CN110837205A - 芳香族底层 - Google Patents
芳香族底层 Download PDFInfo
- Publication number
- CN110837205A CN110837205A CN201910698511.8A CN201910698511A CN110837205A CN 110837205 A CN110837205 A CN 110837205A CN 201910698511 A CN201910698511 A CN 201910698511A CN 110837205 A CN110837205 A CN 110837205A
- Authority
- CN
- China
- Prior art keywords
- layer
- membered ring
- alkylene
- alkyl
- attached
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 52
- 239000010410 layer Substances 0.000 claims description 155
- 239000000758 substrate Substances 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 44
- 229920002120 photoresistant polymer Polymers 0.000 claims description 38
- 229920000642 polymer Polymers 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 33
- 229910052710 silicon Inorganic materials 0.000 claims description 33
- 239000010703 silicon Substances 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 239000008199 coating composition Substances 0.000 claims description 20
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 238000000576 coating method Methods 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000005647 linker group Chemical group 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 6
- 238000000059 patterning Methods 0.000 claims description 4
- 239000006117 anti-reflective coating Substances 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 abstract description 16
- 239000000178 monomer Substances 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical group C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract description 8
- 229920001519 homopolymer Polymers 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 12
- 235000012431 wafers Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000005530 etching Methods 0.000 description 10
- 238000011049 filling Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 229940116333 ethyl lactate Drugs 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000003431 cross linking reagent Substances 0.000 description 7
- 238000005229 chemical vapour deposition Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- -1 hydrocarbon radical Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002318 adhesion promoter Substances 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 230000003667 anti-reflective effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 125000000743 hydrocarbylene group Chemical group 0.000 description 4
