WO2018043250A1 - Composition de résine photosensible, film durci, dispositif d'affichage el organique, composant électronique semi-conducteur, et dispositif à semi-conducteur - Google Patents

Composition de résine photosensible, film durci, dispositif d'affichage el organique, composant électronique semi-conducteur, et dispositif à semi-conducteur Download PDF

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WO2018043250A1
WO2018043250A1 PCT/JP2017/030144 JP2017030144W WO2018043250A1 WO 2018043250 A1 WO2018043250 A1 WO 2018043250A1 JP 2017030144 W JP2017030144 W JP 2017030144W WO 2018043250 A1 WO2018043250 A1 WO 2018043250A1
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photosensitive resin
resin composition
film
acid
mass
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PCT/JP2017/030144
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English (en)
Japanese (ja)
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惇 早坂
洋平 木内
奥田　良治
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東レ株式会社
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Priority to JP2017545610A priority Critical patent/JP7062953B2/ja
Publication of WO2018043250A1 publication Critical patent/WO2018043250A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • 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
    • 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
    • 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
    • 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
    • G03F7/075—Silicon-containing compounds
    • 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

Definitions

  • the present invention relates to a photosensitive resin composition, a cured film using the same, an organic EL display device, a semiconductor electronic component, and a semiconductor device. More specifically, the present invention relates to a photosensitive resin composition suitably used for a surface protective film of a semiconductor element, an interlayer insulating film, an insulating layer of an organic electroluminescent element, and the like.
  • polyimide resins, polybenzoxazole resins, and the like that are excellent in heat resistance, mechanical properties, and the like have been widely used for surface protective films and interlayer insulating films of semiconductor elements of electronic devices.
  • polyimide or polybenzoxazole is used as a surface protective film or an interlayer insulating film
  • one method for forming a through hole or the like is etching using a positive photoresist.
  • the process includes application and peeling of a photoresist and is complicated. Therefore, studies have been made on heat-resistant materials imparted with photosensitivity for the purpose of rationalizing work processes.
  • Polyimide and polybenzoxazole can obtain a thin film having excellent heat resistance and mechanical properties by thermally dehydrating and cyclizing their precursor coating film, but in that case, at a high temperature around 350 ° C. Requires heat treatment.
  • MRAM Magnetic Resistive Random Access Memory
  • MRAM Magnetic Resistive Random Access Memory
  • a surface protective film is cured by heat treatment at a low temperature of about 250 ° C. or lower.
  • polyimide resins and polybenzoxazole resins that provide performance comparable to cured films cured by heat treatment at a high temperature of around 350 ° C.
  • a method for obtaining a polyimide-based resin and a polybenzoxazole-based resin that are cured by heat treatment at a low temperature a method of adding a ring closure accelerator, an organic group that promotes ring closure at a low temperature in the unit structure, A method of using polyimide or polybenzoxazole which has been previously ring-closed after imparting alkali solubility is known.
  • the photosensitive resin composition when used for applications such as semiconductors, the cured film obtained by heat treatment remains as a permanent film in the device, so the physical properties as the cured film are very important.
  • adhesion with the material formed on the surface of the semiconductor chip is important.
  • adhesion with a metal material used for electrodes, wiring, etc. is important.
  • the resin composition containing a resin that can be cured by heat treatment at a low temperature has a problem of low adhesion to the metal used as the wiring material.
  • a heat-resistant resin is considered not to have high adhesion strength to a metal material due to its rigid main chain structure, and in particular, in the case of a cured film of a resin composition imparted with photosensitivity, the photosensitive resin constituting the resin composition Since additives such as an agent, a sensitizer, an acid generator and a dissolution regulator remain in the cured film even after heat curing, the adhesion strength is lower than those containing no additive.
  • a positive photosensitive resin composition comprising an aqueous alkali soluble polymer, a photoacid generator, and a silane compound containing four or more specific functional groups directly bonded to an Al atom, Ti atom, or Si atom Products
  • a heat-resistant resin precursor compositions such as polyimide precursors, and specific amino compounds or thiol derivatives (see Patent Document 2) have been proposed.
  • the photosensitive resin composition and the heat-resistant resin precursor composition described in Patent Documents 1 and 2 generate an organic acid when used as a cured film, corrode metal wiring, especially copper, As a result, the adhesion may be reduced. Further, the cured film itself is decomposed by the generated organic acid, and the mechanical properties, particularly the elongation, may be lowered, resulting in lack of device reliability.
  • an object of the present invention is to provide a photosensitive resin composition that can provide a cured film having excellent adhesion to a metal material, particularly copper, even in heat treatment at a low temperature, and having a high elongation.
  • the photosensitive resin composition of this invention has the following structures. That is, it is a photosensitive resin composition comprising (A) an alkali-soluble resin having a structural unit represented by the general formula (1) and (B) a photocrosslinking agent.
  • A an alkali-soluble resin having a structural unit represented by the general formula (1)
  • B a photocrosslinking agent.
  • X 1 and X 2 represent a divalent to decavalent organic group
  • Y 1 represents a divalent to tetravalent organic group
  • Y 2 represents an aliphatic group having 2 or more carbon atoms.
  • the integer satisfying the range of n1 / (n1 + n2) ⁇ 1 and the arrangement of each repeating unit may be block-like or random.
  • the photosensitive resin composition of the present invention can provide a cured film having excellent adhesion to a metal material, particularly copper, and high elongation even in heat treatment at a low temperature.
  • FIG. 1 is an enlarged cross-sectional view of a pad portion of a semiconductor device having bumps.
  • 2a to 2f are diagrams showing a detailed manufacturing method of a semiconductor device having bumps.
  • 3a to 3f are explanatory views illustrating a method for manufacturing a semiconductor device in the RDL first method.
  • FIG. 4 is a cross-sectional view showing an example of a TFT substrate.
  • the photosensitive resin composition of the present invention includes (A) an alkali-soluble resin having a structural unit represented by the general formula (1), and (B) a photocrosslinking agent.
  • the component (A), the component (B), the component (C), the component (D), and the component (E) may be omitted.
  • the cured film formed by curing the photosensitive resin composition of the present invention preferably reduces the generation of organic acid by using a specific (B) photocrosslinking agent and suppresses corrosion of metals, particularly copper. , Adhesion can be improved. Moreover, it is preferable to add (C) component, and interaction with copper increases further, As a result, adhesiveness with a copper substrate improves.
  • the resin of (A) can easily be stretched by setting the diamine residue constituting the component (A), that is, Y 2 to have 2 or more carbon atoms. As a result, a cured film obtained by curing the photosensitive resin composition becomes a high elongation material.
  • the photosensitive resin composition of the present invention can obtain a cured film having high adhesion to a metal material, particularly copper, even in a heat treatment at a low temperature of 250 ° C. or less.
  • the (A) alkali-soluble resin of the present invention has a structural unit represented by the general formula (1).
  • X 1 and X 2 are divalent to decavalent organic groups, preferably aliphatic carboxylic acid residues.
  • Y 1 is a divalent to tetravalent organic group, preferably an organic group having an aromatic group, more preferably an organic group having a phenyl group.
  • Y 2 is a divalent organic group having an aliphatic structure having 2 or more carbon atoms, preferably an aliphatic diamine residue.
  • R 1 and R 2 represent hydrogen or an organic group having 1 to 20 carbon atoms.
  • n1 and n2 are integers satisfying the ranges of 1 ⁇ n1 ⁇ 500, 1 ⁇ n2 ⁇ 500, and 0.05 ⁇ n1 / (n1 + n2) ⁇ 1.
  • the arrangement of each repeating unit may be block or random.
