JP6558894B2 - コポリマーの設計、その製造方法およびそれを含む物品 - Google Patents
コポリマーの設計、その製造方法およびそれを含む物品 Download PDFInfo
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- JP6558894B2 JP6558894B2 JP2014254295A JP2014254295A JP6558894B2 JP 6558894 B2 JP6558894 B2 JP 6558894B2 JP 2014254295 A JP2014254295 A JP 2014254295A JP 2014254295 A JP2014254295 A JP 2014254295A JP 6558894 B2 JP6558894 B2 JP 6558894B2
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- 125000005022 dithioester group Chemical group 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 description 2
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- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
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- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 2
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- URUIKGRSOJEVQG-UHFFFAOYSA-N 2-dodecylsulfanylcarbothioylsulfanylacetonitrile Chemical compound CCCCCCCCCCCCSC(=S)SCC#N URUIKGRSOJEVQG-UHFFFAOYSA-N 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 101100490446 Penicillium chrysogenum PCBAB gene Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 229920000390 Poly(styrene-block-methyl methacrylate) Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001504 aryl thiols Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical group 0.000 description 1
- LWGLGSPYKZTZBM-UHFFFAOYSA-N benzenecarbonothioylsulfanyl benzenecarbodithioate Chemical compound C=1C=CC=CC=1C(=S)SSC(=S)C1=CC=CC=C1 LWGLGSPYKZTZBM-UHFFFAOYSA-N 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- FYACMHCOSCVNHO-UHFFFAOYSA-N cyanomethyl n-methyl-n-phenylcarbamodithioate Chemical compound N#CCSC(=S)N(C)C1=CC=CC=C1 FYACMHCOSCVNHO-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- UUNRYKCXJSDLRD-UHFFFAOYSA-N dodecylsulfanyl-(dodecylsulfanylcarbothioyldisulfanyl)methanethione Chemical compound CCCCCCCCCCCCSC(=S)SSC(=S)SCCCCCCCCCCCC UUNRYKCXJSDLRD-UHFFFAOYSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- OUGJKAQEYOUGKG-UHFFFAOYSA-N ethyl 2-methylidenebutanoate Chemical compound CCOC(=O)C(=C)CC OUGJKAQEYOUGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- JKJJSJJGBZXUQV-UHFFFAOYSA-N methyl 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)OC JKJJSJJGBZXUQV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 1
