JP6588996B2 - レジスト下層膜用組成物およびこれを用いたパターン形成方法 - Google Patents
レジスト下層膜用組成物およびこれを用いたパターン形成方法 Download PDFInfo
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- JP6588996B2 JP6588996B2 JP2018003350A JP2018003350A JP6588996B2 JP 6588996 B2 JP6588996 B2 JP 6588996B2 JP 2018003350 A JP2018003350 A JP 2018003350A JP 2018003350 A JP2018003350 A JP 2018003350A JP 6588996 B2 JP6588996 B2 JP 6588996B2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
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- 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
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- 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
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
-
- G—PHYSICS
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- 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
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4238—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof heterocyclic
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
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- 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
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- 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
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- G—PHYSICS
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- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- 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
-
- 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
- G03F7/092—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by backside coating or layers, by lubricating-slip layers or means, by oxygen barrier layers or by stripping-release layers or means
-
- 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
- G03F7/094—Multilayer resist systems, e.g. planarising layers
-
- 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
- G03F7/115—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having supports or layers with means for obtaining a screen effect or for obtaining better contact in vacuum printing
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/34—Imagewise removal by selective transfer, e.g. peeling away
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
-
- 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
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
-
- 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
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3083—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane
- H01L21/3088—Process specially adapted to improve the resolution of the mask
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- Manufacturing & Machinery (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Bは、下記化学式Zで表される2価の基、酸素原子、置換もしくは非置換の炭素数1〜30のアルキレン基、置換もしくは非置換の炭素数1〜30のヘテロアルキレン基、置換もしくは非置換の炭素数3〜30のシクロアルキレン基、またはこれらの組み合わせであり、
YおよびY’は、それぞれ独立して、単結合、酸素原子、カルボニル基、−(CH2)O−、−(CH2)S−、−(CH2)NH−、またはこれらの組み合わせであり、
R2〜R9は、それぞれ独立して、水素原子、ヒドロキシ基、ハロゲン原子、置換もしくは非置換のビニル基、置換もしくは非置換の炭素数1〜10のアルコキシ基、置換もしくは非置換の炭素数1〜30のアルキル基、置換もしくは非置換の炭素数2〜30のアルケニル基、置換もしくは非置換の炭素数2〜30のアルキニル基、置換もしくは非置換の炭素数6〜30のアリール基、置換もしくは非置換の炭素数1〜30のヘテロアルキル基、置換もしくは非置換の炭素数2〜30のヘテロアリール基、またはこれらの組み合わせであり、
a、b、c、dは、それぞれ独立して、0〜100の整数であり、この際、aおよびbの合計は1以上であり、cおよびdの合計は1以上であり、
*は、連結部である。
Aは、置換もしくは非置換の芳香族環基、置換もしくは非置換の脂環式基、置換もしくは非置換のヘテロ芳香族環基、置換もしくは非置換のヘテロ脂環式基、またはこれらの組み合わせであり、
Xは、水素原子、ヒドロキシ基、置換もしくは非置換の炭素数1〜10のアルコキシ基、ハロゲン原子、置換もしくは非置換の炭素数1〜30のアルキル基、置換もしくは非置換の炭素数2〜30のアルケニル基、置換もしくは非置換の炭素数2〜30のアルキニル基、置換もしくは非置換の炭素数6〜30のアリール基、置換もしくは非置換の炭素数2〜30のヘテロアリール基、置換もしくは非置換のビニル基、またはこれらの組み合わせであり、
*は、連結部である。
Bは、下記化学式Zで表される2価の基、酸素原子、置換もしくは非置換の炭素数1〜30のアルキレン基、置換もしくは非置換の炭素数1〜30のヘテロアルキレン基、置換もしくは非置換の炭素数3〜30のシクロアルキレン基、またはこれらの組み合わせであり、
YおよびY’は、それぞれ独立して、単結合、酸素原子、カルボニル基、−(CH2)O−、−(CH2)S−、−(CH2)NH−、またはこれらの組み合わせであり、
R2〜R9は、それぞれ独立して、水素原子、ヒドロキシ基、ハロゲン原子、置換もしくは非置換のビニル基、置換もしくは非置換の炭素数1〜10のアルコキシ基、置換もしくは非置換の炭素数1〜30のアルキル基、置換もしくは非置換の炭素数2〜30のアルケニル基、置換もしくは非置換の炭素数2〜30のアルキニル基、置換もしくは非置換の炭素数6〜30のアリール基、置換もしくは非置換の炭素数1〜30のヘテロアルキル基、置換もしくは非置換の炭素数2〜30のヘテロアリール基、またはこれらの組み合わせであり、
a、b、c、dは、それぞれ独立して、0〜100の整数であり、この際、aおよびbの合計は1以上であり、cおよびdの合計は1以上であり、
*は、連結部である、
Aは、置換もしくは非置換の芳香族環基、置換もしくは非置換の脂環式基、置換もしくは非置換のヘテロ芳香族環基、置換もしくは非置換のヘテロ脂環式基、またはこれらの組み合わせであり、
Xは、水素原子、ヒドロキシ基、置換もしくは非置換の炭素数1〜10のアルコキシ基、ハロゲン原子、置換もしくは非置換の炭素数1〜30のアルキル基、置換もしくは非置換の炭素数2〜30のアルケニル基、置換もしくは非置換の炭素数2〜30のアルキニル基、置換もしくは非置換の炭素数6〜30のアリール基、置換もしくは非置換の炭素数2〜30のヘテロアリール基、置換もしくは非置換のビニル基、またはこれらの組み合わせであり、
*は、連結部である、
mおよびnは、それぞれ独立して、1〜10の整数であり、
*は、連結部である。
(合成例1)