  • the alkali-soluble resin is an alkali-soluble polyamide having an organic group derived from an aliphatic diamine and having a repeating unit represented by the general formula (1), and X 1 (COOH) 2 or X 2
  • It is a polyamide that can be obtained by polycondensation of bisaminophenol and diamine having the structure of NH 2 ) 2 (OH) 2 and Y 2 (NH 2 ) 2 .
  • the two groups of amino group and hydroxyl group of the bisaminophenol are in the ortho positions to each other, and this polyamide is dehydrated and ring-closed by heating at about 250 ° C. to 400 ° C.
  • the phenol moiety may change to benzoxazole.
  • the base polymer of the photosensitive resin composition of the present invention may or may not be closed after heat curing.
  • the alkali-soluble resin has a value of n1 / (n1 + n2) in the general formula (1) of 0.05 or more, preferably 0.5 or more, from the viewpoint of solubility in an alkali solution. It is more preferably 7 or more, and further preferably 0.8 or more. Further, from the viewpoint of low stress properties, the value of n1 / (n1 + n2) is less than 1, and more preferably 0.95 or less.
  • Examples of the dicarboxylic acid having a structure of X 1 (COOH) 2 or X 2 (COOH) 2 include the case where X 1 and X 2 are aromatic groups selected from the following structural formulas. It is not limited.
  • A represents — (direct bond), —O—, —S—, —SO 2 —, —COO—, —OCO—, —CONH—, —NHCO—, —C (CH 3 ) 2 —, (It has a divalent group selected from the group consisting of —C (CF 3 ) 2 —.)
  • X 1 and X 2 in the general formula (1) are structural units represented by the general formulas (2) to (4), respectively. It is preferable to have at least one of them.
  • dicarboxylic acid having the structure represented by the general formulas (2) to (4) examples include dimethylmalonic acid, ethylmalonic acid, isopropylmalonic acid, di-n-butylmalonic acid, succinic acid, and tetrafluorosuccinic acid.
  • the dicarboxylic acid having a structure of X 1 (COOH) 2 or X 2 (COOH) 2 is preferably succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid , Sebacic acid, 1,9-nonanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosandioic acid Acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, penta
  • Y 2 has an aliphatic structure, preferably an aliphatic diamine residue, and more preferably an alkylene oxide structure represented by the general formula (5). It has a unit.
  • R 6 to R 9 each independently represents an alkylene group having 2 to 10 carbon atoms, and a, b and c are 0 ⁇ a ⁇ 20 and 0 ⁇ b ⁇ 20, respectively. It represents an integer in the range of 0 ⁇ c ⁇ 20, and the arrangement of each repeating unit may be block or random. * Indicates a chemical bond.
  • examples of the diamine having a structural unit represented by the general formula (5) as Y 2 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,
  • the molecular structure of the structural unit represented by Y 2 in the general formula (1) is 150 or more, so that the polyamide structure of the component (A) becomes flexible and cured. High elongation when formed into a film. Furthermore, since the component (A) becomes flexible, the stress on the wafer when the cured film is formed can be relaxed, and the residual stress between the cured film and the substrate is reduced. As a result, the adhesion can be improved. In addition, the introduction of a low UV-absorbing flexible group improves i-ray transmission and can simultaneously achieve high sensitivity.
  • the molecular weight of the structural unit represented as Y 2 is preferably 150 or more, more preferably 600 or more, and still more preferably 900 or more. Moreover, if molecular weight is 2,000 or less, it is preferable at the point which maintains the solubility to an alkaline solution, 1800 or less is more preferable, and 1500 or less is further more preferable.
  • the molecular weight is more preferably 600 or more and 1,800 or less, and further preferably 900 or more and 1,500 or less. Thereby, elongation and a sensitivity can be raised more.
  • the molecular weight of Y 2 component in the general formula (1) of the resin of component (A) with respect to the diamine monomer containing Y 2 structure, for example to measure such in LC-MS, can be obtained as the molecular weight of the main signal.
  • component (A) in addition diamine having a structure of Y 2 (NH 2) 2, it may be copolymerized with other diamines.
  • other diamines include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 3,4'-diaminodiphenylsulfone, 4 , 4'-diaminodiphenylsulfone, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 1,4-bis (4-aminophenoxy) benzene, benzine, m-phenylenediamine, p-phenylenediamine 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis (4-aminophenoxy) benzen
  • diamine to be copolymerized can be used as it is or as a corresponding diisocyanate compound or trimethylsilylated diamine. Moreover, you may use combining these 2 or more types of diamine components.
  • an aliphatic group having a siloxane 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.
  • the resin of component (A) is end-capped with a main chain terminal such as monoamine, acid anhydride, monocarboxylic acid, monoacid chloride compound, monoactive ester compound, etc. It is preferable to seal with a stopper.
  • a terminal sealing agent having a hydroxyl group, a carboxyl group, a sulfonic acid group, a thiol group, a vinyl group, an ethynyl group, or an allyl group, the dissolution rate of the resin in an alkaline solution and the resulting curing can be obtained.
  • the mechanical properties of the membrane can be easily adjusted to a preferred range.
  • the introduction ratio of the end-capping agent is preferably 0.1 mol% in order to prevent the molecular weight of the resin of the component (A) from being increased and the solubility in an alkaline solution from being lowered with respect to the total amine component. More preferably, it is 5 mol% or more, and preferably 60 mol% or less, particularly preferably 50 mol in order to suppress a decrease in mechanical properties of the cured film obtained by lowering the molecular weight of the resin of component (A). % Or less.
  • a plurality of different end groups may be introduced by reacting a plurality of end-capping agents.
  • Monoamines include M-600, M-1000, M-2005, M-2070 (above trade name, manufactured by HUNTSMAN Co., Ltd.), aniline, 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 5- Amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-amino Naphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy -7-aminonaphthalene, 2-carboxy-6- Minonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzo
  • Acid anhydrides such as phthalic anhydride, maleic anhydride, nadic anhydride, cyclohexanedicarboxylic anhydride, 3-hydroxyphthalic anhydride, etc., as acid anhydrides, monocarboxylic acids, monoacid chloride compounds, and monoactive ester compounds 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene Monocarboxylic acids such as 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid, 4-carboxybenzenesulfonic acid, Monoacid chloride compounds in which these carboxyl groups are converted to acid chlorides, terephthalic acid, phthal
  • the component (A) used in the present invention may be copolymerized with another structure such as polyimide as long as it includes the structure represented by the general formula (1).
  • the component (A) may have other structures, but preferably has 10 to 100 mol% of the structural unit represented by the general formula (1).
  • the component (A) in the present invention preferably has a weight average molecular weight of 5,000 or more and 50,000 or less.
  • a weight average molecular weight 5,000 or more and 50,000 or less.
  • GPC gel permeation chromatography
  • the folding resistance after curing can be improved.
  • the weight average molecular weight is 50,000 or less
  • developability with an alkaline solution can be improved.
  • 20,000 or more is more preferable.
  • at least 1 type of weight average molecular weight should just be the said range.
  • the solvent used in the polymerization of the component (A) (hereinafter referred to as a polymerization solvent) is not particularly limited as long as it can dissolve the tetracarboxylic dianhydrides and diamines that are raw material monomers.
  • a polymerization solvent is not particularly limited as long as it can dissolve the tetracarboxylic dianhydrides and diamines that are raw material monomers.
  • the polymerization solvent is preferably used in an amount of 100 parts by mass or more, more preferably 150 parts by mass or more in order to dissolve the resin after the reaction with respect to 100 parts by mass of the obtained resin. Therefore, it is preferable to use 1,900 parts by mass or less, and more preferably 950 parts by mass or less.
  • the photosensitive resin composition of the present invention contains (B) a photocrosslinking agent.
