CN102725695B - 形成有机抗反射层的异氰脲酸酯化合物和包含所述化合物的组合物 - Google Patents
形成有机抗反射层的异氰脲酸酯化合物和包含所述化合物的组合物 Download PDFInfo
- Publication number
- CN102725695B CN102725695B CN201080039879.0A CN201080039879A CN102725695B CN 102725695 B CN102725695 B CN 102725695B CN 201080039879 A CN201080039879 A CN 201080039879A CN 102725695 B CN102725695 B CN 102725695B
- Authority
- CN
- China
- Prior art keywords
- formula
- antireflective coating
- compound
- weight ratio
- isocyanurate compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 Isocyanurate compound Chemical class 0.000 title claims abstract description 87
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 230000003667 anti-reflective effect Effects 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 239000006117 anti-reflective coating Substances 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000126 substance Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000004132 cross linking Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000005530 etching Methods 0.000 abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 125000001309 chloro group Chemical group Cl* 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 0 *C(c1ccccc1)=O Chemical compound *C(c1ccccc1)=O 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229920002120 photoresistant polymer Polymers 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000001259 photo etching Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 230000003442 weekly effect Effects 0.000 description 4
- VLLPVDKADBYKLM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;triphenylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VLLPVDKADBYKLM-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 238000001312 dry etching Methods 0.000 description 3
- 238000000635 electron micrograph Methods 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- PMZBHPUNQNKBOA-UHFFFAOYSA-N 5-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(C(O)=O)=C1 PMZBHPUNQNKBOA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- WEBRDDDJKLAXTO-UHFFFAOYSA-N CCC1OCCO1 Chemical compound CCC1OCCO1 WEBRDDDJKLAXTO-UHFFFAOYSA-N 0.000 description 1
- 101100165177 Caenorhabditis elegans bath-15 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000003500 flue dust Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Images