- FPFRTDOMIFBPBZ-UHFFFAOYSA-N n-tert-butyl-2-methyl-1-phenyl-n-(1-phenylethoxy)propan-1-amine Chemical compound C=1C=CC=CC=1C(C(C)C)N(C(C)(C)C)OC(C)C1=CC=CC=C1 FPFRTDOMIFBPBZ-UHFFFAOYSA-N 0.000 description 1
- VGHCMXLEZFMZOZ-UHFFFAOYSA-N n-tert-butyl-n-$l^{1}-oxidanyl-2-methyl-1-phenylpropan-1-amine Chemical compound CC(C)(C)N([O])C(C(C)C)C1=CC=CC=C1 VGHCMXLEZFMZOZ-UHFFFAOYSA-N 0.000 description 1
- WZYBDTCNEIULNZ-UHFFFAOYSA-N n-tert-butyl-n-[1-[4-(chloromethyl)phenyl]ethoxy]-2-methyl-1-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(C)C)N(C(C)(C)C)OC(C)C1=CC=C(CCl)C=C1 WZYBDTCNEIULNZ-UHFFFAOYSA-N 0.000 description 1
- 238000005329 nanolithography Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000654 solvent vapour annealing Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
-
- 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
- C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
-
- 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
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
-
- 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
- H01L21/04—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
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31127—Etching organic layers
- H01L21/31133—Etching organic layers by chemical means
- H01L21/31138—Etching organic layers by chemical means by dry-etching
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
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- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Power Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Graft Or Block Polymers (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Description
[式1]
O.N.=N/(NC−NO)
式中、Nは繰り返し単位中の原子の総数、NCは繰り返し単位中の炭素原子数、NOは繰り返し単位中の酸素原子数である。高O.N.ポリマーほど酸素エッチング速度が速い。
[式2]
O.N.AB=fAO.N.A+fBO.N.B
式中、fはモル比、O.N.は各モノマーのOhnishiの数である。ブラシおよびマットは、近いOhnishiの数を持つことが望ましい。さらにブラシおよびマットは、誘導自己組織化において現在用いられているP(S−r−MMA)コポリマーより大きなOhnishiの数を持つことが望ましい。
本実施例は、ポリスチレンおよび2−(1,2−ジヒドロシクロブタベンゼン−1−イルオキシ)エチルメタクリレート(BCBMA)によるランダムコポリマーを含む組成物の製造を実演するために行われた。16.028gのスチレンおよび3.972gの2−(1,2−ジヒドロシクロブタベンゼン−1−イルオキシ)エチルメタクリレート(BCBMA)を30.000gのプロピレングリコールメチルエーテルアセテート(PGMEA)に溶解した。20分間窒素通気することによって、モノマー溶液を脱気した。PGMEA(14.964グラム(g))を、濃縮器および機械的撹拌器に備えられた250mLの三つ口フラスコに加え、20分間窒素通気することによって脱気した。次いで、反応フラスコ内の溶媒の温度を80℃まで引き上げた。V601(ジメチル−2,2−アゾジイソブチレート)(0.984g)を4.000gのPGMEAに溶解し、開始剤溶液も20分間窒素通気することによって脱気した。開始剤溶液を反応フラスコに加え、次いでモノマー溶液を厳しい撹拌および窒素環境のもとで3時間かけて反応器に滴下した。モノマーの供給完了後、重合混合物をさらに1時間、80℃で保持した。合計4時間の重合時間(供給3時間、供給後の撹拌1時間)の後、重合混合物を室温まで冷えるままにした。メタノール/水(80/20)で沈殿させた。沈殿したポリマーをろ過によって回収し、一晩空気乾燥させ、THFに再溶解し、メタノール/水(80/20)で再沈殿させた。最終ポリマーをろ過し、一晩空気乾燥させ、さらに真空下、25℃で48時間乾燥し、以下に示すポリマーAを得た。
