CN101622296B - 硅基抗反射涂料组合物 - Google Patents
硅基抗反射涂料组合物 Download PDFInfo
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- CN101622296B CN101622296B CN2008800064415A CN200880006441A CN101622296B CN 101622296 B CN101622296 B CN 101622296B CN 2008800064415 A CN2008800064415 A CN 2008800064415A CN 200880006441 A CN200880006441 A CN 200880006441A CN 101622296 B CN101622296 B CN 101622296B
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- Prior art keywords
- group
- silane
- solvent
- alkyl
- siloxane polymer
- Prior art date
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title description 29
- 229910052710 silicon Inorganic materials 0.000 title description 28
- 239000010703 silicon Substances 0.000 title description 27
- 239000008199 coating composition Substances 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims abstract description 57
- 239000002904 solvent Substances 0.000 claims abstract description 53
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910008051 Si-OH Inorganic materials 0.000 claims abstract description 16
- 229910006358 Si—OH Inorganic materials 0.000 claims abstract description 16
- 238000009833 condensation Methods 0.000 claims abstract description 14
- 230000005494 condensation Effects 0.000 claims abstract description 14
- 230000032683 aging Effects 0.000 claims abstract description 9
- 125000000524 functional group Chemical group 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 56
- -1 2-4Thiazolinyl Chemical group 0.000 claims description 40
- 239000011248 coating agent Substances 0.000 claims description 36
- 238000000576 coating method Methods 0.000 claims description 36
- 229910000077 silane Inorganic materials 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000006117 anti-reflective coating Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910009257 Y—Si Inorganic materials 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
- 238000007348 radical reaction Methods 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 100
- 239000000463 material Substances 0.000 description 70
- 239000000243 solution Substances 0.000 description 70
- 238000010790 dilution Methods 0.000 description 55
- 239000012895 dilution Substances 0.000 description 55
- 239000011541 reaction mixture Substances 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- 230000008569 process Effects 0.000 description 41
- 238000001914 filtration Methods 0.000 description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 31
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 31
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 125000003545 alkoxy group Chemical group 0.000 description 28
- 239000010410 layer Substances 0.000 description 27
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 25
- 238000003760 magnetic stirring Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- 238000005303 weighing Methods 0.000 description 18
- 239000004810 polytetrafluoroethylene Substances 0.000 description 17
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 238000004528 spin coating Methods 0.000 description 17
- 230000010287 polarization Effects 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 238000010521 absorption reaction Methods 0.000 description 15
- 238000005530 etching Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 229920002120 photoresistant polymer Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001118 alkylidene group Chemical group 0.000 description 6
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 6
- 238000003384 imaging method Methods 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 229920001059 synthetic polymer Polymers 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000003667 anti-reflective effect Effects 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 3
- 238000012940 design transfer Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000001259 photo etching Methods 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WGRZHLPEQDVPET-UHFFFAOYSA-N 2-methoxyethoxysilane Chemical compound COCCO[SiH3] WGRZHLPEQDVPET-UHFFFAOYSA-N 0.000 description 2
- DAJFVZRDKCROQC-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propyl-tripropoxysilane Chemical compound CCCO[Si](OCCC)(OCCC)CCCOCC1CO1 DAJFVZRDKCROQC-UHFFFAOYSA-N 0.000 description 2