  • the photocrosslinking agent is a negative type that is cured by light, and preferably contains (b-1) a photoinitiator and (b-2) a photopolymerizable compound.
  • Photoinitiators include, for example, benzophenones such as benzophenone, Michler's ketone, 4,4, -bis (diethylamino) benzophenone, 3,3,4,4, -tetra (t-butylperoxycarbonyl) benzophenone And benzylidenes such as 3,5-bis (diethylaminobenzylidene) -N-methyl-4-piperidone and 3,5-bis (diethylaminobenzylidene) -N-ethyl-4-piperidone, 7-diethylamino-3-thenonylcoumarin 4,6-dimethyl-3-ethylaminocoumarin, 3,3-carbonylbis (7-diethylaminocoumarin), 7-diethylamino-3- (1-methylbenzimidazolyl) coumarin, 3- (2-benzothiazolyl) -7- Coumarins such as diethylaminocoumarin, 2-t- Anthraquinones
  • 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime, 1-phenyl-1,2-propanedione-2- (o-) is particularly preferable.
  • Benzoyl) oxime, bis ( ⁇ -isonitrosopropiophenoneoxime) isophthal, 1,2-octanedione-1- [4- (phenylthio) phenyl] -2- (o-benzoyloxime), OXE02, NCI-831 is there. These may be used alone or in combination of two or more.
  • the content of the photoinitiator is preferably 0.1 to 60 parts by mass, more preferably 0.2 to 40 parts by mass with respect to 100 parts by mass of the total amount of the component (A).
  • it is 0.1 part by mass or more, it is preferable in that sufficient radicals are generated by light irradiation and the sensitivity is improved, and when it is 60 parts by mass or less, the light non-irradiated part is cured by generation of excessive radicals. Alkali developability is improved.
  • the photopolymerizable compound is preferably a compound having an unsaturated carbon-carbon bond, that is, a polymerizable unsaturated compound.
  • unsaturated double bond functional groups such as vinyl group, allyl group, acryloyl group, methacryloyl group and / or unsaturated triple bond functional groups such as propargyl group.
  • conjugated vinyl groups and acryloyl groups A methacryloyl group is preferred in terms of polymerizability.
  • the number of functional groups contained is preferably 1 to 4 from the viewpoint of stability, and they may not be the same group.
  • the number average molecular weight of the photopolymerizable compound is not particularly limited, but the number average molecular weight is preferably 800 or less because of good compatibility with the polymer and the reactive diluent.
  • the number average molecular weight is preferably 30 or more for the purpose of suppressing the solubility in the developer after exposure.
  • polymerizable unsaturated compound examples include diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, and trimethylol.
  • the content of the polymerizable unsaturated compound is preferably 1 to 40 parts by mass with respect to 100 parts by mass of the component (A).
  • Part or more is more preferable, and 20 parts by mass or less is more preferable for the purpose of obtaining a highly perpendicular pattern shape.
  • the photosensitive resin composition of the present invention can contain (C) a compound having at least one of an oxygen atom, a sulfur atom and a nitrogen atom in the molecule.
  • the component (C) in the present invention is a compound that interacts with metal, particularly copper, and by containing this, the adhesion between the heat-cured film and the metal material is greatly improved.
  • the component (C) in the present invention is preferably a compound represented by the general formula (6).
  • R 10 to R 12 each represents an oxygen atom, a sulfur atom, or a nitrogen atom, and at least one of R 10 to R 12 represents a sulfur atom.
  • R 10 represents an oxygen atom or a sulfur atom when l is 0, and a nitrogen atom when l is 1.
  • m and n are integers of 1 to 2, u and v are 0
  • R 11 and R 12 each represents an oxygen atom or a sulfur atom when u and v are 0, and represents a nitrogen atom when u and v are 1.
  • R 13 to R 17 are each independently selected.
  • R 13 to R 15 are hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, alkyl ether group, alkylsilyl group, alkoxysilyl group, aryl group, aryl ether group, carboxyl group, carbonyl group, allyl group, vinyl A group, a heterocyclic group, a combination thereof, and the like, and may further have a substituent.
  • R 13 to R 17 may form a ring with groups adjacent to each other.
  • Examples of the compound represented by the general formula (6) include the following, but are not limited to the following structures.
  • the content of the component (C) is preferably 1 to 40 parts by mass with respect to 100 parts by mass of the component (A), and more preferably 3 parts by mass or more for the purpose of suppressing solubility in the developer after exposure. 20 mass parts or less are more preferable from a viewpoint of storage stability.
  • the photosensitive resin composition of the present invention preferably contains (D) an organic solvent having a boiling point of 200 ° C. or more and 260 ° C. or less at 1013 hPa, and (E) an organic solvent having a boiling point of 1013 hPa or more and 100 ° C. or more and less than 200 ° C.
  • the content of the organic solvent having a boiling point in the (D) 1013 hPa of 200 ° C. or more and 260 ° C. or less is 5% by mass or more and 70% by mass or less
  • the boiling point in the (E) 1013 hPa is 100 ° C. or more and 200 ° C.
  • the content of the organic solvent at a temperature lower than 0 ° C. is preferably 30% by mass or more and 95% by mass or less with respect to the total amount of the organic solvent.
  • the boiling point of component (D) at 1013 hPa is preferably 200 ° C. or higher, since it can mitigate a decrease in fluidity due to drying of the coating film at the time of coating and in the drying step. It is preferable at the point which suppresses the residual of the organic solvent to a conductive resin film, More preferably, it is 250 degrees C or less.
  • the content of the component (D) is 5% by mass or more and 70% by mass or less with respect to the total amount of the organic solvent.
  • the content of the component (D) is preferably 5% by mass or more, more preferably 15% by mass or more, and further preferably 30% by mass or more in that a sufficient step filling effect can be obtained by the presence of a high boiling point solvent.
  • the content of the component (D) is preferably 70% by mass or less from the viewpoint that the boiling point of the solvent contained in the photosensitive resin composition can be maintained to such an extent that it does not require time for the drying step. 60 mass% or less is more preferable and 50 mass% or less is still more preferable at the point which can suppress the residual
  • the component (D) is preferably one that dissolves the resin of the component (A). Specifically, 1,3-dimethyl-2-imidazolidinone (boiling point 220 ° C.), N, N-dimethylpropyleneurea (boiling point 246 ° C.), 3-methoxy-N, N-dimethylpropionamide (boiling point 216 ° C.) ), Deltavalerolactone (boiling point 230 ° C.), gamma butyrolactone (boiling point 203 ° C.), N-methyl-2-pyrrolidone (boiling point 204 ° C.), and the like.
  • the photosensitive resin composition of the present invention preferably contains (E) an organic solvent having a boiling point at 1013 hPa of 100 ° C. or higher and lower than 200 ° C.
  • the organic solvent having a boiling point at 1013 hPa of 100 ° C. or more and less than 200 ° C. can be removed from the coating film in a short time in the drying step.
  • the boiling point at 1013 hPa is 100 ° C. or higher, the situation where the resin component (A) is dissolved and the solid content is precipitated can be avoided.
  • the content of the component (E) is 30% by mass to 95% by mass with respect to the total amount of the organic solvent, and the total of the component (D) and the component (E) is 100% by mass with respect to the total amount of the organic solvent. It is as follows.
  • the content of the component (E) is preferably 30% by mass or more, more preferably 40% by mass or more, in that the boiling point of the solvent contained in the photosensitive resin composition can be maintained to such an extent that it does not require time for the drying step. 50 mass% or more is more preferable.
  • the content of the component (E) is preferably 95% by mass or less, more preferably 85% by mass or less, and more preferably 70% by mass or less in that a sufficient step filling effect can be obtained by combining with the component (D). Further preferred.
