CN101072896A - 形成抗反射涂层的方法 - Google Patents
形成抗反射涂层的方法 Download PDFInfo
- Publication number
- CN101072896A CN101072896A CNA2005800419565A CN200580041956A CN101072896A CN 101072896 A CN101072896 A CN 101072896A CN A2005800419565 A CNA2005800419565 A CN A2005800419565A CN 200580041956 A CN200580041956 A CN 200580041956A CN 101072896 A CN101072896 A CN 101072896A
- Authority
- CN
- China
- Prior art keywords
- numerical value
- composition
- silsesquioxane resins
- electron device
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 38
- 239000006117 anti-reflective coating Substances 0.000 title abstract description 3
- 229920005989 resin Polymers 0.000 claims abstract description 76
- 239000011347 resin Substances 0.000 claims abstract description 76
- 125000004185 ester group Chemical group 0.000 claims abstract description 15
- 239000004721 Polyphenylene oxide Chemical group 0.000 claims abstract description 14
- 229920000570 polyether Chemical group 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 32
- 239000011248 coating agent Substances 0.000 claims description 31
- 238000000576 coating method Methods 0.000 claims description 31
- -1 propylidene methyl Chemical group 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- 229910008051 Si-OH Inorganic materials 0.000 claims description 6
- 229910006358 Si—OH Inorganic materials 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 230000003667 anti-reflective effect Effects 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 20
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 19
- 239000005052 trichlorosilane Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000005055 methyl trichlorosilane Substances 0.000 description 12
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 12
- 239000004810 polytetrafluoroethylene Substances 0.000 description 12
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 229920001903 high density polyethylene Polymers 0.000 description 11
- 239000004700 high-density polyethylene Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000000428 dust Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- UDZSFFMRRQZEFX-UHFFFAOYSA-N 2-(2-trichlorosilylethoxy)acetic acid Chemical compound C(=O)(O)COCC[Si](Cl)(Cl)Cl UDZSFFMRRQZEFX-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 102100021439 Cancer/testis antigen 62 Human genes 0.000 description 1
- 101710117701 Cancer/testis antigen 62 Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002053 acidogenic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
- C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
- C23C18/125—Process of deposition of the inorganic material
- C23C18/1295—Process of deposition of the inorganic material with after-treatment of the deposited inorganic material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
- C23C18/06—Coating on selected surface areas, e.g. using masks
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
- C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
- C23C18/1204—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material inorganic material, e.g. non-oxide and non-metallic such as sulfides, nitrides based compounds
- C23C18/122—Inorganic polymers, e.g. silanes, polysilazanes, polysiloxanes
-
- 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
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
- G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
- H01L21/02137—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC the material comprising alkyl silsesquioxane, e.g. MSQ
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
- H01L21/3122—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds
