WO2019044874A1 - 感光性樹脂組成物 - Google Patents
感光性樹脂組成物 Download PDFInfo
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- WO2019044874A1 WO2019044874A1 PCT/JP2018/031879 JP2018031879W WO2019044874A1 WO 2019044874 A1 WO2019044874 A1 WO 2019044874A1 JP 2018031879 W JP2018031879 W JP 2018031879W WO 2019044874 A1 WO2019044874 A1 WO 2019044874A1
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- Prior art keywords
- photosensitive resin
- group
- resin composition
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- carbon atoms
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- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0387—Polyamides or polyimides
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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
- G03F7/038—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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/124—Unsaturated polyimide precursors the unsaturated precursors containing oxygen in the form of ether bonds in the main chain
-
- 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
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
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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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
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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
- G03F7/20—Exposure; Apparatus therefor
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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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
- G03F7/2006—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light using coherent light; using polarised light
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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
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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
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/325—Non-aqueous compositions
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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
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
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- 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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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/34—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies not provided for in groups H01L21/0405, H01L21/0445, H01L21/06, H01L21/16 and H01L21/18 with or without impurities, e.g. doping materials
- H01L21/46—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/428
- H01L21/461—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/428 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/469—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/428 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After-treatment of these layers
- H01L21/47—Organic layers, e.g. photoresist
Definitions
- the present invention relates to a negative photosensitive resin composition and a semiconductor device having a cured relief pattern obtained by curing the composition.
- polyimide resins having excellent heat resistance, electrical properties and mechanical properties have been used for insulating materials of electronic parts, passivation films of semiconductor devices, surface protective films, interlayer insulating films and the like.
- those provided in the form of a photosensitive polyimide precursor easily form a heat-resistant relief pattern film by thermal imidization treatment by coating, exposing, developing and curing the precursor. be able to.
- Such a photosensitive polyimide precursor has a feature of enabling significant process reduction as compared to a conventional non-photosensitive polyimide resin.
- the mounting method of a semiconductor device on a printed wiring board has also changed from the viewpoint of improving the degree of integration and computing functions, and reducing the chip size.
- the polyimide coating directly contacts the solder bumps, such as BGA (ball grid array), CSP (chip size packaging), etc., which enables higher density mounting than conventional metal pin and lead-tin eutectic solder mounting methods. Structure is coming into use. When forming such a bump structure, the film is required to have high heat resistance and chemical resistance.
- Patent Document 1 discloses a photosensitive material containing a polyimide precursor by introducing an aliphatic group having a carbon number of 5 to 30 having an ethylene glycol structure into a part of the side chain in the polyimide precursor. Disclosed is a photosensitive resin composition in which the transparency when forming the conductive resin composition is improved, and the Young's modulus of the cured film is further improved after thermosetting.
- the photosensitive resin composition comprising the polyimide precursor described in Patent Document 1 is highly transparent and gives a cured product having a high Young's modulus after heat curing, when used for the above-mentioned application Further reduction of the dielectric constant and the dielectric loss tangent has been desired.
- the present invention provides a photosensitive resin composition which gives a cured product of which dielectric constant and dielectric loss tangent are further reduced as a resin composition, a method of producing a cured relief pattern using the photosensitive resin composition, and the photosensitive resin composition.
- An object is to provide a semiconductor device provided with a cured relief pattern.
- the present inventors introduced a photosensitive resin composition containing a polyimide precursor by introducing a specific chemical structure into a part of the side chain in the polyimide precursor. It has been found that a photosensitive resin composition which gives a low dielectric constant and a low dielectric loss tangent when it is formed is obtained, and the present invention has been completed.
- X 1 is a tetravalent organic group having 6 to 40 carbon atoms
- Y 1 is a divalent organic group having 6 to 40 carbon atoms
- R 1 and R 2 are each Independently, a hydrogen atom, or the following general formula (2) or (3):
- R 3 , R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, and m is an integer of 1 to 10.
- * is And the binding site to the carboxylic acid present in the polyamic acid main chain of the general formula (1).
- R 6 is a monovalent organic group selected from alkyl groups having 1 to 30 carbon atoms. * Is the same as above.
- a monovalent organic group represented by the above general formula (2) for all R 1 and R 2 and a monovalent organic group represented by the above general formula (3) The ratio of the total of the groups is 80 mol% or more, and the ratio of the monovalent organic group represented by the above general formula (3) to all of R 1 and R 2 is 1 mol% to 90 mol% is there.
- a negative photosensitive resin composition comprising: [2]
- the R 6 is represented by the following formula (4):
- Z 1 is hydrogen or an alkyl group having 1 to 14 carbon atoms
- Z 2 is an alkyl group having 1 to 14 carbon atoms
- Z 3 is an alkyl group having 1 to 14 carbon atoms
- the total number of carbon atoms of Z 1 , Z 2 and Z 3 is 4 or more.
- the crosslinkable compound (C) 0.1 to 30 parts by mass relative to 100 parts by mass of the (A) polyimide precursor, any one of [1] to [3]
- the negative photosensitive resin composition as described in 4.
- a negative photosensitive resin film which is a fired product of a coating film comprising the negative photosensitive resin composition according to any one of [1] to [4].
- [6] The following steps: (1) applying the negative photosensitive resin composition according to any one of [1] to [4] on a substrate to form a photosensitive resin layer on the substrate; (2) exposing the photosensitive resin layer; (3) developing the photosensitive resin layer after the exposure to form a relief pattern; (4) A method of producing a cured relief pattern comprising the step of heat-treating the relief pattern to form a cured relief pattern. [7] A cured relief pattern produced by the method according to [6]. [8] A semiconductor device comprising: a semiconductor element; and a cured film provided on an upper part or a lower part of the semiconductor element, wherein the cured film is a cured relief pattern according to [6].
- a photosensitive resin composition which gives a cured product having a low dielectric constant and a low dielectric loss tangent as a resin composition, a method for producing a cured relief pattern using the photosensitive resin composition, and the cured relief pattern Can be provided.
- the negative photosensitive resin composition of the present invention comprises (A) a polyimide precursor, (B) a radical type photoinitiator, optionally (C) a crosslinkable compound, and optionally other components. Each ingredient is explained in order below.
- the (A) polyimide precursor is a resin component contained in the negative photosensitive resin composition, and is a polyamide having a structure represented by the following general formula (1).
- X 1 is a tetravalent organic group having 6 to 40 carbon atoms
- Y 1 is a divalent organic group having 6 to 40 carbon atoms
- R 1 and R 2 are each Independently, a hydrogen atom, or the following general formula (2) or (3):
- R 3 , R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, and m is an integer of 1 to 10.
- * is And the binding site to the carboxylic acid present in the polyamic acid main chain of the general formula (1).
- R 6 is a monovalent group selected from alkyl groups having 1 to 30 carbon atoms. * Is the same as above.
- a monovalent organic group represented by the above general formula (2) for all R 1 and R 2 and a monovalent organic group represented by the above general formula (3) The total of the groups is 80 mol% or more, and the ratio of the monovalent organic group represented by the above general formula (3) to all of R 1 and R 2 is 1 mol% to 90 mol%.
- X 1 is not limited as long as it is a tetravalent organic group having 6 to 40 carbon atoms, but from the viewpoint of achieving both heat resistance and photosensitive properties, preferably —COOR 1
- the group and the group -COOR 2 and the group -CONH- are an aromatic group or an alicyclic aliphatic group in which each other is in the ortho position.
- the tetravalent organic group represented by X 1 is more preferably an aromatic ring-containing organic group having 6 to 40 carbon atoms.
- X 1 is a tetravalent organic group represented by the following formula (5) or the following formulas (5-1) to (5-7).
- the structure of X 1 may be one kind or a combination of two or more kinds.
- Y 1 is not limited as long as it is a divalent organic group having 6 to 40 carbon atoms, but may be substituted from the viewpoint of achieving both heat resistance and photosensitive characteristics.
- a cyclic organic group having 1 to 4 aromatic rings or aliphatic rings, or an aliphatic group having no cyclic structure or a siloxane group is preferable.
- Y 1 is a structure represented by the following general formula (6), the following general formula (7) or the following formula (8).
- A represents each independently a methyl group (-CH 3 ), an ethyl group (-C 2 H 5 ), a propyl group (-C 3 H 7 ) or a butyl group (-C 4 H 9 ) .
- the structure of Y 1 may be one kind or a combination of two or more kinds.
- R 1 and R 2 in the general formula (1) are each independently a hydrogen atom or a monovalent organic group represented by the general formula (2) or (3).
- Each of R 1 and R 2 may be one or a combination of two or more, but is preferably a combination of three or less, preferably a combination of two each, and most preferably one each.
- the ratio of the total of monovalent organic groups represented by (3) is 80 mol% or more, and the ratio of the monovalent organic groups represented by the above general formula (3) to all of R 1 and R 2
- the proportion is 1 mol% to 90 mol%, preferably 1 mol% to 80 mol%, preferably 1 mol% to 70 mol%, preferably 1 mol% to 60 mol%, Preferably, it is 1 mol% to 50 mol%, preferably 1 mol% to 40 mol%, preferably 1 mol% to 30 mol%, and preferably 1 mol% to 19 mol%.
- R 3 in the above general formula (2) is not limited as long as it is a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, but from the viewpoint of the photosensitive properties of the photosensitive resin composition, a hydrogen atom or methyl It is preferably a group.
