TW202111436A - 阻劑下層膜形成組成物 - Google Patents
阻劑下層膜形成組成物 Download PDFInfo
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- TW202111436A TW202111436A TW109124685A TW109124685A TW202111436A TW 202111436 A TW202111436 A TW 202111436A TW 109124685 A TW109124685 A TW 109124685A TW 109124685 A TW109124685 A TW 109124685A TW 202111436 A TW202111436 A TW 202111436A
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- underlayer film
- resist underlayer
- forming composition
- film forming
- resist
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- LHCGBIFHSCCRRG-UHFFFAOYSA-N dichloroborane Chemical compound ClBCl LHCGBIFHSCCRRG-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940031769 diisobutyl adipate Drugs 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- PQJYOOFQDXGDDS-ZCXUNETKSA-N dinonyl (z)-but-2-enedioate Chemical compound CCCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCCC PQJYOOFQDXGDDS-ZCXUNETKSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- TZPDPYPMOSVWKK-UHFFFAOYSA-N diphenyliodanium;1,1,1,2,2,3,3,4,4-nonafluorobutane Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 TZPDPYPMOSVWKK-UHFFFAOYSA-N 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
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- 230000009977 dual effect Effects 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000000609 electron-beam lithography Methods 0.000 description 1
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- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 description 1
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- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
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- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NOUUUQMKVOUUNR-UHFFFAOYSA-N n,n'-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1NCCNC1=CC=CC=C1 NOUUUQMKVOUUNR-UHFFFAOYSA-N 0.000 description 1
- FMMQDMHSGNXJSQ-UHFFFAOYSA-N n,n-diphenylhydroxylamine Chemical compound C=1C=CC=CC=1N(O)C1=CC=CC=C1 FMMQDMHSGNXJSQ-UHFFFAOYSA-N 0.000 description 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- 229920001778 nylon Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
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- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
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- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
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- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
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- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical class [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
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- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
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- 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
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
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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
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; 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
- G03F7/004—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
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Abstract
本發明為提供一種顯示高蝕刻耐性、良好之乾蝕刻速度比及光學定數,即使對於所謂的段差基板,被覆性亦良好,且嵌入後之膜厚差小,可形成平坦之膜的阻劑下層膜形成組成物。又,提供一種適合在該阻劑下層膜形成組成物之聚合物之製造方法、使用該阻劑下層膜形成組成物之阻劑下層膜、以及半導體裝置之製造方法。成為包含碳原子數6~60之芳香族化合物(A)與下述式(B)表示之化合物的反應生成物及溶劑之阻劑下層膜形成組成物。