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010073306 Exposure to radiation Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- YACCECLVHQLZQK-UHFFFAOYSA-N methoxyperoxyethane Chemical compound CCOOOC YACCECLVHQLZQK-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 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
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- ZQUROMIGLUXXNW-UHFFFAOYSA-N 1-triethoxysilylpropan-2-ol Chemical compound CCO[Si](CC(C)O)(OCC)OCC ZQUROMIGLUXXNW-UHFFFAOYSA-N 0.000 description 1
- AFAZQMFMBKQIDW-UHFFFAOYSA-N 1-trimethoxysilylpropan-2-ol Chemical compound CO[Si](OC)(OC)CC(C)O AFAZQMFMBKQIDW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZQFIAAFKCPCOQZ-UHFFFAOYSA-N 2-chloro-2,3-dimethylbutane silane Chemical compound [SiH4].CC(C(C)(C)Cl)C ZQFIAAFKCPCOQZ-UHFFFAOYSA-N 0.000 description 1
- YYJNOEZFFSJVDD-UHFFFAOYSA-N 2-chloroethoxy-diethoxy-phenylsilane Chemical compound ClCCO[Si](OCC)(OCC)C1=CC=CC=C1 YYJNOEZFFSJVDD-UHFFFAOYSA-N 0.000 description 1
- IKBFHCBHLOZDKH-UHFFFAOYSA-N 2-chloroethyl(triethoxy)silane Chemical compound CCO[Si](CCCl)(OCC)OCC IKBFHCBHLOZDKH-UHFFFAOYSA-N 0.000 description 1
- CASYTJWXPQRCFF-UHFFFAOYSA-N 2-chloroethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCl CASYTJWXPQRCFF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZHTLMPWATZQGAP-UHFFFAOYSA-N 2-triethoxysilylethanol Chemical compound CCO[Si](CCO)(OCC)OCC ZHTLMPWATZQGAP-UHFFFAOYSA-N 0.000 description 1
- BOSZBTFBHSYELP-UHFFFAOYSA-N 2-trimethoxysilylethanol Chemical compound CO[Si](OC)(OC)CCO BOSZBTFBHSYELP-UHFFFAOYSA-N 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- NMUBRRLYMADSGF-UHFFFAOYSA-N 3-triethoxysilylpropan-1-ol Chemical compound CCO[Si](OCC)(OCC)CCCO NMUBRRLYMADSGF-UHFFFAOYSA-N 0.000 description 1
- YATIYDNBFHEOFA-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-ol Chemical compound CO[Si](OC)(OC)CCCO YATIYDNBFHEOFA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910018125 Al-Si Inorganic materials 0.000 description 1
- 229910018520 Al—Si Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFKRFJVCWAKTSD-UHFFFAOYSA-N C(N)(OCC)=O.C(C)O[Si](OCC)(OCC)SSSSCCC Chemical compound C(N)(OCC)=O.C(C)O[Si](OCC)(OCC)SSSSCCC UFKRFJVCWAKTSD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- BCSZALSGPTYQQW-UHFFFAOYSA-N O(C)[SiH](OC)OC.[Cl] Chemical compound O(C)[SiH](OC)OC.[Cl] BCSZALSGPTYQQW-UHFFFAOYSA-N 0.000 description 1
- IJUZIFGEBYXQJT-UHFFFAOYSA-N O(CC)[SiH](OCC)OCC.[Cl] Chemical compound O(CC)[SiH](OCC)OCC.[Cl] IJUZIFGEBYXQJT-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910008284 Si—F Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229910008938 W—Si Inorganic materials 0.000 description 1
- RQVFGTYFBUVGOP-UHFFFAOYSA-N [acetyloxy(dimethyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)OC(C)=O RQVFGTYFBUVGOP-UHFFFAOYSA-N 0.000 description 1
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012965 benzophenone Substances 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
- 235000010290 biphenyl Nutrition 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
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical compound CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NPVQBEIMNWDKEU-UHFFFAOYSA-N chloromethoxy-dimethoxy-phenylsilane Chemical compound ClCO[Si](OC)(OC)C1=CC=CC=C1 NPVQBEIMNWDKEU-UHFFFAOYSA-N 0.000 description 1
- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical compound CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 0.000 description 1
- FPOSCXQHGOVVPD-UHFFFAOYSA-N chloromethyl(trimethoxy)silane Chemical compound CO[Si](CCl)(OC)OC FPOSCXQHGOVVPD-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ATGKAFZFOALBOF-UHFFFAOYSA-N cyclohexyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCCC1 ATGKAFZFOALBOF-UHFFFAOYSA-N 0.000 description 1
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- DGPFXVBYDAVXLX-UHFFFAOYSA-N dibutyl(diethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)CCCC DGPFXVBYDAVXLX-UHFFFAOYSA-N 0.000 description 1
- YPENMAABQGWRBR-UHFFFAOYSA-N dibutyl(dimethoxy)silane Chemical compound CCCC[Si](OC)(OC)CCCC YPENMAABQGWRBR-UHFFFAOYSA-N 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- UDFQIGODCFRNJY-UHFFFAOYSA-N diethoxy(dihexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)CCCCCC UDFQIGODCFRNJY-UHFFFAOYSA-N 0.000 description 1