- H01L21/3124—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds layers comprising hydrogen silsesquioxane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24355—Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
- Y10T428/24446—Wrinkled, creased, crinkled or creped
- Y10T428/24455—Paper
- Y10T428/24463—Plural paper components
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Thermal Sciences (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Manufacturing & Machinery (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Structural Engineering (AREA)
- Health & Medical Sciences (AREA)
- Architecture (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Silicon Polymers (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Formation Of Insulating Films (AREA)
- Surface Treatment Of Optical Elements (AREA)
Abstract
一种在形成抗反射涂层中有用的倍半硅氧烷树脂,其通式为(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(0H)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q,其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.30,和m+n+p+q≈1。
Description
[0001]随着半导体工业中对更小特征尺寸的持续需求,最近出现了193mm光学平版印刷术作为生产具有低于100nm器件的技术。使用这种较短波长的光要求底部抗反射涂层(BARC)以降低在基底上的反射,并通过吸收穿过光致抗蚀剂的光,减弱光致抗蚀剂的摆动曲线。可商购的抗反射涂料(ARC)由有机和无机这两种材料组成。典型地,无机ARC(它显示出良好的抗蚀刻性)是CVD基材料,和具有极端形貌的所有综合的缺点。通过旋涂工艺施加有机ARC材料,且该材料具有优良的填充和平面化性能,但缺点是对有机光致抗蚀剂的蚀刻选择性差。因此,高度需求提供兼有无机和有机ARC材料的优点的材料。
[0002]本发明涉及对于193nm的光来说显示出抗反射的涂层性能的倍半硅氧烷树脂。可在除去阶段汽提这些抗反射涂层,且当储存时倍半硅氧烷树脂是稳定的。另外,作为193nm的ARC材料,在倍半硅氧烷树脂内存在氢化物基团对于所需的固化性能和汽提能力来说是必要的。
[0003]特别地,本发明涉及一种在电子器件上形成抗反射涂层的方法,该方法包括:
(A)施加ARC组合物到电子器件上,所述ARC组合物包括:
(i)具有下述通式的倍半硅氧烷树脂:
(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(OH)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q
其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.50,和m+n+p+q≈1;和
(ii)溶剂;和
(B)除去溶剂,并固化倍半硅氧烷树脂,从而在电子器件上形成抗反射涂层。
[0004]形成抗反射涂层可用的倍半硅氧烷树脂(i)的通式为:
(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(OH)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q
其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.30,和m+n+p+q≈1。或者,m的数值为0.10-0.50,n的数值为0.10-0.50,p的数值为0.10-0.70,q的数值为0.05-0.20。
[0005]R选自酯基和聚醚基。酯基是含有至少一个酯官能团的任何有机取代基。聚醚基是具有通过氧原子连接的烃单元的有机取代基,可用下述结构为代表,但不限于这些:Si-(CH2)a[O(CH2)b]cOR′,其中a=2-12;b=2-6;c=2-200;R′=H、烷基或其它有机基团。此处可用的酯基的实例是Si-(CH2)2-O-C(O)Me和Si-(CH2)2-C(O)-OMe。此处可用的聚醚基的实例是Si-(CH2)3-(OCH2CH2)7-OMe、Si-(CH2)3-(OCH2CH2)7-OH和Si-(CH2)3-(OCH2CH2)7-OAc。
[0006]倍半硅氧烷树脂可以是基本上充分地缩合或者可以仅仅部分缩合。当倍半硅氧烷树脂是部分缩合时,在倍半硅氧烷树脂内小于40mol%的单元应当含有Si-OH基团。较高含量的这些单元可能导致树脂不稳定并形成凝胶。典型地,在倍半硅氧烷树脂内6-38mol%的单元含有Si-OH基团。
[0007]倍半硅氧烷树脂的重均分子量(Mw)范围为500-400,000,和优选范围为500-100,000,或者700-10,000。
[0008]此处可用的倍半硅氧烷树脂可例举但不限于(PhSiO3/2)0.1-0.25(HSiO3/2)0.15-0.30(MeSiO3/2)0.25-0.55(RSiO3/2)0.05-0.20,R=-(CH2)2-OC(O)Me;(PhSiO3/2)0.1-0.25(HSiO3/2)0.15-0.30(MeSiO3/2)0.25-0.55(RSiO3/2)0.05-0.20,R=-(CH2)2-(OE)7-OH。
[0009]可通过本领域已知的方法生产倍半硅氧烷树脂。例如,可通过水解和缩合苯基三烷氧基硅烷、氢三烷氧基硅烷和甲基三烷氧基硅烷的混合物,生产倍半硅氧烷树脂。或者,可通过水解和缩合苯基三氯硅烷、氢三氯硅烷和甲基三氯硅烷来生产它们。
[0010]典型地在溶剂存在下生产倍半硅氧烷树脂。可在生产倍半硅氧烷树脂中使用不含有可参与该反应的官能团的任何合适的有机或者有机硅溶剂。通常基于溶剂和硅烷反应物的总重量,以40-98wt%,或者70-90wt%的用量使用溶剂。可以两相或者单相体系形式进行反应。
[0011]有用的有机溶剂可例举但不限于:饱和脂族烃,例如正戊烷、己烷、正庚烷和异辛烷;脂环族烃,例如环戊烷和环己烷;芳烃,例如苯、甲苯、二甲苯、1,3,5-三甲基苯;醚类,例如四氢呋喃、二烷、乙二醇二乙醚、乙二醇二甲醚;酮类,例如甲基异丁基酮(MIBK)和环己酮;卤素取代的烷烃,例如三氯乙烷;卤代芳烃,例如溴苯和氯苯;酯类,例如异丁酸异丁酯和丙酸丙酯。有用的有机硅溶剂可例举但不限于环状硅氧烷,例如八甲基环四硅氧烷和十甲基环五硅氧烷。可使用单一的溶剂或者可使用溶剂的混合物。
[0012]可在任何温度下进行生产倍半硅氧烷树脂的反应,只要它不引起显著胶凝或者引起倍半硅氧烷树脂固化即可。典型地,在范围为5℃-150℃的温度下进行反应,其中建议采用环境温度。
[0013]形成倍半硅氧烷树脂的时间取决于许多因素,例如温度,硅烷反应物的类型和用量,以及催化剂(若存在的话)的用量。典型地,反应时间为几分钟到几小时。本领域的技术人员能容易地确定完成反应所需的时间。
[0014]在完成反应之后,可任选地除去催化剂。除去催化剂的方法是本领域已知的,和包括中和、汽提或者水洗或其结合。催化剂尤其当在溶液内时可能负面影响有机硅树脂的寿命,因此建议除去它。
[0015]在制备倍半硅氧烷树脂的方法中,在反应完成之后,可在减压下从倍半硅氧烷树脂溶液中除去挥发物。这种挥发物包括醇副产物、过量的水、催化剂、盐酸(氯代硅烷路线)和溶剂。除去挥发物的方法是本领域已知的和包括例如蒸馏。
[0016]在生产倍半硅氧烷树脂的反应之后,可进行许多任选的步骤,以获得所需形式的倍半硅氧烷树脂。例如,可通过除去溶剂,以固体形式回收倍半硅氧烷树脂。除去溶剂的方法不是关键的,和许多方法是本领域已知的(例如,在加热和/或真空下蒸馏)。一旦以固体形式回收倍半硅氧烷树脂,则可任选地将树脂再溶解在相同或者另一溶剂中以供特定的应用。或者,对于最终产物来说,若想要除了反应所使用的溶剂以外的不同溶剂,则可通过添加第二种溶剂,并且例如借助蒸馏除去第一种溶剂,来进行溶剂交换。另外,可通过除去一些溶剂或者添加额外用量的溶剂,来调节在溶剂内的树脂浓度。