本実施例は、マット組成物において用いられる、本明細書に開示のポリアクリレート・ランダムコポリマーの製造方法を明らかにする。15.901gのメチルメタクリレート(MMA)および4.099gの2−(1,2−ジヒドロシクロブタベンゼン−1−イルオキシ)エチルメタクリレート(BCBMA)を、30.000gのプロピレングリコールメチルエーテルアセテート(PGMEA)に溶解した。20分間窒素通気することによって、モノマー溶液を脱気した。PGMEA(15.037g)を、濃縮器および機械的撹拌器に備えられた250mLの三つ口フラスコに加え、20分間窒素通気することによって脱気した。次いで、反応フラスコ内の溶媒の温度を80℃まで引き上げた。V601(ジメチル−2,2−アゾジイソブチレート)(1.016g)を4.000gのPGMEAに溶解し、開始剤溶液も20分間窒素通気することによって脱気した。開始剤溶液を反応フラスコに加え、次いでモノマー溶液を厳しい撹拌および窒素環境のもとで3時間かけて反応器に滴下した。モノマーの供給完了後、重合混合物をさらに1時間、80℃で保持した。合計4時間の重合時間(供給3時間、供給後の撹拌1時間)の後、重合混合物を室温まで冷えるままにした。メタノール/水(80/20)で沈殿させた。沈殿したポリマーをろ過によって回収し、一晩空気乾燥させ、THFに再溶解し、メタノール/水(80/20)で再沈殿させた。最終ポリマーをろ過し、一晩空気乾燥させ、さらに真空下、25℃で48時間乾燥し、以下に示す構造を持つマット組成物(ポリマーBとする)を得た。Ohnishiの数は4.8である。
この実施例は、ポリマーマットのエッチング速度測定を実演するために行われた。
この比較例は、ブラシバックフィル組成物を形成する、ポリスチレンおよびポリメチルメタクリレート(ポリ(スチレン−r−メチルメタクリレート)−OH(61.4/38.6))を含むランダムコポリマーの製造およびエッチングを実演するために行われた。スチレンおよびメチルメタクリレート(MMA)を塩基性アルミナに通した。250mLの反応器(隔壁付き)に、スチレン(20.000g)、MMA(13.314g)、CuBr(0.191g)およびアニソール(54ml)を加え、窒素を用いて45分間パージした。リガンド(PMDETA、0.4615g)(ATRP反応を可能にする)を、窒素パージの下さらに15分間、シリンジを介して反応混合物に注入した。温度を95℃に引き上げた。10分後、開始剤を反応器に注入した。次に窒素パージを中止した。分子量がモルあたり10,000グラムに到達した時点で重合を止めた。重合混合物を塩基性アルミナに通し、次にメタノール中に沈殿させた。沈殿物をテトラヒドロフランに溶解し、再度塩基性アルミナ、次いで陽イオン交換樹脂に通し、メタノールを用いて再沈殿させた。白色粉末をろ過し、一晩50℃で乾燥し、以下に示す構造を持ち、61.4モル%がスチレンおよび38.6モル%がメチルメタクリレートであり、Ohnishiの数が3.2であるポリマーCを得た。
この実施例は、本開示のポリ(アルキルメタクリレート)を含むブラシバックフィル組成物の製造を実演するために行われた。この特定の実施例においては、ブラシ組成物は、ポリ(エチルメタクリレート)を含む。エチルメタクリレート(EMA)を塩基性アルミナに通した。250mLの反応器(隔壁付き)にEMA(20.000g)、CuBr(0.114g)およびアニソール(60g)を加え、窒素を用いて45分間パージした。リガンド(PMDETA、0.277g)を、窒素パージの下さらに15分間、シリンジを介して反応混合物に注入した。温度を95℃に引き上げた。10分後、開始剤を反応器に注入した。次に窒素パージを中止した。分子量がモルあたり約10,000グラムに到達した時点で重合を止めた。重合混合物を塩基性アルミナに通し、次にメタノール中に沈殿させた。沈殿物をテトラヒドロフランに溶解し、再度塩基性アルミナに通し、次いで陽イオン交換樹脂処理(塩およびイオン除去のため)ならびにメタノールからの再沈殿を行った。白色粉末をろ過し、一晩50℃で乾燥し、Ohnishiの数が4.5であるポリマーDを得た。
この実施例は、中性ブラシポリマーの評価(指紋状モルフォロジー形成による)を行うために行われた。ポリマーCおよびDをPGMEA(1.3wt%)に溶解し、ベアシリコンウェハ上に3000rpmでスピンコートし、次に250℃で20分間ベークした。未反応のブラシを、PGMEAで2回すすぐことにより除去した。次に、PS−b−PMMAのPGMEA溶液をスピンコートし、次いで250℃で2分間ベークすることにより、ポリスチレン−ブロック−ポリメチルメタクリレート・ブロックコポリマー(PS−b−PMMA)の薄膜をブラシコートされた基板上に配置した。モルフォロジーは、原子間力顕微鏡(AFM)を用いて撮像された。図6は、ベアSiウェハにグラフトされた、PS−r−PMMAブラシ(A)およびPEMA−OH(B)上のPS−b−PMMAで生成された指紋状パターンを示す。PEMA−OHブラシ(B)上に生成した指紋状パターンにより、PS−b−PMMAのいずれのブロックにも非選択的な中性表面という望ましい特徴が明示された。しかしながら、このブラシは、そのOhnishiの数が4.5であり3.2と比べてより大きく(表1)、図7に明示されるようにエッチング速度が速いことから、PS−r−PMMAブラシに対して優位である。
