WO2018066395A1 - 樹脂組成物、硬化膜、半導体装置およびそれらの製造方法 - Google Patents
樹脂組成物、硬化膜、半導体装置およびそれらの製造方法 Download PDFInfo
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- WO2018066395A1 WO2018066395A1 PCT/JP2017/034457 JP2017034457W WO2018066395A1 WO 2018066395 A1 WO2018066395 A1 WO 2018066395A1 JP 2017034457 W JP2017034457 W JP 2017034457W WO 2018066395 A1 WO2018066395 A1 WO 2018066395A1
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Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
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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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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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
- G03F7/027—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
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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
- G03F7/26—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
- G03F7/40—Treatment after imagewise removal, e.g. baking
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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
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/52—Mounting semiconductor bodies in containers
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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
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
- H01L21/565—Moulds
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/12—Mountings, e.g. non-detachable insulating substrates
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/48—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor
- H01L23/482—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor consisting of lead-in layers inseparably applied to the semiconductor body
- H01L23/485—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor consisting of lead-in layers inseparably applied to the semiconductor body consisting of layered constructions comprising conductive layers and insulating layers, e.g. planar contacts
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
- H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/10—Bump connectors; Manufacturing methods related thereto
- H01L2224/11—Manufacturing methods
Definitions
- the present invention relates to a resin composition. More specifically, the present invention relates to a resin composition suitably used for a surface protective film such as a semiconductor element, an interlayer insulating film, and an insulating layer of an organic electroluminescent element.
- a surface protective film such as a semiconductor element, an interlayer insulating film, and an insulating layer of an organic electroluminescent element.
- polyimide resin with excellent heat resistance, electrical insulation, mechanical properties, etc. has been used for surface protection films and interlayer insulation films of semiconductor elements, insulation layers of organic electrolytic elements, and planarization films of thin film transistors (hereinafter referred to as TFT) substrates.
- Resin compositions containing polybenzoxazole resins or polyamideimide resins have been widely used.
- Patent Documents 1, 2, and 3 it is common to form a resin film by spin coating or slit coating of a resin composition.
- various solvents have been conventionally used in resin compositions, and have been selected and applied in view of solubility, applicability, storage stability, developability, and the like (Patent Documents 1, 2, and 3).
- a polyimide precursor, polybenzoxazole precursor or polyamideimide precursor coating is dehydrated and closed by heating to obtain a cured film made of polyimide, polybenzoxazole or polyamideimide, it is usually fired at a high temperature around 350 ° C. Need.
- the surface protective film and the interlayer insulating film have a low temperature of 250 ° C. or lower, more preferably 200 ° C. or lower. There is a need for tree compositions that can be cured by firing.
- resin compositions that can be cured at low temperature include resins such as polyimide, polybenzoxazole, polybenzimidazole, and polybenzothiazole, and a resin composition containing a thermal crosslinking agent (Patent Document 4), alkali-soluble polyamideimide, and photoacid generation.
- Type photosensitive polyamide-imide resin composition (Patent Document 5) containing an agent, a solvent and a crosslinking agent, an alkali-soluble polyimide, a quinonediazide compound, a thermal crosslinking agent, a thermal acid generator and an adhesion improver.
- a polyimide resin composition (Patent Document 6) is known.
- Japanese Patent No. 4911248 Japanese Patent Laying-Open No. 2015-232688 WO2015 / 046332 JP 2007-16214 A JP 2007-240554 A JP 2013-72935 A
- the present invention solves the above-mentioned problems associated with the prior art, is excellent in storage stability and storage stability, and can be cured by heat treatment at a low temperature, while obtaining a cured film having high chemical resistance. Furthermore, it aims at providing the resin composition which can suppress the fall of the device characteristic after the reliability test of the device which applied the cured film.
- the present invention has the following configuration. (1) (A) one or more resins selected from (A) polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, other polyamides, and copolymers thereof, (D) the number of epoxy groups is 3 or more And (E) a compound having a tertiary amide structure having a molecular weight of 60 or more and 1000 or less. (2) A cured film obtained by curing the resin composition. (3) A step of applying the above resin composition onto a substrate and drying to form a resin film, an exposure step of exposing the resin film, a development step of developing the exposed resin film, and a developed resin film The manufacturing method of the cured film including the heat processing process which heat-processes.
- the semiconductor chip is sealed with a sealing resin, the insulating film is disposed on the semiconductor chip and the sealing resin as an interlayer insulating film, and the metal wiring is formed on the interlayer insulating film.
- the semiconductor device according to (5) which is arranged.
- the resin composition of the present invention it is excellent in storage stability and storage stability, and can be cured by heat treatment at a low temperature, and a cured film having high chemical resistance can be obtained. It is possible to suppress a decrease in device characteristics after a reliability test of a device to which the film is applied.
- the resin composition of the present invention comprises (A) one or more resins selected from (A) polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, other polyamides, and copolymers thereof.
- a resin composition comprising a thermal crosslinking agent having 3 or more epoxy groups, and further comprising (E) a compound having a tertiary amide structure having a molecular weight of 60 or more and 1000 or less.
- they may be referred to as (A) component, (D) component, and (E) component, respectively.
- the component (A) is preferably an alkali-soluble resin.
- alkali-soluble means that a solution obtained by dissolving a resin in ⁇ -butyrolactone is applied on a silicon wafer and prebaked at 120 ° C. for 4 minutes to form a prebaked film having a thickness of 10 ⁇ m ⁇ 0.5 ⁇ m.
- the dissolution rate of the pre-baked film obtained from the decrease in film thickness when the film is immersed in a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 23 ⁇ 1 ° C. for 1 minute and then rinsed with pure water is 50 nm / min or more. It means that.
- One or more resins selected from the component (A) component polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, other polyamides, and copolymers thereof have high heat resistance and heat treatment. Since the amount of outgas under the subsequent temperature condition of 160 ° C. or more is small, it is suitably used as a planarizing film, insulating layer, partition wall, protective film, and interlayer insulating film used in organic light emitting devices, display devices, and semiconductor elements.
- the polyimide is not particularly limited as long as it has an imide ring.
- the polyimide precursor is not particularly limited as long as it has a structure that becomes a polyimide having an imide ring by dehydration and ring closure, and polyamic acid, polyamic acid ester, or the like can be used.
- the polybenzoxazole is not particularly limited as long as it has a benzoxazole ring.
- the polybenzoxazole precursor is not particularly limited as long as it has a structure that becomes a polybenzoxazole having a benzoxazole ring by dehydration and ring closure, and polyhydroxyamide or the like can be used.
- the other polyamide is not particularly limited as long as it is a polyamide having a structure other than the polyimide precursor and the polybenzoxazole precursor and has an amide structure in the molecule.
- the said polymer may contain 2 or more types, and may use resin which copolymerized these.
- component (A) More preferable examples of the component (A) include polyimide, polyimide precursor, and polybenzoxazole precursor.
- polyimide a resin having a structural unit represented by the following general formula (1) is preferable.
- polyimide precursor and the polybenzoxazole precursor a resin having a structural unit represented by the following general formula (2) is preferable.
- V represents a 4- to 10-valent organic group
- W represents a 2- to 8-valent organic group.
- p and q each represents an integer in the range of 0-6.
- R 1 represents a group selected from a phenolic hydroxyl group, a carboxy group, a sulfonic acid group, and a thiol group. When p is 2 or more, a plurality of R 1 may be the same or different.
- R 2 represents a group selected from a phenolic hydroxyl group, a carboxy group, a sulfonic acid group, and a thiol group. When q is 2 or more, a plurality of R 2 may be the same or different.
- X and Y each independently represent a divalent to octavalent organic group having 2 or more carbon atoms.
- R 3 and R 4 each independently represent hydrogen or an organic group having 1 to 20 carbon atoms.
- r and s each represent an integer within the range of 0 to 4, and t and u each represent an integer within the range of 0 to 2.
- r + s + t + u 0.
- t> 0, having a carboxy group or a carboxy ester group at the ortho position of the amide group, and having a structure that forms an imide ring by dehydration ring closure.
- the polyamide in the case of a polybenzoxazole precursor, s> 0, a hydroxyl group at the ortho position of the amide group, and a structure in which a benzoxazole ring is formed by dehydration ring closure It is preferable.
- the polyamide (however, except a polyimide precursor and a polybenzoxazole precursor) which has a structure represented by General formula (2) can be used preferably.
- the component (A) preferably has 5 to 100,000 structural units represented by the general formula (1) or (2) in one molecule, more preferably 10 to 100,000.
- the structural unit represented by the general formula (1) or (2) may have another structural unit.
- other structural units include, but are not limited to, a skeleton structure in which two cyclic structures are bonded to a quaternary carbon atom constituting the cyclic structure, and a siloxane structure.
- the structural unit represented by the general formula (1) or (2) is a main structural unit.
- the main structural unit means that 50 mol% or more of the structural unit represented by the general formula (1) or (2) is included in the total number of structural units, and more preferably 70 mol% or more.
- the component (A) preferably contains a group selected from an alkylene group and an alkylene ether group. These groups may contain an aliphatic ring. As the group selected from the alkylene group and the alkylene ether group, a group represented by the following general formula (3) is particularly preferable.
- R 5 to R 8 each independently represents an alkylene group having 1 to 6 carbon atoms.
- R 9 to R 16 each independently represent hydrogen, fluorine, or an alkyl group having 1 to 6 carbon atoms.
- x, y and z each independently represents an integer of 0 to 35.
- the component (A) has a group selected from an alkylene group and an alkylene ether group
- high extensibility can be imparted to a cured film obtained by curing the resin composition containing the component (A).
- the resin is flexible, and an increase in stress that can occur when the imide precursor structure or the benzoxazole precursor structure is closed can be suppressed. For this reason, it is possible to suppress an increase in stress on the substrate wafer accompanying the ring closure of the precursor structure.
- the alkylene group and the alkylene ether group have low ultraviolet ray absorption, the introduction of the alkylene group and the alkylene ether group can improve i-ray transmission and achieve high sensitivity.
- the weight average molecular weight of the alkylene group and alkylene ether group is preferably 600 or more, and more preferably 900 or more, from the viewpoint of obtaining high extensibility in the cured film. Moreover, it is preferable that it is 2,000 or less at the point which can maintain the solubility to an alkaline solution, It is more preferable that it is 1,800 or less, It is further more preferable that it is 1,500 or less.
- the weight average molecular weight (Mw) can be confirmed using GPC (gel permeation chromatography).
- the developing solvent can be measured as N-methyl-2-pyrrolidone (hereinafter sometimes abbreviated as NMP) and can be determined in terms of polystyrene.
- V— (R 1 ) p and in the general formula (2), (OH) r —X— (COOR 3 ) t represents an acid residue.
- V is a tetravalent to 10-valent organic group, and an organic group having 4 to 40 carbon atoms containing an aromatic ring or a cyclic aliphatic group is particularly preferable.
- X is a divalent to octavalent organic group having 2 or more carbon atoms, and among them, an organic group having 4 to 40 carbon atoms containing an aromatic ring or an aliphatic group is preferable.
- acid components include dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis (carboxyphenyl) hexafluoropropane, biphenyldicarboxylic acid, benzophenone dicarboxylic acid, and triphenyldicarboxylic acid; Acid, trimesic acid, diphenyl ether tricarboxylic acid, biphenyl tricarboxylic acid, etc .; examples of tetracarboxylic acid include pyromellitic acid, 3,3 ′, 4,4′-biphenyltetracarboxylic acid, 2,3,3 ′, 4′-biphenyl Tetracarboxylic acid, 2,2 ′, 3,3′-biphenyltetracarboxylic acid, 3,3 ′, 4,4′-diphenyl ether tetracarboxylic acid, 3,3 ′, 4,4′-benzoph
- R 20 represents an oxygen atom, C (CF 3 ) 2 , or C (CH 3 ) 2 .
- R 21 and R 22 represent a hydrogen atom or a hydroxyl group.
- These acids can be used as they are or as acid anhydrides, halides or active esters.
- W— (R 2 ) q in the general formula (1) and (OH) s —Y— (COOR 4 ) u in the general formula (2) represent a diamine residue.
- W and Y are divalent to octavalent organic groups, and among them, an organic group having 4 to 40 carbon atoms containing an aromatic ring or a cyclic aliphatic group is preferable.
- diamine constituting the diamine residue examples include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 1, 4-bis (4-aminophenoxy) benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis (4-aminophenoxy) biphenyl, bis ⁇ 4- (4-aminophenoxy) phenyl ⁇ ether, 1,4-bis (4-aminophenoxy) benzene, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′- Diaminobiphenyl, 3,3′-dimethyl-4,4′-diaminobiphenyl, 3,3′-d
- R 23 represents an oxygen atom, C (CF 3 ) 2 , or C (CH 3 ) 2 .
- R 24 to R 27 each independently represents a hydrogen atom or a hydroxyl group.
- diamines can be used as diamines or as corresponding diisocyanate compounds or trimethylsilylated diamines.
- the component (A) preferably contains a group selected from the alkylene group and the alkylene ether group in W in the general formula (1) or Y in the general formula (2).
- W— in the general formula (1) or Y in the general formula (2) has a group represented by the general formula (3), thereby improving the adhesion to the substrate metal (for example, copper).