[0017]通过结合倍半硅氧烷树脂(i)与溶剂(ii),来生产ARC组合物。然后将ARC组合物施加到电子器件上,除去溶剂,并固化倍半硅氧烷树脂,从而产生抗反射涂层。
[0018]典型地,电子器件是半导体器件,例如拟用于制造半导体组件的硅基器件和砷化镓基器件。典型地,该器件包括至少一层半导体层和包括各种传导、半导或者绝缘材料的多层其它层。
[0019]此处可用的溶剂可以与生产倍半硅氧烷树脂所使用的溶剂相同或者不同。有用的溶剂(ii)尤其包括但不限于1-甲氧基-2-丙醇、丙二醇单甲基乙基乙酸酯(PGMEA)和环己酮。基于ARC组合物的总重量,ARC组合物典型地包括约10%-约99.9wt%的溶剂,或者80-95wt%。
[0020]ARC组合物可进一步包括固化催化剂。合适的固化催化剂包括无机酸、光致产酸剂和热致产酸剂。固化催化剂可例举但不限于硫酸(H2SO4)、(4-乙基硫苯基)甲基苯基三氟甲磺酸锍和2-萘基二苯基三氟甲磺酸锍。典型地,基于ARC组合物的总重量,固化催化剂以最多1000ppm,或者500ppm的用量存在。
[0021]施加ARC组合物到电子器件上的具体方法包括但不限于旋涂、浸涂、喷涂、流涂、筛网印刷和其它。优选的施加方法是旋涂。典型地,涂布牵涉在约2000RPM下旋转电子器件,并添加ARC组合物到旋转的电子器件的表面上。
[0022]除去溶剂,并固化倍半硅氧烷树脂,从而在电子器件上形成抗反射涂层。通过已知的方法,例如加热,或者在施加过程中通过旋转,除去溶剂。
[0023]固化通常包括加热涂布的电子器件到充足的温度下充足的持续时间,以导致固化。例如,可在80℃-450℃的温度下加热涂布的电子器件0.1-60分钟,或者150-275℃下0.5-5分钟,或者200℃-250℃下0.5-2分钟。可在固化步骤过程中使用任何加热方法。例如,可将涂布的电子器件置于石英管炉、对流烘箱内,或者使之静置在热板上。
[0024]为了保护在固化过程中倍半硅氧烷树脂避免与氧或者碳反应,可在惰性氛围下进行固化步骤。此处可用的惰性氛围包括但不限于氮气和氩气。“惰性”是指该环境含有小于50ppm和优选小于10ppm的氧气。进行固化和除去步骤时的压力不是关键的。典型地在大气压下进行固化步骤,但低于或者超大气压也可行。
[0025]一旦固化,则含有抗反射涂层的电子器件可在进一步的基底加工步骤例如光刻法中使用。当在光刻法中使用时,在抗反射涂层上形成抗蚀剂图像。形成抗蚀剂图像的方法包括(a)在抗反射涂层之上形成抗蚀剂组合物的膜;(b)成影像地曝光抗蚀剂膜于辐射线下,产生曝光膜;和(c)使曝光膜显影,产生图像。在采用波长为157nm-365nm的紫外辐射线或者波长为157nm或193nm的紫外辐射线成影像地曝光的抗蚀剂组合物的情况下,在电子器件上的抗反射涂层尤其有用。一旦在抗蚀剂膜内产生图像,则在抗反射涂层内蚀刻图案。可使用已知的蚀刻材料来除去抗反射涂层。可利用额外的步骤或者除去抗蚀剂膜和其余抗反射涂层,以产生具有所需结构的器件。
[0026]包括下述实施例,以说明本发明的优选实施方案。本领域的技术人员应当理解,在以下实施例中公开的技术代表本发明人发现在本发明的实践中作用良好的技术,因此可视为构成本发明实践的优选模式。然而,本领域的技术人员应当理解,鉴于本发明的公开内容,可在所公开的具体实施方案中作出许多变化,且在没有脱离本发明的精神和范围的情况下,仍然获得相同或者类似的结果。
实施例
树脂合成
实施例1:TPh 0.25TH 0.30TMe 0.40TX1 0.05,X1=-(CH2)2-OC(O)Me
在氮气下,将120g PGMEA、13.2g(0.0625mol)苯基三氯硅烷、10.2g(0.075mol)三氯硅烷、14.9g(0.1mol)甲基三氯硅烷和2.8g(0.0125mol)乙酰氧基乙基三氯硅烷的混合物转移到反应器中。在1小时的时间段内,将200g PGMEA和10g(0.555mol)水的溶液加入到三氯硅烷的溶液中。在20℃下搅拌另外1小时,使反应稠化。然后,在40℃下,通过旋转蒸发仪,浓缩树脂溶液到约10wt%。将约40g乙醇加入到树脂溶液中。再一次汽提溶液到约20wt%。再次取出烧瓶,并用额外的PGMEA稀释该溶液到10wt%。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例2:TPh 0.25TH 0.30TMe 0.40TX2 0.05,X2=-(CH2)2-C(O)OMe
在氮气下,将120g PGMEA、13.2g(0.0625mol)苯基三氯硅烷、10.2g(0.075mol)三氯硅烷、14.9g(0.1mol)甲基三氯硅烷和2.8g(0.0125mol)2-(羧甲氧基)乙基三氯硅烷的混合物转移到反应器中。在1小时的时间段内,将200g PGMEA和10g(0.555mol)水的溶液加入到三氯硅烷的溶液中。在20℃下搅拌另外1小时,使反应稠化。然后,在40℃下,通过旋转蒸发仪,浓缩树脂溶液到约10wt%。将约40g乙醇加入到树脂溶液中。再一次汽提溶液到约20wt%。再次取出烧瓶,并用额外的PGMEA稀释该溶液到10wt%。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例3:TPh 0.25TH 0.30TMe 0.25TX1 0.20,X1=-(CH2)2-OC(O)Me
在氮气下,将120g PGMEA、13.2g(0.0625mol)苯基三氯硅烷、11.5g(0.085mol)三氯硅烷、9.30g(0.0625mol)甲基三氯硅烷和11.1g(0.05mol)乙酰氧基乙基三氯硅烷的混合物转移到反应器中。在1小时的时间段内,将200g PGMEA和10g(0.555mol)水的溶液加入到三氯硅烷的溶液中。在20℃下搅拌另外1小时,使反应稠化。然后,在40℃下,通过旋转蒸发仪,浓缩树脂溶液到约10wt%。将约40g乙醇加入到树脂溶液中。再一次汽提溶液到约20wt%。再次取出烧瓶,并用额外的PGMEA稀释该溶液到10wt%。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例4:TPh 0.10TH 0.30TMe 0.55TX2 0.05,X2=-(CH2)2-C(O)OMe
在氮气下,将120g PGMEA、5.29g(0.025mol)苯基三氯硅烷、10.16g(0.075mol)三氯硅烷、20.55g(0.1375mol)甲基三氯硅烷和2.77g(0.0125mol)2-(羧甲氧基)乙基三氯硅烷的混合物转移到反应器中。在1小时的时间段内,将200g PGMEA和10g(0.555mol)水的溶液加入到三氯硅烷的溶液中。在20℃下搅拌另外1小时,使反应稠化。然后,在40℃下,通过旋转蒸发仪,浓缩树脂溶液到约10wt%。将约40g乙醇加入到树脂溶液中。再一次汽提溶液到约20wt%。再次取出烧瓶,并用额外的PGMEA稀释该溶液到10wt%。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例5:TPh 0.10TH 0.30TMe 0.50TX2 0.10,X2=-(CH2)2-C(O)OMe
在氮气下,将120g PGMEA、5.29g(0.025mol)苯基三氯硅烷、10.16g(0.075mol)三氯硅烷、18.69g(0.125mol)甲基三氯硅烷和5.54g(0.025mol)2-(羧甲氧基)乙基三氯硅烷的混合物转移到反应器中。在1小时的时间段内,将200g PGMEA和10g(0.555mol)水的溶液加入到三氯硅烷的溶液中。在20℃下搅拌另外1小时,使反应稠化。然后,在40℃下,通过旋转蒸发仪,浓缩树脂溶液到约10wt%。将约40g乙醇加入到树脂溶液中。再一次汽提溶液到约20wt%。再次取出烧瓶,并用额外的PGMEA稀释该溶液到10wt%。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例6:TPh 0.10TH 0.25TMe 0.55TX2 0.10,X2=-(CH2)2-C(O)OMe
