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WO2020080207A1 - Composition de film isolant photosensible - Google Patents

Composition de film isolant photosensible Download PDF

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Publication number
WO2020080207A1
WO2020080207A1 PCT/JP2019/039734 JP2019039734W WO2020080207A1 WO 2020080207 A1 WO2020080207 A1 WO 2020080207A1 JP 2019039734 W JP2019039734 W JP 2019039734W WO 2020080207 A1 WO2020080207 A1 WO 2020080207A1
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WO
WIPO (PCT)
Prior art keywords
group
photosensitive resin
resin composition
relief pattern
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
PCT/JP2019/039734
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English (en)
Japanese (ja)
Inventor
隼人 服部
拓矢 大橋
友輝 臼井
和宏 澤田
雅久 遠藤
崇洋 坂口
一樹 平佐田
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Nissan Chemical Corp
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Nissan Chemical Corp
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Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to JP2020553100A priority Critical patent/JP7331860B2/ja
Publication of WO2020080207A1 publication Critical patent/WO2020080207A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • 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

Definitions

  • the present invention relates to a photosensitive resin composition, a photosensitive resin film obtained from the composition, a cured relief pattern using the composition, a method for producing the same, and a semiconductor device having the cured relief pattern.
  • a polyimide resin having excellent heat resistance, electrical characteristics, and mechanical characteristics has been used for the insulating material of electronic parts, and the passivation film, surface protection film, and interlayer insulating film of semiconductor devices.
  • these polyimide resins those provided in the form of a photosensitive polyimide precursor easily form a heat-resistant relief pattern coating film by applying the precursor, exposing, developing, and thermally imidizing by curing. be able to.
  • Such a photosensitive polyimide precursor has a feature that it can significantly reduce the process steps as compared with the conventional non-photosensitive polyimide resin.
  • the method of mounting semiconductor devices on a printed wiring board has also changed in order to improve the degree of integration and arithmetic functions, and to reduce the chip size.
  • the polyimide coating directly contacts the solder bumps, such as BGA (ball grid array) and CSP (chip size packaging), which enables higher density mounting. Structures are being used. When forming such a bump structure, the coating is required to have high heat resistance and chemical resistance.
  • Patent Document 1 discloses that a photosensitive material containing a polyimide precursor is introduced by introducing an aliphatic group having an ethylene glycol structure and having 5 to 30 carbon atoms into a part of a side chain of the polyimide precursor. Disclosed is a photosensitive resin composition that improves the transparency when a photosensitive resin composition is formed and further improves the Young's modulus of a cured film after thermosetting.
  • the photosensitive resin composition comprising the polyimide precursor described in Patent Document 1 has a high transparency and gives a cured product having a high Young's modulus after heat curing, but when used in the above-mentioned applications, the dielectric constant or There has been a demand for further reduction of the dielectric loss tangent.
  • the present invention provides a photosensitive resin composition that gives a cured product having a further reduced dielectric constant or dielectric loss tangent, a method for producing a substrate with a cured relief pattern using the photosensitive resin composition, and the cured relief. It is an object to provide a semiconductor device having a pattern.
  • the inventors of the present invention give a low dielectric constant and a low dielectric loss tangent when a photosensitive resin composition is formed by adding a specific isocyanate compound to a polyimide precursor. They have found that a photosensitive resin composition can be obtained, and completed the present invention.
  • the present invention includes the following.
  • the polyimide precursor which has a unit structure represented by, and (B) following general formula (20): [In the formula, R 23 represents a hydrogen atom or a methyl group, R 24 represents an alkylene group having 1 to 5 carbon atoms, which may have a substituent and may be interrupted by an oxygen atom; 25 represents an isocyanate group or a blocked isocyanate group. ] Isocyanate compound represented by A photosensitive resin composition containing.
