TWI776757B - 含矽之阻劑下層膜形成用組成物、圖案形成方法及矽化合物 - Google Patents
含矽之阻劑下層膜形成用組成物、圖案形成方法及矽化合物 Download PDFInfo
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- TWI776757B TWI776757B TW110147617A TW110147617A TWI776757B TW I776757 B TWI776757 B TW I776757B TW 110147617 A TW110147617 A TW 110147617A TW 110147617 A TW110147617 A TW 110147617A TW I776757 B TWI776757 B TW I776757B
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- silicon
- underlayer film
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- AOLHFTSRLXHBNU-UHFFFAOYSA-M propanoate;tetrabutylazanium Chemical compound CCC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC AOLHFTSRLXHBNU-UHFFFAOYSA-M 0.000 description 1
- ZEKIXPPWVVMOMQ-UHFFFAOYSA-M propanoate;tetraethylazanium Chemical compound CCC([O-])=O.CC[N+](CC)(CC)CC ZEKIXPPWVVMOMQ-UHFFFAOYSA-M 0.000 description 1
- OGPGZJLEIDWRHR-UHFFFAOYSA-M propanoate;tetraethylphosphanium Chemical compound CCC([O-])=O.CC[P+](CC)(CC)CC OGPGZJLEIDWRHR-UHFFFAOYSA-M 0.000 description 1
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- PVINRUAXANHGMU-UHFFFAOYSA-M propanoate;tetraphenylphosphanium Chemical compound CCC([O-])=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PVINRUAXANHGMU-UHFFFAOYSA-M 0.000 description 1
- VTIZRIDYIWLCRE-UHFFFAOYSA-M propanoate;tetrapropylazanium Chemical compound CCC([O-])=O.CCC[N+](CCC)(CCC)CCC VTIZRIDYIWLCRE-UHFFFAOYSA-M 0.000 description 1
- KBTFBTRIFFRWNV-UHFFFAOYSA-M propanoate;trimethyl(phenyl)azanium Chemical compound CCC([O-])=O.C[N+](C)(C)C1=CC=CC=C1 KBTFBTRIFFRWNV-UHFFFAOYSA-M 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- PLZKKYRVPOUZSL-UHFFFAOYSA-N propoxybismuth Chemical group CCCO[Bi] PLZKKYRVPOUZSL-UHFFFAOYSA-N 0.000 description 1
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- VMHSRTQUBIMFJZ-UHFFFAOYSA-N propoxygermanium Chemical compound CCCO[Ge] VMHSRTQUBIMFJZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
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- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 229940080263 sodium dichloroacetate Drugs 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
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- 235000019294 sodium fumarate Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
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- 235000010334 sodium propionate Nutrition 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
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- 230000003746 surface roughness Effects 0.000 description 1
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- JJNJGSOLLMNJSD-UHFFFAOYSA-L terephthalate tetraphenylphosphanium Chemical compound C(C1=CC=C(C(=O)[O-])C=C1)(=O)[O-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 JJNJGSOLLMNJSD-UHFFFAOYSA-L 0.000 description 1
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- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
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- XSROLYDXWLCEOE-UHFFFAOYSA-M tetraethylphosphanium 2,2,2-trichloroacetate Chemical compound C(C)[P+](CC)(CC)CC.ClC(C(=O)[O-])(Cl)Cl XSROLYDXWLCEOE-UHFFFAOYSA-M 0.000 description 1
- JRQMGUGXUVNKFF-UHFFFAOYSA-M tetraethylphosphanium;acetate Chemical compound CC([O-])=O.CC[P+](CC)(CC)CC JRQMGUGXUVNKFF-UHFFFAOYSA-M 0.000 description 1
- ZZSILJPVLCLAMM-UHFFFAOYSA-M tetraethylphosphanium;benzoate Chemical compound CC[P+](CC)(CC)CC.[O-]C(=O)C1=CC=CC=C1 ZZSILJPVLCLAMM-UHFFFAOYSA-M 0.000 description 1
- LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 description 1
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- YUKNWAMYDSSWLX-UHFFFAOYSA-M tetraethylphosphanium;formate Chemical compound [O-]C=O.CC[P+](CC)(CC)CC YUKNWAMYDSSWLX-UHFFFAOYSA-M 0.000 description 1
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- IYPJDYWPLUISDW-UHFFFAOYSA-N tetraethylphosphanium;nitrate Chemical compound [O-][N+]([O-])=O.CC[P+](CC)(CC)CC IYPJDYWPLUISDW-UHFFFAOYSA-N 0.000 description 1
- BPYSJOQJBAZTDB-UHFFFAOYSA-M tetraethylphosphanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC[P+](CC)(CC)CC BPYSJOQJBAZTDB-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- KVIIKBGGNBBOEI-UHFFFAOYSA-M tetramethylazanium;2,2,2-trichloroacetate Chemical compound C[N+](C)(C)C.[O-]C(=O)C(Cl)(Cl)Cl KVIIKBGGNBBOEI-UHFFFAOYSA-M 0.000 description 1
- LROATHSBUUYETB-UHFFFAOYSA-M tetramethylazanium;2,2,2-trifluoroacetate Chemical compound C[N+](C)(C)C.[O-]C(=O)C(F)(F)F LROATHSBUUYETB-UHFFFAOYSA-M 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
- IEVVGBFMAHJELO-UHFFFAOYSA-M tetramethylazanium;benzoate Chemical compound C[N+](C)(C)C.[O-]C(=O)C1=CC=CC=C1 IEVVGBFMAHJELO-UHFFFAOYSA-M 0.000 description 1
- WJZPIORVERXPPR-UHFFFAOYSA-L tetramethylazanium;carbonate Chemical compound [O-]C([O-])=O.C[N+](C)(C)C.C[N+](C)(C)C WJZPIORVERXPPR-UHFFFAOYSA-L 0.000 description 1
- WWIYWFVQZQOECA-UHFFFAOYSA-M tetramethylazanium;formate Chemical compound [O-]C=O.C[N+](C)(C)C WWIYWFVQZQOECA-UHFFFAOYSA-M 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- MANNXDXMUHZSRP-UHFFFAOYSA-M tetramethylazanium;trifluoromethanesulfonate Chemical compound C[N+](C)(C)C.[O-]S(=O)(=O)C(F)(F)F MANNXDXMUHZSRP-UHFFFAOYSA-M 0.000 description 1
- UAMLLALJRFFHBA-UHFFFAOYSA-M tetraphenylphosphanium 2,2,2-trichloroacetate Chemical compound ClC(C(=O)[O-])(Cl)Cl.C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 UAMLLALJRFFHBA-UHFFFAOYSA-M 0.000 description 1
- FDPJPTOZZRISMD-UHFFFAOYSA-M tetraphenylphosphanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FDPJPTOZZRISMD-UHFFFAOYSA-M 0.000 description 1
- HLNHDVOODYDVRZ-UHFFFAOYSA-M tetraphenylphosphanium;acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HLNHDVOODYDVRZ-UHFFFAOYSA-M 0.000 description 1
- FOUUISAQGPLIMM-UHFFFAOYSA-M tetraphenylphosphanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FOUUISAQGPLIMM-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- MRFFLWSQLSQAJK-UHFFFAOYSA-L tetraphenylphosphanium;carbonate Chemical compound [O-]C([O-])=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MRFFLWSQLSQAJK-UHFFFAOYSA-L 0.000 description 1
- VLDHXZBAXRDKQN-UHFFFAOYSA-M tetraphenylphosphanium;formate Chemical compound [O-]C=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VLDHXZBAXRDKQN-UHFFFAOYSA-M 0.000 description 1
- XVHQFGPOVXTXPD-UHFFFAOYSA-M tetraphenylphosphanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XVHQFGPOVXTXPD-UHFFFAOYSA-M 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- DBUVZKQSYMGPFQ-UHFFFAOYSA-N tetraphenylphosphanium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DBUVZKQSYMGPFQ-UHFFFAOYSA-N 0.000 description 1
- HSPFYCYQLYXTDL-UHFFFAOYSA-M tetraphenylphosphanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HSPFYCYQLYXTDL-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-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
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- BQBCSZFEFRYJPX-UHFFFAOYSA-M tetrapropylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CCC[N+](CCC)(CCC)CCC BQBCSZFEFRYJPX-UHFFFAOYSA-M 0.000 description 1
- QOHLYFXRPYZSJX-UHFFFAOYSA-M tetrapropylazanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCC[N+](CCC)(CCC)CCC QOHLYFXRPYZSJX-UHFFFAOYSA-M 0.000 description 1
- DKBLJGBNSOBLAO-UHFFFAOYSA-L tetrapropylazanium;carbonate Chemical compound [O-]C([O-])=O.CCC[N+](CCC)(CCC)CCC.CCC[N+](CCC)(CCC)CCC DKBLJGBNSOBLAO-UHFFFAOYSA-L 0.000 description 1
- FBEVECUEMUUFKM-UHFFFAOYSA-M tetrapropylazanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCC FBEVECUEMUUFKM-UHFFFAOYSA-M 0.000 description 1
- LENBOWGJEQXFCI-UHFFFAOYSA-M tetrapropylazanium;formate Chemical compound [O-]C=O.CCC[N+](CCC)(CCC)CCC LENBOWGJEQXFCI-UHFFFAOYSA-M 0.000 description 1
- GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 1
- HZPNJVXVIFRTRF-UHFFFAOYSA-N tetrapropylazanium;nitrate Chemical compound [O-][N+]([O-])=O.CCC[N+](CCC)(CCC)CCC HZPNJVXVIFRTRF-UHFFFAOYSA-N 0.000 description 1
- IGVWFPZXBUTUCG-UHFFFAOYSA-M tetrapropylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCC[N+](CCC)(CCC)CCC IGVWFPZXBUTUCG-UHFFFAOYSA-M 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- YGBFTDQFAKDXBZ-UHFFFAOYSA-N tributyl stiborite Chemical compound [Sb+3].CCCC[O-].CCCC[O-].CCCC[O-] YGBFTDQFAKDXBZ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- IIAAHORGJDRQNJ-UHFFFAOYSA-N triethyl(hexan-2-yl)azanium Chemical compound CCCCC(C)[N+](CC)(CC)CC IIAAHORGJDRQNJ-UHFFFAOYSA-N 0.000 description 1
- COZJAFRPCBOENV-UHFFFAOYSA-M triethyl(phenyl)azanium 2,2,2-trifluoroacetate Chemical compound FC(C(=O)[O-])(F)F.C(C)[N+](C1=CC=CC=C1)(CC)CC COZJAFRPCBOENV-UHFFFAOYSA-M 0.000 description 1