(式中,X表示氧原子或氮原子,
Y表示單鍵、氧原子或氮原子,
X與Y可彼此鍵結形成環,
R1
、R2
、R3
及R4
分別獨立表示氫原子、碳數1~20之烷基、碳數3~8之環狀烷基或碳數6~10之芳香族基,
R2
僅於X為氮原子的情況存在,
R4
僅於Y為氮原子的情況存在)。
Description
本發明係關於顯示高蝕刻耐性、良好之乾蝕刻速度比及光學定數,即使對於所謂的段差基板,被覆性亦良好,且嵌入後之膜厚差小,可形成平坦之膜的阻劑下層膜形成組成物、適合在該阻劑下層膜形成組成物之聚合物、使用該阻劑下層膜形成組成物之阻劑下層膜、以及半導體裝置之製造方法。
近年來,於多層阻劑製程用之阻劑下層膜材料,已尋求對於尤其是短波長之曝光,用作抗反射膜,具有適當之光學定數,並且亦一併具有在基板加工之蝕刻耐性,提案有具有包含苯環之重複單位的聚合物的利用(專利文獻1)。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開2004-354554
[發明欲解決之課題]
為了伴隨阻劑圖型之微細化所尋求之阻劑層的薄膜化,已知有至少形成2層阻劑下層膜,並將該阻劑下層膜作為遮罩材使用之微影製程。此係於半導體基板上,設置至少一層之有機膜(下層有機膜)、與至少一層之無機下層膜,並將上層阻劑膜所形成之阻劑圖型作為遮罩,圖型化無機下層膜,將該圖型作為遮罩,進行下層有機膜的圖型化之方法,可形成高寬高比之圖型。作為形成前述至少2層之材料,可列舉有機樹脂(例如丙烯酸樹脂、酚醛樹脂)、與無機系材料(矽樹脂(例如有機聚矽氧烷)、無機矽化合物(例如SiON、SiO2
)等)之組合。進而,於近年來,為了得到1個圖型,進行2次微影與2次蝕刻之雙重圖型化技術已被廣泛適用,在個別的步驟,使用有上述之多層製程。此時,形成最初之圖型後成膜之有機膜中,平坦化段差的特性成為必要。
然而,相對於在被加工基板上所形成之阻劑圖型,有高低差或疏密之所謂的段差基板,亦有藉由阻劑下層膜形成用組成物之被覆性低、嵌入後之膜厚差變大,難以形成平坦之膜的問題。
本發明係鑑於如此之課題解決而完成者,係提供一種係顯示高蝕刻耐性、良好之乾蝕刻速度比及光學定數,即使對於所謂的段差基板,被覆性亦良好,且嵌入後之膜厚差小,可形成平坦之膜的阻劑下層膜形成組成物。又,本發明係以提供一種適合在該阻劑下層膜形成組成物之聚合物、使用該阻劑下層膜形成組成物之阻劑下層膜、以及半導體裝置之製造方法作為目的。
[用以解決課題之手段]
本發明係包含以下。
[1] 一種阻劑下層膜形成組成物,其係包含碳原子數6~60之芳香族化合物(A)與下述式(B)表示之化合物的反應生成物及溶劑。
(式中,X表示氧原子或氮原子,
Y表示單鍵、氧原子或氮原子,
X與Y可彼此鍵結形成環,
R1
、R2
、R3
及R4
分別獨立表示氫原子、碳數1~20之烷基、碳數3~8之環狀烷基或碳數6~10之芳香族基,
R2
僅於X為氮原子的情況存在,
R4
僅於Y為氮原子的情況存在)。
[2] 如[1]所記載之阻劑下層膜形成組成物,其中,前述式(B)中之X及Y為氧原子或氮原子。
[3] 如[1]或[2]所記載之阻劑下層膜形成組成物,其中,前述式(B)表示之化合物為下述式(C)表示之馬來醯亞胺衍生物。
(式中,R1
表示氫原子、碳數1~20之烷基、碳數3~8之環狀烷基,或碳數6~10之芳香族基)。
[4] 如[1]所記載之阻劑下層膜形成組成物,其中,前述芳香族化合物(A)包含1個以上之苯環、萘環、蒽環、芘環或該等之組合。
[5] 如[1]所記載之阻劑下層膜形成組成物,其中,前述芳香族化合物(A)包含2個以上之苯環、萘環、蒽環、芘環或該等之組合。
[6] 如[1]~[5]中任一項所記載之阻劑下層膜形成組成物,其係進一步包含交聯劑。
[7] 如[1]~[6]中任一項所記載之阻劑下層膜形成組成物,其係進一步包含酸及/或酸產生劑。
[8] 如[1]所記載之阻劑下層膜形成組成物,其中,前述溶劑的沸點為160℃以上。
[9] 一種阻劑下層膜,其特徵為包含如[1]~[8]中任一項所記載之阻劑下層膜形成組成物而成之塗佈膜的燒成物。
[10] 一種半導體裝置之製造方法,其係包含:於半導體基板上使用如[1]~[8]中任一項所記載之阻劑下層膜形成組成物,形成阻劑下層膜之步驟、
於所形成之阻劑下層膜之上,形成阻劑膜之步驟、
藉由對於所形成之阻劑膜之光或電子束的照射與顯影,形成阻劑圖型之步驟、
透過所形成之阻劑圖型,蝕刻前述阻劑下層膜,而圖型化之步驟及
透過經圖型化之阻劑下層膜,加工半導體基板之步驟。
[11] 一種碳原子數6~60之芳香族化合物(A)與下述式(C)表示之馬來醯亞胺衍生物的共聚物。
(式中,R1
表示氫原子、碳數1~20之烷基、碳數3~8之環狀烷基或碳數6~10之芳香族基)。
[12] 如[11]所記載之共聚物,其中,前述芳香族化合物(A)包含1個以上之苯環、萘環、蒽環、芘環或該等之組合。
[發明效果]
本發明之阻劑下層膜形成組成物不僅具有高蝕刻耐性、良好之乾蝕刻速度比及光學定數,所得之阻劑下層膜即使對於所謂的段差基板,被覆性亦良好,且嵌入後之膜厚差小,形成平坦之膜,且達成更微細之基板加工。
尤其是本發明之阻劑下層膜形成組成物,對於至少形成2層將阻劑膜厚之薄膜化作為目的之阻劑下層膜,將該阻劑下層膜作為蝕刻遮罩使用之微影製程為有效。
[阻劑下層膜形成組成物]
有關本發明之阻劑下層膜形成組成物,係包含碳原子數6~60之芳香族化合物(A)與下述式(B)表示之化合物的反應生成物、溶劑及其他成分,
(式中,X表示氧原子或氮原子,
Y表示單鍵、氧原子或氮原子,
X與Y可彼此鍵結形成環,
R1
、R2
、R3
及R4
分別獨立表示氫原子、碳數1~20之烷基、碳數3~8之環狀烷基,或碳數6~10之芳香族基,
R2
僅於X為氮原子的情況存在,
R4
僅於Y為氮原子的情況存在)。
以下依序進行說明。
[碳原子數6~60之芳香族化合物(A)]
碳原子數6~60之芳香族化合物(A)
(a)可為如苯、酚、間苯三酚之單環化合物,
(b)可為如萘、二羥基萘之縮合環化合物,
(c)可為如呋喃、噻吩、吡啶、咔唑之雜環化合物,
(d)可為如聯苯、苯基吲哚、9,9-雙(4-羥基苯基)茀、α,α,α’,α’-肆(4-羥基苯基)-p-二甲苯,(a)~(c)之芳香族環以單鍵鍵結之化合物,
(e)可為如苯基萘基胺,以-(CH2
)n
-(n=1~20)、-CH=CH-、-C≡C-、-N=N-、-NH-、-NR-、-NHCO-、-NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-所例示之間距基連結(a)~(d)之芳香族環之化合物。
作為芳香族化合物,可列舉苯、噻吩、呋喃、吡啶、嘧啶、吡嗪、吡咯、噁唑、噻唑、咪唑、萘、蒽、喹啉、咔唑、喹唑啉、嘌呤、中氮茚(Indolizine)、苯并噻吩、苯并呋喃、吲哚、苯基吲哚、吖啶等。
又,上述芳香族化合物(A)可成為包含胺基、羥基(Hydroxyl)或其兩者之芳香族化合物。又,上述芳香族化合物(A)可成為包含芳基胺化合物、酚化合物或其兩者之芳香族化合物。
較佳為芳香族胺或含有酚性羥基之化合物。
作為芳香族胺,可列舉苯胺、二苯基胺、苯基萘基胺、羥基二苯基胺、苯基萘基胺、N,N’-二苯基乙二胺(Ethylenediamine)、N,N’-二苯基-1,4-苯二胺(Phenylenediamine)等。
作為含有酚性羥基之化合物,可列舉酚、二羥基苯、三羥基苯、羥基萘、二羥基萘、三羥基萘、參(4-羥基苯基)甲烷、參(4-羥基苯基)乙烷、1,1,2,2-肆(4-羥基苯基)乙烷、多核酚等。
作為上述多核酚,可列舉二羥基苯、三羥基苯、羥基萘、二羥基萘、三羥基萘、參(4-羥基苯基)甲烷、參(4-羥基苯基)乙烷、2,2’-聯酚,或1,1,2,2-肆(4-羥基苯基)乙烷等。
上述碳原子數6~60之芳香族化合物(A)之氫原子,可被碳原子數1~20之烷基、縮環基、雜環基、羥基、胺基、硝基、醚基、烷氧基、氰基及羧基取代。