- YETKAVVSNLUTEQ-UHFFFAOYSA-N diethoxy(dioctyl)silane Chemical compound CCCCCCCC[Si](OCC)(OCC)CCCCCCCC YETKAVVSNLUTEQ-UHFFFAOYSA-N 0.000 description 1
- ZWTJVXCCMKLQKS-UHFFFAOYSA-N diethoxy(ethyl)silicon Chemical compound CCO[Si](CC)OCC ZWTJVXCCMKLQKS-UHFFFAOYSA-N 0.000 description 1
- XYQBLHWXVQOUID-UHFFFAOYSA-N diethoxy(heptyl)silane Chemical class C(CCCCCC)[SiH](OCC)OCC XYQBLHWXVQOUID-UHFFFAOYSA-N 0.000 description 1
- DVAZURRZYNXADH-UHFFFAOYSA-N diethoxy(pentyl)silane Chemical class CCCCC[SiH](OCC)OCC DVAZURRZYNXADH-UHFFFAOYSA-N 0.000 description 1
- VVKJJEAEVBNODX-UHFFFAOYSA-N diethoxy-di(propan-2-yl)silane Chemical compound CCO[Si](C(C)C)(C(C)C)OCC VVKJJEAEVBNODX-UHFFFAOYSA-N 0.000 description 1
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- CYICXDQJFWXGTC-UHFFFAOYSA-N dihexyl(dimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)CCCCCC CYICXDQJFWXGTC-UHFFFAOYSA-N 0.000 description 1
- TYXIAHKLJMLPIP-UHFFFAOYSA-N dimethoxy(dioctyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)CCCCCCCC TYXIAHKLJMLPIP-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
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- DWYGLGYVAMEOSL-UHFFFAOYSA-N dimethoxy(pentyl)silane Chemical compound CCCCC[SiH](OC)OC DWYGLGYVAMEOSL-UHFFFAOYSA-N 0.000 description 1
- VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000003983 fluorenyl group Chemical class 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
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- CIRVHLPTDBACSH-UHFFFAOYSA-N heptyl(dimethoxy)silane Chemical compound C(CCCCCC)[SiH](OC)OC CIRVHLPTDBACSH-UHFFFAOYSA-N 0.000 description 1
- VRINOTYEGADLMW-UHFFFAOYSA-N heptyl(trimethoxy)silane Chemical compound CCCCCCC[Si](OC)(OC)OC VRINOTYEGADLMW-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- CZWLNMOIEMTDJY-UHFFFAOYSA-N hexyl(trimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)OC CZWLNMOIEMTDJY-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 206010020745 hyperreflexia Diseases 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 description 1
- WJJDBJYEDVQKGT-UHFFFAOYSA-N triethoxy(phenanthren-9-yl)silane Chemical compound C1=CC=C2C([Si](OCC)(OCC)OCC)=CC3=CC=CC=C3C2=C1 WJJDBJYEDVQKGT-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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- 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
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
- H01L21/02134—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC the material comprising hydrogen silsesquioxane, e.g. HSQ
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
- H01L21/3122—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds
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Abstract
提供了一种聚合物,其包含具有至少一个Si-OH基团和至少一个Si-OR基团的硅氧烷聚合物,其中R是任选地具有反应性官能团的缩合稳定基团,其中所述硅氧烷聚合物,当被放入溶剂中时,在40℃老化一周之后由GPC测定的重均分子量增量小于或等于50%。
Description
发明领域
本发明涉及具有改善的稳定性的硅基抗反射涂料(ARC)/硬质掩模组合物。
背景技术
在微电子工业中,趋势是减小结构特征的尺寸。采用有效的光致抗蚀剂的微刻法提供可行的技术。然而,随着特征小型化继续发展,也需要减小光致抗蚀剂厚度。对于一些光刻成像工艺,用于先进的微刻法的薄光致抗蚀剂不再能够为基底蚀刻提供足够的掩蔽预算以便在高保真度下实现图案转移。
该问题的一种解决方案是使用在光致抗蚀剂下方的层,其不仅用作抗反射涂层,而且提供足够的蚀刻选择性。这种增强的蚀刻选择性将会容许该衬层(underlayer)用作图像转移媒介物。在当前的现有技术发展中,将含硅的底部抗反射涂层用于满足该目的。
对于一些光刻成像工艺,所用的抗蚀剂无法为随后的蚀刻步骤提供足够的耐受性(掩蔽)以使期望的图案能够有效转移到该抗蚀剂下方的层。在许多情况下(例如,在期望超薄抗蚀剂层的情况下,在待蚀刻的下方材料厚的情况下,在需要显著的蚀刻深度的情况下,和/或在对于给定的下方材料期望使用某些蚀刻剂的情况下),居于抗蚀剂层与待通过从经构图的抗蚀剂转移而形成图案的下方材料中间使用所谓的硬质掩模。硬质掩模层从经构图的抗蚀剂层接收图案并且应当能够经受将该图案转移至下方材料所需的蚀刻过程。
在光致抗蚀剂无法提供足够的干法蚀刻耐受性的情况下,衬层与抗反射性能的组合可以充当硬质掩模。通过用氟化气体蚀刻可以容易地将抗蚀剂图像转移到含有机硅的抗反射涂层上,因为F对有机硅官能团呈高度反应性,它使该涂层分解成气态的Si-F物质。当穿透(break through)Si硬质掩模时这是非常必要的。另一方面,当蚀刻过程中使用氧气时高Si含量的掩模具有优异的耐蚀刻性,因为SiO2形成产生硬质掩模同时有机衬层得以被蚀刻。与光致抗蚀剂一样,有机衬层充当基底蚀刻的掩模。本质上,当希望在不同条件下具有高的耐蚀刻性和低的耐蚀刻性时,使用三层体系。在三层体系中,底层(bottom layer)(通常是碳基衬层)形成于基底(例如Si型基底)上,在底层之上涂布硅基层(Si-BARC),然后在该硅基层之上形成光致抗蚀剂。将各层之间基本差异的要求与抗反射性能组合对于光刻法和图案转移而言都是非常期望的。
另外,在下方材料层对用于使抗蚀剂层构图的成像辐射呈过度反射性时,通常在衬层与抗蚀剂层之间施加薄的抗反射涂层。一些情况下,抗反射和硬质掩模功能可以由同一种材料提供。
虽然现有技术中存在许多硬质掩模和抗反射涂层材料,仍然希望改进的组合物。许多现有技术材料具有稳定性问题,这减少了其储存期限,因而难以使用。将期望获得具有改善的稳定性和延长的储存期限的硅基抗反射涂料/硬质掩模组合物。
发明概述
本发明涉及一种聚合物,其包含具有至少一个Si-OH基团和至少一个Si-OR基团的硅氧烷聚合物,其中R是任选地具有反应性官能团的缩合稳定基团,其中所述硅氧烷聚合物,当被放入溶剂中时,在40℃老化一周之后由GPC测定的重均分子量增量小于或等于50%。一些情况下,Si-OH基团和Si-OR基团以约1∶5-约5∶1、优选约1∶5-约1∶1的比率存在。本发明还提供一种涂布的基底,该基底在其上具有上述抗反射涂料组合物的涂膜,该涂布的基底例如是硅片或有机(碳基)衬层。另外,本发明还提供一种形成光刻浮雕图像(photorelief image)的方法,其中基底在其上具有抗反射涂料组合物的层,然后向其施加化学放大光致抗蚀剂组合物。该基底优选是碳基衬层。