- R 4 and R 5 in the above general formula (2) are not limited as long as they are each independently a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, but the photosensitive characteristics of the photosensitive resin composition It is preferable that it is a hydrogen atom from a viewpoint.
- M in the above general formula (2) is an integer of 1 or more and 10 or less, and preferably 2 or more and 4 or less from the viewpoint of the photosensitive properties.
- R 6 in the general formula (3) is not limited as long as it is a monovalent organic group selected from alkyl groups having 1 to 30 carbon atoms. It may have a branched structure or a cyclic structure as well as a linear structure.
- R 6 in the above general formula (3) is preferably an alkyl group having 5 to 30 carbon atoms, preferably an alkyl group having 8 to 30 carbon atoms, and preferably an alkyl group having 9 to 30 carbon atoms, An alkyl group having 10 to 30 carbon atoms is preferable, an alkyl group having 11 to 30 carbon atoms is more preferable, and an alkyl group having 17 to 30 carbon atoms is further preferable.
- said R 6 is a group of the following formula (4):
- Z 1 is hydrogen or an alkyl group having 1 to 14 carbon atoms
- Z 2 is an alkyl group having 1 to 14 carbon atoms
- Z 3 is an alkyl group having 1 to 14 carbon atoms
- Z 1 , Z 2 and Z 3 may be mutually the same or different
- the total number of carbon atoms of Z 1 , Z 2 and Z 3 is 4 or more. It is preferable that it is represented by this.
- Z 1 is hydrogen.
- Z 1 , Z 2 and Z 3 are preferably an alkyl group having 2 to 12 carbon atoms, and more preferably an alkyl group having 2 to 10 carbon atoms.
- the total number of carbon atoms of Z 1 , Z 2 and Z 3 is preferably 5 or more, more preferably 6 or more, preferably 10 or more, and preferably 12 or more. Preferably 15 or more, and more preferably 16 or more.
- the total number of carbon atoms in Z 1 , Z 2 and Z 3 is preferably 6 or more and 20 or less.
- the upper limit of the total number of carbon atoms of Z 1 , Z 2 and Z 3 is preferably 28.
- R 6 may be selected from the following formulas (3-1) to (3-7).
- the R 6 is preferably selected from the above formulas (3-1) to (3-7).
- the polyimide precursor is converted to polyimide by heat cyclization treatment.
- the polyimide precursor represented by the above general formula (1) in the present embodiment is, for example, a tetracarboxylic acid dianhydride containing the above-mentioned tetravalent organic group X 1 having 6 to 40 carbon atoms, and (a) above Alcohols formed by bonding of a monovalent organic group represented by the general formula (2) and a hydroxyl group, and (b) bonding of a monovalent organic group represented by the above general formula (3) and a hydroxyl group
- the following alcohols are reacted to prepare a partially esterified tetracarboxylic acid (hereinafter also referred to as an acid / ester), followed by the above-mentioned divalent organic group having 6 to 40 carbon atoms Y 1 It is obtained by polycondensing with diamine containing.
- examples of the tetracarboxylic acid dianhydride containing a tetravalent organic group X 1 having 6 to 40 carbon atoms include pyromellitic anhydride, diphenyl ether-3, 3 ', 4, 4'-tetracarbon, and the like.
- Examples of alcohols having a structure represented by the above general formula (2) include 2-acryloyloxyethyl alcohol, 1-acryloyloxy-3-propyl alcohol, methylol vinyl ketone, 2 -Hydroxyethyl vinyl ketone, 2-hydroxy-3-methoxypropyl acrylate, 2-hydroxy-3-butoxypropyl acrylate, 2-hydroxy-3-butoxypropyl acrylate, 2-methacryloyloxyethyl alcohol, 1-methacryloyloxy-3- Propyl alcohol, 2-hydroxy-3-methoxypropyl methacrylate, 2-hydroxy-3-butoxypropyl methacrylate, 2-hydroxy-3-butoxypropyl methacrylate, 2-hydroxyethyl methacrylate Mention may be made of the rate, and the like.
- Examples of aliphatic alcohols having 1 to 30 carbon atoms represented by the general formula (3) include alcohols in which the hydrogen atom of the above alkyl having 1 to 30 carbon atoms is substituted with a hydroxy group Can be mentioned.
- Alcohols having the structures of the above formulas (3-1) to (3-6) may be used.
- the following commercial products may be used.
- the total content of the components (a) and (b) in the negative photosensitive resin composition is 80 mol% or more with respect to the total content of R 1 and R 2 in the general formula (1).
- the content of the component (b) is preferably 1 mol% to 90 mol% with respect to all the contents of R 1 and R 2 for the purpose of lowering the dielectric constant and the dielectric loss tangent.
- reaction solvent those capable of dissolving the acid / ester and a polyimide precursor which is a polycondensation product of the acid / ester and a diamine are preferable.
- a polyimide precursor that can be used in the embodiment by dropping and separately adding a solution in which a diamine containing a divalent organic group Y 1 having 6 to 40 carbon atoms is separately dissolved or dispersed in a solvent You can get
- diamines containing a divalent organic group Y 1 having 6 to 40 carbon atoms include p-phenylenediamine, m-phenylenediamine, 4,4-diaminodiphenyl ether, 3,4′-diaminodiphenyl ether, and 3,3 '-Diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-Diaminodiphenyl sulfone, 4,4'-diaminobiphenyl, 3,4'-diaminobiphenyl, 3,3'-diaminobiphenyl, 4,4'-diaminobenzophen
- the diamines used in the present application are not limited to these.
- (A) polyimide precursor in order to improve the adhesion between the photosensitive resin layer formed on the substrate and the various substrates by applying the negative photosensitive resin composition on the substrate, (A) polyimide precursor It is also possible to copolymerize diaminosiloxanes such as 1,3-bis (3-aminopropyl) tetramethyldisiloxane, 1,3-bis (3-aminopropyl) tetraphenyldisiloxane and the like during the preparation of
- the water absorption by-product of the dehydration condensation agent coexisting in the reaction liquid is separated by filtration if necessary, and then a poor solvent such as water, an aliphatic lower alcohol, or a mixture thereof is used.
- the polymer precursor is introduced into the reaction solution to precipitate the polymer component, and further, the polymer is purified by repeating the re-dissolution, re-precipitation and the like operations, and vacuum drying is performed, and a polyimide precursor which can be used in the embodiment. Isolate the body.
- the solution of this polymer may be passed through a column packed with an anion and / or cation exchange resin swollen with a suitable organic solvent to remove ionic impurities.
- the molecular weight of the polyimide precursor (A) is preferably 5,000 to 150,000, and preferably 7,000 to 50,000, as measured by gel permeation chromatography using polystyrene as the weight average molecular weight. Is more preferred.
- the weight average molecular weight is 5,000 or more, it is preferable because the mechanical properties are good.
- the dispersibility in the developer and the resolution performance of the relief pattern It is preferable because it is good.
- the negative photosensitive resin composition of the present invention contains a radical type photopolymerization initiator as the component (B).
- the photopolymerization initiator is not particularly limited as long as it is a compound having absorption in a light source used at the time of photocuring, and examples thereof include tert-butylperoxy-iso-butyrate, 2,5-dimethyl-2,5-bis (benzoyl) Dioxy) hexane, 1,4-bis [ ⁇ - (tert-butyldioxy) -iso-propoxy] benzene, di-tert-butylperoxide, 2,5-dimethyl-2,5-bis (tert-butyldioxy) hexene hydro Peroxide, ⁇ - (iso-propylphenyl) -iso-propyl hydroperoxide, tert-butyl hydroperoxide, 1,1-bis (tert-butyldioxy
- the above radical type photopolymerization initiators can be obtained as commercial products, and, for example, IRGACURE [registered trademark] 651, 184, 2959, 127, 907, 369, 379EG, 819, 819DW , 1800, 1870, 784, OXE01, OXE 02, 250, 1173, MBF, TPO, 4265, TPO (above, manufactured by BASF), KAYACURE [registered trademark] DETX, MBP , The same DMBI, the same EPA, the same OA (above, Nippon Kayaku Co., Ltd.), VICURE-10, the same 55 (above, STAUFFER Co.
- ESACURE KIP150 the same TZT, the same 1001, the same KTO46, KB1, KL200, KS300, EB3, triazine-PMS, triazine A, tri Jin B (or more, Japan Siber Hegner Co., Ltd.), ADEKAOPTOMER N-1717, the same N-1414, the same N-1606 (or more, Co., Ltd. ADEKA) are exemplified.
- These radical type photopolymerization initiators may be used alone or in combination of two or more.
- the blending amount of the (B) radical type photopolymerization initiator is 0.1 parts by mass to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor, and from 0.5 parts by mass from the viewpoint of photosensitivity characteristics 15 parts by mass is preferred.
- the negative photosensitive resin composition is excellent in photosensitivity by blending (B) a radical type photopolymerization initiator in an amount of 0.1 parts by mass or more based on 100 parts by mass of the (A) polyimide precursor, while 20 parts by mass By mix
- the negative photosensitive resin composition preferably further contains (C) a crosslinkable compound.
- the crosslinkable compound can crosslink the polyimide precursor (A) when photocuring the relief pattern formed using the negative photosensitive resin composition, or the crosslinkable compound itself can form a crosslinked network. It can be an agent.
- the crosslinkable compound (C) is preferable because it can further enhance the heat resistance and chemical resistance of the cured film formed from the negative photosensitive resin composition.
- g line, h line, i line, ghi line broadband, and a KrF excimer laser are mentioned, for example.
- the exposure dose is preferably 25 mJ / cm 2 to 1000 mJ / cm 2 .