- DVNBMDVBOOHQPC-UHFFFAOYSA-M triethyl(phenyl)azanium formate Chemical compound C(=O)[O-].C(C)[N+](C1=CC=CC=C1)(CC)CC DVNBMDVBOOHQPC-UHFFFAOYSA-M 0.000 description 1
- IGOKCMJMCZRQOZ-UHFFFAOYSA-M triethyl(phenyl)azanium trifluoromethanesulfonate Chemical compound FC(S(=O)(=O)[O-])(F)F.C(C)[N+](C1=CC=CC=C1)(CC)CC IGOKCMJMCZRQOZ-UHFFFAOYSA-M 0.000 description 1
- ZXRRCQKMZOSCNS-UHFFFAOYSA-M triethyl(phenyl)azanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CC[N+](CC)(CC)C1=CC=CC=C1 ZXRRCQKMZOSCNS-UHFFFAOYSA-M 0.000 description 1
- HMJWAKCBJWAMPL-UHFFFAOYSA-M triethyl(phenyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)C1=CC=CC=C1 HMJWAKCBJWAMPL-UHFFFAOYSA-M 0.000 description 1
- ICTMDIORIDZWQN-UHFFFAOYSA-M triethyl(phenyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)C1=CC=CC=C1 ICTMDIORIDZWQN-UHFFFAOYSA-M 0.000 description 1
- WMSWXWGJYOIACA-UHFFFAOYSA-M triethyl(phenyl)azanium;iodide Chemical compound [I-].CC[N+](CC)(CC)C1=CC=CC=C1 WMSWXWGJYOIACA-UHFFFAOYSA-M 0.000 description 1
- DXQQIHXTRQPIFI-UHFFFAOYSA-N triethyl(phenyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.CC[N+](CC)(CC)C1=CC=CC=C1 DXQQIHXTRQPIFI-UHFFFAOYSA-N 0.000 description 1
- REIQMNHINXXPQU-UHFFFAOYSA-M trifluoromethanesulfonate trimethyl(phenyl)azanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C[N+](C)(C)C1=CC=CC=C1 REIQMNHINXXPQU-UHFFFAOYSA-M 0.000 description 1
- QFCVQKSWGFVMTB-UHFFFAOYSA-N trihexoxyalumane Chemical compound [Al+3].CCCCCC[O-].CCCCCC[O-].CCCCCC[O-] QFCVQKSWGFVMTB-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- DLSULYIQRAZOPW-UHFFFAOYSA-M trimethyl(phenyl)azanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C1=CC=CC=C1 DLSULYIQRAZOPW-UHFFFAOYSA-M 0.000 description 1
- SHPSATWFJSHRAL-UHFFFAOYSA-M trimethyl(phenyl)azanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.C[N+](C)(C)C1=CC=CC=C1 SHPSATWFJSHRAL-UHFFFAOYSA-M 0.000 description 1
- GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
- PHHAYLUYXZACAB-UHFFFAOYSA-L trimethyl(phenyl)azanium;carbonate Chemical compound [O-]C([O-])=O.C[N+](C)(C)C1=CC=CC=C1.C[N+](C)(C)C1=CC=CC=C1 PHHAYLUYXZACAB-UHFFFAOYSA-L 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- KKLAORVGAKUOPZ-UHFFFAOYSA-M trimethyl(phenyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=CC=C1 KKLAORVGAKUOPZ-UHFFFAOYSA-M 0.000 description 1
- DTEAMGZRDRBFPI-UHFFFAOYSA-N trimethyl(phenyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.C[N+](C)(C)C1=CC=CC=C1 DTEAMGZRDRBFPI-UHFFFAOYSA-N 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- LIJDDOXRYWAXQG-UHFFFAOYSA-N tripentoxyalumane Chemical compound CCCCCO[Al](OCCCCC)OCCCCC LIJDDOXRYWAXQG-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- ZJZKUISELYXHDV-UHFFFAOYSA-K triphenyl stiborite Chemical compound [Sb+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZJZKUISELYXHDV-UHFFFAOYSA-K 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- YWIUPWSLDVUCDT-UHFFFAOYSA-N tris(1-methoxyethoxy)alumane Chemical compound [Al+3].COC(C)[O-].COC(C)[O-].COC(C)[O-] YWIUPWSLDVUCDT-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical group [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F7/1804—Compounds having Si-O-C linkages
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
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- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
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- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/17—Amines; Quaternary ammonium compounds
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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- 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
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Abstract
本發明之課題係提供可形成無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性,而且對於如EUV曝光之更微細的圖案亦具良好之密接性的阻劑下層膜的含矽之阻劑下層膜形成用組成物、圖案形成方法及矽化合物。一種含矽之阻劑下層膜形成用組成物,其特徵為:含有1種以上之下列通式(1)表示之矽化合物(A-1)的水解物或水解縮合物中之任一者、或其兩者。
Description
本發明關於含矽之阻劑下層膜形成用組成物、圖案形成方法及矽化合物。
伴隨大型積體電路(LSI)的高積體化與高速化,圖案尺寸的微細化正急速進展。微影技術,伴隨該微細化,藉由光源之短波長化及適當選擇與其對應的阻劑組成物,已達成微細圖案的形成。
作為近年備受矚目的微細化技術之一,可列舉利用第1次曝光與顯影形成第1圖案,再利用第2次曝光恰好在第1次圖案中間形成圖案的雙重圖案化製程(非專利文獻1)。就雙重圖案化的方法已有人提出許多種製程。例如可列舉:(1)利用第1次曝光與顯影形成線與間距為1:3之間隔的光阻劑圖案,再利用乾蝕刻對下層的硬遮罩進行加工,於其上鋪設另一層硬遮罩,於以第1次曝光獲得之間距部分利用光阻劑膜的曝光與顯影形成第2線圖案,再利用乾蝕刻對硬遮罩進行加工,形成節距為最初圖案之節距的一半的線與間距圖案的方法。又,可列舉:(2)利用第1次曝光與顯影形成間距與線為1:3之間隔的光阻劑圖案,再利用乾蝕刻對下層的硬遮罩進行加工,於其上塗布光阻劑膜,再於殘留有硬遮罩的部分利用第2次曝光形成圖案,將其作為遮罩並利用乾蝕刻對硬遮罩進行加工的方法。均係利用2次的乾蝕刻對硬遮罩進行加工的方法。
另外,為了只進行1次乾蝕刻,有在第1次曝光使用負型阻劑材料,在第2次曝光使用正型阻劑材料的方法。又,也有在第1次曝光使用正型阻劑材料,在第2次曝光使用溶解於不會溶解正型阻劑材料之碳為4個以上之高級醇的負型阻劑材料的方法。
作為其他方法,有人提出將利用第1次曝光與顯影形成之第1圖案,以反應性金屬化合物進行處理,使圖案不溶化後,在第1圖案的圖案間重新利用曝光、顯影形成第2圖案的方法(專利文獻1)。
另一方面,近年由於ArF浸潤式微影、EUV微影等的出現,逐漸可形成更微細的圖案,但另一方面,超微細圖案由於接地面積小,故極易崩塌,圖案崩塌的抑制係非常大的課題。因此,抑制圖案崩塌的效果高的含矽之阻劑下層膜的開發成為當務之急。
如此,為了形成更微細的圖案而探討了各種手法,但其中共通的課題係防止所形成之微細圖案的崩塌。為了達成此點,尋求進一步改善上層阻劑圖案與阻劑下層膜之間的密接性。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開2008-033174號公報
[非專利文獻]
[非專利文獻1]Proc.SPIE Vol.5754 p1508(2005)
[發明所欲解決之課題]
本發明係為了解決上述問題而成,旨在提供一種含矽之阻劑下層膜形成用組成物,可形成無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性,而且對於如EUV曝光之更微細的圖案亦具良好之密接性的阻劑下層膜;並旨在提供圖案形成方法及矽化合物。
[解決課題之手段]
為了解決上述課題,本發明提供一種含矽之阻劑下層膜形成用組成物,含有1種以上之下列通式(1)表示之矽化合物(A-1)的水解物或水解縮合物中之任一者、或其兩者。
[化1]
上述通式(1)中,R
1為氫原子或碳數1~30之1價有機基,R
2為烷氧基、醯氧基、或鹵素原子。n1為0、1或2。R
3、R
4各自獨立地為氫原子,或為亦可含有氮原子、氧原子、硫原子、鹵素原子、或矽原子的碳數1~6之有機基,R
3與R
4亦可鍵結並形成環。R
5為碳數1~30之1價有機基。n2為0、1、2或3。Y為單鍵或亦可含有矽原子的碳數1~6之2價有機基。Z為碳原子或矽原子。
若為如此之含矽之阻劑下層膜形成用組成物,可形成無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性,而且對於如EUV曝光之更微細的圖案亦具良好之密接性的阻劑下層膜。
又,本發明提供前述含矽之阻劑下層膜形成用組成物含有前述矽化合物(A-1)與1種以上之下列通式(2)表示之矽化合物(A-2)之混合物的水解物或水解縮合物中之任一者、或其兩者的含矽之阻劑下層膜形成用組成物。
[化2]
上述通式(2)中,R
6為氫原子,或為亦可含有碳-氧單鍵、碳-氧雙鍵、矽-矽鍵、碳-氮鍵、碳-硫鍵、會因酸分解之保護基、碘原子、磷原子或氟原子的碳數1~30之1價有機基,R
7為烷氧基、醯氧基、或鹵素原子。m為0、1、2或3。
若為如此之含矽之阻劑下層膜形成用組成物,可形成無論負顯影、正顯影,對於任何阻劑圖案均具更良好之密接性,而且對於如EUV曝光之更微細的圖案亦具更良好之密接性的阻劑下層膜。
又,本發明提供更含有交聯觸媒的含矽之阻劑下層膜形成用組成物。
若為如此之含矽之阻劑下層膜形成用組成物,可形成無論負顯影、正顯影,對於任何阻劑圖案均具更良好之密接性,而且對於如EUV曝光之更微細的圖案亦具更良好之密接性的阻劑下層膜。
此時,前述交聯觸媒宜為鋶鹽、錪鹽、鏻鹽、銨鹽、鹼金屬鹽、或具有鋶鹽、錪鹽、鏻鹽、及銨鹽中之任一者作為結構之一部分的聚矽氧烷較佳。
本發明之含矽之阻劑下層膜形成用組成物可使用如此之交聯觸媒。
又,宜更含有1種以上之下列通式(P-0)表示之化合物。
[化3]
上述式中,R
300為經1個以上之氟原子取代的2價有機基,R
301及R
302各自獨立地表示亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之1價烴基。R
303表示亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之2價烴基。又,R
301與R
302、或R
301與R
303亦可彼此鍵結並與式中之硫原子一起形成環。L
304表示單鍵、或亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之2價烴基。
含有上述通式(P-0)表示之化合物時,藉由與本發明之含矽之阻劑下層膜形成用組成物組合,可獲得能於保持上層阻劑之LWR之同時貢獻於剖面形狀之矩形化的阻劑下層膜。
此時,前述通式(P-0)表示之化合物宜為下列通式(P-1)表示之化合物。
[化4]
式中,X
305、X
306各自獨立地表示氫原子、氟原子、三氟甲基中之任一者,但不全部為氫原子。n
307表示1~4之整數。R
301、R
302、R
303及L
304係與前述同樣。
上述通式(P-0)表示之化合物為上述通式(P-1)表示之化合物時,會更充分地發揮本發明之效果。
又,本發明提供一種圖案形成方法,係於被加工體上使用塗布型有機下層膜材料來形成有機下層膜,於該有機下層膜之上使用上述含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜,於該含矽之阻劑下層膜上使用光阻劑組成物來形成光阻劑膜,將前述光阻劑膜進行曝光、顯影而形成阻劑圖案,將該形成有圖案之光阻劑膜作為遮罩,利用乾蝕刻對前述含矽之阻劑下層膜進行圖案轉印,將該轉印有圖案之含矽之阻劑下層膜作為遮罩,利用乾蝕刻對前述有機下層膜進行圖案轉印,進一步,將該轉印有圖案之有機下層膜作為遮罩,利用乾蝕刻將圖案轉印至前述被加工體。
若為如此之圖案形成方法,於在含矽之阻劑下層膜之下形成塗布型有機下層膜的圖案形成方法中,無論負顯影、正顯影,均可抑制圖案崩塌的發生並形成微細圖案。
又,本發明提供一種圖案形成方法,係於被加工體上利用CVD法形成以碳作為主成分之硬遮罩,於該CVD硬遮罩之上使用上述含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜,於該含矽之阻劑下層膜上使用光阻劑組成物來形成光阻劑膜,將前述光阻劑膜進行曝光、顯影而形成阻劑圖案,將該形成有圖案之光阻劑膜作為遮罩,利用乾蝕刻對前述含矽之阻劑下層膜進行圖案轉印,將該轉印有圖案之含矽之阻劑下層膜作為遮罩,利用乾蝕刻對前述CVD硬遮罩進行圖案轉印,進一步,將該轉印有圖案之CVD硬遮罩作為遮罩,利用乾蝕刻將圖案轉印至前述被加工體。
若為如此之圖案形成方法,於在含矽之阻劑下層膜之下形成CVD硬遮罩的圖案形成方法中,無論負顯影、正顯影,均可抑制圖案崩塌的發生並形成微細圖案。
又,前述阻劑圖案的形成,宜利用使用了波長為10nm以上300nm以下之光的微影、電子束所為之直接描繪、奈米壓印、或它們的組合來形成阻劑圖案較佳。
又,前述阻劑圖案的形成,宜利用鹼顯影或有機溶劑顯影對阻劑圖案進行顯影。
使用本發明之含矽之阻劑下層膜形成用組成物的圖案形成方法中,可理想地使用如此之阻劑圖案的形成手段及顯影手段。
此時,前述被加工體宜為半導體裝置基板、或於該半導體裝置基板上形成有金屬膜、合金膜、金屬碳化膜、金屬氧化膜、金屬氮化膜、金屬氧化碳化膜或金屬氧化氮化膜中之任一種膜者較佳。
若為使用本發明之含矽之阻劑下層膜形成用組成物的圖案形成方法,可對如上述之被加工體進行加工並形成圖案。
又,構成前述被加工體之金屬宜為矽、鎵、鈦、鎢、鉿、鋯、鉻、鍺、銅、銀、金、銦、砷、鈀、鉭、銥、鋁、鐵、鉬、鈷或它們的合金。
使用本發明之含矽之阻劑下層膜形成用組成物的圖案形成方法的被加工體,宜為如上述之金屬。
又,本發明提供一種矽化合物,係以下列通式(1)表示。
[化5]
上述通式(1)中,R
1為氫原子或碳數1~30之1價有機基,R
2為烷氧基、醯氧基、或鹵素原子。n1為0、1或2。R
3、R
4各自獨立地為氫原子,或為亦可含有氮原子、氧原子、硫原子、鹵素原子、或矽原子的碳數1~6之有機基,R
3與R
4亦可鍵結並形成環。R
5為碳數1~30之1價有機基。n2為0、1、2或3。Y為單鍵或亦可含有矽原子的碳數1~6之2價有機基。Z為碳原子或矽原子。
若為如此之矽化合物,會成為可提供能形成無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性,而且對於如EUV曝光之更微細的圖案亦具良好之密接性的阻劑下層膜的含矽之阻劑下層膜形成用組成物的矽化合物。
[發明之效果]
如上述,若使用本發明之含矽之阻劑下層膜形成用組成物形成阻劑下層膜,無論鹼顯影(正顯影)、有機溶劑顯影(負顯影)中,阻劑下層膜對於阻劑圖案之密接性均良好,故不會發生圖案崩塌,可形成表面粗糙度亦良好的圖案。另外,該阻劑下層膜對於如EUV曝光之更微細的圖案,亦可抑制圖案崩塌。又,據認為在實際的半導體裝置製造步驟中,並非所有的圖案形成步驟都被置換成負顯影,只有極少部分的超微細步驟被置換,以往的正顯影步驟仍保留原樣。此時,負型專用阻劑下層膜、正型專用下層膜係專用化的話,裝置上及組成物的品質管理上均變得繁雜。與此相對,若為在正型、負型之兩種步驟中均可適用,且亦可適用於更微細的EUV曝光的本發明之含矽之阻劑下層膜形成用組成物,裝置上與品質管理上均可合理地運用。
如上述,尋求開發可形成無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性,而且對於如EUV曝光之更微細的圖案亦具良好之密接性的阻劑下層膜的含矽之阻劑下層膜形成用組成物。