  • the blocked isocyanate group has the following general formula (21): [In the formula, A represents a residue of a compound for isocyanate blocking selected from the group consisting of alcohol, amine, amide, active methylene compound, nitrogen-containing heteroaryl compound, oxime, ketoxime, and hydroxamic acid ester. ]
  • Z 1 and Z 2 are each independently Hydrogen atom, halogen atom, hydroxy group, mercapto group, carboxy group, cyano group, formyl group, haloformyl group, sulfo group, nitro group, nitroso group, oxo group, thioxy group,
  • An optionally substituted alkyl, alkoxy, or alkylsulfanyl group having 1 to 10 carbon atoms Represents an optionally substituted alkenyl, alkynyl, or alkoxycarbonyl group having 2 to 10 carbon atoms, or an optionally substituted amino, imino, or carbamoyl group
  • Z 1 and Z 2 may be bonded to each other to form a ring which may contain a hetero atom, may have a substituent, or may be condensed, and the ring may be an aromatic ring.
  • a substrate with a cured relief pattern produced by the method described in [6].
  • a semiconductor device comprising a semiconductor element and a cured film provided on an upper portion or a lower portion of the semiconductor element, wherein the cured film is the cured relief pattern described in [7].
  • a photosensitive resin composition giving a cured product having a low dielectric constant and a low dielectric loss tangent a method for producing a cured relief pattern using the photosensitive resin composition, and a semiconductor device having the cured relief pattern can be provided.
  • the photosensitive resin composition of the present invention contains (A) a polyimide precursor, (B) an isocyanate compound, optionally (C) a carboxylic acid compound or an anhydride thereof, and optionally other components. Each component will be described below in order.
  • the (A) polyimide precursor is a resin component contained in the photosensitive resin composition and has a unit structure represented by the following general formula (1).
  • X 1 is a tetravalent organic group
  • Y 1 is a divalent organic group
  • R 1 and R 2 are each independently a monovalent organic group.
  • X 1 is not particularly limited as long as it is a tetravalent organic group, but from the viewpoint of achieving both heat resistance and photosensitivity, it is preferably a tetravalent group having 6 to 40 carbon atoms. And more preferably an aromatic group in which the —COOR 1 group, the —COOR 2 group and the —CONH— group are in the ortho position to each other, or an alicyclic aliphatic group.
  • the tetravalent organic group represented by X 1 is more preferably an organic group containing an aromatic ring and having 6 to 40 carbon atoms.
  • X 1 is a tetravalent organic group represented by the following formula (5) or the following formulas (5-1) to (5-7).
  • the structure of X 1 may be one kind or a combination of two or more kinds.
  • Y 1 is not limited as long as it is a divalent organic group having 6 to 40 carbon atoms, but Y 1 may be substituted from the viewpoint of achieving both heat resistance and photosensitivity.
  • a cyclic organic group having 1 to 4 aromatic rings or aliphatic rings, or an aliphatic group having no cyclic structure or a siloxane group is preferable.
  • Y 1 is a structure represented by the following general formula (6), the following general formula (7) or the following formula (8).
  • each A independently represents a methyl group (—CH 3 ), an ethyl group (—C 2 H 5 ), a propyl group (—C 3 H 7 ), or a butyl group (—C 4 H 9 ).
  • the structure of Y 1 may be one kind or a combination of two or more kinds.
  • R 1 and R 2 are not particularly limited as long as they are independently monovalent organic groups.
  • R 1 and R 2 are each independently a monovalent aliphatic group having 1 to 30 carbon atoms or 5 to 22 carbon atoms, a cycloaliphatic group, an aromatic group and an aliphatic group bonded to each other. Or a group in which these groups are substituted with a halogen atom, a nitro group, an amino group, a cyano group, a methoxy group, an acetoxy group or the like.
  • Typical halogen atoms are F, Cl, Br and I.