- a monomer having a photopolymerizable unsaturated bond can be optionally blended into the negative photosensitive resin composition.
- a (meth) acrylic compound which undergoes a radical polymerization reaction by a photopolymerization initiator is preferable, and although not particularly limited thereto, ethylene glycol including diethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, etc.
- the compounding amount of the photopolymerizable unsaturated bond-containing monomer is preferably 1 part by mass to 50 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
- difunctional (meth) acrylates can be mentioned.
- the bifunctional (meth) acrylate is a compound having an acryloyl group or a methacryloyl group at both ends of the molecule.
- the compound include tricyclodecane dimethanol diacrylate, tricyclodecane dimethanol dimethacrylate, tricyclodecane diethanol diacrylate, and tricyclodecane diethanol dimethacrylate.
- the above difunctional (meth) acrylate is commercially available, and for example, A-DCP, DCP (all, Shin-Nakamura Chemical Co., Ltd. product), New Frontier (registered trademark) HBPE-4 (first Manufactured by Kogyo Seiyaku Co., Ltd.). These compounds may be used alone or in combination of two or more.
- the content of the crosslinkable compound (C) in the negative photosensitive resin composition of the present invention is 0.1 parts by mass of the crosslinkable compound (C) with respect to 100 parts by mass of the polyimide precursor (A). It will not be limited if it is 50 mass parts. Among them, 0.5 parts by mass to 30 parts by mass is preferable. When the compounding amount is 0.1 parts by mass or more, good heat resistance and chemical resistance develop, and when it is 50 parts by mass or less, storage stability is excellent, which is preferable.
- the content is, for example, the total content of two or more when used.
- the negative photosensitive resin composition may further contain components other than the components (A) to (C).
- the other components include solvents, resin components other than the (A) polyimide precursor, sensitizers, adhesion assistants, thermal polymerization inhibitors, azole compounds, hindered phenol compounds, fillers and the like.
- thermal crosslinking agent hexamethoxymethylmelamine, tetramethoxymethylglycoluril, tetramethoxymethylbenzoguanamine, 1,3,4,6-tetrakis (methoxymethyl) glycoluril, 1,3,4,6-tetrakis (butoxymethyl) ) Glycoluril, 1,3,4,6-tetrakis (hydroxymethyl) glycoluril, 1,3-bis (hydroxymethyl) urea, 1,1,3,3-tetrakis (butoxymethyl) urea and 1,1,1,3 Examples include 3,3-tetrakis (methoxymethyl) urea.
- the filler include inorganic fillers, and specific examples include sols such as silica, aluminum nitride, boron nitride, zirconia, and alumina.
- an organic solvent from the viewpoint of solubility in the (A) polyimide precursor.
- the solvent is, for example, in the range of 30 parts by mass to 1500 parts by mass, preferably 100 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor, depending on the desired coating thickness and viscosity of the negative photosensitive resin composition. It can be used in the range of parts by mass to 1000 parts by mass.
- the negative photosensitive resin composition may further contain a resin component other than the (A) polyimide precursor.
- resin components that can be contained in the negative photosensitive resin composition include polyimide, polyoxazole, polyoxazole precursor, phenol resin, polyamide, epoxy resin, siloxane resin, acrylic resin and the like.
- the compounding amount of these resin components is preferably in the range of 0.01 parts by mass to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
- a sensitizer can be optionally blended with the negative photosensitive resin composition in order to improve the photosensitivity.
- the sensitizer include Michler's ketone, 4,4′-bis (diethylamino) benzophenone, 2,5-bis (4′-diethylaminobenzal) cyclopentane, 2,6-bis (4′-diethylaminobenzal) ) Cyclohexanone, 2,6-bis (4'-diethylaminobenzal) -4-methylcyclohexanone, 4,4'-bis (dimethylamino) chalcone, 4,4'-bis (diethylamino) chalcone, p-dimethylaminocinnana Myrylene indanone, p-dimethylaminobenzylidene indanone, 2- (p-dimethylaminophenylbiphenylene) -benzothiazole, 2- (p-dimethylaminophenylvinylene) be
- the compounding amount of the sensitizer is preferably 0.1 parts by mass to 25 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
- an adhesion auxiliary may be optionally added to the negative photosensitive resin composition.
- the adhesion assistant for example, ⁇ -aminopropyldimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, 3-methacryloxypropyldimethoxymethylsilane, 3-methacryloxypropyltrimethoxysilane, dimethoxymethyl-3-piperidinopropylsilane, diethoxy-3-glycidoxypropylmethylsilane, N- (3-diethoxymethylsilylpropyl) ) Succinimide, N- [3- (triethoxysilyl) propyl]
- adhesion assistants it is more preferable to use a silane coupling agent from the viewpoint of adhesion.
- the blending amount of the adhesion assistant is preferably in the range of 0.5 parts by mass to 25 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
- a thermal polymerization inhibitor in order to improve the stability of the viscosity and the photosensitivity of the negative photosensitive resin composition during storage particularly in the state of a solution containing a solvent, a thermal polymerization inhibitor can be optionally blended.
- the thermal polymerization inhibitor include hydroquinone, N-nitrosodiphenylamine, p-tert-butylcatechol, phenothiazine, N-phenylnaphthylamine, ethylenediaminetetraacetic acid, 1,2-cyclohexanediaminetetraacetic acid, glycol ether diamine tetraacetic acid, 2 , 6-Di-tert-butyl-p-methylphenol, 5-nitroso-8-hydroxyquinoline, 1-nitroso-2-naphthol, 2-nitroso-1-naphthol, 2-nitroso-5- (N-ethyl- N-sulfopropylamino) phenol, N-nitroso-N-pheny
- the compounding amount of the thermal polymerization inhibitor is preferably in the range of 0.005 parts by mass to 12 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
- an azole compound in the case of using a substrate made of copper or a copper alloy, can be optionally blended in the negative photosensitive resin composition in order to suppress substrate discoloration.
- the azole compound include 1H-triazole, 5-methyl-1H-triazole, 5-ethyl-1H-triazole, 4,5-dimethyl-1H-triazole, 5-phenyl-1H-triazole, 4-t-butyl -5-phenyl-1H-triazole, 5-hydroxyphenyl-1H-triazole, phenyltriazole, p-ethoxyphenyltriazole, 5-phenyl-1- (2-dimethylaminoethyl) triazole, 5-benzyl-1H-triazole, Hydroxyphenyltriazole, 1,5-dimethyltriazole, 4,5-diethyl-1H-triazole, 1H-benzotriazole, 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- [2-hydroxy-3
- the compounding amount of the azole compound is preferably 0.1 parts by mass to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor, and from 0.5 parts by mass to 5 parts by mass from the viewpoint of photosensitivity characteristics It is more preferable that When the compounding quantity with respect to 100 mass parts of (A) polyimide precursors of an azole compound is 0.1 mass part or more, when a negative photosensitive resin composition is formed on copper or a copper alloy, copper or The discoloration of the surface of the copper alloy is suppressed, and when it is 20 parts by mass or less, it is preferable because of excellent photosensitivity.
- a hindered phenol compound can be optionally added to the negative photosensitive resin composition in order to suppress discoloration on copper.
- the hindered phenol compound for example, 2,6-di-t-butyl-4-methylphenol, 2,5-di-t-butyl-hydroquinone, octadecyl-3- (3,5-di-t-butyl) -4-hydroxyphenyl) propionate, isooctyl-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, 4,4'-methylenebis (2,6-di-t-butylphenol), 4,4'-thio-bis (3-methyl-6-t-butylphenol), 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), triethylene glycol-bis [3- (3) -T-Butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-
- 1,3,5-tris (4-t-butyl-3-hydroxy-2,6-dimethylbenzyl) -1,3,5-triazine-2,4,6- (1H, 3H, 5H) )-Triones are particularly preferred.
- the compounding amount of the hindered phenol compound is preferably 0.1 part by mass to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor, and 0.5 parts by mass to 10 parts by mass from the viewpoint of photosensitivity characteristics It is more preferable that it is a part.
- the compounding quantity with respect to 100 mass parts of (A) polyimide precursors of a hindered phenol compound is 0.1 mass part or more, for example, when a negative photosensitive resin composition is formed on copper or a copper alloy, copper Alternatively, discoloration or corrosion of the copper alloy can be prevented, and on the other hand, 20 parts by mass or less is preferable because of excellent photosensitivity.
- Step (1) to (4) (1) A step of applying the negative photosensitive resin composition of the embodiment onto a substrate to form a photosensitive resin layer on the substrate, (2) exposing the photosensitive resin layer, (3) developing a photosensitive resin layer after the exposure to form a relief pattern, and (4) heating the relief pattern to form a cured relief pattern.
- a manufacturing method can be provided.
- a step of applying the negative photosensitive resin composition of the embodiment on a substrate to form a photosensitive resin layer on the substrate the negative photosensitive resin composition of the embodiment is used. It apply
- a coating method a method conventionally used for coating a photosensitive resin composition, for example, a method of coating by a spin coater, a bar coater, a blade coater, a curtain coater, a screen printer, etc., spray coating by a spray coater A method etc. can be used.
- the coating film made of the negative photosensitive resin composition can be dried, and as a drying method, for example, methods such as air drying, heat drying with an oven or a hot plate, vacuum drying and the like are used. Moreover, it is desirable that drying of a coating film is performed on the conditions that imidation of (A) polyimide precursor in a negative photosensitive resin composition does not occur. Specifically, when air drying or heat drying is performed, drying can be performed at 20 ° C. to 200 ° C. for 1 minute to 1 hour. Thus, the photosensitive resin layer can be formed on the substrate.