- the substrate metal for example, copper
- diamine containing a group selected from an alkylene group and an alkylene ether group include ethylenediamine, 1,3-diaminopropane, 2-methyl-1,3-propanediamine, 1,4-diaminobutane, 1, 5-diaminopentane, 2-methyl-1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane, 1,2-cyclohexanediamine, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, 1,2-bis (aminomethyl) cyclohexane, 1,3- Bis (aminomethyl) cyclohexane, 1,4-
- diamines —S—, —SO—, —SO 2 —, —NH—, —NCH 3 —, —N (CH 2 CH 3 ) —, —N (CH 2 CH 2 CH 3 )
- a bond such as —, —N (CH (CH 3 ) 2 ) —, —COO—, —CONH—, —OCONH—, —NHCONH— may be included.
- diamines containing a group represented by the general formula (3) are preferable.
- the diamine residue containing a group selected from an alkylene group and an alkylene ether group is preferably contained in an amount of 5 to 40 mol%, more preferably 10 to 30 mol% in all diamine residues. By including this residue in this range, the developability with an alkali developer can be improved and the elongation of the resulting cured film can be improved.
- a diamine residue having an aliphatic polysiloxane structure may be copolymerized within a range where the heat resistance is not lowered, and the adhesion to the substrate can be improved.
- the diamine component include those obtained by copolymerizing 1 to 15 mol% of bis (3-aminopropyl) tetramethyldisiloxane, bis (p-aminophenyl) octamethylpentasiloxane, and the like. Copolymerization within this range is preferable from the viewpoint of improving adhesion to a substrate such as a silicon wafer and not reducing the solubility in an alkaline solution.
- a resin having an acidic group at the main chain end can be obtained.
- Preferred examples of the monoamine include 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene and 1-hydroxy-4-amino.
- Preferred examples of the acid anhydride, acid chloride, and monocarboxylic acid include acid anhydrides such as phthalic anhydride, maleic anhydride, nadic acid anhydride, cyclohexanedicarboxylic acid anhydride, and 3-hydroxyphthalic acid anhydride; Carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto Monocarboxylic acids such as -7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, and the like; and monoacid chloride compounds in which the carboxy group of these monocarboxylic acids is converted to an acid chloride; One of dicarboxylic acids such as acid, phthalic acid, maleic acid, cyclo
- Mono acid chloride compounds in which only the carboxy group is converted to an acid chloride active ester compounds obtained by reacting the mono acid chloride compound with N-hydroxybenzotriazole or N-hydroxy-5-norbornene-2,3-dicarboximide It is done. Two or more of these may be used.
- the content of the end-capping agent such as monoamine, acid anhydride, acid chloride, monocarboxylic acid is 2 to 25 mol% with respect to 100 mol% of the total of the acid component and amine component constituting the component (A). Is preferred.
- the end-capping agent introduced into the component (A) can be easily detected by the following method.
- a resin having a terminal blocking agent introduced therein is dissolved in an acidic solution and decomposed into an amine component and an acid component, which are constituent units of the resin, and this is measured by gas chromatography (GC) or NMR measurement.
- GC gas chromatography
- NMR nuclear magnetic resonance
- the component (A) preferably has a weight average molecular weight of 10,000 or more and 50,000 or less. If the weight average molecular weight is 10,000 or more, the mechanical properties of the cured film after curing can be improved. More preferably, the weight average molecular weight is 20,000 or more. On the other hand, a weight average molecular weight of 50,000 or less is preferable because developability with an alkaline solution can be improved.
- the component (A) when two or more kinds of resins are contained as the component (A), it is sufficient that at least one weight average molecular weight is within the above range.
- the component (A) can be produced by a known method.
- a polyimide precursor such as polyamic acid or polyamic acid ester
- a method of reacting tetracarboxylic dianhydride and diamine compound at low temperature a diester is obtained by tetracarboxylic dianhydride and alcohol, and then amine It can be synthesized by a method of reacting in the presence of a condensing agent, a method of obtaining a diester by tetracarboxylic dianhydride and an alcohol, then converting the remaining dicarboxylic acid into an acid chloride and reacting with an amine.
- a polybenzoxazole precursor such as polyhydroxyamide
- it can be obtained by a condensation reaction of a bisaminophenol compound and a dicarboxylic acid.
- a dehydrating condensing agent such as dicyclohexylcarbodiimide (DCC) is reacted with an acid, and a bisaminophenol compound is added thereto, or a solution of a bisaminophenol compound added with a tertiary amine such as pyridine is added to a dicarboxylic acid.
- DCC dicyclohexylcarbodiimide
- polyimide it can be obtained, for example, by dehydrating and ring-closing the polyimide precursor obtained by the above-described method by heating or chemical treatment such as acid or base.
- polybenzoxazole it can be obtained, for example, by subjecting the polybenzoxazole precursor obtained by the above-mentioned method to dehydration and ring closure by heating or chemical treatment such as acid or base.
- the resin composition may contain other alkali-soluble resins in addition to the component (A).
- alkali-soluble resins include phenol resins, polymers containing radically polymerizable monomer units having an alkali-soluble group, siloxane polymers, cyclic olefin polymers, and cardo resins. These resins may be used alone, or a plurality of resins may be used in combination. In that case, when the total of the component (A) and the other alkali-soluble resin is 100 parts by mass, the content of the other alkali-soluble resin is preferably 1 to 50 parts by mass.
- the phenol resin can be obtained by polycondensation of various phenols alone or a mixture thereof with aldehydes such as formalin.
- phenols that constitute the phenol resin include phenol, p-cresol, m-cresol, o-cresol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2 , 6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2,3,4-trimethylphenol, 2,3,5-trimethylphenol, 3,4,5-trimethylphenol, 2,4 , 5-trimethylphenol, methylene bisphenol, methylene bis p-cresol, resorcin, catechol, 2-methyl resorcin, 4-methyl resorcin, o-chlorophenol, m-chlorophenol, p-chlorophenol, 2,3-dichlorophenol, m-methoxyphenol, -Methoxyphenol, p-butoxyphenol, o-ethylphenol, m-ethylphenol, p-ethylphenol, 2,3-diethylphenol, 2,5-diethyl
- aldehydes used for polycondensation with phenols include formalin, paraformaldehyde, acetaldehyde, benzaldehyde, hydroxybenzaldehyde, chloroacetaldehyde, and the like. These can be used alone or as a mixture thereof.
- the phenol resin has a part of hydrogen atoms added to the aromatic ring, an alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group, a hydroxyl group, an alkoxyl group, an alkoxymethyl group, a methylol group, a carboxy group, an ester group.
- the weight average molecular weight of the phenol resin is preferably in the range of 2,000 to 50,000 in terms of polystyrene and preferably in the range of 3,000 to 30,000 using gel permeation chromatography (GPC). More preferred. When the molecular weight is 2,000 or more, the pattern shape, resolution, developability, and heat resistance are excellent. When the molecular weight is 50,000 or less, the sensitivity is excellent.
- Examples of the polymer containing a radical polymerizable monomer unit having an alkali-soluble group include a polymer containing a radical polymerizable monomer unit having a phenolic hydroxyl group or a carboxy group.
- Polymers containing monomer units selected from o-hydroxystyrene, m-hydroxystyrene and p-hydroxystyrene, and their alkyl, alkoxy, alkoxymethyl, and methylol substituents have a sensitivity at the time of patterning, a residual after resolution development. It is preferably used in terms of film ratio, heat resistance, storage stability of the solution, and the like. These may be used alone or in combination of two or more.
- Preferred examples of the other radical polymerizable monomer include styrene, and ⁇ -position, o-position, m-position, p-position alkyl, alkoxy, alkoxymethyl, methylol, halogen, haloalkyl substituents of styrene; butadiene, Isoprene; methyl, ethyl, n-propyl, N-butyl, glycidyl and tricyclo [5.2.1.0 2,6 ] decan-8-yl esters of methacrylic acid or acrylic acid. It is preferably used from the viewpoints of patterning sensitivity, residual film ratio after resolution development, heat resistance, solvent resistance, adhesion to the substrate, storage stability of the solution, and the like. These may be used alone or in combination of two or more.
- the ratio of the other radical polymerizable monomer is the radical polymerizable monomer having the phenolic hydroxyl group. And 5 mass% or more is preferable with respect to the total amount with other radically polymerizable monomers. Moreover, 30 mass% or less is preferable, and 20 mass% or less is more preferable. It is preferable that the ratio of the other radical polymerizable monomer is 5% by mass or more because heat resistance and chemical resistance are improved. Moreover, since it becomes easy for alkali developability to set it as 30 mass% or less, it is preferable.
- a preferred ratio of the other radical polymerizable monomer is a radical polymerizable monomer having a carboxy group and 10 mass% or more is preferable with respect to the total amount with another radically polymerizable monomer.
- 90 mass% or less is preferable, and 80 mass% or less is more preferable. It is preferable to set the ratio of the other radical polymerizable monomer to 10% by mass or more because heat resistance and chemical resistance are improved. Moreover, since it becomes easy for alkali developability to set it as 90 mass% or less, it is preferable.
- the weight average molecular weight of the polymer containing a radically polymerizable monomer having an alkali-soluble group is preferably 2,000 to 100,000, more preferably 3,000 to 50,000 in terms of polystyrene using gel permeation chromatography. Particularly preferred is 5,000 to 30,000.
- the weight average molecular weight is 2,000 or more, the pattern shape, resolution, developability and heat resistance are good.
- the weight average molecular weight is 100,000 or less, developability and sensitivity are improved.
- polymers containing a radically polymerizable monomer having an alkali-soluble group may be used alone or in admixture of two or more.
- an alkali-soluble resin may be synthesized by a method of imparting alkali solubility by introducing a protecting group into a carboxy group or a phenolic hydroxyl group before polymerization and deprotecting after polymerization. Further, the transparency and softening point in visible light may be changed by hydrogenation or the like.
- the siloxane polymer is a siloxane polymer obtained by hydrolytic condensation of organosilane.
- a method of adding a solvent, water, and a catalyst as necessary to organosilane and heating and stirring at 50 to 150 ° C. for about 0.5 to 100 hours can be mentioned.
- hydrolysis by-products alcohols such as methanol
- condensation by-products water
- organosilanes include tetrafunctional silanes such as tetramethoxysilane, tetraethoxysilane, tetraacetoxysilane, and tetraphenoxysilane; methyltrimethoxysilane, methyltriethoxysilane, methyltriisopropoxysilane, phenyltrimethoxysilane, Trifunctional silanes such as phenyltriethoxysilane and p-hydroxyphenyltrimethoxysilane; dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldiacetoxysilane, di-n-butyldimethoxysilane, diphenyldimethoxysilane, (3-glycid Bifunctional such as xylpropyl) methyldimethoxysilane, (3-glycidoxypropyl) methyldiethoxysilane, di (1-naphthyl)
- Examples thereof include silicate 51, M silicate 51 manufactured by Tama Chemical Industry Co., Ltd., silicate 40, silicate 45, methyl silicate 51 manufactured by Colcoat Co., Ltd., methyl silicate 53A, ethyl silicate 40, and the like. Two or more of these organosilanes may be used.
- the weight average molecular weight of the siloxane polymer is not particularly limited, but is preferably 1,000 or more in terms of polystyrene measured by GPC (gel permeation chromatography) because the coating properties are improved.
- the weight average molecular weight is preferably 100,000 or less, and more preferably 50,000 or less.
- the cyclic olefin polymer is a homopolymer or copolymer of a cyclic olefin monomer having a cyclic structure (alicyclic ring or aromatic ring) and a carbon-carbon double bond.
- the cyclic olefin polymer may have a monomer other than the cyclic olefin monomer.
- the monomer for constituting the cyclic olefin polymer includes a cyclic olefin monomer having a protic polar group, a cyclic olefin monomer having a polar group other than protic, and a cyclic olefin monomer having no polar group. And monomers other than cyclic olefins.
- cyclic olefin monomer having a protic polar group examples include 5-hydroxycarbonylbicyclo [2.2.1] hept-2-ene, 5-methyl-5-hydroxycarbonylbicyclo [2.2.1]. ] Hept-2-ene, 8-hydroxycarbonyltetracyclo [4.4.0.1 2,5 .
- Carboxy group-containing cyclic olefin such as 1 7,10 ] dodec-3-ene; 5- (4-hydroxyphenyl) bicyclo [2.2.1] hept-2-ene, 5-methyl-5- (4-hydroxy Phenyl) bicyclo [2.2.1] hept-2-ene, 8- (4-hydroxyphenyl) tetracyclo [4.4.0.1 2,5 .
- a hydroxyl group-containing cyclic olefin such as 17, 10 ] dodec-3-ene.
- cyclic olefin monomer having a polar group other than protic examples include 5-acetoxybicyclo [2.2.1] hept-2-ene, 5-methoxycarbonylbicyclo [2.2.1] hept- 2-ene, 8-acetoxytetracyclo [4.4.0.1 2,5 . 1 7,10 ] dodec-3-ene, a cyclic olefin having an ester group; a cyclic olefin having an N-substituted imide group such as N-phenyl- (5-norbornene-2,3-dicarboximide); 8- Cyanotetracyclo [4.4.0.1 2,5 .
- cyclic olefins having a halogen atom such as 1 7,10 ] dodec-3-ene.
- cyclic olefin monomer having no polar group examples include bicyclo [2.2.1] hept-2-ene, 5-ethyl-bicyclo [2.2.1] hept-2-ene, tricyclo [4.3.0.1 2,5 ] deca-3,7-diene and the like.
- monomers other than cyclic olefins include ⁇ -olefins having 2 to 20 carbon atoms such as ethylene, propylene and 1-butene, and non-conjugated dienes having 2 to 20 carbon atoms such as 1,4-hexadiene.
- a chain olefin is mentioned.
- These monomers may be used alone or in combination of two or more.