- 238000005691 oxidative coupling reaction Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920005591 polysilicon Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000012876 topography Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- JEIHSRORUWXJGF-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]propan-2-yl acetate Chemical compound CC(=O)OC(C)COC(C)(C)C JEIHSRORUWXJGF-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LEVVHYCKPQWKOP-UHFFFAOYSA-N [Si].[Ge] Chemical compound [Si].[Ge] LEVVHYCKPQWKOP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 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
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 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
- 239000013638 trimer Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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Abstract
由具有两个2‑萘酚部分的单体形成的可固化均聚物在半导体制造工艺中可用作底层。
Description
本发明总体上涉及制造电子装置的领域,并且更具体地涉及在半导体制造中用作底层的材料的领域。
在光刻工艺中众所周知的是,如果抗蚀剂图案过高(高纵横比),则由于来自所使用的显影剂的表面张力,所述抗蚀剂图案可能塌陷。已经设计了多层抗蚀剂工艺(如三层和四层工艺),这可以在希望高纵横比的情况下解决图案倒塌这个问题。此类多层工艺使用抗蚀剂顶层、一个或多个中间层、以及底部层(bottom layer)(或底层(underlayer))。在此类多层抗蚀剂工艺中,将顶部光致抗蚀剂层成像并以典型的方式显影以提供抗蚀剂图案。然后典型地通过蚀刻将图案转移到一个或多个中间层。选择每个中间层,使得使用不同的蚀刻工艺,如不同的等离子体蚀刻。最后,典型地通过蚀刻将图案转移到底层。此类中间层可以由多种材料构成,然而底层材料典型地由高碳含量材料构成。选择底层材料以提供所希望的减反射特性、平坦化特性、以及蚀刻选择性。
用于底层的现有技术包括化学气相沉积(CVD)碳以及经过溶液处理的高碳含量聚合物。CVD材料具有若干显著的限制,包括高拥有成本、无法在衬底上的形貌上形成平坦化层、以及在633nm处用于图案对准的高吸光度。出于这些原因,业界已经转向作为底层的经过溶液处理的高碳含量材料。理想的底层需要满足以下特性:能够通过旋涂工艺流延到衬底上;在加热时热定形(固化),具有低脱气和升华;可溶于良好设备相容性的常见处理溶剂中;具有适当的n和k值以结合当前使用的硅硬掩模和底部减反射(BARC)层起作用以赋予光致抗蚀剂成像必需的低反射率,以及直至>400℃是热稳定的以便在随后的CVD工艺例如氮氧化硅(SiON)、氮化硅、氧化硅等等期间不受损坏。
芳香族结构单元典型地用于提供具有希望的热稳定性的底层材料。然而,具有高芳香族碳含量的底层材料倾向于受制于在常见处理溶剂中差的溶解性。已经做出了各种尝试来使用常规的酚醛清漆聚合方法制备高芳香族含量的底层材料,所述方法将羟基和脂肪族碳引入聚合物中。仍然需要在相对较低的温度下固化,在常见处理溶剂中具有良好的溶解性并且不受制于金属催化剂、硼、卤素、和/或磷污染的底层材料。
本发明提供了一种方法,所述方法包括:(a)提供电子装置衬底;(b)将包含一种或多种可固化化合物的涂层组合物层涂覆到所述电子装置衬底的表面上,其中所述一种或多种可固化化合物是包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000;(c)将所述可固化化合物的层固化以形成底层;(d)将光致抗蚀剂层涂覆在所述底层上;(e)通过掩模将所述光致抗蚀剂层暴露于光化辐射;(f)使暴露的光致抗蚀剂层显影以形成抗蚀剂图案;以及(g)将所述图案转移至所述底层以暴露所述电子装置衬底的一部分。
本发明还提供了一种包括电子装置衬底的电子装置,在所述电子装置衬底的表面上具有包含作为聚合单元的一种或多种可固化化合物的聚合物层,其中所述一种或多种可固化化合物是包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000。