发明详述
本发明涉及一种聚合物,其包含具有至少一个Si-OH基团和至少一个Si-OR基团的硅氧烷聚合物,其中R是任选地具有反应性官能团的缩合稳定基团,其中所述硅氧烷聚合物在放入溶剂中时,在40℃老化一周之后由GPC测定的重均分子量增量小于或等于50%。
优选地,所述醇选自异丙醇、正丁醇、异丁醇、叔丁醇、1,2-丙二醇、1,2,3-丙三醇、乳酸乙酯、丙二醇单甲醚、2-甲基-2-丙醇、前述化合物的部分氟化和全氟化的形式、及其混合物。
所述聚合物优选地,在R1、R2和R3中各自是C1-10烷基或芳基和R4是C1-10烷氧基或卤素,或者R1、R2、R3和R4各自是C1-10烷氧基、卤素、甲硅烷氧基或甲硅烷氧基硅烷,或者R1和R2各自是C1-10烷氧基、卤素、甲硅烷氧基或甲硅烷氧基硅烷以及R3和R4各自是C1-10烷基或芳基,或者R1、R2和R3各自是C1-10烷氧基、卤素、甲硅烷氧基或甲硅烷氧基硅烷和R4是C1-10烷基或芳基。
所述缩合稳定基团可以选自三甲氧基硅烷、三乙氧基硅烷、甲基二甲氧基硅烷、乙基二乙氧基硅烷、甲基二甲氧基氯硅烷、甲基甲氧基二氯硅烷、二苯基二氯硅烷、二甲基叔丁基氯硅烷、二甲基甲氧基氯硅烷、甲基二甲氧基氯硅烷、乙基甲氧基二氯硅烷、二乙基甲氧基氯硅烷、四甲氧基硅烷、四乙氧基硅烷、四正丙氧基硅烷、四异丙氧基硅烷、四正丁氧基硅烷、甲基三甲氧基硅烷、甲基三乙氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、正丙基三甲氧基硅烷、正丙基三乙氧基硅烷、异丙基三甲氧基硅烷、异丙基三乙氧基硅烷、正丁基三甲氧基硅烷、正丁基三乙氧基硅烷、正戊基三甲氧基硅烷、正己基三甲氧基硅烷、正庚基三甲氧基硅烷、正辛基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、环己基三甲氧基硅烷、环己基三乙氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、3-氯丙基三甲氧基硅烷、3-氯丙基三乙氧基硅烷、3,3,3-三氟丙基三甲氧基硅烷、3,3,3-三氟丙基三乙氧基硅烷、2-羟基乙基三甲氧基硅烷、2-羟基乙基三乙氧基硅烷、2-羟基丙基三甲氧基硅烷、2-羟基丙基三乙氧基硅烷、3-羟基丙基三甲氧基硅烷、3-羟基丙基三乙氧基硅烷、3-巯基丙基三甲氧基硅烷、3-巯基丙基三乙氧基硅烷、3-异氰酸酯丙基三甲氧基硅烷、3-异氰酸酯丙基三乙氧基硅烷、3-缩水甘油氧基丙基三甲氧基硅烷、3-缩水甘油氧基丙基三乙氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、2-(3,4-环氧环己基)乙基-三乙氧基硅烷、(3-缩水甘油氧基丙基)三丙氧基硅烷、3-缩水甘油氧基丙基三(2-甲氧基乙氧基)硅烷、2,3-环氧丙基三乙氧基硅烷、3,4-环氧丁基三乙氧基硅烷、4,5-环氧戊基三乙氧基硅烷、5,6-环氧己基三乙氧基硅烷、5,6-环氧己基三甲氧基硅烷、4-(三甲氧基甲硅烷基)丁烷-1,2-环氧化物、3-(三乙氧基甲硅烷基)丙基琥珀酸酐、3-(三甲氧基甲硅烷基)丙基琥珀酸酐、3-(甲基二甲氧基甲硅烷基)丙基琥珀酸酐、3-(甲基二乙氧基甲硅烷基)丙基琥珀酸酐、3-脲基丙基三甲氧基硅烷、3-脲基丙基三乙氧基硅烷、二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、二乙基二甲氧基硅烷、二乙基二乙氧基硅烷、二正丙基二甲氧基硅烷、二正丙基二乙氧基硅烷、二异丙基二甲氧基硅烷、二异丙基二乙氧基硅烷、二正丁基二甲氧基硅烷、二正丁基二乙氧基硅烷、二正戊基二甲氧基硅烷、二正戊基二乙氧基硅烷、二正己基二甲氧基硅烷、二正己基二乙氧基硅烷、二正庚基二甲氧基硅烷、二正庚基二乙氧基硅烷、二正辛基二甲氧基硅烷、二正辛基二乙氧基硅烷、二n-环己基二甲氧基硅烷、二n-环己基二乙氧基硅烷、二苯基二甲氧基硅烷、二苯基二乙氧基硅烷、甲基三乙酰氧基硅烷、二甲基二乙酰氧基硅烷、N-(3-三乙氧基甲硅烷基丙基)-4-羟基丁酰胺、3-(三乙氧基甲硅烷基丙基)-对硝基苯甲酰胺、三乙氧基甲硅烷基丙基乙基氨基甲酸酯、乙烯基三(甲基乙基酮肟基)硅烷、乙烯基甲基双(甲基乙基酮肟基)硅烷、四(甲基乙基酮肟基)硅烷、苯基三(甲基乙基酮肟基)硅烷、二苯基双(甲基乙基酮肟基)硅烷、二甲基双(甲基乙基酮肟基)硅烷、甲基三(甲基乙基酮肟基)硅烷、2-羟基-4-(3-三乙氧基甲硅烷基丙氧基)二苯基酮、和2-羟基-4-(3-甲基二乙氧基甲硅烷基丙氧基)二苯基酮、及其混合物。
优选地,Y选自亚烷基、-O-亚烷基-O-、亚烷基-O-亚烷基、亚烷基-Z1C(=O)Z2-亚烷基和-O-亚烷基-Z1C(=O)Z2-亚烷基-O-,其中Z1和Z2各自选自直接键或-O-。
更优选地所述缩合稳定基团选自双(三乙氧基甲硅烷基)乙烷、2,2-双(烯丙氧基甲基)-1-三甲基甲硅烷氧基丁烷、2,2-双(3-三乙氧基甲硅烷基丙氧基甲基)-1-三甲基甲硅烷氧基丁烷、3,3-双(三氯甲硅烷基丙氧基甲基)-5-氧杂-十三烷和1,3-双(3-三氯甲硅烷基丙氧基)-2-癸氧基丙烷。
一些情况下,Si-OH基团和Si-OR基团以约1∶5-约5∶1的比率存在。本发明还提供了一种涂布的基底,该基底在其上具有上述抗反射涂料组合物的涂膜,该涂布的基底例如是硅片(或者其他例如SiO2、SiON、SiN、p-Si、α-Si、W、W-Si、Al、Cu、Al-Si等),或者是有机(碳基)衬层。另外,本发明还提供了一种形成光刻浮雕图像的方法,其中基底在其上具有抗反射涂料组合物的层,然后向其施加化学放大光致抗蚀剂组合物。
本发明公开了通过将一些但不是所有的硅烷醇基团或烷氧基甲硅烷基封闭或者通过反应性羟基官能团的甲硅烷基化而使硅氧烷聚合物改性。该改性的硅倍半氧烷聚合物显示增强的稳定性和延长的储存期限。含有可交联官能团和发色团的改性硅倍半氧烷聚合物可以用作光刻工艺中的抗反射涂料或硬质掩模材料。
硅氧烷聚合物是本领域技术人员公知的。硅氧烷聚合物通常由基于M型、D型、T型和Q型命名法的硅基单元构成,其结构在下面显示。
其中Ra、Rb和Rc选自烃基团、环氧官能基团和酸酐官能基团,当结合的氧原子与另一硅原子键接时p的值为0.5,当结合的氧原子与硅原子之外键接时p的值为1。
本发明的聚合物通常包含一个或多个三官能硅氧烷单元(T),
和一个或多个四官能硅氧烷单元(Q),
其中当结合的氧原子与另一硅原子键接时p的值为0.5,当结合的氧原子与硅原子之外键接时p的值为1,条件是每个T和Q单元中的至少一个p具有0.5的值;每个R10独立地选自烷基、烯基、炔基、环烷基、芳基、烷芳基、芳烷基、(烷基)丙烯酸酯、(烷基)丙烯酰氧基烷基、(烷基)丙烯酰氧基烯基、环氧官能基团和酸酐官能基团。大多数情况下,所述硅氧烷聚合物中的T和Q单元的总数将大于或等于50%。
优选地,三官能硅氧烷单元(T)中的至少一个R10为芳基。
T单元和Q单元的实例包括三乙氧基硅烷、四乙氧基硅烷、甲基三乙氧基硅烷、乙基三乙氧基硅烷、正丁基三乙氧基硅烷、苯基三乙氧基硅烷、9-菲基三乙氧基硅烷、苯基三甲氧基硅烷、四甲氧基硅烷、甲基三甲氧基硅烷、甲基三氯硅烷、乙基三氯硅烷、苯基三氯硅烷、氯三乙氧基硅烷、氯三甲氧基硅烷、氯甲基三乙氧基硅烷、氯乙基三乙氧基硅烷、氯苯基三乙氧基硅烷、氯甲基三甲氧基硅烷、氯乙基三甲氧基硅烷和氯苯基三甲氧基硅烷、2-(3,4-环氧环己基)乙基三乙氧基硅烷等。
当通常制成硅氧烷聚合物时,最终结果是具有许多Si-OH键的聚合物。这些Si-OH键则变得容易水解,这使含有这些具有许多Si-OH键的聚合物的组合物不稳定而且具有短的储存期限。
申请人已经发现通过用Si-OR基团代替一些但不是所有的Si-OH基团,含有这些聚合物的组合物更加稳定而且具有更长的储存期限。这可以通过测试该硅氧烷聚合物测定,该聚合物当被放入溶剂中时,在40℃老化一周之后由分子量相对聚苯乙烯标准物的GPC测定的重均分子量增量小于或等于50%。
用Si-OR基团代替一些Si-OH基团时,R是任选地具有反应性官能团的缩合稳定基团。当该缩合稳定基团上存在官能团时,则可以具有在硅氧烷聚合物与其自身或者与其他物质例如交联剂之间的进一步交联。
所述缩合稳定基团可以是醇的残基;具有式R1R2R3SiR4的化合物,其中R1、R2、R3和R4各自独立地选自氢、卤化物、C1-10烷基、C2-4烯基、C3-10环烷基、芳基、C1-10烷氧基、酰氧基、芳氧基、甲硅烷氧基、甲硅烷氧基硅烷、其中R8和R9各自选自C1-10烷基的NR8R9、其中R6和R7各自独立地选自氢、C1-10烷基、或者R6和R7连同它们键合的碳原子一起形成C3-6环烷基环的ON=CR6R7;或者具有式(R12)3Si-Y-Si(R12)3的化合物,其中每个R12独立地选自C1-4烷基、C1-4烷氧基和卤素;和Y是连接基团。
当所述缩合稳定基团是醇的残基时,该基团可以在聚合物合成过程中引入(例如,在醇溶剂中聚合单体或者在非醇溶剂中聚合单体然后将聚合物转移到醇溶剂中),或者在含有该聚合物的抗反射涂料组合物的配制过程中通过使用醇溶剂作为该组合物的一部分而引入。
当所述缩合稳定基团是式R1R2R3SiR4或(R12)3Si-Y-Si(R12)3的化合物时,该化合物可以与聚合物反应,由此使Si-OH基团现在被Si-OR代替。
所述烷基、烯基、环烷基、芳基、烷氧基、酰氧基和芳氧基可以是未取代的或取代的。合适的取代基包括在本发明的范围内不会改变所述基团的性质的那些取代基,例如卤素原子(例如氟、氯、溴、碘)、羟基、烷氧基、巯基、烷基巯基、硝基、亚硝基、氰基、硫酰基(sulfoxy)等。烷基的实例包括甲基、丁基、异戊基等,烯基例如乙烯基、烯丙基等,环烷基例如环己基、环戊基、金刚烷基等,烷氧基例如甲氧基、乙氧基、羟基乙氧基、丙氧基、羟基丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基,芳基例如苯基,芳氧基例如苯氧基,和酰氧基例如乙酰氧基。
