CN101617010B - 有机硅涂料组合物 - Google Patents
有机硅涂料组合物 Download PDFInfo
- Publication number
- CN101617010B CN101617010B CN2008800056175A CN200880005617A CN101617010B CN 101617010 B CN101617010 B CN 101617010B CN 2008800056175 A CN2008800056175 A CN 2008800056175A CN 200880005617 A CN200880005617 A CN 200880005617A CN 101617010 B CN101617010 B CN 101617010B
- Authority
- CN
- China
- Prior art keywords
- substituted
- replace
- group
- coating
- alkyl
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 239000004447 silicone coating Substances 0.000 title description 3
- 238000004132 cross linking Methods 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- -1 amber acid radical Chemical class 0.000 claims description 70
- 239000000126 substance Substances 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 38
- 239000011248 coating agent Substances 0.000 claims description 27
- 238000000576 coating method Methods 0.000 claims description 27
- 150000002500 ions Chemical class 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910020175 SiOH Inorganic materials 0.000 claims description 11
- 229910008051 Si-OH Inorganic materials 0.000 claims description 10
- 229910006358 Si—OH Inorganic materials 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229920002120 photoresistant polymer Polymers 0.000 claims description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000003384 imaging method Methods 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910018125 Al-Si Inorganic materials 0.000 claims description 3
- 229910018520 Al—Si Inorganic materials 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 229910004541 SiN Inorganic materials 0.000 claims description 3
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- 229910008938 W—Si Inorganic materials 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- CSUMJWUPRLYQSZ-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC=C1C(C=CC=C1)=C1C1=CC=CC=C1.S Chemical compound CC(C)(C)C(C=C1)=CC=C1C(C=CC=C1)=C1C1=CC=CC=C1.S CSUMJWUPRLYQSZ-UHFFFAOYSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- 229910009257 Y—Si Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000001312 dry etching Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical group C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 claims description 2
- 239000012953 triphenylsulfonium Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- 125000003010 ionic group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 5
- 230000003667 anti-reflective effect Effects 0.000 abstract description 4
- 238000000206 photolithography Methods 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 31
- 235000002639 sodium chloride Nutrition 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 17
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical group COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 11
- 235000012431 wafers Nutrition 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 9
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000010442 halite Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 150000003973 alkyl amines Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000005259 triarylamine group Chemical group 0.000 description 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229920001558 organosilicon polymer Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000007598 dipping method Methods 0.000 description 4
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000005385 peroxodisulfate group Chemical group 0.000 description 4
- 238000000710 polymer precipitation Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- UAXSFPJRIUOQPX-UHFFFAOYSA-N CC(C)(C)C1=C(C(C(O)=O)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1.S Chemical compound CC(C)(C)C1=C(C(C(O)=O)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1.S UAXSFPJRIUOQPX-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 150000001539 azetidines Chemical class 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 150000002496 iodine Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940017219 methyl propionate Drugs 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical group CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 150000004885 piperazines Chemical class 0.000 description 3
- 150000003053 piperidines Chemical class 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 150000003233 pyrroles Chemical class 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 125000005270 trialkylamine group Chemical group 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical class C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 3
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical group COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- GBQYMXVQHATSCC-UHFFFAOYSA-N 3-triethoxysilylpropanenitrile Chemical compound CCO[Si](OCC)(OCC)CCC#N GBQYMXVQHATSCC-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- NJGLOOWONLTQTG-UHFFFAOYSA-N C[SiH](C)O[Si](C)(C)C.Cl.Cl Chemical compound C[SiH](C)O[Si](C)(C)C.Cl.Cl NJGLOOWONLTQTG-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical group CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- RGFNRWTWDWVHDD-UHFFFAOYSA-N sec-butyl ester of butyric acid Natural products CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- LPSWFOCTMJQJIS-UHFFFAOYSA-N sulfanium;hydroxide Chemical compound [OH-].[SH3+] LPSWFOCTMJQJIS-UHFFFAOYSA-N 0.000 description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- SVTBMSDMJJWYQN-RXMQYKEDSA-N (4r)-2-methylpentane-2,4-diol Chemical compound C[C@@H](O)CC(C)(C)O SVTBMSDMJJWYQN-RXMQYKEDSA-N 0.000 description 1
- 239000001605 (5-methyl-2-propan-2-ylcyclohexyl) acetate Substances 0.000 description 1
- AUEJBKCWXPYRGZ-UHFFFAOYSA-N 1,1'-biphenyl diethoxysilane Chemical compound C(C)O[SiH2]OCC.C1(=CC=CC=C1)C1=CC=CC=C1 AUEJBKCWXPYRGZ-UHFFFAOYSA-N 0.000 description 1
- FXJRXJXSLXNGBY-UHFFFAOYSA-N 1,1,3,3-tetrabutylguanidine Chemical compound CCCCN(CCCC)C(=N)N(CCCC)CCCC FXJRXJXSLXNGBY-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RQUBQBFVDOLUKC-UHFFFAOYSA-N 1-ethoxy-2-methylpropane Chemical compound CCOCC(C)C RQUBQBFVDOLUKC-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- FJJYYHWOYYNABG-UHFFFAOYSA-N 1-tert-butyl-2,3-diphenylbenzene Chemical compound C=1C=CC=CC=1C=1C(C(C)(C)C)=CC=CC=1C1=CC=CC=C1 FJJYYHWOYYNABG-UHFFFAOYSA-N 0.000 description 1
- WQVIVQDHNKQWTM-UHFFFAOYSA-N 1-tert-butyl-4-iodobenzene Chemical compound CC(C)(C)C1=CC=C(I)C=C1 WQVIVQDHNKQWTM-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- TWTABCWDZNSIFD-UHFFFAOYSA-N 2-methylpropanoic acid hydrate Chemical compound O.CC(C)C(O)=O.CC(C)C(O)=O TWTABCWDZNSIFD-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- BTWSDELVRHNNLR-UHFFFAOYSA-N 2-propoxyethyl propanoate Chemical compound CCCOCCOC(=O)CC BTWSDELVRHNNLR-UHFFFAOYSA-N 0.000 description 1
- JUDMQYNFOKUYKQ-UHFFFAOYSA-N 2-propoxyhexanoic acid Chemical compound CCCCC(C(O)=O)OCCC JUDMQYNFOKUYKQ-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical group 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
- VHGIMAJUMPMTFZ-UHFFFAOYSA-N 3-propoxybutyl propanoate Chemical compound CCCOC(C)CCOC(=O)CC VHGIMAJUMPMTFZ-UHFFFAOYSA-N 0.000 description 1
