TWI443128B - 倍半矽氧烷-氧化鈦混成聚合物 - Google Patents
倍半矽氧烷-氧化鈦混成聚合物 Download PDFInfo
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- TWI443128B TWI443128B TW95139723A TW95139723A TWI443128B TW I443128 B TWI443128 B TW I443128B TW 95139723 A TW95139723 A TW 95139723A TW 95139723 A TW95139723 A TW 95139723A TW I443128 B TWI443128 B TW I443128B
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- Prior art keywords
- polymer
- titanium oxide
- sesquiterpene
- group
- grams
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 175
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 title claims description 52
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 120
- 238000000034 method Methods 0.000 claims description 57
- 229930004725 sesquiterpene Natural products 0.000 claims description 48
- 150000004354 sesquiterpene derivatives Chemical class 0.000 claims description 43
- 238000000576 coating method Methods 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000011248 coating agent Substances 0.000 claims description 38
- 239000006117 anti-reflective coating Substances 0.000 claims description 37
- 238000004377 microelectronic Methods 0.000 claims description 27
- -1 sesquiterpene alkane Chemical class 0.000 claims description 24
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 23
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 229920002120 photoresistant polymer Polymers 0.000 claims description 17
- 239000000010 aprotic solvent Substances 0.000 claims description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 239000013067 intermediate product Substances 0.000 claims description 14
- 239000010936 titanium Substances 0.000 claims description 14
- 238000000206 photolithography Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 238000005530 etching Methods 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 70
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 59
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 53
- 239000007787 solid Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000010410 layer Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 229910010413 TiO 2 Inorganic materials 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 11
- 102100027370 Parathymosin Human genes 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 230000000873 masking effect Effects 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- 229910003087 TiOx Inorganic materials 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 230000008033 biological extinction Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 230000009977 dual effect Effects 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000003667 anti-reflective effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 239000003989 dielectric material Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000001459 lithography Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- HLLICFJUWSZHRJ-UHFFFAOYSA-N tioxidazole Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)SC2=C1 HLLICFJUWSZHRJ-UHFFFAOYSA-N 0.000 description 4
- JZHKIUBMQMDQRG-UHFFFAOYSA-N C(=C)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)OC)CCCCCCCC JZHKIUBMQMDQRG-UHFFFAOYSA-N 0.000 description 3
- JSGRIFNBTXDZQU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC JSGRIFNBTXDZQU-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- LBIHNTAFJVHBLJ-UHFFFAOYSA-N 3-(triethoxymethyl)undec-1-ene Chemical compound C(=C)C(C(OCC)(OCC)OCC)CCCCCCCC LBIHNTAFJVHBLJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- NYBRWTOMCMOBFI-UHFFFAOYSA-N C(=CCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(=CCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC NYBRWTOMCMOBFI-UHFFFAOYSA-N 0.000 description 2