环氧官能基团的实例包括(3-缩水甘油氧基丙基)三甲氧基硅烷、(3-缩水甘油氧基丙基)三乙氧基硅烷、(3-缩水甘油氧基丙基)三丙氧基硅烷、3-缩水甘油氧基丙基三(2-甲氧基乙氧基)硅烷、2,3-环氧丙基三乙氧基硅烷、3,4-环氧丁基三乙氧基硅烷、4,5-环氧戊基三乙氧基硅烷、5,6-环氧己基三乙氧基硅烷、5,6-环氧己基三甲氧基硅烷、2-(3,4-环氧环己基)乙基三乙氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、4-(三甲氧基甲硅烷基)丁烷-1,2-环氧化物。酸酐官能基团的实例包括3-(三乙氧基甲硅烷基)丙基琥珀酸酐、3-(三甲氧基甲硅烷基)丙基琥珀酸酐、3-(甲基二甲氧基甲硅烷基)丙基琥珀酸酐和3-(甲基二乙氧基甲硅烷基)丙基琥珀酸酐。
连接基团Y可以选自亚烷基、-O-亚烷基-O-、亚烷基-O-亚烷基、亚烷基-Z1C(=O)Z2-亚烷基和-O-亚烷基-Z1C(=O)Z2-亚烷基-O-,其中Z1和Z2各自选自直接键或-O-。(R12)3Si-Y-Si(R12)3的实例包括双(三乙氧基甲硅烷基)乙烷、2,2-双(烯丙氧基甲基)-1-三甲基甲硅烷氧基丁烷、2,2-双(3-三乙氧基甲硅烷基丙氧基甲基)-1-三甲基甲硅烷氧基丁烷、3,3-双(三氯甲硅烷基丙氧基甲基)-5-氧杂-十三烷和1,3-双(3-三氯甲硅烷基丙氧基)-2-癸氧基丙烷。
一些情况下,芳基将充当发色团,并且可以包括但不限于未取代的和取代的芴、亚乙烯基亚苯基、蒽、苝、苯基、苄基、查耳酮、苯邻二甲酰亚胺、扑酸、吖啶、偶氮化合物、二苯并呋喃、其任何衍生物,噻吩、蒽、萘、苯、查耳酮、苯邻二甲酰亚胺、扑酸、吖啶、偶氮化合物、苯并菲、芘、荧蒽、蒽酮、二苯甲酮、噻吨酮、含有选自氧、氮、硫及其组合的杂原子的杂环芳环、以及前述的衍生物。
一般按照已知的过程和方法制备本发明的组合物。一种实例是通过将抗反射涂料的组分溶解在合适溶剂中而制成的抗反射涂料组合物,所述溶剂例如二元醇醚例如乙二醇单甲醚、丙二醇单甲醚,或醇。通常抗反射涂料组合物的固含量为该抗反射涂料组合物的总重量的1-35wt%。
可以用本领域技术人员公知的技术将组合物涂布在基底上,例如浸涂、旋涂或喷涂。抗反射涂层的膜厚度为约0.01μm-约1μm。将该涂层在加热板上或对流加热箱中或者用其他公知的加热方法加热,从而除去任何残余溶剂以及需要的话引起交联,而且使抗反射涂层不溶解以便防止抗反射涂层与光致抗蚀剂之间的互混。
存在两种光致抗蚀剂组合物:负性作用的和正性作用的。当将负性光致抗蚀剂组合物对辐射进行成像式曝光时,光致抗蚀剂组合物的经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被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材表面的所希望部分露出。
另一方面,当将正性光致抗蚀剂组合物对辐射进行成像式曝光时,经辐射曝光的光致抗蚀剂组合物的那些区域变得更可溶于显影液(例如出现重排反应),而那些未被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涂层的曝光区域并且在光致抗蚀剂涂层中产生正图像。再次使下方表面的所希望部分露出。
负性光致抗蚀剂和正性光致抗蚀剂组合物及其应用是本领域技术人员公知的。
在三层抗蚀剂处理工艺中,用与传统双层抗蚀剂工艺中的相同方法,将底涂层形成材料施加至位于支持基材上的可加工基底(或膜)上以形成底涂层。然后在该底涂层上形成含硅中间层,在该中间层上形成单层的光致抗蚀剂层。接下来,将光致抗蚀剂层的预定区域曝光。通过随后的PEB和显影,形成经构图的光致抗蚀剂层。进一步加工,例如,使用该经构图的光致抗蚀剂层作为掩模并蚀刻中间层,除去经构图的光致抗蚀剂层,通过使用经构图的中间层作为掩模蚀刻底涂层,接着除去该经构图的中间层,之后通过蚀刻加工所述可加工基底。
本发明的工艺包括用本发明组合物涂布基底并且在加热板上或对流加热箱中或用其他公知的加热方法在足够的温度下加热足够的时间以除去涂层溶剂和使聚合物交联,达到足以使得该涂层不溶于光致抗蚀剂的涂布溶液或含水碱性显影剂的程度。此外,该涂层应当在固化期间充分交联以防止聚合物涂层与光致抗蚀剂的涂布溶液之间的互混或扩散。可以施用边胶清洗剂从而用本领域公知的工艺清洁基底的边缘。加热温度范围是约70℃-约250℃。如果温度低于70℃,则发生溶剂损失不充分或交联量不足,在250℃以上的温度下,该聚合物会变得在化学上不稳定。然后在抗反射涂层上面涂布光致抗蚀剂组合物膜并且烘焙以基本上除去光致抗蚀剂溶剂。使光致抗蚀剂成像式曝光并在含水显影剂中显影以除去处理过的抗蚀剂。在显影之前和曝光之后可以在该过程中引入任选的加热步骤。将光致抗蚀剂涂布和成像的工艺是本领域技术人员公知的而且对于所用抗蚀剂的具体种类而优化。经构图的基底可以接着在合适的蚀刻室内进行干法蚀刻以除去抗反射膜的曝光部分,其中残余的光致抗蚀剂充当蚀刻掩模。
下列具体实施例将提供本发明制备和使用组合物的方法的详细说明。然而,这些实施例不意在以任何方式限制或约束本发明的范围并且不应该被看作是提供必须专门使用以实践本发明的条件、参数或数值。
实施例1
在配备磁力搅拌器、温度计和冷凝器的250mL三颈圆底烧瓶中装入35.00g 2-(3,4-环氧环己基)乙基三甲氧基硅烷(142mmol)、8.50g苯基三甲氧基硅烷(43mmol)和4.50g甲基三甲氧基硅烷(33mmol)。向烧瓶中加入7.90g D.I.水、2.00g乙酸和45g THF的混合物。将混合物加热到回流并在该温度保持3小时。然后,将混合物冷却到室温。在降低的压力下除去溶剂以提供45.78g无色液体树脂。通过凝胶渗透色谱法用聚苯乙烯作为参照测定的重均分子量为约2,430g/mol。FT-IR显示羟基的存在。
实施例2
在配备磁力搅拌器、温度计和冷凝器的250mL三颈圆底烧瓶中装入32.10g实施例1中制备的硅倍半氧烷树脂、16.00g三乙胺和16mLTHF。向该混合物中滴加147mL三甲基氯硅烷(四氢呋喃中的1.0M三甲基氯硅烷)并将该混合物保持在10℃以下。滴加完成后,将混合物加热到回流并保持该温度4小时。将混合物冷却到室温并过滤。在降低的压力下除去溶剂。将回收的油溶解在100mL甲苯中并且用D.I.水洗涤有机相(2x100mL)。干燥有机层,过滤,并且在降低的压力下除去溶剂。得到26.77g液体树脂。通过凝胶渗透色谱法用聚苯乙烯作为参照测定的重均分子量为约3,380g/mol。FT-IR显示该改性树脂中几乎没有羟基峰。
将实施例1和实施例2的聚合物的试样放在20mL小瓶中并放置在通风橱中,室温下对大气敞开。3个月后,观察到实施例1聚合物胶凝而且不再可溶于通常的有机溶剂中。相反,实施例2聚合物没有胶凝而且易溶于通常的有机溶剂中。
实施例3
在配备磁力搅拌器、温度计和冷凝器的250mL三颈圆底烧瓶中装入28.00g甲基丙烯酸3-(三甲氧基甲硅烷基)丙基酯(113mmol)、6.50g苯基三甲氧基硅烷(33mmol)和2.00g甲基三甲氧基硅烷(15mmol)。向烧瓶中加入4.40g D.I.水、1.50g乙酸和14.10g异丙醇的混合物。将混合物加热到回流并在该温度保持1.5小时。然后,将混合物冷却到室温。在降低的压力下除去溶剂以提供28.86g无色液体树脂。通过凝胶渗透色谱法用聚苯乙烯作为参照测定的重均分子量为约2,920g/mol。FT-IR显示羟基的存在。
实施例4
在配备磁力搅拌器、温度计和冷凝器的100mL三颈圆底烧瓶中装入5.00g六甲基二硅氧烷、0.50g盐酸和5.00g无水乙醇。搅拌该混合物并加热到约70℃。向该混合物中滴加10.00g实施例3中制备的硅倍半氧烷树脂。滴加完成后,将温度保持在回流2小时。然后,将混合物冷却到室温并加入50mL甲苯。用饱和碳酸氢钠(50mL)洗涤有机相,接着用D.I.水洗涤(2x50mL)。干燥有机层,过滤,并且在降低的压力下除去溶剂。得到7.82g液体树脂。FT-IR显示该改性树脂中几乎没有羟基峰。
实施例5
将12g硅氧烷聚合物溶液[从Braggone Oy,Finland获得,#102227,其更充分地描述于美国专利申请60/813,266中,该申请的内容因此通过引用并入本文。该聚合物的合成过程如下:将苯基三甲氧基硅烷(1.60g,5mol%)、四乙氧基硅烷(26.81g,80mol%)和菲-9-三乙氧基硅烷(8.24g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入73.3g丙酮。在5min内向反应烧瓶中加入10.75g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于室温(RT)下搅拌该反应混合物27min并用电热套回流5小时。回流之后,用旋转蒸发器从反应混合物中除去大部分丙酮(压力350->250mbar,t(浴)=50℃)。在除去大部分丙酮之后,向烧瓶中加入72gPGMEA。添加PGMEA之后,在旋转蒸发器中进一步蒸发该反应混合物(压力45mbar,t(浴)=50℃,1小时)以进行溶剂交换。溶剂交换后,使物料溶液在120℃回流2小时。2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。]与17.33g PGMEA混合。用0.2μm膜式过滤器过滤该混合溶液。通过以1300rpm旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数折射率(n)和吸收参数(k)以及膜厚度。100nm膜厚度下折射率(n)为1.60和吸收参数(k)为0.25。
实施例6