- OYNJSBBPNFNGNK-UHFFFAOYSA-N 3-propoxypropyl acetate Chemical compound CCCOCCCOC(C)=O OYNJSBBPNFNGNK-UHFFFAOYSA-N 0.000 description 1
- VOOOYSCXEXMXGY-UHFFFAOYSA-N 3-propoxypropyl propanoate Chemical compound CCCOCCCOC(=O)CC VOOOYSCXEXMXGY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- WGINUBKWLUSQGI-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=CC=C1.[I] Chemical compound C1(=CC=CC=C1)C1=CC=CC=C1.[I] WGINUBKWLUSQGI-UHFFFAOYSA-N 0.000 description 1
- JACFXKQPAFJQLQ-UHFFFAOYSA-N CCNCC.CCO[SiH2]OCC Chemical compound CCNCC.CCO[SiH2]OCC JACFXKQPAFJQLQ-UHFFFAOYSA-N 0.000 description 1
- KAOLRQUUXBEACM-UHFFFAOYSA-N CCNCC.CO[SiH2]OC Chemical compound CCNCC.CO[SiH2]OC KAOLRQUUXBEACM-UHFFFAOYSA-N 0.000 description 1
- MVHZHMKEBJJTCH-UHFFFAOYSA-N CN(C)C.CO[SiH3] Chemical group CN(C)C.CO[SiH3] MVHZHMKEBJJTCH-UHFFFAOYSA-N 0.000 description 1
- GFTMNZCZQGIDDK-UHFFFAOYSA-N Cl[SiH3].CC1=C(C=CC=C1)C1=CC=CC=C1 Chemical compound Cl[SiH3].CC1=C(C=CC=C1)C1=CC=CC=C1 GFTMNZCZQGIDDK-UHFFFAOYSA-N 0.000 description 1
- XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- XHXUANMFYXWVNG-ADEWGFFLSA-N Menthyl acetate Natural products CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical class COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SWUMZLCXZILNER-UHFFFAOYSA-N P.CF Chemical compound P.CF SWUMZLCXZILNER-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-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
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- OEGMRKQMHYKWBS-UHFFFAOYSA-M [OH-].[I+] Chemical compound [OH-].[I+] OEGMRKQMHYKWBS-UHFFFAOYSA-M 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- DJZCQTRVVBDSRT-UHFFFAOYSA-N azane;2,2,3-trimethylbutanoic acid Chemical compound N.CC(C)C(C)(C)C(O)=O DJZCQTRVVBDSRT-UHFFFAOYSA-N 0.000 description 1
- LPAMDXFWRUPCGM-UHFFFAOYSA-N azanium 2,2,3-tributylheptanoate Chemical compound CCCCC(CCCC)C(CCCC)(CCCC)C(=O)[O-].[NH4+] LPAMDXFWRUPCGM-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical class CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 1
- URBZEXMYYYABCQ-UHFFFAOYSA-N butyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCCC URBZEXMYYYABCQ-UHFFFAOYSA-N 0.000 description 1
- VUEYQLJAKGLDNR-UHFFFAOYSA-N butyl 2-ethoxyacetate Chemical compound CCCCOC(=O)COCC VUEYQLJAKGLDNR-UHFFFAOYSA-N 0.000 description 1
- MENWVOUYOZQBDM-UHFFFAOYSA-N butyl 3-hydroxypropanoate Chemical compound CCCCOC(=O)CCO MENWVOUYOZQBDM-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CXUFAAUKTHVLAL-UHFFFAOYSA-N butylphosphanium;chloride Chemical compound [Cl-].CCCC[PH3+] CXUFAAUKTHVLAL-UHFFFAOYSA-N 0.000 description 1
- ZBBKCJXETVKDOI-UHFFFAOYSA-N butylphosphanium;hydroxide Chemical class [OH-].CCCC[PH3+] ZBBKCJXETVKDOI-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- MEUXNEGJODESOX-UHFFFAOYSA-N chloro-cyclohexyl-dimethylsilane Chemical compound C[Si](C)(Cl)C1CCCCC1 MEUXNEGJODESOX-UHFFFAOYSA-N 0.000 description 1
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 description 1
- HXVPUKPVLPTVCQ-UHFFFAOYSA-N chloro-dimethyl-propylsilane Chemical compound CCC[Si](C)(C)Cl HXVPUKPVLPTVCQ-UHFFFAOYSA-N 0.000 description 1
- AVDUEHWPPXIAEB-UHFFFAOYSA-N chloro-ethyl-dimethylsilane Chemical compound CC[Si](C)(C)Cl AVDUEHWPPXIAEB-UHFFFAOYSA-N 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000012940 design transfer Methods 0.000 description 1
- HZLIIKNXMLEWPA-UHFFFAOYSA-N diethoxy(dipropyl)silane Chemical compound CCC[Si](CCC)(OCC)OCC HZLIIKNXMLEWPA-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- JVUVKQDVTIIMOD-UHFFFAOYSA-N dimethoxy(dipropyl)silane Chemical compound CCC[Si](OC)(OC)CCC JVUVKQDVTIIMOD-UHFFFAOYSA-N 0.000 description 1
- QYMFNZIUDRQRSA-UHFFFAOYSA-N dimethyl butanedioate;dimethyl hexanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCC(=O)OC.COC(=O)CCCC(=O)OC.COC(=O)CCCCC(=O)OC QYMFNZIUDRQRSA-UHFFFAOYSA-N 0.000 description 1
- MXTMXRYBYWOAGX-UHFFFAOYSA-N dimethyl(diphenyl)azanium Chemical compound C=1C=CC=CC=1[N+](C)(C)C1=CC=CC=C1 MXTMXRYBYWOAGX-UHFFFAOYSA-N 0.000 description 1
- ZIDTUTFKRRXWTK-UHFFFAOYSA-N dimethyl(dipropoxy)silane Chemical compound CCCO[Si](C)(C)OCCC ZIDTUTFKRRXWTK-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- AVBCBOQFOQZNFK-UHFFFAOYSA-N dipropoxy(dipropyl)silane Chemical compound CCCO[Si](CCC)(CCC)OCCC AVBCBOQFOQZNFK-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- SVBSJWKYFYUHTF-UHFFFAOYSA-N ethyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCC SVBSJWKYFYUHTF-UHFFFAOYSA-N 0.000 description 1
- UKDLORMZNPQILV-UHFFFAOYSA-N ethyl 3-hydroxypropanoate Chemical compound CCOC(=O)CCO UKDLORMZNPQILV-UHFFFAOYSA-N 0.000 description 1
- KNFXXAGQEUUZAZ-UHFFFAOYSA-N ethyl ethaneperoxoate Chemical compound CCOOC(C)=O KNFXXAGQEUUZAZ-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- KUCGHDUQOVVQED-UHFFFAOYSA-N ethyl(tripropoxy)silane Chemical compound CCCO[Si](CC)(OCCC)OCCC KUCGHDUQOVVQED-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- QHGSGZLLHBKSAH-UHFFFAOYSA-N hydridosilicon Chemical class [SiH] QHGSGZLLHBKSAH-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- JYVNDCLJHKQUHE-UHFFFAOYSA-N hydroxymethyl acetate Chemical compound CC(=O)OCO JYVNDCLJHKQUHE-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940024423 isopropyl isobutyrate Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- BKFQHFFZHGUTEZ-UHFFFAOYSA-N methyl 2-butoxyacetate Chemical class CCCCOCC(=O)OC BKFQHFFZHGUTEZ-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical class CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical class COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- VABBJJOSOCPYIT-UHFFFAOYSA-N methyl 2-methoxypropanoate Chemical class COC(C)C(=O)OC VABBJJOSOCPYIT-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical class CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical class COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 1
- DMQRGHBKAIMHKR-UHFFFAOYSA-N methylphosphane hydrate Chemical class [OH-].C[PH3+] DMQRGHBKAIMHKR-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- MQFOBQNNBFJYDU-UHFFFAOYSA-N phosphane;propanoic acid Chemical compound [PH4+].CCC([O-])=O MQFOBQNNBFJYDU-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- HNYIJJOTPSKGJM-UHFFFAOYSA-N propoxymethyl acetate Chemical compound CCCOCOC(C)=O HNYIJJOTPSKGJM-UHFFFAOYSA-N 0.000 description 1
- GFKFCNLAMLYNCQ-UHFFFAOYSA-N propoxymethyl propanoate Chemical compound CCCOCOC(=O)CC GFKFCNLAMLYNCQ-UHFFFAOYSA-N 0.000 description 1
- LVDAGIFABMFXSJ-UHFFFAOYSA-N propyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCC LVDAGIFABMFXSJ-UHFFFAOYSA-N 0.000 description 1
- ADOFEJQZDCWAIL-UHFFFAOYSA-N propyl 2-ethoxyacetate Chemical compound CCCOC(=O)COCC ADOFEJQZDCWAIL-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- KNCDNPMGXGIVOM-UHFFFAOYSA-N propyl 3-hydroxypropanoate Chemical compound CCCOC(=O)CCO KNCDNPMGXGIVOM-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver nitrate Substances [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PQLLEAYSRJFMFF-UHFFFAOYSA-N sulfuric acid;hydroiodide Chemical class I.OS(O)(=O)=O PQLLEAYSRJFMFF-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 description 1
- QNOAKQGNSWGYOE-UHFFFAOYSA-M tetraethylazanium;acetate;tetrahydrate Chemical compound O.O.O.O.CC([O-])=O.CC[N+](CC)(CC)CC QNOAKQGNSWGYOE-UHFFFAOYSA-M 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- SUBUUGVBEKEFGW-UHFFFAOYSA-N tetramethylazanium;azide Chemical compound [N-]=[N+]=[N-].C[N+](C)(C)C SUBUUGVBEKEFGW-UHFFFAOYSA-N 0.000 description 1