- the photosensitive resin layer formed in the above step (1) is treated with an exposure apparatus such as a contact aligner, mirror projection, stepper or the like to form a photomask Alternatively, exposure is performed by an ultraviolet light source or the like through the reticle or directly.
- an exposure apparatus such as a contact aligner, mirror projection, stepper or the like to form a photomask Alternatively, exposure is performed by an ultraviolet light source or the like through the reticle or directly.
- post exposure bake (PEB) and / or post development bake may be performed according to any combination of temperature and time, as necessary, for the purpose of improving photosensitivity and the like.
- the range of baking conditions is preferably a temperature of 50 ° C. to 200 ° C., and a time of 10 seconds to 600 seconds, but unless it impairs various properties of the negative photosensitive resin composition, It is not limited to this range.
- (3) A step of developing the photosensitive resin layer after the exposure to form a relief pattern In this step, the unexposed part of the photosensitive resin layer after the exposure is removed by development.
- any of known methods for developing a photoresist for example, a rotary spray method, a paddle method, an immersion method accompanied by ultrasonic treatment and the like can be used. You can use it by selecting the method.
- post-development baking may be performed at any temperature and time combination, as necessary, for the purpose of adjusting the shape of the relief pattern and the like.
- Examples of the developer used for development include N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N, N-dimethylacetamide, cyclopentanone, cyclohexanone, ⁇ -butyrolactone, ⁇ -acetyl- ⁇ -Butyrolactone etc. are preferred. In addition, two or more types of each solvent, for example, several types may be used in combination. (4) A step of heating the relief pattern to form a cured relief pattern In this step, the relief pattern obtained by the above development is heated to dilute the photosensitive component and (A) a polyimide precursor is prepared. By imidization, it is converted to a cured relief pattern made of polyimide.
- various methods can be selected, such as using a hot plate, using an oven, using a temperature rising oven capable of setting a temperature program, and the like.
- the heating can be performed, for example, at 130 ° C. to 250 ° C. for 30 minutes to 5 hours.
- atmosphere gas at the time of heat curing air may be used, or an inert gas such as nitrogen or argon may be used.
- a semiconductor device which comprises the cured relief pattern obtained by the method for producing the cured relief pattern described above. Therefore, a semiconductor device can be provided which has a substrate which is a semiconductor element and a cured relief pattern of polyimide formed on the substrate by the above-described method of producing a cured relief pattern.
- the present invention can also be applied to a method of manufacturing a semiconductor device using a semiconductor element as a base material and including the method of manufacturing a cured relief pattern described above as part of the process.
- a semiconductor device is a semiconductor device having a surface protection film, an interlayer insulation film, an insulation film for rewiring, a protection film for flip chip devices, or a bump structure, which is formed by the above-mentioned method for producing a hardening relief pattern.
- the protective film of the present invention can be formed by combining with a known method of manufacturing a semiconductor device.
- the embodiment provides a display device comprising a display element and a cured film provided on the top of the display element, wherein the cured film is the above-mentioned cured relief pattern.
- the cured relief pattern may be laminated in direct contact with the display element, or may be laminated with another layer interposed therebetween.
- the cured film there can be mentioned surface protective film of TFT liquid crystal display element and color filter element, insulating film, flattening film, projection for MVA type liquid crystal display device, and partition wall for organic EL element cathode. .
- the negative photosensitive resin composition of the present invention is used in applications such as interlayer insulation of a multilayer circuit, a cover coat of a flexible copper clad plate, a solder resist film, a liquid crystal alignment film, etc. in addition to the application to the semiconductor device as described above. Is also useful.
- the present invention will next be described in detail by way of examples, which should not be construed as limiting the invention thereto.
- the weight average molecular weight shown to the following synthesis example of this specification is a measurement result by gel permeation chromatography (Hereafter, it abbreviates as GPC in this specification.).
- the measurement conditions etc. are as follows using GPC apparatus (HLC-8320GPC) made by Tosoh Corp. for measurement.
- the obtained crude polymer solution was dropped into 7.2 kg of water to precipitate a polymer, and the obtained precipitate was separated by filtration and then vacuum dried to obtain a fibrous polymer (2B).
- the molecular weight of the polymer 1B was measured by GPC (in terms of standard polystyrene), and the weight average molecular weight (Mw) was 24,181. The yield was 67.9%.
- This reaction product has a repeating unit structure represented by the following formula (2B).
- the obtained crude polymer solution was dropped into 7.2 kg of water to precipitate a polymer, and the obtained precipitate was separated by filtration and then vacuum dried to obtain a fibrous polymer (1B).
- the molecular weight of the polymer 1B was measured by GPC (in terms of standard polystyrene), and the weight average molecular weight (Mw) was 20,112. The yield was 50.8%.
- This reaction product has a repeating unit structure represented by the following formula (1B).
- the resulting reaction mixture was added to 450 g of ethanol (Kanto Chemical, special grade) to form a precipitate consisting of a crude polymer.
- the supernatant was decanted to separate the crude polymer, which was dissolved in 255 g of tetrahydrofuran to obtain a crude polymer solution.
- the obtained crude polymer solution was dropped into 5.4 kg of water to precipitate a polymer, and the obtained precipitate was separated by filtration and then vacuum dried to obtain a fibrous polymer (1C).
- the molecular weight of the polymer 1C was measured by GPC (in terms of standard polystyrene), the weight average molecular weight (Mw) was 29,327. The yield was 59.9%.
- This reaction product has a repeating unit structure represented by the following formula (1C).
- the resulting reaction mixture was added to 450 g of ethanol (Kanto Chemical, special grade) to form a precipitate consisting of a crude polymer.
- the precipitate was filtered and dissolved in 255 g of tetrahydrofuran (THF, Kanto Chemical, special grade) and 105 g of NMP to obtain a crude polymer solution.
- the obtained crude polymer solution is dropped into 5.4 kg of water to precipitate a polymer, and the obtained precipitate is separated by filtration and then washed twice with 150 g of methanol (Kanto Chemical, deer special grade) and vacuum dried. As a result, a fibrous polymer (3B) was obtained.
- the molecular weight of the polymer 3B was measured by GPC (in terms of standard polystyrene), and the weight average molecular weight (Mw) was 26,611. The yield was 68.9%.
- This reaction product has a repeating unit structure represented by the following formula (3B).
- the resulting reaction mixture was added to 450 g of ethanol (Kanto Chemical, special grade) to form a precipitate consisting of a crude polymer.
- the precipitate was filtered and dissolved in 360 g of tetrahydrofuran (THF, Kanto Chemical, special grade) and 150 g of NMP to obtain a crude polymer solution.
- the obtained crude polymer solution is dropped into 5.4 kg of water to precipitate a polymer, and the obtained precipitate is separated by filtration, washed twice with 300 g of methanol, and vacuum dried to obtain a polymer (4B) I got
- the molecular weight of the polymer 4B was measured by GPC (in terms of standard polystyrene), and the weight average molecular weight (Mw) was 26,583. The yield was 68.5%.
- This reaction product has a repeating unit structure represented by the following formula (4B).
- the obtained crude polymer solution was dropped into 650 kg of water to precipitate a polymer, and the obtained precipitate was separated by filtration and then vacuum dried to obtain a fibrous polymer (6B).
- the molecular weight of the polymer (6B) was measured by GPC (in terms of standard polystyrene), and the weight average molecular weight (Mw) was 14,102.
- This reaction product has a repeating unit structure represented by the following formula (6B).
- the obtained crude polymer solution was dropped into 650 kg of water to precipitate a polymer, and the obtained precipitate was separated by filtration and then vacuum dried to obtain a fibrous polymer (7B).
- the molecular weight of the polymer (7B) was measured by GPC (in terms of standard polystyrene), and the weight average molecular weight (Mw) was 12401.
- This reaction product has a repeating unit structure represented by the following formula (7B).
- Example 1 8.00 g of the polymer obtained in Production Example 1, 0.16 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 0.80 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 0.80 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 27.78 g of cyclohexanone.
- IRGACURE registered trademark
- OXE01 manufactured by BASF
- tricyclodecanedimethanol diacrylate manufactured by Shin-Nakamura Chemical Co., Ltd.
- a composition was prepared by dissolving 0.80 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 27.78 g of
- Example 2 11.40 g of the polymer obtained in Production Example 2, 0.23 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 1.14 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 1.14 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 28.23 g of cyclohexanone.
- IRGACURE registered trademark
- OXE01 manufactured by BASF
- OXE01 tricyclodecanedimethanol diacrylate
- a composition was prepared by dissolving 1.14 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 28.23 g of cyclohexanone.
- Example 3 11.00 g of the polymer obtained in Production Example 5, 0.22 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 1.10 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 1.10 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 24.92 g of cyclohexanone.
- IRGACURE registered trademark
- OXE01 manufactured by BASF
- HBPE-4 manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.
- Example 4 9.00 g of the polymer obtained in Production Example 6, 0.18 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 0.90 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 20.39 g of cyclohexanone.
- IRGACURE registered trademark
- OXE01 manufactured by BASF
- tricyclodecanedimethanol diacrylate manufactured by Shin-Nakamura Chemical Co., Ltd.
- a composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 20.39 g of
- Example 5 9.00 g of the polymer obtained in Production Example 7, 0.18 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 0.90 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 20.39 g of cyclohexanone.