作為習知技術,已知有為了防止ArF曝光之負顯影圖案中之圖案崩塌,而使下層膜之接觸角匹配上層阻劑圖案的接觸角的方法(日本特開2012-237975號公報等)。但是,在圖案線寬更微細的EUV曝光中,利用該方法無法形成能適用於先進製程的圖案線寬。於是,本案發明人等進行努力研究的結果,發現藉由導入可於阻劑下層膜與上層之阻劑之間形成化學鍵結的官能基,對於利用EUV曝光形成之負顯影圖案抑或正顯影圖案之任何微細圖案,均可達成防止崩塌,而完成了本發明。又,藉由導入兼具上述可因EUV曝光而在阻劑下層膜與上層之阻劑之間形成化學鍵結的官能基及如習知技術般使接觸角匹配上層之阻劑圖案之接觸角的官能基的次結構,在ArF曝光中亦可達成防止崩塌的效果。
亦即,本發明係一種含矽之阻劑下層膜形成用組成物,其特徵為:含有1種以上之下列通式(1)表示之矽化合物(A-1)的水解物或水解縮合物中之任一者、或其兩者。
[化6]
上述通式(1)中,R
1為氫原子或碳數1~30之1價有機基,R
2為烷氧基、醯氧基、或鹵素原子。n1為0、1或2。R
3、R
4各自獨立地為氫原子,或為亦可含有氮原子、氧原子、硫原子、鹵素原子、或矽原子的碳數1~6之有機基,R
3與R
4亦可鍵結並形成環。R
5為碳數1~30之1價有機基。n2為0、1、2或3。Y為單鍵或亦可含有矽原子的碳數1~6之2價有機基。Z為碳原子或矽原子。
以下,針對本發明詳細地說明,但本發明不限定於該等。此外,本說明書中,Me表示甲基,Et表示乙基,Ac表示乙醯基,Cl表示氯原子。
<含矽之阻劑下層膜形成用組成物>
本發明之含矽之阻劑下層膜形成用組成物,含有下列通式(1)表示之矽化合物(A-1)的水解物或水解縮合物中之任一者、或其兩者。又,本發明之含矽之阻劑下層膜形成用組成物,其特徵為:係藉由將下列通式(1)表示之矽化合物(A-1)進行水解或水解縮合、或進行其兩者而獲得。本發明之含矽之阻劑下層膜形成用組成物,通式(1)表示之矽化合物(A-1)之苄基位因熱、酸、或其兩者的作用而與上層之阻劑圖案反應並形成鍵結,藉此成為無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性者。
[化7]
以下,針對通式(1)表示之矽化合物(A-1)、及含有其水解物或水解縮合物中之任一者、或其兩者的含矽之阻劑下層膜形成用組成物、及該組成物中含有的熱硬化性含矽材料進行詳細地說明。
[熱硬化性含矽材料]
本發明中,熱硬化性含矽材料係藉由將通式(1)表示之矽化合物(A-1)進行水解或水解縮合、或進行其兩者而獲得。通式(1)表示之矽化合物(A-1),就其特徵性結構而言,係藉由形成環狀結構來保護酚系羥基與苯甲醇。本發明中,據認為因熱、酸、或其兩者的作用,如以下所示般在曝光部、或未曝光部,於通式(1)表示之矽化合物(A-1)之苄基位與阻劑圖案之間形成鍵結。據認為例如在未曝光部,因熱、酸、或其兩者的作用,通式(1)表示之矽化合物(A-1)之苄基位與阻劑圖案中之芳香環(Ar)直接反應,並形成鍵結(參照下列方案之上段)。據認為在曝光部,因熱、酸、或其兩者的作用,含Z之保護基脫離後,產生反應活性物種(芳基陽離子),反應活性物種與阻劑圖案中之芳香環(Ar)反應,並形成鍵結(參照下列方案之下段)。如此,於通式(1)表示之矽化合物(A-1)之苄基位與阻劑圖案之間形成鍵結,在阻劑下層膜與上層之阻劑圖案之間形成鍵結,故就結果而言,可獲得對於圖案之密接性改善,圖案形狀亦優異的膜。
此外,此時與通式(1)表示之矽化合物(A-1)之苄基位反應的對象,亦可列舉阻劑圖案中之羥基、羧基等。
另外,作為此時與通式(1)表示之矽化合物(A-1)之苄基位反應的對象,也可列舉容易進行芳香族親電子取代反應的化合物,例如具有電子供給性取代基的化合物等。具體而言,可例示苯酚-甲醯胺樹脂、多羥基苯乙烯樹脂等具有酚性羥基之樹脂。
ArF曝光時,在未曝光部,上述通式(1)表示之矽化合物(A-1)之環狀保護基不會脫保護而維持有機性,故與阻劑圖案之親和性高,在正顯影中可獲得圖案形狀優異的膜。
ArF曝光時,在曝光部,上述通式(1)表示之矽化合物(A-1)之環狀保護基可藉由熱、酸、或其兩者的作用而輕易地脫保護,生成酚系羥基與苯甲醇,接觸角降低,故在負顯影中亦可獲得對於圖案之密接性改善,圖案形狀優異的膜。
通式(1)中,R
1為氫原子或碳數1~30之1價有機基。碳數1~30之1價有機基之較佳例可列舉:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、乙烯基、丙烯基、環丙基、環丁基、環戊基、環己基、環庚基、降莰基、環氧丙氧基丙基、胺基丙基、氯丙基、苯基、甲苯基、羥基苯基、甲氧基苄基、乙氧基苯基、丁氧基苯基、萘基、及羥基萘基等。
通式(1)中,R
2為烷氧基、醯氧基、或鹵素原子。此外,烷氧基宜為甲氧基、乙氧基等。醯氧基宜為乙醯氧基等。鹵素原子宜為氟、氯、溴等。
通式(1)中,R
3、R
4各自獨立地為氫原子,或為亦可含有氮原子、氧原子、硫原子、鹵素原子、或矽原子的碳數1~6之有機基,R
3與R
4亦可鍵結並形成環。此外,R
3、R
4宜為氫原子、甲基、乙基、丙基、異丙基、環戊基、環己基、苯基等。
通式(1)中,R
5為碳數1~30之1價有機基。碳數1~30之1價有機基之較佳例可列舉:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、乙烯基、丙烯基、環丙基、環丁基、環戊基、環己基、環庚基、降莰基、環氧丙氧基丙基、胺基丙基、氯丙基、苯基、甲苯基、羥基苯基、甲氧基苄基、乙氧基苯基、丁氧基苯基、萘基、及羥基萘基等。
通式(1)中,Y為單鍵或亦可含有矽原子的碳數1~6之2價有機基。碳數1~6之2價有機基之較佳例可列舉:亞甲基、伸乙基、伸丙基、伸丁基、伸戊基、伸己基、及具有分支或環結構之該等基的結構異構體等。又,亦可含有選自醚性氧原子、羰基、及羰基氧基中之1種以上,含有時,只要是不與式中之矽原子(Si)直接鍵結的位置,則可於任何部位含有。
通式(1)中,Z為碳原子或矽原子。
矽化合物(A-1)可如後述藉由將二醇體利用具有R
3R
4Z基(Z為C或Si)之化合物進行保護而獲得。矽化合物(A-1)如後述可先利用R
3R
4Z基(保護基)將水楊醇衍生物予以保護,再進行官能基轉換,亦可於最終階段導入保護基。水楊醇衍生物可使用市售品,亦可利用常法合成。
通式(1)中Z為碳原子的矽化合物之合成方法並無特別限定,例如可列舉如下方法:於N
2環境下,將5-溴-2-羥基苯甲醇、2,2-二甲氧基丙烷、丙酮混合,加入對甲苯磺酸一水合物,使其反應而合成c1,使Mg作用於c1,製備格氏試劑後,使其與四甲氧基矽烷反應,而合成c2。
[化12]
通式(1)中,Z為矽原子的矽化合物之合成方法並無特別限定,例如可列舉:如下式使5-乙烯基-2-羥基-苯甲醇與二甲基二氯矽烷反應而合成a1,使a1在鉑觸媒下與三甲氧基矽烷反應,而合成a2的方法(A法);使5-溴-2-羥基苯甲醇與二甲基二氯矽烷反應而合成b1,使Mg作用於b1,製備格氏試劑後,使其與四甲氧基矽烷反應,而合成b2的方法(B法)。
[化13]
[化14]
本發明可提供一種含矽之阻劑下層膜形成用組成物,含有前述矽化合物(A-1)與1種以上之下列通式(2)表示之矽化合物(A-2)之混合物的水解物或水解縮合物中之任一者、或其兩者。又,本發明可提供一種含矽之阻劑下層膜形成用組成物,其特徵為:藉由將前述矽化合物(A-1)與1種以上之下列通式(2)表示之矽化合物(A-2)之混合物進行水解或水解縮合、或進行其兩者而獲得。
[化29]
通式(2)中,R
6為氫原子,或為亦可含有碳-氧單鍵、碳-氧雙鍵、矽-矽鍵、碳-氮鍵、碳-硫鍵、會因酸分解之保護基、碘原子、磷原子或氟原子的碳數1~30之1價有機基。
通式(2)中,R
7為烷氧基、醯氧基、或鹵素原子。此外,本發明中,熱硬化性含矽材料所使用的水解性單體使用烷氧基矽烷更佳。
通式(2)中,m為0、1、2或3。矽化合物(A-2),具體而言,係於矽上具有上述R
6與作為水解性基R
7的1個、2個、3個或4個氯、溴、碘、乙醯氧基、甲氧基、乙氧基、丙氧基或丁氧基等者,另外,亦可於矽上具有氫原子或上述碳數1~30之1價有機基作為R
6。
通式(2)表示之矽化合物(A-2)之示例可列舉如下。
可例示:四甲氧基矽烷、四乙氧基矽烷、四丙氧基矽烷、四異丙氧基矽烷、三甲氧基矽烷、三乙氧基矽烷、三丙氧基矽烷、三異丙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三丙氧基矽烷、甲基三異丙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙基三丙氧基矽烷、乙基三異丙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三丙氧基矽烷、乙烯基三異丙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丙基三丙氧基矽烷、丙基三異丙氧基矽烷、異丙基三甲氧基矽烷、異丙基三乙氧基矽烷、異丙基三丙氧基矽烷、異丙基三異丙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、丁基三丙氧基矽烷、丁基三異丙氧基矽烷、異丁基三甲氧基矽烷、異丁基三乙氧基矽烷、第二丁基三甲氧基矽烷、第二丁基三乙氧基矽烷、第二丁基三丙氧基矽烷、第二丁基三異丙氧基矽烷、第三丁基三甲氧基矽烷、第三丁基三乙氧基矽烷、第三丁基三丙氧基矽烷、第三丁基三異丙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、環丙基三甲氧基矽烷、環丙基三乙氧基矽烷、環丙基三丙氧基矽烷、環丙基三異丙氧基矽烷、環丁基三甲氧基矽烷、環丁基三乙氧基矽烷、環丁基三丙氧基矽烷、環丁基三異丙氧基矽烷、環戊基三甲氧基矽烷、環戊基三乙氧基矽烷、環戊基三丙氧基矽烷、環戊基三異丙氧基矽烷、環己基三甲氧基矽烷、環己基三乙氧基矽烷、環己基三丙氧基矽烷、環己基三異丙氧基矽烷、環己烯基三甲氧基矽烷、環己烯基三乙氧基矽烷、環己烯基三丙氧基矽烷、環己烯基三異丙氧基矽烷、環己烯基乙基三甲氧基矽烷、環己烯基乙基三乙氧基矽烷、環己烯基乙基三丙氧基矽烷、環己烯基乙基三異丙氧基矽烷、環辛基三甲氧基矽烷、環辛基三乙氧基矽烷、環辛基三丙氧基矽烷、環辛基三異丙氧基矽烷、環戊二烯基丙基三甲氧基矽烷、環戊二烯基丙基三乙氧基矽烷、環戊二烯基丙基三丙氧基矽烷、環戊二烯基丙基三異丙氧基矽烷、雙環庚烯基三甲氧基矽烷、雙環庚烯基三乙氧基矽烷、雙環庚烯基三丙氧基矽烷、雙環庚烯基三異丙氧基矽烷、雙環庚基三甲氧基矽烷、雙環庚基三乙氧基矽烷、雙環庚基三丙氧基矽烷、雙環庚基三異丙氧基矽烷、金剛烷基三甲氧基矽烷、金剛烷基三乙氧基矽烷、金剛烷基三丙氧基矽烷、金剛烷基三異丙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、苯基三丙氧基矽烷、苯基三異丙氧基矽烷、苄基三甲氧基矽烷、苄基三乙氧基矽烷、苄基三丙氧基矽烷、苄基三異丙氧基矽烷、甲氧基苄基三甲氧基矽烷、甲氧基苄基三乙氧基矽烷、甲氧基苄基三丙氧基矽烷、甲氧基苄基三異丙氧基矽烷、甲苯基三甲氧基矽烷、甲苯基三乙氧基矽烷、甲苯基三丙氧基矽烷、甲苯基三異丙氧基矽烷、苯乙基三甲氧基矽烷、苯乙基三乙氧基矽烷、苯乙基三丙氧基矽烷、苯乙基三異丙氧基矽烷、萘基三甲氧基矽烷、萘基三乙氧基矽烷、萘基三丙氧基矽烷、萘基三異丙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、二甲基二丙氧基矽烷、二甲基二異丙氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、二乙基二丙氧基矽烷、二乙基二異丙氧基矽烷、二丙基二甲氧基矽烷、二丙基二乙氧基矽烷、二丙基二丙氧基矽烷、二丙基二異丙氧基矽烷、二異丙基二甲氧基矽烷、二異丙基二乙氧基矽烷、二異丙基二丙氧基矽烷、二異丙基二異丙氧基矽烷、二丁基二甲氧基矽烷、二丁基二乙氧基矽烷、二丁基二丙氧基矽烷、二丁基二異丙氧基矽烷、二第二丁基二甲氧基矽烷、二第二丁基二乙氧基矽烷、二第二丁基二丙氧基矽烷、二第二丁基二異丙氧基矽烷、二第三丁基二甲氧基矽烷、二第三丁基二乙氧基矽烷、二第三丁基二丙氧基矽烷、二第三丁基二異丙氧基矽烷、二環丙基二甲氧基矽烷、二環丙基二乙氧基矽烷、二環丙基二丙氧基矽烷、二環丙基二異丙氧基矽烷、二環丁基二甲氧基矽烷、二環丁基二乙氧基矽烷、二環丁基二丙氧基矽烷、二環丁基二異丙氧基矽烷、二環戊基二甲氧基矽烷、二環戊基二乙氧基矽烷、二環戊基二丙氧基矽烷、二環戊基二異丙氧基矽烷、二環己基二甲氧基矽烷、二環己基二乙氧基矽烷、二環己基二丙氧基矽烷、二環己基二異丙氧基矽烷、二環己烯基二甲氧基矽烷、二環己烯基二乙氧基矽烷、二環己烯基二丙氧基矽烷、二環己烯基二異丙氧基矽烷、二環己烯基乙基二甲氧基矽烷、二環己烯基乙基二乙氧基矽烷、二環己烯基乙基二丙氧基矽烷、二環己烯基乙基二異丙氧基矽烷、二環辛基二甲氧基矽烷、二環辛基二乙氧基矽烷、二環辛基二丙氧基矽烷、二環辛基二異丙氧基矽烷、二環戊二烯基丙基二甲氧基矽烷、二環戊二烯基丙基二乙氧基矽烷、二環戊二烯基丙基二丙氧基矽烷、二環戊二烯基丙基二異丙氧基矽烷、雙(雙環庚烯基)二甲氧基矽烷、雙(雙環庚烯基)二乙氧基矽烷、雙(雙環庚烯基)二丙氧基矽烷、雙(雙環庚烯基)二異丙氧基矽烷、雙(雙環庚基)二甲氧基矽烷、雙(雙環庚基)二乙氧基矽烷、雙(雙環庚基)二丙氧基矽烷、雙(雙環庚基)二異丙氧基矽烷、二金剛烷基二甲氧基矽烷、二金剛烷基二乙氧基矽烷、二金剛烷基二丙氧基矽烷、二金剛烷基二異丙氧基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、二苯基二丙氧基矽烷、二苯基二異丙氧基矽烷、三甲基甲氧基矽烷、三甲基乙氧基矽烷、二甲基乙基甲氧基矽烷、二甲基乙基乙氧基矽烷、二甲基苯基甲氧基矽烷、二甲基苯基乙氧基矽烷、二甲基苄基甲氧基矽烷、二甲基苄基乙氧基矽烷、二甲基苯乙基甲氧基矽烷、二甲基苯乙基乙氧基矽烷等。
通式(2)可理想地例示:四甲氧基矽烷、四乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、異丙基三甲氧基矽烷、異丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、異丁基三甲氧基矽烷、異丁基三乙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、環戊基三甲氧基矽烷、環戊基三乙氧基矽烷、環己基三甲氧基矽烷、環己基三乙氧基矽烷、環己烯基三甲氧基矽烷、環己烯基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、苄基三甲氧基矽烷、苄基三乙氧基矽烷、甲苯基三甲氧基矽烷、甲苯基三乙氧基矽烷、甲氧基苄基三甲氧基矽烷、甲氧基苄基三乙氧基矽烷、苯乙基三甲氧基矽烷、苯乙基三乙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、二丙基二甲氧基矽烷、二丁基二甲氧基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、三甲基甲氧基矽烷、二甲基乙基甲氧基矽烷、二甲基苯基甲氧基矽烷、二甲基苄基甲氧基矽烷、二甲基苯乙基甲氧基矽烷等。
上述R
6表示之1價有機基之另一例,可列舉具有1個以上之碳-氧單鍵或碳-氧雙鍵之有機基。具體而言,係具有選自由環狀醚基、酯基、烷氧基、羥基構成之群組中之1種以上之基的有機基。其示例可列舉下列通式(Sm-R)表示者。
(P-Q
1-(S
1)
v1-Q
2-)
u-(T)
v2-Q
3-(S
2)
v3-Q
4-
(Sm-R)
通式(Sm-R)中,P為氫原子、環狀醚基、羥基、碳數1~4之烷氧基、碳數1~6之烷基羰基氧基、或碳數1~6之烷基羰基,Q
1、Q
2、Q
3、及Q
4各自獨立地為-C
qH
(2q-p)P
p-(式中,P與上述同樣,p為0~3之整數,q為0~10之整數(惟,q=0表示為單鍵。)。),u為0~3之整數,S
1與S
2各自獨立地表示-O-、-CO-、-OCO-、-COO-或-OCOO-。v1、v2、及v3各自獨立地表示0或1。同時,T為碳以外之2價原子,或為由亦可含有氧原子等雜原子之脂環、芳香環或雜環構成之2價基,就T而言,亦可含有氧原子等雜原子之脂環、芳香環或雜環之示例如下所示。T中與Q
2和與Q
3鍵結的位置並無特別限定,可考量立體性因素所致之反應性、反應所使用的市售試劑的取得性等而適當選擇。
通式(Sm-R)之具有1個以上之碳-氧單鍵或碳-氧雙鍵之有機基的較佳例,可列舉如下。此外,下式中,(Si)係用以表示與Si之鍵結位置而記載。
又,作為R
6之有機基之示例,亦可使用含有矽-矽鍵的有機基。具體而言可列舉如下。
又,作為R
6之有機基之示例,亦可使用具有會因酸分解之保護基的有機基。具體而言可列舉日本特開2013-167669號公報之(0058)段落至(0059)段落所列舉的有機基、由日本特開2013-224279號公報之(0060)段落所示之矽化合物獲得的有機基。
另外,R
6之有機基之示例,也可使用具有氟原子的有機基。具體而言可列舉由日本特開2012-053253號公報之(0062)段落至(0063)段落所示之矽化合物獲得的有機基。
[熱硬化性含矽材料之合成方法]
(合成方法1:酸觸媒)
本發明中熱硬化性含矽材料,例如可藉由將上述通式(1)表示之矽化合物(A-1)單獨、或將其與1種通式(2)表示之矽化合物(A-2)或2種以上之混合物(以下,記載為單體),在酸觸媒的存在下進行水解、或水解縮合而製造。以下,將水解或水解縮合中之任一者、或其兩者簡稱為水解縮合。
此時使用之酸觸媒可列舉:甲酸、乙酸、草酸、馬來酸、甲磺酸、苯磺酸、甲苯磺酸等有機酸;氫氟酸、鹽酸、氫溴酸、硫酸、硝酸、過氯酸、磷酸等無機酸等。觸媒的使用量相對於單體1莫耳,為1×10
-6~10莫耳,宜為1×10
-5~5莫耳,更佳為1×10
-4~1莫耳。
由該等單體利用水解縮合獲得熱硬化性含矽材料時的水的量,就鍵結於單體之水解性取代基每1莫耳而言,宜添加0.01~100莫耳,更佳為0.05~50莫耳,又更佳為0.1~30莫耳。若為該範圍內,反應使用的裝置變小,係經濟。
就操作方法而言,係在觸媒水溶液中添加單體並使水解縮合反應開始。此時,可在觸媒水溶液中添加有機溶劑,亦可將單體利用有機溶劑進行稀釋,也可實施兩種。反應溫度為0~100℃,宜為5~80℃。宜為於單體滴加時將溫度保持在5~80℃,之後在20~80℃使其熟成的方法較佳。
可添加至觸媒水溶液中的有機溶劑、或可稀釋單體的有機溶劑宜為:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、乙腈、四氫呋喃、甲苯、己烷、乙酸乙酯、甲乙酮、甲基異丁基酮、環己酮、甲基戊基酮、乙二醇、丙二醇、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇二甲醚、二乙二醇二甲醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯等及它們的混合物等。
該等有機溶劑中,宜為水溶性者。例如可列舉:甲醇、乙醇、1-丙醇、2-丙醇等醇類;乙二醇、丙二醇等多元醇;丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚等多元醇縮合物衍生物;丙酮、乙腈、四氫呋喃等。其中,尤其宜為沸點為100℃以下者。
此外,有機溶劑的使用量相對於單體1莫耳,宜為0~1,000ml,尤其宜為0~500ml。有機溶劑的使用量少的話,反應容器變小,係經濟。
之後,視需要進行觸媒的中和反應,得到反應混合物水溶液。此時,可使用於中和的鹼性物質的量,相對於觸媒所使用的酸宜為0.1~2當量。該鹼性物質只要是在水中呈現鹼性者,則可為任意物質。
然後,宜利用減壓去除等從反應混合物去除水解縮合反應所生成的醇等副產物。此時將反應混合物進行加熱的溫度取決於所添加之有機溶劑與反應產生之醇等的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的有機溶劑及醇等的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。雖難以正確得知此時去除的醇量,但去除約80質量%以上所生成的醇等較為理想。