- GTDKXDWWMOMSFL-UHFFFAOYSA-M tetramethylazanium;fluoride Chemical compound [F-].C[N+](C)(C)C GTDKXDWWMOMSFL-UHFFFAOYSA-M 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials For Photolithography (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
本发明涉及一种组合物，其包含：(a)具有至少一种式(I)的重复单元的聚合物：其中R1是不可水解基团和n是1-3的整数；和(b)交联催化剂。该组合物可用于形成低k介电常数材料以及光刻工业用的具有抗反射性能的硬掩模和底层材料。
Description
发明背景
本发明一般地涉及高硅含量树脂组合物，其可用于形成薄膜热固性材料、可用于形成低k介电常数材料以及光刻工业用的具有抗反射性能的硬掩模和底层材料。
随着微电子器件的尺寸变得更小，充分地开发用于它们制造的材料的物理性能的重要性变得更加必要。用于使金属线、通孔和电子部件彼此绝缘的介电材料特别如此，这归因于这些材料对电容所作的贡献。二氧化硅已经在工业中被用作制造器件的介电材料近三十年，但由于其相对高的介电常数(k-4.1)而因此在未来可能变得较为不合适。然而，近来硅氧烷进入了使用低介电常数绝缘层和表现出抗反射性能的图案转移硬掩模的微刻制造中。
另外，在目前的常规半导体制造中，为了防止光反射透过光致抗蚀剂、从基底上反射并回到光致抗蚀剂中，在该情况下其可能与入射光干涉并且因此导致光致抗蚀剂的不均匀曝光，常规地在沉积或旋涂光致抗蚀剂到上面之前可以沉积一个或多个抗反射层。在不存在抗反射涂层的情况下，被反射和入射曝光辐射的干涉可能造成驻波效应，其会破坏通过光致抗蚀剂层的厚度的辐射均匀性。遍布整个成像区域的反射率的变化可能对被设计具有类似尺寸的特征造成不希望的线宽变化。
发明概述
本发明涉及一种组合物，其包含：
(a)具有至少一种下式的重复单元的聚合物：
其中R1是不可水解基团和n是1-3的整数；和(b)交联催化剂。该交联催化剂可由式Z+A-表示，其中Z是选自以下的阳离子：四烷基铵、四烷基鏻、三烷基单芳基铵、三烷基单芳基鏻、二烷基二芳基铵、二烷基二芳基鏻、单烷基三芳基铵、单烷基三芳基鏻、四芳基铵、四芳基鏻、未取代或取代的碘鎓和未取代或取代的锍，和A是含有选自以下的基团的阴离子：卤化物(halide)、次石盐(hypohalite)、石盐(halite)、卤酸根(halate)、高卤酸根(perhalate)、氢氧化物、单羧酸盐离子、二羧酸盐离子、碳酸根、碳酸氢根、硅醇盐(silanolate)、醇盐(alkoxide)、芳基氧化物(aryloxide)、硝酸根、叠氮(azide)、过氧单硫酸根、过氧二硫酸根、磷酸二氢根、磷酸根、硫酸根、硫酸氢根、磺酸根和胍，以及其水合物，和其混合物，或者交联催化剂可以是在小于或等于约500℃的温度下分解的硫酸产生剂，其可以包括硫酸、以下物质的硫酸氢盐或硫酸盐：三烷基胺、未取代或取代的二烷基单环烷基胺、未取代或取代的单烷基二环烷基胺、未取代或取代的三环烷基胺、三芳基胺、未取代或取代的二芳基单烷基胺、未取代或取代的单芳基二烷基胺、未取代或取代的三芳基胺、未取代或取代的氮杂环丙烷、未取代或取代的氮杂环丁烷、未取代或取代的吡咯、未取代或取代的吡啶、未取代或取代的哌啶、或者未取代或取代的哌嗪，例如三乙胺硫酸氢盐、三丁胺硫酸氢盐、哌嗪硫酸盐等。
发明详述
本发明涉及一种组合物，其包含：
(a)具有至少一种下式的重复单元的聚合物：
其中R1是不可水解基团和n是1-3的整数；和(b)交联催化剂。该交联催化剂可由式Z+A-表示，其中Z是选自以下的阳离子：四烷基铵、四烷基鏻、三烷基单芳基铵、三烷基单芳基鏻、二烷基二芳基铵、二烷基二芳基鏻、单烷基三芳基铵、单烷基三芳基鏻、四芳基铵、四芳基鏻、未取代或取代的碘鎓和未取代或取代的锍，和A是含有选自以下的基团的阴离子：卤化物、次石盐、石盐、卤酸根、高卤酸根、氢氧根、单羧酸盐离子、二羧酸盐离子、碳酸根、碳酸氢根、硅醇盐、醇盐、芳基氧化物、硝酸根、叠氮、过氧单硫酸根、过氧二硫酸根、磷酸二氢根、磷酸根、硫酸根、硫酸氢根、磺酸根和胍，以及其水合物，和其混合物，或者交联催化剂可以是在小于或等于约500℃的温度下分解的硫酸产生剂，其可以包括硫酸、以下物质的硫酸氢盐或硫酸盐：三烷基胺、未取代或取代的二烷基单环烷基胺、未取代或取代的单烷基二环烷基胺、未取代或取代的三环烷基胺、三芳基胺、未取代或取代的二芳基单烷基胺、未取代或取代的单芳基二烷基胺、未取代或取代的三芳基胺、未取代或取代的氮杂环丙烷、未取代或取代的氮杂环丁烷、未取代或取代的吡咯、未取代或取代的吡啶、未取代或取代的哌啶、或者未取代或取代的哌嗪，例如三乙胺硫酸氢盐、三丁胺硫酸氢盐、哌嗪硫酸盐等。
可固化的有机硅聚合物通过不同的机理固化，这些机理主要包括通过与Si直接相连的反应性基团例如硅醇(SiOH)、烷氧基硅烷(SiOR)、卤代硅烷、乙烯基硅烷、SiH等，其中通过那些反应性基团进行固化，并且为缩合、水解/缩合、加成等，和通过其反应活性不直接依赖于Si的反应性基团例如乙烯基、氢化物、胺、环氧、甲醇、甲基丙烯酸酯/丙烯酸酯、巯基等，其中通过这些官能团以与带有相同官能团的不含Si的有机涂料组合物类似的方式进行固化。
可固化的有机硅聚合物已在半导体工业中被广泛用作低k材料、硬掩模、底层、抗反射涂层等。用于该领域的大部分有机硅聚合物利用SiOH/SiOR基团来实现高度交联的膜。然而，含有SiOH基团的有机硅聚合物通常具有一个缺陷-在储存期间由SiOH基团的缩合造成的不充足的稳定性。如果水存在，则其可能使SiOR基团水解，导致在储存期间类似的不稳定性。申请人能够采用本发明克服这些缺陷，本发明提供了具有良好的固化性能和由于缺乏SiOH/SiOR基团而具有优异的储存稳定性的有机硅涂料组合物。
术语“可水解基团”是指在合适的条件下能够直接进行缩合反应或者在合适的条件下能够水解由此产生能够进行缩合反应的化合物的基团。
因此，本发明中使用的术语“不可水解基团”是指在合适的条件下不能直接进行缩合反应或者在上面列出的用于使可水解基团水解的条件下不能水解的基团。
不可水解基团的实例包括，但不限于，氢、未取代或取代的烷基、未取代或取代的单环烷基或多环烷基、未取代或取代的单环或多环芳基、未取代或取代的单环或多环芳烷基、羧基和甲醇。可用于取代上述结构部分的基团的实例包括羧基、氰基、卤素等。
具有通式R1 mSi(X)4-m的硅氧烷单体可用于本发明聚合物的最初形成，其中每一R1独立地是未取代或取代的烷基或者未取代或取代的芳基，X是卤素或OR1，和m是0-3的整数。这类单体的实例包括，例如(i)当m＝0时，四烷氧基硅烷例如四甲氧基硅烷、四乙氧基硅烷、四丙氧基硅烷和四丁氧基硅烷；(ii)当m＝1时，单烷基三烷氧基硅烷例如单甲基三甲氧基硅烷、单甲基三乙氧基硅烷、单甲基三丙氧基硅烷、单乙基三甲氧基硅烷、单乙基三乙氧基硅烷、单乙基三丙氧基硅烷、单丙基三甲氧基硅烷、2-氰基乙基三乙氧基硅烷、3-氯丙基三甲氧基硅烷、单丙基三乙氧基硅烷；和单苯基三烷氧基硅烷例如单苯基三甲氧基硅烷和单苯基三乙氧基硅烷；(iii)当m＝2时，二烷基二烷氧基硅烷例如二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、二甲基二丙氧基硅烷、二乙基二甲氧基硅烷、二乙基二乙氧基硅烷、二乙基二丙氧基硅烷、二丙基二甲氧基硅烷、二丙基二乙氧基硅烷和二丙基二丙氧基硅烷；和二苯基二烷氧基硅烷例如二苯基二甲氧基硅烷和二苯基二乙氧基硅烷；和(iv)当m＝3时，三烷基单烷氧基硅烷例如三甲基甲氧基硅烷、三乙基乙氧基硅烷等。
在形成上述聚合物之后，可能含有Si-OH和Si-OR1基团和有时Si-卤素的聚合物然后被水解，例如通过使其与水接触(例如沉淀到水中)，这造成任何Si-OR1结构部分和，如果存在，Si-卤素水解成Si-OH。仅具有Si-OH基团的沉淀的聚合物然后进一步与封端剂反应，该封端剂进一步与聚合物中的Si-OH结构部分反应直到任何Si-OH基团的存在不被观察到。封端剂的实例包括，但不限于，具有式Ra 3Si(Rb)的化合物，其中每一Ra独立地是未取代或取代的烷基或者未取代或取代的芳基，和Rb是ORa或卤素，或者具有式(R10)3Si-Y-Si(R10)3的化合物，其中每一R10选自未取代或取代的C1-4烷基和未取代或取代的C1-4烷氧基，和Y是选自-O-和-NR11-的连接基团，其中R11是氢或者C1-10未取代和取代的支化或直链烷基，例如未取代或取代的三烷基单卤代硅烷、二烷基单芳基单卤代硅烷和单烷基二芳基单卤代硅烷等；例如双氯甲基四甲基二硅氧烷、3-氰基丙基二甲基氯硅烷、1，3-双(3-羧基丙基)四甲基二硅氧烷、三甲基氯硅烷、三乙基氯硅烷、二甲基(乙基)氯硅烷、苯基二甲基甲氧基硅烷、三甲基乙氧基硅烷、二甲基(环己基)氯硅烷、二甲基(苯基)氯硅烷和甲基(二苯基)氯硅烷等。
本发明组合物的另一种组分是交联催化剂。交联催化剂的实例，其在下面进一步描述，包括四烷基氢氧化铵和/或四烷基氢氧化鏻以及三烷基氢氧化锍和二烷基氢氧化碘鎓。交联催化剂可以是四烷基氢氧化铵和酸的盐，和/或四烷基氢氧化鏻和酸的盐，和/或三取代的(用烷基、芳基或其混合物取代)氢氧化锍和酸的盐，和/或二芳基氢氧化碘鎓和酸的盐。酸可以是例如无机酸，如硫酸、磷酸、盐酸等，有机酸如甲酸、乙酸、对-甲苯磺酸、草酸等，或者含有酸基的聚合物。酸可以是含Si的，例如1，3-双(3-羧基丙基)四甲基二硅氧烷。
交联催化剂可由式Z+A-表示，其中Z+是选自以下的阳离子：四烷基铵、四烷基鏻、三烷基单芳基铵、三烷基单芳基鏻、二烷基二芳基铵、二烷基二芳基鏻、单烷基三芳基铵、单烷基三芳基鏻、四芳基铵、四芳基鏻、未取代或取代的碘鎓和未取代或取代的锍，和A是含有选自以下的基团的阴离子：卤化物、次石盐、石盐、卤酸根、高卤酸根、氢氧根、单羧酸盐离子、二羧酸盐离子、碳酸根、碳酸氢根、硅醇盐、醇盐、芳基氧化物、硝酸根、叠氮、过氧单硫酸根、过氧二硫酸根、磷酸二氢根、磷酸根、硫酸根、硫酸氢根、磺酸根和胍，以及其水合物，和其混合物。
上述阳离子的实例包括：四甲基铵、四丁基铵、四苯基铵、四甲基鏻、四苯基鏻、三甲基苯基铵、三甲基苯基鏻、二甲基二苯基铵、二甲基二苯基鏻、三苯基锍、(4-叔丁基苯基)二苯基锍、二苯基碘鎓和双(4-叔丁基苯基)碘鎓等。
对于阴离子，该阴离子将含有上述基团之一，或者该基团本身将是阴离子。
单羧酸盐离子是指含有一个其中氢被除去的羧基的有机酸的阴离子，并且包括例如乙酸根、甲酸根、丙酸根等。二羧酸盐离子是指含有两个其中一个或两个氢被除去的羧基的有机酸的阴离子，并且包括琥珀酸根、丙二酸根、单丙二酸根(其中仅一个氢被除去)、己二酸根等。
交联催化剂优选选自：四甲基氢氧化铵、四甲基氢氧化鏻、四甲基甲酸铵、四甲基甲酸鏻、四甲基乙酸铵、四甲基乙酸鏻、四甲基丙酸铵、四甲基丙酸鏻、四甲基氟化铵、四甲基氟化鏻、四甲基氯化铵、四甲基氯化鏻、四甲基碳酸铵、四甲基碳酸鏻、四甲基胍、四甲基过氧单硫酸铵、四甲基过氧单硫酸鏻、四甲基过氧二硫酸铵、四甲基过氧二硫酸鏻、四甲基叠氮化铵、四甲基叠氮化鏻、四丁基氢氧化铵、四丁基氢氧化鏻、四丁基甲酸铵、四丁基甲酸鏻、四丁基乙酸铵、四丁基乙酸鏻、四丁基丙酸铵、四丁基丙酸鏻、四丁基氟化铵、四丁基氟化鏻、四丁基氯化铵、四丁基氯化鏻、四丁基碳酸铵、四丁基碳酸鏻、四丁基胍、四丁基过氧单硫酸铵、四丁基过氧单硫酸鏻、四丁基过氧二硫酸铵、四丁基过氧二硫酸鏻、四丁基叠氮化铵、四丁基叠氮化鏻、单叔丁基苯基二苯基丙二酸锍、叔丁基苯基二苯基乙酸锍、苄基三乙基对-甲苯磺酸铵、二苯基二硫酸碘鎓、前述的水合物、和其混合物。
交联催化剂也可以是在小于或等于约500℃的温度下分解的硫酸产生剂，硫酸产生剂是当加热时将产生硫酸的化合物。在小于或等于约500℃的温度下分解的硫酸产生剂的实例可以包括硫酸、以下物质的硫酸氢盐或硫酸盐：三烷基胺、未取代或取代的二烷基单环烷基胺、未取代或取代的单烷基二环烷基胺、未取代或取代的三环烷基胺、三芳基胺、未取代或取代的二芳基单烷基胺、未取代或取代的单芳基二烷基胺、未取代或取代的三芳基胺、未取代或取代的氮杂环丙烷、未取代或取代的氮杂环丁烷、未取代或取代的吡咯、未取代或取代的吡啶、未取代或取代的哌啶，或者未取代或取代的哌嗪，例如三乙胺硫酸氢盐、三丁胺硫酸氢盐、哌嗪硫酸盐等。
交联催化剂它们的制备方法是本领域那些普通技术人员公知的，该制备方法可以基于用重要的碱中和酸。
本发明组合物可以包含溶剂。合适的溶剂包括例如酮，例如丙酮、甲乙酮、甲基异丁酮、环己酮、异佛尔酮、甲基异戊酮、2-庚酮4-羟基和4-甲基-2-戊酮；C1-C10脂族醇例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、苯酚等；含芳基的醇例如苄醇；环状碳酸酯例如碳酸乙烯酯和碳酸丙烯酯；脂族或芳族烃(例如己烷、甲苯、二甲苯等)；环醚例如二噁烷和四氢呋喃；乙二醇；丙二醇；己二醇；醚醇例如1-丁氧基乙氧基-2-丙醇、3-甲基-3-甲氧基丁醇、乙二醇正丁醚、乙二醇苯醚、乙二醇单甲醚、乙二醇单乙醚、乙二醇丙醚、二甘醇己醚、二甘醇单乙醚、二甘醇单甲醚、二甘醇单丁醚、二甘醇单丙醚、丙二醇乙醚、丙二醇异丁醚、丙二醇单甲醚、丙二醇单丁醚、丙二醇单乙醚、丙二醇正丙醚、丙二醇苯醚、丙二醇叔丁醚、二丙二醇乙醚、二丙二醇单丁醚、二丙二醇单甲醚、二丙二醇单丙醚、三甘醇乙醚、三甘醇甲醚、三甘醇正丁醚、三丙二醇甲醚、三丙二醇正丁醚；乙二醇烷基醚乙酸酯例如甲基溶纤剂乙酸酯和乙基溶纤剂乙酸酯；丙二醇烷基醚乙酸酯例如丙二醇甲醚乙酸酯、丙二醇乙醚乙酸酯、丙二醇丙醚乙酸酯和丙二醇丁醚乙酸酯；丙二醇烷基醚丙酸酯例如丙二醇甲醚丙酸酯、丙二醇乙醚丙酸酯、丙二醇丙醚丙酸酯和丙二醇丁醚丙酸酯；2-甲氧基乙醚(二甘醇二甲醚)；具有醚和羟基部分的溶剂例如甲氧基丁醇、乙氧基丁醇、甲氧基丙醇和乙氧基丙醇；酯例如乙酸甲酯、乙酸乙酯、乙酸丙酯和乙酸丁酯、戊酸甲酯、戊酸乙酯；2-羟基丙酸乙酯、2-羟基2-甲基丙酸甲酯、2-羟基2-甲基丙酸乙酯、羟基乙酸甲酯、羟基乙酸乙酯、羟基乙酸丁酯、乳酸甲酯、乳酸乙酯、乳酸丙酯、乳酸丁酯、3-羟基丙酸甲酯、3-羟基丙酸乙酯、3-羟基丙酸丙酯、3-羟基丙酸丁酯、2-羟基3-甲基丁酸甲酯、甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、乙氧基乙酸丙酯、乙氧基乙酸丁酯、丙氧基乙酸甲酯、丙氧基乙酸乙酯、丙氧基乙酸丙酯、丙氧基乙酸丁酯、丁氧基乙酸甲酯、丁氧基乙酸乙酯、丁氧基乙酸丙酯、丁氧基乙酸丁酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-甲氧基丙酸丁酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-乙氧基丙酸丙酯、2-乙氧基丙酸丁酯、2-丁氧基丙酸甲酯、2-丁氧基丙酸乙酯、2-丁氧基丙酸丙酯、2-丁氧基丙酸丁酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-甲氧基丙酸丙酯、3-甲氧基丙酸丁酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸丙酯、3-乙氧基丙酸丁酯、3-丙氧基丙酸甲酯、3-丙氧基丙酸乙酯、3-丙氧基丙酸丙酯、3-丙氧基丙酸丁酯、3-丁氧基丙酸甲酯、3-丁氧基丙酸乙酯、3-丁氧基丙酸丙酯和3-丁氧基丙酸丁酯；氧异丁酸酯例如2-羟基异丁酸甲酯、α-甲氧基异丁酸甲酯、甲氧基异丁酸乙酯、α-乙氧基异丁酸甲酯、α-乙氧基异丁酸乙酯、β-甲氧基异丁酸甲酯、β-甲氧基异丁酸乙酯、β-乙氧基异丁酸甲酯、β-乙氧基异丁酸乙酯、β-异丙氧基异丁酸甲酯、β-异丙氧基异丁酸乙酯、β-异丙氧基异丁酸异丙酯、β-异丙氧基异丁酸丁酯、β-丁氧基异丁酸甲酯、β-丁氧基异丁酸乙酯、β-丁氧基异丁酸丁酯、α-羟基异丁酸甲酯、α-羟基异丁酸乙酯、α-羟基异丁酸异丙酯和α-羟基异丁酸丁酯；和其他溶剂例如二元酯，和γ-丁内酯；酮醚衍生物例如二丙酮醇甲醚；酮醇衍生物例如丙酮醇或二丙酮醇；内酯例如丁内酯；酰胺衍生物例如二甲基乙酰胺或二甲基甲酰胺、茴香醚，和其混合物。
可加入本发明组合物中的任选组分是致孔剂，其可用于降低由本发明组合物形成的膜的介电常数。如本文中使用的，“致孔剂”是指任何产生孔的化合物，例如能够分解成小分子并且随后挥发由此形成纳米孔的热和/或辐射不稳定的有机聚合物。形成这类多孔低k介电层的条件是本领域那些技术人员公知的。