- a general method can be used.
- a ring-opening polymerization method or an addition polymerization method can be used.
- the polymerization catalyst for example, metal complexes such as molybdenum, ruthenium and osmium are preferably used. These polymerization catalysts can be used alone or in combination of two or more.
- the cardo resin is a resin having a cardo structure, that is, a skeleton structure in which two cyclic structures are bonded to a quaternary carbon atom constituting the cyclic structure.
- a common cardo structure is a fluorene ring bonded to a benzene ring. Specific examples include a fluorene skeleton, a bisphenol fluorene skeleton, a bisaminophenyl fluorene skeleton, a fluorene skeleton having an epoxy group, a fluorene skeleton having an acrylic group, and the like.
- the cardo resin is formed by polymerizing a skeleton having the cardo structure by a reaction between functional groups bonded thereto.
- the cardo resin has a structure in which a main chain and bulky side chains are connected by one element (cardo structure), and has a ring structure in a direction substantially perpendicular to the main chain.
- the monomer having a cardo structure examples include bis (glycidyloxyphenyl) fluorene type epoxy resin, 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (4-hydroxy-3-methyl).
- bisphenols containing cardo structure such as phenyl) fluorene, 9,9-bis (cyanoalkyl) fluorenes such as 9,9-bis (cyanomethyl) fluorene, 9,9-bis (3-aminopropyl) fluorene, etc.
- 9,9-bis (aminoalkyl) fluorenes It may be a copolymer with other copolymerizable monomers.
- a general method can be used, and examples thereof include a ring-opening polymerization method and an addition polymerization method.
- the resin composition of the present invention may contain (B) a photosensitizer (hereinafter sometimes referred to as (B) component). Photosensitivity can be imparted to the resin composition by containing the component (B).
- B a photosensitizer
- Component (B) is a compound whose chemical structure changes in response to ultraviolet rays, and examples thereof include a photoacid generator, a photobase generator, and a photopolymerization initiator.
- a photoacid generator is used as the component (B)
- an acid is generated in the light irradiation part of the resin composition, and the solubility of the light irradiation part in the alkaline developer is increased.
- a mold pattern can be obtained.
- a photobase generator is used as the component (B)
- a base is generated in the light-irradiated part of the resin composition, and the solubility of the light-irradiated part in an alkaline developer is lowered, so that the light-irradiated part becomes insoluble.
- a mold pattern can be obtained.
- radicals are generated in the light-irradiated part of the resin composition, radical polymerization proceeds, and insolubilization with an alkali developer makes a negative pattern. Can be formed. Further, UV curing at the time of exposure is promoted, and sensitivity can be improved.
- a photoacid generator is preferred in that a highly sensitive and high resolution pattern can be obtained.
- the photoacid generator include quinonediazide compounds, sulfonium salts, phosphonium salts, diazonium salts, and iodonium salts.
- a sensitizer etc. can be included as needed.
- the quinonediazide compound is preferably a compound in which a sulfonic acid of naphthoquinonediazide is bonded with an ester to a compound having a phenolic hydroxyl group.
- a compound having a phenolic hydroxyl group used here, Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, TrisP-SA, TrisOCR-PA, BisOCHP-Z, BisP-MZ, BisP -PZ, BisP-IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, Methylenetris-FR-CR, BisRS-26X, DML-MBPC, DML-MBOC, DML-OCHP, DML-PCHP, DML-PC, DML-PTBP, DML-34X, DML-EP, DML-POP, dimethylol-BisOC-P, DML-PFP, D
- the entire functional group of the compound having a phenolic hydroxyl group is substituted with quinonediazide.
- a quinonediazide compound substituted by 50 mol% or more the affinity of the quinonediazide compound with respect to the aqueous alkaline solution is reduced, and the solubility of the resin composition in the unexposed area in the aqueous alkaline solution is greatly reduced.
- the sulfonyl group is changed to indenecarboxylic acid, and a large dissolution rate of the resin composition having photosensitivity in the exposed portion to the alkaline aqueous solution can be obtained.
- both 5-naphthoquinonediazidosulfonyl group and 4-naphthoquinonediazidesulfonyl group are preferably used.
- the 5-naphthoquinonediazide sulfonyl ester compound has an absorption extending to the g-line region of a mercury lamp and is suitable for g-line exposure and full-wavelength exposure.
- the 4-naphthoquinonediazide sulfonyl ester compound has absorption in the i-line region of a mercury lamp and is suitable for i-line exposure.
- a 4-naphthoquinone diazide sulfonyl ester compound or a 5-naphthoquinone diazide sulfonyl ester compound depending on the wavelength to be exposed can also be obtained.
- a 4-naphthoquinone diazide sulfonyl ester compound and a 5-naphthoquinone diazide sulfonyl ester compound may be used in combination.
- the quinonediazide compound can be synthesized by a known method by an esterification reaction between a compound having a phenolic hydroxyl group and a quinonediazidesulfonic acid compound. By using a quinonediazide compound, resolution, sensitivity, and remaining film rate are further improved.
- the molecular weight of the component (B) is preferably 300 or more, more preferably 350 or more, preferably 3,000 or less, more preferably 1 from the viewpoint of heat resistance, mechanical properties and adhesiveness of the film obtained by heat treatment. , 500 or less.
- a sulfonium salt, a phosphonium salt, and a diazonium salt are preferable because they moderately stabilize the acid component generated by exposure.
- sulfonium salts are preferred.
- the content of the component (B) is preferably 0.1 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the component (A).
- photosensitivity can be imparted while maintaining the heat resistance, chemical resistance and mechanical properties of the film after the heat treatment.
- the content of the component (B) is more preferably 1 part by mass or more and further preferably 3 parts by mass or more with respect to 100 parts by mass of the component (A). Moreover, 100 mass parts or less are more preferable, and 80 mass parts or less are still more preferable. If it is 1 mass part or more and 80 mass parts or less, photosensitivity can be provided, maintaining the heat resistance of the film
- the content of the component (B) is more preferably 0.1 parts by mass or more with respect to 100 parts by mass of the component (A), and 1 part by mass or more. Is more preferable, and 3 parts by mass or more is particularly preferable. Moreover, 100 mass parts or less are more preferable, 80 mass parts or less are more preferable, and 50 mass parts or less are especially preferable. If it is 0.1 mass part or more and 80 mass parts or less, photosensitivity can be provided, maintaining the heat resistance of the film
- the resin composition may contain a compound having a phenolic hydroxyl group for the purpose of supplementing alkali developability.
- a compound having a phenolic hydroxyl group examples include Bis-Z, BisOC-Z, BisOPP-Z, BisP-CP, Bis26X-Z, BisOTBP-Z, BisOCHP-Z, BisOCR-CP, BisP-MZ, BisP-EZ.
- the resin composition contains a compound having these phenolic hydroxyl groups, it hardly dissolves in an alkali developer before exposure, and easily dissolves in an alkali developer when exposed to light. In addition, development is easy in a short time. Therefore, the sensitivity is easily improved.
- photobase generator When a photobase generator is used as the component (B), specific examples of the photobase generator include amide compounds and ammonium salts.
- Examples of the amide compound include 2-nitrophenylmethyl-4-methacryloyloxypiperidine-1-carboxylate, 9-anthrylmethyl-N, N-dimethylcarbamate, 1- (anthraquinone-2-yl) ethylimidazolecarboxylate, (E) -1- [3- (2-hydroxyphenyl) -2-propenoyl] piperidine and the like.
- ammonium salts include 1,2-diisopropyl-3- (bisdimethylamino) methylene) guanidinium 2- (3-benzoylphenyl) propionate, (Z)- ⁇ [bis (dimethylamino) methylidene] amino ⁇ -N. -Cyclohexylamino) methaniminium tetrakis (3-fluorophenyl) borate, 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguanidinium n-butyltriphenylborate and the like.
- the content of the component (B) in the resin composition is preferably 0.1 parts by mass or more with respect to 100 parts by mass of the component (A). 5 parts by mass or more is more preferable, 0.7 parts by mass or more is more preferable, and 1 part by mass or more is particularly preferable.
- the sensitivity at the time of exposure can be improved as content is in the said range.
- the content is preferably 25 parts by mass or less, more preferably 20 parts by mass or less, further preferably 17 parts by mass or less, and particularly preferably 15 parts by mass or less. When the content is within the above range, the resolution after development can be improved.
- examples of the photopolymerization initiator include benzyl ketal photopolymerization initiators, ⁇ -hydroxyketone photopolymerization initiators, and ⁇ -aminoketone photopolymerization initiators. , Acylphosphine oxide photopolymerization initiator, oxime ester photopolymerization initiator, acridine photopolymerization initiator, benzophenone photopolymerization initiator, acetophenone photopolymerization initiator, aromatic ketoester photopolymerization initiator or benzoic acid Ester photopolymerization initiators and titanocene photopolymerization initiators are preferred.
- ⁇ -hydroxyketone photopolymerization initiator ⁇ -aminoketone photopolymerization initiator, acylphosphine oxide photopolymerization initiator, oxime ester photopolymerization initiator, acridine photopolymerization initiator
- An ⁇ -aminoketone photopolymerization initiator, an acylphosphine oxide photopolymerization initiator, and an oxime ester photopolymerization initiator are more preferable.
- Examples of the benzyl ketal photopolymerization initiator include 2,2-dimethoxy-1,2-diphenylethane-1-one.
- Examples of ⁇ -hydroxyketone photopolymerization initiators include 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one and 2-hydroxy-2-methyl-1-phenylpropane-1. -One, 1-hydroxycyclohexyl phenyl ketone, 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methylpropan-1-one or 2-hydroxy-1- [4- [4- ( 2-hydroxy-2-methylpropionyl) benzyl] phenyl] -2-methylpropan-1-one.
- ⁇ -aminoketone photopolymerization initiators include 2-dimethylamino-2-methyl-1-phenylpropan-1-one, 2-diethylamino-2-methyl-1-phenylpropan-1-one, 2- Methyl-2-morpholino-1-phenylpropan-1-one, 2-dimethylamino-2-methyl-1- (4-methylphenyl) propan-1-one, 2-dimethylamino-1- (4-ethylphenyl) ) -2-Methylpropan-1-one, 2-dimethylamino-1- (4-isopropylphenyl) -2-methylpropan-1-one, 1- (4-butylphenyl) -2-dimethylamino-2- Methylpropan-1-one, 2-dimethylamino-1- (4-methoxyphenyl) -2-methylpropan-1-one, 2-dimethylamino-2-methyl -1- (4-methylthiophenyl) propan-1-
- acylphosphine oxide photopolymerization initiator examples include 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, or bis (2,6-dimethoxybenzoyl). )-(2,4,4-trimethylpentyl) phosphine oxide.
- oxime ester photopolymerization initiator examples include 1-phenylpropane-1,2-dione-2- (O-ethoxycarbonyl) oxime, 1-phenylbutane-1,2-dione-2- (O-methoxy).
- Examples of the acridine photopolymerization initiator include 1,7-bis (acridin-9-yl) -n-heptane.
- benzophenone photopolymerization initiator examples include benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-phenylbenzophenone, 4,4-dichlorobenzophenone, 4- Examples include hydroxybenzophenone, alkylated benzophenone, 3,3 ′, 4,4′-tetrakis (t-butylperoxycarbonyl) benzophenone, 4-methylbenzophenone, dibenzylketone or fluorenone.
- acetophenone photopolymerization initiator examples include 2,2-diethoxyacetophenone, 2,3-diethoxyacetophenone, 4-t-butyldichloroacetophenone, benzalacetophenone, and 4-azidobenzalacetophenone.
- aromatic ketoester photopolymerization initiator examples include methyl 2-phenyl-2-oxyacetate.
- benzoate photopolymerization initiator examples include ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid (2-ethyl) hexyl, ethyl 4-diethylaminobenzoate, and methyl 2-benzoylbenzoate.
- titanocene photopolymerization initiators include bis ( ⁇ 5 -2,4-cyclopentadien-1-yl) -bis [2,6-difluoro) -3- (1H-pyrrol-1-yl) phenyl]. Mention may be made of titanium (IV) or bis ( ⁇ 5 -3-methyl-2,4-cyclopentadien-1-yl) -bis (2,6-difluorophenyl) titanium (IV).
- the content of the component (B) in the resin composition is preferably 0.1 parts by mass or more with respect to 100 parts by mass of the component (A), 0.5 More than mass part is more preferable, 0.7 mass part or more is further more preferable, and 1 mass part or more is especially preferable.
- the sensitivity at the time of exposure can be improved as content is in the said range.
- the content is preferably 25 parts by mass or less, more preferably 20 parts by mass or less, further preferably 17 parts by mass or less, and particularly preferably 15 parts by mass or less. When the content is within the above range, the resolution after development can be improved.
- the resin composition further contains a radical polymerizable compound.
- the radical polymerizable compound refers to a compound having a plurality of ethylenically unsaturated double bond groups in the molecule.
- a photopolymerization initiator is contained as the component (B)
- the radical polymerization of the radical polymerizable compound proceeds by exposure to radicals generated from the photopolymerization initiator at the time of exposure by including the radical polymerizable compound.
- a negative pattern can be formed by insolubilizing the exposed portion of the film in an alkaline developer.
- the resin composition contains a radical polymerizable compound, UV curing at the time of exposure is promoted, and the sensitivity at the time of exposure can be improved.
- the crosslink density after thermosetting is improved, and the hardness of the cured film obtained by curing the resin composition can be improved.