将6.5g聚合物溶液[从Braggone Oy,Finland获得,#102267,其更充分地描述于美国专利申请60/813,266中,该申请的内容因此通过引用并入本文。该聚合物的合成过程如下:将苯基三甲氧基硅烷(4.80g,5mol%)、四乙氧基硅烷(85.47g,85mol%)和菲-9-三乙氧基硅烷(16.47g,10mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入213.48g丙酮。在4min内向反应烧瓶中加入33.48g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物26min并用电热套回流5小时。回流之后,用旋转蒸发器从反应混合物中除去大部分丙酮(压力400->200mbar,t(浴)=50℃)。在除去大部分丙酮之后,向烧瓶中加入105g PGMEA。添加PGMEA之后,在旋转蒸发器中进一步蒸发该反应混合物(压力45mbar,t(浴)=50℃,1小时)以进行溶剂交换。溶剂交换后,使物料溶液在120℃回流2小时。2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。]与9.29g PGMEA和6.21g PGME混合。用0.2μm膜式过滤器过滤该混合溶液。通过以2300rpm旋涂将过滤后的溶液施加于裸硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数n和k以及膜厚度。100nm膜厚度下折射率(n)为1.60和吸收参数(k)为0.25。
实施例7
(a)将835g聚合物溶液[从Braggone Oy,Finland获得,#102288(与102227相同组成只是更大规模的反应),其更充分地描述于美国专利申请60/813,266中,该申请的内容因此通过引用并入本文。该聚合物的合成过程如下:将苯基三甲氧基硅烷(80g,5mol%)、四乙氧基硅烷(1340.5g,80mol%)和菲-9-三乙氧基硅烷(412g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入3665.0g丙酮。在5min内向反应烧瓶中加入550.74g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于室温RT搅拌该反应混合物27min并用电热套回流5小时。回流之后,用旋转蒸发器从反应混合物中除去大部分丙酮(压力350->250mbar,t(浴)=50℃)。在除去大部分丙酮之后,向烧瓶中加入600g PGMEA。添加PGMEA之后,在旋转蒸发器中进一步蒸发该反应混合物(压力45mbar,t(浴)=50℃,1小时)以进行溶剂交换。溶剂交换后,使物料溶液在120℃回流2小时。2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。]与2715.1g PGMEA和1449.0g PGME混合。细过滤该混合溶液。将过滤后的溶液分入1L容器中并且密封。将填充的容器在温度设定为40℃的水浴中储存8天。
(b)将835g聚合物溶液(从Braggone Oy,Finland获得,#102288)与4164.1g PGMEA混合。细过滤该混合溶液。将过滤后的溶液分入1L容器中并且密封。将填充的容器在温度设定为40℃的水浴中储存8天。
在8天内用来自Rion的KS41液体粒子计数器(LPC)监控(a)和(b)中溶液的粒子数(0.2μm和0.3μm粒子)。溶液(a)的LPC计数比溶液(b)少6-10倍。
实施例8
用实施例5的溶液涂布硅基底并且在250℃烘焙90sec。烘焙过的膜具有110nm的膜厚度。在该烘焙过的膜上涂布光致抗蚀剂溶液AX2110P(出自AZ Electronic Materials,Somerville,NewJersey)。调节旋涂速度以使得光致抗蚀剂膜厚度为130nm。将涂布的晶片在100℃软烤60秒。使涂布的晶片在与ACT 12轨道相连的Nikon 306D 193nm扫描仪上曝光;NA为0.85;照度,Y-偶极,6%衰减型移相标线片。然后使曝光过的晶片在110℃曝光后烘焙60秒。该膜在0.26N TMAH水溶液中显影30秒。用SEM分析成像的光致抗蚀剂特征。观察到线宽和线距光致抗蚀剂特征为80nm L/S和75nm L/S。
实施例9
(a)将聚合物溶液[由Braggone Oy,Finland制备,#102288(与102227相同组成只是更大规模的反应),其更充分地描述于美国专利申请60/813,266中,该申请的内容因此通过引用并入本文。该聚合物的合成过程如下:将苯基三甲氧基硅烷(80g,5mol%)、四乙氧基硅烷(1340.5g,80mol%)和菲-9-三乙氧基硅烷(412g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入3665.0g丙酮。在5min内向反应烧瓶中加入550.74g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于室温RT搅拌该反应混合物27min并用电热套回流5小时。回流之后,用旋转蒸发器从反应混合物中除去大部分丙酮(压力350->250mbar,t(浴)=50℃)。在除去大部分丙酮之后,向烧瓶中加入600g PGMEA。添加PGMEA之后,在旋转蒸发器中进一步蒸发该反应混合物(压力45mbar,t(浴)=50℃,1小时)以进行溶剂交换。溶剂交换后,使物料溶液在120℃回流2小时。2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到25%固含量。]用H-NMR表征。H-NMR测量显示合成之后没有烷氧基存在,只有羟基存在。
(b)将聚合物溶液[由Braggone Oy,Finland制备,#102288(与102227相同组成只是更大规模的反应),其更充分地描述于美国专利申请60/813,266中,该申请的内容因此通过引用并入本文。该聚合物的合成过程如下:将苯基三甲氧基硅烷(80g,5mol%)、四乙氧基硅烷(1340.5g,80mol%)和菲-9-三乙氧基硅烷(412g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入3665.0g丙酮。在5min内向反应烧瓶中加入550.74g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于室温RT搅拌该反应混合物27min并用电热套回流5小时。回流之后,用旋转蒸发器从反应混合物中除去大部分丙酮(压力350->250mbar,t(浴)=50℃)。在除去大部分丙酮之后,向烧瓶中加入600g PGMEA。添加PGMEA之后,在旋转蒸发器中进一步蒸发该反应混合物(压力45mbar,t(浴)=50℃,1小时)以进行溶剂交换。溶剂交换后,使物料溶液在120℃回流2小时。2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。添加PGMEA后进一步由PGME稀释该物料溶液以产生11%最终固含量和1∶1PGMEA∶PGME溶液。]用H-NMR表征。H-NMR测量显示合成之后没有烷氧基存在,只有羟基存在。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数折射率(n)和吸收参数(k)以及膜厚度。100nm膜厚度下折射率(n)为1.61和吸收参数(k)为0.27。
(c)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(13.10g,5mol%)、四乙氧基硅烷(219.99g,80mol%)和菲-9-三乙氧基硅烷(67.58g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入300.66g PGME。在5min内向反应烧瓶中加入90.29g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行溶剂交换过程(加入203g PGME)。溶剂交换后,使物料溶液在120℃回流2小时。2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为3∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数折射率(n)和吸收参数(k)以及膜厚度。100nm膜厚度下折射率(n)为1.61和吸收参数(k)为0.24。
(d)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(26.2g,5mol%)、四乙氧基硅烷(385.28g,70mol%)和菲-9-三乙氧基硅烷(135.16g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入601.36g PGME。在5min内向反应烧瓶中加入180.58g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行溶剂交换过程(加入413g PGME)。溶剂交换后,使物料溶液在120℃回流1小时并冷却到室温。在此之后加入四乙氧基硅烷(55.05g,10mol%)并且使物料溶液在120C回流1小时。在第二个回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为2.5∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如在J.A.VUV椭圆偏振光谱仪上测定的。
(e)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(44.62g,15mol%)、四乙氧基硅烷(250.00g,80mol%)和菲-9-三乙氧基硅烷(25.62g,5mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入320.24g IPA/PGME混合物(1∶1)。在5min内向反应烧瓶中加入102.60g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从IPA/PGME混合物到PGME的溶剂交换过程(加入200g PGME)。溶剂交换后,使物料溶液在120℃回流2小时。在回流之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为4∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数折射率(n)和吸收参数(k)以及膜厚度。100nm膜厚度下折射率(n)为1.70和吸收参数(k)为0.36。