  • the effect of improving the level difference embedding accompanying maintaining the fluidity of the photosensitive resin composition at the time of coating and the subsequent drying step is remarkably exhibited.
  • ethyl lactate (boiling point 154 ° C.), butyl lactate (boiling point 186 ° C.), dipropylene glycol dimethyl ether (boiling point 171 ° C.), diethylene glycol dimethyl ether (boiling point 162 ° C.), diethylene glycol ethyl methyl ether (boiling point 176 ° C.), diethylene glycol Diethyl ether (bp 189 ° C.), 3-methoxybutyl acetate (bp 171 ° C.), ethylene glycol monoethyl ether acetate (bp 160 ° C.), diacetone alcohol (bp 166 ° C.), N-cyclohexyl-2-pyrrolidone (bp 154) ° C), N, N-dimethylformamide (boiling point 153 °
  • ethyl lactate diethylene glycol ethyl methyl ether, N, N-dimethylisobutyric acid amide, or propylene glycol monomethyl ether is more preferable.
  • the boiling point of organic solvents at 1013 hPa is described in the literature of “CRC Handbook of Chemistry and Physics” and “Aldrich Handbook of Fine Chemical and Laboratory Equipment”.
  • the boiling point of an organic solvent not described in the known literature can be measured by a commercially available boiling point measuring device, for example, FP81HT / FP81C (manufactured by METTLER TOLEDO).
  • the content of the total amount of the organic solvent of the present invention is preferably 50 parts by mass to 2000 parts by mass with respect to 100 parts by mass of the resin (A). It is preferable that it is 50 parts by mass or more from the viewpoint that the polymer dissolves in the organic solvent without precipitation, and more preferably 100 parts by mass or more. It is preferable that it is 2000 parts by mass or less in that it can be controlled to have a viscosity suitable for coating, and more preferably 1500 parts by mass.
  • the photosensitive resin composition of the present invention may contain a low molecular compound having a phenolic hydroxyl group as long as it does not reduce the shrinkage residual film ratio after curing.
  • a low molecular compound having a phenolic hydroxyl group By containing the low molecular weight compound having a phenolic hydroxyl group, it is easy to adjust the alkali solubility during pattern processing.
  • the content of the low molecular weight compound having a phenolic hydroxyl group that is preferable for the purpose of manifesting the effect is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more with respect to 100 parts by mass of the component (A). From the viewpoint of maintaining mechanical properties such as elongation, it is preferably 30 parts by mass or less, more preferably 15 parts by mass or less.
  • the photosensitive resin composition of the present invention may contain a thermal crosslinking agent (F) as necessary.
  • a thermal crosslinking agent a compound having at least two alkoxymethyl groups and / or methylol groups and a compound having at least two epoxy groups and / or oxetanyl groups are preferably used, but are not limited thereto.
  • a condensation reaction is caused with the component (A) during curing after patterning to form a crosslinked structure, and mechanical properties such as elongation of the cured film are improved.
  • two or more kinds of thermal cross-linking agents may be used, which enables a wider range of designs.
  • Preferred examples of the compound having at least two alkoxymethyl groups and / or methylol groups include, for example, DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML-OCHP, DML-PFP, DML-PSBP, DML-POP, DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DML-BisOCHP-Z, DML-BPC, DML-BisOC-P, DMOM-PC, DMOM-PTBP, DMOM-MBPC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM-BP, T OM-BPE, TMOM-BPA, TMOM-BPAF, TMOM-BPAP
  • Preferred examples of the compound having at least two epoxy groups and / or oxetanyl groups include, for example, bisphenol A type epoxy resins, bisphenol A type oxetanyl resins, bisphenol F type epoxy resins, bisphenol F type oxetanyl resins, propylene glycol diesters.
  • examples thereof include, but are not limited to, epoxy group-containing silicones such as glycidyl ether, polypropylene glycol diglycidyl ether, and polymethyl (glycidyloxypropyl) siloxane.
  • EPICLON (registered trademark) 850-S, EPICLON HP-4032, EPICLON HP-7200, EPICLON HP-820, EPICLON HP-4700, EPICLON EXA-4710, EPICLON HP-4770, EPICLON EXA-859P EPICLON EXA-1514, EPICLON EXA-4880, EPICLON EXA-4850-150, EPICLON EXA-4850-1000, EPICLON EXA-4816, EPICLON EXA-4822 (trade name, manufactured by Dainippon Ink & Chemicals, Inc.)
  • Lika Resin (registered trademark) BEO-60E (trade name, manufactured by Shin Nippon Rika Co., Ltd.), EP-4003S, EP-4000S (trade names, Co., Ltd.) ADEKA), and the like, are available from each company. Two or more of these may be contained.
  • the content of the (F) thermal crosslinking agent used in the present invention is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, further preferably 3 parts by mass with respect to 100 parts by mass of the component (A). From the viewpoint of maintaining mechanical properties such as elongation, it is preferably 300 parts by mass or less, more preferably 200 parts by mass or less, still more preferably 100 parts by mass or less, still more preferably 70 parts by mass or less, and particularly preferably 40 parts by mass. It is below mass parts.
  • the photosensitive resin composition of the present invention includes surfactants, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, alcohols such as ethanol, cyclohexanone, methyl for the purpose of improving the wettability with the substrate as necessary.
  • surfactants esters such as ethyl lactate and propylene glycol monomethyl ether acetate
  • alcohols such as ethanol, cyclohexanone
  • Ketones such as isobutyl ketone and ethers such as tetrahydrofuran and dioxane may be contained.
  • the preferable content of the compound used for the purpose of improving the wettability with these substrates is 0.001 part by mass or more with respect to 100 parts by mass of the component (A), preferably from the viewpoint of obtaining an appropriate film thickness. It is 1800 parts by mass or less, more preferably 1500 parts by mass or less.
  • the photosensitive resin composition of the present invention may contain inorganic particles.
  • Preferred specific examples include, but are not limited to, silicon oxide, titanium oxide, barium titanate, alumina, talc and the like.
  • the average primary particle size of these inorganic particles is preferably from 1 nm to 100 nm, more preferably from 10 nm to 60 nm, from the viewpoint of photosensitivity.
  • the individual particle diameters of these inorganic particles can be measured with a scanning electron microscope, for example, a scanning electron microscope manufactured by JEOL Ltd., JSM-6301NF.
  • the average primary particle diameter can be calculated by measuring the diameter of 100 particles randomly selected from the photograph and obtaining the arithmetic average thereof.
  • silane coupling agent such as trimethoxyaminopropyl silane, trimethoxy epoxy silane, trimethoxy vinyl silane, trimethoxy thiol propyl silane as long as storage stability is not impaired in order to enhance adhesion to the silicon substrate. May be.
  • the preferable content of the compound used for enhancing the adhesion to these silicon substrates is 0.01 parts by mass or more with respect to 100 parts by mass of the component (A), which is preferable from the viewpoint of maintaining mechanical properties such as elongation. Is 5 parts by mass or less.
  • the viscosity of the photosensitive resin composition of the present invention is preferably 2 to 5000 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 5000 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 photosensitive resin composition of the present invention is applied to the substrate.
  • a wafer made of silicon, ceramics, gallium arsenide, or the like on which a metal is formed as an electrode or wiring is used, but is not limited thereto.
  • the application method include spin coating using a spinner, spray coating, and roll coating.
  • 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 can be pretreated with the above-described silane coupling agent.
  • Surface treatment is performed by spin coating, dipping, spray coating, steam treatment or the like. In some cases, a heat treatment at 50 to 300 ° C. is then performed to advance the reaction between the substrate and the silane coupling agent.