- a radically polymerizable compound As a radically polymerizable compound, a methacryl group and / or an acryl group (hereinafter, these are easily abbreviated as a (meth) acryl group.) Compounds with) may be preferred. From the viewpoint of improving the sensitivity during exposure and improving the hardness of the cured film, a compound having two or more (meth) acryl groups in the molecule is more preferable.
- the double bond equivalent of the radical polymerizable compound is preferably from 80 to 400 g / mol from the viewpoint of improving the sensitivity during exposure and improving the hardness of the cured film.
- radical polymerizable compound examples include diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, and trimethylolpropane di (meth) acrylate.
- trimethylolpropane tri (meth) acrylate ditrimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, Pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate, 2,2-bis [ 4- (3- (meth) acryloxy-2-hydroxypropoxy) phenyl] propane, 1,3,5-tris ((meth) acryloxyethyl) isocyanuric acid, 1,3-bis (Met
- a modified product or an ethylene oxide modified product is more preferable.
- a compound obtained by subjecting a compound having two or more glycidoxy groups in the molecule and an unsaturated carboxylic acid having an ethylenically unsaturated double bond group to a ring-opening addition reaction Also preferred are compounds obtained by reacting polybasic acid carboxylic acids or polybasic carboxylic acid anhydrides.
- the content of the radically polymerizable compound is preferably 15 parts by mass or more, more preferably 20 parts by mass or more, further preferably 25 parts by mass or more, and particularly preferably 30 parts by mass or more with respect to 100 parts by mass of the component (A). .
- the sensitivity at the time of exposure can be improved as content is in the said range.
- the content is preferably 65 parts by mass or less, more preferably 60 parts by mass or less, further preferably 55 parts by mass or less, and particularly preferably 50 parts by mass or less.
- the heat resistance of a cured film can be improved as content is in the said range.
- the resin composition of the present invention includes (E) a compound having a tertiary amide structure having a molecular weight of 60 or more and 1000 or less.
- (E) component By containing (E) component, it interacts with (B) component and (D) component mentioned later, and stabilizes (B) component and (D) component. Therefore, for example, when the resin composition is stored at room temperature, the deactivation of the component (B) and the reaction with other components and the reaction with the other components of the component (D) can be suppressed, so that the storage stability Will improve. Moreover, the same effect is expressed also about the resin film obtained from a resin composition. In addition, since the resin film interacts with and stabilizes components such as acid generated during exposure, the stability of leaving after coating and after exposure is also improved.
- the sensitivity is improved.
- the component (E) remains in the cured film and captures the acid and the like generated from the component (B) during the device reliability test. Suppresses corrosion, oxidation, ionization, etc., and suppresses peeling between the cured film and the metal material. That is, it is possible to suppress deterioration of device characteristics after the device reliability test.
- component (E) Since component (E) has a molecular weight of 60 or more and 1,000 or less, interaction with component (B) or component (D) is easily formed, and the stabilizing effect is improved.
- component (E) compounds represented by the general formulas (4) to (6) are preferable.
- Z represents an oxygen atom or a nitrogen atom.
- R 28 represents an alkyl group having 1 to 10 carbon atoms or a group in which the alkyl group is substituted with —CO—, —O—, or —OH.
- R 29 is unsubstituted when Z is an oxygen atom, and when Z is a nitrogen atom, the alkyl group having 1 to 10 carbon atoms, or the alkyl group is substituted by —CO—, —O—, or —OH Represents a group.
- R 30 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a group in which the alkyl group is substituted with —CO—, —O—, or —OH.
- m represents an integer of 0 to 1
- n represents an integer of 1 to 5.
- R 31 to R 34 each independently represents an alkyl group having 1 to 6 carbon atoms.
- R 35 and R 36 each independently represent an alkyl group having 1 to 10 carbon atoms or a group in which the alkyl group is substituted with —CO—, —O—, or —OH.
- R 35 and R 36 may form a cyclic structure.
- R 37 represents an alkyl group having 1 to 20 carbon atoms, an aromatic group, or a group in which the alkyl group or aromatic group is substituted with —CO—, —O—, or —OH.
- Examples of the compound represented by the general formula (4) include the following, but are not limited to the following structures.
- Examples of the compound represented by the general formula (5) include, but are not limited to, the following structures.
- Examples of the compound represented by the general formula (6) include the following, but are not limited to the following structures.
- the component (E) is preferably a compound having a melting point of ⁇ 70 ° C. or higher and 15 ° C. or lower and a boiling point of 100 ° C. or higher and 400 ° C. or lower.
- the melting point and boiling point of the component are within this range, so that the storage stability and placement stability of the resin composition, and the reliability test of the device to which the cured film obtained by curing the resin composition is applied. Later deterioration of device characteristics can be suppressed.
- the melting point of the component (E) is more preferably ⁇ 50 ° C. or higher and 10 ° C. from the viewpoints of handling properties during production, storage stability of the resin composition, and stability of placement.
- the boiling point of the component (E) is 150 ° C.
- the stability can be improved and the deterioration of the device characteristics after the reliability test of the device to which the cured film obtained by curing the resin composition is applied can also be suppressed.
- the content of component (E) is preferably 4 parts by mass or more and 1600 parts by mass or less with respect to 100 parts by mass of component (A).
- the content is more preferably 10 parts by mass or more. Further, the content is more preferably 1000 parts by mass or less.
- content of (E) component is 5 mass% or more and 50 mass% or less among 100 mass% of all the liquid components.
- the liquid component is a component that is liquid at 25 ° C., and corresponds to the component (E) and the component (C) described later.
- the resin composition of the present invention is applied on a substrate so as to be 13 ⁇ m after drying, and the content of the component (E) contained in the resin film obtained by heating and drying at 120 ° C. for 3 minutes is 0.001% by mass or more. It is preferable that it is 30 mass% or less.
- the content of the component (E) contained in the resin film is more preferably 0.002% by mass or more, and further preferably 0.005% by mass or more.
- the content of the component (E) is more preferably 20% by mass or less, and further preferably 10% by mass or less.
- the content of the component (E) contained in the cured film obtained by curing the resin composition is 0.05 ppm or more and 1000 ppm or less.
- the content of (E) contained in a cured film is more preferably 0.1 ppm or more, and further preferably 0.5 ppm or more.
- the content of the component (E) contained in the cured film is more preferably 500 ppm or less, and further preferably 300 ppm or less.
- the resin composition of the present invention may further contain (C) a solvent (hereinafter may be referred to as (C) component).
- C a solvent
- the resin composition can be used as a solution.
- the content of the component (C) in the resin composition is preferably such that the solid content concentration in the resin composition is 5 to 70% by mass, more preferably 10 to 60% by mass.
- the solid content is a component that is solid at 25 ° C., and includes (A) component, (B) component, (D) component, and (F) component.
- the resin composition preferably contains, as component (C), (C1) one or more solvents having a boiling point of 100 ° C. or higher and 150 ° C. or lower under atmospheric pressure.
- the solvent can be removed from the coating film of the resin composition in a short time. Further, since the coating film is further dried, the solubility in the developer in the unexposed area is lowered, and the contrast is increased by increasing the contrast difference between the exposed area and the unexposed area.
- alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether (boiling point 124 ° C.), propylene glycol monomethyl ether (boiling point 120 ° C.), propylene glycol monomethyl ether acetate (boiling point 146 ° C.); propyl acetate (boiling point 102 ° C.) ), Alkyl acetates such as butyl acetate (boiling point 125 ° C.), isobutyl acetate (boiling point 118 ° C.); methyl butyl ketone (boiling point 116 ° C.), methyl isobutyl ketone (boiling point 116 ° C.), methyl propyl ketone (boiling point 102 ° C.), etc.
- Ketones such as n-butyl alcohol
- the content of the component (C1) is preferably 0.1% by mass or more and 40% by mass or less, out of 100% by mass of all liquid components. Sensitivity improves by making content into 0.1 mass% or more. In addition, when the content is 40% by mass or less, uneven coating can be suppressed, and a highly stable material excellent in storage stability, placement stability and in-plane uniformity can be obtained.
- the component (C2) may further contain one or more solvents selected from (C2) a solvent represented by the general formula (10).
- R 50 and R 51 each independently represents an alkyl group having 1 to 10 carbon atoms or an aromatic group. R 50 and R 51 may form a cyclic structure.
- a solvent capable of dissolving the solid content is preferable.
- polar aprotic solvents such as ⁇ -butyrolactone, ⁇ -valerolactone, and ⁇ -valerolactone
- esters such as ethyl acetate, butyl acetate, isobutyl acetate, propyl acetate, methyl benzoate, and ethyl benzoate Etc. Two or more of these may be contained.
- the content of the component (C2) is preferably 10% by mass or more and 94.9% by mass or less in 100% by mass of all liquid components.
- the resin composition of the present invention contains (D) a thermal crosslinking agent having 3 or more epoxy groups.
- the thermal crosslinking agent refers to a compound having at least two thermally reactive functional groups in the molecule.
- the thermally reactive functional group is an alkoxymethyl group, a methylol group, an epoxy group, an oxetanyl group, or the like.
- a thermal crosslinking agent can bridge
- component (D) Since component (D) has three or more epoxy groups in the molecule, it can react at low temperatures, so even if it is cured at low temperatures, component (D) is strongly cross-linked with other additive components. In addition, the chemical resistance of the cured film can be improved. In general, an epoxy compound having 3 or more functional groups has high reactivity, and thus deteriorates the storage stability and retention stability of the resin composition. However, the resin composition of the present invention has the above-mentioned (E). By including the components, storage stability and storage stability are improved.
- component (D) includes the following, but are not limited to the following structures.
- the resin composition contains one or more compounds selected from trifunctional or higher functional alkoxymethyl compounds and trifunctional or higher functional methylol compounds (hereinafter may be abbreviated as the component (D2)). It is preferable to include.
- the component (D2) By including the component (D2), the crosslinking becomes stronger and the chemical resistance of the cured film can be further improved.
- the storage stability and storage stability of the solution are improved by including the component (D2). Further, since the obtained cured film is densified, peeling between the cured film and the metal material during the device reliability test is suppressed. That is, it is possible to suppress deterioration of device characteristics after the device reliability test.
- component (D2) include the following methylol compounds or alkoxymethyl compounds in which a hydrogen atom of a methylol group is substituted with a methyl group or an ethyl group, but are not limited to the following structures.
- the resin composition preferably contains a thermal cross-linking agent containing a structural unit represented by the following general formula (7) (hereinafter sometimes abbreviated as the component (D3)).
- R 38 is a divalent organic group having an alkylene group or alkylene ether group having 1 to 15 carbon atoms, and may be linear, branched, or cyclic.
- R 38 include alkyl groups, cycloalkyl groups, alkoxy groups, alkyl ether groups, alkylsilyl groups, alkoxysilyl groups, aryl groups, aryl ether groups, carboxy groups, carbonyl groups, allyl groups, vinyl groups, complex groups. Examples thereof include a cyclic group and a combination thereof, and may further have a substituent.
- R 39 and R 40 each independently represent a hydrogen atom or a methyl group.
- the component (D3) itself has a flexible alkylene group and a rigid aromatic group, by including the component (D3), the resulting cured film has improved heat resistance while having heat resistance. Low stress is possible. Further, the densification of the cured film suppresses peeling between the cured film and the metal material during the device reliability test.
- Examples of the crosslinking group contained in the component (D3) include, but are not limited to, an acrylic group, a methylol group, an alkoxymethyl group, and an epoxy group.
- an epoxy group is preferable because it can react with the phenolic hydroxyl group of the component (A) to improve the heat resistance of the cured film and can react without dehydration.
- Specific examples of the compound containing the structural unit represented by the general formula (7) include the following, but are not limited to the following structures.
- j is an integer of 1 to 5, and i is 1 to 20. From the standpoint of achieving both heat resistance and improvement in elongation, j is preferably 1 to 2, and i is preferably 3 to 7.
- the above thermal crosslinking agents may be used in combination of two or more.
- the content of the thermal crosslinking agent is preferably 1 part by mass or more and 200 parts by mass or less with respect to 100 parts by mass of the component (A). If the content of the thermal cross-linking agent is 1 part by mass or more and 200 parts by mass or less, the resin composition is excellent in storage stability and storage stability, and can be cured by heat treatment at low temperature, but has chemical resistance. A cured film having a high thickness can be obtained, and further, deterioration of device characteristics after a reliability test of a device to which the cured film is applied can be suppressed.
- the content of the component (D) is preferably 1% by mass or more and 60% by mass or less, and more preferably 5% by mass or more and 50% by mass or less with respect to 100% by mass in total of all the thermal crosslinking agents.
- the content of the component (D2) is preferably 1 to 95% by mass, more preferably 5 to 90% by mass.
- the content of the component (D3) is preferably 1 to 60% by mass, and more preferably 5 to 50% by mass.
- content is 1% by mass or more, chemical resistance is improved even in heat treatment at a low temperature, and high elongation and low stress can be achieved.
- content is 60 mass% or less.
- the resin composition may contain (F) an antioxidant (hereinafter, may be abbreviated as (F) component) as necessary.
- (F) component As a component, although the compound represented by General formula (8) is mentioned, it is not restricted to the following structure.
- R 41 represents a hydrogen atom or an alkyl group having 1 to 15 carbon atoms
- R 42 represents an alkylene group having 2 or more carbon atoms
- R 43 represents a monovalent to tetravalent organic group containing at least one of an alkylene group having 2 or more carbon atoms, an O atom, and an N atom.
- k represents an integer of 1 to 4.