  • R 1 and R 2 are each independently the following general formula (2):
  • R 3 , R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, and m is an integer of 1 to 10. * is , Which is a binding site for the carboxylic acid present in the polyamic acid main chain of the general formula (1).) It is preferable that
  • R 1 and R 2 are each independently the following general formula (3):
  • R 6 is a monovalent group selected from an alkyl group having 1 to 30 carbon atoms. * Is the same as the above.) A monovalent organic group represented by may be included.
  • Each of R 1 and R 2 in the general formula (1) may be one kind or a combination of two or more kinds, but is preferably a combination of three kinds or less, preferably a combination of two kinds, and most preferably 1 It is a seed.
  • the monovalent organic group represented by the general formula (2) with respect to all of R 1 and R 2 and the general formula from the viewpoints of the photosensitivity and mechanical properties of the photosensitive resin composition.
  • the total proportion of monovalent organic groups represented by (3) is preferably 80 mol% or more, preferably 90 mol% or more, and preferably 100 mol%.
  • the ratio of the total of the monovalent organic groups represented by the above general formula (2) to all R 1 and R 2 from the viewpoint of the photosensitive properties and mechanical properties of the photosensitive resin composition Is preferably 80 mol% or more, preferably 90 mol% or more, and preferably 100 mol%.
  • R 3 in the above general formula (2) is not limited as long as it is a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, but from the viewpoint of the photosensitive characteristics of the photosensitive resin composition, R 3 is a hydrogen atom or methyl. It is preferably a group.
  • R 4 and R 5 in the above general formula (2) are not limited as long as they are independently hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms. From the viewpoint, it is preferably a hydrogen atom.
  • M in the general formula (2) is an integer of 1 or more and 10 or less, preferably 2 or more and 4 or less from the viewpoint of photosensitivity.
  • R 6 in the general formula (3) is not limited as long as it is a monovalent organic group selected from alkyl groups having 1 to 30 carbon atoms.
  • An alkyl group having 5 to 30 carbon atoms is preferable, an alkyl group having 8 to 30 carbon atoms is preferable, an alkyl group having 9 to 30 carbon atoms is preferable, and an alkyl group having 10 to 30 carbon atoms is preferable.
  • an alkyl group having 11 to 30 carbon atoms is more preferable, and an alkyl group having 17 to 30 carbon atoms is further preferable. It may have a branched structure or a cyclic structure as well as a linear structure.
  • R 6 in the above general formula (3) is preferably an alkyl group having 5 to 30 carbon atoms, an alkyl group having 8 to 30 carbon atoms, and an alkyl group having 9 to 30 carbon atoms, An alkyl group having 10 to 30 carbon atoms is preferable, an alkyl group having 11 to 30 carbon atoms is more preferable, and an alkyl group having 17 to 30 carbon atoms is further preferable.
  • R 6 is represented by the following formula (4):
  • Z 1 is hydrogen or an alkyl group having 1 to 14 carbon atoms
  • Z 2 is an alkyl group having 1 to 14 carbon atoms
  • Z 3 is an alkyl group having 1 to 14 carbon atoms
  • Z 1 , Z 2 and Z 3 may be the same or different from each other, The total number of carbon atoms of Z 1 , Z 2 and Z 3 is 4 or more. ) Is preferable.
  • Z 1 is hydrogen.
  • Z 1 , Z 2 and Z 3 are preferably alkyl groups having 2 to 12 carbon atoms, and more preferably alkyl groups having 2 to 10 carbon atoms.
  • the total number of carbon atoms of Z 1 , Z 2 and Z 3 is preferably 5 or more, more preferably 6 or more, preferably 10 or more, preferably 12 or more, and 14 or more. Preferably, it is preferably 15 or more, more preferably 16 or more.
  • the total number of carbon atoms of Z 1 , Z 2 and Z 3 is preferably 6 or more and 20 or less.
  • the upper limit of the total number of carbon atoms of Z 1 , Z 2 and Z 3 is preferably 28.
  • R 6 may be selected from the following formulas (3-1) to (3-7).