本发明进一步提供了一种包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000。
本发明还提供了一种用于填充间隙(或孔)的方法,所述方法包括:(a)提供半导体衬底,在所述衬底的表面上具有浮雕图像,所述浮雕图像包括多个待填充的间隙;(b)将一种或多种以上描述的聚合物的涂层施加到所述浮雕图像上;以及(c)在足以固化所述涂层的温度下加热所述涂层。
将理解的是,当一个元件被称为是“在”另一个元件“之上”时,它可以与另一个元件或可能存在于其间的插入元件直接相邻。相反,当一个元件被称为是“直接在”另一个元件“之上”时,不存在插入元件。如本文使用的,术语“和/或”包括相关列出项中的一个或多个的任何和全部组合。
还将理解的是,尽管术语第一、第二、第三等可以在本文中用于描述不同元件、组件、区域、层和/或部分,但这些元件、组件、区域、层和/或部分不应被这些术语限制。这些术语仅用于区分一个元件、组件、区域、层或部分与另一个元件、组件、区域、层或部分。因此,以下讨论的第一元件、组件、区域、层或部分可在不背离本发明传授内容的情况下被称为第二元件、组件、区域、层或部分。
如本说明书通篇所使用的,除非上下文另有明确指示,否则以下缩写将具有以下含义:℃=摄氏度;g=克;mg=毫克;L=升;mL=毫升;nm=纳米;μm=微米(micron)=微米(micrometer);mm=毫米;sec.=秒;min.=分钟;hr.=小时;DI=去离子的;以及Da=道尔顿。除非另外说明,否则缩写“wt%”是指基于参考组合物的总重量的重量百分比。除非另外说明,否则所有的量是wt%并且所有的比率是摩尔比。所有数值范围都是包含端值的,并且可以按任何顺序组合,除了显然此数值范围被限制为加起来最高达100%的情况之外。冠词“一个/种(a/an)”和“所述(the)”是指单数和复数。
除非另外说明,否则“烷基”是指直链、支链和环状烷基。除非另外说明,否则“烯基”是指直链、支链和环状烯基。“卤素”是指氟、氯、溴和碘。除非另外指出,否则“烷基”包括“杂烷基”。术语“杂烷基”是指用一个或多个杂原子(如氮、氧、硫、磷)替代基团内的一个或多个碳原子的烷基基团,例如,如在醚或硫醚中。在一个优选的实施例中,“烷基”不包括“杂烷基”。如果对于任何烷基或杂烷基没有指示碳的数目,则预期是1-20个碳。如果对于任何烯基或炔基没有指示碳的数目,则预期是2-20个碳。“芳基”包括芳香族碳环以及芳香族杂环。优选的是,芳基部分是芳香族碳环。“取代的芳基”是指其一个或多个氢被一个或多个选自以下各项的取代基替代的任何芳基部分:卤素、C1-6-烷基、卤代-C1-6-烷基、C1-6-烷氧基、卤代-C1-6-烷氧基、苯基、和苯氧基,优选选自卤素、C1-6-烷基、卤代-C1-4-烷基、C1-6-烷氧基、卤代-C1-4-烷氧基、和苯基,并且更优选选自卤素、C1-6-烷基、C1-6-烷氧基、苯基、和苯氧基。优选地,取代的芳基具有1至3个取代基、并且更优选1或2个取代基。术语“烃基”和“亚烃基”是指饱和和不饱和的脂肪族和脂环族部分以及芳香族烃部分,其各自可以含有一个或多个选自O、S和N的杂原子。优选的“烃基”部分是烷基、烯基、炔基和芳基部分。同样地,优选的“亚烃基”部分是亚烷基、亚烯基、亚炔基和亚芳基。术语“任选取代的烃基”或“任选取代的亚烃基”是指取代和未取代的烷基或亚烷基、取代和未取代的烯基或亚烯基、取代和未取代的炔基或亚炔基、以及取代和未取代的芳基或亚芳基。术语“取代的烃基”和“取代的亚烃基”是指其一个或多个氢被一个或多个惰性取代基替代的烃基或亚烃基部分。术语“惰性取代基”意指在用于形成本发明的聚合物的聚合步骤期间不反应的任何取代基。示例性惰性取代基是C1-20-烷氧基、C5-20-芳基、C1-20-烷基、C2-20-烯基、C2-20-炔基、羟基、和卤素。
如本文使用的,术语“聚合物”包括低聚物。术语“低聚物”是指能够进一步固化的二聚物、三聚物、四聚物和其他聚合物材料。术语“固化”意指增加本发明的聚合物的总分子量或从本发明的聚合物中去除增强溶解性的基团、或者可替代地既增加总分子量又去除增强溶解性的基团的任何过程,如聚合或缩合。“可固化”是指在某些条件下能够被固化的任何材料。如本文使用的,“间隙”是指在半导体衬底上的旨在用填充间隙的组合物填充的任何孔。
根据以下方法在电子装置的制造中形成芳香族底层,所述方法包括:(a)提供电子装置衬底;(b)将包含一种或多种可固化化合物的涂层组合物层涂覆到所述电子装置衬底的表面上,其中所述一种或多种可固化化合物是包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000;(c)将所述可固化化合物的层固化以形成底层;(d)将光致抗蚀剂层涂覆在所述底层上;(e)通过掩模将所述光致抗蚀剂层暴露于光化辐射;(f)使暴露的光致抗蚀剂层显影以形成抗蚀剂图案;以及(g)将所述图案转移至所述底层以暴露所述电子装置衬底的一部分。接下来,将所述衬底图案化,并且将图案化的底层去除。在一个优选的实施例中,将光致抗蚀剂层直接涂覆在底层上。在可替代的优选的实施例中,在步骤(d)之前,将含硅组合物、有机减反射组合物(BARC)、及其组合中的一种或多种的层直接涂覆在底层上并且任选地固化,以形成中间层,并且然后将光致抗蚀剂层直接涂覆在含硅组合物层、BARC层或各层中的一个或多个上。当使用含硅中间层时,在步骤(f)之后并且在步骤(g)之前将图案转移到所述含硅中间层。