- IRGACURE registered trademark
- OXE01 manufactured by BASF
- OXE01 tricyclodecanedimethanol diacrylate
- a composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 20.39 g of cyclohexanone.
- Comparative Example 1 9.00 g of the polymer obtained in Production Example 3, 0.18 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 0.90 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 19.52 g of N-methyl 2-pyrrolidone.
- Comparative Example 2 9.00 g of the polymer obtained in Production Example 4, 0.18 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 0.90 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 19.52 g of N-methyl 2-pyrrolidone.
- Reference Example 1 9.00 g of the polymer obtained in Production Example 8, 0.18 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 0.90 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 19.52 g of N-methyl 2-pyrrolidone.
- Reference Example 2 9.00 g of the polymer obtained in Production Example 9, 0.18 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF), 0.90 g of tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and A composition was prepared by dissolving 0.90 g of New Frontier (registered trademark) HBPE-4 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in 19.52 g of N-methyl 2-pyrrolidone. Then, it filtered using the polypropylene microfilter with a hole diameter of 5 micrometers, and prepared the negative photosensitive resin composition.
- IRGACURE registered trademark
- OXE01 manufactured by BASF
- tricyclodecanedimethanol diacrylate manufactured by Shin-Nakamura Chemical Co., Ltd.
- a composition was prepared by dissolving 0.90 g of New Frontier (registered trademark)
- the dielectric constant and the dielectric loss tangent at 1 GHz were calculated by the perturbation type cavity resonator method (apparatus: TMR-1A, manufactured by Keycom Co., Ltd.) using this free standing film. Details of the measurement method are as follows.
- the negative type negative photosensitive resin composition of the present invention can be suitably used in the field of photosensitive materials useful for the production of electric / electronic materials such as semiconductor devices, multilayer wiring boards and the like.
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Abstract
Description
この問題を解決する手段として、特許文献1には、ポリイミド前駆体における側鎖の一部にエチレングリコール構造を有する炭素数5~30の脂肪族基を導入することにより、ポリイミド前駆体を含む感光性樹脂組成物を形成したときの透明性が向上し、さらに熱硬化後に硬化膜のヤング率が向上する感光性樹脂組成物が開示されている。
[1](A)下記一般式(1):
から選ばれる1価の有機基であり、そしてR1及びR2の全てに対する上記一般式(2)で表される1価の有機基と上記一般式(3)で表される1価の有機基の合計の割合は、80モル%以上であり、かつR1及びR2の全てに対する上記一般式(3)で表される1価の有機基の割合は、1モル%~90モル%である。}
で表される単位構造を有するポリイミド前駆体:100質量部;及び
(B)ラジカル型光重合開始剤:0.1質量部~20質量部;
を含むネガ型感光性樹脂組成物。
[2] 前記R6が、下記式(4):
(Z1は水素、又は炭素原子数1~14のアルキル基であり、
Z2は炭素原子数1~14のアルキル基であり、
Z3は炭素原子数1~14のアルキル基であり、
但し、Z1、Z2及びZ3は相互に同じでも異なってもよく、
Z1、Z2及びZ3の炭素原子数の合計が4以上である。)で表される、[1]に記載のネガ型感光性樹脂組成物。
[3]前記R6が、以下の式(3-1)~式(3-7)から選ばれる、[1]又は[2]に記載のネガ型感光性樹脂組成物。
[4]前記(A)ポリイミド前駆体:100質量部に対して、(C)架橋性化合物:0.1質量部~30質量部をさらに含む、[1]~[3]のいずれか1項に記載のネガ型感光性樹脂組成物。
[5][1]~[4]の何れか1項に記載のネガ型感光性樹脂組成物からなる塗布膜の焼成物であることを特徴とするネガ型感光性樹脂膜。
[6]以下の工程:
(1)[1]~[4]のいずれか1項に記載のネガ型感光性樹脂組成物を基板上に塗布して、感光性樹脂層を該基板上に形成する工程と、
(2)該感光性樹脂層を露光する工程と、
(3)該露光後の感光性樹脂層を現像して、レリーフパターンを形成する工程と、
(4)該レリーフパターンを加熱処理して、硬化レリーフパターンを形成する工程と
を含む硬化レリーフパターンの製造方法。
[7][6]に記載の方法により製造された硬化レリーフパターン。
[8]半導体素子と、該半導体素子の上部又は下部に設けられた硬化膜とを備える半導体装置であって、該硬化膜は、[6]に記載の硬化レリーフパターンである、半導体装置。
本発明のネガ型感光性樹脂組成物は、(A)ポリイミド前駆体、(B)ラジカル型光重合開始剤、所望により、(C)架橋性化合物、及び所望により、その他の成分を含む。各成分を以下に順に説明する。
実施の形態では、(A)ポリイミド前駆体は、ネガ型感光性樹脂組成物に含まれる樹脂成分であり、下記一般式(1)で表される構造を有するポリアミドである。
で表される1価の有機基であり、R1及びR2の全てに対する上記一般式(2)で表される1価の有機基と上記一般式(3)で表される1価の有機基の合計は、80モル%以上であり、かつR1及びR2の全てに対する上記一般式(3)で表される1価の有機基の割合は、1モル%~90モル%である。}
上記一般式(1)中、X1は、炭素原子数6~40の4価の有機基であれば限定されないが、耐熱性と感光特性とを両立するという観点で、好ましくは、-COOR1基及び-COOR2基と-CONH-基とが互いにオルト位置にある芳香族基、又は脂環式脂肪族基である。また、X1で表される4価の有機基は、芳香族環を含有する炭素原子数6~40の有機基であることがより好ましい。
R1及びR2は、各々1種又は2種以上の組み合わせでもよいが、好ましくは各々3種以下の組み合わせであり、好ましくは各々2種の組み合わせであり、最も好ましくは各々1種である。
Z2は炭素原子数1~14のアルキル基であり、
Z3は炭素原子数1~14のアルキル基であり、
但し、Z1、Z2及びZ3は相互に同じでも異なってもよく、
Z1、Z2及びZ3の炭素原子数の合計が4以上である。)で表されるものであることが好ましい。
Z1、Z2及びZ3は炭素原子数2~12のアルキル基であることが好ましく、炭素原子数2~10のアルキル基であることが好ましい。
Z1、Z2及びZ3の炭素原子数の合計は5以上であることが好ましく、6以上であることが好ましく、10以上であることが好ましく、12以上であることが好ましく、14以上であることが好ましく、15以上であることが好ましく、16以上であることが好ましい。
Z1、Z2及びZ3の炭素原子数の合計は6以上20以下であることが好ましい。
Z1、Z2及びZ3の炭素原子数の合計の上限は28であることが好ましい。
[(A)ポリイミド前駆体の調製方法]
本実施形態における上記一般式(1)で表されるポリイミド前駆体は、例えば、前述の炭素数6~40の4価の有機基X1を含むテトラカルボン酸二無水物と、(a)上記一般式(2)で表される1価の有機基と水酸基とが結合して成るアルコール類、及び(b)上記一般式(3)で表される1価の有機基と水酸基とが結合して成るアルコール類を反応させて、部分的にエステル化したテトラカルボン酸(以下、アシッド/エステル体ともいう)を調製し、続いて前述の炭素数6~40の2価の有機基Y1を含むジアミン類と重縮合させることにより得られる。
(アシッド/エステル体の調製)
本実施形態において、炭素数6~40の4価の有機基X1を含むテトラカルボン酸二無水物としては、例えば、無水ピロメリット酸、ジフェニルエーテル-3,3’,4,4’-テトラカルボン酸二無水物(=4,4’-オキシジフタル酸二無水物)、ベンゾフェノン-3,3’,4,4’-テトラカルボン酸二無水物、ビフェニル-3,3’,4,4’-テトラカルボン酸二無水物、ジフェニルスルホン-3,3’,4,4’-テトラカルボン酸二無水物、ジフェニルメタン-3,3’,4,4’-テトラカルボン酸二無水物、2,2-ビス(3,4-無水フタル酸)プロパン、2,2-ビス(3,4-無水フタル酸)-1,1,1,3,3,3-ヘキサフルオロプロパン等を挙げることができる。
また、下記式(5-1-a)~式(5-7-a)で表されるテトラカルボン酸二無水物も例示される。
以下の市販品を使用してもよい。
式(3-1)の構造を含むアルコール類:ファインオキソコール(登録商標)180(日産化学工業(株)製)、
式(3-2)の構造を含むアルコール類:ファインオキソコール(登録商標)2000(日産化学工業(株)製)、
式(3-3)の構造を含むアルコール類:ファインオキソコール(登録商標)180N(日産化学工業(株)製)、