在氮气下,将120g PGMEA、5.29g(0.025mol)苯基三氯硅烷、8.47g(0.075mol)三氯硅烷、20.55g(0.138mol)甲基三氯硅烷和5.54g(0.025mol)2-(羧甲氧基)乙基三氯硅烷的混合物转移到反应器中。在1小时的时间段内,将200g PGMEA和10g(0.555mol)水的溶液加入到三氯硅烷的溶液中。在20℃下搅拌另外1小时,使反应稠化。然后,在40℃下,通过旋转蒸发仪,浓缩树脂溶液到约10wt%。将约40g乙醇加入到树脂溶液中。再一次汽提溶液到约20wt%。再次取出烧瓶,并用额外的PGMEA稀释该溶液到10wt%。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例7:TPh 0.10TH 0.30TMe 0.525TX2 0.075,X2=-(CH2)2-C(O)OMe
在氮气下,将120g PGMEA、5.29g(0.025mol)苯基三氯硅烷、10.16g(0.075mol)三氯硅烷、19.62g(0.131mol)甲基三氯硅烷和4.15g(0.019mol)2-(羧甲氧基)乙基三氯硅烷的混合物转移到反应器中。在1小时的时间段内,将200g PGMEA和10g(0.555mol)水的溶液加入到三氯硅烷的溶液中。在20℃下搅拌另外1小时,使反应稠化。然后,在40℃下,通过旋转蒸发仪,浓缩树脂溶液到约10wt%。将约40g乙醇加入到树脂溶液中。再一次汽提溶液到约20wt%。再次取出烧瓶,并用额外的PGMEA稀释该溶液到10wt%。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例8:TPh 0.25TH 0.15TMe 0.45TX3 0.15,X3=-(CH2)2-(OE)7-OH
通过在20℃下共水解苯基三氯硅烷、三氯硅烷和甲基三氯硅烷,制备TPh 0.25TH 0.30TMe 0.45树脂的10%PGMEA溶液。将5.00g TPh 0.25TH 0.30TMe 0.45的10%PGMEA溶液和0.128g单烯丙基聚乙二醇(DP=7)混合到反应烧瓶内。在50℃下,使该混合物循环通过铂催化剂床18小时。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例9:TPh 0.25TH 0.10TMe 0.45TX3 0.20,X3=-(CH2)2-(OE)7-OH
通过在20℃下共水解苯基三氯硅烷、三氯硅烷和甲基三氯硅烷,制备TPh 0.25TH 0.30TMe 0.45树脂的10%PGMEA溶液。将145.00gTPh 0.25TH 0.30TMe 0.45的10%PGMEA溶液和15.6g单烯丙基聚乙二醇(DP=7)混合到反应烧瓶内。在50℃下,使该混合物循环通过铂催化剂床18小时。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例10:TPh 0.10TH 0.30TMe 0.55TX3 0.05,X3=-(CH2)2-(OE)7-OH
通过在20℃下共水解苯基三氯硅烷、三氯硅烷和甲基三氯硅烷,制备TPh 0.25TH 0.30TMe 0.45树脂的10%PGMEA溶液。将120.00g TPh 0.25TH 0.30TMe 0.45的10%PGMEA溶液和3.86g单烯丙基聚乙二醇(DP=7)混合到反应烧瓶内。在50℃下,使该混合物循环通过铂催化剂床18小时。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
实施例11:TPh 0.10TH 0.25TMe 0.60TX3 0.05,X3=-(CH2)2-(OE)7-OH
通过在20℃下共水解苯基三氯硅烷、三氯硅烷和甲基三氯硅烷,制备TPh 0.25TH 0.25TMe 0.60树脂的10%PGMEA溶液。接下来,将120.00gTPh 0.25TH 0.25TMe 0.60的10%PGMEA溶液和3.48g单烯丙基聚乙二醇(DP=7)混合到反应烧瓶内。在50℃下,使该混合物循环通过铂催化剂床18小时。过滤溶液通过0.20微米的PTFE过滤器,并储存在250ml HDPE瓶子内。
膜涂层和表征
在Karl Suss CT62旋涂器上加工在晶片上的膜涂层。使树脂PGMEA溶液首先过滤通过0.2微米的PTFE过滤器,然后旋涂在标准单面四英寸抛光的低电阻率晶片或者双面抛光的FTIR晶片上(旋转速度=2000rpm;加速度=5000,时间=20秒)。如表中所示,使用具有氮气吹扫的快速热加工(RTP)烘箱,在(200-250℃)的温度下固化膜90秒。使用J.A.Woollam椭圆计,测定膜厚、折射指数和k值。所记录的厚度值是9次测量的平均值。通过测量PGMEA保持(1分钟)以及漂洗之前和之后的膜厚变化(ΔTh,单位:埃),确定固化之后膜的抗PGMEA性;通过测量四甲基氢氧化铵(TMAH)保持(1分钟)以及漂洗之前和之后的膜厚变化(ΔTh,单位:埃),确定固化之后的抗TMAH性。使用水和二碘甲烷作为液体,测量接触角,以便利用Zisman方法,计算润湿的临界表面张力。用两种商业湿汽提溶液NE89和CC1,完全汽提由上述树脂制造的所有固化膜。结果在表1和表2中。
表1:评价TPhTHTMeTX(X=酯基)树脂
树脂实施例 | 烘烤温度℃ | Th埃 | 水接触角 | 表面能 | PGMEA之后的ΔTh(埃) | TMAH之后的ΔTh(埃) |
1 | 225225250250 | 2285227622662287 | 8586 | 33.6 | 12 | 1310 |
2 | 225225250250 | 2081208720382063 | 8789 | 152 | 4230 | |
3 | 250250 | 19301929 | 82 | 35.5 | 0 | 61 |
4 | 250250 | 20242041 | 49 | 34 | ||
5 | 250250 | 24872485 | 85 | 37.1 | 1 | 44 |
6 | 250250 | 21072118 | 92 | 30.9 | 42 | 34 |
7 | 250250 | 19081898 | 87.7 | 30.9 | 3 | 52 |
表2:评价TPhTHTMeTX′(X=PEO基团)树脂
树脂实施例 | 烘烤温度(℃) | Th(埃) | 水接触角 | 表面能 | PGMEA之后的ΔTh(埃) | TMAH之后的ΔTh(埃) |
8 | 250250 | 25422540 | n/a | n/a | 3 | 15 |
9 | 250250 | 23892394 | 74 | 38.9 | 7 | 19 |
10 | 250250 | 22902320 | 81.2 | 32 | 28 | 60 |
11 | 250250 | 21252186 | 83 | 31.3 | 46 | 47 |
Claims (26)
1.一种在电子器件上形成抗反射涂层的方法,该方法包括:
(A)施力ARC组合物到电子器件上,所述ARC组合物包括:
(i)具有下述通式的倍半硅氧烷树脂:
(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(OH)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q
其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.50,和m+n+p+q≈1;和
(ii)溶剂;和
(B)除去溶剂,并固化倍半硅氧烷树脂,从而在电子器件上形成抗反射涂层。
2.权利要求1的方法,其中m的数值为0.10-0.50,n的数值为0.10-0.50,p的数值为0.10-0.70,和q的数值为0.05-0.20。
3.权利要求1的方法,其中在倍半硅氧烷树脂内,小于40mol%的单元含有Si-OH基团。
4.权利要求1的方法,其中在倍半硅氧烷树脂内,6-38mol%的单元含有Si-OH基团。
5.权利要求1的方法,其中溶剂(ii)选自1-甲氧基-2-丙醇、亚丙基甲醚乙酸酯和环己酮。
6.权利要求1的方法,其中基于ARC组合物的重量,ARC组合物含有80-95wt%的溶剂。
7.权利要求1的方法,其中ARC组合物另外含有固化催化剂。
8.权利要求1的方法,其中通过旋涂施力ARC组合物。
9.权利要求1的方法,其中通过加热固化倍半硅氧烷树脂。
10.权利要求9的方法,其中通过在150℃-275℃范围内的温度下加热来固化倍半硅氧烷树脂。
11.权利要求1的方法,其中通过在200℃-250℃范围内的温度下加热来固化倍半硅氧烷树脂。
12.权利要求1的方法,其中通过在惰性氛围下加热来固化倍半硅氧烷树脂。
13.一种在电子器件上形成抗反射涂层的方法,该方法包括:
(A)施加ARC组合物到电子器件上,所述ARC组合物包括:
(i)具有下述通式的倍半硅氧烷树脂:(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(OH)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q