其他任选组分包括光酸产生剂和热酸产生剂，其类似物是本领域公知的。光酸产生剂的实例包括锍盐、碘鎓盐、磺酰基二偶氮甲烷类、N-磺酰基氧酰亚胺类和N-磺酰基氧肟类。热酸产生剂的实例包括2，4，4，6-四溴环己二烯酮、安息香甲苯磺酸酯(benzoin tosylate)、甲苯磺酸2-硝基苄基酯、其他有机磺酸烷基酯。
可以使用本领域那些技术人员公知的技术例如浸涂、旋涂或喷涂将本发明的组合物涂覆在基底上。抗反射涂层的膜厚度为约0.01μm-约1μm。可以将所述涂层在热板或对流加热炉或者其他公知的加热方法上加热以除去任何残余的溶剂和诱导交联(如果希望的话)，和使抗反射涂层不溶解以防止抗反射涂层与光致抗蚀剂之间的互混。
有两种光致抗蚀剂组合物：负性作用的和正性作用的。当负性光致抗蚀剂组合物对辐射成像式曝光时，抗蚀剂组合物的对辐射曝光的区域变得较不可溶于显影液(例如出现交联反应)，而光致抗蚀剂涂层的未曝光区域保持相对可溶于该溶液。因此，用显影剂处理被曝光的负性抗蚀剂导致除去光致抗蚀剂涂层的未曝光区域并且在涂层中产生负图像，由此使其上沉积有光致抗蚀剂组合物的下方基底表面的所希望部分露出。
另一方面，当正性光致抗蚀剂组合物对辐射成像式曝光时，光致抗蚀剂组合物的那些对辐射曝光的区域变得更溶于显影液(例如出现重排反应)，而那些未曝光的区域保持相对不溶于显影液。因此，用显影剂处理曝光的正性光致抗蚀剂导致除去曝光的涂料区域并且在光致抗蚀剂涂层中产生正像。同样，下方表面的所希望部分被露出。
负性光致抗蚀剂组合物和正性光致抗蚀剂组合物以及它们的应用是本领域那些技术人员公知的。
本发明的方法包括：用本发明的组合物涂覆基底和将基底在热板或对流加热炉或者其他公知的加热方法上在足够的温度下加热足够长的时间以除去涂层溶剂，和使聚合物交联至足够的程度以使得所述涂层不溶于光致抗蚀剂的涂覆溶液或者含水碱性显影剂中。可以使用本领域公知的方法施加边胶清洗剂以清洁基底的边缘。加热温度范围为约70℃-约500℃。如果温度低于70℃，则可能出现溶剂的不充足损耗或者不足量的交联。然后将光致抗蚀剂组合物的膜涂覆在抗反射涂层上并烘焙以基本上除去光致抗蚀剂溶剂。将光致抗蚀剂成像式曝光并且在含水显影剂中显影以除去经处理的抗蚀剂。在显影之前和在曝光之后，可以将任选的加热步骤引入所述方法中。将光致抗蚀剂涂覆和成像的方法是本领域那些技术人员公知的并且针对所使用的抗蚀剂的具体类型而被最优化。然后可以在合适的蚀刻室中将经构图的基底干法蚀刻以除去抗反射膜的被曝光部分，而其余光致抗蚀剂充当蚀刻掩模。
基底可以是Si、SiO2、SiON、SiN、p-Si、α-Si、SiGe、W、W-Si、Al、Cu、Al-Si、低k电介质等，或者在一些情形中是碳层(有时称为硬掩模)，例如抗反射涂层。当使用碳层时，形成三层体系，其中由本发明的组合物形成的硅涂层是中间层。即首先将碳层涂覆在基底例如硅晶片上。在合适的加工后，涂覆本发明的硅涂料组合物并且加工。然后涂覆光致抗蚀剂层并且将整个层叠体进一步加工。三层体系是本领域那些技术人员公知的。
以下实施例提供了制备和使用本发明的方法的说明。然而，这些实施例不意在以任何方式限制本发明的范围并且不应该被理解为提供必须专门使用以实践本发明的条件、参数或数值。除非另外说明，所有份和百分比以重量计。
合成例1
将180克甲基三甲氧基硅烷、120克2-氰基乙基三乙氧基硅烷、36克苯基三甲氧基硅烷和270克冰醋酸装入配有温度计、冷水冷凝器和机械搅拌器的2L烧瓶中。在将反应混合物加热至80℃后，加入溶于31克乙酸中的4克对-甲苯磺酸一水合物。将反应保持在回流下17小时并且然后使其冷却至室温。在将反应溶液冷却至室温后，将溶液过滤并且伴随着搅拌将滤液缓慢倒入DI水中，导致聚合物沉淀。将沉淀的聚合物过滤，用DI水彻底清洗并且在室温下干燥。FTIR表明聚合物含有SiOH基团。该聚合物被发现可溶于大多数有机溶剂中。然而，一旦在升高的温度下干燥，则由于SiOH基团的进一步缩合，该聚合物变得不可溶。该聚合物具有4566g/mol的Mw和2030g/mol的Mn。
合成例2
在配有温度计、冷水冷凝器和机械搅拌器的500mL烧瓶中将30.2克得自合成例1的聚合物溶于100克丙酮中。加入16.5克双氯甲基四甲基二硅氧烷和2.67克3-氰基丙基二甲基氯硅烷并且使反应混合物回流16小时。然后使溶液冷却至室温。然后伴随着搅拌将冷却的溶液倒入己烷中，导致聚合物沉淀。将得到的聚合物溶于丙酮中、过滤并且在DI水中沉淀。将得到的聚合物过滤并且用DI水彻底清洗。最后将聚合物(20g)在真空炉中在45℃下干燥2天。FTIR没有检测到聚合物中的SiOH基团。1H NMR表明聚合物不含SiOCH2CH3或SiOCH3基团。该聚合物被发现可溶于大多数有机溶剂中。该聚合物具有8303g/mol的Mw和3301g/mol的Mn。
合成例3
将70克甲基三甲氧基硅烷、30克3-氯丙基三甲氧基硅烷、14.2克苯基三甲氧基硅烷和108克冰醋酸装入配有温度计、冷水冷凝器和机械搅拌器的2L烧瓶中。在将反应混合物加热至80℃后，加入1.4克对-甲苯磺酸一水合物。将反应保持在回流下16小时并且然后使其冷却至室温。在将反应溶液冷却至室温后，将溶液过滤并且伴随着搅拌将滤液缓慢倒入DI水中，导致聚合物沉淀。将沉淀的聚合物过滤、用DI水彻底清洗并且在室温下干燥。FTIR表明聚合物含有SiOH基团。该聚合物被发现可溶于大多数有机溶剂中。然而，一旦在升高的温度下干燥，则由于SiOH基团的进一步缩合，因此聚合物变得不可溶。
合成例4
在配有温度计、冷水冷凝器和机械搅拌器的500mL烧瓶中将30克得自合成例3的聚合物、8克1，3-双(3-羧基丙基)四甲基二硅氧烷和0.5克对-甲苯磺酸一水合物溶于120克丙酮中。使反应混合物回流18小时。然后使溶液冷却至室温。在冷却后，将溶液过滤并且伴随着搅拌倒入DI水中，使聚合物沉淀。将聚合物过滤并且用DI水彻底清洗。最后将聚合物(18g)在真空炉中在45℃下干燥2天。1H NMR表明聚合物不含SiOCH3基团。该聚合物被发现可溶于大多数有机溶剂中。该聚合物具有6430g/mol的Mw和2490g/mol的Mn。
合成例5
将4.5克氢氧化钠溶于100克DI水中。在搅拌下，向其中缓慢加入溶于50g DI水中的18.5克硝酸银。通过过滤分离出沉淀的Ag2O并且用DI水和甲醇彻底清洗。将16.08克叔丁基苯基二苯基溴化锍溶于约400克甲醇中。在搅拌下加入新鲜制备的Ag2O。在室温下继续搅拌4小时。将固体滤出。将3.2克冰醋酸加入滤液中。通过使用旋转蒸发器除去溶剂而将滤液浓缩并且倒入二乙醚中，得到透明的粘性液体。在将该液体用醚清洗另外2次后，在旋转蒸发器上除去其中的挥发物。得到13.4克确定为叔丁基苯基二苯基乙酸锍的粘性液体。
评价例1
通过将0.5g合成例2中制备的聚合物和0.005g四乙基乙酸铵四水合物溶于9.5克丙二醇单甲醚乙酸酯/丙二醇单甲醚(70∶30)(PGMEA/PGME)的混合物中而制备涂料组合物。然后通过0.2μm过滤器将该溶液过滤。将薄膜旋涂在4英寸晶片上并且在200℃下烘焙90s。当将晶片浸入PGMEA/PGME中1min时，没有观察到膜厚度损失，表明充足的固化。
评价例2
通过将0.5g合成例2中制备的聚合物和0.01g得自合成例4的叔丁基苯基二苯基乙酸锍溶于9.5克丙二醇单甲醚乙酸酯/丙二醇单甲醚(70∶30)(PGMEA/PGME)的混合物中而制备涂料组合物。然后通过0.2μm过滤器将该溶液过滤。将薄膜旋涂在4英寸晶片上并且在200℃下烘焙60s。当将晶片浸入PGMEA/PGME中1min时，没有观察到膜厚度损失，表明充足的固化。
评价例3
通过将1.29g合成例2中制备的聚合物、0.038g 98wt％硫酸和0.019克二环己胺溶于24克丙二醇单甲醚乙酸酯/丙二醇单甲醚(70∶30)(PGMEA/PGME)的混合物中而制备涂料组合物。然后通过0.2μm过滤器将该溶液过滤。将薄膜旋涂在4英寸晶片上并且在240℃下烘焙60s。当将晶片浸入PGMEA/PGME中1min时，没有观察到膜厚度损失，表明充足的固化。
评价例4
硅氧烷配方的制备：
将5g聚(苯基-甲基硅倍半氧烷)(可从Gelest获得的SST-3PM1)用95g PGME稀释。在不加入任何盐的情况下，该配方充当参考(配方在表1中被缩写为REF)。通过取5mL等分试样的REF并且将1mL于PGME中的1％盐溶液加入每一等分试样中制备多个配方；使用的盐和它们的缩写示于表1中。盐浓度对应于4wt％有机硅聚合物。
涂覆：
然后将表1中列出的配方的等分试样旋涂在4英寸晶片上并且在表2中所示温度下烘焙60秒。将晶片部分浸入PGME中60秒并且用压缩空气吹干。在未浸渍(FTUI)和浸渍(FTI)区域中测量膜厚度(FT)。数据汇编在表2中。
表1
表2
试验结果：
如表2中所示，在不加入盐的情况下，当浸渍时有机硅膜被完全从晶片上除去。盐的加入可以产生使得大部分膜在浸渍后保留下来的热固性物质。在膜固化中，如由％FT损失所示，一些盐比另一些更好；然而，表现出良好的热固性能的一些盐例如TBAA和TBAazide也被发现具有差的储存寿命。
本发明的前述描述解释和描述了本发明。另外，本披露内容仅仅示出和描述了本发明的某些实施方案，但如上所述，将理解的是本发明能够用于各种其他的组合、改进和环境中，并且能够在如本文中所示的、与上述教导相当的本发明概念、和/或相关领域的技能或知识的范围内改变或改进。上文中描述的实施方案进一步意在解释已知的实践本发明的最好方式，并且使得本领域其他技术人员能够在这些或其他实施方案中并且采用本发明的特定应用或使用所需的各种改进方式来使用本发明。因此，本描述不意在将本发明限于本文中披露的形式。并且意在将附属的权利要求书理解为包括备选实施方案。
Claims (14)
1.一种组合物，其包含：
(a)具有至少一种下式的重复单元的聚合物：
其中R1是不可水解基团并且n是1-3的整数，
其中该聚合物能够用交联催化剂交联并且其中该聚合物不含SiOH和SiOR基团，其中R为烷基；和
(b)交联催化剂，该催化剂选自具有式Z+A-的化合物及其水合物，其中Z是选自三芳基取代的锍、三烷基取代的锍和被芳基和烷基的混合基团取代的锍的阳离子，和A是含有选自单羧酸盐离子和二羧酸盐离子的基团的阴离子。
2.权利要求1的组合物，其中不可水解基团选自氢、未取代或取代的烷基、未取代或取代的单环或多环芳基、未取代或取代的单环或多环芳烷基、羧基和甲醇。
3.权利要求1的组合物，其中A选自乙酸根、甲酸根、丙酸根、琥珀酸根、丙二酸根、单丙二酸根和己二酸根。
4.权利要求1的组合物，其中不可水解基团选自氢、未取代或取代的单环烷基或多环烷基、未取代或取代的单环或多环芳基、未取代或取代的单环或多环芳烷基、羧基和甲醇。
5.权利要求1的组合物，其中交联剂选自式Z+A-的化合物及其水合物，其中Z是选自三苯基锍和(4-叔丁基苯基)二苯基锍的阳离子，和A是含有选自单羧酸根离子和二羧酸根离子的基团的阴离子。
6.权利要求1的组合物，其进一步包含以下的一种或多种：光酸产生剂、热酸产生剂、表面活性剂和致孔剂。
7.一种在基底上形成图像的方法，其包括a)用权利要求1-6中任一项的组合物涂覆基底；b)将步骤a)的涂层加热；c)在步骤b)的涂层上由光致抗蚀剂溶液形成涂层；d)将光致抗蚀剂涂层加热以从该涂层中基本上除去溶剂；e)将光致抗蚀剂涂层成像式曝光；f)使用含水碱性显影剂将图像显影；g)任选地，在显影之前和之后加热基底；和h)将步骤b)的组合物干法蚀刻。
8.权利要求7的方法，其中基底是碳层/硬掩模。
9.权利要求7的方法，其中基底选自Si、SiO2、SiON、SiN、p-Si、α-Si、W、W-Si、Al、Cu和Al-Si。
10.一种涂覆的基底，其包括在其上具有以下的基底；权利要求1-6中任一项的组合物的层；和该组合物之上的正性光致抗蚀剂组合物的层。
11.权利要求10的涂覆的基底，其中基底是碳层/硬掩模。
12.权利要求10的涂覆的基底，其中基底选自Si、SiO2、SiON、SiN、p-Si、α-Si、W、W-Si、Al、Cu和Al-Si。
13.一种制备如权利要求1中定义的聚合物的方法，其包括使一种或多种具有式R1 mSi(X)4-m的单体反应以形成具有Si-OH和Si-OR1基团两者的聚合物，其中每一R1独立地是未取代或取代的烷基或者未取代或取代的芳基，X是卤素或OR1，和m是0-3的整数；将所述具有Si-OH和Si-OR1基团两者的聚合物水解以形成仅具有Si-OH基团的聚合物；和使所述仅具有Si-OH基团的聚合物与封端剂反应直到该聚合物中不存在Si-OH基团。
14.权利要求13的方法，其中封端剂选自具有式Ra 3Si(Rb)的化合物，其中每一Ra独立地是未取代或取代的烷基或者未取代或取代的芳基，并且Rb是ORa或卤素，和具有式(R10)3Si-Y-Si(R10)3的化合物，其中每一R10选自未取代或取代的C1-4烷基和未取代或取代的C1-4烷氧基，和Y是选自-O-和-NR11-的连接基团，其中R11是氢或者C1-10未取代和取代的支化或直链烷基。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/676,673 | 2007-02-20 | ||
| US11/676,673 US8026040B2 (en) | 2007-02-20 | 2007-02-20 | Silicone coating composition |
| PCT/IB2008/000432 WO2008102256A1 (en) | 2007-02-20 | 2008-02-15 | Silicone coating composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101617010A CN101617010A (zh) | 2009-12-30 |
| CN101617010B true CN101617010B (zh) | 2012-09-05 |
Family
ID=39511096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008800056175A Active CN101617010B (zh) | 2007-02-20 | 2008-02-15 | 有机硅涂料组合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8026040B2 (zh) |
| EP (2) | EP2450412B1 (zh) |
| JP (1) | JP5458306B2 (zh) |
| KR (1) | KR101429317B1 (zh) |
| CN (1) | CN101617010B (zh) |
| TW (1) | TWI409310B (zh) |
| WO (1) | WO2008102256A1 (zh) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7550249B2 (en) * | 2006-03-10 | 2009-06-23 | Az Electronic Materials Usa Corp. | Base soluble polymers for photoresist compositions |
| US7704670B2 (en) * | 2006-06-22 | 2010-04-27 | Az Electronic Materials Usa Corp. | High silicon-content thin film thermosets |
| KR100796047B1 (ko) * | 2006-11-21 | 2008-01-21 | 제일모직주식회사 | 레지스트 하층막용 하드마스크 조성물, 이를 이용한 반도체집적회로 디바이스의 제조방법 및 그로부터 제조된 반도체집적회로 디바이스 |
| US7759046B2 (en) | 2006-12-20 | 2010-07-20 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
| US7736837B2 (en) * | 2007-02-20 | 2010-06-15 | Az Electronic Materials Usa Corp. | Antireflective coating composition based on silicon polymer |
| WO2008104881A1 (en) * | 2007-02-27 | 2008-09-04 | Az Electronic Materials Usa Corp. | Silicon-based antifrelective coating compositions |
| EP2179842B1 (en) * | 2007-08-14 | 2016-11-09 | Toyo Seikan Kaisha, Ltd. | Biodegradable resin container having deposited film, and method for formation of deposited film |