多种多样的电子装置衬底可以在本发明中使用,如:封装衬底,如多芯片模块;平板显示器衬底;集成电路衬底;用于包括有机发光二极管(OLED)的发光二极管(LED)的衬底;半导体晶片;多晶硅衬底;等,其中半导体晶片是优选的。此类衬底典型地由硅、多晶硅、氧化硅、氮化硅、氮氧化硅、锗化硅、砷化镓、铝、蓝宝石、钨、钛、钛-钨、镍、铜和金中的一种或多种构成。合适的衬底可以呈晶片的形式,如用于制造集成电路、光学传感器、平板显示器、集成光学电路、和LED的那些。如本文使用的,术语“半导体晶片”旨在涵盖“半导体衬底”、“半导体装置”以及用于各种互连水平的各种封装物,包括单芯片晶片、多芯片晶片、用于各种水平的封装物、或其他需要焊接连接的组件。此类衬底可以是任何合适的尺寸。优选的晶片衬底直径是200mm至300mm,尽管根据本发明可以适当地使用具有更小和更大直径的晶片。如本文使用的,术语“半导体衬底”包括具有一个或多个半导体层或结构的任何衬底,所述半导体层或结构可以任选地包括半导体装置的活性或可操作部分。半导体装置是指半导体衬底,在其上已经批量制造或正在批量制造至少一种微电子装置。
任选地,可以将粘合促进剂层施加到衬底表面,之后沉积本发明的涂层组合物,随后将其固化以形成底层。如果粘合促进剂是希望的,可以使用用于聚合物膜的任何合适的粘合促进剂,如硅烷,优选有机硅烷如三甲氧基乙烯基硅烷、三乙氧基乙烯基硅烷、六甲基二硅氮烷,或氨基硅烷偶联剂如γ-氨基丙基三乙氧基硅烷。特别合适的粘合促进剂包括从陶氏电子材料公司(Dow Electronic Materials)(马萨诸塞州马尔堡(Marlborough,Massachusetts))可获得的以AP 3000、AP 8000、和AP 9000S名称出售的那些。
可用于本发明的涂层组合物包含一种或多种可固化化合物,其中所述可固化化合物是包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000。对于Z,优选的C1-100-亚烃基部分是C1-50-亚烷基、C2-50-亚烯基、C2-50-亚炔基、以及C5-30-亚芳基,并且更优选C1-20-亚烷基、C2-20-亚烯基、C2-20-亚炔基、以及C5-30-亚芳基。优选的是,Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-50-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4),更优选共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)2、C1-50-亚烃基、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4),又更优选选自共价化学键、O、C(=O)、S、S(=O)2、C5-60-亚芳基、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4),并且甚至更优选选自共价化学键、O、C(=O)、S、C5-60-亚芳基、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4)。R优选选自H、C1-20-烷基、以及C5-30-芳基。优选地,R1和R2各自独立地选自H、OR、和C1-30-烃基,更优选独立地H或C1-30-烃基,并且甚至更优选C10-15-烃基。又更优选地,一个R1、一个R2和Z可以与它们所附接的原子一起形成5元或6元环。对于R1和R2,优选的C1-30-烃基部分是C1-30-烷基、C2-30-烯基、C2-30-炔基、以及C5-30-芳基,并且更优选C1-20-烷基、C1-20-烯基、C2-20-炔基、以及C5-30-芳基。优选的是,a1和a2各自=0至2、更优选0或1。在优选的实施例中,a1=a2,并且甚至更优选地,a1=a2=0或1。本领域技术人员将理解的是,下标n、m1、和m2各自是指重复单元的数目。优选地,m1和m2各自是从1至50、更优选从1至25、并且甚至更优选从1至10。优选的是,n=2至500、更优选2至100、甚至更优选2至50、并且又更优选2至20。
优选的具有式(1)的化合物是其中a1和a2各自是0或1;并且Z=单个共价键、O、亚苯基、亚芘基、亚蒽基、亚苯蒽基(phenanthracenylene)、-O-亚苯基-O-、-O-亚萘基-O-、-C(R3)(R4)、以及-O-亚苯基-C(R3)(R4)-亚苯基-O-的那些。当Z=-C(R3)(R4)-时,一个优选的二价连接基团是具有下式的芴基部分
其中*表示到具有式(1)的部分的附接点。当Z=O时,进一步优选的是,一个R1和一个R2一起形成6元稠合杂环,并且更优选地一个R1和一个R2一起形成具有下式的部分
其中*表示到具有式(1)的部分的附接点。
本发明的可固化化合物典型地使用氯化铜-胺络合物作为催化剂通过具有2-萘酚部分的单体的氧化偶联聚合来制备。优选的催化剂是二-μ-羟基-双-[(N,N,N',N'-四甲基乙二胺)铜(II)]氯化物。此类氧化偶联聚合典型地在室温下在空气中进行。合适的氧化偶联聚合披露于S.Amou等人,“Synthesis of Regiocontrolled Polymer Having 2-Naphthol Unit by CuCl-amine Catalyzed Oxidative Coupling Polymerization[通过CuCl-胺催化的氧化偶联聚合合成区域控制的具有2-萘酚单元的聚合物],”Journal of Polymer Science:Part A:polymer Chemistry[聚合物科学杂志:A辑:聚合物化学],第37卷,第3702-3709页,1999中。可用于制备本发明的可固化聚合物的优选的具有2-萘酚部分的单体是具有式(2)的化合物