式(3-4)又は式(3-5)の構造を含むアルコール類:ファインオキソコール(登録商標)180T(日産化学工業(株)製)、
式(3-6)の構造を含むアルコール類:ファインオキソコール(登録商標)1600K(日産化学工業(株)製)。
これらのアルコール類として、上記式(3-1)~式(3-6)の構造を有するアルコール類を使用することが好ましい。
(ポリイミド前駆体の調製)
上記アシッド/エステル体(典型的には上記反応溶媒中の溶液)に、氷冷下、既知の脱水縮合剤、例えば、ジシクロヘキシルカルボジイミド、1-エトキシカルボニル-2-エトキシ-1,2-ジヒドロキノリン、1,1-カルボニルジオキシ-ジ-1,2,3-ベンゾトリアゾール、N,N’-ジスクシンイミジルカーボネート等を投入混合してアシッド/エステル体をポリ酸無水物とした後、これに、炭素数6~40の2価の有機基Y1を含むジアミン類を別途溶媒に溶解又は分散させたものを滴下投入し、重縮合させることにより、実施の形態で用いることができるポリイミド前駆体を得ることができる。
また、下記式(8-1)で表されるジアミン類も挙げられる。
本発明のネガ型感光性樹脂組成物は、(B)成分としてラジカル型光重合開始剤を含む。その光重合開始剤として、光硬化時に使用する光源に吸収をもつ化合物であれば特に限定されないが、例えば、tert-ブチルペルオキシ-iso-ブチレート、2,5-ジメチル-2,5-ビス(ベンゾイルジオキシ)ヘキサン、1,4-ビス[α-(tert-ブチルジオキシ)-iso-プロポキシ]ベンゼン、ジ-tert-ブチルペルオキシド、2,5-ジメチル-2,5-ビス(tert-ブチルジオキシ)ヘキセンヒドロペルオキシド、α-(iso-プロピルフェニル)-iso-プロピルヒドロペルオキシド、tert-ブチルヒドロペルオキシド、1,1-ビス(tert-ブチルジオキシ)-3,3,5-トリメチルシクロヘキサン、ブチル-4,4-ビス(tert-ブチルジオキシ)バレレート、シクロヘキサノンペルオキシド、2,2’,5,5’-テトラ(tert-ブチルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’-テトラ(tert-ブチルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’-テトラ(tert-アミルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’-テトラ(tert-ヘキシルペルオキシカルボニル)ベンゾフェノン、3,3’-ビス(tert-ブチルペルオキシカルボニル)-4,4’-ジカルボキシベンゾフェノン、tert-ブチルペルオキシベンゾエート、ジ-tert-ブチルジペルオキシイソフタレート等の有機過酸化物;9,10-アントラキノン、1-クロロアントラキノン、2-クロロアントラキノン、オクタメチルアントラキノン、1,2-ベンズアントラキノン等のキノン類;ベンゾインメチル、ベンゾインエチルエーテル、α-メチルベンゾイン、α-フェニルベンゾイン等のベンゾイン誘導体;2,2-ジメトキシ-1,2-ジフェニルエタン-1-オン、1-ヒドロキシ-シクロヘキシル-フェニル-ケトン、2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン、1-[4-(2-ヒドロキシエトキシ)-フェニル]-2-ヒドロキシ-2-メチル-1-プロパン-1-オン、2-ヒドロキシ-1-[4-{4-(2-ヒドロキシ-2-メチル-プロピオニル)ベンジル}-フェニル]-2-メチル-プロパン-1-オン、フェニルグリオキシリックアシッドメチルエステル、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノプロパン-1-オン、2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-1-ブタノン、2-ジメチルアミノ-2-(4-メチル-ベンジル)-1-(4-モルホリン-4-イル-フェニル)-ブタン-1-オン等のアルキルフェノン系化合物;ビス(2,4,6-トリメチルベンゾイル)-フェニルホスフィンオキサイド、2,4,6-トリメチルベンゾイル-ジフェニル-ホスフィンオキサイド等のアシルホスフィンオキサイド系化合物;2-(O-ベンゾイルオキシム)-1-[4-(フェニルチオ)フェニル]-1,2-オクタンジオン、1-(O-アセチルオキシム)-1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]エタノン等のオキシムエステル系化合物が挙げられる。
上記ラジカル型光重合開始剤は、市販品として入手が可能であり、例えば、IRGACURE[登録商標]651、同184、同2959、同127、同907、同369、同379EG、同819、同819DW、同1800、同1870、同784、同OXE01、同OXE02、同250、同1173、同MBF、同TPO、同4265、同TPO(以上、BASF社製)、KAYACURE[登録商標]DETX、同MBP、同DMBI、同EPA、同OA(以上、日本化薬(株)製)、VICURE-10、同55(以上、STAUFFER Co.LTD製)、ESACURE KIP150、同TZT、同1001、同KTO46、同KB1、同KL200、同KS300、同EB3、トリアジン-PMS、トリアジンA、トリアジンB(以上、日本シイベルヘグナー(株)製)、アデカオプトマーN-1717、同N-1414、同N-1606(以上、(株)ADEKA製)が挙げられる。これらのラジカル型光重合開始剤は、単独で用いてもよく、二種以上を組み合わせて用いてもよい。
(B)ラジカル型光重合開始剤の配合量は、(A)ポリイミド前駆体100質量部に対し、0.1質量部~20質量部であり、光感度特性の観点から0.5質量部~15質量部が好ましい。(B)ラジカル型光重合開始剤を(A)ポリイミド前駆体100質量部に対し0.1質量部以上配合することでネガ型感光性樹脂組成物は光感度に優れ、一方で、20質量部以下配合することでネガ型感光性樹脂組成物は厚膜硬化性に優れる。
実施の形態では、ネガ型感光性樹脂組成物は、更に(C)架橋性化合物を含むことが好ましい。架橋性化合物は、ネガ型感光性樹脂組成物を用いて形成されたレリーフパターンを光硬化するときに、(A)ポリイミド前駆体を架橋できるか、又は架橋性化合物自身が架橋ネットワークを形成できる架橋剤であることができる。(C)架橋性化合物は、ネガ型感光性樹脂組成物から形成された硬化膜の耐熱性及び耐薬品性を更に強化することができるため好ましい。前記塗膜を露光する際に使用される光源として、例えば、g線、h線、i線、ghi線ブロードバンド、及びKrFエキシマレーザーが挙げられる。露光量は25mJ/cm2~1000mJ/cm2が望ましい。
実施の形態では、レリーフパターンの解像性を向上させるために、光重合性の不飽和結合を有するモノマーを任意にネガ型感光性樹脂組成物に配合することができる。このようなモノマーとしては、光重合開始剤によりラジカル重合反応する(メタ)アクリル化合物が好ましく、特に以下に限定するものではないが、ジエチレングリコールジメタクリレート、テトラエチレングリコールジメタクリレートをはじめとする、エチレングリコール又はポリエチレングリコールのモノ又はジアクリレート及びメタクリレート、プロピレングリコール又はポリプロピレングリコールのモノ又はジアクリレート及びメタクリレート、グリセロールのモノ、ジ又はトリアクリレート及びメタクリレート、シクロヘキサンジアクリレート及びジメタクリレート、1,4-ブタンジオールのジアクリレート及びジメタクリレート、1,6-ヘキサンジオールのジアクリレート及びジメタクリレート、ネオペンチルグリコールのジアクリレート及びジメタクリレート、ビスフェノールAのモノ又はジアクリレート及びメタクリレート、ベンゼントリメタクリレート、イソボルニルアクリレート及びメタクリレート、アクリルアミド及びその誘導体、メタクリルアミド及びその誘導体、トリメチロールプロパントリアクリレート及びメタクリレート、グリセロールのジ又はトリアクリレート及びメタクリレート、ペンタエリスリトールのジ、トリ、又はテトラアクリレート及びメタクリレート、並びにこれら化合物のエチレンオキサイド又はプロピレンオキサイド付加物等の化合物を挙げることができる。
例えば、二官能(メタ)アクリレートが挙げられる。ここで二官能(メタ)アクリレートとは、分子の両端にアクリロイル基又はメタクリロイル基を有する化合物である。その化合物として、例えば、トリシクロデカンジメタノールジアクリレート、トリシクロデカンジメタノールジメタクリレート、トリシクロデカンジエタノールジアクリレート、及びトリシクロデカンジエタノールジメタクリレートが挙げられる。
上記二官能(メタ)アクリレートは、市販品として入手が可能であり、例えば、A-DCP、DCP(以上、新中村化学工業(株)製)、ニューフロンティア(登録商標)HBPE-4(第一工業製薬(株)製)が挙げられる。これらの化合物は、単独で用いてもよく、二種以上を組み合わせて用いてもよい。
本発明のネガ型感光性樹脂組成物における(C)架橋性化合物の含有量は、前記(A)ポリイミド前駆体:100質量部に対して、(C)架橋性化合物:0.1質量部~50質量部であれば限定されない。その中で0.5質量部~30質量部であることが好ましい。該配合量が0.1質量部以上である場合、良好な耐熱性及び耐薬品性が発現し、一方、50質量部以下である場合、保存安定性に優れるので好ましい。上記含有量は、例えば二種以上用いる場合は、それらの合計の含有量である。
実施の形態では、ネガ型感光性樹脂組成物は、上記(A)~(C)成分以外の成分をさらに含有してもよい。その他の成分としては、例えば、溶剤、前記(A)ポリイミド前駆体以外の樹脂成分、増感剤、接着助剤、熱重合禁止剤、アゾール化合物、ヒンダードフェノール化合物、フィラーなどが挙げられる。
熱架橋剤としては、ヘキサメトキシメチルメラミン、テトラメトキシメチルグリコールウリル、テトラメトキシメチルベンゾグアナミン、1,3,4,6-テトラキス(メトキシメチル)グリコールウリル、1,3,4,6-テトラキス(ブトキシメチル)グリコールウリル、1,3,4,6-テトラキス(ヒドロキシメチル)グリコールウリル、1,3-ビス(ヒドロキシメチル)尿素、1,1,3,3-テトラキス(ブトキシメチル)尿素及び1,1,3,3-テトラキス(メトキシメチル)尿素などが挙げられる。
フィラーとしては、例えば無機フィラーが挙げられ、具体的にはシリカ、窒化アルミ二ウム、窒化ボロン、ジルコニア、アルミナなどのゾルが挙げられる。
これらの樹脂成分の配合量は、(A)ポリイミド前駆体100質量部に対して、好ましくは0.01質量部~20質量部の範囲である。
硬化レリーフパターンの製造方法
実施の形態では、以下の工程(1)~(4):
(1)実施の形態のネガ型感光性樹脂組成物を基板上に塗布して、感光性樹脂層を該基板上に形成する工程、
(2)該感光性樹脂層を露光する工程、
(3)該露光後の感光性樹脂層を現像して、レリーフパターンを形成する工程、及び
(4)該レリーフパターンを加熱処理して、硬化レリーフパターンを形成する工程
を含む、硬化レリーフパターンの製造方法を提供することができる。
本工程では、実施の形態のネガ型感光性樹脂組成物を基材上に塗布し、必要に応じて、その後に乾燥させて、感光性樹脂層を形成する。塗布方法としては、従来から感光性樹脂組成物の塗布に用いられていた方法、例えば、スピンコーター、バーコーター、ブレードコーター、カーテンコーター、スクリーン印刷機等で塗布する方法、スプレーコーターで噴霧塗布する方法等を用いることができる。
本工程では、上記(1)工程で形成した感光性樹脂層を、コンタクトアライナー、ミラープロジェクション、ステッパー等の露光装置を用いて、パターンを有するフォトマスク又はレチクルを介して又は直接に、紫外線光源等により露光する。