作為上述碳原子數1~20之烷基,可列舉可具有亦可不具有取代基之具有直鏈或分枝之烷基,例如可列舉甲基、乙基、n-丙基、異丙基、n-丁基、sec-丁基、tert-丁基、n-戊基、異戊基、新戊基、n-己基、異己基、n-庚基、n-辛基、環己基、2-乙基己基、n-壬基、異壬基、p-tert-丁基環己基、n-癸基、n-十二烷基壬基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基及二十烷基等。較佳為碳原子數1~12之烷基,更佳為碳原子數1~8之烷基,再更佳為碳原子數1~4之烷基。
作為藉由氧原子、硫原子或醯胺鍵中斷之碳原子數1~20之烷基,例如可列舉具有構造單位-CH2
-O-、-CH2
-S-、-CH2
-NHCO-或-CH2
-CONH-者。-O-、-S-、
-NHCO-或-CONH-可於前述烷基中有一單位或二單位以上。藉由-O-、-S-、-NHCO-或-CONH-單位中斷之碳原子數1~20之烷基的具體例,有甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基胺基、乙基羰基胺基、丙基羰基胺基、丁基羰基胺基、甲基胺基羰基、乙基胺基羰基、丙基胺基羰基、丁基胺基羰基等,進而,有甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基或十八烷基,其個別係藉由甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基胺基、乙基羰基胺基、甲基胺基羰基、乙基胺基羰基等取代者。較佳為甲氧基、乙氧基、甲硫基、乙硫基,更佳為甲氧基、乙氧基。
所謂縮環基,係源自縮合環化合物之取代基,具體而言,雖可列舉苯基、萘基、蒽基、菲基、稠四苯基(Naphthacenyl)、苯并菲基(triphenylenyl)、芘基及屈基(chrysenyl),但此等當中,較佳為苯基、萘基、蒽基及芘基。
所謂雜環基,係源自雜環式化合物之取代基,具體而言,雖可列舉噻吩基、呋喃基、吡啶基、嘧啶基、吡嗪基、吡咯基、噁唑基、噻唑基、咪唑基、喹啉基、咔唑基、喹唑啉基、嘌呤基、中氮茚基、苯并噻吩基、苯并呋喃基、吲哚基、吖啶基、異吲哚基、苯并咪唑基、異喹啉基、喹喔啉基、噌啉基、蝶啶基、色烯基(苯并吡喃基)、異色烯基(苯并吡喃基)、氧雜蒽(xanthene)基、噻唑基、吡唑基、咪唑啉基、吖嗪基,但此等當中,較佳為噻吩基、呋喃基、吡啶基、嘧啶基、吡嗪基、吡咯基、噁唑基、噻唑基、咪唑基、喹啉基、咔唑基、喹唑啉基、嘌呤基、中氮茚基、苯并噻吩基、苯并呋喃基、吲哚基及吖啶基,最佳為噻吩基、呋喃基、吡啶基、嘧啶基、吡咯基、噁唑基、噻唑基、咪唑基及咔唑基。
尚,以上之芳香族化合物可藉由單鍵或間距基連結。
作為間距基之例,可列舉-(CH2
)n
-(n=1~20)、-CH<、-CH=CH-、-C≡C-、-N=N-、-NH-、-NR-、-NHCO-、
-NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-之一種或二種以上的組合。此等之間距基可連結2個以上。
上述芳香族化合物(A)較佳為包含1個以上之苯環、萘環、蒽環、芘環或該等之組合,更佳為包含2個以上之苯環、萘環、蒽環、芘環或該等之組合。
上述芳香族化合物(A)雖可為1種類或2種類以上,但較佳為1種或2種。
[式(B)表示之化合物]
化合物(B)係以下述式表示。
(式中,X表示氧原子或氮原子,
Y表示單鍵、氧原子或氮原子,
X與Y可彼此鍵結形成環,
R1
、R2
、R3
及R4
分別獨立表示氫原子、碳數1~20之烷基、碳數3~8之環狀烷基,或碳數6~10之芳香族基,
R2
僅於X為氮原子的情況存在,
R4
僅於Y為氮原子的情況存在)。
作為碳數1~20之烷基,可列舉可具有亦可不具有取代基之具有直鏈或分枝之烷基,例如可列舉甲基、乙基、n-丙基、異丙基、n-丁基、sec-丁基、tert-丁基、n-戊基、異戊基、新戊基、n-己基、異己基、n-庚基、n-辛基、環己基、2-乙基己基、n-壬基、異壬基、p-tert-丁基環己基、n-癸基、n-十二烷基壬基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基及二十烷基等。較佳為碳原子數1~12之烷基,更佳為碳原子數1~8之烷基,再更佳為碳原子數1~4之烷基。
作為碳數3~8之環狀烷基,可列舉可具有亦可不具有取代基之環丙基、環丁基、環戊基、環己基、環庚基、環辛基等。
作為碳數6~10之芳香族基,可列舉可具有亦可不具有取代基之從苯、甲苯、二甲苯、均三甲苯、異丙苯、苯乙烯、茚、萘、薁、蒽、菲等之芳香族化合物去除1個氫原子之基。較佳為苄基、苯基。
在式(B),R1
始終存在。R2
雖於X為氮原子時存在,但於X為氧原子時,或X與Y彼此鍵結形成環時並不存在。R3
雖於Y為氧原子或氮原子時存在,但於Y為單鍵時並不存在。R4
雖於Y為氮原子時存在,但於Y為氧原子或單鍵時,或X與Y彼此鍵結形成環時並不存在。
較佳為前述式(B)中之X及Y為氧原子或氮原子。
較佳為化合物(B)係式(B)中之X為氮原子,Y為單鍵,X與Y彼此鍵結形成環,且不存在R2
、R3
及R4
之化合物。
亦即,前述式(B)表示之化合物為下述式(C)表示之馬來醯亞胺衍生物。
(式中,R1
表示氫原子、碳數1~20之烷基、碳數3~8之環狀烷基或碳數6~10之芳香族基)。
於此,對於碳數1~20之烷基、碳數3~8之環狀烷基、碳數6~10之芳香族基,係如上述。
上述化合物(B)雖可為1種類或2種類以上,但較佳為1種或2種。
[反應生成物]
藉由使上述芳香族化合物(A)、與上述式(B)表示之化合物所具有之碳間雙鍵進行反應,可得到上述式(B)表示之化合物的2個碳原子連結2個上述芳香族化合物(A)之反應生成物(聚合物)。此反應生成物係上述芳香族化合物(A)與上述式(B)表示之化合物(較佳為式(C)表示之馬來醯亞胺衍生物)的共聚物。尚,如上述,由於上述芳香族化合物(A)與上述式(B)表示之化合物可分別選擇1種類或2種類以上採用,故上述聚合物亦可定為多元共聚物。又,可使上述芳香族化合物(A)與上述式(B)表示之化合物以外之單體,共聚合於不損害本發明之效果的範圍的量(例如未滿50莫耳%、未滿30莫耳%、未滿20莫耳%、未滿10莫耳%或未滿5莫耳%)。
作為反應所使用之酸觸媒,例如使用硫酸、磷酸、高氯酸等之無機酸類、p-甲苯磺酸、p-甲苯磺酸一水合物、甲烷磺酸等之有機磺酸類、蟻酸、草酸等之羧酸類。酸觸媒的使用量係藉由使用之酸類的種類進行各種選擇。通常相對於芳香族化合物(A)100質量份,為0.001至10000質量份,較佳為0.01至1000質量份,更佳為0.1至100質量份。
上述之縮合反應與加成反應即使無溶媒雖亦可進行,但通常使用溶媒進行。作為溶媒,若為不阻礙反應者,則可全部使用。例如可列舉1,2-二甲氧基乙烷、二乙二醇二甲基醚、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、四氫呋喃、二噁烷等之醚類。
反應時,如有必要可添加阻聚劑(自由基捕獲劑)。作為聚合起始劑之具體例,可列舉2,6-二異丁基酚、3,5-二-tert-丁基酚、3,5-二-tert-丁基甲酚、對苯二酚、對苯二酚單甲基醚、鄰苯三酚(Pyrogallol)、tert-丁基鄰苯二酚、4-甲氧基-1-萘酚等。添加阻聚劑時,其添加量相對於全固體成分,較佳為1質量%以下。
反應溫度通常為40℃至200℃。反應時間雖可藉由反應溫度進行各種選擇,但通常為30分鐘至50小時左右。
如以上進行所得之聚合物的重量平均分子量Mw通常為500至1,000,000或600至500,000。
對於適合在本發明使用之反應生成物,以實施例進行說明。
[溶劑]
作為有關本發明之阻劑下層膜形成組成物的溶劑,若為可溶解上述反應生成物之溶劑,則可不特別限制使用。尤其是有關本發明之阻劑下層膜形成組成物由於是以均一之溶液狀態使用者,故考量其塗佈性能時,推薦於微影步驟併用一般所使用之溶劑。