其中R1、R2、Z、a1和a2是如以上对于式(1)所描述的,并且其中1位是未取代的。使具有式(2)的单体聚合以形成具有式(1)的重复单元的可固化聚合物。具有式(2)的单体在1位处必须是未取代的。具有式(2)的单体在2-萘酚部分的1位处偶联(即聚合),如在具有式(1)的重复单元中示出的。本发明的可固化聚合物是均聚物,其中所述聚合物的每一端以未反应的2-萘酚部分封端。优选的具有式(2)的单体是具有式(2-1)的那些
其中R1、R2、Z、a1和a2是如以上对于式(1)所描述的,并且其中1位是未取代的。优选的具有式(2-1)的单体是具有式(2a)至(2f)的那些。
单体(2a)至(2f)分别用于制备具有重复单元(1a)至(1f)的聚合物,其中n在每种情况下是指聚合度或重复单元的数目(n=2至1000)。
除了以上描述的一种或多种可固化化合物之外,本发明的涂层组合物可以任选地包含、并且优选地包含一种或多种有机溶剂。合适的有机溶剂是溶解一种或多种可固化化合物的任何有机溶剂,并且优选是常规地用于制造电子装置的有机溶剂。有机溶剂可以单独使用或者可以使用有机溶剂的混合物。合适的有机溶剂包括,但不限于:酮类,如环己酮和2-庚酮;醇类,如3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇、以及1-乙氧基-2-丙醇;醚类,如丙二醇甲醚(PGME)、丙二醇乙醚(PGEE)、乙二醇单甲醚、丙二醇单乙醚、乙二醇单乙醚、丙二醇二甲醚、以及二乙二醇二甲醚、苯甲醚;酯类,如丙二醇单甲醚乙酸酯(PGMEA)、丙二醇单乙醚乙酸酯、乳酸乙酯(EL)、羟基异丁酸甲酯(HBM)、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸叔丁酯、丙酸叔丁酯以及丙二醇单叔丁醚乙酸酯;内酯类,如γ-丁内酯;以及前述的任何组合。优选的溶剂是PGME、PGEE、PGMEA、EL、HBM、及其组合。
本发明的涂层组合物还可以包含一种或多种典型地用于此类涂层的涂层添加剂,如固化剂、交联剂、表面流平剂等。此类任选的添加剂的选择以及它们的量完全在本领域技术人员的能力之内。固化剂典型地以基于总固体从0wt%至20wt%、并且优选从0wt%至3wt%的量存在。交联剂典型地以基于总固体从0wt%至30wt%、并且优选从3wt%至10wt%的量使用。表面流平剂典型地以基于总固体从0wt%至5wt%、并且优选从0wt%至1wt%的量使用。此类任选的添加剂的选择以及它们的使用量在本领域技术人员的能力之内。
固化剂可以任选地用于涂层组合物以帮助沉积的可固化化合物的固化。固化剂是引起可固化化合物在衬底表面上固化的任何组分。优选的固化剂是酸和热酸产生剂。合适的酸包括,但不限于:芳基磺酸,如对-甲苯磺酸;烷基磺酸,如甲磺酸、乙磺酸、和丙磺酸;全氟烷基磺酸,如三氟甲磺酸;以及全氟芳基磺酸。热酸产生剂是在暴露于热时释放酸的任何化合物。热酸产生剂在本领域是众所周知的并且通常是如从康涅狄格州诺沃克金氏工业公司(King Industries,Norwalk,Connecticut)可商购的。示例性热酸产生剂包括但不限于胺封端的强酸,如胺封端的磺酸,如胺封端的十二烷基苯磺酸。本领域技术人员还将理解的是,某些光酸产生剂能够在加热时释放酸并且可以用作热酸产生剂。
任何合适的交联剂可以用于本发明的组合物,前提是此类交联剂具有至少2个、并且优选至少3个能够在合适的条件下(如在酸性条件下)与本发明的芳香族树脂反应产物反应的部分。示例性交联剂包括但不限于酚醛清漆树脂、含环氧基的化合物、三聚氰胺化合物、胍胺化合物、含异氰酸酯的化合物、苯并环丁烯等,并且优选前述中具有2个或更多个、优选3个或更多个、并且更优选4个选自羟甲基、C1-C10烷氧基甲基、以及C2-C10酰氧基甲基的取代基的任一项。合适的交联剂的实例是由式(3)和(4)示出的那些。
此类交联剂在本领域中是众所周知的,并且从多个来源可商购。
本发明的涂层组合物可以任选地包含一种或多种表面流平剂(或表面活性剂)。尽管可以使用任何合适的表面活性剂,但此类表面活性剂典型地是非离子的。示例性非离子表面活性剂是含有亚烷基氧基键联(如亚乙基氧基、亚丙基氧基、或亚乙基氧基和亚丙基氧基键联的组合)的那些。
可以通过任何合适的手段如旋涂、狭缝式模头涂覆、刮涂、幕涂、辊涂、喷涂、浸涂等将本发明的涂层组合物涂覆在电子装置衬底上。优选的是旋涂。在典型的旋涂方法中,将本发明的组合物施加到以500至4000rpm的速率旋转的衬底上持续15至90秒的时间段以在电子装置衬底上获得希望的涂层组合物层。本领域技术人员将理解的是,涂层组合物层的高度可以通过改变旋转速度来调节。
在涂层组合物层被涂覆到衬底上之后,任选地在相对低的温度下将其烘烤以从所述层中去除任何有机溶剂和其他相对易挥发的组分。典型地,所述衬底在80℃至150℃的温度下烘烤,尽管可以使用其他合适的温度。烘烤时间典型地是从10秒至10分钟、并且优选从30秒至5分钟,尽管可以使用更长或更短的时间。当衬底是晶片时,此烘烤步骤可以通过在热板上加热所述晶片来进行。溶剂去除之后,获得了在衬底表面上的可固化化合物的层、膜或涂层。