(f)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(25.05g,10mol%)、四乙氧基硅烷(150.00g,57mol%)、菲-9-三乙氧基硅烷(12.95g,3mol%)和甲基三乙氧基硅烷(67.57g,30mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入255.57g PGME。在5min内向反应烧瓶中加入81.16g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行溶剂交换过程(加入200g PGME)。溶剂交换后,使物料溶液在120℃回流2小时。在回流之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为1.5∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数折射率(n)和吸收参数(k)以及膜厚度。100nm膜厚度下折射率(n)为1.68和吸收参数(k)为0.21。
(g)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(25.05g,10mol%)、四乙氧基硅烷(150.0g,57mol%)、菲-9-三乙氧基硅烷(12.95g,3mol%)和甲基三乙氧基硅烷(45.05g,20mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入255.57g PGME。在5min内向反应烧瓶中加入81.16g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行溶剂交换过程(加入204g PGME)。溶剂交换后,使物料溶液在120℃回流1小时并冷却到室温。在此之后加入甲基三乙氧基硅烷(22.52g,10mol%)并且使物料溶液在120℃回流1小时。在第二个回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME到20%固含量并用0.1μm PTFE过滤器过滤。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为3∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数折射率(n)和吸收参数(k)以及膜厚度。100nm膜厚度下折射率(n)为1.68和吸收参数(k)为0.21。
(h)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(25.09g,10mol%)、四乙氧基硅烷(150.10g,57mol%)、菲-9-三乙氧基硅烷(12.93g,3mol%)和甲基三乙氧基硅烷(45.09g,20mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入255.57g PGME。在5min内向反应烧瓶中加入81.43g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从PGME到PGMEA的溶剂交换过程(加入250g PGMEA)。溶剂交换后,使物料溶液在120℃回流1小时并冷却到室温。在此之后加入甲基三乙氧基硅烷(22.54g,10mol%)并且使物料溶液在120℃回流1小时。在第二个回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为2∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如在J.A.VUV椭圆偏振光谱仪上测定的。
(i)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(28.43g,10mol%)、四乙氧基硅烷(230.0g,77mol%)、菲-9-三乙氧基硅烷(14.69g,3mol%)和三乙氧基硅烷(23.55g,10mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入296.67g IPA/PGME混合物(1∶1)。在5min内向反应烧瓶中加入97.25g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从IPA/PGME混合物到PGME的溶剂交换过程(加入202g PGME)。溶剂交换后,使物料溶液在120℃回流2小时。在回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为3∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒。在J.A.VUV椭圆偏振光谱仪上测定光学常数折射率(n)和吸收参数(k)以及膜厚度。100nm膜厚度下折射率(n)为1.68和吸收参数(k)为0.26。
(a)至(i)的聚合物从Braggone Oy,Finland获得。
使(a)至(i)的溶液试样在40℃老化7天。将未老化的(b)至(i)试样涂布在硅片上,在240℃烘焙60sec以形成厚度为80-130nm的膜。老化后,将(a)至(i)的试样也涂布在硅片上,在240℃烘焙60sec以形成厚度为80-130nm的膜。通过SEM评价涂布的晶片(未老化的和老化的)。老化后,试样(a)、(b)和(h)具有比其他试样更大的凹痕形成。
实施例10
(a)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(8.39g,5mol%)、四乙氧基硅烷(140.86g,80mol%)和菲-9-三乙氧基硅烷(43.27g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入192.51g PGME。在5min内向反应烧瓶中加入57.81g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从PGME到PGME的溶剂交换过程(加入230g PGME)。溶剂交换后,使物料溶液在120℃回流2小时。在2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。该溶液用PnP(丙二醇丙醚)进一步稀释以产生11%溶液(1∶1,PGME∶PnP)。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为3∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如在J.A.VUV椭圆偏振光谱仪上测定的。
(b)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(8.39g,5mol%)、四乙氧基硅烷(140.86g,80mol%)和菲-9-三乙氧基硅烷(43.27g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入192.51g PGME。在5min内向反应烧瓶中加入57.81g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从PGME到PGME的溶剂交换过程(加入230g PGME)。溶剂交换后,使物料溶液在120℃回流2小时。在2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。该溶液用NPA(乙酸正丙酯)进一步稀释以产生11%溶液(1∶1,PGME∶NPA)。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为3∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如同在J.A.VUV椭圆偏振光谱仪上测定的。
(c)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(8.39g,5mol%)、四乙氧基硅烷(140.86g,80mol%)和菲-9-三乙氧基硅烷(43.27g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入192.51g PGME。在5min内向反应烧瓶中加入57.81g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从PGME到PGME的溶剂交换过程(加入230g PGME)。溶剂交换后,使物料溶液在120℃回流2小时。在2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGME)到20%固含量并用0.1μm PTFE过滤器过滤。该溶液用NBA(乙酸正丁酯)进一步稀释以产生11%溶液(1∶1,PGME∶NBA)。]用H-NMR表征。H-NMR测量显示合成之后同时存在烷氧基和羟基。由NMR测定的羟基与烷氧基之比为3∶1。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如在J.A.VUV椭圆偏振光谱仪上测定的。