作為這般的溶劑,例如可列舉甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、丙二醇、丙二醇單甲基醚、丙二醇單乙基醚、甲基異丁基甲醇(Carbinol)、丙二醇單丁基醚、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、丙二醇單丁基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯、丙酮酸甲酯、丙酮酸乙酯、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚、乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、乙二醇單丙基醚乙酸酯、乙二醇單丁基醚乙酸酯、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二丙基醚、二乙二醇二丁基醚、丙二醇單甲基醚、丙二醇二甲基醚、丙二醇二乙基醚、丙二醇二丙基醚、丙二醇二丁基醚、乳酸乙酯、乳酸丙酯、乳酸異丙酯、乳酸丁酯、乳酸異丁酯、甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸異丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊酯、甲酸異戊酯、乙酸甲酯、乙酸乙酯、乙酸戊酯、乙酸異戊酯、乙酸己酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、丙酸丁酯、丙酸異丁酯、丁酸甲酯、丁酸乙酯、丁酸丙酯、丁酸異丙酯、丁酸丁酯、丁酸異丁酯、羥基乙酸乙酯、2-羥基-2-甲基丙酸乙酯、3-甲氧基-2-甲基丙酸甲酯、2-羥基-3-甲基丁酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲氧基丙基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基丙酸酯、3-甲基-3-甲氧基丁基丁酸酯、乙醯乙酸甲酯、甲苯、二甲苯、甲基乙基酮、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、環己酮、N、N-二甲基甲醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、4-甲基-2-戊醇及γ-丁內酯等。此等之溶劑可單獨或以二種以上的組合使用。
又,亦可使用WO2018/131562A1所記載之下述化合物。
(式(i)中之R1
、R2
及R3
係表示可分別被氫原子、氧原子、硫原子或醯胺鍵中斷之碳原子數1~20之烷基,可彼此相同,亦可彼此相異,並可彼此鍵結形成環構造)。
作為碳原子數1~20之烷基,可列舉可具有亦可不具有取代基之具有直鏈或分枝之烷基,例如可列舉甲基、乙基、n-丙基、異丙基、n-丁基、sec-丁基、tert-丁基、n-戊基、異戊基、新戊基、n-己基、異己基、n-庚基、n-辛基、環己基、2-乙基己基、n-壬基、異壬基、p-tert-丁基環己基、n-癸基、n-十二烷基壬基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基及二十烷基等。較佳為碳原子數1~12之烷基,更佳為碳原子數1~8之烷基,再更佳為碳原子數1~4之烷基。
作為藉由氧原子、硫原子或醯胺鍵中斷之碳原子數1~20之烷基,例如可列舉含有構造單位-CH2
-O-、-CH2
-S-、-CH2
-NHCO-或-CH2
-CONH-者。-O-、-S-、
-NHCO-或-CONH-可於前述烷基中有一單位或二單位以上。藉由-O-、-S-、-NHCO-或-CONH-單位中斷之碳原子數1~20之烷基之具體例,有甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基胺基、乙基羰基胺基、丙基羰基胺基、丁基羰基胺基、甲基胺基羰基、乙基胺基羰基、丙基胺基羰基、丁基胺基羰基等,進而,有甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基或十八烷基,其分別為藉由甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基胺基、乙基羰基胺基、甲基胺基羰基、乙基胺基羰基等取代者。較佳為甲氧基、乙氧基、甲硫基、乙硫基,更佳為甲氧基、乙氧基。
此等之溶劑由於為比較高沸點,故為了對阻劑下層膜形成組成物賦予高嵌入性或高平坦化性亦有效。
此等之溶劑可單獨或以二種以上的組合使用。此等之溶劑當中,較佳為沸點為160℃以上者,較佳為丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、乳酸乙酯、乳酸丁酯、環己酮、3-甲氧基-N,N-二甲基丙醯胺、N,N-二甲基異丁基醯胺、2,5-二甲基己烷-1,6-二基二乙酸酯(DAH;cas,89182-68-3)及1,6-二乙醯氧基己烷(cas,6222-17-9)等。特佳為丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、N,N-二甲基異丁基醯胺。
[交聯劑成分]
本發明之阻劑下層膜形成組成物可包含交聯劑成分。作為其交聯劑,可列舉三聚氰胺系、取代脲系,或該等之聚合物系等。較佳為具有至少2個交聯形成取代基之交聯劑,甲氧基甲基化甘脲(例如四甲氧基甲基甘脲)、丁氧基甲基化甘脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯胍胺、丁氧基甲基化苯胍胺、甲氧基甲基化脲、丁氧基甲基化脲,或甲氧基甲基化硫脲等之化合物。又,亦可使用此等之化合物的縮合體。
又,作為上述交聯劑,可使用耐熱性高之交聯劑。作為耐熱性高之交聯劑,可優選使用含有於分子內具有芳香族環(例如苯環、萘環)之交聯形成取代基的化合物。
此化合物,可列舉具有下述式(4)之部分構造的化合物,或具有下述式(5)之重複單位的聚合物或寡聚物。
上述R11
、R12
、R13
及R14
為氫原子或碳數1至10之烷基,此等之烷基可使用上述之例示。
上述化合物可作為旭有機材工業股份有限公司、本州化學工業股份有限公司的製品取得。例如上述交聯劑當中,式(4-24)之化合物可作為旭有機材工業股份有限公司、商品名TM-BIP-A取得。
交聯劑的添加量雖因使用之塗佈溶媒、使用之基底基板、所要求之溶液黏度、所要求之膜形狀等而變動,但相對於全固體成分,為0.001至80質量%,較佳為 0.01至50質量%,更佳為0.05至40質量%。此等交聯劑雖亦有引起因自縮合導致之交聯反應的情況,但於本發明之上述反應生成物中存在交聯性取代基時,可與該等之交聯性取代基引起交聯反應。
[酸及/或酸產生劑]
本發明之阻劑下層膜形成組成物可含有酸及/或酸產生劑。
作為酸,例如可列舉p-甲苯磺酸、三氟甲烷磺酸、吡啶鎓p-甲苯磺酸、吡啶鎓酚磺酸、水楊酸、5-磺基水楊酸、4-酚磺酸、樟腦磺酸、4-氯苯磺酸、苯二磺酸、1-萘磺酸、檸檬酸、苯甲酸、羥基苯甲酸、萘羧酸等。
酸可僅使用一種,或亦可組合二種以上使用。摻合量相對於全固體成分,通常為0.0001至20質量%,較佳為0.0005至10質量%,更佳為0.01至3質量%。
作為酸產生劑,可列舉熱酸產生劑或光酸產生劑。
作為熱酸產生劑,可列舉2,4,4,6-四溴環己二烯酮(Hexadienone)、安息香甲苯磺酸酯、2-硝基苄基甲苯磺酸酯、K-PURE[註冊商標]CXC-1612、同CXC-1614、同TAG-2172、同TAG-2179、同TAG-2678、同TAG2689、同TAG2700(King Industries公司製)及SI-45、SI-60、SI-80、SI-100、SI-110、SI-150(三新化學工業(股)製)其他有機磺酸烷基酯等。
光酸產生劑於阻劑之曝光時產生酸。因此,可進行下層膜之酸性度的調整。此係用以將下層膜的酸性度與上層之阻劑的酸性度調合之一方法。又,藉由下層膜之酸性度的調整,可進行上層所形成之阻劑之圖型形狀的調整。
作為本發明之阻劑下層膜形成組成物所包含之光酸產生劑,可列舉鎓鹽化合物、磺醯亞胺化合物及二磺醯基重氮甲烷化合物等。