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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/04—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D251/06—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/006—Anti-reflective coatings
-
- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- 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
- H01L21/02002—Preparing wafers
- H01L21/02005—Preparing bulk and homogeneous wafers
- H01L21/02008—Multistep processes
- H01L21/0201—Specific process step
-
- 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
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
-
- 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
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
- H01L21/0276—Photolithographic processes using an anti-reflective 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
- H01L21/34—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 not provided for in groups H01L21/0405, H01L21/0445, H01L21/06, H01L21/16 and H01L21/18 with or without impurities, e.g. doping materials
- H01L21/46—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/428
- H01L21/461—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/428 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/469—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/428 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After-treatment of these layers
- H01L21/4757—After-treatment
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0216—Coatings
- H01L31/02161—Coatings for devices characterised by at least one potential jump barrier or surface barrier
- H01L31/02167—Coatings for devices characterised by at least one potential jump barrier or surface barrier for solar cells
- H01L31/02168—Coatings for devices characterised by at least one potential jump barrier or surface barrier for solar cells the coatings being antireflective or having enhancing optical properties for the solar cells
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/06—Polymers
- H01L2924/0705—Sulfur containing polymer
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/30—Technical effects
- H01L2924/36—Material effects
- H01L2924/364—Polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Structural Engineering (AREA)
- Architecture (AREA)
- Sustainable Development (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Electromagnetism (AREA)