然后将可固化化合物层充分固化以形成芳香族底层,使得所述膜不与随后施加的涂层(如直接涂覆在芳香族底层上的光致抗蚀剂层或其他层)混杂。底层可以在含氧气氛(如空气)中或在惰性气氛(如氮气)中、并且优选在含氧气氛中固化。使用的固化条件是以下那些:其足以使膜固化,使得它不与随后施加的有机层(如光致抗蚀剂层)混杂,同时仍然保持希望的底层膜的减反射特性(n和k值)、蚀刻选择性、间隙填充、以及平坦化。该固化步骤优选在热板式设备上进行,尽管可以使用烘箱固化来获得等效的结果。典型地,此固化通过在≥150℃、优选≥170℃、并且更优选≥200℃的固化温度下加热底层来进行。选择的固化温度应足以固化芳香族底层。用于固化芳香族底层的合适的温度范围是150℃至400℃、优选从170℃至350℃、并且更优选从200℃至250℃。此固化步骤可以花费10秒至10分钟、优选1至3分钟、并且更优选1至2分钟,尽管可以使用其他合适的时间。
如果固化步骤以使得溶剂和固化副产物的快速释放不允许破坏底层膜质量的方式进行,则初始烘烤步骤可能不是必要的。例如,在相对低的温度下开始并且然后逐渐增加至≥200℃的温度的斜升式烘烤可以产生可接受的结果。在一些情况下,可以优选的是具有两阶段固化工艺,其中第一阶段是小于150℃的较低烘烤温度,并且第二阶段是≥200℃的较高烘烤温度。两阶段固化工艺促进预先存在的衬底表面形貌的均匀填充和平坦化,例如沟槽和通孔的填充。
在固化底层之后,可以将一个或多个处理层,如光致抗蚀剂、含硅层、硬掩膜层、底部减反射涂层(或BARC)层等涂覆在经固化的底层上。例如,可以将光致抗蚀剂直接涂覆(如通过旋涂)在直接在树脂底层上的含硅层或其他中间层的表面上,或者可替代地,所述光致抗蚀剂可以直接涂覆在经固化的底层上。可以适当地使用多种多样的光致抗蚀剂,如用于193nm光刻的那些,如从陶氏电子材料公司(马萨诸塞州马尔堡)可获得的以EpicTM品牌出售的那些。合适的光致抗蚀剂可以是正性显影或负性显影抗蚀剂。涂覆之后,然后使用图案化的光化辐射将光致抗蚀剂层成像(暴露),并且然后使用适当的显影剂将暴露的光致抗蚀剂层显影以提供图案化的光致抗蚀剂层。接下来,通过适当的蚀刻技术将所述图案从光致抗蚀剂层转移到底层。典型地,在此蚀刻步骤期间还将光致抗蚀剂去除。接下来,将图案转移到衬底并且通过本领域已知的适当的蚀刻技术(如通过等离子体蚀刻)将底层去除。在图案化衬底之后,使用常规技术将底层去除。然后根据常规的手段处理电子装置衬底。
经固化的底层可以用作多层抗蚀剂工艺的底部层。在此工艺中,将涂层组合物层涂覆在衬底上并且如以上描述的固化。接下来,将一个或多个中间层涂覆在芳香族底层上。例如,将含硅层或硬掩膜层直接涂覆在芳香族底层上。可以通过旋涂将示例性含硅层如硅-BARC沉积在底层上,随后固化,或者可以通过化学气相沉积(CVD)将无机硅层如SiON、SiN或SiO2沉积在底层上。可以使用任何合适的硬掩膜并且可以通过任何合适的技术将其沉积在底层上,并且固化(适当时)。任选地,可以将有机BARC层直接置于含硅层或硬掩膜层上,并且适当地固化。接下来,将光致抗蚀剂(如在193nm光刻中使用的那些)直接涂覆在含硅层上(在三层工艺中)或直接涂覆在有机BARC层上(在四层工艺中)。然后使用图案化的光化辐射将光致抗蚀剂层成像(暴露),并且然后使用适当的显影剂将暴露的光致抗蚀剂层显影以提供图案化的光致抗蚀剂层。接下来,通过本领域已知的适当的蚀刻技术(如通过等离子体蚀刻)将图案从光致抗蚀剂层转移到直接在其下方的层,产生三层工艺中的图案化的含硅层和四层工艺中的图案化的有机BARC层。如果使用四层工艺,则接下来使用适当的图案转移技术(如等离子体蚀刻)将图案从有机BARC层转移到含硅层或硬掩膜层。在将含硅层或硬掩膜层图案化之后,然后使用适当的蚀刻技术(如O2或CF4等离子体)将芳香族底层图案化。在芳香族底层的蚀刻期间,将任何剩余的图案化的光致抗蚀剂层和有机BARC层去除。接下来,如通过适当的蚀刻技术将图案转移到衬底,这还去除了任何剩余的含硅层或硬掩膜层,随后去除了任何剩余的图案化的芳香族底层,以提供图案化的衬底。
本发明的经固化的底层还可以用于自对准双图案化工艺。在此工艺中,如通过旋涂将本发明的涂层组合物层涂覆在衬底上。去除任何剩余的有机溶剂并且将涂层组合物层固化以形成经固化的底层。将合适的中间层如含硅层涂覆在经固化的底层上。然后如通过旋涂将合适的光致抗蚀剂层涂覆在中间层上。然后使用图案化的光化辐射将光致抗蚀剂层成像(暴露),并且然后使用适当的显影剂将暴露的光致抗蚀剂层显影以提供图案化的光致抗蚀剂层。接下来,通过适当的蚀刻技术将图案从光致抗蚀剂层转移到中间层以及经固化的底层,以暴露衬底的一部分。典型地,在此蚀刻步骤期间还将光致抗蚀剂去除。接下来,将共形含硅层置于图案化的经固化的底层和衬底的暴露部分之上。此类含硅层典型地是常规地通过CVD沉积的无机硅层,如SiON、SiN、或SiO2。此类共形涂层产生在衬底表面的暴露部分上以及在底层图案之上的含硅层,即此类含硅层基本上覆盖了图案化的底层的侧面和顶部。接下来,将含硅层部分地蚀刻(修整)以使图案化的聚亚芳基树脂底层的顶表面和衬底的一部分暴露。在该部分蚀刻步骤之后,衬底上的图案包含多个特征,每个特征包含经固化的底层的线或柱,其中含硅层直接与每个经固化的底层特征的侧边相邻。接下来,如通过蚀刻去除经固化的底层,以使在经固化的底层图案下方的衬底表面暴露,并且在衬底表面上提供图案化的含硅层,其中与图案化的经固化的底层相比,此类图案化的含硅层是双倍的(即,两倍多的线和/或柱)。