其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.50,和m+n+p+q≈1;和
(ii)溶剂;
(B)除去溶剂,并固化倍半硅氧烷树脂,从而在电子器件上形成抗反射涂层;和
(C)在抗反射涂层上形成抗蚀剂图像。
14.权利要求13的方法,其中通过以下步骤形成抗蚀剂图像:
(a)在抗反射涂层之上形成抗蚀剂组合物的膜;
(b)成影像地曝光抗蚀剂膜于辐射线下,产生曝光膜;
(c)使曝光膜显影,产生图像。
15.一种在电子器件上形成抗反射涂层的方法,该方法包括:
(A)施加ARC组合物到电子器件上,所述ARC组合物包括:
(i)具有下述通式的倍半硅氧烷树脂:(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(OH)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q
其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.50,和m+n+p+q≈1;和
(ii)溶剂;
(B)除去溶剂,并固化倍半硅氧烷树脂,从而在电子器件上形成抗反射涂层;
(C)在抗反射涂层上形成抗蚀剂图像;和
(D)在抗反射膜内蚀刻图案。
16.一种在电子器件上形成抗反射涂层的方法,该方法包括:
(A)施力ARC组合物到电子器件上,所述ARC组合物包括:
(i)具有下述通式的倍半硅氧烷树脂:(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(OH)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q
其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.50,和m+n+p+q≈1;和
(ii)溶剂;
(B)除去溶剂,并固化倍半硅氧烷树脂,从而在电子器件上形成抗反射涂层;
(C)在抗反射涂层上形成抗蚀剂图像;
(D)在抗反射膜内蚀刻图案;和
(E)除去抗蚀剂图像和抗反射膜。
17.一种ARC组合物,它包括:
(i)具有下述通式的倍半硅氧烷树脂:(PhSiO(3-x)/2(OH)x)mHSiO(3-x)/2(OH)x)n(MeSiO(3-x)/2(OH)x)p(RSiO(3-x)/2(OH)x)q
其中Ph是苯基,Me是甲基,R选自酯基和聚醚基,x的数值为0、1或2;m的数值为0.05-0.95,n的数值为0.05-0.95,p的数值为0.05-0.95,q的数值为0.01-0.50,和m+n+p+q≈1;和
(ii)溶剂。
18.权利要求17的组合物,其中m的数值为0.10-0.50,n的数值为0.10-0.50,p的数值为0.10-0.70,和q的数值为0.05-0.20。
19.权利要求17的组合物,其中在倍半硅氧烷树脂内,小于40mol%的单元含有Si-OH基团。
20.权利要求17的组合物,其中在倍半硅氧烷树脂内,6-38mol%的单元含有Si-OH基团。
21.权利要求17的组合物,其中溶剂(ii)选自1-甲氧基-2-丙醇、亚丙基甲醚乙酸酯和环己酮。
22.权利要求17的组合物,其中基于ARC组合物的重量,ARC组合物含有80-95wt%的溶剂。
23.权利要求17的组合物,其中ARC组合物另外含有固化催化剂。
24.权利要求17的组合物,其中R是酯基,和该酯基是含有至少一个酯官能团的任何有机取代基。
25.权利要求17的组合物,其中R是聚醚基,和该聚醚基是具有通过氧原子连接的烃单元的有机取代基。
26.权利要求25的组合物,其中聚醚基的结构为Si-(CH2)a[O(CH2)b]cOR′,其中a=2-12;b=2-6;c=2-200;R′选自H、烷基或有机基团。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US63689704P | 2004-12-17 | 2004-12-17 | |
US60/636,897 | 2004-12-17 | ||
PCT/US2005/035236 WO2006065321A1 (en) | 2004-12-17 | 2005-09-29 | Method for forming anti-reflective coating |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101072896A true CN101072896A (zh) | 2007-11-14 |
CN101072896B CN101072896B (zh) | 2010-05-05 |
Family
ID=35645696
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2005800419565A Expired - Fee Related CN101072896B (zh) | 2004-12-17 | 2005-09-29 | 形成抗反射涂层的方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7833696B2 (zh) |
EP (1) | EP1819844B1 (zh) |
JP (1) | JP4688882B2 (zh) |
KR (1) | KR101275649B1 (zh) |
CN (1) | CN101072896B (zh) |
AT (1) | ATE400672T1 (zh) |
DE (1) | DE602005008100D1 (zh) |
TW (1) | TWI372946B (zh) |
WO (1) | WO2006065321A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102245722A (zh) * | 2008-12-10 | 2011-11-16 | 陶氏康宁公司 | 可转换的抗反射涂层 |
CN101624447B (zh) * | 2008-07-09 | 2012-11-21 | 三星移动显示器株式会社 | 聚倍半硅氧烷共聚物及其制造方法、聚倍半硅氧烷共聚物薄膜和有机发光二极管显示装置 |
TWI490655B (zh) * | 2008-12-10 | 2015-07-01 | Dow Corning | 倍半矽氧烷樹脂 |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7756384B2 (en) | 2004-11-08 | 2010-07-13 | Dow Corning Corporation | Method for forming anti-reflective coating |
EP1825330B1 (en) | 2004-12-17 | 2019-04-24 | Dow Silicones Corporation | Method for forming anti-reflective coating |
CN101133364B (zh) * | 2005-03-01 | 2013-03-20 | Jsr株式会社 | 抗蚀剂下层膜用组合物及其制造方法 |
KR101324052B1 (ko) | 2006-02-13 | 2013-11-01 | 다우 코닝 코포레이션 | 반사방지 코팅 재료 |
WO2007094849A2 (en) * | 2006-02-13 | 2007-08-23 | Dow Corning Corporation | Antireflective coating material |
US7704670B2 (en) | 2006-06-22 | 2010-04-27 | Az Electronic Materials Usa Corp. | High silicon-content thin film thermosets |
JP5115099B2 (ja) * | 2006-09-04 | 2013-01-09 | 東レ・ファインケミカル株式会社 | アシロキシ基を有するシリコーン共重合体及びその製造方法 |
JP5000250B2 (ja) | 2006-09-29 | 2012-08-15 | 東京応化工業株式会社 | パターン形成方法 |
US7736837B2 (en) | 2007-02-20 | 2010-06-15 | Az Electronic Materials Usa Corp. | Antireflective coating composition based on silicon polymer |