- Sustainable Energy (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Photolithography (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
公开了用于形成有机抗反射层的异氰脲酸酯化合物和包括所述异氰脲酸酯化合物的组合物,所述抗反射层在高温(25℃或更高)下具有优异的稳定性、优异的蚀刻速率以及高折射率。所述用于形成有机抗反射层的异氰脲酸酯化合物由权利要求1的通式1所表示。在通式1中,R各自独立地为氢或甲基,R1各自独立地为具有1至15个碳原子且包含0至6个杂原子的脂肪族或环状的饱和或不饱和烃,并且R2各自独立地为具有1至15个碳原子且包含0至15个杂原子的脂肪族或环状的饱和或不饱和烃。
Description
发明领域
本发明涉及用于形成有机抗反射涂层的异氰脲酸酯化合物和包含所述异氰脲酸酯化合物的组合物,并且更特别地涉及用于形成在高温(25℃或更高)下具有优异稳定性和蚀刻速率及高折射率的有机抗反射涂层的异氰脲酸酯化合物,以及包含所述异氰脲酸酯化合物的组合物。
发明背景
在光刻过程中,短波长的ArF(193nm)准分子激光器用作暴露光源以改善光致抗蚀剂图形的边缘分辨率。然而,如果暴露光的波长缩短,则由从半导体基板的蚀刻层反射的光而产生的光干扰效应增加,并且由于凹割、开槽等导致图形外廓或厚度均匀性下降。为了克服这些问题,一般在蚀刻层和光致抗蚀剂层之间形成底部抗反射涂层(底部抗反射涂料:BARC)以吸收暴露光(反射光)。能够根据使用的材料将底部抗反射涂层分为无机抗反射涂层和有机抗反射涂层,所述无机抗反射涂层由钛、二氧化钛、氮化钛、氧化铬、碳、无定形硅等制成,所述有机抗反射涂层由聚合物材料制成。一般地,与无机抗反射涂层相比,有机抗反射涂层不需要复杂和昂贵的装置,例如用于形成层的真空蒸发器、化学气相沉积(CVD)设备、溅射设备等,并且对放射光具有高吸收率,而且低分子量材料在加热、涂覆和干燥过程中不从有机抗反射涂层扩散入光致抗蚀剂层,并且有机抗反射涂层在光刻过程的干式蚀刻过程中具有优异的蚀刻速率。
Nissan Chemical Industries,Ltd.的第US 6,414,146B1号美国专利公开了异氰脲酸酯化合物和制备所述异氰脲酸酯化合物的方法。所述异氰脲酸酯化合物具有高折射率,并且可用作有机抗反射涂层。然而,该异氰脲酸酯化合物是不稳定的,因为其在末端具有巯基(-SH)并且能够在室温(25℃)或更高温度下形成二硫键。
发明概述
因此,本发明的目的是提供在将包括ArF在内的多种辐射用作暴露光源的光刻过程中,形成有机抗反射涂层的异氰脲酸酯化合物和包含所述异氰脲酸酯化合物的组合物,其在高温(25℃或更高)下具有优异稳定性和蚀刻速率以及高折射率。
本发明的另一目的是提供形成有机抗反射涂层的异氰脲酸酯化合物和包含所述异氰脲酸酯化合物的组合物,其能通过防止凹割、开槽和横向刻蚀(footing)而改善图形外廓。
为了实现这些目的,本发明提供了用于形成有机抗反射涂层的下列式1表示的异氰脲酸酯化合物。
[式1]
在式1中,R独立地为氢原子或甲基,R1独立地为含0至6个杂原子的具有1至15个碳原子的链型或环型饱和或不饱和烃基,并且R2独立地为含0至15个杂原子的具有1至15个碳原子的链型或环型饱和或不饱和烃基,其中,R1能够具有至少两个结合部分,并且R1具有至少两个结合部分的情况下,式1表示的化合物除R1以外的剩余部分能够与R1连接以形成聚合物结构。
本发明也提供了形成有机抗反射涂层的组合物,其包含:用于形成有机抗反射涂层的1至5%重量比的异氰脲酸酯化合物;0.01至0.25%重量比的酸产生剂;0.01至0.4%重量比的交联剂;以及剩余的有机溶剂。
通过使用本发明的用于形成有机抗反射涂层的异氰脲酸酯化合物,能够形成在高温(25℃或更高)下具有优异稳定性(归因于化合物的封端巯基(-SH))、甚至在193nm短波长的光线下具有高折射率(归因于其的氮原子(N)、硫原子(S)和氧原子(O))并且具有优异蚀刻速率(通过其碳-氧键(C-O键))的有机抗反射涂层。此外,能够通过用于封端巯基(-SH)的封端材料的变化来控制有机抗反射层的k值(消光系数),并且能够通过有效地防止反射光产生的凹割、开槽和横向刻蚀来改善图形外廓。因此,其可在使用诸如ArF(193nm)准分子激光器的光源的光刻过程中用作有机抗反射涂层。
附图简述
图1是示出本发明实施例1制备的式1a所示的异氰脲酸酯化合物的分子量的GPC图,其在两个月内每周检测。
图2是示出本发明比较例1制备的式5所示的异氰脲酸酯化合物的分子量的GPC图,其在两个月内每周检测。
图3是由本发明实施例16形成的光致抗蚀剂图形的电子显微图。
图4是由本发明比较例3形成的光致抗蚀剂图形的电子显微图。
发明详述
通过参考下面详述将更好地认识到本发明的更全面的理解及其许多附随优势。
下面式1表示用于形成本发明的有机抗反射涂层的异氰脲酸酯化合物,其能够在半导体基板的蚀刻层和光致抗蚀剂层之间形成有机抗反射涂层,并且通过吸收从蚀刻层反射的光来防止凹割、开槽和横向刻蚀等。
【式1】
在式1中,R独立地为氢原子或甲基,能具有至少一个结合部分的R1独立地为含0至6个杂原子的具有1至15个碳原子的链型或环型饱和或不饱和烃基,优选为含0至4个诸如氮原子(N)、氧原子(O)和/或硫原子(S)的杂原子的具有1至10个碳原子的链型或环型饱和或不饱和烃基,并且R2独立地为含0至15个杂原子的具有1至15个碳原子的链型或环型饱和或不饱和烃基,优选为含0至8个诸如氮原子(N)、氧原子(O)和/或硫原子(S)的杂原子的具有3至10个、更优选为5至10个碳原子的链型或环型饱和或不饱和烃基。