| US20090253081A1 (en) * | 2008-04-02 | 2009-10-08 | David Abdallah | Process for Shrinking Dimensions Between Photoresist Pattern Comprising a Pattern Hardening Step |
| US20090253080A1 (en) * | 2008-04-02 | 2009-10-08 | Dammel Ralph R | Photoresist Image-Forming Process Using Double Patterning |
| US8084186B2 (en) * | 2009-02-10 | 2011-12-27 | Az Electronic Materials Usa Corp. | Hardmask process for forming a reverse tone image using polysilazane |
| US20100291475A1 (en) * | 2009-05-12 | 2010-11-18 | Chenghong Li | Silicone Coating Compositions |
| JP5663959B2 (ja) * | 2010-05-28 | 2015-02-04 | Jsr株式会社 | 絶縁パターン形成方法及びダマシンプロセス用絶縁パターン形成材料 |
| KR20120060154A (ko) * | 2010-12-01 | 2012-06-11 | 제록스 코포레이션 | 박막 트랜지스터용 유전체 조성물 |
| US8647809B2 (en) | 2011-07-07 | 2014-02-11 | Brewer Science Inc. | Metal-oxide films from small molecules for lithographic applications |
| US9011591B2 (en) * | 2011-09-21 | 2015-04-21 | Dow Global Technologies Llc | Compositions and antireflective coatings for photolithography |
| US9068086B2 (en) * | 2011-12-21 | 2015-06-30 | Dow Global Technologies Llc | Compositions for antireflective coatings |
| JP6510161B2 (ja) * | 2011-12-21 | 2019-05-08 | ダウ グローバル テクノロジーズ エルエルシー | 反射防止被膜用の組成物 |
| MY171727A (en) * | 2012-10-30 | 2019-10-25 | Lintec Corp | Curable polysilsesquioxane compound, method for producing same, curable composition, cured product, and method for using curable composition or the like |
| EP2920216B1 (en) * | 2012-11-13 | 2016-09-21 | 3M Innovative Properties Company | Curable antifouling composition, method of use, and articles |
| US9703010B2 (en) | 2013-02-08 | 2017-07-11 | Corning Incorporated | Articles with anti-reflective high-hardness coatings and related methods |
| KR101599953B1 (ko) | 2013-08-08 | 2016-03-04 | 제일모직 주식회사 | 실리카계 절연층 형성용 조성물, 실리카계 절연층 및 실리카계 절연층의 제조방법 |
| WO2016167892A1 (en) * | 2015-04-13 | 2016-10-20 | Honeywell International Inc. | Polysiloxane formulations and coatings for optoelectronic applications |
| JP6997373B2 (ja) | 2016-02-15 | 2022-01-17 | Jsr株式会社 | レジスト下層膜形成用組成物、レジスト下層膜及びパターニングされた基板の製造方法 |
| US10381481B1 (en) | 2018-04-27 | 2019-08-13 | Taiwan Semiconductor Manufacturing Co., Ltd. | Multi-layer photoresist |
| US10573520B2 (en) * | 2018-06-12 | 2020-02-25 | International Business Machines Corporation | Multiple patterning scheme integration with planarized cut patterning |
| US20220187709A1 (en) * | 2019-03-28 | 2022-06-16 | Nissan Chemical Corporation | Film-forming composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040137241A1 (en) * | 2003-01-08 | 2004-07-15 | International Business Machines Corporation | Patternable low dielectric constsnt materials and their use in ULSI interconnection |
| WO2007011057A1 (ja) * | 2005-07-19 | 2007-01-25 | Dow Corning Toray Co., Ltd. | ポリシロキサンおよびその製造方法 |
Family Cites Families (183)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899412A (en) | 1959-08-11 | Polysulfone resins from bicycloheptene | ||
| US2310605A (en) | 1939-02-03 | 1943-02-09 | Freeport Sulphur Co | Production of sulphur dioxideolefin resins |
| US2625525A (en) | 1949-11-17 | 1953-01-13 | Phillips Petroleum Co | Terpolymers of sulfur dioxide, monoolefinic materials and a liquid polymer of a conjugated diene, and their production |
| US2703793A (en) | 1951-07-10 | 1955-03-08 | Du Pont | Process for preparing interpolymers of so2 with propylene and an acrylate |
| US2779749A (en) | 1952-09-29 | 1957-01-29 | Phillips Petroleum Co | Stabilized unsaturate-so2 resins containing acrylates |
| GB744264A (en) | 1952-09-29 | 1956-02-01 | Phillips Petroleum Co | Improvements in or relating to resins |
| GB757046A (en) | 1953-04-20 | 1956-09-12 | Phillips Petroleum Co | Improvements in or relating to resin/rubber compositions |
| US2794014A (en) | 1953-10-15 | 1957-05-28 | Dow Chemical Co | Water-soluble heteropolymers of acrylic acid, allyl alcohol, and sulfur dioxide and processes for producing the same |
| US2778812A (en) | 1953-11-23 | 1957-01-22 | Dow Chemical Co | Water soluble copolymers of so2, an acrylic acid and a vinyl alkyl ether |
| US2943077A (en) | 1956-11-01 | 1960-06-28 | Du Pont | Copolymers of ethylene and sulfur dioxide |
| US3313785A (en) | 1963-06-11 | 1967-04-11 | Union Carbide Corp | Polysulfones and method for their production |
| US3318844A (en) | 1963-12-23 | 1967-05-09 | Gen Electric | Organopolysiloxanes |
| US3474054A (en) | 1966-09-13 | 1969-10-21 | Permalac Corp The | Surface coating compositions containing pyridine salts or aromatic sulfonic acids |
| GB1118950A (en) | 1966-12-29 | 1968-07-03 | Andersen & Brunn England Ltd | Improvements relating to bottle capsules |
| US3663507A (en) | 1970-01-02 | 1972-05-16 | Minnesota Mining & Mfg | Linear polyarylsulfones having functional groups thereon |
| US3792026A (en) | 1970-09-08 | 1974-02-12 | Dow Chemical Co | High molecular weight olefin polysulfone resins and process for their preparation |
| US3890287A (en) | 1973-09-21 | 1975-06-17 | Dow Chemical Co | Polysulfone copolymers |
| US3893127A (en) | 1973-09-27 | 1975-07-01 | Rca Corp | Electron beam recording media |
| US3884696A (en) | 1974-03-05 | 1975-05-20 | Bell Telephone Labor Inc | Positive photoresist comprising polysulfones formed by reacting vinyl aromatic hydrocarbons with sulfur dioxide |
| US3898350A (en) | 1974-06-27 | 1975-08-05 | Ibm | Terpolymers for electron beam positive resists |
| US3935332A (en) | 1975-01-09 | 1976-01-27 | Rca Corporation | Development of poly(1-methyl-1-cyclopentene-SO2) electron beam resist |
| US3935331A (en) | 1975-01-09 | 1976-01-27 | Rca Corporation | Preparation of olefin SO2 copolymer electron beam resist films and use of same for recording |
| US4153741A (en) | 1976-07-30 | 1979-05-08 | Rca Corporation | Method for forming a surface relief pattern in a poly(olefin sulfone) layer |
| US4045318A (en) | 1976-07-30 | 1977-08-30 | Rca Corporation | Method of transferring a surface relief pattern from a poly(olefin sulfone) layer to a metal layer |
| US4267257A (en) | 1976-07-30 | 1981-05-12 | Rca Corporation | Method for forming a shallow surface relief pattern in a poly(olefin sulfone) layer |
| US4126712A (en) | 1976-07-30 | 1978-11-21 | Rca Corporation | Method of transferring a surface relief pattern from a wet poly(olefin sulfone) layer to a metal layer |
| US4097618A (en) | 1977-03-09 | 1978-06-27 | Rca Corporation | Method of transferring a surface relief pattern from a poly(1-methyl-1-cyclopropene sulfone) layer to a non-metallic inorganic layer |
| US4289845A (en) | 1978-05-22 | 1981-09-15 | Bell Telephone Laboratories, Inc. | Fabrication based on radiation sensitive resists and related products |
| US4251665A (en) | 1978-05-22 | 1981-02-17 | King Industries, Inc. | Aromatic sulfonic acid oxa-azacyclopentane adducts |
| US4200729A (en) | 1978-05-22 | 1980-04-29 | King Industries, Inc | Curing amino resins with aromatic sulfonic acid oxa-azacyclopentane adducts |
| US4393160A (en) | 1980-12-23 | 1983-07-12 | Rca Corporation | Aqueous developable poly(olefin sulfone) terpolymers |
| US4341861A (en) | 1980-12-23 | 1982-07-27 | Rca Corporation | Aqueous developable poly(olefin sulfone) terpolymers |