本发明的涂层组合物还可用于形成在制造集成电路中的平坦化层、间隙填充层、以及保护层。当用作此类平坦化层、间隙填充层或保护层时,一个或多个插入材料层(如含硅层、其他芳香族树脂层、硬掩膜层等)典型地存在于本发明的涂层组合物的经固化层与任何光致抗蚀剂层之间。典型地,将此类平坦化层、间隙填充层、和保护层最终图案化。根据本发明的间隙填充工艺包括:(a)提供半导体衬底,在所述衬底的表面上具有浮雕图像,所述浮雕图像包括多个待填充的间隙;(b)将间隙填充组合物施加到所述浮雕图像上,其中所述间隙填充组合物包含一种或多种包含具有式(1)的重复单元的可固化化合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000;以及一种或多种有机溶剂;以及(c)在一定温度下加热所述间隙填充组合物以固化一种或多种可固化化合物。本发明的组合物基本上填充、优选填充、并且更优选完全填充半导体衬底中的多个间隙。
本发明的化合物具有良好的间隙填充特性。由本发明的化合物形成的膜具有良好的平坦化和耐溶剂性。
实例1.将单体M-1(4.66g,10mmol)溶解在41.71g的乳酸乙酯中。向该溶液中添加0.23g(0.5mmol)的二-μ-羟基-双-[(N,N,N',N'-四甲基乙二胺)铜(II)]氯化物(Cu-TMEDA),并且将反应混合物在室温下在空气中搅拌24小时。将所述混合物缓慢添加到含有1M盐酸的甲醇的混合物(200mL,v/v=20/80)中。通过过滤收集沉淀产物,并且然后在乙酸乙酯中再溶解。然后将溶液缓慢添加到甲醇中,并且收集沉淀产物,并且在65℃下在真空下干燥2天。以69%产率获得聚合物P-1A(3.2g)。GPC:Mw=1.9K,PDI=1.4。该反应在反应方案1中示出。
实例2.如下重复实例1的程序。将单体M-1(4.66g,10mmol)溶解在43.80g的乳酸乙酯中。向该溶液中添加0.46g(1.0mmol)的Cu-TMEDA,并且将反应混合物在室温下在空气中搅拌24小时。将所述混合物缓慢添加到含有1M盐酸的甲醇的混合物(200mL,v/v=20/80)中。通过过滤收集沉淀产物,并且然后在乙酸乙酯中再溶解。然后将溶液缓慢添加到甲醇中,并且收集沉淀产物,并且在65℃下在真空下干燥2天。以78%产率获得聚合物P-1B(3.61g)。GPC:Mw=3.6K,PDI=1.5。该反应在反应方案1中示出。
反应方案1
实例3.将单体M-2(4.51g,10mmol)溶解在44.73g的乳酸乙酯中。向该溶液中添加0.46g(1.0mmol)的Cu-TMEDA,并且将反应混合物在室温下在开放空气中搅拌24小时。将所述混合物缓慢添加到含有1M盐酸的甲醇的混合物(200mL,v/v=20/80)中。通过过滤收集沉淀产物,并且然后在乙酸乙酯中再溶解。然后将溶液缓慢添加到甲醇中,收集沉淀产物,并且在65℃下在真空下干燥2天,以84%产率产生聚合物P-2(3.79g)。GPC:Mw=2.2K,PDI=1.6。该反应在反应方案2中示出。
反应方案2
实例4.将单体M-3(3.94g,10mmol)溶解在17.64g的乳酸乙酯中。向该溶液中添加0.46g(1.0mmol)的Cu-TMEDA,并且将反应混合物在室温下在空气中搅拌24小时。将所述混合物缓慢添加到含有1M盐酸的甲醇的混合物(200mL,v/v=20/80)中。通过过滤收集沉淀产物,并且然后在乙酸乙酯中再溶解。然后将溶液缓慢添加到甲醇中,收集沉淀产物,并且在65℃下在真空下干燥2天,以79%产率提供3.10g的聚合物P-3。GPC:Mw=195K,PDI=19。该反应在反应方案3中示出。
反应方案3
实例5.将单体M-4(6.35g,10mmol)溶解在27.25g的乳酸乙酯中。向该溶液中添加0.46g(1.0mmol)的Cu-TMEDA,并且将反应混合物在室温下在空气中搅拌24小时。将所述混合物缓慢添加到含有1M盐酸的甲醇的混合物(200mL,v/v=20/80)中。通过过滤收集沉淀产物,并且然后在乙酸乙酯中再溶解。然后将溶液缓慢添加到甲醇中,收集沉淀产物,并且在65℃下在真空下干燥2天,以83%产率得到5.31g的聚合物P-4。GPC:Mw=3.0K,PDI=1.5。该反应在反应方案4中示出。
反应方案4
实例6:溶解性。通过将本发明的化合物以5%固体与PGME和PGMEA中的每种混合来评估溶解性。目视检查以及使用浊度计(Orbeco-Hellige公司)检查这些混合物。如果浊度值小于1,则将化合物评级为可溶的(“S”),并且如果浊度值大于1,则将其评级为不可溶的(“NS”)。结果在表1中报告。如从这些数据可以看出的,本发明的化合物在PGME和PGMEA中的每种中均是可溶的。
表1
实例7:热稳定性。使用来自TA仪器公司(TA-Instrument)的热重分析仪(TGA)Q500在以下条件下评估本发明的化合物的热稳定性:在N2下,以10℃/分钟斜升至700℃;以及在空气下,以10℃/分钟斜升至700℃。材料损失其重量的5%所处的温度(“Td5%”)在表2中报告。
表2