  • a method for producing a relief pattern of a cured film according to the present invention includes a step of applying a photosensitive resin composition on a substrate or laminating a photosensitive resin sheet on a substrate and drying to form a photosensitive resin film, a mask Or a step of exposing the photosensitive resin film using a direct drawing apparatus, a step of developing the exposed photosensitive resin film with an alkaline solution, and a heat treatment step of the photosensitive resin film after development.
  • a method for forming a photosensitive resin composition film on a substrate using the photosensitive resin composition of the present invention or a photosensitive sheet comprising the same will be described.
  • a varnish made of the photosensitive resin composition is applied on the substrate.
  • the coating method include spin coating using a spinner, spray coating, roll coating, slit coating, and screen printing.
  • the coating film thickness varies depending on the coating technique, the solid content concentration and the viscosity of the resin composition, etc., but it is usually preferable that the coating film thickness is 0.5 ⁇ m or more and 100 ⁇ m or less after drying.
  • the substrate coated with the photosensitive resin composition varnish is dried to obtain a photosensitive resin composition film.
  • the drying temperature and drying time may be in a range where the organic solvent can be volatilized, and it is preferable to appropriately set a range in which the photosensitive resin composition film is in an uncured or semi-cured state. Specifically, it is preferably performed in the range of 50 to 150 ° C. for 1 minute to several hours.
  • the photosensitive resin composition of the present invention when used as a photosensitive resin sheet, it is preferably applied to a support film and dried to form a photosensitive resin sheet.
  • the support film to be used is not particularly limited, various commercially available films such as a polyethylene terephthalate (PET) film, a polyphenylene sulfide film, and a polyimide film can be used.
  • PET polyethylene terephthalate
  • the bonding surface between the support film and the photosensitive resin sheet may be subjected to a surface treatment such as silicone, a silane coupling agent, an aluminum chelating agent, or polyurea in order to improve adhesion and peelability.
  • the thickness of the support film is not particularly limited, but is preferably in the range of 10 to 100 ⁇ m from the viewpoint of workability.
  • the photosensitive resin composition coated on the support film undergoes a drying process.
  • the drying temperature is preferably 50 ° C. or higher from the viewpoint of drying properties, and is preferably 150 ° C. or lower from the viewpoint of not impairing photosensitivity.
  • the film thickness of the photosensitive resin sheet is preferably 5 ⁇ m or more from the viewpoint of step embedding during lamination, and is preferably 150 ⁇ m or less from the viewpoint of film thickness uniformity.
  • the photosensitive resin sheet of this invention may have a protective film on a sheet
  • the photosensitive resin sheet surface can be protected from contaminants such as dust and dust in the atmosphere.
  • the protective film include polyolefin films and polyester films.
  • the protective film preferably has a small adhesive force with the photosensitive resin sheet.
  • the obtained photosensitive resin sheet is bonded to the substrate.
  • the substrate a wafer made of silicon, ceramics, gallium arsenide, or the like on which a metal is formed as an electrode or wiring is used, but is not limited thereto.
  • the thermocompression bonding can be performed by a heat press process, a heat laminating process, a heat vacuum laminating process, or the like.
  • the bonding temperature is preferably 40 ° C. or higher from the viewpoint of adhesion to the substrate and embedding. Further, the bonding temperature is preferably 150 ° C. or lower in order to prevent the photosensitive resin sheet from being cured at the time of bonding and deteriorating the resolution of pattern formation in the exposure / development process.
  • the photosensitive resin sheet formed from the photosensitive resin composition of the present invention, or a cured film obtained by curing the photosensitive resin composition is an organic material having a boiling point of 200 to 260 ° C. at (D) 1013 hPa in the cured film.
  • the amount of the solvent is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, preferably 1% by mass or less, more preferably 0.5% by mass with respect to the total mass of the cured film. It may be the following.
  • the component (D) 0.005% by mass or more the adhesion to the copper substrate is further improved, and by making it 1% by mass or less, the component (D) itself becomes outgas so as not to impair the reliability. Can be.
  • the mass% of the component (D) in the cured film is determined by measuring the mass of the collected cured film by the purge-and-trap method, the TPD-MS method, etc., and determining the value as the alkali-soluble resin (A). By calculating from the specific gravity of the component, the mass% of the compound in the cured film can be calculated.
  • the photosensitive resin composition is applied on a substrate and dried to form a photosensitive resin film, or the photosensitive resin sheet is laminated on the substrate and dried to form a photosensitive resin film.
  • substrates used include glass substrates, silicon wafers, ceramics, gallium arsenide, organic circuit substrates, inorganic circuit substrates, and those in which circuit materials are arranged on these substrates. It is not limited to.
  • Examples of organic circuit boards include: glass substrate copper-clad laminates such as glass cloth / epoxy copper-clad laminates, composite copper-clad laminates such as glass nonwoven fabrics / epoxy copper-clad laminates, polyetherimide resin substrates, polyethers Examples include heat-resistant / thermoplastic substrates such as ketone resin substrates and polysulfone resin substrates, polyester copper-clad film substrates, and polyimide copper-clad film substrates.
  • Examples of the inorganic circuit board include ceramic substrates such as an alumina substrate, an aluminum nitride substrate, and a silicon carbide substrate, and metal substrates such as an aluminum base substrate and an iron base substrate.
  • circuit components include conductors containing metals such as silver, gold and copper, resistors containing inorganic oxides, low dielectrics containing glass materials and / or resins, resins and high Examples thereof include high dielectric materials containing dielectric constant inorganic particles, insulators containing glass-based materials, and the like.
  • the photosensitive resin film formed by the above method is irradiated with actinic radiation through a mask having a desired pattern and exposed, or exposed directly without using a mask using a drawing apparatus.
  • Actinic rays used for exposure include ultraviolet rays, visible rays, electron beams, X-rays, YAG lasers, etc., but in the present invention, such as i-rays (365 nm), h-rays (405 nm), and g-rays (436 nm) of mercury lamps. It is preferable to use ultraviolet rays.
  • the photosensitive sheet when the support is made of a material transparent to these rays, the exposure may be performed without peeling the support from the photosensitive sheet.
  • aqueous solution of a compound exhibiting alkalinity such as dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, hexamethylenediamine and the like is preferable.
  • these alkaline aqueous solutions may contain polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Contains 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 alone or in combination of several kinds Good.
  • polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Contains alcohols such as isopropanol, esters such as ethy
  • Development can be carried out by spraying the developer on the coating surface, immersing in the developer, applying ultrasonic waves while immersing, or spraying the developer while rotating the substrate.
  • the development conditions such as the development time and the temperature of the development step developer may be any conditions that can remove the unexposed areas. In order to process fine patterns or remove residues between patterns, It is preferable to further develop after the portion has been removed.
  • Rinsing with water may be performed after development.
  • alcohols such as ethanol and isopropyl alcohol
  • esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to water for rinsing treatment.
  • This temperature is preferably in the range of 50 to 180 ° C, and more preferably in the range of 80 to 150 ° C.
  • the time is preferably 5 seconds to several hours.
  • heat drying may be performed in the range of 70 to 150 ° C.
  • the time is preferably 1 minute to several hours.
  • the substrate on which the patterned photosensitive resin film thus obtained is formed is cured at a temperature of 150 ° C. to 450 ° C.
  • This heat treatment is carried out for 5 minutes to 10 hours by selecting the temperature and increasing the temperature stepwise or by selecting a certain temperature range and continuously increasing the temperature.
  • a method of performing heat treatment at 110 ° C. and 250 ° C. for 60 minutes each, a method of linearly raising the temperature from room temperature to 220 ° C. over 2 hours, and the like can be mentioned.
  • the heat treatment is more preferably performed at 150 ° C. or higher.
  • the photosensitive resin composition in the present invention can provide a cured film having excellent adhesion even at low temperature baking of 250 ° C. or lower.