| US4405776A (en) | 1981-03-16 | 1983-09-20 | Rca Corporation | Positive radiation sensitive resist terpolymer from omega alkynoic acid |
| US4355094A (en) | 1981-03-16 | 1982-10-19 | Rca Corporation | Positive radiation sensitive resist terpolymers |
| JPS5852638A (ja) | 1981-09-24 | 1983-03-28 | Hitachi Ltd | 放射線感応性組成物 |
| US4396702A (en) | 1981-11-10 | 1983-08-02 | Rca Corporation | Method of forming pattern in positive resist media |
| US4397939A (en) | 1981-12-14 | 1983-08-09 | Rca Corporation | Method of using a positive electron beam resist medium |
| US4397938A (en) | 1981-12-14 | 1983-08-09 | Rca Corporation | Method of forming resist patterns using X-rays or electron beam |
| US4504372A (en) | 1982-03-12 | 1985-03-12 | Ciba-Geigy Corporation | Acid-curable composition containing a masked curing catalyst, and a process for its preparation |
| US4398001A (en) | 1982-03-22 | 1983-08-09 | International Business Machines Corporation | Terpolymer resist compositions |
| US4491628A (en) | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
| EP0157262B1 (en) | 1984-03-19 | 1988-06-08 | Nippon Oil Co. Ltd. | Novel electron beam resist materials |
| DE3678652D1 (de) * | 1985-03-07 | 1991-05-16 | Hughes Aircraft Co | Polysiloxanschutzlack fuer ionen- und elektronenstrahl-lithographie. |
| CA1269794A (en) | 1985-10-15 | 1990-05-29 | Eit Drent | Copolymers of so.sub.2 and ethene |
| JP2608429B2 (ja) * | 1987-11-09 | 1997-05-07 | 東レ・ダウコーニング・シリコーン株式会社 | パターン形成用材料およびパターン形成方法 |
| US5200544A (en) | 1988-02-25 | 1993-04-06 | At&T Bell Laboratories | Resist materials |
| US4996136A (en) | 1988-02-25 | 1991-02-26 | At&T Bell Laboratories | Radiation sensitive materials and devices made therewith |
| US4973526A (en) * | 1990-02-15 | 1990-11-27 | Dow Corning Corporation | Method of forming ceramic coatings and resulting articles |
| US5072024A (en) * | 1990-04-27 | 1991-12-10 | The Standard Oil Company | Synthesis of N-substituted amides by condensation of nitriles with certain organic hydroxyl compounds |
| US5457003A (en) | 1990-07-06 | 1995-10-10 | Nippon Telegraph And Telephone Corporation | Negative working resist material, method for the production of the same and process of forming resist patterns using the same |
| US5100503A (en) | 1990-09-14 | 1992-03-31 | Ncr Corporation | Silica-based anti-reflective planarizing layer |
| US5298367A (en) | 1991-03-09 | 1994-03-29 | Basf Aktiengesellschaft | Production of micromoldings having a high aspect ratio |
| KR950000074B1 (ko) | 1991-03-28 | 1995-01-09 | 금호석유화학 주식회사 | 이산화황과 핵치환 트리알킬게르밀스티렌(Trialkeylgermylstyrene)의 다원공중합체 |
| US5187019A (en) | 1991-09-06 | 1993-02-16 | King Industries, Inc. | Latent catalysts |
| US6773864B1 (en) | 1991-11-15 | 2004-08-10 | Shipley Company, L.L.C. | Antihalation compositions |
| TW211080B (zh) | 1991-12-12 | 1993-08-11 | American Telephone & Telegraph | |
| US5242343A (en) * | 1992-09-30 | 1993-09-07 | Larry Miller | Stationary exercise device |
| US5384376A (en) | 1992-12-23 | 1995-01-24 | Eastman Kodak Company | Organic/inorganic hybrid materials |
| US5529554A (en) * | 1993-04-22 | 1996-06-25 | Eschenbach; Paul W. | Collapsible exercise machine with multi-mode operation |
| GB9402916D0 (en) * | 1994-02-16 | 1994-04-06 | Pfizer Ltd | Antiparasitic agents |
| DE4436151A1 (de) | 1994-08-16 | 1996-05-02 | Henkel Kgaa | Verfahren zur Herstellung eines Flüssigwaschmittels mit Bleiche |
| US5562653A (en) | 1994-11-16 | 1996-10-08 | Hercules Incorporated | Medical devices composed of low ceiling temperature polymers |
| US5918147A (en) | 1995-03-29 | 1999-06-29 | Motorola, Inc. | Process for forming a semiconductor device with an antireflective layer |
| US5616103A (en) * | 1995-08-03 | 1997-04-01 | Lee; Kuo-Ron | Jogger exerciser |
| US5693691A (en) | 1995-08-21 | 1997-12-02 | Brewer Science, Inc. | Thermosetting anti-reflective coatings compositions |
| US6770726B1 (en) | 1995-09-12 | 2004-08-03 | Gelest, Inc. | β-substituted organosilsesquioxane polymers |
| WO1997010282A1 (en) | 1995-09-12 | 1997-03-20 | Gelest, Inc. | Beta-substituted organosilsesquioxanes and use thereof |
| JP4221522B2 (ja) | 1996-02-29 | 2009-02-12 | スリーエム カンパニー | 共一連続相を有する光学薄膜 |
| US5843624A (en) | 1996-03-08 | 1998-12-01 | Lucent Technologies Inc. | Energy-sensitive resist material and a process for device fabrication using an energy-sensitive resist material |
| EP0921167A4 (en) | 1996-08-22 | 2000-01-12 | Kaneka Corp | CURABLE COMPOSITION FOR EXTERIOR COATING AND ARTICLES THEREOF COVERED |
| US6808859B1 (en) | 1996-12-31 | 2004-10-26 | Hyundai Electronics Industries Co., Ltd. | ArF photoresist copolymers |
| US5871872A (en) * | 1997-05-30 | 1999-02-16 | Shipley Company, Ll.C. | Dye incorporated pigments and products made from same |
| US6428894B1 (en) | 1997-06-04 | 2002-08-06 | International Business Machines Corporation | Tunable and removable plasma deposited antireflective coatings |
| US5926740A (en) | 1997-10-27 | 1999-07-20 | Micron Technology, Inc. | Graded anti-reflective coating for IC lithography |
| US5860895A (en) * | 1997-11-06 | 1999-01-19 | Lee; Kuo-Lung | Structure of folding collapsible step exercising machine |
| US6218292B1 (en) | 1997-12-18 | 2001-04-17 | Advanced Micro Devices, Inc. | Dual layer bottom anti-reflective coating |
| US6030320A (en) * | 1998-01-12 | 2000-02-29 | Stearns; Kenneth W. | Collapsible exercise apparatus |
| JPH11286549A (ja) | 1998-02-05 | 1999-10-19 | Canon Inc | 感光性樹脂及び該感光性樹脂を用いたレジスト、該レジストを用いた露光装置及び露光方法及び該露光方法で得られた半導体装置 |
| US6069259A (en) | 1998-02-06 | 2000-05-30 | Rensselaer Polytechnic Institute | Multifunctional polymerizible alkoxy siloxane oligomers |
| FR2776540B1 (fr) | 1998-03-27 | 2000-06-02 | Sidel Sa | Recipient en matiere a effet barriere et procede et appareil pour sa fabrication |
| US6316167B1 (en) | 2000-01-10 | 2001-11-13 | International Business Machines Corporation | Tunabale vapor deposited materials as antireflective coatings, hardmasks and as combined antireflective coating/hardmasks and methods of fabrication thereof and application thereof |
| US6087064A (en) | 1998-09-03 | 2000-07-11 | International Business Machines Corporation | Silsesquioxane polymers, method of synthesis, photoresist composition, and multilayer lithographic method |
| US6849377B2 (en) | 1998-09-23 | 2005-02-01 | E. I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| US6139920A (en) | 1998-12-21 | 2000-10-31 | Xerox Corporation | Photoresist compositions |
| JP4096138B2 (ja) | 1999-04-12 | 2008-06-04 | Ｊｓｒ株式会社 | レジスト下層膜用組成物の製造方法 |
| US6030319A (en) * | 1999-04-15 | 2000-02-29 | Modas Shing Company Ltd. | Foldable cross-country skiing exerciser |
| US6790587B1 (en) | 1999-05-04 | 2004-09-14 | E. I. Du Pont De Nemours And Company | Fluorinated polymers, photoresists and processes for microlithography |
| US6824879B2 (en) | 1999-06-10 | 2004-11-30 | Honeywell International Inc. | Spin-on-glass anti-reflective coatings for photolithography |
| CA2374944A1 (en) | 1999-06-10 | 2000-12-21 | Nigel Hacker | Spin-on-glass anti-reflective coatings for photolithography |
| US6890448B2 (en) | 1999-06-11 | 2005-05-10 | Shipley Company, L.L.C. | Antireflective hard mask compositions |
| JP2001106785A (ja) | 1999-08-05 | 2001-04-17 | Canon Inc | 感光性樹脂及び該感光性樹脂を用いたレジスト組成物、該レジスト組成物を用いたパターン形成方法、該パターン形成方法により製造されるデバイス及び該感光性樹脂を有するレジストを用いた露光方法 |