  • R 6 is preferably selected from the above formulas (3-1) to (3-7).
  • the polyimide precursor (A) is converted into polyimide by subjecting it to a heat cyclization treatment.
  • the polyimide precursor represented by the general formula (1) in the present embodiment includes, for example, a tetracarboxylic dianhydride containing a tetravalent organic group X 1 having 6 to 40 carbon atoms, and (a) the above.
  • a partially esterified tetracarboxylic acid (hereinafter, also referred to as an acid / ester form) is prepared by reacting the resulting alcohols, and then the above-mentioned divalent organic group Y 1 having 6 to 40 carbon atoms is added. It is obtained by polycondensation with the diamines containing it.
  • examples of the tetracarboxylic acid dianhydride containing a tetravalent organic group X 1 having 6 to 40 carbon atoms include pyromellitic dianhydride, diphenyl ether-3,3 ′, 4,4′-tetracarboxylic acid.
  • (a) alcohols having a structure represented by the general formula (2) include, for example, 2-acryloyloxyethyl alcohol, 1-acryloyloxy-3-propyl alcohol, methylol vinyl ketone, and 2 -Hydroxyethyl vinyl ketone, 2-hydroxy-3-methoxypropyl acrylate, 2-hydroxy-3-butoxypropyl acrylate, 2-hydroxy-3-butoxypropyl acrylate, 2-methacryloyloxyethyl alcohol, 1-methacryloyloxy-3- Propyl alcohol, 2-hydroxy-3-methoxypropyl methacrylate, 2-hydroxy-3-butoxypropyl methacrylate, 2-hydroxy-3-butoxypropyl methacrylate, 2-hydroxyethylmethac Mention may be made of the rate, and the like.
  • Alcohols having the structures of the above formulas (3-1) to (3-6) may be used.
  • the following commercial products may be used.
  • the total content of the component (a) and the component (b) in the photosensitive resin composition is preferably 80 mol% or more based on the total content of R 1 and R 2 in the general formula (1).
  • the content of the component (b) is preferably 1 mol% to 90 mol% with respect to the total content of R 1 and R 2 .
  • the above tetracarboxylic dianhydride and the above alcohols are stirred, dissolved and mixed in the reaction solvent at a reaction temperature of 0 to 100 ° C. for 10 to 40 hours in the presence of a basic catalyst such as pyridine.
  • a basic catalyst such as pyridine.
  • the reaction solvent is preferably one that dissolves the acid / ester form and a polyimide precursor which is a polycondensation product of the acid / ester form and diamines.
  • a polyimide precursor which is a polycondensation product of the acid / ester form and diamines.
  • a known dehydration-condensation agent such as dicyclohexylcarbodiimide, 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, to the above acid / ester (typically a solution in the above reaction solvent) under ice cooling.
  • 1,1-Carbonyldioxy-di-1,2,3-benzotriazole, N, N'-disuccinimidyl carbonate, N, N'-diisopropylcarbodiimide, etc. are added and mixed to form an acid / ester compound as a polyacid.
  • a diamine containing a divalent organic group Y 1 having 6 to 40 carbon atoms which is separately dissolved or dispersed in a solvent, is added dropwise to the mixture, and polycondensation is carried out. It is possible to obtain a polyimide precursor that can be used in.
  • diamines containing a divalent organic group Y 1 having 6 to 40 carbon atoms include, for example, p-phenylenediamine, m-phenylenediamine, 4,4-diaminodiphenyl ether, 3,4′-diaminodiphenyl ether, 3,3 '-Diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminobiphenyl, 3,4'-diaminobiphenyl, 3,3'-diaminobiphenyl, 4,4'-diamin
  • the diamines used in the present application are not limited to these.
  • diaminosiloxanes such as 1,3-bis (3-aminopropyl) tetramethyldisiloxane and 1,3-bis (3-aminopropyl) tetraphenyldisiloxane can also be copolymerized.