R1的详细实例包括 等(其中,波浪线表示结合部分)。R2的详细实例包括 等(其中,波浪线表示结合部分)。其中,R1能够具有至少两个结合部分,并且在R1具有至少两个结合部分的情况下,式1表示的化合物除R1以外的剩余部分能够与R1连接以形成聚合物结构(二聚体、三聚体等)。
式1表示的异氰脲酸酯化合物的典型实例包括下列式1a至1g表示的异氰脲酸酯化合物。
【式1a】
【式1b】
【式1c】
【式1d】
【式1e】
【式1f】
【式1g】
在式1a至1g中,R1与式1中的定义相同。此外,在R1具有至少两个结合部分的情况下,式1表示的化合物除R1以外的剩余部分能够独立地与R1连接以形成聚合物结构。
如下列反应1所示,(i)在室温下,在二甲基甲酰胺(DMF)中使三(1,3-氧硫杂环戊烷(oxathiolane)-2-亚硫酰-5-基甲基)异氰脲酸酯或三(5-甲基-1,3-氧硫杂环戊烷-2-亚硫酰-5-基甲基)异氰脲酸酯与含至少一个氨基(-NH2)和R1的化合物反应15至30小时,以获得下列式2表示的异氰脲酸酯化合物,以及(ii)将下列式2表示的异氰脲酸酯化合物溶于四氢呋喃(THF)中,并加入三乙胺(TEA)。然后,在将反应物的温度降低至0℃后,加入含R2的酰基氯或酰基溴,并使反应进行20至40分钟,并在室温下使反应进一步进行10至24小时以获得用于形成有机抗反射涂层的式1表示的异氰脲酸酯化合物。
【反应1】
在反应1中,R、R1和R2与式1中的定义相同,X是氯(Cl)或溴(Br),并且m是1或更大的整数,优选为1或2。
其中,能够将(式3a)、(式3b)、(式3c)、(式3d)、(式3e)、(式3f)、(式3g)、(式3h)、(式3i)、(式3j)、(式3k)、(式3l)、(式3m)、(式3n)、(式3o)、(式3p)、(式3q)、(式3r)、(式3s)或其混合物用作含至少一个氨基(-NH2)和R1的化合物并且,在其中m为大于等于2的化合物存在的情况下,至少两个三(1,3-氧硫杂环戊烷-2-亚硫酰-5-基甲基)异氰脲酸酯或三(5-甲基-1,3-氧硫杂环戊烷-2-亚硫酰-5-基甲基)异氰脲酸酯能够与所述化合物反应,并且式1和2表示的异氰脲酸酯化合物能够具有聚合物结构。
形成本发明的有机抗反射涂层的组合物包含用于形成有机抗反射涂层的异氰脲酸酯化合物、交联剂、酸产生剂和有机溶剂。
由含至少两个氨基的含R1化合物而形成或在形成有机抗反射涂层的过程期间通过与交联剂的反应而形成的聚合物类型是优选作为用于形成在本发明中使用的有机抗反射涂层的异氰脲酸酯化合物。对此,异氰脲酸酯化合物的重均分子量(Mw)为2,000至10,000,优选为4,000至8,000。如果重均分子量小于2,000,则有机抗反射涂层可以被光致抗蚀剂溶剂溶解。如果重均分子量大于10,000,则化合物在溶剂中的溶解度和有机抗反射涂层在干式蚀刻过程中的蚀刻速率可能降低。
用于形成有机抗反射涂层的异氰脲酸酯化合物的量为1%重量比至5%重量比,优选为2%重量比至4%重量比。如果化合物的量小于1%重量比,则可能不能形成有机抗反射涂层。如果化合物的量大于5%重量比,则诸如所形成的有机抗反射涂层的均匀性等的物理性质可能下降。
在本发明中使用的交联剂使得用于形成有机抗反射涂层的异氰脲酸酯化合物交联,从而形成聚合物和有机抗反射涂层。能够将例如三聚氰胺型交联剂等的常规交联剂用作交联剂。交联剂的量为0.01%重量比至0.4%重量比,优选为0.05%重量比至0.3%重量比。如果酸产生剂的量小于0.01%重量比,则可能不能形成有机抗反射涂层。如果酸产生剂的量大于0.4%重量比,则可能在图形外廓上产生横向刻蚀。
在本发明中使用的酸产生剂是为了促进用于形成有机抗反射涂层的异氰脲酸酯化合物的交联反应。能将常规酸产生剂用作酸产生剂,例如锍盐型化合物、碘鎓盐型化合物及其混合物等,优选全氟丁基磺酸三苯基锍盐、十二烷基苯磺酸、对甲苯磺酸等。酸产生剂的量为0.01%重量比至0.25%重量比,优选为0.05%重量比至0.2%重量比。如果酸产生剂的量小于0.01%重量比,则可能不能形成有机抗反射涂层。如果酸产生剂的量大于0.25%重量比,则在加热过程中产生的烟尘可能污染装置。
能够将用于形成有机抗反射涂层的组合物的常规有机溶剂用作在本发明中使用的有机溶剂。示例性的有机溶剂包括但不限于环己酮、环戊酮、丁内酯、二甲基乙酰胺、二甲基甲酰胺、二甲亚砜、N-甲基吡咯烷酮(NMP)、四氢糠醇、丙二醇单甲醚(PGME)、丙二醇单甲醚醋酸酯(PGMEA)、乳酸乙酯、它们的混合物等。对于100%重量比的用于形成有机抗反射涂层的总组合物而言,有机溶剂的量应当足以溶解用于形成有机抗反射涂层的组合物,即基本为除形成有机抗反射涂层的异氰脲酸酯化合物、交联剂和酸产生剂以外的剩余量(94.35%重量比至98.98%重量比)。
能够通过进行在诸如硅片和铝基底的蚀刻层上涂覆用于形成有机抗反射涂层的组合物的步骤以及使在蚀刻层上涂覆的用于形成有机抗反射涂层的组合物交联的步骤来形成本发明的有机抗反射涂层。能够通过诸如旋涂、滚涂等的常规方法实施涂覆用于形成有机抗反射涂层的组合物的步骤,并且能够通过使用诸如高温板、对流烘箱等的装置加热来进行使得用于形成有机抗反射涂层的涂覆的组合物交联的步骤。交联的加热温度为90℃至240℃,优选为150℃至210℃。如果加热温度小于90℃,则可能不能充分地除去用于形成有机抗反射涂层的组合物中的有机溶剂,并且可能不能充分地进行交联反应。如果加热温度高于240℃,则有机抗反射涂层和用于形成有机抗反射涂层的组合物可能变为化学不稳定的。