| KR100427440B1 (ko) | 1999-12-23 | 2004-04-17 | 주식회사 하이닉스반도체 | 유기 반사방지 화합물 및 그의 제조방법 |
| JP3795333B2 (ja) | 2000-03-30 | 2006-07-12 | 東京応化工業株式会社 | 反射防止膜形成用組成物 |
| US6379014B1 (en) | 2000-04-27 | 2002-04-30 | N & K Technology, Inc. | Graded anti-reflective coatings for photolithography |
| US20040176488A1 (en) | 2000-06-06 | 2004-09-09 | Shyama Mukherjee | Low dielectric materials and methods of producing same |
| KR100592381B1 (ko) | 2000-06-12 | 2006-06-22 | 엘지.필립스 엘시디 주식회사 | 액정 표시소자 및 그의 제조방법 |
| AU2001274579A1 (en) | 2000-06-21 | 2002-01-02 | Asahi Glass Company, Limited | Resist composition |
| US6420088B1 (en) | 2000-06-23 | 2002-07-16 | International Business Machines Corporation | Antireflective silicon-containing compositions as hardmask layer |
| US6818250B2 (en) | 2000-06-29 | 2004-11-16 | The Regents Of The University Of Colorado | Method for forming SIO2 by chemical vapor deposition at room temperature |
| US20030176614A1 (en) | 2000-06-30 | 2003-09-18 | Nigel Hacker | Organohydridosiloxane resins with high organic content |
| US6368400B1 (en) | 2000-07-17 | 2002-04-09 | Honeywell International | Absorbing compounds for spin-on-glass anti-reflective coatings for photolithography |
| US6447980B1 (en) | 2000-07-19 | 2002-09-10 | Clariant Finance (Bvi) Limited | Photoresist composition for deep UV and process thereof |
| TW556047B (en) | 2000-07-31 | 2003-10-01 | Shipley Co Llc | Coated substrate, method for forming photoresist relief image, and antireflective composition |
| TW588072B (en) | 2000-10-10 | 2004-05-21 | Shipley Co Llc | Antireflective porogens |
| TW538319B (en) | 2000-10-10 | 2003-06-21 | Shipley Co Llc | Antireflective composition, method for forming antireflective coating layer, and method for manufacturing electronic device |
| US6479879B1 (en) | 2000-11-16 | 2002-11-12 | Advanced Micro Devices, Inc. | Low defect organic BARC coating in a semiconductor structure |
| JP3660941B2 (ja) | 2000-12-15 | 2005-06-15 | 東京都 | 分解性高分子化合物 |
| US6582343B2 (en) * | 2001-01-16 | 2003-06-24 | David Lin | Adjustable step exerciser |
| US20020094593A1 (en) | 2001-01-16 | 2002-07-18 | Taiwan Semiconductor Manufacturing Co., Ltd. | Method for adjusting optical properties of an anti-reflective coating layer |
| WO2002065212A1 (fr) | 2001-02-09 | 2002-08-22 | Asahi Glass Company, Limited | Composition de reserve |
| TW594416B (en) | 2001-05-08 | 2004-06-21 | Shipley Co Llc | Photoimageable composition |
| US6596404B1 (en) | 2001-07-26 | 2003-07-22 | Dow Corning Corporation | Siloxane resins |
| US6743885B2 (en) | 2001-07-31 | 2004-06-01 | Sumitomo Chemical Company, Limited | Resin composition for intermediate layer of three-layer resist |
| US6723488B2 (en) | 2001-11-07 | 2004-04-20 | Clariant Finance (Bvi) Ltd | Photoresist composition for deep UV radiation containing an additive |
| WO2003044600A1 (en) | 2001-11-15 | 2003-05-30 | Honeywell International Inc. | Spin-on anti-reflective coatings for photolithography |
| JP4184813B2 (ja) | 2002-02-19 | 2008-11-19 | コダックグラフィックコミュニケーションズ株式会社 | 感光性組成物、感光性平版印刷版およびこれを用いた平版印刷版の作製方法 |
| US6916592B2 (en) | 2002-03-25 | 2005-07-12 | Shin-Etsu Chemical Co., Ltd. | Esters, polymers, resist compositions and patterning process |
| US6737117B2 (en) | 2002-04-05 | 2004-05-18 | Dow Corning Corporation | Hydrosilsesquioxane resin compositions having improved thin film properties |
| US6730454B2 (en) | 2002-04-16 | 2004-05-04 | International Business Machines Corporation | Antireflective SiO-containing compositions for hardmask layer |
| US6919161B2 (en) | 2002-07-02 | 2005-07-19 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing polymer, resist composition and patterning process |
| KR100510999B1 (ko) | 2002-07-22 | 2005-08-31 | 주식회사 하이닉스반도체 | 반도체 소자의 패턴 형성 방법 |
| US7108958B2 (en) | 2002-07-31 | 2006-09-19 | Brewer Science Inc. | Photosensitive bottom anti-reflective coatings |
| KR100455393B1 (ko) * | 2002-08-12 | 2004-11-06 | 삼성전자주식회사 | 리프레시 플래그를 발생시키는 반도체 메모리 장치 및반도체 메모리 시스템. |
| TW200413417A (en) | 2002-10-31 | 2004-08-01 | Arch Spec Chem Inc | Novel copolymer, photoresist compositions thereof and deep UV bilayer system thereof |
| WO2004044025A2 (en) | 2002-11-12 | 2004-05-27 | Honeywell International Inc | Anti-reflective coatings for photolithography and methods of preparation thereof |
| JP2004161875A (ja) * | 2002-11-13 | 2004-06-10 | Shin Etsu Chem Co Ltd | 多孔質膜形成用組成物、多孔質膜とその製造方法、層間絶縁間膜及び半導体装置 |
| JP2004177952A (ja) | 2002-11-20 | 2004-06-24 | Rohm & Haas Electronic Materials Llc | 多層フォトレジスト系 |
| US7264913B2 (en) | 2002-11-21 | 2007-09-04 | Az Electronic Materials Usa Corp. | Antireflective compositions for photoresists |
| TWI272655B (en) | 2002-11-27 | 2007-02-01 | Tokyo Ohka Kogyo Co Ltd | Forming method of multi-layer wiring for semiconductor |
| TW200424767A (en) | 2003-02-20 | 2004-11-16 | Tokyo Ohka Kogyo Co Ltd | Immersion exposure process-use resist protection film forming material, composite film, and resist pattern forming method |
| US7863396B2 (en) | 2003-03-07 | 2011-01-04 | Chisso Corporation | Silicon compounds |
| EP1469564B1 (de) * | 2003-04-17 | 2012-12-05 | Autoliv Development AB | Pyromechanisches Batteriepol-Trennelement |
| US7368173B2 (en) | 2003-05-23 | 2008-05-06 | Dow Corning Corporation | Siloxane resin-based anti-reflective coating composition having high wet etch rate |
| US7202013B2 (en) | 2003-06-03 | 2007-04-10 | Shin-Etsu Chemical Co., Ltd. | Antireflective film material, and antireflective film and pattern formation method using the same |
| US7303785B2 (en) | 2003-06-03 | 2007-12-04 | Shin-Etsu Chemical Co., Ltd. | Antireflective film material, and antireflective film and pattern formation method using the same |
| US7625687B2 (en) | 2003-07-03 | 2009-12-01 | Dow Corning Corporation | Silsesquioxane resin |
| US7223517B2 (en) | 2003-08-05 | 2007-05-29 | International Business Machines Corporation | Lithographic antireflective hardmask compositions and uses thereof |
| US7115532B2 (en) | 2003-09-05 | 2006-10-03 | Micron Technolgoy, Inc. | Methods of forming patterned photoresist layers over semiconductor substrates |
| JP4355943B2 (ja) | 2003-10-03 | 2009-11-04 | 信越化学工業株式会社 | フォトレジスト下層膜形成材料及びパターン形成方法 |
| US7270931B2 (en) | 2003-10-06 | 2007-09-18 | International Business Machines Corporation | Silicon-containing compositions for spin-on ARC/hardmask materials |
| JP5348843B2 (ja) | 2003-10-07 | 2013-11-20 | ハネウエル・インターナシヨナル・インコーポレーテツド | 集積回路用途の被覆およびハードマスク組成物、これらの製造方法および使用 |
| US20050123760A1 (en) | 2003-10-15 | 2005-06-09 | Cammack J. K. | Light-emitting nanoparticle compositions |
| KR100570206B1 (ko) | 2003-10-15 | 2006-04-12 | 주식회사 하이닉스반도체 | 유기 반사방지막용 광 흡수제 중합체 및 이의 제조 방법과상기 중합체를 포함하는 유기 반사 방지막 조성물 |
| US6939664B2 (en) | 2003-10-24 | 2005-09-06 | International Business Machines Corporation | Low-activation energy silicon-containing resist system |
| US8053159B2 (en) | 2003-11-18 | 2011-11-08 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
| US20050118541A1 (en) | 2003-11-28 | 2005-06-02 | Applied Materials, Inc. | Maintenance of photoresist adhesion and activity on the surface of dielectric ARCS for 90 nm feature sizes |
| JP4340167B2 (ja) | 2004-02-03 | 2009-10-07 | 信越化学工業株式会社 | 珪素含有レジスト下層膜材料及びパターン形成方法 |