  • the cured film obtained by curing the photosensitive resin composition or photosensitive sheet of the present invention can be used for semiconductor devices and semiconductor electronic components.
  • the semiconductor device referred to in the present invention refers to a device represented by a storage device (memory) or a central processing unit (CPU), in which semiconductor chips are connected by a multilayer wiring called a rewiring layer, and a sealing resin such as epoxy Packaged using.
  • the semiconductor chip refers to a Si wafer having circuit elements.
  • the semiconductor electronic component referred to in the present invention refers to a device (surface acoustic wave filter) for extracting a specific frequency, an inductor, and a conductor.
  • the semiconductor device referred to in the present invention refers to all devices that can function by utilizing the characteristics of semiconductor elements.
  • An electro-optical device and a semiconductor circuit substrate in which a semiconductor element is connected to a substrate, a stack of a plurality of semiconductor elements, and an electronic device including these are all included in the semiconductor device. Further, electronic components such as a multilayer wiring board for connecting semiconductor elements are also included in the semiconductor device.
  • a semiconductor passivation film, a surface protection film of a semiconductor element, an interlayer insulating film between a semiconductor element and a wiring, an interlayer insulating film between a plurality of semiconductor elements, and an interlayer between wiring layers of a multilayer wiring for high-density mounting Although used suitably for uses, such as an insulating film and an insulating layer of an organic electroluminescent element, it is not restricted to this but can be used for various uses.
  • FIG. 1 is an enlarged cross-sectional view of a pad portion of a semiconductor device having bumps.
  • a passivation film 3 is formed on an input / output Al pad 2 in a silicon wafer 1, and a via hole is formed in the passivation film 3.
  • an insulating film 4 formed using the photosensitive resin composition of the present invention is formed thereon, and further a metal film 5 made of Cr, Ti or the like is formed so as to be connected to the Al pad 2. Yes.
  • the pads are insulated from each other.
  • a barrier metal 8 and a solder bump 10 are formed on the insulated pad.
  • a flexible component is introduced into the photosensitive resin composition, since the warpage of the wafer is small, exposure and transportation of the wafer can be performed with high accuracy.
  • polyimide resin and polybenzoxazole resin also have excellent mechanical properties, so stress from the sealing resin can be relaxed even during mounting, preventing damage to the low-k layer (low dielectric constant layer) and high reliability.
  • the semiconductor device can be provided.
  • the photosensitive resin composition of the present invention is applied to the silicon wafer 1 on which the Al pad 2 and the passivation film 3 are formed, and a patterned insulating film 4 is formed through a photolithography process.
  • the metal film 5 is formed by the sputtering method.
  • a metal wiring 6 is formed on the metal film 5 by a plating method.
  • the photosensitive resin composition of the present invention is applied, and an insulating film 7 is formed as a pattern as shown in 2d of FIG. 2 through a photolithography process.
  • a wiring can be further formed on the insulating film 7.
  • rewiring in the case of forming a multilayer wiring structure having two or more layers, by repeating the above process, two or more layers of rewiring were separated by an interlayer insulating film obtained from the photosensitive resin composition of the present invention.
  • a multilayer wiring structure can be formed.
  • the formed insulating film will come into contact with various chemicals multiple times, but since the insulating film obtained from the photosensitive 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. If the insulating film 7 has no pattern formed on 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 as in the present invention in order to obtain high reliability of the semiconductor device.
  • the photosensitive resin composition and photosensitive sheet of the present invention are also suitably used for fan-out wafer level packages (fan-out WLP).
  • the fan-out WLP is provided with an extended portion using a sealing resin such as epoxy resin around the semiconductor chip, rewiring from the electrode on the semiconductor chip to the extended portion, and mounting a solder ball on the extended portion.
  • a sealing resin such as epoxy resin around the semiconductor chip
  • rewiring from the electrode on the semiconductor chip to the extended portion and mounting a solder ball on the extended portion.
  • This is a semiconductor package that secures the necessary number of terminals.
  • wiring is installed so as to straddle the boundary line formed by the main surface of the semiconductor chip and the main surface of the sealing resin.
  • an interlayer insulating film is formed on a base material composed of two or more materials such as a semiconductor chip provided with metal wiring and a sealing resin, and wiring is formed on the interlayer insulating film.
  • 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 substrate composed of two or more materials, and wiring is formed on the interlayer insulating film.
  • the cured film formed by curing the photosensitive resin composition or photosensitive sheet of the present invention has a high adhesion to a semiconductor chip provided with metal wiring, and also has a high adhesion to an epoxy resin or the like on a sealing resin. Therefore, it is suitably used as an interlayer insulating film provided on a substrate composed of two or more materials.
  • a process such as a chip-first method or a RDL-first (Redistribution Layer-first) method is applied to the fan-out WLP.
  • the chip first method as described above, first, semiconductor chips are arranged at arbitrary intervals on the upper surface of a support wafer serving as a support, and the semiconductor chips are sealed with resin to obtain a sealed wafer (pseudo wafer). . Next, the support wafer is separated and removed from the sealing wafer, and a wiring layer is formed on the exposed surface of the sealing wafer. Then, a plurality of device packages are obtained by dividing the sealing wafer between the semiconductor chips.
  • the RDL first method first, a wiring layer is formed on the upper surface of the supporting wafer, and a semiconductor chip is bonded to the wiring layer. Next, the semiconductor chip is sealed with resin to obtain a sealed wafer (pseudo wafer). Thereafter, the support wafer is separated and removed from the sealing wafer including the wiring layer, and the sealing wafer is divided between the semiconductor chips.
  • a semiconductor chip can be bonded while avoiding a defective portion of the wiring layer, so that the yield is easily increased as compared with the chip first method.
  • a method for manufacturing a semiconductor device in the RDL first method will be described with reference to FIG.
  • a barrier metal such as Ti is formed on the support substrate 11 by sputtering, and a Cu seed (seed layer) is further formed thereon by sputtering, and then an electrode pad 12 is formed by plating.
  • the photosensitive resin composition of the present invention is applied, and a patterned insulating film 13 is formed through a photolithography process.
  • step 3c a seed layer is formed again by a sputtering method, and a metal wiring 14 (rewiring layer) is formed by a plating method.
  • step 3e the photosensitive resin composition of the present invention is applied again, and after a photolithography process, a patterned insulating film is formed, and then a Cu post 15 is formed by a plating method.
  • the pitch of the Cu posts is equal to the pitch of the conductive portions of the semiconductor chip. That is, in order to make the rewiring layer multilayer while narrowing the metal wiring pitch, as shown in 3e of FIG.
  • the thickness of the interlayer insulating film is as follows: interlayer insulating film 1> interlayer insulating film 2> interlayer insulating film 3> Interlayer insulating film 4>. That is, a plurality of interlayer insulating films are stacked, a semiconductor chip is disposed substantially parallel to the interlayer insulating film, and the thickness of the interlayer insulating film disposed near the semiconductor chip is the thickness of the interlayer insulating film disposed further away. It will be thinner. Then, in the step 3f, the semiconductor chip 17 is connected through the solder bumps 16 to obtain a semiconductor device by the RDL first method having a multilayer wiring structure.
  • the photosensitive resin composition of the present invention is also suitably used for an organic EL display device.
  • the organic EL display device includes a drive circuit, a planarization layer, a first electrode, an insulating layer, a light emitting layer, and a second electrode on a substrate, and the planarization layer and / or the first electrode on the drive circuit.
  • 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 display device As an example, it has a TFT on a substrate made of glass, various plastics, etc., and a wiring located on a side portion of the TFT and connected to the TFT, and covers unevenness thereon.
  • the planarization layer is provided, and the display element is provided on the planarization layer.
  • the display element and the wiring are connected through a contact hole formed in the planarization layer.