作為鎓鹽化合物,可列舉二苯基碘鎓六氟磷酸酯、二苯基碘鎓三氟甲烷磺酸酯、二苯基碘鎓九氟正丁烷磺酸酯、二苯基碘鎓全氟正辛烷磺酸酯、二苯基碘鎓樟腦磺酸酯、雙(4-tert-丁基苯基)碘鎓樟腦磺酸酯及雙(4-tert-丁基苯基)碘鎓三氟甲烷磺酸酯等之碘鎓鹽化合物及三苯基鋶六氟銻酸鹽、三苯基鋶九氟正丁烷磺酸酯、三苯基鋶樟腦磺酸酯及三苯基鋶三氟甲烷磺酸酯等之鋶鹽化合物等。
作為磺醯亞胺化合物,例如可列舉N-(三氟甲烷磺醯基氧基)琥珀醯亞胺(Succinimide)、N-(九氟正丁烷磺醯基氧基)琥珀醯亞胺、N-(樟腦磺醯基氧基)琥珀醯亞胺及N-(三氟甲烷磺醯基氧基)萘醯亞胺等。
作為二磺醯基重氮甲烷化合物,例如可列舉雙(三氟甲基磺醯基)重氮甲烷、雙(環己基磺醯基)重氮甲烷、雙(苯基磺醯基)重氮甲烷、雙(p-甲苯磺醯基)重氮甲烷、雙(2,4-二甲基苯磺醯基)重氮甲烷及甲基磺醯基-p-甲苯磺醯基重氮甲烷等。
酸產生劑可僅使用一種,或亦可組合二種以上使用。
使用酸產生劑時,作為其比例,相對於阻劑下層膜形成組成物的固體成分100質量份,為0.01至5質量份或0.1至3質量份或0.5至1質量份。
[其他成分]
於本發明之阻劑下層膜形成組成物,並無針孔或條紋等之發生,為了進一步提昇對於表面凹凸之塗佈性,可摻合界面活性劑。作為界面活性劑,例如可列舉聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯十六烷基醚、聚氧乙烯油醯基醚等之聚氧乙烯烷基醚類、聚氧乙烯辛基酚醚、聚氧乙烯壬基酚醚等之聚氧乙烯烷基烯丙基醚類、聚氧乙烯•聚氧丙烯嵌段共聚物類、山梨糖醇單月桂酸酯、山梨糖醇單棕櫚酸酯、山梨糖醇單硬脂酸酯、山梨糖醇單油酸酯、山梨糖醇三油酸酯、山梨糖醇三硬脂酸酯等之山梨糖醇脂肪酸酯類、聚氧乙烯山梨糖醇單月桂酸酯、聚氧乙烯山梨糖醇單棕櫚酸酯、聚氧乙烯山梨糖醇單硬脂酸酯、聚氧乙烯山梨糖醇三油酸酯、聚氧乙烯山梨糖醇三硬脂酸酯等之聚氧乙烯山梨糖醇脂肪酸酯類等之非離子系界面活性劑、EFTOP EF301、EF303、EF352(Thochem Products股份有限公司製、商品名)、MEGAFAC F171、F173、R-40、R-40N、R-40LM(DIC股份有限公司製、商品名)、Fluorad FC430、FC431(住友3M股份有限公司製、商品名)、Asahiguard AG710、Surflon S-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子股份有限公司製、商品名)等之氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業股份有限公司製)等。此等之界面活性劑的摻合量相對於阻劑下層膜材料之全固體成分,通常為2.0質量%以下,較佳為1.0質量%以下。此等之界面活性劑可單獨使用,亦可以二種以上的組合使用。使用界面活性劑時,作為其比例,相對於阻劑下層膜形成組成物之固體成分100質量份,為0.0001至5質量份或0.001至1質量份或0.01至0.5質量份。
於本發明之阻劑下層膜形成組成物,可添加吸光劑、流變調整劑、接著輔助劑等。流變調整劑有效提昇下層膜形成組成物的流動性。接著輔助劑對提昇半導體基板或阻劑與下層膜的密著性有效。
作為吸光劑,例如可適合使用「工業用色素之技術與市場」(CMC出版)或「染料便覽」(有機合成化學協會編)所記載之市售的吸光劑,例如C.I.Disperse Yellow 1, 3, 4, 5, 7, 8, 13, 23, 31, 49, 50, 51, 54, 60, 64, 66, 68, 79, 82, 88, 90, 93, 102, 114,及124; C.I.Disperse Orange1, 5, 13, 25, 29, 30, 31, 44, 57, 72,及73; C.I.Disperse Red 1, 5, 7, 13, 17, 19, 43, 50, 54, 58, 65, 72, 73, 88, 117, 137, 143, 199,及210; C.I.Disperse Violet 43; C.I.Disperse Blue 96; C.I.Fluorescent Brightening Agent 112, 135及163; C.I.Solvent Orange2,及45; C.I.Solvent Red 1, 3, 8, 23, 24, 25, 27,及49; C.I.Pigment Green 10; C.I.Pigment Brown 2等。上述吸光劑通常相對於阻劑下層膜形成組成物之全固體成分,係以10質量%以下,較佳為以5質量%以下的比例摻合。
流變調整劑主要係提昇阻劑下層膜形成組成物之流動性,尤其是在烘烤步驟,以阻劑下層膜之膜厚均一性的提昇或提高對孔內部之阻劑下層膜形成組成物的填充性為目的而添加。作為具體例,可列舉二甲基苯二甲酸酯、二乙基苯二甲酸酯、二異丁基苯二甲酸酯、二己基苯二甲酸酯、丁基異癸基苯二甲酸酯等之苯二甲酸衍生物、二正丁基己二酸酯、二異丁基己二酸酯、二異辛基己二酸酯、辛基癸基己二酸酯等之己二酸衍生物、二正丁基馬來酸酯、二乙基馬來酸酯、二壬基馬來酸酯等之馬來酸衍生物、甲基油酸酯、丁基油酸酯、四氫糠基油酸酯等之油酸衍生物,或正丁基硬脂酸酯、甘油基硬脂酸酯等之硬脂酸衍生物。此等之流變調整劑相對於阻劑下層膜形成組成物之全固體成分,通常以未滿30質量%的比例摻合。
接著輔助劑主要係提昇基板或阻劑與阻劑下層膜形成組成物的密著性,尤其是在顯影,用以使阻劑不會剝離的方式為目的而添加。作為具體例,可列舉三甲基氯矽烷、二甲基羥甲基氯矽烷、甲基二苯基氯矽烷、氯甲基二甲基氯矽烷等之氯矽烷類、三甲基甲氧基矽烷、二甲基二乙氧基矽烷、甲基二甲氧基矽烷、二甲基羥甲基乙氧基矽烷、二苯基二甲氧基矽烷、苯基三乙氧基矽烷等之烷氧基矽烷類、六甲基二矽氮烷、N,N’-雙(三甲基矽烷基)脲、二甲基三甲基矽烷基胺、三甲基矽烷基咪唑等之矽氮烷類、羥甲基三氯矽烷、γ-氯丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷等之矽烷類、苯并三唑、苯并(Benz)咪唑、吲唑、咪唑、2-巰基苯并(Benz)咪唑、2-巰基苯并噻唑、2-巰基苯并噁唑、脲唑、硫脲嘧碇(Thiouracil)、巰基咪唑、巰基嘧啶等之雜環式化合物,或1,1-二甲基脲、1,3-二甲基脲等之脲或硫脲化合物。此等之接著輔助劑相對於阻劑下層膜形成組成物之全固體成分,通常係以未滿5質量%,較佳為以未滿2質量%的比例摻合。
有關本發明之阻劑下層膜形成組成物的固體成分通常定為0.1至70質量%,較佳為定為0.1至60質量%。固體成分係從阻劑下層膜形成組成物去除溶劑之全成分的含有比例。在固體成分中之上述反應生成物的比例以1至100質量%、1至99.9質量%、50至99.9質量%、50至95質量%、50至90質量%的順序較佳。
評估阻劑下層膜形成組成物是否為均一之溶液狀態的尺度之一雖為觀察特定之微濾器的通過性,但有關本發明之阻劑下層膜形成組成物通過孔徑0.1μm之微濾器,呈現均一之溶液狀態。
作為上述微濾器材質,雖可列舉PTFE(聚四氟乙烯)、PFA(四氟乙烯•全氟烷基乙烯基醚共聚物)等之氟系樹脂、PE(聚乙烯)、UPE(超高分子量聚乙烯)、PP(聚丙烯)、PSF(聚碸)、PES(聚醚碸)、尼龍,但較佳為PTFE (聚四氟乙烯)製。
[阻劑下層膜及半導體裝置之製造方法]
以下,針對使用有關本發明之阻劑下層膜形成組成物之阻劑下層膜及半導體裝置之製造方法,進行說明。
於半導體裝置之製造所使用之基板(例如矽晶圓基板、矽/二氧化矽被覆基板、矽氮化物基板、玻璃基板、ITO基板、聚醯亞胺基板及低介電常數材料(low-k材料)被覆基板等)之上,藉由旋轉器、塗佈機等之適當的塗佈方法,塗佈本發明之阻劑下層膜形成組成物,然後,藉由進行燒成,形成阻劑下層膜。作為燒成之條件,可從燒成溫度80℃至400℃、燒成時間0.3至60分鐘當中適當選擇。較佳為燒成溫度150℃至350℃、燒成時間0.5至2分鐘。於此,作為所形成之下層膜的膜厚,例如為10至1000nm或20至500nm或30至400nm或50至300nm。