然後,亦可從反應混合物將水解縮合所使用的酸觸媒去除。作為去除酸觸媒的方法,係將水與熱硬化性含矽材料混合,並利用有機溶劑萃取熱硬化性含矽材料。此時所使用之有機溶劑,宜為可溶解熱硬化性含矽材料,且與水混合則會分離成2層者。例如可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基戊基酮、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯、甲基異丁基酮、環戊基甲醚等及它們的混合物。
另外,亦可使用水溶性有機溶劑與水難溶性有機溶劑之混合物。例如宜為:甲醇-乙酸乙酯混合物、乙醇-乙酸乙酯混合物、1-丙醇-乙酸乙酯混合物、2-丙醇-乙酸乙酯混合物、丁二醇單甲醚-乙酸乙酯混合物、丙二醇單甲醚-乙酸乙酯混合物、乙二醇單甲醚-乙酸乙酯混合物、丁二醇單乙醚-乙酸乙酯混合物、丙二醇單乙醚-乙酸乙酯混合物、乙二醇單乙醚-乙酸乙酯混合物、丁二醇單丙醚-乙酸乙酯混合物、丙二醇單丙醚-乙酸乙酯混合物、乙二醇單丙醚-乙酸乙酯混合物、甲醇-甲基異丁基酮混合物、乙醇-甲基異丁基酮混合物、1-丙醇-甲基異丁基酮混合物、2-丙醇-甲基異丁基酮混合物、丙二醇單甲醚-甲基異丁基酮混合物、乙二醇單甲醚-甲基異丁基酮混合物、丙二醇單乙醚-甲基異丁基酮混合物、乙二醇單乙醚-甲基異丁基酮混合物、丙二醇單丙醚-甲基異丁基酮混合物、乙二醇單丙醚-甲基異丁基酮混合物、甲醇-環戊基甲醚混合物、乙醇-環戊基甲醚混合物、1-丙醇-環戊基甲醚混合物、2-丙醇-環戊基甲醚混合物、丙二醇單甲醚-環戊基甲醚混合物、乙二醇單甲醚-環戊基甲醚混合物、丙二醇單乙醚-環戊基甲醚混合物、乙二醇單乙醚-環戊基甲醚混合物、丙二醇單丙醚-環戊基甲醚混合物、乙二醇單丙醚-環戊基甲醚混合物、甲醇-丙二醇甲醚乙酸酯混合物、乙醇-丙二醇甲醚乙酸酯混合物、1-丙醇-丙二醇甲醚乙酸酯混合物、2-丙醇-丙二醇甲醚乙酸酯混合物、丙二醇單甲醚-丙二醇甲醚乙酸酯混合物、乙二醇單甲醚-丙二醇甲醚乙酸酯混合物、丙二醇單乙醚-丙二醇甲醚乙酸酯混合物、乙二醇單乙醚-丙二醇甲醚乙酸酯混合物、丙二醇單丙醚-丙二醇甲醚乙酸酯混合物、乙二醇單丙醚-丙二醇甲醚乙酸酯混合物等,但組合不限於該等。
此外,水溶性有機溶劑與水難溶性有機溶劑之混合比例可適當選擇,相對於水難溶性有機溶劑100質量份,水溶性有機溶劑為0.1~1,000質量份,宜為1~500質量份,又更佳為2~100質量份。
然後,亦可利用中性水進行洗淨。該中性水使用通常被稱為去離子水、超純水的水即可。該中性水的量相對於熱硬化性含矽材料溶液1L,為0.01~100L,宜為0.05~50L,更佳為0.1~5L。就該洗淨方法而言,將兩種溶液放入相同容器並攪拌,然後靜置將水層分離即可。洗淨次數為1次以上即可,宜為約1~5次。
作為其他將酸觸媒去除的方法,可列舉利用離子交換樹脂的方法、以環氧乙烷、環氧丙烷等環氧化合物中和後予以去除的方法。該等方法可配合反應所使用之酸觸媒而適當選擇。
利用此時的水洗操作,熱硬化性含矽材料的一部分會逃往水層,有時會獲得實質上與分級操作同等的效果,故水洗次數、洗淨水的量視觸媒去除效果與分級效果而適當選擇即可。
殘留有酸觸媒的熱硬化性含矽材料溶液及去除了酸觸媒的熱硬化性含矽材料溶液,均可藉由添加最終的溶劑並於減壓下進行溶劑交換,來獲得期望之含矽材料溶液。此時溶劑交換的溫度取決於欲去除的反應溶劑、萃取溶劑的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的萃取溶劑的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。
此時,會有因溶劑變化而導致熱硬化性含矽材料變得不穩定的情況。其係取決於最終的溶劑與熱硬化性含矽材料的相容性(compatibility)而會發生,為了防止此情況,亦可加入日本特開2009-126940號公報(0181)~(0182)段落記載之具有環狀醚作為取代基的1元或2元以上的醇作為穩定劑。添加量相對於溶劑交換前之溶液中之熱硬化性含矽材料100質量份,為0~25質量份,宜為0~15質量份,更佳為0~5質量份,但有添加時宜為0.5質量份以上。溶劑交換前之溶液中若有必要,也可添加具有環狀醚作為取代基之1元或2元以上之醇後再實施溶劑交換操作。
熱硬化性含矽材料濃縮到一定濃度以上的話,會有縮合反應進一步進行,變化成無法再溶解於有機溶劑的狀態之虞,故宜預先製成適當濃度的溶液狀態。又,過稀的話,溶劑的量變得過多,故預先製成適當濃度的溶液狀態係經濟且較佳。此時的濃度宜為0.1~20質量%。
添加至熱硬化性含矽材料溶液中的最終的溶劑宜為醇系溶劑、單烷醚衍生物,作為醇系溶劑,尤其宜為乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇、丁二醇等。作為單烷醚衍生物,具體而言,宜為丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚等。
該等溶劑若為主成分,則也可添加非醇系溶劑作為輔助溶劑。該輔助溶劑可例示:丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基戊基酮、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯、甲基異丁基酮、環戊基甲醚等。
又,作為使用了酸觸媒的另一反應操作,係於單體或單體之有機溶液中添加水或含水有機溶劑,使水解反應開始。此時觸媒可添加在單體或單體之有機溶液中,也可添加在水或含水有機溶劑中。反應溫度為0~100℃,宜為10~80℃。宜為於水滴加時加熱至10~50℃,之後升溫至20~80℃使其熟成的方法較佳。
使用有機溶劑時,宜為水溶性者,可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇等醇類;丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚等多元醇縮合物衍生物;丙酮、四氫呋喃、乙腈、及它們的混合物等。
有機溶劑的使用量相對於單體1莫耳,宜為0~1,000ml,尤其宜為0~500ml。有機溶劑的使用量少則反應容器變小,係經濟。獲得之反應混合物的後處理可和前述方法同樣地進行後處理,並獲得熱硬化性含矽材料。
(合成方法2:鹼觸媒)
又,熱硬化性含矽材料,例如可藉由將上述通式(1)表示之矽化合物(A-1)與1種通式(2)表示之矽化合物(A-2)或2種以上之混合物,在鹼觸媒的存在下進行水解縮合而製造。此時使用之鹼觸媒可列舉:甲胺、乙胺、丙胺、丁胺、乙二胺、六亞甲基二胺、二甲胺、二乙胺、乙基甲胺、三甲胺、三乙胺、三丙胺、三丁胺、環己胺、二環己胺、單乙醇胺、二乙醇胺、二甲基單乙醇胺、單甲基二乙醇胺、三乙醇胺、二氮雜雙環辛烷、二氮雜雙環環壬烯、二氮雜雙環十一烯、六亞甲基四胺、苯胺、N,N-二甲基苯胺、吡啶、N,N-二甲基胺基吡啶、吡咯、哌𠯤、吡咯啶、哌啶、甲基吡啶、四甲基氫氧化銨、氫氧化膽鹼、四丙基氫氧化銨、四丁基氫氧化銨、氨、氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化鋇、氫氧化鈣等。觸媒的使用量相對於單體1莫耳,為1×10
-6莫耳~10莫耳,宜為1×10
-5莫耳~5莫耳,更佳為1×10
-4莫耳~1莫耳。
由上述單體利用水解縮合獲得熱硬化性含矽材料時的水的量,就鍵結於單體之水解性取代基每1莫耳而言,宜添加0.1~50莫耳。若為該範圍內,反應使用的裝置變小,係經濟。
就操作方法而言,係在觸媒水溶液中添加單體並使水解縮合反應開始。此時,可在觸媒水溶液中添加有機溶劑,亦可將單體利用有機溶劑進行稀釋,也可實施兩種。反應溫度為0~100℃,宜為5~80℃。宜為於單體滴加時將溫度保持在5~80℃,之後在20~80℃使其熟成的方法較佳。
可添加至鹼觸媒水溶液中的有機溶劑、或可稀釋單體的有機溶劑,宜使用與就可添加至酸觸媒水溶液中者所例示的有機溶劑同樣者。此外,為了經濟地實施反應,有機溶劑的使用量相對於單體1莫耳宜為0~1,000ml。
之後,視需要進行觸媒的中和反應,得到反應混合物水溶液。此時,可使用於中和的酸性物質的量,相對於觸媒所使用的鹼性物質宜為0.1~2當量。該酸性物質只要是在水中呈現酸性者,則可為任意物質。
然後,宜利用減壓去除等從反應混合物去除水解縮合反應所生成的醇等副產物。將反應混合物進行加熱的溫度取決於所添加之有機溶劑與反應產生之醇等的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的有機溶劑及醇的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。雖難以正確得知此時去除的醇量,但去除約80質量%以上所生成的醇較為理想。
然後,為了去除水解縮合所使用之鹼觸媒,利用有機溶劑萃取熱硬化性含矽材料。此時所使用之有機溶劑,宜為可溶解熱硬化性含矽材料,且與水混合則會分離成2層者。另外,亦可使用水溶性有機溶劑與水難溶性有機溶劑之混合物。
去除鹼觸媒時使用的有機溶劑之具體例,可使用與就去除酸觸媒時所使用者具體例示的上述有機溶劑、水溶性有機溶劑與水難性有機溶劑之混合物同樣者。
此時所使用之有機溶劑,宜為可溶解熱硬化性含矽材料,且與水混合則會分離成2層者。例如可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基戊基酮、丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯、甲基異丁基酮、環戊基甲醚等、及它們的混合物。
此外,水溶性有機溶劑與水難溶性有機溶劑之混合比例可適當選擇,相對於難溶性有機溶劑100質量份,水溶性有機溶劑為0.1~1,000質量份,宜為1~500質量份,又更佳為2~100質量份。
然後,利用中性水洗淨。該中性水使用通常被稱為去離子水、超純水的水即可。該中性水的量相對於熱硬化性含矽材料溶液1L,為0.01~100L,宜為0.05~50L,更佳為0.1~5L。就該洗淨方法而言,將兩種溶液放入相同容器並攪拌,然後靜置將水層分離即可。洗淨次數為1次以上即可,宜為約1~5次。
藉由在洗淨完畢的熱硬化性含矽材料溶液中,添加最終的溶劑,於減壓下進行溶劑交換,而獲得期望之熱硬化性含矽材料溶液。此時溶劑交換的溫度取決於欲去除的萃取溶劑的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的萃取溶劑的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。
添加至熱硬化性含矽材料溶液中的最終的溶劑,宜為醇系溶劑、單烷醚,作為醇系溶劑,尤其宜為乙二醇、二乙二醇、三乙二醇等。作為單烷醚,具體而言,宜為丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇單丙醚、乙二醇單丙醚等。
又,作為使用了鹼觸媒之另一反應操作,係於單體或單體之有機溶液中添加水或含水有機溶劑,使水解反應開始。此時觸媒可添加在單體或單體之有機溶液中,也可添加在水或含水有機溶劑中。反應溫度為0~100℃,宜為10~80℃。宜為於水滴加時加熱至10~50℃,之後升溫至20~80℃使其熟成的方法較佳。
可作為單體之有機溶液或含水有機溶劑使用的有機溶劑,宜為水溶性者,可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇等醇類;丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚等多元醇縮合物衍生物;丙酮、四氫呋喃、乙腈、及它們的混合物等。
利用上述合成方法1或2獲得之熱硬化性含矽材料之分子量,不僅可藉由單體的選擇來調整,還可藉由控制聚合時的反應條件來調整,宜使用100,000以下,更佳為200~50,000,又更佳為300~30,000者。重量平均分子量為100,000以下的話,不會有產生異物、發生塗布不均的情況。
此外,關於上述重量平均分子量的數據,係利用使用RI作為檢測器,並使用四氫呋喃作為溶離溶劑的凝膠滲透層析法(GPC),並使用聚苯乙烯作為標準物質,以聚苯乙烯換算來表示分子量。
本發明之含矽之阻劑下層膜形成用組成物,如後述可更含有交聯觸媒。
本發明中,熱硬化性含矽材料可將水解性單體以利用了酸或鹼觸媒之條件製得,另外,亦可使用將該單體與下列通式(Mm)表示之水解性金屬化合物之混合物以利用了前述酸或鹼觸媒之條件製得的聚矽氧烷衍生物作為阻劑下層膜組成物的成分。
U(OR
8)
m8(OR
9)
m9(Mm)
式中,R
8、R
9為碳數1~30之有機基,m8+m9為依U的種類而決定的和價數相同的數,m8、m9為0以上之整數,U為周期表的III族、IV族、V族、XIII族、XIV族、或XV族元素,且排除碳及矽。
此時使用之水解性金屬化合物(Mm)可例示如下。
U為硼時,通式(Mm)表示之化合物可例示甲氧基硼、乙氧基硼、丙氧基硼、丁氧基硼、戊氧基硼、己氧基硼、環戊氧基硼、環己氧基硼、烯丙氧基硼、苯氧基硼、甲氧基乙氧基硼、硼酸、氧化硼等作為水解性金屬化合物。
U為鋁時,通式(Mm)表示之化合物可例示甲氧基鋁、乙氧基鋁、丙氧基鋁、丁氧基鋁、戊氧基鋁、己氧基鋁、環戊氧基鋁、環己氧基鋁、烯丙氧基鋁、苯氧基鋁、甲氧基乙氧基鋁、乙氧基乙氧基鋁、二丙氧基乙基乙醯乙酸鋁、二丁氧基乙基乙醯乙酸鋁、丙氧基雙乙基乙醯乙酸鋁、丁氧基雙乙基乙醯乙酸鋁、2,4-戊二酮酸鋁、2,2,6,6-四甲基-3,5-庚二酮酸鋁等作為水解性金屬化合物。
U為鎵時,通式(Mm)表示之化合物可例示甲氧基鎵、乙氧基鎵、丙氧基鎵、丁氧基鎵、戊氧基鎵、己氧基鎵、環戊氧基鎵、環己氧基鎵、烯丙氧基鎵、苯氧基鎵、甲氧基乙氧基鎵、乙氧基乙氧基鎵、二丙氧基乙基乙醯乙酸鎵、二丁氧基乙基乙醯乙酸鎵、丙氧基雙乙基乙醯乙酸鎵、丁氧基雙乙基乙醯乙酸鎵、2,4-戊二酮酸鎵、2,2,6,6-四甲基-3,5-庚二酮酸鎵等作為水解性金屬化合物。
U為釔時,通式(Mm)表示之化合物可例示甲氧基釔、乙氧基釔、丙氧基釔、丁氧基釔、戊氧基釔、己氧基釔、環戊氧基釔、環己氧基釔、烯丙氧基釔、苯氧基釔、甲氧基乙氧基釔、乙氧基乙氧基釔、二丙氧基乙基乙醯乙酸釔、二丁氧基乙基乙醯乙酸釔、丙氧基雙乙基乙醯乙酸釔、丁氧基雙乙基乙醯乙酸釔、2,4-戊二酮酸釔、2,2,6,6-四甲基-3,5-庚二酮酸釔等作為水解性金屬化合物。
U為鍺時,通式(Mm)表示之化合物可例示甲氧基鍺、乙氧基鍺、丙氧基鍺、丁氧基鍺、戊氧基鍺、己氧基鍺、環戊氧基鍺、環己氧基鍺、烯丙氧基鍺、苯氧基鍺、甲氧基乙氧基鍺、乙氧基乙氧基鍺等作為水解性金屬化合物。
U為鈦時,通式(Mm)表示之化合物可例示甲氧基鈦、乙氧基鈦、丙氧基鈦、丁氧基鈦、戊氧基鈦、己氧基鈦、環戊氧基鈦、環己氧基鈦、烯丙氧基鈦、苯氧基鈦、甲氧基乙氧基鈦、乙氧基乙氧基鈦、二丙氧基雙乙基乙醯乙酸鈦、二丁氧基雙乙基乙醯乙酸鈦、二丙氧基雙2,4-戊二酮酸鈦、二丁氧基雙2,4-戊二酮酸鈦等作為水解性金屬化合物。
U為鉿時,通式(Mm)表示之化合物可例示甲氧基鉿、乙氧基鉿、丙氧基鉿、丁氧基鉿、戊氧基鉿、己氧基鉿、環戊氧基鉿、環己氧基鉿、烯丙氧基鉿、苯氧基鉿、甲氧基乙氧基鉿、乙氧基乙氧基鉿、二丙氧基雙乙基乙醯乙酸鉿、二丁氧基雙乙基乙醯乙酸鉿、二丙氧基雙2,4-戊二酮酸鉿、二丁氧基雙2,4-戊二酮酸鉿等作為水解性金屬化合物。
U為錫時,通式(Mm)表示之化合物可例示甲氧基錫、乙氧基錫、丙氧基錫、丁氧基錫、苯氧基錫、甲氧基乙氧基錫、乙氧基乙氧基錫、2,4-戊二酮酸錫、2,2,6,6-四甲基-3,5-庚二酮酸錫等作為水解性金屬化合物。
U為砷時,通式(Mm)表示之化合物可例示甲氧基砷、乙氧基砷、丙氧基砷、丁氧基砷、苯氧基砷等作為水解性金屬化合物。
U為銻時,通式(Mm)表示之化合物可例示甲氧基銻、乙氧基銻、丙氧基銻、丁氧基銻、苯氧基銻、乙酸銻、丙酸銻等作為水解性金屬化合物。
U為鈮時,通式(Mm)表示之化合物可例示甲氧基鈮、乙氧基鈮、丙氧基鈮、丁氧基鈮、苯氧基鈮等作為水解性金屬化合物。
U為鉭時,通式(Mm)表示之化合物可例示甲氧基鉭、乙氧基鉭、丙氧基鉭、丁氧基鉭、苯氧基鉭等作為水解性金屬化合物。
U為鉍時,通式(Mm)表示之化合物可例示甲氧基鉍、乙氧基鉍、丙氧基鉍、丁氧基鉍、苯氧基鉍等作為水解性金屬化合物。
U為磷時,通式(Mm)表示之化合物可例示磷酸三甲酯、磷酸三乙酯、磷酸三丙酯、亞磷酸三甲酯、亞磷酸三乙酯、亞磷酸三丙酯、五氧化二磷等作為水解性金屬化合物。
U為釩時,通式(Mm)表示之化合物可例示雙(2,4-戊二酮酸)氧化釩、2,4-戊二酮酸釩、三丁氧基氧化釩、三丙氧基氧化釩等作為水解性金屬化合物。
U為鋯時,通式(Mm)表示之化合物可例示甲氧基鋯、乙氧基鋯、丙氧基鋯、丁氧基鋯、苯氧基鋯、雙(2,4-戊二酮酸)二丁氧基鋯、雙(2,2,6,6-四甲基-3,5-庚二酮酸)二丙氧基鋯等作為水解性金屬化合物。
(交聯觸媒)
本發明中,可將交聯觸媒(Xc)摻合至含矽之阻劑下層膜形成用組成物中。能摻合的交聯觸媒,可列舉下列通式(Xc0)表示之化合物。
L
aH
bA (Xc0)
式中,L為鋰、鈉、鉀、銣、銫、鋶、錪、鏻或銨,A為非親核性相對離子,a為1以上之整數,b為0或1以上之整數,且a+b為非親核性相對離子的價數。
就作為具體的(Xc0)的本發明中使用之交聯觸媒而言,可列舉下列通式(Xc-1)之鋶鹽、(Xc-2)之錪鹽、(Xc-3)之鏻鹽、(Xc-4)之銨鹽、鹼金屬鹽等。
鋶鹽(Xc-1)、錪鹽(Xc-2)、鏻鹽(Xc-3)可例示如下。
[化34]
又,銨鹽(Xc-4)可例示如下。
[化35]
式中,R
204、R
205、R
206、R
207各自表示碳數1~12之直鏈狀、分支狀或環狀之烷基、烯基、側氧基烷基或側氧基烯基、碳數6~20之取代或非取代之芳基、或碳數7~12之芳烷基或芳基側氧基烷基,該等基之氫原子之一部分或全部亦可被烷氧基取代等。又,R
205與R
206亦可形成環,形成環時,R
205、R
206各自表示碳數1~6之伸烷基。A
-表示非親核性相對離子。R
208、R
209、R
210、R
211,係與R
204、R
205、R
206、R
207同樣,但亦可為氫原子。R
208與R
209、R
208與R
209與R
210亦可形成環,形成環時,R
208與R
209及R
208與R
209與R
210表示碳數3~10之伸烷基。
上述R
204、R
205、R
206、R
207、R
208、R
209、R
210、R
211彼此可相同也可不同,具體而言,烷基可列舉:甲基、乙基、丙基、異丙基、正丁基、第二丁基、第三丁基、戊基、己基、庚基、辛基、環戊基、環己基、環庚基、環丙基甲基、4-甲基環己基、環己基甲基、降莰基、金剛烷基等。烯基可列舉:乙烯基、烯丙基、丙烯基、丁烯基、己烯基、環己烯基等。側氧基烷基可列舉:2-側氧基環戊基、2-側氧基環己基、2-側氧基丙基、2-環戊基-2-側氧基乙基、2-環己基-2-側氧基乙基、2-(4-甲基環己基)-2-側氧基乙基等。側氧基烯基可列舉:丙烯醯基、甲基丙烯醯基、巴豆醯基等。芳基可列舉:苯基、萘基等;對甲氧基苯基、間甲氧基苯基、鄰甲氧基苯基、乙氧基苯基、對第三丁氧基苯基、間第三丁氧基苯基等烷氧基苯基;2-甲基苯基、3-甲基苯基、4-甲基苯基、乙基苯基、4-第三丁基苯基、4-丁基苯基、二甲基苯基等烷基苯基;甲基萘基、乙基萘基等烷基萘基;甲氧基萘基、乙氧基萘基等烷氧基萘基;二甲基萘基、二乙基萘基等二烷基萘基;二甲氧基萘基、二乙氧基萘基等二烷氧基萘基等。芳烷基可列舉:苄基、苯基乙基、苯乙基等。芳基側氧基烷基可列舉:2-苯基-2-側氧基乙基、2-(1-萘基)-2-側氧基乙基、2-(2-萘基)-2-側氧基乙基等2-芳基-2-側氧基乙基等。
A
-之非親核性相對離子可列舉:氫氧根離子、甲酸根離子、乙酸根離子、丙酸根離子、丁酸根離子、戊酸根離子、己酸根離子、庚酸根離子、辛酸根離子、壬酸根離子、癸酸根離子、油酸根離子、硬脂酸根離子、亞麻油酸根離子、次亞麻油酸根離子、苯甲酸根離子、鄰苯二甲酸根離子、間苯二甲酸根離子、對苯二甲酸根離子、水楊酸根離子、三氟乙酸根離子、單氯乙酸根離子、二氯乙酸根離子、三氯乙酸根離子、氟離子、氯離子、溴離子、碘離子、硝酸根離子、亞硝酸根離子、氯酸根離子、溴酸根離子、甲磺酸根離子、對甲苯磺酸根離子、單甲基硫酸根離子等1價離子、1價或2價之草酸根離子、丙二酸根離子、甲基丙二酸根離子、乙基丙二酸根離子、丙基丙二酸根離子、丁基丙二酸根離子、二甲基丙二酸根離子、二乙基丙二酸根離子、琥珀酸根離子、甲基琥珀酸根離子、戊二酸根離子、己二酸根離子、伊康酸根離子、馬來酸根離子、富馬酸根離子、檸康酸根離子、檸檬酸根離子、碳酸根離子、硫酸根離子等。