US8026040B2 (en) * | 2007-02-20 | 2011-09-27 | Az Electronic Materials Usa Corp. | Silicone coating composition |
KR20090114476A (ko) * | 2007-02-26 | 2009-11-03 | 에이제트 일렉트로닉 머트리얼즈 유에스에이 코프. | 실록산 중합체의 제조 방법 |
US8524441B2 (en) | 2007-02-27 | 2013-09-03 | Az Electronic Materials Usa Corp. | Silicon-based antireflective coating compositions |
US8026035B2 (en) * | 2007-03-30 | 2011-09-27 | Cheil Industries, Inc. | Etch-resistant disilane and saturated hydrocarbon bridged silicon-containing polymers, method of making the same, and method of using the same |
US8653217B2 (en) | 2007-05-01 | 2014-02-18 | Dow Corning Corporation | Method for forming anti-reflective coating |
US9023433B2 (en) | 2008-01-15 | 2015-05-05 | Dow Corning Corporation | Silsesquioxane resins and method of using them to form an antireflective coating |
CN101990551B (zh) * | 2008-03-04 | 2012-10-03 | 陶氏康宁公司 | 倍半硅氧烷树脂 |
KR101541939B1 (ko) * | 2008-03-05 | 2015-08-04 | 다우 코닝 코포레이션 | 실세스퀴옥산 수지 |
US20090253080A1 (en) * | 2008-04-02 | 2009-10-08 | Dammel Ralph R | Photoresist Image-Forming Process Using Double Patterning |
US20100040838A1 (en) * | 2008-08-15 | 2010-02-18 | Abdallah David J | Hardmask Process for Forming a Reverse Tone Image |
KR20110096155A (ko) * | 2008-12-10 | 2011-08-29 | 다우 코닝 코포레이션 | 습식 에칭가능한 반사방지 코팅 |
US8084186B2 (en) * | 2009-02-10 | 2011-12-27 | Az Electronic Materials Usa Corp. | Hardmask process for forming a reverse tone image using polysilazane |
CN103996457B (zh) * | 2014-05-29 | 2018-11-20 | 京东方科技集团股份有限公司 | 银纳米线薄膜及其制备方法、阵列基板、显示装置 |
KR102395936B1 (ko) * | 2016-06-16 | 2022-05-11 | 다우 실리콘즈 코포레이션 | 규소-풍부 실세스퀴옥산 수지 |
WO2023053988A1 (ja) * | 2021-09-28 | 2023-04-06 | 株式会社カネカ | 重合体及び硬化性組成物 |
WO2024006254A2 (en) * | 2022-06-28 | 2024-01-04 | Bowling Green State University | Tri-cure hybrid organo-silicon coatings |
Family Cites Families (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4587138A (en) | 1984-11-09 | 1986-05-06 | Intel Corporation | MOS rear end processing |
US5010159A (en) | 1989-09-01 | 1991-04-23 | Dow Corning Corporation | Process for the synthesis of soluble, condensed hydridosilicon resins containing low levels of silanol |
US5100503A (en) | 1990-09-14 | 1992-03-31 | Ncr Corporation | Silica-based anti-reflective planarizing layer |
US5210168A (en) | 1992-04-02 | 1993-05-11 | Dow Corning Corporation | Process for forming siloxane bonds |
EP0568476B1 (en) | 1992-04-30 | 1995-10-11 | International Business Machines Corporation | Silicon-containing positive resist and method of using the same in thin film packaging technology |
JPH0656560A (ja) | 1992-08-10 | 1994-03-01 | Sony Corp | Sog組成物及びそれを用いた半導体装置の製造方法 |
US5441765A (en) | 1993-09-22 | 1995-08-15 | Dow Corning Corporation | Method of forming Si-O containing coatings |
JP3499032B2 (ja) | 1995-02-02 | 2004-02-23 | ダウ コーニング アジア株式会社 | 放射線硬化性組成物、その硬化方法及びパターン形成方法 |
JP3324360B2 (ja) | 1995-09-25 | 2002-09-17 | 信越化学工業株式会社 | ポリシロキサン化合物及びポジ型レジスト材料 |
JPH09124794A (ja) | 1995-11-06 | 1997-05-13 | Dow Corning Asia Ltd | 有機光機能材を含有するポリシロキサン樹脂組成物及びそれから得られる透明な光機能素子 |
JP3192947B2 (ja) | 1995-11-16 | 2001-07-30 | 東京応化工業株式会社 | シリカ系被膜形成用塗布液の製造方法 |
US6057239A (en) | 1997-12-17 | 2000-05-02 | Advanced Micro Devices, Inc. | Dual damascene process using sacrificial spin-on materials |
US6344284B1 (en) | 1998-04-10 | 2002-02-05 | Organic Display Technology | Organic electroluminescent materials and devices made from such materials |
US6156640A (en) | 1998-07-14 | 2000-12-05 | United Microelectronics Corp. | Damascene process with anti-reflection coating |
US6087064A (en) * | 1998-09-03 | 2000-07-11 | International Business Machines Corporation | Silsesquioxane polymers, method of synthesis, photoresist composition, and multilayer lithographic method |