- an alkyl group, a cycloalkyl group, an alkoxy group, an alkyl ether group, an alkylsilyl group, an alkoxysilyl group, an aryl group, an aryl ether group, a carboxy group, a carbonyl group, an allyl group, a vinyl group, a heterocyclic group, —O—, —NH—, —NHNH—, and combinations thereof may be used, and further a substituent may be included.
- alkyl ether groups or —NH— are preferable from the viewpoint of solubility in a developer and metal adhesion, and —NH— is preferred from the viewpoint of interaction with the component (A) and metal adhesion due to metal complex formation. More preferred.
- component suppresses oxidative degradation of aliphatic group and phenolic hydroxyl group of (A) component.
- the rust-proofing action on the metal material suppresses metal oxidation by external moisture, a photosensitizer, and the like, and accompanying peeling between the cured film and the metal material. That is, it is possible to suppress deterioration of device characteristics after the device reliability test.
- Specific examples of the component (F) include the following, but are not limited thereto.
- the amount of component (F) added is preferably 0.1 to 10 parts by weight and more preferably 0.2 to 5 parts by weight with respect to 100 parts by weight of component (A).
- the addition amount is 0.1 parts by mass or more, adhesion to a metal material is improved and peeling is suppressed.
- the addition amount is 10 parts by mass or less.
- the resin composition may contain an adhesion improving agent as necessary.
- the adhesion improver preferably contains a compound represented by the following general formula (9).
- R 44 to R 46 each represent an O atom, an S atom, or an N atom, and at least one of R 44 to R 46 represents an S atom.
- d represents 0 or 1
- e and f each independently represent an integer of 0 to 2.
- R 47 to R 49 each independently represents a hydrogen atom or an organic group having 1 to 20 carbon atoms.
- R 47 to R 49 are hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, alkyl ether group, alkylsilyl group, alkoxysilyl group, aryl group, aryl ether group, carboxy group, carbonyl group, allyl group, vinyl A group, a heterocyclic group, a combination thereof, and the like, and may further have a substituent.
- the compound represented by the general formula (9) By containing the compound represented by the general formula (9), it is possible to remarkably improve the adhesion between the cured film after heat curing and the metal material, particularly copper, and to suppress peeling. This is derived from the fact that the S atom and N atom of the compound represented by the general formula (9) efficiently interact with the metal surface, and has a three-dimensional structure that easily interacts with the metal surface. caused by. Due to these effects, a cured film having excellent adhesion to the metal material can be obtained.
- the addition amount of the compound represented by the general formula (9) is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the component (A). By making the addition amount 0.1 parts by mass or more, the effect of adhesion to the metal material can be sufficiently obtained.
- the amount added is 10 parts by mass or less, in the case where the resin composition is a positive-type photosensitive resin composition, the sensitivity of the resin composition before curing is reduced by interaction with the photosensitive agent. Since it can suppress, it is preferable.
- Examples of the compound represented by the general formula (9) include the following, but are not limited to the following structures.
- the resin composition may contain an adhesion improving agent other than the compound represented by the general formula (9).
- adhesion improvers include vinyltrimethoxysilane, vinyltriethoxysilane, epoxycyclohexylethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxy.
- Silane coupling agents such as silane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, titanium chelating agents, aluminum chelating agents, aromatic amine compounds and alkoxy Examples thereof include compounds obtained by reacting a group-containing silicon compound. Two or more of these may be contained.
- adhesion improving agents adhesion to an underlying substrate such as a silicon wafer, ITO, SiO 2 or silicon nitride can be improved when developing a resin film. Further, resistance to oxygen plasma and UV ozone treatment used for cleaning or the like can be increased.
- the content of the adhesion improving agent in the resin composition is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of component (A). By setting it as such a range, the adhesiveness after image development is high, and the resin composition excellent in the tolerance of oxygen plasma and UV ozone treatment can be provided.
- the content of the other adhesion improving agent is preferably 10 to 500 parts by mass with respect to 100 parts by mass of the compound represented by the general formula (9). By setting it as such a range, the effect of each adhesion improving agent can fully be expressed.
- the resin composition may contain an adhesion improving agent.
- adhesion improving agent include an alkoxysilane-containing aromatic amine compound, an aromatic amide compound, or an aromatic non-containing silane compound. Two or more of these may be contained. By containing these compounds, the adhesiveness between the cured film obtained by curing the resin composition and the substrate can be improved.
- alkoxysilane-containing aromatic amine compound and aromatic amide compound are shown below.
- a compound obtained by reacting an aromatic amine compound and an alkoxy group-containing silicon compound may be used.
- an aromatic amine compound and a group that reacts with an amino group such as an epoxy group or a chloromethyl group may be used.
- Non-aromatic silane compounds include vinyl silane compounds such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltris ( ⁇ -methoxyethoxy) silane, 3-methacryloxypropyltrimethoxysilane, and 3-acryloxypropyl.
- vinyl silane compounds such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltris ( ⁇ -methoxyethoxy) silane, 3-methacryloxypropyltrimethoxysilane, and 3-acryloxypropyl.
- carbon-carbon unsaturated bond-containing silane compounds such as trimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane.
- vinyltrimethoxysilane and vinyltriethoxysilane are preferable.
- the content of the adhesion improver is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of component (A). By setting it as such a range, the adhesiveness of the cured film obtained by hardening
- the resin composition may contain a surfactant for the purpose of improving the wettability with the substrate or improving the film thickness uniformity of the coating film, if necessary.
- a surfactant for the purpose of improving the wettability with the substrate or improving the film thickness uniformity of the coating film, if necessary.
- commercially available compounds can be used. Specifically, as the silicone-based surfactant, SH series, SD series, ST series of Toray Dow Corning Silicone, BYK series of BYK Chemie Japan, Shin-Etsu Silicone's KP Series, Nippon Oil & Fats 'Disform Series, Toshiba Silicone's TSF Series, etc. are listed.
- Fluorosurfactants include Dainippon Ink Industries' “MegaFuck” (registered trademark) series, Sumitomo 3M's Florad series, Asahi Glass's “Surflon” (registered trademark) series, "Asahi Guard” (registered trademark) series, Shin-Akita Kasei's EF series, Omninova Solution's Polyfox series, etc.
- Acrylic and / or methacrylic obtained from the compound, Kyoeisha Chemical Co. Poly flow series, manufactured by Kusumoto Chemicals, Inc. "DISPARON” (registered trademark), but the series and the like, without limitation.
- the content of the surfactant is preferably 0.001 part by mass or more and 1 part by mass or less with respect to 100 parts by mass of the component (A).
- a resin composition can be obtained by mixing and dissolving a polymerizable compound, an adhesion improver, an adhesion improver, a surfactant and the like.
- the dissolution method include heating and stirring. In the case of heating, the heating temperature is preferably set in a range that does not impair the performance of the resin composition, and is usually room temperature to 80 ° C.
- the dissolution order of each component is not particularly limited, and for example, there is a method of sequentially dissolving compounds having low solubility.
- the number of rotations is preferably set within a range that does not impair the performance of the resin composition, and is usually 200 rpm to 2000 rpm. Even in the case of stirring, it may be heated as necessary, and is usually room temperature to 80 ° C.
- components that tend to generate bubbles when stirring and dissolving such as surfactants and some adhesion improvers, by dissolving other components and adding them last, poor dissolution of other components due to the generation of bubbles Can be prevented.
- the viscosity of the resin composition is preferably 2 to 5,000 mPa ⁇ s.
- the solid content concentration so that the viscosity is 2 mPa ⁇ s or more, it becomes easy to obtain a desired film thickness.
- the viscosity is 5,000 mPa ⁇ s or less, it becomes easy to obtain a highly uniform coating film.
- a resin composition having such a viscosity can be easily obtained, for example, by setting the solid content concentration to 5 to 60% by mass.
- the obtained resin composition is preferably filtered using a filtration filter to remove dust and particles.
- a filtration filter to remove dust and particles.
- the filter pore diameter include, but are not limited to, 0.5 ⁇ m, 0.2 ⁇ m, 0.1 ⁇ m, 0.05 ⁇ m, and 0.02 ⁇ m.
- the material for the filter include polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE), and polyethylene and nylon are preferable.
- the resin film is defined as a film obtained by applying a resin composition to the surface of a substrate and drying it.
- the cured film is defined as a film obtained by curing a resin film.
- the method for producing a cured film of the present invention includes a step of applying the resin composition on a substrate and drying to form a resin film, an exposure step of exposing the resin film if photosensitive, and an exposed resin. It is a method for producing a cured film, which includes a developing step for developing the film and a heat treatment step for heat-treating the developed resin film.
- the resin composition of the present invention is applied to a substrate to obtain a coating film of the resin composition.
- the substrate include silicon wafers, ceramics, gallium arsenide, organic circuit substrates, inorganic circuit substrates, and substrates in which circuit constituent materials are arranged, but are not limited thereto.
- the coating method include spin coating, slit coating, dip coating, spray coating, and printing.
- the coating film thickness varies depending on the coating method, the solid content concentration of the composition, the viscosity, and the like, but is usually applied so that the film thickness after drying is 0.1 to 150 ⁇ m.
- the substrate on which the resin composition is applied may be pretreated with the above-described adhesion improving agent in advance.
- a method of treating the substrate surface by a method such as spin coating, slit die coating, bar coating, dip coating, spray coating, or steam treatment. After the substrate surface is treated, a reduced-pressure drying treatment may be performed as necessary. Further, the reaction between the base material and the adhesion improving agent may be advanced by a heat treatment at 50 ° C. to 280 ° C.
- the coating film of the resin composition is dried to obtain a resin film. Drying is preferably performed using an oven, a hot plate, infrared rays, or the like in the range of 50 ° C. to 140 ° C. for 1 minute to several hours.
- actinic radiation is irradiated through a mask having a desired pattern on the photosensitive resin film.
- Actinic rays used for exposure include ultraviolet rays, visible rays, electron beams, X-rays, etc.
- Developers include tetramethylammonium, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl
- An aqueous solution of a compound exhibiting alkalinity such as methacrylate, cyclohexylamine, ethylenediamine, hexamethylenediamine and the like is preferable.
- polar solutions such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide; methanol, ethanol, One or more alcohols such as isopropanol; esters such as ethyl lactate and propylene glycol monomethyl ether acetate; ketones such as cyclopentanone, cyclohexanone, isobutyl ketone and methyl isobutyl ketone may be added. After development, it is common to rinse with water.
- alcohols such as ethanol and isopropyl alcohol, and esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to water for rinsing treatment.
- the resin film thus obtained is heated to cause the thermal crosslinking reaction to proceed to obtain the cured film of the present invention.
- the cured film is improved in heat resistance and chemical resistance by crosslinking.
- This heat treatment may be performed while raising the temperature stepwise, or may be performed while raising the temperature continuously.
- the heat treatment is preferably performed for 5 minutes to 5 hours. As an example, a heat treatment is performed at 110 ° C. for 30 minutes, and then a heat treatment is further performed at 170 ° C. for 60 minutes.
- the heat treatment condition is preferably 140 ° C. or higher and 280 ° C. or lower.
- the heat treatment conditions are preferably 140 ° C. or higher and more preferably 160 ° C. or higher in order to advance the thermal crosslinking reaction.
- the present invention aims to provide a cured film that is particularly excellent in low-temperature curability, and suppresses malfunction caused by the thermal history of the semiconductor device described later, and improves the yield.
- a cured film that is particularly excellent in low-temperature curability, and suppresses malfunction caused by the thermal history of the semiconductor device described later, and improves the yield.
- 250 degrees C or less is more preferable, and 230 degrees C or less is further more preferable.
- the cured film of the present invention can be used for electronic parts such as semiconductor devices. That is, the semiconductor device of the present invention is a semiconductor device having a metal wiring and an insulating film, and has the cured film of the present invention as an insulating film.
- the semiconductor device generally refers to a device including a semiconductor element and an integrated circuit in which the semiconductor element is integrated as a component.
- the semiconductor device in the present invention includes not only a device including a semiconductor element but also a component for a semiconductor device such as a wiring board.
- the cured film of the present invention is suitably used for applications such as a semiconductor passivation film, a protective film for semiconductor elements, and an interlayer insulating film for multilayer wiring for high-density mounting.
- the cured film of the present invention is suitable for a surface protective film of MRAM.
- MRAM Polymer Ferroelectric RAM: PFRAM
- phase change memory Phase Change RAM: PCRAM
- OUM Ovonic Unified Memory
- a display device including a first electrode formed on a substrate and a second electrode provided to face the first electrode, specifically, for example, an LCD, an ECD, an ELD, an organic electroluminescent element It can also be used for an insulating layer of the display device (organic electroluminescence device) used.
- the cured film of the present invention is used as a protective film for such an electrode or wiring, it is particularly preferably used because it has high resistance to these chemicals.
- the copper wiring may be oxidized in the manufacturing process. Even in such a case, the cured film of the present invention can be preferably used.
- FIG. 1 is an enlarged cross-sectional view of a pad portion of a semiconductor device having bumps.
- Al input / output aluminum
- passivation film 3 passivation film 3
- insulating film 4 made of a cured product of the resin composition of the present invention is formed thereon, and a metal film 5 is formed so as to be electrically connected to the Al pad 2.
- Cr Cr, Ti or the like is preferably used.
- a metal wiring 6 is provided on the metal film 5.
- As a material of the metal wiring 6, Ag, Cu or the like is preferably used. In recent years, as described above, copper wiring is particularly preferably used.
- the metal wiring 6 is preferably formed on the metal film 5 using a plating method.