又,亦可於有關本發明之有機阻劑下層膜上形成無機阻劑下層膜(硬遮罩)。例如,除了將WO2009/104552A1所記載之含有矽之阻劑下層膜(無機阻劑下層膜)形成組成物以旋塗形成之方法至之外,亦可將Si系之無機材料膜以CVD法等形成。
又,藉由將有關本發明之阻劑下層膜形成組成物,塗佈在具有:具有段差之部分與不具有段差之部分的半導體基板(所謂的段差基板)上,並進行燒成,可形成具有該段差之部分與不具有段差之部分的段差為3~70nm的範圍內之阻劑下層膜。
接著,於其阻劑下層膜之上形成阻劑膜,例如光阻劑之層。光阻劑之層的形成可藉由周知之方法,亦即對光阻劑組成物溶液的下層膜上之塗佈及燒成來進行。作為光阻劑的膜厚,例如為50至10000nm或100至2000nm或200至1000nm。
作為阻劑下層膜之上所形成之光阻劑,若為對曝光所使用之光進行感光者,則並未特別限定。負型光阻劑及正型光阻劑皆可使用。有包含酚醛樹脂與1,2-重氮萘醌磺酸酯而成之正型光阻劑、包含具有藉由酸分解,提昇鹼溶解速度之基的黏結劑與光酸產生劑而成之化學增幅型光阻劑、包含藉由酸分解,提昇光阻劑之鹼溶解速度的低分子化合物與鹼可溶性黏結劑與光酸產生劑而成之化學增幅型光阻劑,及包含具有藉由酸分解,提昇鹼溶解速度之基的黏結劑與藉由酸分解,提昇光阻劑的鹼溶解速度的低分子化合物與光酸產生劑而成之化學增幅型光阻劑等。例如可列舉Shipley公司製商品名APEX-E、住友化學工業股份有限公司製商品名PAR710及信越化學工業股份有限公司製商品名SEPR430等。又,例如可列舉如Proc. SPIE, Vol.3999, 330-334(2000)、Proc. SPIE, Vol.3999, 357-364(2000),或如Proc. SPIE, Vol.3999, 365-374(2000)所記載之含氟原子聚合物系光阻劑。
接著,藉由光或電子束之照射與顯影形成阻劑圖型。首先,通過指定之遮罩進行曝光。曝光係使用近紫外線、遠紫外線,或極端紫外線(例如,EUV(波長13.5nm))等。具體而言,可使用KrF準分子雷射(波長248nm)、ArF準分子雷射(波長193nm)及F2
準分子雷射(波長157nm)等。此等當中,較佳為ArF準分子雷射(波長193nm)及EUV(波長13.5nm)。曝光後,如有必要亦可進行曝光後加熱(post exposure bake)。曝光後加熱可係以從加熱溫度70℃至150℃、加熱時間0.3至10分鐘適當選擇的條件進行。
又,於本發明,作為阻劑,可變更為光阻劑使用電子束微影用阻劑。作為電子束阻劑,負型、正型皆可使用。有包含酸產生劑與具有藉由酸分解,使鹼溶解速度變化之基的黏結劑而成之化學增幅型阻劑、包含鹼可溶性黏結劑與酸產生劑與藉由酸分解,使阻劑的鹼溶解速度變化之低分子化合物而成之化學增幅型阻劑、包含酸產生劑與具有藉由酸分解,使鹼溶解速度變化之基的黏結劑與藉由酸分解,使阻劑的鹼溶解速度變化之低分子化合物而成之化學增幅型阻劑、包含具有藉由電子束分解,使鹼溶解速度變化之基的黏結劑而成之非化學增幅型阻劑、包含具有藉由電子束切斷,使鹼溶解速度變化之部位的黏結劑而成之非化學增幅型阻劑等。使用此等之電子束阻劑的情況,亦與將照射源作為電子束,使用光阻劑的情況相同,可形成阻劑圖型。
接著,藉由顯影液進行顯影。藉此,使用例如正型光阻劑時,去除經曝光之部分的光阻劑,而形成光阻劑的圖型。
作為顯影液,係將氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物之水溶液、氫氧化四甲基銨、氫氧化四乙基銨、膽鹼等之氫氧化四級銨之水溶液、乙醇胺、丙基胺、乙二胺等之胺水溶液等之鹼性水溶液作為例列舉。進而,亦可於此等之顯影液加入界面活性劑等。作為顯影的條件,可從溫度5至50℃、時間10至600秒適當選擇。
而且,將如此進行所形成之光阻劑(上層)之圖型作為保護膜,進行無機下層膜(中間層)的去除,接著,將包含經圖型化之光阻劑及無機下層膜(中間層)而成之膜作為保護膜,進行有機下層膜(下層)的去除。最後,將經圖型化之無機下層膜(中間層)及有機下層膜(下層)作為保護膜,進行半導體基板之加工。
首先,將去除光阻劑之部分的無機下層膜(中間層)藉由乾蝕刻去掉,而使半導體基板露出。於無機下層膜之乾蝕刻,可使用四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷、一氧化碳、氬、氧、氮、六氟化硫、二氟甲烷、三氟化氮及三氟化氯、氯、三氯硼烷及二氯硼烷等之氣體。於無機下層膜之乾蝕刻,較佳為使用鹵素系氣體,更佳為藉由氟系氣體。作為氟系氣體,例如可列舉四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷及二氟甲烷(CH2
F2
)等。
然後,將包含經圖型化之光阻劑及無機下層膜而成之膜作為保護膜,進行有機下層膜的去除。有機下層膜(下層)較佳為藉由由氧系氣體之乾蝕刻進行。係因為大量包含矽原子之無機下層膜,於藉由氧系氣體之乾蝕刻難以去除。
最後進行半導體基板之加工。半導體基板之加工較佳為藉由由氟系氣體之乾蝕刻進行。
作為氟系氣體,例如可列舉四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷及二氟甲烷(CH2
F2
)等。
又,可於阻劑下層膜的上層,於光阻劑的形成前形成有機系之抗反射膜。作為於此使用之抗反射膜組成物,並未特別限制,目前為止,可從在微影製程所慣用者當中任意選擇使用,又,慣用之方法,例如可進行藉由旋轉器、塗佈機之塗佈及藉由燒成進行抗反射膜的形成。
於本發明,可於基板上成膜有機下層膜後,並於其上成膜無機下層膜,進而於其上被覆光阻劑。藉此,光阻劑的圖型寬度變狹小,即使為了防止圖型倒塌,薄化光阻劑被覆的情況,亦藉由選擇適當之蝕刻氣體,使得基板之加工變可能。例如,將相對於光阻劑成為非常快速之蝕刻速度的氟系氣體作為蝕刻氣體,可於阻劑下層膜進行加工,且將相對於無機下層膜成為非常快速之蝕刻速度的氟系氣體作為蝕刻氣體,使用基板之加工變可能,進而,將相對於有機下層膜成為非常快速之蝕刻速度的氧系氣體作為蝕刻氣體,可進行基板之加工。
藉由阻劑下層膜形成組成物形成之阻劑下層膜,又,藉由在微影製程使用之光的波長,係具有對於該光之吸收的情況。而且,這般的情況下,可用作具有防止來自基板之反射光的效果之抗反射膜。進而,於本發明之阻劑下層膜形成組成物所形成之下層膜,係亦可用作硬遮罩者。本發明之下層膜亦可作為用以防止基板與光阻劑的相互作用之層、具有防止對光阻劑所使用之材料或對光阻劑之曝光時所生成之物質的基板的不良作用之層、具有防止對於加熱燒成時從基板所生成之物質之上層光阻劑的擴散的機能之層,及用以減低藉由半導體基板介質體層之光阻劑層的毒害效果之阻隔層等使用。
又,藉由阻劑下層膜形成組成物形成之下層膜係適用在於雙重金屬鑲嵌(Dual Damascene)製程使用之通孔所形成之基板,可將孔作為可無間隙填充之嵌入材料使用。又,亦可作為用以平坦化有凹凸之半導體基板的表面之平坦化材料使用。
[實施例]
以下,雖將本發明之阻劑下層膜形成組成物的具體例使用下述實施例進行說明,但並非藉此而限定本發明者。
顯示於下述合成例所得之反應生成物的重量平均分子量的測定所使用之裝置等。
裝置:東曹股份有限公司製HLC-8320GPC
GPC管柱:TSKgel Super-MultiporeHZ-N(2本)
管柱溫度:40℃
流量:0.35ml/分鐘
溶離液:THF
標準試料:聚苯乙烯(昭和電工股份有限公司)
<合成例1>
於丙二醇單甲基醚(以下,於本說明書簡稱為PGME) 16.75g,添加商品名TEP-TPA(旭有機材工業股份有限公司製)5.00g、N-環己基馬來醯亞胺(東京化成工業股份有限公司製)7.55g及作為觸媒之甲烷磺酸4.05g後,於140℃使其反應7小時,而得到包含反應生成物之溶液。在PGME對30質量%溶液稀釋後,使用甲醇/水混合溶媒(200g)使其再沉澱。過濾所得之沉澱物,以減壓乾燥機60℃、乾燥24小時,而得到作為目的之聚合物。