US6177143B1 (en) * | 1999-01-06 | 2001-01-23 | Allied Signal Inc | Electron beam treatment of siloxane resins |
US6461955B1 (en) | 1999-04-29 | 2002-10-08 | Texas Instruments Incorporated | Yield improvement of dual damascene fabrication through oxide filling |
US6281285B1 (en) | 1999-06-09 | 2001-08-28 | Dow Corning Corporation | Silicone resins and process for synthesis |
US6824879B2 (en) | 1999-06-10 | 2004-11-30 | Honeywell International Inc. | Spin-on-glass anti-reflective coatings for photolithography |
WO2000077575A1 (en) | 1999-06-10 | 2000-12-21 | Alliedsignal 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 |
US6890448B2 (en) | 1999-06-11 | 2005-05-10 | Shipley Company, L.L.C. | Antireflective hard mask compositions |
US6329118B1 (en) | 1999-06-21 | 2001-12-11 | Intel Corporation | Method for patterning dual damascene interconnects using a sacrificial light absorbing material |
JP2001093824A (ja) * | 1999-09-27 | 2001-04-06 | Shin Etsu Chem Co Ltd | レジスト下層用組成物及びパターン形成方法 |
US6982006B1 (en) | 1999-10-19 | 2006-01-03 | Boyers David G | Method and apparatus for treating a substrate with an ozone-solvent solution |
US6359096B1 (en) | 1999-10-25 | 2002-03-19 | Dow Corning Corporation | Silicone resin compositions having good solution solubility and stability |
KR100355604B1 (ko) | 1999-12-23 | 2002-10-12 | 주식회사 하이닉스반도체 | 난반사 방지막용 중합체와 그 제조방법 |
JP3795333B2 (ja) | 2000-03-30 | 2006-07-12 | 東京応化工業株式会社 | 反射防止膜形成用組成物 |
US6420088B1 (en) | 2000-06-23 | 2002-07-16 | International Business Machines Corporation | Antireflective silicon-containing compositions as hardmask layer |
US20030176614A1 (en) | 2000-06-30 | 2003-09-18 | Nigel Hacker | Organohydridosiloxane resins with high organic content |
US6368400B1 (en) | 2000-07-17 | 2002-04-09 | Honeywell International | Absorbing compounds for spin-on-glass anti-reflective coatings for photolithography |
JP4622061B2 (ja) * | 2000-07-27 | 2011-02-02 | Jsr株式会社 | レジスト下層膜用組成物およびその製造方法 |
JP4141625B2 (ja) | 2000-08-09 | 2008-08-27 | 東京応化工業株式会社 | ポジ型レジスト組成物およびそのレジスト層を設けた基材 |
EP1197511A1 (en) | 2000-10-10 | 2002-04-17 | Shipley Company LLC | Antireflective composition |
TW588072B (en) | 2000-10-10 | 2004-05-21 | Shipley Co Llc | Antireflective porogens |
US6589711B1 (en) | 2001-04-04 | 2003-07-08 | Advanced Micro Devices, Inc. | Dual inlaid process using a bilayer resist |
US6746530B2 (en) | 2001-08-02 | 2004-06-08 | Chunghwa Pictures Tubes, Ltd. | High contrast, moisture resistant antistatic/antireflective coating for CRT display screen |
US20030096090A1 (en) | 2001-10-22 | 2003-05-22 | Boisvert Ronald Paul | Etch-stop resins |
WO2003044600A1 (en) | 2001-11-15 | 2003-05-30 | Honeywell International Inc. | Spin-on anti-reflective coatings for photolithography |
EP1478682A4 (en) | 2001-11-15 | 2005-06-15 | Honeywell Int Inc | ANTIREFLECTIVE LAYERS FOR PHOTOLITHOGRAPHY AND METHODS OF PREPARATION THEREOF |
EP1478681A4 (en) | 2001-11-16 | 2006-10-11 | Honeywell Int Inc | SPIN ON GLASS ANTIREFLECTION COATINGS FOR PHOTOLITHOGRAPHY |
CN1230462C (zh) * | 2002-01-10 | 2005-12-07 | 中国石油化工股份有限公司 | 一种苯基和甲基聚倍半硅氧烷预聚体的制备 |
CN1230463C (zh) * | 2002-01-10 | 2005-12-07 | 中国石油化工股份有限公司 | 苯基聚倍半硅氧烷预聚体的制备方法 |
US6730454B2 (en) | 2002-04-16 | 2004-05-04 | International Business Machines Corporation | Antireflective SiO-containing compositions for hardmask layer |
AU2003295517A1 (en) | 2002-11-12 | 2004-06-03 | Honeywell International Inc | Anti-reflective coatings for photolithography and methods of preparation thereof |
JP4244315B2 (ja) * | 2002-12-02 | 2009-03-25 | 東京応化工業株式会社 | レジストパターン形成用材料 |
KR100639862B1 (ko) | 2002-12-02 | 2006-10-31 | 토쿄오오카코교 가부시기가이샤 | 반사방지막형성용 조성물 |