- An insulating film 7 made of a cured product of the resin composition of the present invention is formed on the insulating film 4 and the metal film 5. The insulating film 7 needs to be opened by a photolithography process in the pad portion where the scribe line 9 and the solder bump 10 are to be installed. After the barrier metal 8 is formed on the pad portion, the solder bump 10 is formed.
- the resin composition of the present invention is applied on the silicon wafer 1 on which the Al pad 2 and the passivation film 3 are formed, and after forming a pattern using a photolithography process, the insulating film 4 is cured. Form.
- a metal film 5 is formed by a sputtering method.
- a metal wiring 6 is formed on the metal film 5 by using a plating method.
- the resin composition of the present invention is applied thereon, and after forming a pattern using a photolithography process, it is cured to form an insulation having a shape as shown in FIG. 2d.
- a film 7 is formed.
- an opening is formed in the scribe line 9 in the insulating film 7.
- a wiring (so-called rewiring) may be further formed on the insulating film 7.
- the formed insulating film will come into contact with various chemicals multiple times, but the insulating film made of a cured product of the resin composition of the present invention is excellent in adhesion and chemical resistance.
- a good multilayer wiring structure can be formed. There is no upper limit to the number of layers in the multilayer wiring structure, but 10 or fewer layers are often used.
- a barrier metal 8 and a solder bump 10 are formed. Then, the wafer is diced along the scribe line 9 and cut into chips.
- the insulating film 7 has no opening in the scribe line 9 or a residue remains, cracks or the like occur during dicing, which affects the reliability of the chip. For this reason, it is very preferable to provide pattern processing excellent in thick film processing in order to obtain high reliability of the semiconductor device.
- the resin composition of the present invention is also suitably used for a fan-out wafer level package (fan-out WLP) or a fan-out panel level package (fan-out PLP).
- Fan-out WLP is a technique for manufacturing a large number of semiconductor packages on a wafer at once.
- Fan-out PLP is a technique for manufacturing a large number of semiconductor packages on a rectangular substrate, that is, a panel, in a part or all of the processes.
- FIG. 3 is a manufacturing process cross-sectional view of an example of a semiconductor device having the cured film of the present invention. Specifically, it is an enlarged sectional view of a semiconductor package called Chip-first fan-out WLP or Chip-first fan-out PLP.
- the silicon wafer on which the Al pad 2 and the passivation film 3 are formed is diced, cut into semiconductor chips 1 ′, and sealed with a sealing resin 11.
- the insulating film 4 is formed by applying the resin composition of the present invention over the sealing resin 11 and the semiconductor chip 1 ′, providing an opening by pattern formation using a photolithography process, and then curing.
- the A metal film 5 made of Cr, Ti or the like and a metal wiring 6 made of Ag, Cu or the like are further formed on the insulating film 4.
- the metal film 5 and the metal wiring 6 are electrically connected to the Al pad 2 provided on the semiconductor chip 1 ′ in the opening provided in the insulating film 4.
- An insulating film 7 is further formed thereon.
- the resin composition of the present invention is also preferably used for forming the insulating film 7.
- a barrier metal 8 and a solder bump 10 are formed in the opening provided in the insulating film 7.
- the barrier metal 8 and the solder bump 10 are electrically connected to the metal wiring 6.
- the Chip-first fan-out WLP or the Chip-first fan-out PLP is provided with an extended portion using a sealing resin such as an epoxy resin around the semiconductor chip, and rewiring is performed from the electrode on the semiconductor chip to the extended portion.
- a sealing resin such as an epoxy resin around the semiconductor chip
- This is a semiconductor package that secures the necessary number of terminals by mounting solder balls on the extended part.
- the wiring is installed so as to straddle the boundary formed by the main surface of the semiconductor chip and the main surface of the sealing resin.
- the insulating film 7 is disposed as an interlayer insulating film on a base material composed of two or more materials such as a semiconductor chip and a sealing resin, and a metal wiring (rewiring) 6 is disposed on the interlayer insulating film. Is done.
- the cured film of the present invention is suitable for fine rewiring because the metal film has high metal adhesion to a wiring having a width of metal wiring and a distance between adjacent wirings of 5 ⁇ m or less.
- the width of the metal wiring and the distance between adjacent wirings of 5 ⁇ m or less means that the width of the metal wiring is 5 ⁇ m or less and the distance between the adjacent wirings is also 5 ⁇ m or less.
- the Chip-first fan-out WLP or the Chip-first fan-out PLP having such a fine structure has a multi-layered structure in which a plurality of redistribution layers are laminated, and among the adjacent redistribution layers, a semiconductor chip
- the width of the metal wiring in the rewiring layer closer to the distance and the distance between adjacent wirings are the same or narrower than the width of the metal wiring in the rewiring layer farther from the semiconductor chip and the distance between adjacent wirings. It is preferable.
- the rewiring layer refers to a layer composed of a pair of rewirings and an interlayer insulating film formed thereon in a multilayer wiring structure in which a plurality of rewirings are separated by a plurality of interlayer insulating films. .
- the rewiring layer is composed of only one layer.
- the width of the metal wiring in the rewiring layer and the interval between adjacent wirings are the same or narrower means that the width of the metal wiring in the rewiring layer closer to the semiconductor chip is smaller than that of the rewiring layer far from the semiconductor chip.
- the spacing between adjacent wirings in the rewiring layer that is the same or narrower and closer to the semiconductor chip is compared to the spacing between adjacent wirings in the rewiring layer farther from the semiconductor chip. Mean the same or narrow.
- the thickness of the interlayer insulating film of the rewiring layer closer to the semiconductor chip among the adjacent rewiring layers is compared with the thickness of the interlayer insulating film of the rewiring layer farther from the semiconductor chip.
- each rewiring layer constituting the multilayer wiring structure is gradually made finer pitch from the far side from the semiconductor chip to the near side to the semiconductor chip.
- the in-plane uniformity of the interlayer insulating film in each rewiring layer is important.
- a plurality of rewiring layers including metal wiring (rewiring) and an interlayer insulating film are stacked on a support substrate on which a temporary sticking material is disposed, and further a semiconductor chip is formed thereon.
- a type created in a process called RDL (Redistribution Layer) -first which separates the semiconductor package by separating the support substrate and the redistribution layer after forming a semiconductor package by arranging a sealing resin and There are semiconductor packaging. That is, the support substrate is used only in the manufacturing process and is not included in the completed semiconductor package.
- the insulating film preferably has low stress.
- a panel with a large area is used aiming at the cost advantage of mass production, so reduction of warpage due to film shrinkage of the interlayer insulating film and improvement of in-plane uniformity of film thickness are problems. ing.
- a barrier metal such as Ti is formed on a support substrate 20 such as a glass substrate or a silicon wafer by a sputtering method, and a Cu seed (seed layer) is formed thereon by a sputtering method.
- An electrode pad 21 is formed.
- the resin composition of the present invention is applied to the entire surface of the support substrate 20 on which the electrode pad 21 is formed, and after forming a pattern using a photolithography process, the insulating film 22 is cured by curing. Form.
- a seed layer is formed again by a sputtering method, and a metal wiring 23 (rewiring) made of Cu is formed by a plating method. Thereafter, the steps of FIGS. 4b and 4c are repeated to form a multilayer wiring structure as shown in FIG. 4d.
- the resin composition of the present invention is applied again, and after forming a pattern using a photolithography process, the insulating film 22 is formed by curing, and then metal wiring is formed in the opening of the insulating film 22.
- a Cu post 24 is formed on 23 using a plating method.
- the pitch of the Cu posts 24 and the conduction portion pitch of the semiconductor chip 26 are made equal.
- the pitch of the conductive portions of the semiconductor chip 26 is finer than the pitch of the electrode pads 21.
- each rewiring layer constituting the multilayer wiring structure is transferred from the electrode pads 21 to the Cu posts 24.
- the wiring is multilayered while gradually becoming fine pitch.
- the thickness of the adjacent interlayer insulating film 22 is the same or thinner as it approaches the semiconductor chip.
- the semiconductor chip 26 is connected to the Cu post 24 via the solder bump 25.
- the electrode pad 21 and the semiconductor chip 26 are electrically connected via the metal wiring 23 and the solder bump 25.
- the semiconductor chip 26 is sealed with a sealing resin to form a semiconductor package, and then the support substrate and the redistribution layer are separated to separate the semiconductor package. In this way, a semiconductor device having a multilayer wiring structure using the RDL first process can be obtained.
- wiring is installed so as to straddle the boundary line between the main surface of the semiconductor chip and the main surface of the printed circuit board.
- an interlayer insulating film is formed on a base material composed of two or more materials, and wiring (rewiring) is formed on the interlayer insulating film. Since the cured film formed by curing the resin composition of the present invention has high adhesion to a semiconductor chip provided with metal wiring and also has high adhesion to an epoxy resin or the like, it has two or more kinds. It is suitably used as an interlayer insulating film provided on a substrate composed of the above material.
- FIG. 5 is a cross-sectional view of the coil component of the inductor device showing the embodiment of the present invention.
- an insulating film 13 is formed on the entire surface of the substrate 12, and an insulating film 14 having an opening formed thereon is formed thereon.
- the resin composition of the present invention may be used for either the insulating film 13 or the insulating film 14.
- a metal film 15 made of Cr, Ti or the like is formed in the opening of the insulating film 14, and a metal wiring 16 made of Ag, Cu or the like is formed thereon using a plating method.
- the metal wiring 16 is formed in a spiral shape.
- the metal wiring 16 provided in the uppermost layer is connected to the electrode 18 by a metal wiring 17 made of Ag, Cu or the like, and is sealed with a sealing resin 19.
- the resin composition of the present invention is also suitably used for organic EL display devices.
- the organic EL display device has a driving circuit, a planarizing layer, a first electrode, an insulating layer, a light emitting layer, and a second electrode on a substrate, and the planarizing layer and / or the insulating layer is made of the cured film of the present invention.
- Organic EL light-emitting materials are susceptible to deterioration due to moisture and may adversely affect the area ratio of the light-emitting portion relative to the area of the light-emitting pixels, but the cured film of the present invention has a low water absorption rate, so stable driving and light emission Characteristics are obtained.
- an active matrix type organic EL display device on a substrate made of glass, various plastics, etc., it has a TFT and a wiring located on a side portion of the TFT and connected to the TFT.
- a planarization layer is provided so as to cover the unevenness, and a display element is further provided on the planarization layer. The display element and the wiring are connected through a contact hole formed in the planarization layer.
- FIG. 6 shows a cross-sectional view of an example of a TFT substrate.
- bottom gate type or top gate type TFTs (thin film transistors) 27 are provided in a matrix, and a TFT insulating layer 29 is formed in a state of covering the TFTs 27.
- a wiring 28 connected to the TFT 27 is provided on the TFT insulating layer 29.
- a planarizing layer 30 is provided on the TFT insulating layer 29 in a state where the wiring 28 is embedded.
- a contact hole 33 reaching the wiring 28 is provided in the planarization layer 30.
- a transparent electrode 31 made of ITO or the like is formed on the planarizing layer 30 while being connected to the wiring 28 through the contact hole 33.
- the transparent electrode 31 serves as an electrode of a display element (for example, an organic EL element).
- An insulating layer 34 is formed so as to cover the periphery of the transparent electrode 31.
- the organic EL element may be a top emission type that emits emitted light from the side opposite to the substrate 32 or a bottom emission type that extracts light from the substrate 32 side.
- an active matrix type organic EL display device in which the TFT 27 for driving the organic EL element is connected to each organic EL element is obtained.
- the TFT insulating layer 29, the planarizing layer 30, and / or the insulating layer 34 are formed by a step of forming a resin film made of the resin composition of the present invention, a step of exposing the resin film, a step of developing the exposed resin film, and It can form by the process of heat-processing the developed resin film.
- An organic EL display device can be obtained from the manufacturing method having these steps.
- in-plane uniformity of the film thickness is 0 ⁇ m or more and less than 0.35 ⁇ m as very good, 3 is 0.35 ⁇ m or more and less than 0.6 ⁇ m is good, 2 is 0.6 ⁇ m or more as bad, It was evaluated.
- the obtained pre-baked film 10 mg was adsorbed and trapped by the purge and trap method. Specifically, the collected prebaked film was heated at 250 ° C. for 40 minutes using helium as a purge gas, and the desorbed components were collected in an adsorption tube.
- the collected components are thermally desorbed using a thermal desorption apparatus at a primary desorption condition of 260 ° C. for 15 minutes, a secondary adsorption condition of ⁇ 27 ° C. and a secondary desorption condition of 320 ° C. for 5 minutes, and then a GC-MS apparatus GC-MS analysis was performed using 7890 / 5975C (manufactured by Agilent) under conditions of column temperature: 40 to 300 ° C., carrier gas: helium (1.5 mL / min), scan range: m / Z 29 to 600. .
- the amount of gas generated was calculated by preparing a calibration curve by GC-MS analysis under the same conditions as above for each component (E).
- the remaining amount of the component (E) was evaluated as 2 as good if it was 0.001% by mass or more and 30% by mass or less, and as 1 if it was less than 0.001% by mass or exceeded 30% by mass. .
- a varnish was prepared and spin-coated on an 8-inch silicon wafer using a coating and developing apparatus ACT-8 (manufactured by Tokyo Electron Ltd.) so that the film thickness after pre-baking was 11 ⁇ m.
- Application and pre-baking were performed by a coating method to prepare a pre-baked film. Or it applied by the slit coat method using the slit coater, dried under reduced pressure, and prebaked, and produced the prebaked film
- Pre-baking was performed by heating at 120 ° C. for 3 minutes. Thereafter, the prebaked film was heated to 170 ° C.