進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為11,500。所得之反應生成物推定為具有下述式(1)表示之構造單位的共聚物。
<合成例2>
於PGME17.22g添加商品名TEP-TPA(旭有機材工業股份有限公司製)7.00g、N-乙基馬來醯亞胺(東京化成工業股份有限公司製)7.38g及作為觸媒之甲烷磺酸2.84g後,於140℃使其反應7小時,而得到包含反應生成物之溶液。在PGME對30質量%溶液稀釋後,使用甲醇/水混合溶媒(200g、質量混合比50/50)使其再沉澱。過濾所得之沉澱物,以減壓乾燥機60℃、乾燥24小時,而得到作為目的之聚合物。進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為9,000。所得之反應生成物推定為具有下述式(2)表示之構造單位的共聚物。
<合成例3>
於PGME20.06g添加2,2’-二羥基聯苯(東京化成工業股份有限公司製)8.00g、N-環己基馬來醯亞胺(東京化成工業股份有限公司製)7.70g、作為觸媒之甲烷磺酸4.13g及作為自由基捕獲劑之對苯二酚0.24g後,於140℃使其反應20小時,而得到包含反應生成物之溶液。在PGME對30質量%溶液稀釋後,使用甲醇/水混合溶媒(600g、質量混合比50/50)使其再沉澱。過濾所得之沉澱物,以減壓乾燥機60℃、乾燥24小時,而得到作為目的之聚合物。在PGME對20質量%溶液調整後,加入陰離子交換樹脂(製品名:DOWEX[註冊商標] MONOSPHERE[註冊商標]550A、MUROMACHI TECHNOS股份有限公司)16.00g與陽離子交換樹脂(製品名:Amberlite[註冊商標]15JWET、奧加諾股份有限公司)16.00g,以25℃至30℃攪拌4小時後進行過濾。
進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為680。所得之反應生成物推定為具有下述式(3)表示之構造單位的共聚物。
<合成例4>
於PGME21.28g添加二苯基胺(東京化成工業股份有限公司製)8.00g、N-環己基馬來醯亞胺(東京化成工業股份有限公司製)8.47g、作為觸媒之甲烷磺酸4.54g及作為自由基捕獲劑之對苯二酚0.26g後,以140℃使其反應20小時,而得到包含反應生成物之溶液。在PGME對30質量%溶液稀釋後,使用甲醇/水混合溶媒(600g、質量混合比70/30)使其再沉澱。過濾所得之沉澱物,以減壓乾燥機60℃、乾燥24小時,而得到作為目的之聚合物。
進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為1,360。所得之反應生成物推定為具有下述式(4)表示之構造單位的共聚物。
<合成例5>
於丙二醇單甲基醚乙酸酯(以下,於本說明書簡稱為PGMEA)167.27g,添加N-苯基-1-萘基胺(東京化成工業股份有限公司製)50.00g、N-環己基馬來醯亞胺(東京化成工業股份有限公司製)20.43g、作為觸媒之甲烷磺酸21.91g及作為自由基捕獲劑之對苯二酚1.26g後,以140℃使其反應24小時,而得到包含反應生成物之溶液。使用甲醇(2,300g)使其再沉澱。過濾所得之沉澱物,以減壓乾燥機60℃、乾燥24小時,而得到作為目的之聚合物。在PGMEA對20質量%溶液調整後,加入陰離子交換樹脂(製品名:DOWEX[註冊商標]MONOSPHERE[註冊商標] 550A、MUROMACHI TECHNOS股份有限公司)70.00g與陽離子交換樹脂(製品名:Amberlite[註冊商標]15JWET、奧加諾股份有限公司)70.00g,於25℃至30℃攪拌4小時後進行過濾。
進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為2,000。所得之反應生成物推定為具有下述式(5)表示之構造單位的共聚物。
<合成例6>
於PGME54.91g添加咔唑(東京化成工業股份有限公司製)15.00g、N-環己基馬來醯亞胺(東京化成工業股份有限公司製)8.04g、作為觸媒之甲烷磺酸8.62g及作為自由基捕獲劑之對苯二酚0.49g後,以140℃使其反應23小時,而得到包含反應生成物之溶液。使用甲醇(2,800g)使其再沉澱。過濾所得之沉澱物,以減壓乾燥機60℃、乾燥24小時,而得到作為目的之聚合物。在PGMEA對20質量%溶液調整後,加入陰離子交換樹脂(製品名:DOWEX[註冊商標]MONOSPHERE[註冊商標]550A、MUROMACHI TECHNOS股份有限公司)23.00g與陽離子交換樹脂(製品名:Amberlite[註冊商標]15JWET、奧加諾股份有限公司) 23.00g,於25℃至30℃攪拌4小時後進行過濾。
進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為6,000。所得之反應生成物推定為具有下述式(6)表示之構造單位的共聚物。
<合成例7>
於PGMEA292g添加乙基咔唑(東京化成工業股份有限公司製)50.0g、馬來醯亞胺(東京化成工業股份有限公司製) 24.9g、作為觸媒之甲烷磺酸24.6g及作為自由基捕獲劑之對苯二酚1.41g後,以140℃使其反應23小時,而得到包含反應生成物之溶液。使用甲醇(3,600g)使其再沉澱。過濾所得之沉澱物,以減壓乾燥機60℃、乾燥24小時,而得到作為目的之聚合物。在PGMEA對20質量%溶液調整後,加入陰離子交換樹脂(製品名:DOWEX[註冊商標] MONOSPHERE[註冊商標]550A、MUROMACHI TECHNOS股份有限公司)100.00g與陽離子交換樹脂(製品名:Amberlite[註冊商標]15JWET、奧加諾股份有限公司) 100.00g,於25℃至30℃攪拌4小時後進行過濾。
進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為1,200。所得之反應生成物推定為具有下述式(7)表示之構造單位的共聚物。
<比較合成例1>
於PGME7.57g加入PGMEA17.67g、商品名:EHPE-3150(股份有限公司大賽璐製)5.00g、9-蒽羧酸3.11g、苯甲酸2.09g、乙基三苯基溴化鏻0.62g,氮環境下加熱回流13小時。於所得之溶液加入陽離子交換樹脂(製品名:Amberlite [註冊商標]15JWET、奧加諾股份有限公司)16g、陰離子交換樹脂(製品名:DOWEX[註冊商標] MONOSPHERE[註冊商標]550A、MUROMACHI TECHNOS股份有限公司)16g,於25℃至30℃攪拌4小時後進行過濾。
所得之進行反應生成物之GPC分析時,以標準聚苯乙烯換算,重量平均分子量為4,700。所得之反應生成物推定為具有下述式(8)表示之構造單位的共聚物。
[阻劑下層膜形成組成物的調製]
<實施例1>
於前述合成例1所得之共聚物0.80g,混合PGME6.36g、PGMEA2.76g及界面活性劑(DIC股份有限公司製、商品名:R-30N)1質量%PGME溶液0.080g,作為8.0質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
<實施例2>
於前述合成例2所得之共聚物0.80g,混合PGME6.36g、PGMEA2.76g及界面活性劑(DIC股份有限公司製、商品名:R-30N)1質量%PGME溶液0.080g,作為8.0質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
<實施例3>
於包含前述合成例3所得之共聚物0.55g之溶液(溶劑係使用在合成時之PGME、固體成分為20.54質量%)2.86g,混合四甲氧基甲基甘脲(製品名:POWDERLINK[註冊商標]1174、日本Cytec Industries 股份有限公司製)0.15g、吡啶鎓酚磺酸(Midori化學股份有限公司製)1質量%PGME溶液1.47g、PGME2.69g、PGMEA2.78g及界面活性劑(DIC股份有限公司製、商品名:R-30N)1質量%PGME溶液0.059g,作為7.5質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