500mlの二口丸型フラスコに、1,3−ジアリル−5−(2−ヒドロキシエチル)イソシアヌレート[1,3−Diallyl−5−(2−hydroxyethyl) isocyanurate](30g)、1,2−エタンジチオール(1,2−Ethane dithiol)(11.16g)、アゾビスイソブチロニトリル(AIBN)(0.389g)、およびジメチルホルムアミド(DMF)(166g)を投入してコンデンサを連結した。温度を80℃に上げ、2.5時間反応させた後、当該反応液を常温(25℃)に冷却した。その後、前記反応液を1Lの広口瓶に移した後、ヘキサンで3回洗浄し、次に、ジエチルエーテルおよび精製水を用いて順次に洗浄した。得られたガム(gum)状態のレジンを、テトラヒドロフラン(THF)80gを用いて完全に溶解した後、攪拌中である700gのトルエン中に滴下した。溶媒を取り除いた後、真空ポンプを利用して残っている溶媒をさらに除去することにより、最終的に下記化学式1−1で表される構造単位を含む重合体(Mw=5,100)を得た。
500mlの二口丸型フラスコに、トリアリルシアヌレート(Triallylcyanurate)(14.96g)、1,2−エタンジチオール(1,2−Ethane dithiol)(3.81g)、AIBN(0.2g)、およびジメチルホルムアミド(25g)を投入してコンデンサを連結した。温度を80℃に上げ、2.5時間反応させた後、当該反応液を常温(25℃)に冷却した。その後、反応液を1L広口瓶に移した後、精製水およびトルエンを利用して順次に洗浄した。得られたガム(gum)状態のレジンを、THF80gを用いて完全に溶解させた後、攪拌中である700gのヘキサン中に徐々に滴下した。溶媒を取り除いた後、真空ポンプを利用して残っている溶媒をさらに除去することにより、最終的に下記化学式1−2で表される構造単位を含む重合体(Mw=17,000)を得た。
(合成例3)
500mlの二口丸型フラスコに、ジアリルエーテル(diallyl ether)(32.1g)、ジチオトレイトール(Dithiothreitol)(20.7g)、AIBN(0.5g)、およびDMF(210g)を投入したこと以外は、上記合成例2と同様の方法で実施して、下記化学式1−3で表される構造単位を含む重合体(Mw=2,700)を得た。
500mlの二口丸型フラスコに、1,6−ヘキサンジオールジアクリレート(1,6−hexanediol diacrylate)(32.1g)、ジチオトレイトール(Dithiothreitol)(20.7g)、AIBN(0.5g)、およびDMF(210g)を投入したこと以外は、上記合成例2と同様の方法で実施して、下記化学式1−4で表される構造単位を含む重合体(Mw=8,400)を得た。
500mlの二口丸型フラスコに、トリエチレングリコールジビニルエーテル(triethylene glycol divinyl ether)(30.4g)、ジチオトレイトール(Dithiothreitol)(20.7g)、AIBN(0.5g)、およびDMF(206g)を投入したこと以外は、上記合成例2と同様の方法で実施して、下記化学式1−5で表される構造単位を含む重合体(Mw=2,900)を得た。
500mlの二口丸型フラスコに、1,4−シクロヘキサンジメタノールジビニルエーテル(1,4−Cyclohexanedimethanol divinyl ether)(29.4g)、ジチオトレイトール(dithiothreitol)(20.7g)、AIBN(0.5g)、およびDMF(206g)を投入したこと以外は、上記合成例2と同様の方法で実施して、下記化学式1−6で表される構造単位を含む重合体(Mw=3,200)を得た。
500mlの二口丸型フラスコに、ジ(エチレングリコール)ジビニルエーテル[Di(ethylene glycol) divinyl ether](23.7g)、ジチオトレイトール(Dithiothreitol)(20.7g)、AIBN(0.5g)、およびDMF(206g)を投入したこと以外は、上記合成例2と同様の方法で実施して、下記化学式1−7で表される構造単位を含む重合体(Mw=4,500)を得た。
500mlの二口丸型フラスコに、テレフタル酸ジアリル(Diallyl terephthalate)(23.7g)、ジチオトレイトール(Dithiothreitol)(20.4g)、AIBN(0.5g)、およびDMF(206g)を投入したこと以外は、上記合成例2と同様の方法で実施して、下記化学式1−8で表される構造単位を含む重合体(Mw=4,200)を得た。
500mlの二口丸型フラスコに、メチルメタクリレート(Methyl methacrylate)(40g)、2−ヒドロキシエチルアクリレート(2−hydroxyethylacrylate)(52.1g)、ベンジルアクリレート(Benzyl acrylate)(70.4g)、AIBN(2g)、およびジオキサン(Dioxane)(306g)を投入してコンデンサを連結した。温度を80℃に上げ、2.5時間反応後、当該反応液を常温(25℃)に冷却した。反応液を3L広口瓶に移した後、ヘキサンで洗浄した。得られたレジンを30℃真空オーブンで乾燥させて残余の溶媒を除去することによって、最終的に下記化学式5で表される構造単位を含む重合体(Mw=12,000)を得た。
(実施例1)
合成例1で製造された重合体、PD1174(TCI社製;硬化剤)(重合体100質量部に対して15質量部)、およびピリジニウムp−トルエンスルホン酸(Pyridinium p−toluenesulfonate)(重合体100質量部に対して1質量部)を、プロピレングリコールモノメチルエーテルおよび乳酸エチルの混合溶媒(混合質量比=1:1)に溶かした後、6時間攪拌してレジスト下層膜用組成物を製造した。