  • the water-absorbing by-product of the dehydration condensation agent coexisting in the reaction solution is filtered off as necessary, and then water, an aliphatic lower alcohol, or a poor solvent such as a mixed solution thereof is used.
  • a polymer precursor that can be used in the embodiment by pouring into a reaction solution to precipitate a polymer component, and further repeating redissolution and reprecipitation precipitation operations to purify the polymer and perform vacuum drying. Isolate the body.
  • a solution of this polymer may be passed through a column packed by swelling an anion and / or cation exchange resin with a suitable organic solvent to remove ionic impurities.
  • the molecular weight of the (A) polyimide precursor is preferably 5,000 to 150,000, and more preferably 7,000 to 50,000, as measured by polystyrene conversion weight average molecular weight by gel permeation chromatography. Is more preferable.
  • weight average molecular weight is 5,000 or more, mechanical properties are good, which is preferable.
  • weight average molecular weight is 150,000 or less, dispersibility in a developing solution and resolution performance of a relief pattern are good. It is preferable because it is good.
  • the (B) isocyanate compound is represented by the following general formula (20).
  • R 23 represents a hydrogen atom or a methyl group
  • R 24 represents an alkylene group having 1 to 5 carbon atoms, which may have a substituent and may be interrupted by an oxygen atom
  • 25 represents an isocyanate group or a blocked isocyanate group.
  • R 24 is not particularly limited as long as it has a substituent and is an alkylene group having 1 to 5 carbon atoms which may be interrupted by an oxygen atom.
  • alkylene group having 1 to 5 carbon atoms include a substituted or unsubstituted methylene group, ethylene group, propylene group, butylene group and the like.
  • alkylene group interrupted by an oxygen atom include —CH 2 —O—CH 2 —, —C 2 H 4 —O—CH 2 —, —CH 2 —O—C 2 H 4 — and the like. .
  • substituents examples include a halogen atom, an acryloyl group, a methacryloyl group, a nitro group, an amino group, a cyano group, a methoxy group and an acetoxy group, and an acryloyl group and a methacryloyl group are preferable.
  • R 25 represents an isocyanate group or a blocked isocyanate group.
  • the isocyanate group means a group represented by —NCO
  • the blocked isocyanate group means a group in which an isocyanate group is blocked by a heat-eliminating protective group, that is, an isocyanate blocking compound (blocking agent) is added to the isocyanate group. The reacted group.
  • An isocyanate group blocking agent generally reacts with an isocyanate group to prevent a reaction with a functional group in another molecule (for example, an acid functional group) at room temperature, but desorbs at a high temperature to release an isocyanate group. Regenerate and allow subsequent reactions (eg with acid functional groups).
  • the blocking agent include alcohols such as methanol, ethanol, isopropanol, n-butanol, 2-ethoxyhexanol, 2-N, N-dimethylaminoethanol, 2-ethoxyethanol, cyclohexanol, phenol and o-nitrophenol.
  • Phenols such as p-chlorophenol, o-cresol, m-cresol, p-cresol, lactams such as ⁇ -caprolactam, acetone oxime, methyl ethyl ketone oxime, methyl isobutyl ketone oxime, cyclohexanone oxime, acetophenone oxime, benzophenone oxime, etc.
  • heteroaryl compounds such as oximes, amines, amides, pyrazole, 3,5-dimethylpyrazole, 3-methylpyrazole, dodecanethiol, benzene Thiols such as thiol, malonic acid diester, acetoacetic acid ester, malonic acid dinitrile, acetylacetone, methylenedisulfone, dibenzoylmethane, dipivaloylmethane, active methylene compounds such as acetonedicarboxylic acid diester, and hydroxamic acid ester.
  • the blocking agent is volatile and advantageously evaporates from the composition after desorption.