- the obtained pre-baked film was used with a 2.38 mass% tetramethylammonium (TMAH) aqueous solution (manufactured by Tama Chemical Industries) under the conditions of 25 seconds ⁇ 2 times to 60 seconds ⁇ 2 times so that the film thickness became 11 ⁇ m. And then rinsed with pure water. Then, using an inert oven CLH-21CD-S, the temperature was raised to 170 ° C. at 4.0 ° C./min with an oxygen concentration of 20 ppm or less under a nitrogen stream, and heat treatment was performed at 170 ° C. for 1 hour to cure the prebaked film. Thus, a cured film was obtained. When the temperature reached 50 ° C. or lower, the silicon wafer was taken out.
- TMAH tetramethylammonium
- the film thickness of the pre-baked film after pre-baking and development, and the film thickness of the cured film after the heat treatment were measured using a light interference type film thickness measuring device Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd.
- the refractive index was measured as 1.629. 10 mg of the obtained cured film was adsorbed and trapped by the purge and trap method. Specifically, the collected cured film was heated at 250 ° C. for 40 minutes using helium as a purge gas, and the desorbed components were collected in an adsorption tube.
- the collected components are thermally desorbed using a thermal desorption apparatus at a primary desorption condition of 260 ° C. for 15 minutes, a secondary adsorption condition of ⁇ 27 ° C. and a secondary desorption condition of 320 ° C. for 5 minutes, and then a GC-MS apparatus GC-MS analysis was performed using 7890 / 5975C (manufactured by Agilent) under conditions of column temperature: 40 to 300 ° C., carrier gas: helium (1.5 mL / min), scan range: m / Z 29 to 600. .
- the amount of gas generated was calculated by preparing a calibration curve by GC-MS analysis under the same conditions as above for each component (E).
- the varnish is applied and prebaked on the evaluation substrate by spin coating using a coating / developing apparatus ACT-8 (manufactured by Tokyo Electron Ltd.) so that the film thickness after prebaking at 120 ° C. for 3 minutes becomes 11 ⁇ m.
- a pre-baked film was prepared. Or it applied by the slit coat method using the slit coater, dried under reduced pressure, and prebaked, and produced the prebaked film
- the evaluation substrate (hereinafter referred to as a sample) was taken out.
- the sample was put into a 175 ° C. constant temperature bath and treated for 200 hours. After that, the sample was taken out, and the sample was cut using a scanning electron microscope FEI Helios 650 (manufactured by FEI Co., Ltd.) attached to the focused ion beam processing apparatus and the magnification was 40,000 times in order to observe the peeling on the copper wiring. The cross section was observed. As an evaluation method, the degree of peeling of the side surface of the copper wiring was observed, 3 being exfoliated at 0% or more and less than 25% was regarded as very good 3; Was rated as 1 as defective.
- a varnish is prepared and applied on a 8-inch silicon wafer by spin coating using a coating and developing apparatus ACT-8 (manufactured by Tokyo Electron Co., Ltd.) so that the film thickness after development is 11 ⁇ m.
- a membrane was prepared. Or it applied by the slit coat method using the slit coater, dried under reduced pressure, and prebaked, and produced the prebaked film
- Ghi The resulting prebaked film line mask aligner (Union Optical Co., PEM-6M) was exposed at 20 mJ / cm 2 steps at each 0 ⁇ 1500mJ / cm 2 exposure amount using the.
- Line & space (L & S) patterns used for exposure are 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 30, 50, and 100 ⁇ m.
- development was performed using a 2.38 mass% tetramethylammonium (TMAH) aqueous solution (manufactured by Tama Chemical Industry) under conditions of 25 seconds ⁇ 2 times to 60 seconds ⁇ 2 times so that the film thickness becomes 11 ⁇ m.
- TMAH tetramethylammonium
- rinsing with pure water gave a relief pattern.
- the film thickness of the pre-baked film after pre-baking and development was measured using a light interference type film thickness measuring apparatus Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd., with a refractive index of 1.629.
- the minimum exposure amount at which a 20 ⁇ m line and space (L / S) pattern was formed in a one-to-one relationship was defined as sensitivity.
- the sensitivity was evaluated as 1, 2,600mJ / cm 2 or more things as bad those less than 500 mJ / cm 2 to 3,500mJ / cm 2 or more 600 mJ / cm of less than 2 as a good as very good .
- the varnish was stored in an environment of a temperature of 23 ° C. and a humidity of 50%, evaluated after 14 days under the same conditions, and the dimension of the space in the obtained 20 ⁇ m line & space pattern was measured.
- the change in pattern dimension was evaluated as 1 when the change in pattern size was 0 ⁇ m or more and less than 1 ⁇ m, 3 as excellent, 1 2 or more and less than 2 ⁇ m as good, and 2 or 2 ⁇ m or more as bad.
- Placement stability test Coating development apparatus ACT-8 (manufactured by Tokyo Electron Ltd.) so that the film thickness after pre-baking the varnish on an 8-inch silicon wafer is 12.5 ⁇ m and the film thickness after development is 11 ⁇ m. ) was applied by spin coating and pre-baked and pre-baked to prepare a pre-baked film, or was applied by slit coating using a slit coater, dried under reduced pressure and pre-baked to prepare a pre-baked film. All pre-baking was performed at 120 ° C. for 3 minutes.
- the film thickness of the pre-baked film after pre-baking and development was measured using a light interference type film thickness measuring apparatus Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd., with a refractive index of 1.629.
- the sensitivity was defined as the minimum exposure amount at which a 20 ⁇ m line & space (L / S) pattern was formed in a one-to-one relationship after exposure and development.
- a pre-baked film was prepared on an 8-inch silicon wafer in the same manner as described above, and after the pre-baked film was prepared or stored for 8 hours after exposure in an environment of temperature 23 ° C. and humidity 50%. Evaluation was performed under the same conditions, and the dimension of the space in the obtained 20 ⁇ m line & space pattern was measured, and the change in dimension was measured before and after storage. In this case, after the pre-baked film is produced, the pattern size change amount is 0 ⁇ m or more and less than 0.5 ⁇ m as very good, 3 0.5 ⁇ m or more and less than 1 ⁇ m as good, and 2 or 1 ⁇ m or more as bad. 1 was evaluated.
- the change in pattern dimension was evaluated as 1 when the change was 0 ⁇ m or more and less than 1 ⁇ m, and 3 when the change was 1 ⁇ m or more and less than 2 ⁇ m, 2 when the change was 2 ⁇ m or more.
- (B) component (C1) component, (C2) component, thermal crosslinking agent component, (E) component and other components used in Examples and Comparative Examples are shown below.
- (B) component (C1) component, (C2) component, thermal crosslinking agent component, (E) component and other components used in Examples and Comparative Examples are shown below.
- Radical polymerizable compound dipentaerythritol hexaacrylate (DPHA).
- Examples 1 to 7, Comparative Examples 1 to 4 A varnish was prepared by adding the component (C), the thermal crosslinking agent, the component (E) and other components in 10 parts by mass shown in Table 1 to 10 g of the resin (A-1) obtained in Synthesis Example 2. These characteristics were measured by the above evaluation method. The measurement results are shown in Table 2.
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Abstract
Description
(1)(A)ポリイミド、ポリイミド前駆体、ポリベンゾオキサゾール、ポリベンゾオキサゾール前駆体、その他のポリアミド、およびこれらの共重合体から選択される1種類以上の樹脂、(D)エポキシ基数が3以上の熱架橋剤、および(E)分子量が60以上1000以下の第3級アミド構造を有する化合物を含む、樹脂組成物。
(2)上記の樹脂組成物を硬化した硬化膜。
(3)上記の樹脂組成物を基板上に塗布し、乾燥して樹脂膜を形成する工程、樹脂膜を露光する露光工程、露光された樹脂膜を現像する現像工程、および現像された樹脂膜を加熱処理する加熱処理工程を含む硬化膜の製造方法。
(4)金属配線および絶縁膜を有する半導体装置であって、上記の硬化膜を絶縁膜として有する半導体装置。
(5)さらに半導体チップを含み、金属配線が該半導体チップと電気的に接続されている(4)に記載の半導体装置。
(6)前記半導体チップが封止樹脂に封止されており、前記半導体チップおよび前記封止樹脂の上に前記絶縁膜が層間絶縁膜として配置され、該層間絶縁膜の上に前記金属配線が配置された(5)に記載の半導体装置。
(7)仮貼り材料が配置された支持基板上に、金属配線および上記の硬化膜からなる再配線層を複数積層する工程と、
その上に半導体チップと封止樹脂を配置して半導体パッケージを作成する工程と、
その後、該支持基板と該半導体パッケージを剥離する工程を含む、半導体装置の製造方法。