(d)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(13.10g,5mol%)、四乙氧基硅烷(220.00g,80mol%)和菲-9-三乙氧基硅烷(67.58g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入601.32g丙酮。在5min内向反应烧瓶中加入90.29g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从丙酮到PGMEA的溶剂交换过程(加入380g PGMEA)。溶剂交换后,使物料溶液在120℃回流2小时。在2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。该溶液用PnP进一步稀释以产生11%溶液(1∶1,PGME∶PnP)。]用H-NMR表征。H-NMR测量显示合成之后没有烷氧基存在,只有羟基存在。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如在J.A.VUV椭圆偏振光谱仪上测定的。
(e)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(13.10g,5mol%)、四乙氧基硅烷(220.00g,80mol%)和菲-9-三乙氧基硅烷(67.58g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入601.32g丙酮。在5min内向反应烧瓶中加入90.29g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从丙酮到PGMEA的溶剂交换过程(加入380g PGMEA)。溶剂交换后,使物料溶液在120C回流2小时。在2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。该溶液用NPA进一步稀释以产生11%溶液(1∶1,PGME∶NPA)。]用H-NMR表征。H-NMR测量显示合成之后没有烷氧基存在,只有羟基存在。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如在J.A.VUV椭圆偏振光谱仪上测定的。
(f)将聚合物溶液[由Braggone Oy,Finland制备,其用以下过程合成:将苯基三甲氧基硅烷(13.10g,5mol%)、四乙氧基硅烷(220.00g,80mol%)和菲-9-三乙氧基硅烷(67.58g,15mol%)称取到圆底烧瓶中。向该圆底烧瓶中加入601.32g丙酮。在5min内向反应烧瓶中加入90.29g水(0.01M HCl),同时用磁力搅拌器持续搅拌反应混合物。在此之后于RT搅拌该反应混合物15min并用电热套回流5小时。回流之后进行从丙酮到PGMEA的溶剂交换过程(加入380g PGMEA)。溶剂交换后,使物料溶液在120℃回流2小时。在2小时回流步骤之后,物料准备好在稀释和过滤后使用。将物料稀释(通过添加PGMEA)到20%固含量并用0.1μm PTFE过滤器过滤。该溶液用NBA进一步稀释以产生11%溶液(1∶1,PGME∶NBA)。]用H-NMR表征。H-NMR测量显示合成之后没有烷氧基存在,只有羟基存在。将聚合物溶液进一步稀释并再次用0.2μm过滤器过滤。通过旋涂将过滤后的溶液施加于硅片上并且在250℃烘焙90秒,形成厚度为100nm的膜,如在J.A.VUV椭圆偏振光谱仪上测定的。
用0.2μm过滤器过滤(a)至(f)各自的试样然后分成两份-一份在5℃下、另一份在40℃下储存7天。7天之后,将5℃和40℃储存试样的样品涂布在硅片上(在ACT-12上2500rpm,240℃烘焙/60秒)。然后评价该晶片。
将10(a)至10(e)与试样9(a)比较。
试样9(a)显示超过50%的如GPC测定的分子量增量。试样10(a)、10(b)和10(c)显示如GPC测定的分子量很少或没有增加。试样9(a)具有比试样10(a)、10(b)或10(c)更大的凹痕形成。与试样9(a)相比,试样10(d)、10(e)和10(f)具有较少数量的凹痕,但是试样10(d)、10(e)和10(f)与试样10(a)、10(b)和10(c)相比具有更大数量的凹痕。试样10(d)具有最小的分子量变化,而试样10(e)和10(f)具有最大的分子量变化。
前述的本发明说明阐明和描述了本发明。另外,该公开内容仅仅显示和描述了本发明的某些实施方案,但是如上所述,应当理解与上述教导和/或相关领域的技能或知识相称,本发明能够在各种其他组合、改进和环境下使用以及能够在如同本文表达的本发明概念的范围内改动或改进。上述实施方案进一步希望说明实施本发明已知的最佳方式,而且使得本领域技术人员能够在上述或其他的实施方案中以及在发明的特定应用或用途所要求的各种改进下利用本发明。因此,说明书并不意图将本发明限制在本文公开的形式。另外,希望所附的权利要求解释为包括可供替代的实施方案。
Claims (8)
1.一种聚合物,其包含具有至少一个Si-OH基团和至少一个Si-OR基团的硅氧烷聚合物,其中R是任选地具有反应性官能团的缩合稳定基团,其中所述硅氧烷聚合物,当被放入溶剂中时,在40℃老化一周之后由GPC测定的重均分子量增量小于或等于50%,其中所述缩合稳定基团选自醇的残基,具有式R1R2R3SiR4的化合物,其中R1、R2、R3和R4各自独立地选自氢、卤化物、C1-10烷基、C2-4烯基、C3-10环烷基、芳基、C1-10烷氧基、酰氧基、芳氧基、甲硅烷氧基、甲硅烷氧基硅烷、其中R8和R9各自选自C1-10烷基的NR8R9、其中R6和R7各自独立地选自氢、C1-10烷基或者R6和R7连同它们键合的碳原子一起形成C3-6环烷基环的ON=CR6R7,或者具有式(R12)3Si-Y-Si(R12)3的化合物,其中每个R12独立地选自C1-4烷基、C1-4烷氧基和卤素;和Y是连接基团,并且其中所述硅氧烷聚合物包含一个或多个三官能硅氧烷单元(T),
和一个或多个四官能硅氧烷单元(Q),
其中当结合的氧原子与另一硅原子键接时p的值为0.5,当结合的氧原子与硅原子之外键接时p的值为1,条件是每个T和Q单元中的至少一个p具有0.5的值;每个R10独立地选自烷基、烯基、炔基、环烷基、芳基、烷芳基、芳烷基、(烷基)丙烯酸酯、(烷基)丙烯酰氧基烷基、(烷基)丙烯酰氧基烯基、环氧官能基团和酸酐官能基团;所述硅氧烷聚合物中的T和Q单元的总数大于或等于50%,
其中,式R1R2R3SiR4或(R12)3Si-Y-Si(R12)3的所述缩合稳定基团与所述硅氧烷聚合物反应,从而Si-OH基团被Si-OR代替。
2.权利要求1的聚合物,其中Si-OH基团和Si-OR基团以1∶5-5∶1的比率存在。
3.一种制备如权利要求1或2所述的聚合物的方法,其包括如下步骤:形成具有至少一个Si-OH基团的硅氧烷聚合物;使至少一个但不是所有的所述Si-OH基团与任选地具有反应性官能团的缩合稳定基团反应,其中所述聚合物当被放入溶剂中时,在40℃老化一周之后由GPC测定的重均分子量增量小于或等于50%。
4.一种抗反射涂料组合物,其包含:
a)权利要求1或2的聚合物;和
b)溶剂。
5.权利要求4的组合物,其中对于b),所述溶剂为醇。
6.一种涂布的基底,其包括:在其上具有权利要求4或5的抗反射涂料组合物的抗反射涂膜的基底。
7.权利要求6的涂布的基底,其中固化之后,所述抗反射涂膜具有大于或等于15%的硅含量。
8.一种用于形成光致抗蚀剂浮雕图像的方法,其包括:在基底上施加权利要求4或5的组合物的层;和在权利要求4或5的组合物的所述层上施加化学放大光致抗蚀剂组合物的层。
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-
2008
- 2008-02-25 US US12/449,735 patent/US8524441B2/en not_active Expired - Fee Related
- 2008-02-25 WO PCT/IB2008/000609 patent/WO2008104881A1/en active Application Filing
- 2008-02-25 JP JP2009551283A patent/JP2010519398A/ja active Pending
- 2008-02-25 KR KR1020097017367A patent/KR101523393B1/ko not_active IP Right Cessation
- 2008-02-25 EP EP08719307A patent/EP2121808A1/en not_active Withdrawn
- 2008-02-25 CN CN2008800064415A patent/CN101622296B/zh not_active Expired - Fee Related
- 2008-02-26 TW TW97106717A patent/TWI466926B/zh not_active IP Right Cessation
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WO2008104881A1 (en) | 2008-09-04 |
US20100092895A1 (en) | 2010-04-15 |
JP2010519398A (ja) | 2010-06-03 |
TWI466926B (zh) | 2015-01-01 |
TW200844144A (en) | 2008-11-16 |
KR101523393B1 (ko) | 2015-05-27 |
JP2015038221A (ja) | 2015-02-26 |
KR20090116751A (ko) | 2009-11-11 |
EP2121808A1 (en) | 2009-11-25 |
CN101622296A (zh) | 2010-01-06 |
US8524441B2 (en) | 2013-09-03 |
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