在下文中,提供了优选的实施例以更好地理解本发明。然而,本发明不限于下列实施例。
[实施例1]式1a表示的异氰脲酸酯化合物的制备
A.式5表示的异氰脲酸酯化合物的制备
向反应器中加入5g(0.0095mol)的三(1,3-氧硫杂环戊烷-2-亚硫酰-5-基甲基)异氰脲酸酯、1.41g(0.0095mol)的式3a表示的化合物3.46g(0.0285mol)的式3l表示的化合物和55.91g的二甲基甲酰胺(DMF),并在室温(25℃)下在搅拌过程中使其反应24小时以获得下面式5表示的异氰脲酸酯化合物(在式5中,R1为或(总化合物的摩尔比: 并且如果R1为则式5表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:85%,分子量(Mw):4,905,多分散性指数(PDI):1.83)。
[式5]
B.式1a表示的异氰脲酸酯化合物的制备
向反应器(250ml圆底烧瓶)中加入76.29g的四氢呋喃(THF),并且加入10g的式5表示的异氰脲酸酯化合物并溶解,并加入3.96g三乙胺(TEA),并使用冰浴使溶液温度降低至0℃。向溶液中缓慢加入5.48g的式4a表示的化合物(X为氯(Cl)),并反应30分钟,然后在除去冰浴后进一步反应15小时。在反应完成后,过滤固体。在二乙醚中沉淀剩余的溶液,然后过滤并干燥以获得式1a表示的异氰脲酸酯化合物(在式1a中,R1为或(总化合物的摩尔比: =1∶3),并且如果R1为则式1a表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:69.8%,分子量(Mw):5,241,多分散性指数(PDI):1.84)。
[实施例2]式1b表示的异氰脲酸酯化合物的制备
除了使用6.03g的式4b表示的化合物(X为氯(Cl))代替5.48g的式4a表示的化合物(X为氯(Cl))之外,以与实施例1描述的相同方式制备式1b表示的异氰脲酸酯化合物(在式1b中,R1为或(总化合物的摩尔比: =1∶3),并且如果R1为则式1b表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:73.0%,分子量(Mw):5,581,多分散性指数(PDI):1.83)。
[实施例3]式1c表示的异氰脲酸酯化合物的制备
除了使用6.65g的式4c表示的化合物(X为氯(Cl))代替5.48g的式4a表示的化合物(X为氯(Cl))之外,以与实施例1描述的相同方式制备式1c表示的异氰脲酸酯化合物(在式1c中,R1为或(总化合物的摩尔比: =1∶3),并且如果R1为则式1c表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:66.7%,分子量(Mw):5,751,多分散性指数(PDI):1.80)。
[实施例4]式1d表示的异氰脲酸酯化合物的制备
除了使用5.74g的式4d表示的化合物(X为氯(Cl))代替5.48g的式4a表示的化合物(X为氯(Cl))之外,以与实施例1描述的相同方式制备式1d表示的异氰脲酸酯化合物(在式1d中,R1为或(总化合物的摩尔比: =1∶3),并且如果R1为则式1d表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:71.8%,分子量(Mw):5,336,多分散性指数(PDI):1.86)。
[实施例5]式1e表示的异氰脲酸酯化合物的制备
除了使用5.11g的式4e表示的化合物(X为氯(Cl))代替5.48g的式4a表示的化合物(X为氯(Cl))之外,以与实施例1描述的相同方式制备式1e表示的异氰脲酸酯化合物(在式1e中,R1为或(总化合物的摩尔比: =1∶3),并且如果R1为则式1e表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:78.6%,分子量(Mw):5,121,多分散性指数(PDI):1.81)。
[实施例6]式1f表示的异氰脲酸酯化合物的制备
除了使用5.74g的式4f表示的化合物(X为氯(Cl))代替5.48g的式4a表示的化合物(X为氯(Cl))之外,以与实施例1描述的相同方式制备式1f表示的异氰脲酸酯化合物(在式1f中,R1为或(总化合物的摩尔比: =1∶3),并且如果R1为则式1f表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:62.2%,分子量(Mw):4,908,多分散性指数(PDI):1.90)。
[实施例7]式1g表示的异氰脲酸酯化合物的制备
除了使用4.16g的式4g表示的化合物(X为氯(Cl))代替5.48g的式4a表示的化合物(X为氯(Cl))之外,以与实施例1描述的相同方式制备式1g表示的异氰脲酸酯化合物(在式1g中,R1为或(总化合物的摩尔比: =1∶3),并且如果R1为则式1g表示的异氰脲酸酯化合物除R1以外的其余两个与连接并形成聚合物。产率:62.2%,分子量(Mw):5,218,多分散性指数(PDI):1.84)。
[比较例1]式5表示的异氰脲酸酯化合物的制备
通过与实施例1的步骤A中描述的相同方式制备式5表示的异氰脲酸酯化合物。
[实施例8]异氰脲酸酯化合物的稳定性试验