一般式(7)で表される構造単位を含む化合物は、具体例としては以下のものが挙げられるが、下記構造に限らない。
(1)面内均一性
ワニス(樹脂組成物)を作製して8インチのシリコンウエハ上に、プリベーク後の膜厚が12.5μmとなるよう、塗布現像装置ACT-8(東京エレクトロン(株)製)を用いてスピンコート法で塗布およびプリベークを行い、プリベーク膜を作製した。もしくはスリットコーターを用いてスリットコート法で塗布、減圧乾燥およびプリベークを行い、プリベーク膜を作製した。プリベークは、120℃で3分間加熱して行った。その後、8インチウエハを中央から左右2cm間隔で9点の膜厚を測定し、膜厚の最小値と最大値の差を膜厚の面内均一性とした。膜厚の面内均一性の値が0μm以上0.35μm未満のものを極めて良好として3、0.35μm以上0.6μm未満のものを良好として2、0.6μm以上のものを不良として1、と評価した。
ワニスを8インチシリコンウエハ上にプリベーク後の膜厚が13μmとなるよう、塗布現像装置ACT-8(東京エレクトロン(株)製)を用いてスピンコート法で塗布およびプリベークを行い、プリベーク膜を作製した。もしくはスリットコーターを用いてスリットコート法で塗布、減圧乾燥およびプリベークを行い、プリベーク膜を作製した。プリベークは、120℃で3分間加熱して行った。なお、プリベーク後の膜厚は、大日本スクリーン製造(株)製光干渉式膜厚測定装置ラムダエースSTM-602を使用し、屈折率を1.629として測定した。得られたプリベーク膜のうち10mgをパージ・アンド・トラップ法にて吸着捕捉した。具体的には、採取したプリベーク膜を、パージガスとしてヘリウムを用いて250℃で40分間加熱し、脱離した成分を吸着管に捕集した。
ワニスを作製し、粘度計にて粘度を測定した。その後、該ワニスを温度23℃、湿度50%の環境下にて保管し、14日後に同条件で評価を行い、粘度の変化量を測定した。粘度の変化量が0%以上10%未満のものを良好として2、10%以上のものを不良として1、と評価した。
ワニスを作製して8インチのシリコンウエハ上に、プリベーク後の膜厚が11μmとなるよう、塗布現像装置ACT-8(東京エレクトロン(株)製)を用いてスピンコート法で塗布およびプリベークを行い、プリベーク膜を作製した。もしくはスリットコーターを用いてスリットコート法で塗布、減圧乾燥およびプリベークを行い、プリベーク膜を作製した。プリベークは、120℃で3分間加熱して行った。その後、プリベーク膜をイナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、窒素気流下において酸素濃度20ppm以下で4.0℃/分で170℃まで昇温し、170℃で1時間加熱処理を行ない、プリベーク膜を硬化させて硬化膜を得た。温度が50℃以下になったところでシリコンウエハを取り出し、得られた硬化膜を有機薬液(ジメチルスルホキシド:25%水酸化テトラメチルアンモニウム水溶液=92:2)に65℃で30分間浸漬させ、剥がれや溶出の有無を観察した。
ワニスを作製して8インチのシリコンウエハ上に、現像後の膜厚が11μmとなるよう、塗布現像装置ACT-8(東京エレクトロン(株)製)を用いてスピンコート法で塗布およびプリベークを行い、プリベーク膜を作製した。もしくはスリットコーターを用いてスリットコート法で塗布、減圧乾燥およびプリベークを行い、プリベーク膜を作製した。プリベークはいずれも120℃で3分間行った。得られたプリベーク膜を2.38質量%のテトラメチルアンモニウム(TMAH)水溶液(多摩化学工業製)を用いて、膜厚が11μmとなるよう、25秒×2回~60秒×2回の条件で現像し、次いで純水でリンスした。その後イナートオーブンCLH-21CD-Sを用いて、窒素気流下において酸素濃度20ppm以下で4.0℃/分で170℃まで昇温し、170℃で1時間加熱処理を行ない、プリベーク膜を硬化させて硬化膜を得た。温度が50℃以下になったところでシリコンウエハを取り出した。なお、プリベーク後および現像後のプリベーク膜の膜厚、および加熱処理後の硬化膜の膜厚は、大日本スクリーン製造(株)製光干渉式膜厚測定装置ラムダエースSTM-602を使用し、屈折率を1.629として測定した。得られた硬化膜のうち10mgをパージ・アンド・トラップ法にて吸着捕捉した。具体的には、採取した硬化膜を、パージガスとしてヘリウムを用いて250℃で40分間加熱し、脱離した成分を吸着管に捕集した。
銅配線での剥離評価を行うにあたり、以下の評価基板を準備した。8インチシリコンウエハ上に、厚み5μm、直径90μmの円柱型銅配線を、銅配線の中心間距離が150μmとなるように等間隔に作成した。これを評価基板として使用した。
(6)面内均一性
上記「(1)面内均一性」と同様に評価した。
上記「(2)樹脂膜中(E)成分残存量評価」と同様に評価した。
ワニスを作製して8インチシリコンウエハ上に現像後の膜厚が11μmとなるよう、塗布現像装置ACT-8(東京エレクトロン(株)製)を用いてスピンコート法で塗布およびプリベークを行い、プリベーク膜を作製した。もしくはスリットコーターを用いてスリットコート法で塗布、減圧乾燥およびプリベークを行い、プリベーク膜を作製した。プリベークはいずれも120℃で3分間行った。得られたプリベーク膜をghi線マスクアライナー(ユニオン光学(株)製、PEM-6M)を用いてそれぞれ0~1500mJ/cm2の露光量にて20mJ/cm2ステップで露光した。露光に用いたライン&スペース(L&S)パターンは1、2、3、4、5、6、7、8、9、10、15、20、30、50、100μmである。露光後、2.38質量%のテトラメチルアンモニウム(TMAH)水溶液(多摩化学工業製)を用いて、膜厚が11μmとなるよう、25秒×2回~60秒×2回の条件で現像し、次いで純水でリンスし、レリーフパターンを得た。なお、プリベーク後および現像後のプリベーク膜の膜厚は、大日本スクリーン製造(株)製光干渉式膜厚測定装置ラムダエースSTM-602を使用し、屈折率を1.629として測定した。
ワニスを8インチシリコンウエハ上にプリベーク後の膜厚が12.5μm、現像後の膜厚が11μmとなるよう、塗布現像装置ACT-8(東京エレクトロン(株)製)を用いてスピンコート法で塗布およびプリベークプリベークを行い、プリベーク膜を作製したもしくはスリットコーターを用いてスリットコート法で塗布、減圧乾燥およびプリベークを行い、プリベーク膜を作製した。プリベークはいずれも120℃で3分間行った。得られたプリベーク膜をghi線マスクアライナー(ユニオン光学(株)製、PEM-6M)を用いてそれぞれ0~1500mJ/cm2の露光量にて20mJ/cm2ステップで露光した。露光に用いたライン&スペース(L&S)パターンは1、2、3、4、5、6、7、8、9、10、15、20、30、50、100μmである。露光後、2.38質量%のテトラメチルアンモニウム(TMAH)水溶液(多摩化学工業製)を用いて、膜厚が11μmとなるよう、25秒×2回~60秒×2回の条件で現像し、次いで純水でリンスし、レリーフパターンを得た。なお、プリベーク後および現像後のプリベーク膜の膜厚は、大日本スクリーン製造(株)製光干渉式膜厚測定装置ラムダエースSTM-602を使用し、屈折率を1.629として測定した。
上記「(4)耐薬品性の評価」と同様に評価した。
上記「(5-1)信頼性試験(硬化膜中(E)成分残存量評価)」と同様に評価した。
上記「(5-2)信頼性試験(高温保存性試験(High Temperature Storage、HTS)後の銅配線での剥離評価)」と同様に評価した。
2,2-ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン(セントラル硝子(株)製、以下、BAHFとする)18.3g(0.05モル)をアセトン100mLおよびプロピレンオキシド(東京化成(株)製)17.4g(0.3モル)に溶解させ、-15℃に冷却した。ここに3-ニトロベンゾイルクロリド(東京化成(株)製)20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、-15℃で4時間撹拌し、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、BAHF27.47g、(0.075モル)をNMP257gに溶解させた。ここに、1,1’-(4,4’-オキシベンゾイル)ジイミダゾール(以降PBOMと呼ぶ)17.20g(0.048モル)をNMP20gとともに加えて、85℃で3時間反応させた。続いて、プロピレンオキシドおよびテトラメチレンエーテルグリコール構造を含むジアミン(RT-1000、HUNTSMAN(株)製))20.00g(0.020モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(以下、SiDAと呼ぶ)1.24g(0.005モル)、PBOM14.33g(0.044モル)をNMP50gとともに加えて、85℃で1時間反応させた。さらに、末端封止剤として、5-ノルボルネン-2,3-ジカルボン酸無水物3.94g(0.024モル)をNMP10gとともに加えて、85℃で30分反応させた。反応終了後、室温まで冷却し、酢酸52.82g(0.50モル)をNMP87gとともに加えて、室温で1時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリベンゾオキサゾール前駆体(A-1)の粉末を得た。
前記合成例2に従って、BAHF(32.96g、0.090モル)、PBOM(29.38g、0.082モル)、RT-1000(10.00g、0.010モル)、SiDA(1.49g、0.0060モル)、5-ノルボルネン-2,3-ジカルボン酸無水物(5.91g、0.036モル)、HFHA(0.60g、0.0010モル)、ODPA(2.17g、0.0070モル)、酢酸(49.22g、0.82モル)およびNMP360gを用いて同様に行い、ポリベンゾオキサゾール前駆体(A-2)の粉末を得た。
乾燥窒素気流下、合成例1で得られたヒドロキシル基含有ジアミン57.4g(0.095モル)およびSiDA1.24g(0.005モル)をNMP200gに溶解した。ここに4,4’-オキシジフタル酸無水物(以下、ODPAと呼ぶ)31.0g(0.10モル)を加え、40℃で2時間撹拌した。その後、ジメチルホルアミドジメチルアセタール(三菱レーヨン(株)製、以下、DFAと呼ぶ)7.14g(0.06モル)をNMP5gで希釈した溶液を10分かけて滴下した。滴下後、40℃で2時間撹拌を続けた。撹拌終了後、溶液を水2Lに投入して、ポリマー固体の沈殿をろ過で集めた。さらに水2Lで3回洗浄を行い、集めたポリマー固体を50℃の真空乾燥機で72時間乾燥し、ポリイミド前駆体(A-3)を得た。
乾燥窒素気流下、ODPA31.0g(0.10モル)をNMP500gに溶解させた。ここに合成例1で得られたヒドロキシル基含有ジアミン化合物39.30g(0.065モル)とSiDA1.24g(0.005モル)をNMP50gとともに加えて、20℃で1時間反応させ、次いで40℃で2時間反応させた。続いて、プロピレンオキシドおよびテトラメチレンエーテルグリコール構造を含むジアミン(RT-1000)10.00g(0.010モル)をNMP10gとともに加えて、40℃で1時間反応させた。次に末端封止剤として4-アミノフェノール4.36g(0.04モル)をNMP5gとともに加え、40℃で2時間反応させた。その後、DFA7.14g(0.06モル)をNMP50gで希釈した溶液を10分かけて滴下した。滴下後、40℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、ポリイミド前駆体(A-4)を得た。
乾燥窒素気流下、BAHF29.30g(0.08モル)、SiDA1.24g(0.005モル)、末端封止剤として、3-アミノフェノール(東京化成工業(株)製)3.27g(0.03モル)をNMP80gに溶解させた。ここにODPA31.2g(0.1モル)をNMP20gとともに加えて、60℃で1時間反応させ、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥し、ポリイミド(A-5)の粉末を得た。
乾燥窒素気流下、ODPA31.0g(0.10モル)をNMP500gに溶解させた。ここにBAHF25.60g(0.070モル)とSiDA1.24g(0.005モル)をNMP50gとともに加えて、20℃で1時間反応させ、次いで40℃で2時間反応させた。続いて、プロピレンオキシドおよびテトラメチレンエーテルグリコール構造を含むジアミン(RT-1000)10.00g(0.010モル)をNMP10gとともに加えて、40℃で1時間反応させた。次に末端封止剤として4-アミノフェノール4.36g(0.04モル)をNMP5gとともに加え、60℃で1時間反応させ、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥し、ポリイミド(A-6)の粉末を得た。
(B)成分:
(C)成分:
(C1)成分 :プロピレングリコールモノメチルエーテル(PGME)(沸点120℃)
プロピレングリコールモノメチルエーテルアセテート(PGMEA)(沸点146℃)
(C2)成分 :ガンマブチロラクトン(GBL)
熱架橋剤成分:下記に示す(D-1)、(D-2)、および(D-3)
N,N-ジメチルイソブチルアミド(DMIB):分子量:115;融点:-34℃;沸点:176℃
1,3-ジメチル-2-イミダゾリジノン(DMI)分子量:114;融点:8℃;沸点:222℃
(F)成分:下記に示す(F-1)
ラジカル重合性化合物:ジペンタエリスリトールヘキサアクリレート(DPHA)。
合成例2で得られた樹脂(A-1)10gに(C)成分、熱架橋剤、(E)成分およびその他成分を表1に示す質量部で加えてワニスを作製した。これらの特性を上記評価方法により測定した。測定結果を表2に示す。
合成例2~7で得られた樹脂(A-1)~(A-6)のいずれか10gに感光剤(B-1)~(B-3)のいずれかを2.0g、さらに(C)成分、熱架橋剤、(E)成分およびその他成分を表3、4に示す質量部で加えてワニスを作製した。これらの特性を上記評価方法により測定した。測定結果を表5、6に示す。
1’ 半導体チップ
2 Alパッド
3 パッシベーション膜
4 絶縁膜
5 金属膜
6 金属配線
7 絶縁膜
8 バリアメタル
9 スクライブライン
10 ハンダバンプ
11 封止樹脂
12 基板
13 絶縁膜
14 絶縁膜
15 金属膜
16 金属配線
17 金属配線
18 電極
19 封止樹脂
20 支持基板
21 電極パッド
22 絶縁膜
23 金属配線
24 Cuポスト
25 ハンダバンプ
26 半導体チップ
27 TFT
28 配線
29 TFT絶縁層
30 平坦化層
31 透明電極
32 基板
33 コンタクトホール
34 絶縁層
Claims (18)
- (A)ポリイミド、ポリイミド前駆体、ポリベンゾオキサゾール、ポリベンゾオキサゾール前駆体、その他のポリアミド、およびこれらの共重合体から選択される1種類以上の樹脂、(D)エポキシ基数が3以上の熱架橋剤、および(E)分子量が60以上1000以下の第3級アミド構造を有する化合物を含む、樹脂組成物。
- さらに、(B)感光剤を含有する請求項1に記載の樹脂組成物。
- 前記(A)成分が、一般式(1)または一般式(2)で表される構造単位を有するアルカリ可溶性樹脂である、請求項1または2に記載の樹脂組成物:
- 前記(E)成分が、一般式(4)~一般式(6)で表される化合物から選ばれる1種類以上の化合物である、請求項1~4のいずれかに記載の樹脂組成物:
- 前記(E)成分が、融点-70℃以上15℃以下かつ沸点100℃以上400℃以下の化合物であり、その含有量が、(A)成分100質量部に対し、4質量部以上1600質量部以下である、請求項1~5のいずれかに記載の樹脂組成物。
- さらに、(C)溶媒を含み、前記(C)溶媒が、(C1)大気圧下における沸点が100℃以上150℃以下の溶媒を含み、前記(C1)成分の含有量が全液体成分100質量%のうち、0.1質量%以上40質量%以下である、請求項1~7のいずれかに記載の樹脂組成物。
- 樹脂組成物を乾燥後13μmとなるよう基板上に塗布し、120℃、3分間加熱乾燥して得られた樹脂膜に含まれる前記(E)成分の含有量が0.001質量%以上30質量%以下である、請求項1~8のいずれかに記載の樹脂組成物。
- 請求項1~9のいずれかに記載の樹脂組成物を硬化した硬化膜。
- 硬化膜に含まれる前記(E)成分の含有量が0.05ppm以上1000ppm以下である、請求項10に記載の硬化膜。
- 請求項1~9のいずれかに記載の樹脂組成物を基板上に塗布し、乾燥して樹脂膜を形成する工程、樹脂膜を露光する露光工程、露光された樹脂膜を現像する現像工程、および現像された樹脂膜を加熱処理する加熱処理工程を含む硬化膜の製造方法。
- 金属配線および絶縁膜を有する半導体装置であって、請求項10または11に記載の硬化膜を絶縁膜として有する半導体装置。
- 金属配線の幅と隣り合う配線同士の間隔が5μm以下である、請求項13に記載の半導体装置。
- さらに半導体チップを含み、金属配線が該半導体チップと電気的に接続されている請求項13または14に記載の半導体装置。
- 前記半導体チップが封止樹脂に封止されており、前記半導体チップおよび前記封止樹脂の上に前記絶縁膜が層間絶縁膜として配置され、該層間絶縁膜の上に前記金属配線が配置された請求項15に記載の半導体装置。
- 配線および層間絶縁膜からなる複数の再配線層が積層され、隣接する各再配線層のうち、半導体チップに近い方の再配線層の金属配線の幅と隣り合う配線同士の間隔が、半導体チップから遠い方の再配線層の金属配線の幅と隣り合う配線同士の間隔と比べて、同じまたは狭くなる請求項15または16に記載の半導体装置。
- 仮貼り材料が配置された支持基板上に、金属配線および請求項10または11に記載の硬化膜からなる再配線層を複数積層する工程と、
その上に半導体チップと封止樹脂を配置して半導体パッケージを作成する工程と、
その後、該支持基板と該半導体パッケージを剥離する工程を含む、半導体装置の製造方法。
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JPWO2018066395A1 (ja) | 2019-07-25 |
TWI746650B (zh) | 2021-11-21 |
KR102380068B1 (ko) | 2022-03-31 |
CN109563342A (zh) | 2019-04-02 |
JP7013872B2 (ja) | 2022-02-15 |
KR20190065998A (ko) | 2019-06-12 |
TW201821539A (zh) | 2018-06-16 |
CN109563342B (zh) | 2021-06-22 |
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