<實施例4>
於前述合成例4所得之共聚物0.55g,混合四甲氧基甲基甘脲(製品名:POWDERLINK[註冊商標]1174、日本Cytec Industries 股份有限公司製)0.14g、吡啶鎓酚磺酸(Midori化學股份有限公司製)1質量%PGME溶液1.37g、PGME5.10g、PGMEA2.79g及界面活性劑(DIC股份有限公司製、商品名:R-30N)1質量%PGME溶液0.055g,作為7.0質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
<實施例5>
於包含前述合成例5所得之共聚物1.88g之溶液(溶劑為PGMEA、固體成分為17.08質量%)11.01g,混合商品名TMOM-BP(下述式之化合物、本州化學工業股份有限公司製)0.47g、吡啶鎓酚磺酸(Midori化學股份有限公司製)1質量%PGME溶液4.70g、PGME10.19g、PGMEA3.44g及界面活性劑(DIC股份有限公司製、商品名:R-30N)1質量%PGME溶液0.19g,作為8.0質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
<實施例6>
於包含前述合成例6所得之共聚物1.88g之溶液(溶劑為PGMEA、固體成分為16.27質量%)11.56g,混合商品名TMOM-BP(本州化學工業股份有限公司製)0.47g、吡啶鎓酚磺酸(Midori化學股份有限公司製)1質量%PGME溶液4.70g、PGME9.64g、PGMEA3.44g及界面活性劑(DIC股份有限公司製、商品名:R-30N)1質量%PGME溶液0.19g,作為8.0質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
<實施例7>
於包含前述合成例7所得之共聚物1.96g之溶液(溶劑為PGMEA、固體成分為19.60質量%)10.028g,混合商品名TMOM-BP(本州化學工業股份有限公司製)0.39g、TAG2689(King公司製、熱酸產生劑)2質量%PGME溶液1.96g、PGME6.35g、PGMEA11.06g及界面活性劑(DIC股份有限公司製、商品名:R-30N)1質量%PGMEA溶液0.19g,作為8.0質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
<比較例1>
於包含前述比較合成例1所得之共聚物4.51g之溶液(溶劑使用在合成時之PGME/PGMEA混合溶劑、固體成分為23.26質量%)19.52g,混合四甲氧基甲基甘脲(製品名:POWDERLINK[註冊商標]1174、日本Cytec Industries股份有限公司製)1.14g、吡啶鎓p-甲苯磺酸酯1質量%PGME溶液3.41g、PGME50.68g、PGMEA14.80g及界面活性劑(DIC股份有限公司製、商品名:R-30)1質量%PGME溶液0.45g,作為6.35質量%溶液。將該溶液使用孔徑0.2μm之聚四氟乙烯製微過濾器進行過濾,調製阻劑下層膜形成組成物。
[對光阻劑溶劑之溶出試驗]
分別將於實施例1至實施例7及比較例1所調製之阻劑下層膜形成組成物,藉由旋轉器塗佈在矽晶圓上。然後,於熱板上以下述表1所示之溫度焙烤1分鐘,形成阻劑下層膜(膜厚0.2μm)。將此等之阻劑下層膜浸漬在光阻劑溶液所使用之溶劑即PGME/PGMEA混合溶媒(質量混合比70/30),確認為不溶於溶劑,並將其結果於下述表1以“○”表示。
[光學參數之試驗]
分別將於實施例1至實施例7及比較例1所調製之阻劑下層膜形成組成物,藉由旋轉器塗佈在矽晶圓上。然後,於熱板上以下述表1所示之溫度焙烤1分鐘,形成阻劑下層膜(膜厚0.2μm)。使用光橢偏儀(J.A.Woollam公司製、VUV-VASE VU-302),測定此等之阻劑下層膜於波長193nm之折射率(n值)及阻尼係數(k值)。將其結果示於下述表1。上述阻劑下層膜由於具有充分之抗反射機能,故於波長193nm之k值期望為0.1以上。
[乾蝕刻速度的測定]
使用於實施例1及至實施例7及比較例1所調製之阻劑下層膜形成組成物,藉由與上述同樣之方法,於矽晶圓上形成阻劑下層膜。而且,將此等之阻劑下層膜的乾蝕刻速度使用Samco股份有限公司製RIE系統,以使用CF4
作為乾蝕刻氣體的條件下測定。算出將前述比較例1之乾蝕刻速度定為1.00時之前述各阻劑下層膜的乾蝕刻速度。將其結果於下述表1作為“相對乾蝕刻速度”表示。使用於實施例1及至實施例7所調製之阻劑下層膜形成組成物所形成之阻劑下層膜的乾蝕刻速度,與前述比較例1之乾蝕刻速度相比較,由於具有非常緩慢之乾蝕刻速度,故將本阻劑下層膜形成組成物作為遮罩,顯示基板加工容易。
[嵌入性評估]
在200nm膜厚之SiO2
基板、溝槽寬度50nm、節距100nm之密集圖型區域確認嵌入性。將於實施例1及至實施例6及比較例1所調製之阻劑下層膜形成組成物塗佈在上述基板上後,以250℃燒成60秒,形成約200nm之阻劑下層膜。將此基板的平坦化性使用日立High-Technologies股份有限公司製掃描電子顯微鏡(S-4800)進行觀察,確認對圖型內部之阻劑下層膜形成組成物之填充的有無時,確認實施例1及至實施例6雖為良好,但比較例1有空隙(void)。
[對段差基板之被覆試驗]
作為段差被覆性之評估,以200nm膜厚之SiO2
基板,進行溝槽寬度50nm、節距100nm之密集圖型區域(DENSE)與未形成圖型之開放區域(OPEN)之被覆膜厚的比較。將實施例5及比較例1之阻劑下層膜形成組成物於上述基板上以150nm的膜厚塗佈後,並以指定的溫度燒成。將此基板之段差被覆性使用日立High-Technologies(股)製掃描電子顯微鏡(S-4800)進行觀察,藉由測定段差基板之密集區域(圖型部)與開放區域(未圖型部)的膜厚差(有密集區域與開放區域的塗佈段差,稱為Bias),評估平坦化性。將於各區域之膜厚與塗佈段差之值示於表2。平坦化性評估係Bias之值越小平坦化性越高。
根據本發明,提供一種顯示高蝕刻耐性、良好之乾蝕刻速度比及光學定數,即使對於所謂的段差基板,被覆性亦良好,且嵌入後之膜厚差小,可形成平坦之膜的阻劑下層膜形成組成物、適合在該阻劑下層膜形成組成物之聚合物、使用該阻劑下層膜形成組成物之阻劑下層膜、以及半導體裝置之製造方法。
Claims (12)
- 如請求項1之阻劑下層膜形成組成物,其中,前述式(B)中之X及Y為氧原子或氮原子。
- 如請求項1之阻劑下層膜形成組成物,其中,前述芳香族化合物(A)包含1個以上之苯環、萘環、蒽環、芘環或該等之組合。
- 如請求項1之阻劑下層膜形成組成物,其中,前述芳香族化合物(A)包含2個以上之苯環、萘環、蒽環、芘環或該等之組合。
- 如請求項1~5中任一項之阻劑下層膜形成組成物,其係進一步包含交聯劑。
- 如請求項1~6中任一項之阻劑下層膜形成組成物,其係進一步包含酸及/或酸產生劑。
- 如請求項1之阻劑下層膜形成組成物,其中,前述溶劑的沸點為160℃以上。
- 一種阻劑下層膜,其特徵為包含如請求項1~8中任一項所記載之阻劑下層膜形成組成物而成之塗佈膜的燒成物。
- 一種半導體裝置之製造方法,其係包含:於半導體基板上使用如請求項1~8中任一項所記載之阻劑下層膜形成組成物,形成阻劑下層膜之步驟、 於所形成之阻劑下層膜之上形成阻劑膜之步驟、 藉由對於所形成之阻劑膜之光或電子束的照射與顯影,形成阻劑圖型之步驟、 透過所形成之阻劑圖型,蝕刻前述阻劑下層膜,而圖型化之步驟及 透過經圖型化之阻劑下層膜,加工半導體基板之步驟。
- 如請求項11之共聚物,其中,前述芳香族化合物(A)包含1個以上之苯環、萘環、蒽環、芘環或該等之組合。
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