鹼金屬鹽可列舉:鋰、鈉、鉀、銫、鎂、鈣的氫氧化鹽、甲酸鹽、乙酸鹽、丙酸鹽、丁酸鹽、戊酸鹽、己酸鹽、庚酸鹽、辛酸鹽、壬酸鹽、癸酸鹽、油酸鹽、硬脂酸鹽、亞麻油酸鹽、次亞麻油酸鹽、苯甲酸鹽、鄰苯二甲酸鹽、間苯二甲酸鹽、對苯二甲酸鹽、水楊酸鹽、三氟乙酸鹽、單氯乙酸鹽、二氯乙酸鹽、三氯乙酸鹽等1價鹽、1價或2價之草酸鹽、丙二酸鹽、甲基丙二酸鹽、乙基丙二酸鹽、丙基丙二酸鹽、丁基丙二酸鹽、二甲基丙二酸鹽、二乙基丙二酸鹽、琥珀酸鹽、甲基琥珀酸鹽、戊二酸鹽、己二酸鹽、伊康酸鹽、馬來酸鹽、富馬酸鹽、檸康酸鹽、檸檬酸鹽、碳酸鹽等。
具體而言,鋶鹽(Xc-1)可列舉:甲酸三苯基鋶、乙酸三苯基鋶、丙酸三苯基鋶、丁酸三苯基鋶、苯甲酸三苯基鋶、鄰苯二甲酸三苯基鋶、間苯二甲酸三苯基鋶、對苯二甲酸三苯基鋶、水楊酸三苯基鋶、三氟甲磺酸三苯基鋶、三氟乙酸三苯基鋶、單氯乙酸三苯基鋶、二氯乙酸三苯基鋶、三氯乙酸三苯基鋶、氫氧化三苯基鋶、硝酸三苯基鋶、氯化三苯基鋶、溴化三苯基鋶、草酸三苯基鋶、丙二酸三苯基鋶、甲基丙二酸三苯基鋶、乙基丙二酸三苯基鋶、丙基丙二酸三苯基鋶、丁基丙二酸三苯基鋶、二甲基丙二酸三苯基鋶、二乙基丙二酸三苯基鋶、琥珀酸三苯基鋶、甲基琥珀酸三苯基鋶、戊二酸三苯基鋶、己二酸三苯基鋶、伊康酸三苯基鋶、草酸雙三苯基鋶、馬來酸三苯基鋶、富馬酸三苯基鋶、檸康酸三苯基鋶、檸檬酸三苯基鋶、碳酸三苯基鋶、草酸雙三苯基鋶、馬來酸雙三苯基鋶、富馬酸雙三苯基鋶、檸康酸雙三苯基鋶、檸檬酸雙三苯基鋶、碳酸雙三苯基鋶等。
又,作為錪鹽(Xc-2),具體而言,可列舉:甲酸二苯基錪、乙酸二苯基錪、丙酸二苯基錪、丁酸二苯基錪、苯甲酸二苯基錪、鄰苯二甲酸二苯基錪、間苯二甲酸二苯基錪、對苯二甲酸二苯基錪、水楊酸二苯基錪、三氟甲磺酸二苯基錪、三氟乙酸二苯基錪、單氯乙酸二苯基錪、二氯乙酸二苯基錪、三氯乙酸二苯基錪、氫氧化二苯基錪、硝酸二苯基錪、氯化二苯基錪、溴化二苯基錪、碘化二苯基錪、草酸二苯基錪、馬來酸二苯基錪、富馬酸二苯基錪、檸康酸二苯基錪、檸檬酸二苯基錪、碳酸二苯基錪、草酸雙二苯基錪、馬來酸雙二苯基錪、富馬酸雙二苯基錪、檸康酸雙二苯基錪、檸檬酸雙二苯基錪、碳酸雙二苯基錪等。
又,作為鏻鹽(Xc-3),具體而言,可列舉:甲酸四乙基鏻、乙酸四乙基鏻、丙酸四乙基鏻、丁酸四乙基鏻、苯甲酸四乙基鏻、鄰苯二甲酸四乙基鏻、間苯二甲酸四乙基鏻、對苯二甲酸四乙基鏻、水楊酸四乙基鏻、三氟甲磺酸四乙基鏻、三氟乙酸四乙基鏻、單氯乙酸四乙基鏻、二氯乙酸四乙基鏻、三氯乙酸四乙基鏻、氫氧化四乙基鏻、硝酸四乙基鏻、氯化四乙基鏻、溴化四乙基鏻、碘化四乙基鏻、草酸四乙基鏻、馬來酸四乙基鏻、富馬酸四乙基鏻、檸康酸四乙基鏻、檸檬酸四乙基鏻、碳酸四乙基鏻、草酸雙四乙基鏻、馬來酸雙四乙基鏻、富馬酸雙四乙基鏻、檸康酸雙四乙基鏻、檸檬酸雙四乙基鏻、碳酸雙四乙基鏻、甲酸四苯基鏻、乙酸四苯基鏻、丙酸四苯基鏻、丁酸四苯基鏻、苯甲酸四苯基鏻、鄰苯二甲酸四苯基鏻、間苯二甲酸四苯基鏻、對苯二甲酸四苯基鏻、水楊酸四苯基鏻、三氟甲磺酸四苯基鏻、三氟乙酸四苯基鏻、單氯乙酸四苯基鏻、二氯乙酸四苯基鏻、三氯乙酸四苯基鏻、氫氧化四苯基鏻、硝酸四苯基鏻、氯化四苯基鏻、溴化四苯基鏻、碘化四苯基鏻、草酸四苯基鏻、馬來酸四苯基鏻、富馬酸四苯基鏻、檸康酸四苯基鏻、檸檬酸四苯基鏻、碳酸四苯基鏻、草酸雙四苯基鏻、馬來酸雙四苯基鏻、富馬酸雙四苯基鏻、檸康酸雙四苯基鏻、檸檬酸雙四苯基鏻、碳酸雙四苯基鏻等。
又,作為銨鹽(Xc-4),具體而言,可例示:甲酸四甲基銨、乙酸四甲基銨、丙酸四甲基銨、丁酸四甲基銨、苯甲酸四甲基銨、鄰苯二甲酸四甲基銨、間苯二甲酸四甲基銨、對苯二甲酸四甲基銨、水楊酸四甲基銨、三氟甲磺酸四甲基銨、三氟乙酸四甲基銨、單氯乙酸四甲基銨、二氯乙酸四甲基銨、三氯乙酸四甲基銨、氫氧化四甲基銨、硝酸四甲基銨、氯化四甲基銨、溴化四甲基銨、碘化四甲基銨、單甲基硫酸四甲基銨、草酸四甲基銨、丙二酸四甲基銨、馬來酸四甲基銨、富馬酸四甲基銨、檸康酸四甲基銨、檸檬酸四甲基銨、碳酸四甲基銨、草酸雙四甲基銨、丙二酸雙四甲基銨、馬來酸雙四甲基銨、富馬酸雙四甲基銨、檸康酸雙四甲基銨、檸檬酸雙四甲基銨、碳酸雙四甲基銨、甲酸四乙基銨、乙酸四乙基銨、丙酸四乙基銨、丁酸四乙基銨、苯甲酸四乙基銨、鄰苯二甲酸四乙基銨、間苯二甲酸四乙基銨、對苯二甲酸四乙基銨、水楊酸四乙基銨、三氟甲磺酸四乙基銨、三氟乙酸四乙基銨、單氯乙酸四乙基銨、二氯乙酸四乙基銨、三氯乙酸四乙基銨、氫氧化四乙基銨、硝酸四乙基銨、氯化四乙基銨、溴化四乙基銨、碘化四乙基銨、單甲基硫酸四乙基銨、草酸四乙基銨、丙二酸四乙基銨、馬來酸四乙基銨、富馬酸四乙基銨、檸康酸四乙基銨、檸檬酸四乙基銨、碳酸四乙基銨、草酸雙四乙基銨、丙二酸雙四乙基銨、馬來酸雙四乙基銨、富馬酸雙四乙基銨、檸康酸雙四乙基銨、檸檬酸雙四乙基銨、碳酸雙四乙基銨、甲酸四丙基銨、乙酸四丙基銨、丙酸四丙基銨、丁酸四丙基銨、苯甲酸四丙基銨、鄰苯二甲酸四丙基銨、間苯二甲酸四丙基銨、對苯二甲酸四丙基銨、水楊酸四丙基銨、三氟甲磺酸四丙基銨、三氟乙酸四丙基銨、單氯乙酸四丙基銨、二氯乙酸四丙基銨、三氯乙酸四丙基銨、氫氧化四丙基銨、硝酸四丙基銨、氯化四丙基銨、溴化四丙基銨、碘化四丙基銨、單甲基硫酸四丙基銨、草酸四丙基銨、丙二酸四丙基銨、馬來酸四丙基銨、富馬酸四丙基銨、檸康酸四丙基銨、檸檬酸四丙基銨、碳酸四丙基銨、草酸雙四丙基銨、丙二酸雙四丙基銨、馬來酸雙四丙基銨、富馬酸雙四丙基銨、檸康酸雙四丙基銨、檸檬酸雙四丙基銨、碳酸雙四丙基銨、甲酸四丁基銨、乙酸四丁基銨、丙酸四丁基銨、丁酸四丁基銨、苯甲酸四丁基銨、鄰苯二甲酸四丁基銨、間苯二甲酸四丁基銨、對苯二甲酸四丁基銨、水楊酸四丁基銨、三氟甲磺酸四丁基銨、三氟乙酸四丁基銨、單氯乙酸四丁基銨、二氯乙酸四丁基銨、三氯乙酸四丁基銨、氫氧化四丁基銨、硝酸四丁基銨、氯化四丁基銨、溴化四丁基銨、碘化四丁基銨、甲磺酸四丁基銨、單甲基硫酸四丁基銨、草酸四丁基銨、丙二酸四丁基銨、馬來酸四丁基銨、富馬酸四丁基銨、檸康酸四丁基銨、檸檬酸四丁基銨、碳酸四丁基銨、草酸雙四丁基銨、丙二酸雙四丁基銨、馬來酸雙四丁基銨、富馬酸雙四丁基銨、檸康酸雙四丁基銨、檸檬酸雙四丁基銨、碳酸雙四丁基銨、甲酸三甲基苯基銨、乙酸三甲基苯基銨、丙酸三甲基苯基銨、丁酸三甲基苯基銨、苯甲酸三甲基苯基銨、鄰苯二甲酸三甲基苯基銨、間苯二甲酸三甲基苯基銨、對苯二甲酸三甲基苯基銨、水楊酸三甲基苯基銨、三氟甲磺酸三甲基苯基銨、三氟乙酸三甲基苯基銨、單氯乙酸三甲基苯基銨、二氯乙酸三甲基苯基銨、三氯乙酸三甲基苯基銨、氫氧化三甲基苯基銨、硝酸三甲基苯基銨、氯化三甲基苯基銨、溴化三甲基苯基銨、碘化三甲基苯基銨、甲磺酸三甲基苯基銨、單甲基硫酸三甲基苯基銨、草酸三甲基苯基銨、丙二酸三甲基苯基銨、馬來酸三甲基苯基銨、富馬酸三甲基苯基銨、檸康酸三甲基苯基銨、檸檬酸三甲基苯基銨、碳酸三甲基苯基銨、草酸雙三甲基苯基銨、丙二酸雙三甲基苯基銨、馬來酸雙三甲基苯基銨、富馬酸雙三甲基苯基銨、檸康酸雙三甲基苯基銨、檸檬酸雙三甲基苯基銨、碳酸雙三甲基苯基銨、甲酸三乙基苯基銨、乙酸三乙基苯基銨、丙酸三乙基苯基銨、丁酸三乙基苯基銨、苯甲酸三乙基苯基銨、鄰苯二甲酸三乙基苯基銨、間苯二甲酸三乙基苯基銨、對苯二甲酸三乙基苯基銨、水楊酸三乙基苯基銨、三氟甲磺酸三乙基苯基銨、三氟乙酸三乙基苯基銨、單氯乙酸三乙基苯基銨、二氯乙酸三乙基苯基銨、三氯乙酸三乙基苯基銨、氫氧化三乙基苯基銨、硝酸三乙基苯基銨、氯化三乙基苯基銨、溴化三乙基苯基銨、碘化三乙基苯基銨、甲磺酸三乙基苯基銨、單甲基硫酸三乙基苯基銨、草酸三乙基苯基銨、丙二酸三乙基苯基銨、馬來酸三乙基苯基銨、富馬酸三乙基苯基銨、檸康酸三乙基苯基銨、檸檬酸三乙基苯基銨、碳酸三乙基苯基銨、草酸雙三乙基苯基銨、丙二酸雙三乙基苯基銨、馬來酸雙三乙基苯基銨、富馬酸雙三乙基苯基銨、檸康酸雙三乙基苯基銨、檸檬酸雙三乙基苯基銨、碳酸雙三乙基苯基銨、甲酸苄基二甲基苯基銨、乙酸苄基二甲基苯基銨、丙酸苄基二甲基苯基銨、丁酸苄基二甲基苯基銨、苯甲酸苄基二甲基苯基銨、鄰苯二甲酸苄基二甲基苯基銨、間苯二甲酸苄基二甲基苯基銨、對苯二甲酸苄基二甲基苯基銨、水楊酸苄基二甲基苯基銨、三氟甲磺酸苄基二甲基苯基銨、三氟乙酸苄基二甲基苯基銨、單氯乙酸苄基二甲基苯基銨、二氯乙酸苄基二甲基苯基銨、三氯乙酸苄基二甲基苯基銨、氫氧化苄基二甲基苯基銨、硝酸苄基二甲基苯基銨、氯化苄基二甲基苯基銨、溴化苄基二甲基苯基銨、碘化苄基二甲基苯基銨、甲磺酸苄基二甲基苯基銨、單甲基硫酸苄基二甲基苯基銨、草酸苄基二甲基苯基銨、丙二酸苄基二甲基苯基銨、馬來酸苄基二甲基苯基銨、富馬酸苄基二甲基苯基銨、檸康酸苄基二甲基苯基銨、檸檬酸苄基二甲基苯基銨、碳酸苄基二甲基苯基銨、草酸雙苄基二甲基苯基銨、丙二酸雙苄基二甲基苯基銨、馬來酸雙苄基二甲基苯基銨、富馬酸雙苄基二甲基苯基銨、檸康酸雙苄基二甲基苯基銨、檸檬酸雙苄基二甲基苯基銨、碳酸雙苄基二甲基苯基銨等。
鹼金屬鹽可例示:甲酸鋰、乙酸鋰、丙酸鋰、丁酸鋰、苯甲酸鋰、鄰苯二甲酸鋰、間苯二甲酸鋰、對苯二甲酸鋰、水楊酸鋰、三氟甲磺酸鋰、三氟乙酸鋰、單氯乙酸鋰、二氯乙酸鋰、三氯乙酸鋰、氫氧化鋰、硝酸鋰、氯化鋰、溴化鋰、碘化鋰、甲磺酸鋰、草酸氫鋰、丙二酸氫鋰、馬來酸氫鋰、富馬酸氫鋰、檸康酸氫鋰、檸檬酸氫鋰、碳酸氫鋰、草酸鋰、丙二酸鋰、馬來酸鋰、富馬酸鋰、檸康酸鋰、檸檬酸鋰、碳酸鋰、甲酸鈉、乙酸鈉、丙酸鈉、丁酸鈉、苯甲酸鈉、鄰苯二甲酸鈉、間苯二甲酸鈉、對苯二甲酸鈉、水楊酸鈉、三氟甲磺酸鈉、三氟乙酸鈉、單氯乙酸鈉、二氯乙酸鈉、三氯乙酸鈉、氫氧化鈉、硝酸鈉、氯化鈉、溴化鈉、碘化鈉、甲磺酸鈉、草酸氫鈉、丙二酸氫鈉、馬來酸氫鈉、富馬酸氫鈉、檸康酸氫鈉、檸檬酸氫鈉、碳酸氫鈉、草酸鈉、丙二酸鈉、馬來酸鈉、富馬酸鈉、檸康酸鈉、檸檬酸鈉、碳酸鈉、甲酸鉀、乙酸鉀、丙酸鉀、丁酸鉀、苯甲酸鉀、鄰苯二甲酸鉀、間苯二甲酸鉀、對苯二甲酸鉀、水楊酸鉀、三氟甲磺酸鉀、三氟乙酸鉀、單氯乙酸鉀、二氯乙酸鉀、三氯乙酸鉀、氫氧化鉀、硝酸鉀、氯化鉀、溴化鉀、碘化鉀、甲磺酸鉀、草酸氫鉀、丙二酸氫鉀、馬來酸氫鉀、富馬酸氫鉀、檸康酸氫鉀、檸檬酸氫鉀、碳酸氫鉀、草酸鉀、丙二酸鉀、馬來酸鉀、富馬酸鉀、檸康酸鉀、檸檬酸鉀、碳酸鉀等。
本發明中,亦可於含矽之阻劑下層膜形成用組成物中摻合具有鋶鹽、錪鹽、鏻鹽、銨鹽作為結構之一部分的聚矽氧烷(Xc-10)作為交聯觸媒(Xc)。
作為用以製造此處所使用之(Xc-10)的原料,可使用下列通式(Xm)表示之化合物。
R
1A A1R
2A A2R
3A A3Si(OR
0A)
(4-A1-A2-A3)(Xm)
式中,R
0A為碳數1~6之烴基,R
1A、R
2A、R
3A中之至少一者為具有銨鹽、鋶鹽、鏻鹽、錪鹽之有機基,其他為氫原子或碳數1~30之1價有機基。A1、A2、A3為0或1,1≦A1+A2+A3≦3。
此處,R
0A可例示:甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、環戊基、正己基、環己基、苯基。
式中,R
SA1、R
SA2各自表示碳數1~20之直鏈狀、分支狀或環狀之烷基、烯基、側氧基烷基或側氧基烯基、碳數6~20之取代或非取代之芳基、或碳數7~20之芳烷基或芳氧基烷基,該等基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基、鹵素原子等取代。又,R
SA1與R
SA2亦可和它們所鍵結之硫原子一起形成環,形成環時,R
SA1、R
SA2各自表示碳數1~6之伸烷基。R
SA3為碳數1~20之直鏈狀、分支狀或環狀之伸烷基、伸烯基、碳數6~20之取代或非取代之伸芳基或伸芳烷基,該等基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基等取代。R
SA1、R
SA2、R
SA3也可在其鏈或環之中具有氧原子或氮原子。
X
-可列舉:氫氧根離子、甲酸根離子、乙酸根離子、丙酸根離子、丁酸根離子、戊酸根離子、己酸根離子、庚酸根離子、辛酸根離子、壬酸根離子、癸酸根離子、油酸根離子、硬脂酸根離子、亞麻油酸根離子、次亞麻油酸根離子、苯甲酸根離子、對甲基苯甲酸根離子、對第三丁基苯甲酸根離子、鄰苯二甲酸根離子、間苯二甲酸根離子、對苯二甲酸根離子、水楊酸根離子、三氟乙酸根離子、單氯乙酸根離子、二氯乙酸根離子、三氯乙酸根離子、硝酸根離子、氯酸根離子、過氯酸根離子、溴酸根離子、碘酸根離子、草酸根離子、丙二酸根離子、甲基丙二酸根離子、乙基丙二酸根離子、丙基丙二酸根離子、丁基丙二酸根離子、二甲基丙二酸根離子、二乙基丙二酸根離子、琥珀酸根離子、甲基琥珀酸根離子、戊二酸根離子、己二酸根離子、伊康酸根離子、馬來酸根離子、富馬酸根離子、檸康酸根離子、檸檬酸根離子、碳酸根離子等。
式中,R
IA1表示碳數1~20之直鏈狀、分支狀或環狀之烷基、烯基、側氧基烷基或側氧基烯基、碳數6~20之取代或非取代之芳基、或碳數7~20之芳烷基或芳基側氧基烷基,該基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基、鹵素原子等取代。又,R
IA1與R
IA2亦可和它們所鍵結之碘原子一起形成環,形成環時,R
IA1、R
IA2各自表示碳數1~6之伸烷基。R
IA2為碳數1~20之直鏈狀、分支狀或環狀之伸烷基、伸烯基、碳數6~20之取代或非取代之伸芳基或伸芳烷基,該等基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基等取代。R
IA1、R
IA2也可在其鏈或環之中具有氧原子或氮原子。
式中,R
PA1、R
PA2、R
PA3各自表示碳數1~20之直鏈狀、分支狀或環狀之烷基、烯基、側氧基烷基或側氧基烯基、碳數6~20之取代或非取代之芳基、或碳數7~20之芳烷基或芳基側氧基烷基,該等基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基、鹵素原子等取代。又,R
PA1與R
PA2亦可和它們所鍵結之磷原子一起形成環,形成環時,R
PA1、R
PA2各自表示碳數1~6之伸烷基。R
PA4為碳數1~20之直鏈狀、分支狀或環狀之伸烷基、伸烯基、碳數6~20之取代或非取代之伸芳基或伸芳烷基,該等基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基等取代。R
PA1、R
PA2、R
PA3、R
PA4也可在其鏈或環之中具有氧原子或氮原子。
式中,R
NA1、R
NA2、R
NA3各自表示氫、碳數1~20之直鏈狀、分支狀或環狀之烷基、烯基、側氧基烷基或側氧基烯基、碳數6~20之取代或非取代之芳基、或碳數7~20之芳烷基或芳氧基烷基,為該等基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基等取代的1價有機基。又,R
NA1與R
NA2亦可和它們所鍵結之氮原子一起形成環,形成環時,R
NA1、R
NA2各自表示碳數1~6之伸烷基或含氮之環狀雜環、雜芳香環。R
NA4為碳數1~23之直鏈狀、分支狀或環狀之伸烷基、伸烯基、碳數6~29之取代或非取代之伸芳基、該等基之氫原子之一部分或全部亦可被烷氧基、胺基、烷基胺基等取代的2價有機基,R
NA1與R
NA2、R
NA1與R
NA4形成環狀結構且含有不飽和氮時,n
NA3=0,除此以外,n
NA3=1。
為了製造(Xc-10)而與上述(Xm-1)、(Xm-2)、(Xm-3)、(Xm-4)同時使用的水解性矽化合物,可例示上述通式(1)表示之矽化合物(A-1)與通式(2)表示之矽化合物(A-2)。
如此,可選擇所示之單體(Xm-1)、(Xm-2)、(Xm-3)、(Xm-4)中之1種以上、與水解性單體(A-1)、(A-2)中之任一者或兩者,並在反應前或反應中混合而製成形成(Xc-10)的反應原料。反應條件可為與熱硬化性含矽材料(Sx)之合成方法同樣之方法。
獲得之含矽之化合物(Xc-10)之分子量,不僅可藉由單體的選擇來調整,還可藉由控制聚合時的反應條件來調整,使用重量平均分子量超過100,000者的話,依情形有時會有異物產生、發生塗布不均的情況,宜使用100,000以下者,更佳為200~50,000,又更佳為300~30,000。此外,關於上述重量平均分子量的數據,係利用使用RI作為檢測器,並使用四氫呋喃作為溶離溶劑的凝膠滲透層析法(GPC),並使用聚苯乙烯作為標準物質,以聚苯乙烯換算來表示分子量。
此外,上述交聯觸媒(Xc-1)、(Xc-2)、(Xc-3)、(Xc-4)、(Xc-10)可單獨使用1種或將2種以上組合使用。交聯觸媒的添加量,相對於基礎聚合物(利用上述方法獲得之熱硬化性含矽材料(Sx))100質量份,宜為0.01~50質量份,更佳為0.1~40質量份。
[其他成分]
(有機酸)
為了改善本發明之含矽之阻劑下層膜形成用組成物的穩定性,宜添加碳數為1~30之1元或2元以上之有機酸。此時添加的酸可例示:甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、油酸、硬脂酸、亞麻油酸、次亞麻油酸、苯甲酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、水楊酸、三氟乙酸、單氯乙酸、二氯乙酸、三氯乙酸、草酸、丙二酸、甲基丙二酸、乙基丙二酸、丙基丙二酸、丁基丙二酸、二甲基丙二酸、二乙基丙二酸、琥珀酸、甲基琥珀酸、戊二酸、己二酸、伊康酸、馬來酸、富馬酸、檸康酸、檸檬酸等。尤其宜為草酸、馬來酸、甲酸、乙酸、丙酸、檸檬酸等。又,為了保持穩定性,亦可將2種以上之酸混合使用。添加量相對於含矽之阻劑下層膜形成用組成物中含有的矽100質量份,為0.001~25質量份,宜為0.01~15質量份,更佳為0.1~5質量份。
或也可摻合上述有機酸以使換算成含矽之阻劑下層膜形成用組成物之pH較佳成為0≦pH≦7,更佳成為0.3≦pH≦6.5,又更佳成為0.5≦pH≦6。
(水)
本發明中,亦可於含矽之阻劑下層膜形成用組成物中添加水。添加水的話,含矽之阻劑下層膜形成用組成物中之聚矽氧烷化合物進行水合,故微影性能改善。含矽之阻劑下層膜形成用組成物之溶劑成分中之水的含有率為超過0質量%且未達50質量%,尤其宜為0.3~30質量%,又更佳為0.5~20質量%。若為如此之範圍,含矽之阻劑下層膜之均勻性與微影性能係較佳,可抑制眼孔。
包含水之全部溶劑的使用量,相對於係基礎聚合物之聚矽氧烷化合物100質量份,宜為100~100,000質量份,尤其宜為200~50,000質量份。
(光酸產生劑)
本發明中,亦可於含矽之阻劑下層膜形成用組成物中添加光酸產生劑。本發明中使用之光酸產生劑,具體而言,可添加日本特開2009-126940號公報(0160)~(0179)段落記載之材料。
另外,本發明亦可含有1種或2種以上之下列通式(P-0)表示之於1分子中具有陰離子部與陽離子部的化合物(光酸產生劑)。
[化50]
上述式中,R
300為經1個以上之氟原子取代的2價有機基,R
301及R
302各自獨立地表示亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之1價烴基。R
303表示亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之2價烴基。又,R
301與R
302、或R
301與R
303亦可彼此鍵結並與式中之硫原子一起形成環。L
304表示單鍵、或亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之2價烴基。
如此之化合物(光酸產生劑),藉由與本發明之含矽之阻劑下層膜形成用組成物組合,可獲得能於保持上層阻劑之LWR之同時貢獻於剖面形狀之矩形化的阻劑下層膜。
上述通式(P-0)中,R
300為經1個以上之氟原子取代的2價有機基。上述2價有機基,例如表示碳數1~20之直鏈狀、分支狀或環狀之伸烷基、伸烯基、伸芳基等2價烴基。R