- WMAZOIVUIWQRKU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC WMAZOIVUIWQRKU-UHFFFAOYSA-N 0.000 description 2
- PZKBIVOXIFYDRI-UHFFFAOYSA-N CC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound CC(C(OCC)(OCC)OCC)CCCCCCCC PZKBIVOXIFYDRI-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910000420 cerium oxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 238000012876 topography Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- ANBBCZAIOXDZPV-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methyldecane Chemical compound CC(C(OC)(OC)OC)CCCCCCCC ANBBCZAIOXDZPV-UHFFFAOYSA-N 0.000 description 1
- NCRNCSZWOOYBQF-UHFFFAOYSA-N 1,1-Dimethoxydecane Chemical compound CCCCCCCCCC(OC)OC NCRNCSZWOOYBQF-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SMLNDVNTPWRZJH-UHFFFAOYSA-N 1-chloro-4-(trimethoxymethyl)dodecane Chemical compound ClCCCC(C(OC)(OC)OC)CCCCCCCC SMLNDVNTPWRZJH-UHFFFAOYSA-N 0.000 description 1
- WLRWTEIAYJHXDW-UHFFFAOYSA-N 2,2,3,3,4,4,4a,5,5,6-decamethyl-6H-cyclopenta[b]pyran Chemical compound CC1C=C2C(C(C(C(O2)(C)C)(C)C)(C)C)(C1(C)C)C WLRWTEIAYJHXDW-UHFFFAOYSA-N 0.000 description 1
- GCZWJRLXIPVNLU-UHFFFAOYSA-N 2,2-dimethoxy-3-methylundecane Chemical compound CC(C(OC)(OC)C)CCCCCCCC GCZWJRLXIPVNLU-UHFFFAOYSA-N 0.000 description 1
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 1
- WZLRYEIJALOESF-UHFFFAOYSA-R 2-ethylhexane-1,3-diolate;hydron;titanium(4+) Chemical compound [H+].[H+].[H+].[H+].[Ti+4].CCCC([O-])C(CC)C[O-].CCCC([O-])C(CC)C[O-].CCCC([O-])C(CC)C[O-].CCCC([O-])C(CC)C[O-] WZLRYEIJALOESF-UHFFFAOYSA-R 0.000 description 1
- IIEWMRPKJCXTAD-UHFFFAOYSA-N 3-(trimethoxymethyl)undecane Chemical compound C(C)C(C(OC)(OC)OC)CCCCCCCC IIEWMRPKJCXTAD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SXPGQGNWEWPWQZ-UHFFFAOYSA-N 4-(triethoxymethyl)dodecan-1-amine Chemical compound NCCCC(C(OCC)(OCC)OCC)CCCCCCCC SXPGQGNWEWPWQZ-UHFFFAOYSA-N 0.000 description 1
- GNPSQUCXOBDIDY-UHFFFAOYSA-N 4-(trimethoxymethyl)dodecane Chemical compound C(CCCCCCC)C(C(OC)(OC)OC)CCC GNPSQUCXOBDIDY-UHFFFAOYSA-N 0.000 description 1
- YXFRBUCPZXPBFQ-UHFFFAOYSA-N C(=C)C(C(OC(C)C)(OC(C)C)OC(C)C)CCCCCCCC Chemical compound C(=C)C(C(OC(C)C)(OC(C)C)OC(C)C)CCCCCCCC YXFRBUCPZXPBFQ-UHFFFAOYSA-N 0.000 description 1
- VXLHENRCUVMBIR-UHFFFAOYSA-N C(=C)C(C(OC)(OC)C)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)C)CCCCCCCC VXLHENRCUVMBIR-UHFFFAOYSA-N 0.000 description 1
- CYOXKCUGRLNSCA-UHFFFAOYSA-N C(=C)C(C(OCC)(OCC)C)CCCCCCCC Chemical compound C(=C)C(C(OCC)(OCC)C)CCCCCCCC CYOXKCUGRLNSCA-UHFFFAOYSA-N 0.000 description 1
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- CKCQPWIKDYEWFL-UHFFFAOYSA-N C1(=CC=CC=C1)CCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)CCCC(C(OC)(OC)OC)CCCCCCCC CKCQPWIKDYEWFL-UHFFFAOYSA-N 0.000 description 1
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- SLOGEAQEBFCDKI-UHFFFAOYSA-N ClCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound ClCCC(C(OC)(OC)OC)CCCCCCCC SLOGEAQEBFCDKI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UNVWJAYEKZVDDL-UHFFFAOYSA-N N(C(=O)N)CCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound N(C(=O)N)CCCC(C(OC)(OC)OC)CCCCCCCC UNVWJAYEKZVDDL-UHFFFAOYSA-N 0.000 description 1
- XEEHRQPQNJOFIQ-UHFFFAOYSA-N N(C1=CC=CC=C1)CCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound N(C1=CC=CC=C1)CCCC(C(OC)(OC)OC)CCCCCCCC XEEHRQPQNJOFIQ-UHFFFAOYSA-N 0.000 description 1
- XJDCHDFUMGSEHD-UHFFFAOYSA-N NCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound NCCCC(C(OC)(OC)OC)CCCCCCCC XJDCHDFUMGSEHD-UHFFFAOYSA-N 0.000 description 1