| WO2005100445A1 (ja) * | 2004-04-16 | 2005-10-27 | Jsr Corporation | 光半導体封止用組成物、光半導体封止材および光半導体封止用組成物の製造方法 |
| JP4553113B2 (ja) | 2004-06-10 | 2010-09-29 | 信越化学工業株式会社 | 多孔質膜形成用組成物、パターン形成方法、及び多孔質犠性膜 |
| JP4491283B2 (ja) | 2004-06-10 | 2010-06-30 | 信越化学工業株式会社 | 反射防止膜形成用組成物を用いたパターン形成方法 |
| US7691556B2 (en) | 2004-09-15 | 2010-04-06 | Az Electronic Materials Usa Corp. | Antireflective compositions for photoresists |
| ATE400672T1 (de) | 2004-12-17 | 2008-07-15 | Dow Corning | Verfahren zur ausbildung einer antireflexionsbeschichtung |
| CN101072813B (zh) | 2004-12-17 | 2011-06-08 | 陶氏康宁公司 | 硅氧烷树脂涂料 |
| US7816071B2 (en) | 2005-02-10 | 2010-10-19 | Az Electronic Materials Usa Corp. | Process of imaging a photoresist with multiple antireflective coatings |
| JP5296297B2 (ja) | 2005-04-04 | 2013-09-25 | 東レ・ファインケミカル株式会社 | 縮合多環式炭化水素基を有するシリコーン共重合体及びその製造方法 |
| JP4602842B2 (ja) | 2005-06-07 | 2010-12-22 | 東京応化工業株式会社 | 反射防止膜形成用組成物、それを用いた反射防止膜 |
| JP5080250B2 (ja) * | 2005-06-07 | 2012-11-21 | 東京応化工業株式会社 | 反射防止膜形成用組成物、およびこれを用いた反射防止膜 |
| EP1742108B1 (en) | 2005-07-05 | 2015-10-28 | Rohm and Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
| JP2009501064A (ja) | 2005-07-14 | 2009-01-15 | アイ−スタット コーポレイション | 光形成シリコンセンサ膜 |
| EP1762895B1 (en) | 2005-08-29 | 2016-02-24 | Rohm and Haas Electronic Materials, L.L.C. | Antireflective Hard Mask Compositions |
| JP4742943B2 (ja) | 2005-09-06 | 2011-08-10 | ソニー株式会社 | 反射防止膜及び露光方法 |
| US20090105360A1 (en) | 2005-10-28 | 2009-04-23 | Toray Industries, Inc. | Siloxane resin composition and production method thereof |
| US7678529B2 (en) | 2005-11-21 | 2010-03-16 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing film forming composition, silicon-containing film serving as etching mask, substrate processing intermediate, and substrate processing method |
| JP4597844B2 (ja) | 2005-11-21 | 2010-12-15 | 信越化学工業株式会社 | フォトレジスト膜のリワーク方法 |
| JP2007279459A (ja) | 2006-04-07 | 2007-10-25 | Asahi Kasei Corp | 屈折率制御薄膜 |
| EP1845132B8 (en) | 2006-04-11 | 2009-04-01 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing film-forming composition, silicon-containing film, silicon-containing film-bearing substrate, and patterning method |
| WO2007144452A1 (en) * | 2006-06-13 | 2007-12-21 | Braggone Oy | Hybrid inorganic-organic polymer compositions for anti-reflective coatings |
| JP2009540085A (ja) * | 2006-06-13 | 2009-11-19 | ブラゴーン オサケ ユキチュア | 反射防止被膜用のカルボシラン重合体組成物 |
| US7855043B2 (en) | 2006-06-16 | 2010-12-21 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing film-forming composition, silicon-containing film, silicon-containing film-bearing substrate, and patterning method |
| JP4716040B2 (ja) * | 2006-06-16 | 2011-07-06 | 信越化学工業株式会社 | ケイ素含有膜形成用組成物、ケイ素含有膜、ケイ素含有膜形成基板及びこれを用いたパターン形成方法 |
| US7704670B2 (en) * | 2006-06-22 | 2010-04-27 | Az Electronic Materials Usa Corp. | High silicon-content thin film thermosets |
| US20070298349A1 (en) | 2006-06-22 | 2007-12-27 | Ruzhi Zhang | Antireflective Coating Compositions Comprising Siloxane Polymer |
| US7816069B2 (en) | 2006-06-23 | 2010-10-19 | International Business Machines Corporation | Graded spin-on organic antireflective coating for photolithography |
| US7776516B2 (en) | 2006-07-18 | 2010-08-17 | Applied Materials, Inc. | Graded ARC for high NA and immersion lithography |
| US7300730B1 (en) | 2006-09-26 | 2007-11-27 | Tokyo Electron Limited | Creating an optically tunable anti-reflective coating |
| US7416834B2 (en) | 2006-09-27 | 2008-08-26 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
| US7736837B2 (en) | 2007-02-20 | 2010-06-15 | Az Electronic Materials Usa Corp. | Antireflective coating composition based on silicon polymer |
| US20100093969A1 (en) | 2007-02-26 | 2010-04-15 | Ruzhi Zhang | Process for making siloxane polymers |
| WO2008104881A1 (en) | 2007-02-27 | 2008-09-04 | Az Electronic Materials Usa Corp. | Silicon-based antifrelective coating compositions |
| US20080311530A1 (en) | 2007-06-15 | 2008-12-18 | Allen Robert D | Graded topcoat materials for immersion lithography |
| US20090162800A1 (en) | 2007-12-20 | 2009-06-25 | David Abdallah | Process for Imaging a Photoresist Coated over an Antireflective Coating |
| US20090274974A1 (en) | 2008-04-30 | 2009-11-05 | David Abdallah | Spin-on graded k silicon antireflective coating |
| US20100291475A1 (en) | 2009-05-12 | 2010-11-18 | Chenghong Li | Silicone Coating Compositions |
-
2007
- 2007-02-20 US US11/676,673 patent/US8026040B2/en active Active
-
2008
- 2008-01-30 TW TW097103591A patent/TWI409310B/zh active
- 2008-02-15 JP JP2009550335A patent/JP5458306B2/ja active Active
- 2008-02-15 KR KR1020097016856A patent/KR101429317B1/ko active IP Right Grant
- 2008-02-15 EP EP11195180.2A patent/EP2450412B1/en active Active
- 2008-02-15 EP EP08709863.8A patent/EP2121857B1/en not_active Not-in-force
- 2008-02-15 CN CN2008800056175A patent/CN101617010B/zh active Active
- 2008-02-15 WO PCT/IB2008/000432 patent/WO2008102256A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040137241A1 (en) * | 2003-01-08 | 2004-07-15 | International Business Machines Corporation | Patternable low dielectric constsnt materials and their use in ULSI interconnection |
| WO2007011057A1 (ja) * | 2005-07-19 | 2007-01-25 | Dow Corning Toray Co., Ltd. | ポリシロキサンおよびその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2450412B1 (en) | 2019-08-28 |
| EP2450412A1 (en) | 2012-05-09 |
| CN101617010A (zh) | 2009-12-30 |
| KR20090128386A (ko) | 2009-12-15 |
| JP5458306B2 (ja) | 2014-04-02 |
| KR101429317B1 (ko) | 2014-09-19 |
| TWI409310B (zh) | 2013-09-21 |
| JP2010519361A (ja) | 2010-06-03 |
| US8026040B2 (en) | 2011-09-27 |
| EP2121857A1 (en) | 2009-11-25 |
| US20080196626A1 (en) | 2008-08-21 |
| TW200906989A (en) | 2009-02-16 |
| WO2008102256A1 (en) | 2008-08-28 |
| EP2121857B1 (en) | 2014-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101617010B (zh) | 有机硅涂料组合物 | |
| JP5412037B2 (ja) | シロキサン樹脂、シロキサン樹脂の調製方法および抗反射コーティング組成物 | |
| CN103562793B (zh) | 感光性硅氧烷树脂组合物 | |
| JP5632387B2 (ja) | 湿式エッチング可能な反射防止膜 | |
| CN101970540B (zh) | 倍半硅氧烷树脂 | |
| CN101617011A (zh) | 基于硅聚合物的抗反射涂料组合物 | |
| KR101690159B1 (ko) | 변환가능한 반사방지 코팅 | |
| EP2250213A2 (en) | Silsesquioxane resins | |
| JP5863266B2 (ja) | シロキサン樹脂含有塗布組成物 | |
| JP2009541519A (ja) | 高ケイ素含有薄膜熱硬化性樹脂 | |
| KR20110096063A (ko) | 실세스퀴옥산 수지 | |
| WO2013157643A1 (ja) | ラジカル架橋性基を有するポリシロキサン組成物 | |
| KR101589165B1 (ko) | 실란계 조성물 및 그 경화막, 및 그것을 이용한 네거티브형 레지스트 패턴의 형성 방법 | |
| JP4541080B2 (ja) | 反射防止膜形成用組成物およびこれを用いた配線形成方法 | |
| CN102918460A (zh) | 感光性硅氧烷组合物、由其形成的固化膜和具有固化膜的元件 | |
| CN101622297A (zh) | 制备硅氧烷聚合物的方法 | |
| US10947412B2 (en) | Crack-resistant silicon-based planarizing compositions, methods and films | |
| JP5744812B2 (ja) | 硬化性樹脂組成物、光学部材セット、その製造方法、これを用いた固体撮像素子 | |
| JP2010519375A (ja) | 集積回路用高シリコン含量シロキサンポリマー | |
| WO2017090917A1 (ko) | 감광성 수지 조성물, 그로부터 형성된 경화막, 및 경화막을 갖는 소자 | |
| JP6022870B2 (ja) | 感光性樹脂組成物 | |
| WO2017110623A1 (ja) | シリコーン樹脂組成物および半導体発光素子用封止材 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: MERCK PATENT GMBH Free format text: FORMER OWNER: AZ ELECTRONIC MATERIALS USA CO. Effective date: 20150409 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20150409 Address after: Darmstadt Patentee after: Merck Patent GmbH Address before: American New Jersey Patentee before: AZ Electronic Materials USA |