实例8.测量耐溶剂剥离性,作为膜交联的指示。在PGMEA中以4.5%固体制备本发明的化合物的组合物。使用ACT-8 Clean Track(东京电子公司(Tokyo Electron Co.))以1500rpm的速率将每种组合物旋涂在8”(200mm)硅晶片上,并且然后在350℃下烘烤60秒以形成膜。使用来自Therma-Wave公司的OptiProbeTM测量初始膜厚度。接下来,将商业脱膜剂(remover)PGMEA施加到每种膜上持续90秒,随后在105℃下进行剥离后烘烤步骤持续60秒。再次测量在剥离后烘烤之后每种膜的厚度,以确定膜厚度损失的量。在与脱膜剂接触之前和之后的膜厚度的差在表3中以剩余膜厚度的百分比报告。如从数据可以看出的,由本发明的聚合物P-3和P-4形成的膜在与脱膜剂接触之后保留大于99%的它们的厚度。
表3
条目编号 | 聚合物 | %剩余膜 |
1 | P-1A | 32.8 |
2 | P-1B | 39.7 |
3 | P-2 | 4.7 |
4 | P-3 | >99 |
5 | P-4 | >99 |
实例9.评估本发明的聚合物以确定其间隙填充特性。在CNSE Nano-FAB(纽约奥尔巴尼(Albany,NY))创建间隙填充模板。所述模板具有100nm的SiO2膜厚度、以及各种间距和图案。在用本发明的组合物涂覆试样之前,将模板试样在150℃下烘烤60秒作为脱水烘烤。使用ACT-8Clean Track(东京电子公司)旋转涂布机以及1500rpm+/-200rpm的旋转速率将每种涂层组合物(PGMEA中的4.5%固体)涂覆在模板试样上。固化之后的目标膜厚度是100nm,并且相应地调节组合物稀释度以近似地得到固化之后的目标膜厚度。通过将晶片置于热板上在350℃下持续60秒来将膜固化。使用Hitachi S4800 SEM(来自日立高新技术公司(Hitachi High Technologies))采集经涂覆的试样的横截面扫描电子显微镜(SEM)图像。膜的平坦化质量是从SEM图像使用日立离线CD测量软件或CDM软件通过测量通孔上的膜厚度与沟槽上的膜厚度的差(ΔFT)获得的。具有ΔFT<20nm的膜被认为具有“良好的”平坦化并且具有ΔFT>20nm的膜被认为具有“差的”平坦化。间隙填充通过目视检查SEM图像以观察沟槽图案中是否存在任何空隙或气泡来评估。在沟槽图案中不具有空隙的膜被认为具有“良好的”间隙填充并且在沟槽图案中具有空隙的膜被认为具有“差的”间隙填充。这些结果在表4中报告。表4
样品编号 | 聚合物 | 平坦化 | 间隙填充 |
1 | P-1A | 差 | 差 |
2 | P-1B | 差 | 差 |
3 | P-2 | 差 | 差 |
4 | P-3 | 良好 | 良好 |
5 | P-4 | 良好 | 良好 |
Claims (8)
1.一种方法,其包括:(a)提供电子装置衬底;(b)将包含一种或多种可固化化合物的涂层组合物层涂覆到所述电子装置衬底的表面上,其中所述一种或多种可固化化合物是包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000;(c)将所述可固化化合物的层固化以形成底层;(d)将光致抗蚀剂层涂覆在所述底层上;(e)通过掩模将所述光致抗蚀剂层暴露于光化辐射;(f)使暴露的光致抗蚀剂层显影以形成抗蚀剂图案;以及(g)将所述图案转移至所述底层以暴露所述电子装置衬底的一部分。
2.如权利要求1所述的方法,其进一步包括将所述衬底图案化;以及然后去除所述图案化的底层的步骤。
3.如权利要求1所述的方法,其进一步包括在步骤(d)之前将含硅层、有机减反射涂层及其组合中的一个或多个涂覆在所述底层上的步骤。
4.如权利要求3所述的方法,其进一步包括在步骤(f)之后并且在步骤(g)之前,将所述图案转移到所述含硅层、所述有机减反射涂层及其组合中的一个或多个上的步骤。
5.如权利要求1所述的方法,其中,所述涂层组合物进一步包含有机溶剂、固化剂、和表面流平剂中的一种或多种。
7.一种包括电子装置衬底的电子装置,其在所述电子装置衬底的表面上具有包含作为聚合单元的一种或多种可固化化合物的聚合物层,其中所述一种或多种可固化化合物是包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000。
8.一种包含具有式(1)的重复单元的聚合物
其中Z是共价化学键或选自以下各项的二价连接基团:O、C(=O)、S、S(=O)、S(=O)2、N(R)、C1-100-亚烃基、取代的C1-100-亚烃基、-O-(C1-20-亚烷基-O-)m1、-O-(C5-60-亚芳基-O-)m2、以及C(R3)(R4);R选自H、C1-20-烷基、C5-30-芳基、以及C2-20-不饱和的脂肪族部分;每个R1和每个R2独立地选自H、OR、C1-30-烃基、取代的C1-30-烃基、-C(=O)-O-R5、SR、S(=O)R、S(=O)2R、N(R5)(R6)、以及N(R7)C(=O)R5;一个R1和一个R2以及Z可以与它们所附接的原子一起形成5元至6元环;R3和R4独立地选自C1-20-烷基和C5-30-芳基;R3和R4可以与它们所附接的碳一起形成5元或6元环,所述环可以与一个或多个芳香族环稠合,并且所述5元或6元环任选地被取代;R5和R6独立地是C1-20-烷基或C5-30-芳基;R7是H或R6;R5和R6可以与它们所附接的原子一起形成5元至6元环;a1和a2各自是从0至5;m1和m2各自=1至100;并且n=2至1000。
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