  • FIG. 4 shows a cross-sectional view of an example of a TFT substrate.
  • bottom gate type or top gate type TFTs (thin film transistors) 18 are provided in a matrix, and the TFT insulating layer 20 is formed so as to cover the TFTs 18.
  • a wiring 19 connected to the TFT 18 is provided on the TFT insulating layer 20.
  • a planarizing layer 21 is provided on the TFT insulating layer 20 in a state where the wiring 19 is embedded.
  • a contact hole 24 reaching the wiring 19 is provided in the planarization layer 21.
  • An ITO (transparent electrode) 22 is formed on the planarizing layer 21 while being connected to the wiring 19 through the contact hole 24.
  • the ITO 22 serves as an electrode of a display element (for example, an organic EL element).
  • An insulating layer 25 is formed so as to cover the periphery of the ITO 22.
  • the organic EL element may be a top emission type that emits emitted light from the side opposite to the substrate 23 or a bottom emission type that extracts light from the substrate 23 side. In this manner, an active matrix organic EL display device in which the TFT 18 for driving the organic EL element is connected to each organic EL element is obtained.
  • the insulating layer 20, the planarizing layer 21, and / or the insulating layer 25 are a step of forming a photosensitive resin film made of the resin composition or resin sheet of the present invention, a step of exposing the photosensitive resin film, It can form by the process of developing the exposed photosensitive resin film, and the process of heat-processing the developed photosensitive resin film.
  • An organic EL display device can be obtained from the manufacturing method having these steps.
  • a silicon substrate that is a semiconductor circuit forming substrate manufactured by the chip first method or the RDL first method described above is used as a support substrate using a temporary bonding adhesive, a glass substrate, a film.
  • the wafer processed body is formed by adhering to the above.
  • the non-circuit forming surface (back surface) is polished to obtain a semiconductor circuit forming substrate having a thickness of 1 ⁇ m to 100 ⁇ m.
  • the molecular weight of the resin of component (A) was measured using a GPC (gel permeation chromatography) apparatus Waters 2690-996 (manufactured by Nippon Waters Co., Ltd.), and the developing solvent was N-methyl-2-pyrrolidone (hereinafter referred to as “the developing solvent”).
  • the molecular weight of the Y 2 component in the general formula (1) of the component (A) resin is measured by LC-MS (Q Exactive, Thermo SCIENTIFIC, Inc.) for the diamine monomer containing the Y 2 structure. The molecular weight can be obtained.
  • the sensitivity is 500 mJ / cm 2 or more, or the unexposed part is not completely dissolved and there is a residue C, and C is 300 mJ / cm 2 or more and less than 500 mJ / cm 2 is good B.
  • a sample having a value of less than 300 mJ / cm 2 was regarded as very good A.
  • the release surface was placed on a silicon wafer with a stage temperature of 80 ° C., a roll temperature of 80 ° C., a vacuum of 150 Pa, a sticking speed of 5 mm / sec, and a sticking pressure of 0
  • the film was laminated under the condition of 2 MPa, and the support film was peeled off to obtain a photosensitive resin film. Thereafter, the sensitivity was evaluated as described in (3-1).
  • Adhesion test An adhesion test with a metal material was performed by the following method. ⁇ Preparation of cure film> Copper was sputtered onto a silicon wafer, and a substrate (copper sputter substrate) having a metal material layer formed with a thickness of 200 nm on the surface was prepared. On this substrate, varnish was applied by spin coating using a spinner (Mikasa Co., Ltd.) and then baked at 120 ° C. for 3 minutes using a hot plate (D-SPIN manufactured by Dainippon Screen Mfg. Co., Ltd.). Finally, a pre-baked film having a thickness of 8 ⁇ m was produced.
  • a photosensitive resin sheet was prepared as described in (3-2) Evaluation of sensitivity, and a photosensitive resin film was prepared to have a thickness of 8 ⁇ m. Thereafter, the entire surface of the substrate was exposed at an exposure amount of 1000 mJ / cm 2 using an exposure machine i-line stepper NSR-2005i9C (manufactured by Nikon Corporation). Using a clean oven (CLH-21CD-S manufactured by Koyo Thermo System Co., Ltd.), these membranes were heated at 140 ° C. for 30 minutes under a nitrogen stream (oxygen concentration of 20 ppm or less), then further heated to 220 ° C. Cured for 1 hour to obtain a cured film.
  • ⁇ Adhesion characteristics evaluation> The substrate was divided into two, and each substrate was cut into 10 rows and 10 columns in a grid pattern at intervals of 2 mm using a single blade on the cured film. Of these, one sample substrate was used to count how many of the 100 cells were peeled by peeling with a cellophane tape, and the adhesion characteristics between the metal material and the cured film were evaluated.
  • the other sample substrate was subjected to PCT treatment for 400 hours under a saturated condition of 121 ° C. and 2 atm using a pressure cooker test (PCT) apparatus (HAST CHAMBER EHS-212MD manufactured by Tabais Peeck Co., Ltd.). Thereafter, the above-described peeling test was performed. In any of the substrates, the number of peeled off in the peeling test was A (excellent) when 10 or less, and B (good) when 10 or more and 20 or less, and C (insufficient) when 20 or more.
  • PCT pressure cooker test
  • This film was cut into strips having a width of 1 cm and a length of 9 cm, and using Tensilon RTM-100 (manufactured by Orientec Co., Ltd.) at a room temperature of 23.0 ° C. and a humidity of 45.0% RH, a tensile rate of 50 mm / The sample was pulled in minutes and the elongation at break was measured. The measurement was performed on 10 strips per specimen, and the average value of the top 5 points was obtained from the results. The elongation at break value of 60% or more was designated as A (excellent), 30% or more and less than 60% as B (good), and less than 30% as C (insufficient).
  • 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 desorption condition of ⁇ 27 ° C. and 320 ° C. for 5 minutes, and then a GC-MS apparatus 7890. / 5975C (manufactured by Agilent), GC-MS analysis was performed under the 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 of each component (D) under the same conditions as described above.
  • the obtained value ( ⁇ g) was divided by an area of 5 cm 2 to obtain ⁇ g / cm 2 .
  • the value was divided by 100 times the specific gravity of the alkali-soluble resin (A) multiplied by the film thickness, and the total content of the compound (D) in the cured film was calculated.
  • 1,12-diaminododecane (5.01 g, 0.025 mol), 1,3-bis (3-aminopropyl) tetramethyldisiloxane (1.24 g, 0.0050 mol), PBOM (14. 33 g, 0.044 mol) was added together with 30 g of NMP and reacted at 85 ° C. for 1 hour.
  • 5-norbornene-2,3-dicarboxylic acid anhydride (3.94 g, 0.024 mol) was added as a terminal blocking agent together with 10 g of NMP and reacted at 85 ° C. for 30 minutes.
  • the mixture was cooled to room temperature, acetic acid (26.41 g, 0.50 mol) was added together with 58 g of NMP, and the mixture was stirred at room temperature for 1 hour. After stirring, the solution was poured into 3 L of water to obtain a white precipitate. The precipitate was collected by filtration, washed with water three times, and then dried for 3 days in a ventilator at 50 ° C. to obtain an alkali-soluble resin (A-1) powder.
  • the resin (A-1) had a weight average molecular weight of 33,000 and PDI of 2.1.