- UAIIRSWVSPOAHZ-UHFFFAOYSA-N NCCNCCCC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound NCCNCCCC(C(OCC)(OCC)OCC)CCCCCCCC UAIIRSWVSPOAHZ-UHFFFAOYSA-N 0.000 description 1
- KHHGUUWIWBOGGW-UHFFFAOYSA-N O(C1=CC=CC=C1)CCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound O(C1=CC=CC=C1)CCCC(C(OC)(OC)OC)CCCCCCCC KHHGUUWIWBOGGW-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000012864 cross contamination Methods 0.000 description 1
- 125000004465 cycloalkenyloxy group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000002355 dual-layer Substances 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000005191 phase separation Methods 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
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/58—Metal-containing linkages
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Structural Engineering (AREA)
- Architecture (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Silicon Polymers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Formation Of Insulating Films (AREA)
- Paints Or Removers (AREA)
- Internal Circuitry In Semiconductor Integrated Circuit Devices (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73153605P | 2005-10-28 | 2005-10-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200722457A TW200722457A (en) | 2007-06-16 |
| TWI443128B true TWI443128B (zh) | 2014-07-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW95139723A TWI443128B (zh) | 2005-10-28 | 2006-10-27 | 倍半矽氧烷-氧化鈦混成聚合物 |
Country Status (7)
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|---|---|
| US (1) | US8865845B2 (enExample) |
| EP (1) | EP1943294B1 (enExample) |
| JP (1) | JP5464855B2 (enExample) |
| KR (1) | KR101322045B1 (enExample) |
| CN (1) | CN101300289B (enExample) |
| TW (1) | TWI443128B (enExample) |
| WO (1) | WO2007053396A2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101970540B (zh) * | 2008-03-05 | 2014-07-23 | 陶氏康宁公司 | 倍半硅氧烷树脂 |
| JP2010209288A (ja) * | 2009-03-12 | 2010-09-24 | Kagoshima Univ | 酸化チタンを含有する水溶性複合材料及びその製造方法 |
| JP5615620B2 (ja) * | 2010-08-09 | 2014-10-29 | 日東電工株式会社 | 金属酸化物粒子の製造方法 |
| CN101974028B (zh) * | 2010-09-28 | 2012-07-18 | 哈尔滨工业大学 | 含钛苯基半笼型倍半硅氧烷的制备方法 |
| CN102061111B (zh) * | 2010-10-27 | 2013-12-25 | 中山市旌旗纳米材料科技有限公司 | 自清洁陶瓷化纳米玻璃减反射涂料制造方法及其减反射膜制造方法 |
| US8258636B1 (en) * | 2011-05-17 | 2012-09-04 | Rohm And Haas Electronic Materials Llc | High refractive index curable liquid light emitting diode encapsulant formulation |
| US8257988B1 (en) * | 2011-05-17 | 2012-09-04 | Rohm And Haas Electronic Materials Llc | Method of making light emitting diodes |
| US8450445B2 (en) | 2011-08-17 | 2013-05-28 | Rohm And Haas Electronic Materials Llc | Light emitting diode manufacturing method |
| US8455607B2 (en) * | 2011-08-17 | 2013-06-04 | Rohm And Haas Electronic Materials Llc | Curable liquid composite light emitting diode encapsulant |
| US9070548B2 (en) | 2012-03-06 | 2015-06-30 | Rohm And Haas Electronic Materials Llc | Metal hardmask compositions |
| CN103013112A (zh) * | 2012-11-21 | 2013-04-03 | 无锡南理工科技发展有限公司 | 一种改性纳米二氧化钛/热固性树脂复合材料及其制备方法 |
| US9201305B2 (en) * | 2013-06-28 | 2015-12-01 | Az Electronic Materials (Luxembourg) S.A.R.L. | Spin-on compositions of soluble metal oxide carboxylates and methods of their use |
| WO2015037398A1 (ja) * | 2013-09-11 | 2015-03-19 | Jsr株式会社 | 多層レジストプロセス用無機膜形成組成物及びパターン形成方法 |
| US9006355B1 (en) | 2013-10-04 | 2015-04-14 | Burning Bush Group, Llc | High performance silicon-based compositions |
| EP4303283A3 (en) * | 2017-07-28 | 2024-02-28 | Avery Dennison Corporation | Pressure sensitive adhesives and articles with hyperbranched silsesquioxane core and methods of making the same |
| CN109265696B (zh) * | 2018-09-27 | 2021-08-20 | 佛山一宇卫士陶瓷材料有限公司 | 一种陶瓷减水剂的制备方法 |