300具體而言可列舉下列結構。
此外,上述式中,(SO
3 -)係用以表示與上述通式(P-0)中之SO
3 -基之鍵結部位而記載。又,(R
350)係用以表示與上述通式(P-0)中之陽離子部介隔L
304而鍵結於R
300之部分的鍵結部位而記載。
R
301及R
302各自獨立地表示亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之1價烴基,例如表示烷基、烯基、側氧基烷基、芳基、芳烷基、芳基側氧基烷基。烷基可列舉:甲基、乙基、丙基、異丙基、正丁基、第二丁基、第三丁基、戊基、己基、庚基、辛基、環戊基、環己基、環庚基、環丙基甲基、4-甲基環己基、環己基甲基、降莰基、金剛烷基等。烯基可列舉:乙烯基、烯丙基、丙烯基、丁烯基、己烯基、環己烯基等。側氧基烷基可列舉:2-側氧基環戊基、2-側氧基環己基、2-側氧基丙基、2-側氧基乙基、2-環戊基-2-側氧基乙基、2-環己基-2-側氧基乙基、2-(4-甲基環己基)-2-側氧基乙基等。芳基可列舉:苯基、萘基、噻吩基等;4-羥基苯基、4-甲氧基苯基、3-甲氧基苯基、2-甲氧基苯基、4-乙氧基苯基、4-第三丁氧基苯基、3-第三丁氧基苯基等烷氧基苯基;2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙基苯基、4-第三丁基苯基、4-正丁基苯基、2,4-二甲基苯基等烷基苯基;甲基萘基、乙基萘基等烷基萘基;甲氧基萘基、乙氧基萘基、正丙氧基萘基、正丁氧基萘基等烷氧基萘基;二甲基萘基、二乙基萘基等二烷基萘基;二甲氧基萘基、二乙氧基萘基等二烷氧基萘基等。芳烷基可列舉:苄基、1-苯基乙基、2-苯基乙基等。芳基側氧基烷基可列舉:2-苯基-2-側氧基乙基、2-(1-萘基)-2-側氧基乙基、2-(2-萘基)-2-側氧基乙基等2-芳基-2-側氧基乙基等。又,R
301與R
302亦可彼此鍵結並與式中之硫原子一起形成環,此時,可列舉下式表示之基。
上述通式(P-0)中,R
303表示亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之2價烴基。R
303具體而言可列舉:亞甲基、伸乙基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基、庚烷-1,7-二基、辛烷-1,8-二基、壬烷-1,9-二基、癸烷-1,10-二基、十一烷-1,11-二基、十二烷-1,12-二基、十三烷-1,13-二基、十四烷-1,14-二基、十五烷-1,15-二基、十六烷-1,16-二基、十七烷-1,17-二基等直鏈狀烷二基;環戊烷二基、環己烷二基、降莰烷二基、金剛烷二基等飽和環狀烴基;伸苯基、伸萘基等不飽和環狀烴基。又,該等基之氫原子之一部分亦可被甲基、乙基、丙基、正丁基、第三丁基等烷基取代。或亦可置換為氧原子、硫原子、氮原子、鹵素原子之類的雜原子,其結果也可形成羥基、氰基、羰基、醚鍵、酯鍵、磺酸酯鍵、碳酸酯鍵、內酯環、磺內酯環、羧酸酐、鹵烷基等。又,R
301與R
303亦可彼此鍵結並與式中之硫原子一起形成環,此時,可列舉下式表示之基。
上述通式(P-0)中,L
304表示單鍵、或亦可經雜原子取代或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之2價烴基。L
304具體而言可列舉:亞甲基、伸乙基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基、庚烷-1,7-二基、辛烷-1,8-二基、壬烷-1,9-二基、癸烷-1,10-二基、十一烷-1,11-二基、十二烷-1,12-二基、十三烷-1,13-二基、十四烷-1,14-二基、十五烷-1,15-二基、十六烷-1,16-二基、十七烷-1,17-二基等直鏈狀烷二基;環戊烷二基、環己烷二基、降莰烷二基、金剛烷二基等飽和環狀烴基;伸苯基、伸萘基等不飽和環狀烴基。又,該等基之氫原子之一部分亦可被甲基、乙基、丙基、正丁基、第三丁基之類的烷基取代。或亦可置換為氧原子、硫原子、氮原子、鹵素原子之類的雜原子,其結果也可形成羥基、氰基、羰基、醚鍵、酯鍵、磺酸酯鍵、碳酸酯鍵、內酯環、磺內酯環、羧酸酐、鹵烷基等。
上述通式(P-0)表示之化合物(光酸產生劑),宜以下列通式(P-1)表示。
[化54]
上述通式(P-1)中,X
305、X
306各自獨立地表示氫原子、氟原子、三氟甲基中之任一者,但不全部為氫原子。n
307表示1~4之整數。R
301、R
302、R
303及L
304如上述。
上述通式(P-1-1)中,R
308、R
309及R
310各自獨立地表示氫原子、或亦可插入有雜原子的碳數1~20之直鏈狀、分支狀或環狀之1價烴基。具體而言可例示:甲基、乙基、丙基、異丙基、正丁基、第二丁基、第三丁基、第三戊基、正戊基、正己基、正辛基、正壬基、正癸基、環戊基、環己基、2-乙基己基、環戊基甲基、環戊基乙基、環戊基丁基、環己基甲基、環己基乙基、環己基丁基、降莰基、氧雜降莰基、三環[5.2.1.0
2,6]癸基、金剛烷基等。又,該等基之氫原子之一部分亦可置換為氧原子、硫原子、氮原子、鹵素原子之類的雜原子,亦可插入氧原子、硫原子、氮原子等雜原子,其結果也可形成或插入有羥基、氰基、羰基、醚鍵、酯鍵、磺酸酯鍵、碳酸酯鍵、內酯環、磺內酯環、羧酸酐、鹵烷基等。宜為甲基、甲氧基、第三丁基、第三丁氧基。
上述通式(P-1-1)中,n
308及n
309各自表示0~5之整數,宜為0或1。n
310表示0~4之整數,宜為0或2。L
304、X
305、X
306、n
307如上述。
上述通式(P-0)表示之化合物(光酸產生劑),又更佳以下列通式(P-1-2)表示。
[化56]
上述通式(P-1-2)中,A
311表示氫原子或三氟甲基。R
308、R
309、R
310、n
308、n
309、n
310、L
304如上述。
上述通式(P-0)、(P-1)、(P-1-1)及(P-1-2)表示之光酸產生劑,更具體而言可列舉下列所示之結構。惟,上述光酸產生劑不限定於該等。
上述通式(P-0)表示之化合物的添加量,相對於熱交聯性聚矽氧烷100質量份為0.001~40質量份,宜為0.1~40質量份,又更佳為0.1~20質量份。藉由添加如該等之光酸產生劑,可減少阻劑之曝光部的殘渣,並形成LWR小的圖案。
(穩定劑)
另外,本發明中,可於含矽之阻劑下層膜形成用組成物中添加穩定劑。就穩定劑可添加具有環狀醚作為取代基之1元或2元以上之醇。尤其添加日本特開2009-126940號公報(0181)~(0182)段落記載之穩定劑的話,可改善含矽之阻劑下層膜形成用組成物的穩定性。
(界面活性劑)
另外,本發明中,可視需要於含矽之阻劑下層膜形成用組成物中摻合界面活性劑。如此之界面活性劑,具體而言,可添加日本特開2009-126940號公報(0185)段落記載之材料。
(其他成分)
另外,本發明中,亦可視需要於含矽之阻劑下層膜形成用組成物中添加沸點為180度以上之高沸點溶劑。該高沸點溶劑可例示:1-辛醇、2-乙基己醇、1-壬醇、1-癸醇、1-十一醇、乙二醇、1,2-丙二醇、1,3-丁二醇、2,4-戊二醇、2-甲基-2,4-戊二醇、2,5-己二醇、2,4-庚二醇、2-乙基-1,3-己二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、甘油、γ-丁內酯、三丙二醇單甲醚、二丙酮醇、乙酸正壬酯、乙酸乙二醇單乙醚、1,2-二乙醯氧基乙烷、1-乙醯氧基-2-甲氧基乙烷、1,2-二乙醯氧基丙烷、乙酸二乙二醇單甲醚、乙酸二乙二醇單乙醚、乙酸二乙二醇單-正丁醚、乙酸丙二醇單甲醚、乙酸丙二醇單丙醚、乙酸丙二醇單丁醚、乙酸二丙二醇單甲醚、乙酸二丙二醇單乙醚等。
若為如上述說明的本發明之含矽之阻劑下層膜形成用組成物,會成為可形成無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性的阻劑下層膜的含矽之阻劑下層膜形成用組成物。
<圖案形成方法>
又,本發明提供一種圖案形成方法,係於被加工體上使用塗布型有機膜材料來形成有機下層膜,於該有機下層膜之上使用上述本發明之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜,於該含矽之阻劑下層膜上使用光阻劑組成物來形成光阻劑膜,將前述光阻劑膜進行曝光、顯影而形成阻劑圖案,將該形成有圖案之光阻劑膜作為遮罩,利用乾蝕刻對前述含矽之阻劑下層膜進行圖案轉印,將該轉印有圖案之含矽之阻劑下層膜作為遮罩,利用乾蝕刻對前述有機下層膜進行圖案轉印,進一步,將該轉印有圖案之有機下層膜作為遮罩,利用乾蝕刻將圖案轉印至前述被加工體。
另外,本發明提供一種圖案形成方法,係於被加工體上利用CVD法形成以碳作為主成分之硬遮罩,於該CVD硬遮罩之上使用上述本發明之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜,於該含矽之阻劑下層膜上使用光阻劑組成物來形成光阻劑膜,將前述光阻劑膜進行曝光、顯影而形成阻劑圖案,將該形成有圖案之光阻劑膜作為遮罩,利用乾蝕刻對前述含矽之阻劑下層膜進行圖案轉印,將該轉印有圖案之含矽之阻劑下層膜作為遮罩,利用乾蝕刻對前述CVD硬遮罩進行圖案轉印,進一步,將該轉印有圖案之CVD硬遮罩作為遮罩,利用乾蝕刻將圖案轉印至前述被加工體。
此處,被加工可使用半導體裝置基板、或於該半導體裝置基板上形成有金屬膜、合金膜、金屬碳化膜、金屬氧化膜、金屬氮化膜、金屬氧化碳化膜或金屬氧化氮化膜中之任一種膜者等。
半導體裝置基板一般使用矽基板,但並無特別限定,亦可使用Si、非晶矽(α-Si)、p-Si、SiO
2、SiN、SiON、W、TiN、Al等與被加工層不同材質者。
構成被加工體之金屬,可使用矽、鎵、鈦、鎢、鉿、鋯、鉻、鍺、銅、銀、金、銦、砷、鈀、鉭、銥、鋁、鐵、鉬、鈷或它們的合金。含有如此之金屬的被加工層,例如可使用Si、SiO
2、SiN、SiON、SiOC、p-Si、α-Si、TiN、WSi、BPSG、SOG、Cr、CrO、CrON、MoSi、W、Al、Cu、Al-Si等、或各種低介電膜、及其蝕刻阻擋膜,通常可形成50~10,000nm之厚度,尤其宜為100~5,000nm。
於被加工體上(含矽之阻劑下層膜之下)形成塗布型有機下層膜時,塗布型有機膜材料宜使用含有含芳香環之化合物者。使用如此之材料作為塗布型有機膜材料的話,可進一步抑制圖案崩塌的發生。又,使用包含含有具有直接與芳香環鍵結之羥基之重複單元的樹脂者更佳。
另一方面,於被加工體上(含矽之阻劑下層膜之下)形成CVD硬遮罩時,可利用CVD法形成以碳作為主成分之硬遮罩,也可利用習知的方法進行。
含矽之阻劑下層膜之形成,可藉由將本發明之含矽之阻劑下層膜形成用組成物利用旋塗法等塗布於被加工體上而進行。旋塗後,為了使溶劑蒸發而防止與光阻劑膜之混合,或為了促進交聯反應,宜進行烘烤。烘烤溫度宜為50~500℃之範圍內,烘烤時間宜為10~300秒之範圍內。亦取決於製造之器件的結構,但為了減少對器件之熱損傷,為400℃以下特佳。
本發明之圖案形成方法中,光阻劑膜材料只要是由化學增幅型光阻劑組成物構成者,則無特別限定。此外,本發明中,使用了鹼顯影液之正顯影、使用了有機溶劑之顯影液之負顯影均可採用,故配合顯影方法適當選擇正型光阻劑膜材料、負型光阻劑膜材料即可。
又,例如,本發明中之曝光步驟為利用ArF準分子雷射光所為之曝光處理時,就光阻劑膜材料而言,通常的ArF準分子雷射光用阻劑組成物均可使用。
如此之ArF準分子雷射光用阻劑組成物的多數候選者係習知,將習知的樹脂大致分類的話,有聚(甲基)丙烯酸系、COMA(Cyclo Olefin Maleic Anhydride)系、COMA-(甲基)丙烯酸混合系、ROMP(Ring Opening Metathesis Polymerization)系、聚降莰烯系等,其中,使用了聚(甲基)丙烯酸系樹脂的阻劑組成物,藉由於側鏈導入脂環族骨架而確保了蝕刻耐性,故解析性能比其他樹脂系更優異,可理想地使用。
本發明之圖案形成方法中,光阻劑膜中之阻劑圖案的形成,宜利用使用了波長為10nm以上300nm以下之光的微影、電子束所為之直接描繪、奈米壓印、或它們的組合來進行。又,阻劑圖案的形成,宜利用鹼顯影或有機溶劑顯影對阻劑圖案進行顯影。本發明之圖案形成方法中,可理想地使用如此之阻劑圖案的形成手段及顯影手段。
又,將形成於光阻劑膜之阻劑圖案利用乾蝕刻轉印至含矽之阻劑下層膜、有機下層膜或CVD硬遮罩、及被加工體時,利用習知的方法進行乾蝕刻即可。
若為如上述說明的本發明之圖案形成方法,於在含矽之阻劑下層膜之下形成塗布型有機下層膜或CVD硬遮罩的圖案形成方法中,無論負顯影、正顯影,均可抑制圖案崩塌的發生並形成微細圖案。
[實施例]
以下,利用合成例、實施例、及比較例具體地說明本發明,但本發明不限定於該等。此外,下列示例中%表示質量%。又,分子量測定係利用GPC進行。利用GPC獲得之聚苯乙烯換算之重量平均分子量記載為「Mw」,分散度記載為「Mw/Mn」。
<(1)矽化合物(A-1)之合成>
[合成例1-1]矽化合物(A-1-1)之合成
[化63]
於N
2環境下,將5-溴-2-羥基苯甲醇38.0g、乙基乙烯醚14.9g、四氫呋喃80g混合。加入對甲苯磺酸一水合物3.6g,升溫至40℃,並攪拌3小時。冷卻至室溫後,加入三乙胺2.1g,於室溫攪拌1小時。加入甲基異丁基酮150mL,進行水洗、減壓濃縮。將獲得之粗產物進行減壓蒸餾,以67℃/10Pa之餾分的形式獲得溴體(A-1-1-1)36.8g。
於N
2環境下,將鎂3.9g、四氫呋喃10g混合,升溫至60℃。緩慢滴加溴體(A-1-1-1)36.8g與四氫呋喃90g之混合液。於60℃攪拌1小時,冷卻至室溫,製備格氏試劑(A-1-1-2)。
於N
2環境下,將四甲氧基矽烷73.5g升溫至45℃,緩慢滴加上述製備之格氏試劑(A-1-1-2)。將反應液升溫至55℃,並攪拌2小時。冷卻至室溫後,實施過濾,並進行減壓濃縮。將獲得之粗產物進行減壓蒸餾,以92℃/20Pa之餾分的形式獲得矽化合物(A-1-1)16.5g。合成的矽化合物(A-1-1)之IR、1H NMR、13C NMR分析結果如下所示。
IR(D-ATR):
ν=2942、2841、1605、1577、1493、1405、1272、1254、1191、1156、1093、919、810、752、724、693cm
- 11H NMR(600 MHz,DMSO-d6)δ7.33(d,J=8.1 Hz,1H),7.25(s,1H),6.85(d,J=8.1 Hz,1H),5.28(q,J=5.1 Hz,1H),4.97(d,J=15.0 Hz,1H),4.83(d,J=15.0 Hz,1H),3.50(s,9H),1.43(d,J=5.1 Hz,3H)
13C NMR(600 MHz,DMSO-d6)δ154.7,134.1,131.8,121.0,120.6,115.9,96.9,65.6,50.3,20.4
[合成例1-2]矽化合物(A-1-2)之合成
[化64]
於N
2環境下,將5-溴-2-羥基苯甲醇101.5g、2,2-二甲氧基丙烷57.3g、丙酮200g混合。加入對甲苯磺酸一水合物9.5g,升溫至40℃,並攪拌3小時。冷卻至室溫後,加入三乙胺5.6g,於室溫攪拌1小時。加入甲基異丁基酮400mL,進行水洗、減壓濃縮。將獲得之粗產物進行減壓蒸餾,以73℃/20Pa之餾分的形式獲得溴體(A-1-2-1)80.0g。
於N
2環境下,將鎂8.0g、四氫呋喃20g混合,升溫至60℃。緩慢滴加溴體(A-1-2-1)80.0g與四氫呋喃180g之混合液。於60℃攪拌1小時,冷卻至室溫,製備格氏試劑(A-1-2-2)。
於N
2環境下,將四甲氧基矽烷150.2g升溫至45℃,緩慢滴加上述製備之格氏試劑(A-1-2-2)。將反應液升溫至55℃,並攪拌2小時。冷卻至室溫後,實施過濾,並進行減壓濃縮。將獲得之粗產物進行減壓蒸餾,以109℃/30Pa之餾分的形式獲得矽化合物(A-1-2)13.1g。合成的矽化合物(A-1-2)之IR、1H NMR、13C NMR分析結果如下所示。
IR(D-ATR):
ν=2943、2841、1605、1577、1493、1385、1374、1275、1200、1142、1103、956、912、812、737、724、686cm
-11H NMR(600 MHz,DMSO-d6)δ7.33(d,
J=8.4 Hz,1H),7.26(s,1H),6.81(d,
J=8.4 Hz,1H),4.83(s,2H),3.48(s,9H),1.46(s,6H)
13C NMR(600 MHz,DMSO-d6)δ153.0,134.1,131.6,119.9,119.5,116.3,99.6,59.9,50.3,24.6
<(2)熱硬化性含矽材料之合成>
使用上述矽化合物(A-1-1)~(A-1-2)與下列單體(A-2-0)~(A-2-14),如下述般合成熱硬化性含矽材料。
[合成例2-1]
於甲醇120g、10%硝酸0.1g及去離子水60g之混合物中,添加矽化合物(A-1-1):108.1g、單體(A-2-2):15.2g之混合物,於40℃保持12小時使其水解縮合。反應結束後,加入丙二醇單乙醚(PGEE)400g,將供至水解縮合之水分及副產物醇於減壓餾去,得到熱硬化性含矽材料2-1之PGEE溶液430g(化合物濃度20%)。測定其聚苯乙烯換算分子量,結果Mw=1,800。
[合成例2-2]~[合成例2-16]
以與合成例2-1同樣之條件,使用表1、2所示之單體,實施[合成例2-2]至[合成例2-16],分別獲得目的物。
[比較合成例2-1]
於甲醇120g、70%硝酸0.1g、及去離子水60g之混合物中,添加單體(A-2-0)5.0g、單體(A-2-1)3.4g、及單體(A-2-2)68.5g之混合物,於40℃保持12小時使其水解縮合。反應結束後,加入PGEE300g,將副產物醇及過剩的水於減壓餾去,得到聚矽氧烷化合物2-1之PGEE溶液160g(化合物濃度20%)。測定該聚矽氧烷化合物2-1之聚苯乙烯換算分子量,結果Mw=2,300。
[比較合成例2-2]
於甲醇120g、甲磺酸1g、及去離子水60g之混合物中,添加單體(A-2-1)13.6g、單體(A-2-2)38.1g、及單體(A-2-11)40.6g之混合物,於40℃保持12小時使其水解縮合。反應結束後,加入PGEE300g,將副產物醇及過剩的水於減壓餾去,得到聚矽氧烷化合物2-2之PGEE溶液260g(化合物濃度20%)。測定該聚矽氧烷化合物2-2之聚苯乙烯換算分子量,結果Mw=3,400。
[合成例3]
於甲醇120g、10%硝酸0.1g及去離子水60g之混合物中,添加單體(A-2-1):61.3g及單體(A-2-14):12.9g之混合物,於40℃保持12小時使其水解縮合。反應結束後,加入丙二醇單乙醚(PGEE)300g,將供至水解縮合之水分及副產物醇於減壓餾去,得到含銨鹽之聚矽氧烷化合物Z-1之PGEE溶液200g(化合物濃度20%)。測定該含銨鹽之聚矽氧烷化合物Z-1之聚苯乙烯換算分子量,結果Mw=1,500。
[表1]
合成例 | 反應原料 | Mw |
2-1 | 矽化合物(A-1-1):108.1g、 單體(A-2-2):15.2g | 1,800 |
2-2 | 矽化合物(A-1-2):71.1g、 單體(A-2-2):38.1g | 2,000 |
2-3 | 矽化合物(A-1-1):20.3g、 單體(A-2-1):6.8g、 單體(A-2-2):57.1g | 2,600 |
2-4 | 矽化合物(A-1-2):21.3g、 單體(A-2-1):6.8g、 單體(A-2-2):57.1g | 2,600 |
2-5 | 矽化合物(A-1-1):13.5g、 單體(A-2-0):5.0g、 單體(A-2-1):6.8g、 單體(A-2-2):57.1g | 2,500 |
2-6 | 矽化合物(A-1-2):14.2g、 單體(A-2-0):5.0g、 單體(A-2-1):6.8g、 單體(A-2-2):57.1g | 2,500 |