  • Synthesis Example 5 Synthesis of Alkali-Soluble Resin (A-5) According to Synthesis Example 1, BAHF (12.82 g, 0.035 mol), 3,3′-diamino-4,4′-dihydroxydiphenyl sulfone (9 .81 g, 0.035 mol), PBOM (31.53 g, 0.088 mol), ED-900 (22.50 g, 0.025 mol, manufactured by HUNTSMAN), 1,3-bis (3-amino) Propyl) tetramethyldisiloxane (1.24 g, 0.0050 mol), 5-norbornene-2,3-dicarboxylic anhydride (3.94 g, 0.024 mol), acetic acid (26.41 g, 0.50 mol) ) And NMP 300 g in the same manner to obtain an alkali-soluble resin (A-5) powder. As a result of evaluation by the above method, the resin (A-5) had a weight average molecular
  • Synthesis Example 7 Synthesis of Alkali-Soluble Resin (A-7) According to Synthesis Example 1, BAHF (27.47 g, 0.075 mol), PBOM (31.53 g, 0.088 mol), RT-1000 (20 0.000 g, 0.020 mol, manufactured by HUNTSMAN), 1,3-bis (3-aminopropyl) tetramethyldisiloxane (1.24 g, 0.0050 mol), 5-norbornene-2,3-dicarboxylic acid The same procedure was performed using acid anhydride (3.94 g, 0.024 mol), acetic acid (26.41 g, 0.50 mol), and 300 g of NMP to obtain an alkali-soluble resin (A-7) powder. As a result of evaluation by the above method, the resin (A-7) had a weight average molecular weight of 44,000 and PDI of 2.2.
  • the solution was poured into 3 liters of water, and the precipitate was collected, washed with pure water three times, and then decompressed to obtain an alkali-soluble resin (A-9).
  • the weight average molecular weight determined by GPC standard polystyrene conversion of (A-9) was 31,600, and the degree of dispersion was 2.0.
  • the resulting resin was cooled to room temperature to obtain a novolak resin (A-10) powder, and as a result of evaluation by the above method, the resin (A-10) had a weight average molecular weight of 3,500 and a PDI of 2 .8 Was Tsu.
  • the precipitate was collected by filtration, washed with water three times, and then dried for 3 days with a ventilator at 50 ° C. to obtain a powder of a closed ring polyimide resin (A-11).
  • the resin (A-11) had a weight average molecular weight of 27,000 and PDI of 2.0.
  • Example 1 will be described below in detail as an example.
  • 10 g of the obtained alkali-soluble resin (A-1) (B-1) 1.5 g of (b-1) photoinitiator (b-1) as a photocrosslinking agent, and (b-2) polymerizability 3.0 g of the following (b-1-2) as an unsaturated compound, and (C) 0.5 g of the following (C-1) is added as a compound having at least an oxygen atom or a sulfur atom or nitrogen atom in the molecule.
  • D 5 g of 3-methoxy-N, N-dimethylpropionamide (D-1) as an organic solvent having a boiling point of 200 ° C.
  • a varnish was prepared by adding 15 g of ethyl lactate (E-1) as a less organic solvent.
  • varnishes according to the compositions shown in Table 1 were prepared in Examples 2 to 21 and Comparative Examples 1 and 2.
  • the characteristics of the produced varnish were measured by the above evaluation method. The obtained results are shown in Table 1.
  • the solvents of Examples 1 to 21 and Comparative Examples 1 and 2 were all prepared with 5 g of 3-methoxy-N, N-dimethylpropionamide (D-1) and 15 g of ethyl lactate (E-1).
  • the photosensitive resin film is produced by distinguishing whether it is produced from a varnish or a sheet.
  • Photoinitiator (b-1-1) 1,2-octanedione-1- [4- (phenylthio) phenyl] -2- (o-benzoyloxime) (OXE02, manufactured by Ciba Specialty Chemicals)
  • E-1 Ethyl lactate Thermal cross-linking agent (F-1): NIKACALAC MX-

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Abstract

L'invention se rapporte à une composition de résine photosensible qui forme un film durci présentant une excellente adhérence à un matériau métallique, en particulier au cuivre même pendant des traitements thermiques à basses températures, tout en ayant un degré d'allongement élevé. Cette composition de résine photosensible est caractérisée en ce qu'elle contient (A) une résine soluble dans les alcalis ayant une unité structurale représentée par la formule générale (1), et (B) un agent de photoréticulation. (Dans la formule générale (1), chacun de X1 et X2 représente un groupe organique ayant une valence de 2 à 10 ; Y1 représente un groupe organique ayant une valence de 2 à 4 ; Y2 représente un groupe organique divalent ayant une structure aliphatique avec 2 atomes de carbone ou plus ; chacun de R1 et R2 représente un atome d'hydrogène ou un groupe organique ayant 1 à 20 atomes de carbone ; chacun de p, q, r, s et t représente un nombre entier conforme à 0 ≤ p ≤ 4, 0 ≤ q ≤ 4, 0 ≤ r ≤ 2, 0 ≤ s ≤ 4 et 0 ≤ t ≤ 4 ; chacun de n1 et n2 représente un nombre entier conforme à 1 ≤ n1 ≤ 500, 1 ≤ n2 ≤ 500 et 0,05 ≤ n1/(n1 + n2) < 1 ; et les unités structurales peuvent être agencées en blocs ou de manière aléatoire.)
PCT/JP2017/030144 2016-08-29 2017-08-23 Composition de résine photosensible, film durci, dispositif d'affichage el organique, composant électronique semi-conducteur, et dispositif à semi-conducteur WO2018043250A1 (fr)

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WO2018225676A1 (fr) * 2017-06-06 2018-12-13 富士フイルム株式会社 Composition de résine photosensible, film durci, stratifié, procédé de production de film durci, dispositif à semi-conducteur et composé
CN109742110A (zh) * 2019-01-04 2019-05-10 京东方科技集团股份有限公司 有机发光显示器及制造方法
WO2020196139A1 (fr) * 2019-03-27 2020-10-01 東レ株式会社 Composition de résine photosensible, feuille de résine photosensible, procédé de production de structure creuse et composant électronique
JP2020196796A (ja) * 2019-05-31 2020-12-10 太陽ホールディングス株式会社 硬化性組成物、ドライフィルムまたはプリプレグ、硬化物、および電子部品
KR20210042049A (ko) * 2018-08-06 2021-04-16 에이치디 마이크로시스템즈 가부시키가이샤 감광성 수지 조성물, 패턴 경화막의 제조 방법, 경화막, 층간 절연막, 커버 코트층, 표면 보호막 및 전자 부품

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TWI656605B (zh) * 2018-06-27 2019-04-11 欣興電子股份有限公司 線路板的製造方法

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JPWO2018225676A1 (ja) * 2017-06-06 2020-04-09 富士フイルム株式会社 感光性樹脂組成物、硬化膜、積層体、硬化膜の製造方法、半導体デバイスおよび化合物
KR20210042049A (ko) * 2018-08-06 2021-04-16 에이치디 마이크로시스템즈 가부시키가이샤 감광성 수지 조성물, 패턴 경화막의 제조 방법, 경화막, 층간 절연막, 커버 코트층, 표면 보호막 및 전자 부품
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CN109742110A (zh) * 2019-01-04 2019-05-10 京东方科技集团股份有限公司 有机发光显示器及制造方法
CN109742110B (zh) * 2019-01-04 2022-07-08 京东方科技集团股份有限公司 有机发光显示器及制造方法
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WO2020196139A1 (fr) * 2019-03-27 2020-10-01 東レ株式会社 Composition de résine photosensible, feuille de résine photosensible, procédé de production de structure creuse et composant électronique
JPWO2020196139A1 (fr) * 2019-03-27 2020-10-01
JP2020196796A (ja) * 2019-05-31 2020-12-10 太陽ホールディングス株式会社 硬化性組成物、ドライフィルムまたはプリプレグ、硬化物、および電子部品
JP7264728B2 (ja) 2019-05-31 2023-04-25 太陽ホールディングス株式会社 硬化性組成物、ドライフィルムまたはプリプレグ、硬化物、および電子部品

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