合成例2〜8で製造された重合体をそれぞれ用いたこと以外は、実施例1と同様にして、レジスト下層膜用組成物を製造した。
比較合成例1で製造された重合体を用いたこと以外は、実施例1と同様にして、レジスト下層膜用組成物を製造した。
実施例1〜8および比較例1で製造された組成物を、それぞれ2mlずつ取って4インチウェハーの上にそれぞれ塗布した後、スピンコーター(Mikasa社製)を用いて、1,500rpmで20秒間スピンコーティングを行った。この後、210℃で90秒間硬化を実施して、30nm厚さの薄膜を形成した。それぞれの薄膜に対して、VASE Ellipsometer(J.A.Woollam社製)を用いて、電流を300Aにした条件で、各薄膜の屈折率(n)および吸光係数(k)を測定した。
102 薄膜、
104 レジスト下層膜、
106 フォトレジスト膜、
108 フォトレジストパターン、
110 マスク、
112 有機膜パターン、
114 薄膜パターン。
Claims (10)
- 下記化学式1および化学式2で表される部分構造を有する重合体と、
溶媒と、
を含む、レジスト下層膜用組成物:
Bは、下記化学式Zで表される2価の基、酸素原子、置換もしくは非置換の炭素数1〜30のアルキレン基、置換もしくは非置換の炭素数1〜30のヘテロアルキレン基、置換もしくは非置換の炭素数3〜30のシクロアルキレン基、またはこれらの組み合わせであり、
YおよびY’は、それぞれ独立して、単結合、酸素原子、カルボニル基、−(CH2)O−、−(CH2)S−、−(CH2)NH−またはこれらの組み合わせであり、
R 2 〜R 9 は、それぞれ独立して、水素原子、ハロゲン原子、置換もしくは非置換のビニル基、置換もしくは非置換の炭素数1〜10のアルコキシ基、置換もしくは非置換の炭素数1〜30のアルキル基、置換もしくは非置換の炭素数2〜30のアルケニル基、置換もしくは非置換の炭素数2〜30のアルキニル基、置換もしくは非置換の炭素数6〜30のアリール基、置換もしくは非置換の炭素数1〜30のヘテロアルキル基、置換もしくは非置換の炭素数2〜30のヘテロアリール基、またはこれらの組み合わせであり、
a、b、c、dは、それぞれ独立して、0〜100の整数であり、この際、aおよびbの合計は1以上であり、cおよびdの合計は1以上であり、
*は、連結部である、
Aは、置換もしくは非置換の芳香族環基、置換もしくは非置換の脂環式基、置換もしくは非置換のヘテロ芳香族環基、置換もしくは非置換のヘテロ脂環式基、またはこれらの組み合わせであり、
Xは、水素原子、ヒドロキシ基、置換もしくは非置換の炭素数1〜10のアルコキシ基、ハロゲン原子、置換もしくは非置換の炭素数1〜30のアルキル基、置換もしくは非置換の炭素数2〜30のアルケニル基、置換もしくは非置換の炭素数2〜30のアルキニル基、置換もしくは非置換の炭素数6〜30のアリール基、置換もしくは非置換の炭素数2〜30のヘテロアリール基、置換もしくは非置換のビニル基、またはこれらの組み合わせであり、
*は、連結部である、
- 前記化学式Z中のXが、置換もしくは非置換の炭素数1〜10のアルキル基、置換もしくは非置換の炭素数2〜30のアルケニル基、または置換もしくは非置換の炭素数2〜30のアルキニル基である、請求項1に記載のレジスト下層膜用組成物。
- 前記化学式Z中のAが、少なくとも1つのヘテロ原子を含有する芳香族環基または脂環式基である、請求項1または2に記載のレジスト下層膜用組成物。
- 前記化学式Z中のXは、前記化学式Z中のAに含まれるヘテロ原子に連結されている、請求項3に記載のレジスト下層膜用組成物。
- 前記重合体の重量平均分子量が1,000〜100,000である、請求項1〜4のいずれか1項に記載のレジスト下層膜用組成物。
- 前記レジスト下層膜用組成物は、架橋点を2つ以上有する架橋剤をさらに含む、請求項1〜5のいずれか1項に記載のレジスト下層膜用組成物。
- 前記レジスト下層膜用組成物は、界面活性剤、熱酸発生剤、および可塑剤からなる群より選択される少なくとも1種の添加剤をさらに含む、請求項1〜6のいずれか1項に記載のレジスト下層膜用組成物。
- 基板上にエッチング対象膜を形成する工程と、
前記エッチング対象膜上に請求項1〜7のいずれか1項に記載のレジスト下層膜用組成物を塗布してレジスト下層膜を形成する工程と、
前記レジスト下層膜上にフォトレジストパターンを形成する工程と、
前記フォトレジストパターンをエッチングマスクとして用いて、前記レジスト下層膜および前記エッチング対象膜を順次にエッチングする段階と、
を含む、パターン形成方法。 - 前記フォトレジストパターンを形成する工程は、
前記レジスト下層膜上にフォトレジスト膜を形成する工程と、
前記フォトレジスト膜を露光する工程と、
前記フォトレジスト膜を現像する工程と、
を含む、請求項8に記載のパターン形成方法。 - 前記レジスト下層膜を形成する工程は、前記レジスト下層膜用組成物の塗布後に100〜500℃の温度で熱処理する工程をさらに含む、請求項8または9に記載のパターン形成方法。
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