JP4369203B2 (ja) * | 2003-03-24 | 2009-11-18 | 信越化学工業株式会社 | 反射防止膜材料、反射防止膜を有する基板及びパターン形成方法 |
TW200505966A (en) * | 2003-04-02 | 2005-02-16 | Dow Global Technologies Inc | Organosilicate resin formulation for use in microelectronic devices |
ATE377036T1 (de) | 2003-05-23 | 2007-11-15 | Dow Corning | Siloxan-harz basierte anti- reflektionsbeschichtung mit hoher nassätzgeschwindigkeit |
JP4430986B2 (ja) * | 2003-06-03 | 2010-03-10 | 信越化学工業株式会社 | 反射防止膜材料、これを用いた反射防止膜及びパターン形成方法 |
CN1291991C (zh) * | 2003-08-20 | 2006-12-27 | 胡立江 | 一种多羟基倍半硅氧烷的制备方法 |
JP4563076B2 (ja) * | 2004-05-26 | 2010-10-13 | 東京応化工業株式会社 | 反射防止膜形成用組成物、該反射防止膜形成用組成物からなる反射防止膜、および該反射防止膜形成用組成物を用いたレジストパターン形成方法 |
WO2006065320A1 (en) | 2004-12-17 | 2006-06-22 | Dow Corning Corporation | Method for forming anti-reflective coating |
JP5412037B2 (ja) | 2004-12-17 | 2014-02-12 | ダウ・コーニング・コーポレイション | シロキサン樹脂、シロキサン樹脂の調製方法および抗反射コーティング組成物 |
EP1825330B1 (en) | 2004-12-17 | 2019-04-24 | Dow Silicones Corporation | Method for forming anti-reflective coating |
JP4574595B2 (ja) * | 2006-06-23 | 2010-11-04 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
JP5000250B2 (ja) * | 2006-09-29 | 2012-08-15 | 東京応化工業株式会社 | パターン形成方法 |
US8026035B2 (en) * | 2007-03-30 | 2011-09-27 | Cheil Industries, Inc. | Etch-resistant disilane and saturated hydrocarbon bridged silicon-containing polymers, method of making the same, and method of using the same |
-
2005
- 2005-09-29 AT AT05800835T patent/ATE400672T1/de not_active IP Right Cessation
- 2005-09-29 WO PCT/US2005/035236 patent/WO2006065321A1/en active Application Filing
- 2005-09-29 EP EP05800835A patent/EP1819844B1/en not_active Not-in-force
- 2005-09-29 US US11/666,823 patent/US7833696B2/en not_active Expired - Fee Related
- 2005-09-29 JP JP2007546646A patent/JP4688882B2/ja not_active Expired - Fee Related
- 2005-09-29 CN CN2005800419565A patent/CN101072896B/zh not_active Expired - Fee Related
- 2005-09-29 DE DE200560008100 patent/DE602005008100D1/de active Active
- 2005-10-19 TW TW094136611A patent/TWI372946B/zh not_active IP Right Cessation
-
2007
- 2007-06-15 KR KR1020077013562A patent/KR101275649B1/ko not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101624447B (zh) * | 2008-07-09 | 2012-11-21 | 三星移动显示器株式会社 | 聚倍半硅氧烷共聚物及其制造方法、聚倍半硅氧烷共聚物薄膜和有机发光二极管显示装置 |
CN102245722A (zh) * | 2008-12-10 | 2011-11-16 | 陶氏康宁公司 | 可转换的抗反射涂层 |
CN102245722B (zh) * | 2008-12-10 | 2014-12-10 | 陶氏康宁公司 | 可转换的抗反射涂层 |
TWI490656B (zh) * | 2008-12-10 | 2015-07-01 | Dow Corning | 可切換之抗反射塗料 |
TWI490655B (zh) * | 2008-12-10 | 2015-07-01 | Dow Corning | 倍半矽氧烷樹脂 |
Also Published As
Publication number | Publication date |
---|---|
EP1819844B1 (en) | 2008-07-09 |
EP1819844A1 (en) | 2007-08-22 |
JP2008525824A (ja) | 2008-07-17 |
TW200630755A (en) | 2006-09-01 |
US20090123701A1 (en) | 2009-05-14 |
US7833696B2 (en) | 2010-11-16 |
KR20070086265A (ko) | 2007-08-27 |
ATE400672T1 (de) | 2008-07-15 |
JP4688882B2 (ja) | 2011-05-25 |
DE602005008100D1 (de) | 2008-08-21 |
CN101072896B (zh) | 2010-05-05 |
WO2006065321A1 (en) | 2006-06-22 |
TWI372946B (en) | 2012-09-21 |
KR101275649B1 (ko) | 2013-06-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101072896B (zh) | 形成抗反射涂层的方法 | |
CN101073038B (zh) | 形成抗反射涂层的方法 | |
CN101371196B (zh) | 抗反射涂料 | |
CN101073039B (zh) | 形成抗反射涂层的方法 | |
CN101910253B (zh) | 倍半硅氧烷树脂 | |
US8304161B2 (en) | Silsesquioxane resins | |
CN101072813B (zh) | 硅氧烷树脂涂料 | |
US7756384B2 (en) | Method for forming anti-reflective coating | |
TW200946595A (en) | Silsesquioxane resins | |
US8653217B2 (en) | Method for forming anti-reflective coating | |
WO2007094849A2 (en) | Antireflective coating material |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20100505 Termination date: 20150929 |
|
EXPY | Termination of patent right or utility model |