在高温(40℃)下,将实施例1制备的式1a表示的异氰脲酸酯化合物(封端化合物)和比较例1制备的式5表示的异氰脲酸酯化合物(未封端化合物)储存两个月,并且使用GPC(凝胶渗透色谱)每周检测它们的分子量。通过观察它们分子量随时间的变化来评价每一异氰脲酸酯化合物的稳定性。图1和图2是示出两个月内每周检测的式1a和式5表示的异氰脲酸酯化合物分子量的GPC图。
[实施例9至15和比较例2]用于形成有机抗反射涂层的组合物的制备 以及有机抗反射涂层的形成和试验
A.用于形成有机抗反射涂层的组合物的制备
下表1中,将3%重量比的实施例1至7中制备的异氰脲酸酯化合物(式1a至1g)中的一种或共聚物(苯乙烯∶甲基丙烯酸甲酯(MMA)∶甲基丙烯酸羟基乙酯(HEMA)=40∶30∶30,分子量(Mw)=15,000,多分散性指数(PDI)=1.8)、作为交联剂的0.2%重量比的PL 1174(制造商:Cytec Industries Inc.)和0.1%重量比的全氟丁基磺酸三苯基锍盐溶解于96.7%重量比的环己酮中,并搅拌以获得用于形成有机抗反射涂层的组合物。
B.有机抗反射涂层的形成
C.有机抗反射涂层的试验
使用介电蚀刻器(制造商:Lam research,设备名称:Exelan HPT)通过干式蚀刻气体(CF4)蚀刻有机抗反射涂层13秒以检测有机抗反射涂层的蚀刻速率(nm/秒),并使用椭率计(制造商:J.A.Woolam,设备名称:VUV-303)检测折射率和消光系数(k值)。结果显示在下列表1中。
【表1】
[实施例16至22和比较例3]光致抗蚀剂图形的形成和试验
以与实施例9至15和比较例2相同的方法在硅片的蚀刻层上形成-厚的有机抗反射涂层之后,以的厚度在所得的有机抗反射涂层上涂覆包含5g光敏聚合物(Mw=8,500,PDI=1.85)、0.2g全氟丁基磺酸三苯基锍盐、0.02g三辛基胺和100g丙二醇单甲醚醋酸酯的光致抗蚀剂组合物,并在110℃软烤60秒。
然后,使用具有线距(line and space)(L/S)图形的曝光掩模和193nm ArF曝光设备(ASML 1200B,0.85NA)使上述组合物暴露,然后在110℃坚膜60秒。并且,将其通过2.38%重量比的TMAH(氢氧化四甲铵)水溶液而显影以形成65nm行宽的1∶1线距(L/S)图形。实施例16和比较例3的光致抗蚀剂图形的电子显微照片显示在图3和图4中。
实施例17至22的结果与实施例16的结果相似。
如图1和图2所示,尽管时间改变,但本发明的用于形成有机抗反射涂层的异氰脲酸酯化合物(实施例1a、实施例1)具有稳定的GPC图,即,所述化合物的稳定性是优异的。并且,式5表示的异氰脲酸酯化合物(比较例1)具有随时间改变的GPC图,即,所述化合物的稳定性低。
式5表示的异氰脲酸酯化合物具有巯基(-SH)并且在室温(25℃)下能够形成二硫键,使得稳定性降低。但是通过将式5表示的化合物的巯基(-SH)进行封端而制备的式1a表示的异氰脲酸酯化合物失去其反应位点并且甚至在室温(25℃)或更高温度下具有稳定性。
此外,通过使用本发明的用于形成有机抗反射涂层的异氰脲酸酯化合物,能够形成有机抗反射涂层,其甚至在193nm的短波长光线下具有高折射率(归因于其的氮原子(N)、硫原子(S)和氧原子(O))以及表1所示的优异蚀刻速率。此外,能够通过改变用于封端巯基(-SH)的封端材料来控制有机抗反射层的k值(消光系数),并且如图3和图4所示,能够通过有效地防止反射光的凹割、开槽和横向刻蚀来改善图形外廓。
因此,本发明的用于形成有机抗反射涂层的异氰脲酸酯化合物在使用诸如ArF(193nm)准分子激光器的暴露光源的光刻过程中可用作用于形成有机抗反射涂层的组合物。
Claims (4)
4.用于形成有机抗反射涂层的方法,其包括步骤:
在蚀刻层上涂覆用于形成有机抗反射涂层的组合物,其中所述组合物包含1%重量比至5%重量比的下列式1表示的用于形成有机抗反射涂层的异氰脲酸酯化合物、0.01%重量比至0.4%重量比的交联剂、0.01%重量比至0.25%重量比的酸产生剂以及剩余的有机溶剂,
在式1中,R独立地为氢原子或甲基,R1独立地为含0至6个杂原子的具有1至15个碳原子的链型或环型饱和或不饱和烃基,并且R2独立地为含0至15个杂原子的具有1至15个碳原子的链型或环型饱和或不饱和烃基,其中,R1具有至少两个结合部分,并且在R1具有至少两个结合部分的情况下,式1表示的化合物除R1以外的剩余部分能够与R1连接以形成聚合物结构;以及
使在所述蚀刻层上涂覆的所述用于形成有机抗反射涂层的组合物交联。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020090086352A KR101710415B1 (ko) | 2009-09-14 | 2009-09-14 | 유기 반사방지막 형성용 이소시아누레이트 화합물 및 이를 포함하는 조성물 |
KR10-2009-0086352 | 2009-09-14 | ||
PCT/KR2010/006281 WO2011031123A2 (ko) | 2009-09-14 | 2010-09-14 | 유기 반사방지막 형성용 이소시아누레이트 화합물 및 이를 포함하는 조성물 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102725695A CN102725695A (zh) | 2012-10-10 |
CN102725695B true CN102725695B (zh) | 2014-06-25 |
Family
ID=43732989