(3)該露光後の感光性樹脂層を現像して、レリーフパターンを形成する工程
本工程では、露光後の感光性樹脂層のうち未露光部を現像除去する。露光(照射)後の感光性樹脂層を現像する現像方法としては、従来知られているフォトレジストの現像方法、例えば、回転スプレー法、パドル法、超音波処理を伴う浸漬法等の中から任意の方法を選択して使用することができる。また、現像の後、レリーフパターンの形状を調整する等の目的で、必要に応じて、任意の温度及び時間の組合せによる現像後ベークを施してもよい。現像に使用される現像液としては、例えば、N-メチル-2-ピロリドン、N-シクロヘキシル-2-ピロリドン、N,N-ジメチルアセトアミド、シクロペンタノン、シクロヘキサノン、γ-ブチロラクトン、α-アセチル-γ-ブチロラクトン等が好ましい。また、各溶媒を2種以上、例えば数種類組合せて用いることもできる。
(4)該レリーフパターンを加熱処理して、硬化レリーフパターンを形成する工程
本工程では、上記現像により得られたレリーフパターンを加熱して感光成分を希散させるとともに、(A)ポリイミド前駆体をイミド化させることによって、ポリイミドから成る硬化レリーフパターンに変換する。加熱硬化の方法としては、例えば、ホットプレートによるもの、オーブンを用いるもの、温度プログラムを設定できる昇温式オーブンを用いるもの等種々の方法を選ぶことができる。加熱は、例えば、130℃~250℃で30分~5時間の条件で行うことができる。加熱硬化時の雰囲気気体としては空気を用いてもよく、窒素、アルゴン等の不活性ガスを用いることもできる。
実施の形態では、上述した硬化レリーフパターンの製造方法により得られる硬化レリーフパターンを有して成る、半導体装置も提供される。したがって、半導体素子である基材と、上述した硬化レリーフパターン製造方法により該基材上に形成されたポリイミドの硬化レリーフパターンとを有する半導体装置が提供されることができる。また、本発明は、基材として半導体素子を用い、上述した硬化レリーフパターンの製造方法を工程の一部として含む半導体装置の製造方法にも適用できる。本発明の半導体装置は、上記硬化レリーフパターン製造方法で形成される硬化レリーフパターンを、表面保護膜、層間絶縁膜、再配線用絶縁膜、フリップチップ装置用保護膜、又はバンプ構造を有する半導体装置の保護膜等として形成し、既知の半導体装置の製造方法と組合せることで製造することができる。
実施の形態では、表示体素子と該表示体素子の上部に設けられた硬化膜とを備える表示体装置であって、該硬化膜は上述の硬化レリーフパターンである表示体装置が提供される。ここで、当該硬化レリーフパターンは、当該表示体素子に直接接して積層されていてもよく、別の層を間に挟んで積層されていてもよい。例えば、該硬化膜として、TFT液晶表示素子及びカラーフィルター素子の表面保護膜、絶縁膜、及び平坦化膜、MVA型液晶表示装置用の突起、並びに有機EL素子陰極用の隔壁を挙げることができる。
本明細書の下記合成例に示す重量平均分子量は、ゲルパーミエーションクロマトグラフィー(以下、本明細書ではGPCと略称する。)による測定結果である。測定には東ソー(株)製GPC装置(HLC-8320GPC)を用い、測定条件等は次のとおりである。
GPCカラム:KD-803,KD-805(Shodex製)
カラム温度:50℃
溶媒:N,N-ジメチルホルムアミド(DMF,関東化学,特級),臭化リチウム一水和物(関東化学,鹿特級)(30mM)/リン酸(Aldrich)(30mM)/テトラヒドロフラン(THF,関東化学,特級)(1%)
流量:1.0mL/分
標準試料:ポリスチレン(ジーエルサイエンス製)
<製造例1>(ポリイミド前駆体としてのポリマー(2B)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))40.00g(0.129mol)を1リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)29.15g(0.227mol)とファインオキソコール(登録商標)180(日産化学工業(株)製)6.70g(0.025mol)とγ―ブチロラクトン(関東化学,鹿特級)116gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)20.49g(0.259mol)を加えた後に25℃まで昇温し、24時間撹拌した。
得られた反応混合物を600gのエタノール(関東化学,特級)に加えて粗ポリマーから成る沈殿物を生成した。沈殿物をろ過し、テトラヒドロフラン(THF,関東化学,特級)340gに溶解して粗ポリマー溶液を得た。得られた粗ポリマー溶液を7.2kgの水に滴下してポリマーを沈殿させ、得られた沈殿物を濾別した後、真空乾燥して繊維状のポリマー(2B)を得た。ポリマー1Bの分子量をGPC(標準ポリスチレン換算)で測定したところ、重量平均分子量(Mw)は24,181であった。収率は67.9%であった。この反応生成物は、下記式(2B)で表される繰り返し単位構造を有する。
<製造例2>(ポリイミド前駆体としてのポリマー(1B)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))40.00g(0.129mol)を1リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)16.53g(0.129mol)とファインオキソコール(登録商標)180(日産化学工業(株)製)34.19g(0.129mol)とγ―ブチロラクトン(関東化学,鹿特級)116gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)20.91g(0.264mol)を加えた後に25℃まで昇温し、25時間撹拌した。
得られた反応混合物を600gのエタノール(関東化学,特級)に加えて粗ポリマーから成る沈殿物を生成した。上澄み液をデカンテーションして粗ポリマーを分離し、テトラヒドロフラン340gに溶解して粗ポリマー溶液を得た。得られた粗ポリマー溶液を7.2kgの水に滴下してポリマーを沈殿させ、得られた沈殿物を濾別した後、真空乾燥して繊維状のポリマー(1B)を得た。ポリマー1Bの分子量をGPC(標準ポリスチレン換算)で測定したところ、重量平均分子量(Mw)は20,112であった。収率は50.8%であった。この反応生成物は、下記式(1B)で表される繰り返し単位構造を有する。
<製造例3>(ポリイミド前駆体としてのポリマー(1A)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))40.00g(0.129mol)を1リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)16.20g(0.126mol)とトリエチレングリコールモノメチルエーテル(東京化成工業(株))20.75g(0.126mol)とγ―ブチロラクトン(関東化学,鹿特級)116gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)20.49g(0.259mol)を加えた後に25℃まで昇温し、23時間撹拌した。
<製造例4>(ポリイミド前駆体としてのポリマー1Cの合成)
4,4’-オキシジフタル酸二無水物(ODPA)30.00g(0.095mol)を1リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)12.15g(0.095mol)とトリエチレングリコールモノメチルエーテル(東京化成工業(株))15.56g(0.095mol)とγ―ブチロラクトン(関東化学,鹿特級)87gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)15.37g(0.194mol)を加えた後に25℃まで昇温し、23時間撹拌した。
<製造例5>(ポリイミド前駆体としてのポリマー(3B)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))29.99g(0.097mol)を1リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)23.56g(0.184mol)とファインオキソコール180(日産化学工業(株)製)2.57g(0.010mol)とγ―ブチロラクトン(関東化学,鹿特級)87gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)15.69g(0.198mol)を加えた後に25℃まで昇温し、23時間撹拌した。
<製造例6>(ポリイミド前駆体としてのポリマー(4B)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))30.00g(0.097mol)を1リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)24.54g(0.191mol)とファインオキソコール180(日産化学工業(株)製)0.52g(0.002mol)とγ―ブチロラクトン(関東化学,鹿特級)87gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)15.69g(0.198mol)を加えた後に25℃まで昇温し、23時間撹拌した。
<製造例7>(ポリイミド前駆体としてのポリマー(5B)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))20.00g(0.064mol)を1リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)8.09g(0.063mol)と2-エチル-1-ヘキサノール(東京化成工業(株)製)8.10g(0.063mol)とγ―ブチロラクトン(関東化学,鹿特級)58gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)10.24g(0.130mol)を加えた後に25℃まで昇温し、22.5時間撹拌した。
<製造例8>(ポリイミド前駆体としてのポリマー(6B)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))13.00g(0.042mol)を0.3リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)5.37g(0.042mol)と3-メチル-1-ブタノール3.62g(0.042mol)とγ―ブチロラクトン(関東化学,鹿特級)37.7gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)6.80g(0.086mol)を加えた後に25℃まで昇温し、24時間撹拌した。
得られた反応混合物を650gのメタノール(関東化学,特級)に加えて粗ポリマーから成る沈殿物を生成した。沈殿物をろ過し、テトラヒドロフラン(THF,関東化学,特級)110gに溶解して粗ポリマー溶液を得た。得られた粗ポリマー溶液を650kgの水に滴下してポリマーを沈殿させ、得られた沈殿物を濾別した後、真空乾燥して繊維状のポリマー(6B)を得た。ポリマー(6B)の分子量をGPC(標準ポリスチレン換算)で測定したところ、重量平均分子量(Mw)は14102であった。この反応生成物は、下記式(6B)で表される繰り返し単位構造を有する。
<製造例9>(ポリイミド前駆体としてのポリマー(7B)の合成)