2-7 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-3):72.9g、 單體(A-2-4):11.8g | 2,200 |
2-8 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-3):72.9g、 單體(A-2-5):12.7g | 2,100 |
2-9 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-3):72.9g、 單體(A-2-6):13.9g | 2,400 |
2-10 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-3):72.9g、 單體(A-2-7):13.2g | 2,300 |
[表2]
合成例 | 反應原料 | Mw |
2-11 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-3):72.9g、 單體(A-2-8):14.5g | 2,200 |
2-12 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-2):53.3g、 單體(A-2-9):12.3g | 2,500 |
2-13 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-2):53.3g、 單體(A-2-10):10.2g | 2,400 |
2-14 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-2):53.3g、 單體(A-2-11):13.5g | 2,500 |
2-15 | 矽化合物(A-1-1):6.8g、 單體(A-2-0):5.0g、 單體(A-2-1):6.8g、 單體(A-2-2):53.3g、 單體(A-2-12):17.7g | 2,300 |
2-16 | 矽化合物(A-1-1):13.5g、 單體(A-2-1):6.8g、 單體(A-2-2):53.3g、 單體(A-2-13):16.0g | 2,400 |
比較2-1 | 單體(A-2-0):5.0g、 單體(A-2-1):3.4g、 單體(A-2-2):68.5g | 2,300 |
比較2-2 | 單體(A-2-1):13.6g、 單體(A-2-3):38.1g、 單體(A-2-11):40.6g | 3,400 |
單體(A-2-0):PhSi(OCH
3)
3單體(A-2-1):CH
3Si(OCH
3)
3單體(A-2-2):Si(OCH
3)
4單體(A-2-3):Si(OC
2H
5)
4
<實施例、比較例>[含矽之阻劑下層膜形成用組成物溶液之製備]
將上述合成例中獲得之聚矽氧烷(熱硬化性含矽材料:合成例2-1~16)、交聯觸媒或聚矽氧烷化合物Z-1、比較聚矽氧烷化合物2-1、2-2、光酸產生劑、酸、溶劑、水以表3-6所示之比例混合,利用0.1μm之氟樹脂製的過濾器進行過濾,藉此分別製備含矽之阻劑下層膜形成用組成物溶液,並分別定義為Sol.1~57。
[表3]
No. | 聚矽氧烷 | 交聯觸媒 | 光酸產生劑 | 酸 | 溶劑 | 水 |
(質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | |
Sol.1 | 合成例2-1(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.2 | 合成例2-2(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.3 | 合成例2-3(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.4 | 合成例2-3(1) | TPSMA | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.5 | 合成例2-3(1) | QMAMA | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.6 | 合成例2-3(1) | QMATFA | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.7 | 合成例2-3(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.8 | 合成例2-3(1) | QBANO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.9 | 合成例2-3(1) | Ph 2ICl | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.10 | 合成例2-3(1) | Z-1 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.11 | 合成例2-3(1) | TPSNO 3 | TPSNf | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (0.01) | (100) | |||
Sol.12 | 合成例2-3(1) | TPSNO 3 | TPSNf | 馬來酸 | PGEE(90) | 水(10) |
(0.01) | (0.01) | (0.01) | GBL(10) | |||
Sol.13 | 合成例2-3(1) | TPSNO 3 | PAG-1 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (0.01) | (100) | |||
Sol.14 | 合成例2-3(1) | QBANO 3 | TPSNf | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (0.01) | (100) | |||
Sol.15 | 合成例2-3(1) | QBANO 3 | TPSNf | 馬來酸 | PGEE(90) | 水(10) |
(0.01) | (0.01) | (0.01) | GBL(10) |
[表4]
No. | 聚矽氧烷 | 交聯觸媒 | 光酸產生劑 | 酸 | 溶劑 | 水 |
(質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | |
Sol.16 | 合成例2-4(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.17 | 合成例2-5(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.18 | 合成例2-6(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.19 | 合成例2-7(1) | QBANO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.20 | 合成例2-8(1) | QBANO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.21 | 合成例2-9(1) | TMPANO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.22 | 合成例2- | TMPANO 3 | 無 | 馬來酸 | PGEE | 水(10) |
10(1) | (0.01) | (0.01) | (100) | |||
Sol.23 | 合成例2- | TMPANO 3 | 無 | 馬來酸 | PGEE(90) | 水(10) |
11(1) | (0.01) | (0.01) | PGME(10) | |||
Sol.24 | 合成例2- | TMPANO 3 | PAG-1(0.01) | 馬來酸 | PGEE | 水(10) |
12(1) | (0.01) | (0.01) | (100) | |||
Sol.25 | 合成例2- | QBANO 3 | TPSNf(0.01) | 馬來酸 | PGEE(90) | 水(10) |
13(1) | (0.01) | (0.01) | DAA(10) | |||
Sol.26 | 合成例2- | QBANO 3 | PAG-1(0.01) | 馬來酸 | PGEE | 水(10) |
14(1) | (0.01) | (0.01) | (100) | |||
Sol.27 | 合成例2- | QBANO 3 | 無 | 馬來酸 | PGEE | 水(10) |
15(1) | (0.01) | (0.01) | (100) | |||
Sol.28 | 合成例2- | QBANO 3 | 無 | 馬來酸 | PGEE | 水(10) |
16(1) | (0.01) | (0.01) | (100) | |||
Sol.29 | 比較聚矽氧烷化合物2-1(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(10) |
(0.01) | (0.01) | (100) | ||||
Sol.30 | 合成例2-1(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.31 | 合成例2-2(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.32 | 合成例2-3(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) |
[表5]
No. | 聚矽氧烷 | 交聯觸媒 | 光酸產生劑 | 酸 | 溶劑 | 水 |
(質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | |
Sol.33 | 合成例2-3(1) | TPSMA | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.34 | 合成例2-3(1) | QMAMA | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.35 | 合成例2-3(1) | QMATFA | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.36 | 合成例2-3(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.37 | 合成例2-3(1) | QBANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.38 | 合成例2-3(1) | Ph 2ICl | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.39 | 合成例2-3(1) | Z-1 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.40 | 合成例2-3(1) | TPSNO 3 | TPSNf | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (0.01) | (300) | |||
Sol.41 | 合成例2-3(1) | TPSNO 3 | PAG-1 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (0.01) | (300) | |||
Sol.42 | 合成例2-3(1) | QBANO 3 | TPSNf | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (0.01) | (300) | |||
Sol.43 | 合成例2-4(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.44 | 合成例2-5(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.45 | 合成例2-6(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.46 | 合成例2-7(1) | QBANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.47 | 合成例2-8(1) | QBANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.48 | 合成例2-9(1) | TMPANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.49 | 合成例2- | TMPANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
10(1) | (0.01) | (0.01) | (300) | |||
Sol.50 | 合成例2- | TMPANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
11(1) | (0.01) | (0.01) | (300) |
[表6]
No. | 聚矽氧烷 | 交聯觸媒 | 光酸產生劑 | 酸 | 溶劑 | 水 |
(質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | |
Sol.51 | 合成例2- | TMPANO 3 | PAG-1 | 馬來酸 | PGEE | 水(30) |
12(1) | (0.01) | (0.01) | (0.01) | (300) | ||
Sol.52 | 合成例2- | QBANO 3 | TPSNf | 馬來酸 | PGEE | 水(30) |
13(1) | (0.01) | (0.01) | (0.01) | (300) | ||
Sol.53 | 合成例2- | QBANO 3 | PAG-1 | 馬來酸 | PGEE | 水(30) |
14(1) | (0.01) | (0.01) | (0.01) | (300) | ||
Sol.54 | 合成例2- | QBANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
15(1) | (0.01) | (0.01) | (300) | |||
Sol.55 | 合成例2- | QBANO 3 | 無 | 馬來酸 | PGEE | 水(30) |
16(1) | (0.01) | (0.01) | (300) | |||
Sol.56 | 比較聚矽氧烷化合物2-1(1) | TPSNO 3 | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) | ||||
Sol.57 | 比較聚矽氧烷化合物2-2(1) | TPSMA | 無 | 馬來酸 | PGEE | 水(30) |
(0.01) | (0.01) | (300) |
TPSNO
3:硝酸三苯基鋶
TPSMA :馬來酸單(三苯基鋶)
QMAMA :馬來酸單(四甲基銨)
QMATFA :三氟乙酸四甲基銨
QBANO
3:硝酸四丁基銨
Ph
2ICl :氯化二苯基錪
TMPANO
3:硝酸三甲基苯基銨
Z-1 :含有20%聚矽氧烷化合物Z-1之PGEE溶液
TPSNf :九氟丁烷磺酸三苯基鋶
PAG-1 :參照下式
[化66]
PGEE :丙二醇單乙醚
PGME :丙二醇單甲醚
GBL :γ-丁內酯
DAA :二丙酮醇
[利用ArF曝光、正顯影阻劑所為之試驗]
(圖案化試驗:實施例1-1~1-28、比較例1-1)
於矽晶圓上旋轉塗布下列含萘骨架之樹脂(UL聚合物1)組成物,於350℃加熱60秒,形成膜厚200nm之有機下層膜。於其上旋轉塗布含矽之阻劑下層膜形成用組成物溶液Sol.1~29,於240℃加熱60秒,分別形成膜厚35nm之含矽之阻劑下層膜Film1~29。
然後,於含矽之阻劑下層膜上塗布表7記載之正顯影用ArF光阻劑溶液(PR-1),於110℃烘烤60秒,形成膜厚100nm之光阻劑膜。進一步,於光阻劑膜上塗布表8記載之浸潤保護膜材料(TC-1),於90℃加熱60秒,形成膜厚50nm之保護膜。
然後,將該等利用ArF浸潤曝光裝置(Nikon(股)製;NSR-S610C,NA1.30、σ0.98/0.65、35度偶極偏光照明、6%半階度相位偏移遮罩)進行曝光,於100℃烘烤(PEB)60秒,以2.38質量%四甲基氫氧化銨(TMAH)水溶液顯影30秒,得到42nm1:1之正型線與間距圖案。之後,利用日立先端科技(股)製電子顯微鏡(CG4000)觀察顯影後之圖案崩塌,利用日立製作所(股)製電子顯微鏡(S-9380)觀察剖面形狀。其結果示於表9、10。
[表7]
PGMEA:丙二醇單甲醚乙酸酯
No. | ArF阻劑聚合物 (質量份) | 酸產生劑 (質量份) | 鹼 (質量份) | 撥水性聚合物 (質量份) | 溶劑 (質量份) |
PR-1 | P1 (100) | PAG-1 (10.0) | Q1 (4.25) | FP1 (4.0) | PGMEA(2,200) GBL(300) |
[表8]
No. | 聚合物 (質量份) | 有機溶劑 (質量份) |
TC-1 | 保護膜聚合物(100) | 二異戊醚(2700) 2-甲基-1-丁醇(270) |
[表9]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於42nm之圖案崩塌 |
實施例1-1 | Film1 | 垂直形狀 | 無 |
實施例1-2 | Film2 | 垂直形狀 | 無 |
實施例1-3 | Film3 | 垂直形狀 | 無 |
實施例1-4 | Film4 | 垂直形狀 | 無 |
實施例1-5 | Film5 | 垂直形狀 | 無 |
實施例1-6 | Film6 | 垂直形狀 | 無 |
實施例1-7 | Film7 | 垂直形狀 | 無 |
實施例1-8 | Film8 | 垂直形狀 | 無 |
實施例1-9 | Film9 | 垂直形狀 | 無 |
實施例1-10 | Film10 | 垂直形狀 | 無 |
實施例1-11 | Film11 | 垂直形狀 | 無 |
實施例1-12 | Film12 | 垂直形狀 | 無 |
實施例1-13 | Film13 | 垂直形狀 | 無 |
實施例1-14 | Film14 | 垂直形狀 | 無 |
實施例1-15 | Film15 | 垂直形狀 | 無 |
實施例1-16 | Film16 | 垂直形狀 | 無 |
實施例1-17 | Film17 | 垂直形狀 | 無 |
實施例1-18 | Film18 | 垂直形狀 | 無 |
實施例1-19 | Film19 | 垂直形狀 | 無 |
實施例1-20 | Film20 | 垂直形狀 | 無 |
實施例1-21 | Film21 | 垂直形狀 | 無 |
實施例1-22 | Film22 | 垂直形狀 | 無 |
[表10]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於42nm之圖案崩塌 |
實施例1-23 | Film23 | 垂直形狀 | 無 |
實施例1-24 | Film24 | 垂直形狀 | 無 |
實施例1-25 | Film25 | 垂直形狀 | 無 |
實施例1-26 | Film26 | 垂直形狀 | 無 |
實施例1-27 | Film27 | 垂直形狀 | 無 |