| CN109867788A (zh) * | 2019-03-18 | 2019-06-11 | 台州学院 | 一种有机硅-二氧化钛复合材料的制备方法 |
| CN111004506B (zh) * | 2019-12-23 | 2023-03-10 | 哈尔滨工业大学 | 一种具有抗紫外辐照特性的改性氰酸酯树脂制备方法 |
| JP7605421B2 (ja) * | 2020-12-07 | 2024-12-24 | 株式会社ダイセル | チタン含有複合材料 |
| CN113445303A (zh) * | 2021-07-09 | 2021-09-28 | 广西五行材料科技有限公司 | 一种用于皮革、纺织品除甲醛杀菌的纳米材料及其制备方法 |
| CN115678494B (zh) * | 2022-09-09 | 2024-02-09 | 宁波聚力新材料科技有限公司 | 一种耐高温硅酮胶及其制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3615272A (en) | 1968-11-04 | 1971-10-26 | Dow Corning | Condensed soluble hydrogensilsesquioxane resin |
| US5100503A (en) | 1990-09-14 | 1992-03-31 | Ncr Corporation | Silica-based anti-reflective planarizing layer |
| US5484867A (en) * | 1993-08-12 | 1996-01-16 | The University Of Dayton | Process for preparation of polyhedral oligomeric silsesquioxanes and systhesis of polymers containing polyhedral oligomeric silsesqioxane group segments |
| JPH07331173A (ja) * | 1995-02-21 | 1995-12-19 | Toray Ind Inc | 光学材料形成用塗液組成物および光学材料 |
| US5973095A (en) | 1997-04-21 | 1999-10-26 | Alliedsignal, Inc. | Synthesis of hydrogensilsesquioxane and organohydridosiloxane resins |
| US6316167B1 (en) | 2000-01-10 | 2001-11-13 | International Business Machines Corporation | Tunabale vapor deposited materials as antireflective coatings, hardmasks and as combined antireflective coating/hardmasks and methods of fabrication thereof and application thereof |
| AU5600200A (en) | 1999-06-10 | 2001-01-02 | Allied-Signal Inc. | Spin-on-glass anti-reflective coatings for photolithography |
| US6268457B1 (en) | 1999-06-10 | 2001-07-31 | Allied Signal, Inc. | Spin-on glass anti-reflective coatings for photolithography |
| US6420088B1 (en) | 2000-06-23 | 2002-07-16 | International Business Machines Corporation | Antireflective silicon-containing compositions as hardmask layer |
| US6891237B1 (en) | 2000-06-27 | 2005-05-10 | Lucent Technologies Inc. | Organic semiconductor device having an active dielectric layer comprising silsesquioxanes |
| US20040048194A1 (en) | 2002-09-11 | 2004-03-11 | International Business Machines Corporation | Mehod for forming a tunable deep-ultraviolet dielectric antireflection layer for image transfer processing |
| TW593455B (en) | 2003-02-14 | 2004-06-21 | Chung Hwa Chemical Ind Works L | Polysilsesquioxane-metal alkoxide hybrid film material, its preparation and use |
| JP2005173552A (ja) | 2003-11-20 | 2005-06-30 | Tokyo Ohka Kogyo Co Ltd | リソグラフィー用下層膜形成材料およびこれを用いた配線形成方法 |
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2006
- 2006-10-25 JP JP2008537915A patent/JP5464855B2/ja not_active Expired - Fee Related
- 2006-10-25 WO PCT/US2006/041662 patent/WO2007053396A2/en not_active Ceased
- 2006-10-25 EP EP06817377.2A patent/EP1943294B1/en not_active Not-in-force
- 2006-10-25 US US12/091,811 patent/US8865845B2/en not_active Expired - Fee Related
- 2006-10-25 CN CN200680040434.8A patent/CN101300289B/zh not_active Expired - Fee Related
- 2006-10-25 KR KR1020087012622A patent/KR101322045B1/ko not_active Expired - Fee Related
- 2006-10-27 TW TW95139723A patent/TWI443128B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080058503A (ko) | 2008-06-25 |
| US20100221666A1 (en) | 2010-09-02 |
| WO2007053396A2 (en) | 2007-05-10 |
| WO2007053396A3 (en) | 2007-07-12 |
| JP5464855B2 (ja) | 2014-04-09 |
| EP1943294B1 (en) | 2013-09-18 |
| KR101322045B1 (ko) | 2013-10-25 |
| EP1943294A2 (en) | 2008-07-16 |
| CN101300289A (zh) | 2008-11-05 |
| JP2009513788A (ja) | 2009-04-02 |
| US8865845B2 (en) | 2014-10-21 |
| CN101300289B (zh) | 2012-07-25 |
| TW200722457A (en) | 2007-06-16 |
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