この実施例により、比較例3および実施例3のポリマーBブラシを用いた時のエッチング速度が実証される。ポリマーCおよびDをPGMEA(1.3wt%)に溶解し、ベアシリコンウェハ上に3000rpmでスピンコートし、次に150℃で2分間ソフトベークし、約35ナノメートルの初期膜厚を得た。PS−r−PMMA−OH(ポリマーC)およびPEMA−OH(ポリマーD)の両方の中性ブラシにO2プラズマを種々の時間当て、残った厚みを測定し、時間の関数として図7にプロットした。アクリレートをベースにした中性ブラシ(PEMA−OH)のエッチング速度は、図7中の表の条件の下では、PS−r−PMMA−OHブラシよりほぼ2倍速い。
.2倍、好ましくは少なくとも1.5倍、より好ましくは少なくとも2倍である。
また本発明のブラシバックフィル組成物には以下の(1)〜(4)の態様が含まれる:
(1)半導体の製造で使用するためのブラシバックフィル組成物であって、
半導体基板に対して反応し得る官能基を持つポリ(アルキルアクリレート)であって、前記ブラシバックフィル組成物はマット組成物からなる細片の間に配置され、前記ブラシバックフィル組成物およびマット組成物は半導体基板上に配置され、また前記ブラシバックフィル組成物はその上に配置されるブロックコポリマーのうちの少なくとも1つの成分と実質的に同様のエッチング特性を持つポリ(アルキルアクリレート)、を含むブラシバックフィル組成物:
(2)前記ブラシバックフィル組成物が4より大きいOhnishiパラメータを持つ、前記(1)に記載のブラシバックフィル組成物:
(3)前記ポリ(アルキルアクリレート)がエチルメタクリレートの重合より生じるモノマー単位を含む、前記(1)または(2)のいずれか1つに記載のブラシバックフィル組成物:並びに、
(4)前記ポリ(アルキルアクリレート)が式(5)に示す構造を含む、前記(1)〜(3)のいずれか1つに記載のブラシバックフィル組成物。
(式中、n 3 は75〜125)。
Claims (6)
- マット組成物を半導体基板の表面上に配置することであって、前記マット組成物は、第一のアクリレート単位および第二の単位を含むランダムコポリマーを含み、前記コポリマーはポリスチレンおよびポリエポキシドを含まないこと、
前記ランダムコポリマーを架橋すること、
ブラシバックフィル組成物を前記基板上に、前記ブラシバックフィル組成物およびマット組成物が交互となるように、配置すること、こここで、前記ブラシバックフィル組成物はその上に配置されるブロックコポリマーのうちの少なくとも1つの成分と実質的に同様のエッチング特性を持ち、
前記ブラシバックフィル組成物上および前記マット組成物上に、自己組織化するブロックコポリマーを配置すること、および
前記ブロックコポリマーをエッチングし、前記半導体基板中に均一に間隔のあいたチャネルを形成すること、
を含む方法。 - フォトレジストを前記マット組成物上に配置し、前記マット組成物をエッチングすることをさらに含む、請求項1に記載の方法。
- 前記第一のアクリレート単位が式(1)で表される構造を持つモノマーの重合により生じる
(式中、R1は水素または炭素数1〜10のアルキル基)、
または式(2)で表される構造を持つモノマーの重合により生じる
(式中、R1は水素または炭素数1〜10のアルキル基、R2はC1−10アルキル基、C3−10シクロアルキル基またはC7−10アラルキル基)、
請求項1または2のいずれか1つに記載の方法。 - 前記第二の単位が2−(1,2−ジヒドロシクロブタベンゼン−1−イルオキシ)エチルメタクリレートの重合により生じる、請求項1〜3のいずれか1つに記載の方法。
- 架橋が起きる際に、前記マット組成物が下に示す構造を含む、請求項1〜4のいずれか1つに記載の方法。
- 前記第二の単位が式I−1〜I−20および式M−1〜M−27に示す架橋性モノマーの重合および/または架橋により生じる、請求項1〜5のいずれか1つに記載の方法。
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KR20170058897A (ko) | 2017-05-29 |
US20150184017A1 (en) | 2015-07-02 |
CN104749876A (zh) | 2015-07-01 |
KR20150079465A (ko) | 2015-07-08 |
CN104749876B (zh) | 2020-11-24 |
TW201543146A (zh) | 2015-11-16 |
KR102163900B1 (ko) | 2020-10-12 |
JP2015130496A (ja) | 2015-07-16 |
TWI594071B (zh) | 2017-08-01 |
KR102155018B1 (ko) | 2020-09-11 |
KR20170084001A (ko) | 2017-07-19 |
US9828518B2 (en) | 2017-11-28 |
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