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201080039879.0A Active CN102725695B (zh) | 2009-09-14 | 2010-09-14 | 形成有机抗反射层的异氰脲酸酯化合物和包含所述化合物的组合物 |
Country Status (5)
Country | Link |
---|---|
US (1) | US9063424B2 (zh) |
KR (1) | KR101710415B1 (zh) |
CN (1) | CN102725695B (zh) |
TW (1) | TWI520946B (zh) |
WO (1) | WO2011031123A2 (zh) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101993472B1 (ko) * | 2012-09-12 | 2019-09-30 | 주식회사 동진쎄미켐 | 레지스트 패턴의 하부막 형성용 화합물, 조성물 및 이를 이용한 하부막의 형성방법 |
KR102441290B1 (ko) * | 2015-07-29 | 2022-09-07 | 주식회사 동진쎄미켐 | 유기 반사방지막 형성용 조성물 |
KR102653125B1 (ko) | 2016-01-13 | 2024-04-01 | 삼성전자주식회사 | 포토레지스트의 하부막 조성물 및 이를 이용한 패턴 형성 방법 |
KR102662122B1 (ko) * | 2016-06-01 | 2024-04-30 | 주식회사 동진쎄미켐 | 네거티브 톤 현상 공정에 이용되는 유기 반사방지막 형성용 조성물 |
KR102604698B1 (ko) * | 2017-06-05 | 2023-11-23 | 주식회사 동진쎄미켐 | 높은 식각비를 갖는 유기 반사 방지막 형성용 조성물 |
CN111919174A (zh) * | 2018-03-27 | 2020-11-10 | 东京应化工业株式会社 | 镀敷造形物的制造方法 |
KR102264693B1 (ko) * | 2018-06-11 | 2021-06-11 | 삼성에스디아이 주식회사 | 레지스트 하층막용 조성물 및 이를 이용한 패턴형성방법 |
CN113929906B (zh) * | 2021-10-14 | 2023-07-04 | 厦门恒坤新材料科技股份有限公司 | 一种可自交联异氰尿酸酯聚合物和抗反射涂层组合物及其制备方法和图案形成方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20060046423A (ko) * | 2004-06-10 | 2006-05-17 | 신-에쮸 케미칼 컴퍼니 리미티드 | 반사 방지막 형성용 조성물, 그 제조 방법과 이를 이용한반사 방지막 및 패턴 형성 방법 |
KR20060048011A (ko) * | 2004-05-18 | 2006-05-18 | 롬 앤드 하스 일렉트로닉 머트어리얼즈, 엘.엘.씨. | 상층 코팅된 포토레지스트와 함께 사용하기 위한 코팅조성물 |
KR20070012512A (ko) * | 2004-05-14 | 2007-01-25 | 닛산 가가쿠 고교 가부시키 가이샤 | 비닐에테르 화합물을 포함하는 반사방지막 형성 조성물 |
WO2008069047A1 (ja) * | 2006-11-28 | 2008-06-12 | Nissan Chemical Industries, Ltd. | 芳香族縮合環を含有する樹脂を含むリソグラフィー用レジスト下層膜形成組成物 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6414061B1 (en) * | 1997-08-21 | 2002-07-02 | Crompton Corporation | Blocked mercaptosilane coupling agents for filled rubbers |
DE60207902T2 (de) | 2001-01-30 | 2006-06-14 | Nissan Chemical Ind Ltd | Isocyanuratverbindung und Verfahren zu ihrer Herstellung |
-
2009
- 2009-09-14 KR KR1020090086352A patent/KR101710415B1/ko active IP Right Grant
-
2010
- 2010-09-14 WO PCT/KR2010/006281 patent/WO2011031123A2/ko active Application Filing
- 2010-09-14 CN CN201080039879.0A patent/CN102725695B/zh active Active
- 2010-09-14 TW TW099131086A patent/TWI520946B/zh active
- 2010-09-14 US US13/393,682 patent/US9063424B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20070012512A (ko) * | 2004-05-14 | 2007-01-25 | 닛산 가가쿠 고교 가부시키 가이샤 | 비닐에테르 화합물을 포함하는 반사방지막 형성 조성물 |