實施例1-28 | Film28 | 垂直形狀 | 無 |
比較例1-1 | Film29 | 因圖案崩塌而無法進行剖面觀察 | 於48nm發生崩塌 |
如表9、10所示,使用了本發明之含矽之阻劑下層膜形成用組成物的實施例1-1~1-28中,觀察到使用正顯影用光阻劑膜材料時,可獲得垂直形狀的圖案剖面,且沒有圖案崩塌。另一方面,未使用本發明之含矽之阻劑下層膜形成用組成物的比較例1-1中,於48nm發生圖案崩塌。
(圖案蝕刻試驗:實施例2-1~2-16)
將上述正型顯影所為之圖案化試驗(實施例1-1~1-3、1-16~1-28)中製作的阻劑圖案作為遮罩,以下列條件(1)進行乾蝕刻,將圖案轉印至含矽之阻劑下層膜,然後,以下列之條件(2)進行乾蝕刻,將圖案轉印至有機下層膜。利用上述電子顯微鏡觀察獲得之圖案的剖面形狀與圖案粗糙度。其結果示於表11。
(1)利用CHF
3/CF
4系氣體之蝕刻條件
裝置:東京威力科創(股)製乾蝕刻裝置Telius SP
蝕刻條件(1):
腔室壓力 10Pa
Upper/Lower RF功率500W/300W
CHF
3氣體流量 50mL/min
CF
4氣體流量 150mL/min
Ar氣體流量 100mL/min
處理時間 40sec
(2)利用O
2/N
2系氣體之蝕刻條件
裝置:東京威力科創(股)製乾蝕刻裝置Telius SP
蝕刻條件(2):
腔室壓力 2Pa
Upper/Lower RF功率1,000W/300W
O
2氣體流量 300mL/min
N
2氣體流量 100mL/min
Ar氣體流量 100mL/min
處理時間 30sec
[表11]
例 | 含矽之阻劑下層膜 | 乾蝕刻後有機下層膜之圖案剖面形狀 | 圖案粗糙度 |
實施例2-1 | Film1 | 垂直形狀 | 2.1nm |
實施例2-2 | Film2 | 垂直形狀 | 2.0nm |
實施例2-3 | Film3 | 垂直形狀 | 1.5nm |
實施例2-4 | Film16 | 垂直形狀 | 1.8nm |
實施例2-5 | Film17 | 垂直形狀 | 1.9nm |
實施例2-6 | Film18 | 垂直形狀 | 1.6nm |
實施例2-7 | Film19 | 垂直形狀 | 2.0nm |
實施例2-8 | Film20 | 垂直形狀 | 1.9nm |
實施例2-9 | Film21 | 垂直形狀 | 1.6nm |
實施例2-10 | Film22 | 垂直形狀 | 2.0nm |
實施例2-11 | Film23 | 垂直形狀 | 1.9nm |
實施例2-12 | Film24 | 垂直形狀 | 1.7nm |
實施例2-13 | Film25 | 垂直形狀 | 1.9nm |
實施例2-14 | Film26 | 垂直形狀 | 1.8nm |
實施例2-15 | Film27 | 垂直形狀 | 1.6nm |
實施例2-16 | Film28 | 垂直形狀 | 1.8nm |
如表11所示,觀察到使用本發明之含矽之阻劑下層膜形成用組成物的話,正型顯影後之阻劑圖案的剖面形狀良好,且有機下層膜加工後之圖案的剖面形狀及圖案粗糙度亦良好。
[利用ArF曝光、負顯影阻劑所為之試驗]
(圖案化試驗:實施例3-1~3-28、比較例2-1)
與上述使用了正型阻劑之圖案化試驗同樣,於矽晶圓上形成有機下層膜,然後,旋轉塗布含矽之阻劑下層膜形成用組成物溶液Sol.1~29,於240℃加熱60秒,形成膜厚35nm之含矽之阻劑下層膜Film1~29。
然後,於含矽之阻劑下層膜上塗布表12記載之負顯影用ArF光阻劑溶液(NR-1),於110℃烘烤60秒,形成膜厚100nm之光阻劑膜。
然後,將該等利用ArF浸潤曝光裝置(Nikon(股)製;NSR-S610C,NA1.30、σ0.98/0.65、35度偶極偏光照明、6%半階度相位偏移遮罩)進行曝光,於100℃烘烤(PEB)60秒,邊以30rpm旋轉邊從顯影噴嘴噴吐出作為顯影液之乙酸丁酯3秒,之後停止旋轉,進行浸置顯影27秒,以二異戊醚淋洗後進行旋乾,於100℃烘烤20秒,使淋洗溶劑蒸發。藉由該圖案化,獲得42nm1:1之負型線與間距圖案。利用日立先端科技(股)製電子顯微鏡(CG4000)觀察顯影後之圖案崩塌,利用日立製作所(股)製電子顯微鏡(S-9380)觀察剖面形狀。其結果示於表13、14。
[表12]
No. | ArF阻劑聚合物 (質量份) | 酸產生劑 (質量份) | 鹼 (質量份) | 撥水性聚合物 (質量份) | 溶劑 (質量份) |
NR-1 | P2 (100) | PAG3 (10.0) | Q2 (2.0) | FP1 (4.0) | PGMEA(2,200) GBL(300) |
[表13]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於42nm之圖案崩塌 |
實施例3-1 | Film1 | 垂直形狀 | 無 |
實施例3-2 | Film2 | 垂直形狀 | 無 |
實施例3-3 | Film3 | 垂直形狀 | 無 |
實施例3-4 | Film4 | 垂直形狀 | 無 |
實施例3-5 | Film5 | 垂直形狀 | 無 |
實施例3-6 | Film6 | 垂直形狀 | 無 |
實施例3-7 | Film7 | 垂直形狀 | 無 |
實施例3-8 | Film8 | 垂直形狀 | 無 |
實施例3-9 | Film9 | 垂直形狀 | 無 |
實施例3-10 | Film10 | 垂直形狀 | 無 |
實施例3-11 | Film11 | 垂直形狀 | 無 |
實施例3-12 | Film12 | 垂直形狀 | 無 |
實施例3-13 | Film13 | 垂直形狀 | 無 |
實施例3-14 | Film14 | 垂直形狀 | 無 |
實施例3-15 | Film15 | 垂直形狀 | 無 |
實施例3-16 | Film16 | 垂直形狀 | 無 |
實施例3-17 | Film17 | 垂直形狀 | 無 |
實施例3-18 | Film18 | 垂直形狀 | 無 |
實施例3-19 | Film19 | 垂直形狀 | 無 |
實施例3-20 | Film20 | 垂直形狀 | 無 |
實施例3-21 | Film21 | 垂直形狀 | 無 |
實施例3-22 | Film22 | 垂直形狀 | 無 |
[表14]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於42nm之圖案崩塌 |
實施例3-23 | Film23 | 垂直形狀 | 無 |
實施例3-24 | Film24 | 垂直形狀 | 無 |
實施例3-25 | Film25 | 垂直形狀 | 無 |
實施例3-26 | Film26 | 垂直形狀 | 無 |
實施例3-27 | Film27 | 垂直形狀 | 無 |
實施例3-28 | Film28 | 垂直形狀 | 無 |
比較例2-1 | Film29 | 因圖案崩塌而無法進行剖面觀察 | 於45nm發生崩塌 |
如表13、14所示,使用了本發明之含矽之阻劑下層膜形成用組成物的實施例3-1~3-28中,即使使用負顯影用光阻劑膜材料時,亦觀察到可獲得垂直形狀的圖案剖面,且沒有圖案崩塌。另一方面,未使用本發明之含矽之阻劑下層膜形成用組成物的比較例2-1中,於45nm發生圖案崩塌。
(圖案蝕刻試驗:實施例4-1~4-16)
將上述負型顯影所為之圖案化試驗(實施例3-1~3-3、3-16~3-28)中製作的阻劑圖案作為遮罩,與上述正顯影阻劑圖案的蝕刻試驗同樣,以上述條件(1)進行乾蝕刻,將圖案轉印至含矽之阻劑下層膜,然後以上述條件(2)進行乾蝕刻,將圖案轉印至有機下層膜。利用上述電子顯微鏡觀察獲得之圖案的剖面形狀與圖案粗糙度。其結果示於表15。
[表15]
例 | 含矽之阻劑下層膜 | 乾蝕刻後有機下層膜之圖案剖面形狀 | 圖案粗糙度 |
實施例4-1 | Film1 | 垂直形狀 | 2.0nm |
實施例4-2 | Film2 | 垂直形狀 | 1.9nm |
實施例4-3 | Film3 | 垂直形狀 | 1.6nm |
實施例4-4 | Film16 | 垂直形狀 | 1.8nm |
實施例4-5 | Film17 | 垂直形狀 | 2.0nm |
實施例4-6 | Film18 | 垂直形狀 | 1.9nm |
實施例4-7 | Film19 | 垂直形狀 | 2.1nm |
實施例4-8 | Film20 | 垂直形狀 | 1.6nm |
實施例4-9 | Film21 | 垂直形狀 | 1.7nm |
實施例4-10 | Film22 | 垂直形狀 | 2.1nm |
實施例4-11 | Film23 | 垂直形狀 | 1.8nm |
實施例4-12 | Film24 | 垂直形狀 | 1.9nm |
實施例4-13 | Film25 | 垂直形狀 | 2.0nm |
實施例4-14 | Film26 | 垂直形狀 | 1.8nm |
實施例4-15 | Film27 | 垂直形狀 | 1.9nm |
實施例4-16 | Film28 | 垂直形狀 | 1.7nm |
如表15所示,觀察到使用本發明之含矽之阻劑下層膜形成用組成物的話,負型顯影後之阻劑圖案的剖面形狀良好,且有機下層膜加工後之圖案的剖面形狀及圖案粗糙度亦良好。
[利用EUV曝光、正顯影阻劑所為之試驗]
(實施例5-1~5-26、比較例3-1)
於矽晶圓上塗布含矽之阻劑下層膜形成用組成物溶液Sol.30~56,於240℃加熱60秒,製作膜厚25nm之含矽膜Film30~56。
然後,於Film30~56上旋塗將下列成分以表16之比例溶解而成之光阻劑膜材料,使用加熱板於105℃預烘60秒,製作膜厚35nm之阻劑膜。將其使用ASML公司製EUV掃描曝光機NXE3300(NA0.33、σ0.9/0.6、四極照明、晶圓上尺寸為節距36nm之L/S圖案)進行曝光,在加熱板上於100℃進行60秒PEB,以2.38質量%TMAH水溶液顯影30秒,得到尺寸18nm之線。之後,利用日立先端科技(股)製的測長SEM(CG5000) 觀察顯影後之圖案崩塌,利用日立先端科技(股)製電子顯微鏡(S-4800)觀察剖面形狀。其結果示於表17、18。
[表16]
界面活性劑:3M公司製FC-4430
PGMEA:丙二醇單甲醚乙酸酯
CyHO:環己酮
PGME:丙二醇單甲醚
成分 | 聚合物 | 淬滅劑 | 增感劑 | 界面活性劑 | 有機溶劑 |
組成 (質量份) | (100) | (4.0) | (2.1) | (0.25) | PGMEA(400) CyHO(2000) PGME(100) |
[表17]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於18nm之圖案崩塌 |
實施例5-1 | Film30 | 垂直形狀 | 無 |
實施例5-2 | Film31 | 垂直形狀 | 無 |
實施例5-3 | Film32 | 垂直形狀 | 無 |
實施例5-4 | Film33 | 垂直形狀 | 無 |
實施例5-5 | Film34 | 垂直形狀 | 無 |
實施例5-6 | Film35 | 垂直形狀 | 無 |
實施例5-7 | Film36 | 垂直形狀 | 無 |
實施例5-8 | Film37 | 垂直形狀 | 無 |
實施例5-9 | Film38 | 垂直形狀 | 無 |
實施例5-10 | Film39 | 垂直形狀 | 無 |
實施例5-11 | Film40 | 垂直形狀 | 無 |
實施例5-12 | Film41 | 垂直形狀 | 無 |
實施例5-13 | Film42 | 垂直形狀 | 無 |
實施例5-14 | Film43 | 垂直形狀 | 無 |
實施例5-15 | Film44 | 垂直形狀 | 無 |
實施例5-16 | Film45 | 垂直形狀 | 無 |
實施例5-17 | Film46 | 垂直形狀 | 無 |
實施例5-18 | Film47 | 垂直形狀 | 無 |
實施例5-19 | Film48 | 垂直形狀 | 無 |
實施例5-20 | Film49 | 垂直形狀 | 無 |
實施例5-21 | Film50 | 垂直形狀 | 無 |
實施例5-22 | Film51 | 垂直形狀 | 無 |
[表18]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於18nm之圖案崩塌 |
實施例5-23 | Film52 | 垂直形狀 | 無 |
實施例5-24 | Film53 | 垂直形狀 | 無 |
實施例5-25 | Film54 | 垂直形狀 | 無 |
實施例5-26 | Film55 | 垂直形狀 | 無 |
比較例3-1 | Film56 | 因圖案崩塌而無法進行剖面觀察 | 於46nm發生崩塌 |
如表17、18所示,使用了本發明之含矽之阻劑下層膜形成用組成物的實施例5-1~5-26中,觀察到使用正顯影用光阻劑膜材料進行EUV曝光時,可獲得垂直形狀的圖案剖面,且沒有圖案崩塌。另一方面,未使用本發明之含矽之阻劑下層膜形成用組成物的比較例3-1中,於46nm發生圖案崩塌。
[利用EUV曝光、負顯影阻劑所為之試驗]
(實施例6-1~6-26、比較例4-1~4-2)
於矽晶圓上塗布含矽之阻劑下層膜形成用組成物溶液Sol.30~57,於240℃加熱60秒,製作膜厚25nm之含矽膜Film30~57。
然後,於Film30~57上旋塗將下列成分以表19之比例溶解而成之光阻劑膜材料,使用加熱板於105℃預烘60秒,製作膜厚60nm之光阻劑膜。表19中之PRP-E1示於表20,PAG-E1與Q-E1示於表21。將其使用ASML公司製EUV掃描曝光機NXE3300(NA0.33、σ0.9/0.6、四極照明、晶圓上尺寸為節距36nm之L/S圖案)進行曝光,在加熱板上於100℃進行60秒PEB,利用乙酸丁酯進行30秒顯影,獲得尺寸18nm之線。之後,利用日立先端科技(股)製的測長SEM(CG5000)觀察顯影後之圖案崩塌,利用日立先端科技(股)製電子顯微鏡(S-4800)觀察剖面形狀。其結果示於表22、23。
[表19]
界面活性劑:3M公司製FC-4430
基礎樹脂 (質量份) | 光酸產生劑 (質量份) | 鹼性化合物 (質量份) | 界面活性劑 (質量份) | 溶劑 (質量份) | |
PR-E1 | PRP-E1 (85) | PAG-E1 (15.0) | Q-E1 (0.3) | FC-4430 (0.1) | PGMEA(2800) CyHO(1400) |
[表22]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於18nm之圖案崩塌 |
實施例6-1 | Film30 | 垂直形狀 | 無 |
實施例6-2 | Film31 | 垂直形狀 | 無 |
實施例6-3 | Film32 | 垂直形狀 | 無 |
實施例6-4 | Film33 | 垂直形狀 | 無 |
實施例6-5 | Film34 | 垂直形狀 | 無 |
實施例6-6 | Film35 | 垂直形狀 | 無 |
實施例6-7 | Film36 | 垂直形狀 | 無 |
實施例6-8 | Film37 | 垂直形狀 | 無 |
實施例6-9 | Film38 | 垂直形狀 | 無 |
實施例6-10 | Film39 | 垂直形狀 | 無 |
實施例6-11 | Film40 | 垂直形狀 | 無 |
實施例6-12 | Film41 | 垂直形狀 | 無 |
實施例6-13 | Film42 | 垂直形狀 | 無 |
實施例6-14 | Film43 | 垂直形狀 | 無 |
實施例6-15 | Film44 | 垂直形狀 | 無 |
實施例6-16 | Film45 | 垂直形狀 | 無 |
實施例6-17 | Film46 | 垂直形狀 | 無 |
實施例6-18 | Film47 | 垂直形狀 | 無 |
實施例6-19 | Film48 | 垂直形狀 | 無 |
實施例6-20 | Film49 | 垂直形狀 | 無 |
實施例6-21 | Film50 | 垂直形狀 | 無 |
實施例6-22 | Film51 | 垂直形狀 | 無 |
[表23]
例 | 含矽之阻劑下層膜 | 顯影後圖案剖面形狀 | 於18nm之圖案崩塌 |
實施例6-23 | Film52 | 垂直形狀 | 無 |
實施例6-24 | Film53 | 垂直形狀 | 無 |
實施例6-25 | Film54 | 垂直形狀 | 無 |
實施例6-26 | Film55 | 垂直形狀 | 無 |
比較例4-1 | Film56 | 因圖案崩塌而無法進行剖面觀察 | 於45nm發生崩塌 |
比較例4-2 | Film57 | 因圖案崩塌而無法進行剖面觀察 | 於38nm發生崩塌 |
如表22、23所示,使用了本發明之含矽之阻劑下層膜形成用組成物的實施例6-1~6-26中,觀察到使用負顯影用光阻劑膜材料進行EUV曝光時,也可獲得垂直形狀的圖案剖面,且沒有圖案崩塌。另一方面,未使用本發明之含矽之阻劑下層膜形成用組成物的比較例4-1~4-2中,發生圖案崩塌。
由上述可知,藉由使用本發明之含矽之阻劑下層膜形成用組成物,可形成無論負顯影、正顯影,對於任何阻劑圖案均具良好之密接性,而且對於如EUV曝光之更微細的圖案亦具良好之密接性的含矽之阻劑下層膜。
此外,本發明不限定於上述實施形態。上述實施形態係例示,具有與本發明之專利申請範圍記載之技術思想實質相同的構成,且發揮同樣的作用效果者,均包含在本發明之技術範圍內。
Claims (13)
- 如請求項1或2之含矽之阻劑下層膜形成用組成物,更含有交聯觸媒。
- 如請求項3之含矽之阻劑下層膜形成用組成物,其中,該交聯觸媒係鋶鹽、錪鹽、鏻鹽、銨鹽、鹼金屬鹽、或具有鋶鹽、錪鹽、鏻鹽、及銨鹽中之任一者作為結構之一部分的聚矽氧烷。
- 一種圖案形成方法,其特徵為: 於被加工體上使用塗布型有機下層膜材料來形成有機下層膜, 於該有機下層膜之上使用如請求項1至6中任一項之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜, 於該含矽之阻劑下層膜上使用光阻劑組成物來形成光阻劑膜, 將該光阻劑膜進行曝光、顯影而形成阻劑圖案, 將該形成有圖案之光阻劑膜作為遮罩,利用乾蝕刻對該含矽之阻劑下層膜進行圖案轉印, 將該轉印有圖案之含矽之阻劑下層膜作為遮罩,利用乾蝕刻對該有機下層膜進行圖案轉印, 進一步,將該轉印有圖案之有機下層膜作為遮罩,利用乾蝕刻將圖案轉印至該被加工體。
- 一種圖案形成方法,其特徵為: 於被加工體上利用CVD法形成以碳作為主成分之硬遮罩, 於該CVD硬遮罩之上使用如請求項1至6中任一項之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜, 於該含矽之阻劑下層膜上使用光阻劑組成物來形成光阻劑膜, 將該光阻劑膜進行曝光、顯影而形成阻劑圖案, 將該形成有圖案之光阻劑膜作為遮罩,利用乾蝕刻對該含矽之阻劑下層膜進行圖案轉印, 將該轉印有圖案之含矽之阻劑下層膜作為遮罩,利用乾蝕刻對該CVD硬遮罩進行圖案轉印, 進一步,將該轉印有圖案之CVD硬遮罩作為遮罩,利用乾蝕刻將圖案轉印至該被加工體。
- 如請求項7或8之圖案形成方法,其中,該阻劑圖案的形成,係利用使用了波長為10nm以上300nm以下之光的微影、電子束所為之直接描繪、奈米壓印、或它們的組合來形成阻劑圖案。
- 如請求項7或8之圖案形成方法,其中,該阻劑圖案的形成,係利用鹼顯影或有機溶劑顯影對阻劑圖案進行顯影。
- 如請求項7或8之圖案形成方法,其中,該被加工體為半導體裝置基板、或於該半導體裝置基板上形成有金屬膜、合金膜、金屬碳化膜、金屬氧化膜、金屬氮化膜、金屬氧化碳化膜或金屬氧化氮化膜者。
- 如請求項7或8之圖案形成方法,其中,構成該被加工體之金屬為矽、鎵、鈦、鎢、鉿、鋯、鉻、鍺、銅、銀、金、銦、砷、鈀、鉭、銥、鋁、鐵、鉬、鈷或它們的合金。
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