4,4’-オキシジフタル酸二無水物(ODPA、東京化成工業(株))13.00g(0.042mol)を0.3リットル容量の四口フラスコに入れ、2-ヒドロキシエチルメタクリレート(HEMA,Aldrich)5.37g(0.042mol)とエタノール1.89g(0.042mol)とγ―ブチロラクトン(関東化学,鹿特級)37.7gを入れて10℃以下に冷却して攪拌し、攪拌しながらピリジン(関東化学,脱水)6.80g(0.086mol)を加えた後に25℃まで昇温し、24時間撹拌した。
得られた反応混合物を650gのメタノール(関東化学,特級)に加えて粗ポリマーから成る沈殿物を生成した。沈殿物をろ過し、テトラヒドロフラン(THF,関東化学,特級)110gに溶解して粗ポリマー溶液を得た。得られた粗ポリマー溶液を650kgの水に滴下してポリマーを沈殿させ、得られた沈殿物を濾別した後、真空乾燥して繊維状のポリマー(7B)を得た。ポリマー(7B)の分子量をGPC(標準ポリスチレン換算)で測定したところ、重量平均分子量(Mw)は12401であった。この反応生成物は、下記式(7B)で表される繰り返し単位構造を有する。
<実施例1>
製造例1で得られたポリマーを8.00g、IRGACURE[登録商標]OXE01(BASF社製)0.16g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)0.80g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)0.80gを、シクロヘキサノン27.78gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性樹脂組成物を調製した。
<実施例2>
製造例2で得られたポリマーを11.40g、IRGACURE[登録商標]OXE01(BASF社製)0.23g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)1.14g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)1.14gを、シクロヘキサノン28.23gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性樹脂組成物を調製した。
<実施例3>
製造例5で得られたポリマーを11.00g、IRGACURE[登録商標]OXE01(BASF社製)0.22g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)1.10g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)1.10gを、シクロヘキサノン24.92gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性絶縁膜組成物を調製した。
<実施例4>
製造例6で得られたポリマーを9.00g、IRGACURE[登録商標]OXE01(BASF社製)0.18g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)0.90g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)0.90gを、シクロヘキサノン20.39gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性絶縁膜組成物を調製した。
<実施例5>
製造例7で得られたポリマーを9.00g、IRGACURE[登録商標]OXE01(BASF社製)0.18g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)0.90g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)0.90gを、シクロヘキサノン20.39gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性絶縁膜組成物を調製した。
<比較例1>
製造例3で得られたポリマーを9.00g、IRGACURE[登録商標]OXE01(BASF社製)0.18g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)0.90g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)0.90gを、N-メチル2-ピロリドン19.52gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性樹脂組成物を調製した。
<比較例2>
製造例4で得られたポリマーを9.00g、IRGACURE[登録商標]OXE01(BASF社製)0.18g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)0.90g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)0.90gを、N-メチル2-ピロリドン19.52gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性樹脂組成物を調製した。
<参考例1>
製造例8で得られたポリマーを9.00g、IRGACURE[登録商標]OXE01(BASF社製)0.18g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)0.90g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)0.90gを、N-メチル2-ピロリドン19.52gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性樹脂組成物を調製した。
<参考例2>
製造例9で得られたポリマーを9.00g、IRGACURE[登録商標]OXE01(BASF社製)0.18g、トリシクロデカンジメタノールジアクリレート(新中村化学工業(株)製)0.90g、及びニューフロンティア(登録商標)HBPE-4、(第一工業製薬(株)製)0.90gを、N-メチル2-ピロリドン19.52gに溶解させ組成物を調製した。その後、孔径5μmのポリプロピレン製マイクロフィルターを用いてろ過して、ネガ型感光性樹脂組成物を調製した。
実施例1~5及び比較例1、2、参考例1、2で調製したネガ型感光性樹脂組成物を、アルミを積層させたシリコンウェハー上にスピンコーターを用いて塗布し、100℃でプリベークし、アライナー(PLA-501、キヤノン(株)製)を用い露光(i線、露光量:500mJ/cm2)、さらに100℃でベーク後、さらに160℃でベークし膜厚10μmの膜を形成した。その後6N塩酸中に浸漬させた。アルミが溶解し膜が浮き上がったところを回収し、縦3cm、横9cmにカットし自立膜を得た。この自立膜を用いて摂動方式空洞共振器法(装置:TMR-1A、キーコム(株)製)にて1GHzにおける比誘電率、誘電正接を算出した。測定方法の詳細は以下の通りである。
(測定方法)
摂動方式空洞共振器法
(装置構成)
ベクトルネットワークアナライザ : FieldFox N9926A(キーサイト・テクノロジーズ・インク製)
空洞共振器 : モデル TMR-1A(キーコム(株)製)
キャビティ容積 : 1192822mm^3
測定周波数 : 約1GHz(サンプルの共振周波数に依存)
サンプルチューブ : PTFE製 内径:3mm 長さ:約30mm
測定結果を以下の表1に示す。比較例2については評価膜が脆く、電気特性評価が出来なかった。
Claims (8)
- (A)下記一般式(1):
{式中、X1は、炭素原子数6~40の4価の有機基であり、Y1は、炭素原子数6~40の2価の有機基であり、R1及びR2は、それぞれ独立に、水素原子、又は下記一般式(2)若しくは(3):
(式中、R3、R4及びR5は、それぞれ独立に、水素原子又は炭素原子数1~3の1価の有機基であり、そしてmは、1~10の整数である。*は、一般式(1)のポリアミド酸主鎖に存在するカルボン酸との結合部位である。)
(式中、R6は、炭素原子数1~30のアルキル基から選択される1価の有機基である。*は上記と同一である。)
から選ばれる1価の有機基であり、そしてR1及びR2の全てに対する上記一般式(2)で表される1価の有機基と上記一般式(3)で表される1価の有機基の合計の割合は、80モル%以上であり、かつR1及びR2の全てに対する上記一般式(3)で表される1価の有機基の割合は、1モル%~90モル%である。}
で表される単位構造を有するポリイミド前駆体:100質量部;及び
(B)ラジカル型光重合開始剤:0.1質量部~20質量部;
を含むネガ型感光性樹脂組成物。 - 前記(A)ポリイミド前駆体:100質量部に対して、(C)架橋性化合物:0.1質量部~30質量部をさらに含む、請求項1~3のいずれか1項に記載のネガ型感光性樹脂組成物。
- 請求項1~請求項4の何れか1項に記載のネガ型感光性樹脂組成物からなる塗布膜の焼成物であることを特徴とするネガ型感光性樹脂膜。
- 以下の工程:
(1)請求項1~請求項4のいずれか1項に記載のネガ型感光性樹脂組成物を基板上に塗布して、感光性樹脂層を該基板上に形成する工程と、
(2)該感光性樹脂層を露光する工程と、
(3)該露光後の感光性樹脂層を現像して、レリーフパターンを形成する工程と、
(4)該レリーフパターンを加熱処理して、硬化レリーフパターンを形成する工程と
を含む硬化レリーフパターンの製造方法。 - 請求項6に記載の方法により製造された硬化レリーフパターン。
- 半導体素子と、該半導体素子の上部又は下部に設けられた硬化膜とを備える半導体装置であって、該硬化膜は、請求項6に記載の硬化レリーフパターンである、半導体装置。
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CN201880071449.3A CN111316165A (zh) | 2017-09-01 | 2018-08-29 | 感光性树脂组合物 |
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KR20230113813A (ko) | 2021-01-22 | 2023-08-01 | 아사히 가세이 가부시키가이샤 | 감광성 수지 조성물, 그리고 이것을 사용한 폴리이미드경화막의 제조 방법 및 폴리이미드 경화막 |
KR20220167752A (ko) | 2021-06-14 | 2022-12-21 | 도오꾜오까고오교 가부시끼가이샤 | 감광성 수지 조성물 |
KR20230048604A (ko) | 2021-10-04 | 2023-04-11 | 도오꾜오까고오교 가부시끼가이샤 | 감광성 수지 조성물 |
KR20240072266A (ko) | 2021-10-05 | 2024-05-23 | 도쿄 오카 고교 가부시키가이샤 | 블록 공중합체 |
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KR20200044849A (ko) | 2020-04-29 |
US20200209745A1 (en) | 2020-07-02 |
JP7131557B2 (ja) | 2022-09-06 |
JPWO2019044874A1 (ja) | 2020-10-29 |
CN111316165A (zh) | 2020-06-19 |
TW201921114A (zh) | 2019-06-01 |
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