甲基乙炔脲0.08g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.08g、丙二醇單甲基醚1.98g、丙二醇單甲基醚乙酸酯4.23g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
<比較例2>
於合成例6所得之樹脂2.96g中混合包含1%之吡啶p-甲苯磺酸酯之丙二醇單甲基醚0.77g、四甲氧基甲基乙炔脲0.08g、包含1%之界面活性劑(DIC(股)製,品名:MegaFuck [商品名]R-40,氟系界面活性劑)之丙二醇單甲基醚乙酸酯0.08g、丙二醇單甲基醚1.98g、丙二醇單甲基醚乙酸酯4.14g。之後,以口徑0.1μm之聚四氟乙烯製微濾器過濾,調整阻劑下層膜形成組成物之溶液。
[對光阻溶劑之溶出試驗]
將實施例1至實施例6及比較例1、比較例2所調製之阻劑下層膜形成組成物各自以旋轉塗布器塗布於矽晶圓上。之後,在熱板上以240℃烘烤1分鐘,形成阻劑下層膜(膜厚0.2μm)。將此等之阻劑下層膜浸漬於光阻溶液所使用之溶劑之PGME/PGMEA混合溶媒(質量混合比70/30)中,確認對溶劑為不溶,將其結果於下述表1以"○"來表示。
[光學參數之試驗]
將實施例1至實施例6及比較例1、比較例2所調製之阻劑下層膜形成組成物各自以旋轉塗布器塗布於矽晶圓上。之後,在熱板上以下述表1所示之溫度烘烤1分鐘,形成阻劑下層膜(膜厚0.2μm)。使用光橢圓偏光計(J.A.Woollam公司製,VUV-VASE VU-302),測定此等之阻劑下層膜之波長193nm中之折射率(n值)及衰減係數(k值)。將其結果表示於下述表1。為了使上述阻劑下層膜具有充分之反射防止機能,期望波長193nm中之k值為0.1以上。
[乾蝕刻速度之測定]
使用實施例1至實施例6及比較例1、2所調製之阻劑下層膜形成組成物,以與上述相同之方法,在矽晶圓上形成阻劑下層膜。且,將此等之阻劑下層膜之乾蝕刻速度使用Samco股份公司製RIE系統,將CF
4作為乾蝕刻氣體來使用,並在此條件下進行測定。將前述實施例5之乾蝕刻速度作為1.00,算出此時前述各阻劑下層膜之乾蝕刻速度。將其結果於下述表1中作為"相對乾蝕刻速度"來表示。相較於比較例1,使用實施例1至實施例6所調製之阻劑下層膜形成組成物來形成之阻劑下層膜之乾蝕刻速度具有非常慢的乾蝕刻速度,因此表示將本阻劑下層膜形成組成物作為光罩,來進行基板加工較容易。
[硬度之測定]
將實施例1至實施例6及比較例1、2所調製之阻劑下層膜形成組成物各自以旋轉塗布器塗布於矽晶圓上。之後,於熱板上以240℃烘烤1分鐘,形成阻劑下層膜(膜厚0.2μm)。東陽technical公司製奈米壓痕機進行奈米壓痕試驗,測定上述阻劑下層膜之硬度。實施例1至實施例6顯示0.50GPa以上之硬度,這表示由於具有更緻密之構造,因此以蝕刻來加工基板較有利。
[埋入性評價]
以200nm膜厚之SiO
2基板、凹槽寬度50nm、節距100nm之緻密圖型區域來確認埋入性。將實施例1至實施例6及比較例1、比較例2所調製之阻劑下層膜形成組成物塗布於上述基板上後。以240℃燒成60秒鐘,形成約200 nm之阻劑下層膜。將此基板之平坦化性使用日立High technologies股份公司製掃描型電子顯微鏡(S-4800)來觀察,確認阻劑下層膜形成組成物有無充填於圖型內部,且實施例1至實施例6為良好。
藉由本發明,能夠提供一種能夠形成顯示較高之蝕刻耐性、良好之乾蝕刻速度比及光學定數,亦即對段差基板之被覆性亦良好,埋入後之膜厚差較小且平坦,進而具有優異之硬度之膜之阻劑下層膜形成組成物、適合該阻劑下層膜形成組成物之聚合物、使用該阻劑下層膜形成組成物之阻劑下層膜,以及半導體裝置之製造方法。
Claims (12)
- 一種阻劑下層膜形成組成物,包含下述式(1)或式(2)表示之化合物與下述式(3)表示之化合物之反應生成物,及溶劑, (式(1)或式(2)中,Ar 1、Ar 2各自獨立為亦可經R 1、R 2取代之苯環或萘環,R 1及R 2各自獨立為氫原子、鹵原子、硝基、胺基、羥基、碳數1至10之烷基、碳數2至10之烯基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合,R 3為氫原子、碳數1至10之烷基、碳數2至10之烯基、碳數2至10之炔基、碳數6至40之芳基,或亦可包含醚鍵結、酮鍵結或者酯鍵結之此等之組合,n 1及n 2在Ar 1、Ar 2為苯環時,各自為1至3之整數,在Ar 1、Ar 2為萘環時,各自為1至5之整數, 式(3)中,X為單鍵結、碳數1至30之亦可包含氮原子、氧原子、硫原子之飽和或者不飽和之直鏈或環狀之有機基,或碳數6至30之伸芳基)。
- 如請求項1之阻劑下層膜形成組成物,其中,式(1)或式(2)中,Ar 1及Ar 2為苯環。
- 如請求項1或請求項2之阻劑下層膜形成組成物,其中,式(1)中,R 1、R 2各自為氫原子。
- 如請求項1至請求項3中任1項之阻劑下層膜形成組成物,其中,式(3)中,X為單鍵結,或碳數1至30之亦可包含氮原子之飽和或者不飽和之直鏈或環狀之有機基。
- 如請求項1至請求項3中任1項之阻劑下層膜形成組成物,其中,式(3)中,X為單鍵結。
- 如請求項1至請求項5中任1項之阻劑下層膜形成組成物,其中,包含2種類以上前述式(1)或式(2)表示之化合物與前述式(3)表示之化合物之反應生成物。
- 如請求項1至請求項5中任1項之阻劑下層膜形成組成物,其中,包含前述式(1)或式(2)表示之化合物,進而為前述式(1)或式(2)表示之化合物以外之其他芳香族化合物與前述式(3)表示之化合物之反應生成物。
- 如請求項1至請求項7中任1項之阻劑下層膜形成組成物,其中,進而包含交聯劑。
- 如請求項1至請求項8中任1項之阻劑下層膜形成組成物,其中,進而包含酸及/或酸產生劑。
- 如請求項1至請求項9中任1項之阻劑下層膜形成組成物,其中,前述溶劑之沸點為160℃以上。
- 一種阻劑下層膜,其係包含如請求項1至請求項10中任1項之阻劑下層膜形成組成物之塗布膜之燒成物。
- 一種半導體裝置之製造方法,其係包含 在半導體基板上使用如請求項1至請求項10中任1項之阻劑下層膜形成組成物,形成阻劑下層膜之步驟、 在所形成之阻劑下層膜上形成阻劑膜之步驟、 對所形成之阻劑膜,藉由光或電子線之照射與顯像,形成阻劑圖型之步驟、 介隔著所形成之阻劑圖型,將前述阻劑下層膜蝕刻並圖型化之步驟,及 介隔著經圖型化之阻劑下層膜,加工半導體基板之步驟。
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