KR20060048011A (ko) * | 2004-05-18 | 2006-05-18 | 롬 앤드 하스 일렉트로닉 머트어리얼즈, 엘.엘.씨. | 상층 코팅된 포토레지스트와 함께 사용하기 위한 코팅조성물 |
KR20060046423A (ko) * | 2004-06-10 | 2006-05-17 | 신-에쮸 케미칼 컴퍼니 리미티드 | 반사 방지막 형성용 조성물, 그 제조 방법과 이를 이용한반사 방지막 및 패턴 형성 방법 |
WO2008069047A1 (ja) * | 2006-11-28 | 2008-06-12 | Nissan Chemical Industries, Ltd. | 芳香族縮合環を含有する樹脂を含むリソグラフィー用レジスト下層膜形成組成物 |
Also Published As
Publication number | Publication date |
---|---|
TWI520946B (zh) | 2016-02-11 |
KR101710415B1 (ko) | 2017-02-27 |
WO2011031123A3 (ko) | 2011-07-14 |
TW201116518A (en) | 2011-05-16 |
KR20110028763A (ko) | 2011-03-22 |
CN102725695A (zh) | 2012-10-10 |
WO2011031123A2 (ko) | 2011-03-17 |
US20120164338A1 (en) | 2012-06-28 |
US9063424B2 (en) | 2015-06-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102725695B (zh) | 形成有机抗反射层的异氰脲酸酯化合物和包含所述化合物的组合物 | |
TWI432903B (zh) | 圖案形成方法 | |
KR100242224B1 (ko) | 레지스트 조성물, 레지스트 패턴의 형성 방법 및 반도체 장치의 제조 방법 | |
TWI384328B (zh) | 用以形成抗反射塗層的聚合物 | |
TWI564659B (zh) | I-line光阻成分及使用其形成精細圖案的方法 | |
TWI598694B (zh) | 用於形成光阻下層膜之化合物及組成物,以及使用該化合物及組成物形成光阻下層膜之方法 | |
JP5418906B2 (ja) | 反射防止コーティング組成物 | |
KR101156973B1 (ko) | 유기 반사방지막 형성용 유기 중합체 및 이를 포함하는 유기 조성물 | |
KR100574482B1 (ko) | 유기 난반사 방지막용 조성물과 이의 제조방법 | |
JP5520440B2 (ja) | 有機反射防止膜形成用単量体、重合体及びこれを含む有機組成物 | |
CN113929906A (zh) | 一种可自交联异氰尿酸酯聚合物和抗反射涂层组合物及其制备方法和图案形成方法 | |
US20050142481A1 (en) | Cross-linking polymer for organic anti-reflective coating, organic anti-reflective coating composition comprising the same and method for forming photoresist pattern using the same | |
KR102302997B1 (ko) | 용해도 특성이 향상된 유기화합물 및 그 제조 방법 | |
KR102604698B1 (ko) | 높은 식각비를 갖는 유기 반사 방지막 형성용 조성물 | |
KR20170014120A (ko) | 유기 반사방지막 형성용 조성물 | |
KR20130114071A (ko) | 반사 방지 코팅 조성물 및 마이크로일렉트로닉 디바이스의 제조 방법 | |
EP2000853A2 (en) | Photo-sensitive compound and photoresist composition including the same | |
KR102194297B1 (ko) | 인돌-플루오렌 중합체를 함유하는 반사방지용 하드마스크 조성물 | |
JP2011209694A5 (zh) | ||
US20040009424A1 (en) | Protecting groups for lithographic resist compositions | |
KR20230051814A (ko) | 중합체, 그 제조 방법, 중합체를 포함하는 유기막 및 응용 | |
KR100680406B1 (ko) | 포토레지스트 중합체 및 이를 포함하는 포토레지스트 조성물 | |
KR20220091874A (ko) | 감광성 고분자 및 포토레지스트 조성물 | |
KR20030050556A (ko) | 열산발생제를 포함하는 유기 난반사 방지막을 이용한초미세 패턴의 형성방법 |
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 |