  • Blocked isocyanate groups for example, [In the formula, A represents a residue of a compound for isocyanate blocking selected from the group consisting of alcohol, amine, amide, active methylene compound, nitrogen-containing heteroaryl compound, oxime, ketoxime, and hydroxamic acid ester. ] It is represented by.
  • isocyanate compound represented by the above formula (20) examples include isocyanate-containing (meth) acrylates such as 2-isocyanate ethyl methacrylate and 2-isocyanate ethyl acrylate, and methyl ethyl ketone oxime, ⁇ -caprolactam, ⁇ -caprolactam.
  • isocyanate-containing (meth) acrylates such as 2-isocyanate ethyl methacrylate and 2-isocyanate ethyl acrylate, and methyl ethyl ketone oxime, ⁇ -caprolactam, ⁇ -caprolactam.
  • examples include compounds to which a blocking agent such as 3,5-dimethylpyrazole, diethyl malonate, ethanol, isopropanol, n-butanol, and 1-methoxy-2-propanol is added.
  • these compounds may be used individually or may be used in combination of 2 or more type.
  • the (B) isocyanate compound can be synthesized by a known method, or the following commercially available products can be used.
  • Karens AOI (2-Isocyanatoethyl acrylate, a registered trademark of Showa Denko KK)
  • Karenz AOI-BM (2- (O- [1'-methylpropylideneamino] carboxamino) ethyl acrylate, registered trademark manufactured by Showa Denko KK)
  • Karenz AOI-VM (2-Isocyanatoethyl acrylate, a registered trademark of Showa Denko KK)
  • Karens MOI (2-Isocyanatoethyl methacrylate, a registered trademark of Showa Denko KK)
  • Karenz MOI-BM (2- (O- [1′-methylpropylideneamino] carboxyamino) ethyl methacrylate, a registered trademark of Showa Denko KK)
  • an isocyanate compound having a blocked isocyanate group having the following structure can be used.
  • the amount of the (B) isocyanate compound in the photosensitive resin composition according to the present invention is usually 1 part by mass to 50 parts by mass with respect to 100 parts by mass of the polyimide precursor (A).
  • the photosensitive resin composition of the present invention may further contain (C) a carboxylic acid compound represented by the following general formula (30) or an anhydride thereof, if desired.
  • Z 1 and Z 2 are each independently Hydrogen atom, halogen atom, hydroxy group, mercapto group, carboxy group, cyano group, formyl group, haloformyl group, sulfo group, nitro group, nitroso group, oxo group, thioxy group,
  • An optionally substituted alkyl, alkoxy, or alkylsulfanyl group having 1 to 10 carbon atoms Represents an optionally substituted alkenyl, alkynyl, or alkoxycarbonyl group having 2 to 10 carbon atoms, or an optionally substituted amino, imino, or carbamoyl group
  • Z 1 and Z 2 may be bonded to each other to form a ring which may contain a hetero atom, may have a substituent, or may be condensed, and the ring may be an aromatic ring.
  • the carboxylic acid compound or its anhydride (C) is a carboxylic acid compound represented by the following general formula (31) or its anhydride.
  • R 33 to R 36 are each independently Hydrogen atom, halogen atom, hydroxy group, mercapto group, carboxy group, cyano group, formyl group, haloformyl group, Sulfo group, nitro group, nitroso group, oxo group, thioxy group,
  • An optionally substituted alkyl, alkoxy, or alkylsulfanyl group having 1 to 6 carbon atoms Represents an optionally substituted alkenyl, alkynyl, or alkoxycarbonyl group having 2 to 6 carbon atoms, or an optionally substituted amino, imino, or carbamoyl group
  • R 33 and R 34 , R 34 and R 35 , or R 35 and R 36 may be bonded to each other to contain a hetero atom, may have a substituent, or may be a condensed ring. May be formed.
  • alkyl group examples include straight-chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group (amyl group), hexyl group, heptyl group, octyl group, nonyl group and decyl group.
  • Isopropyl group isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group, sec-isoamyl group, isohexyl group, neohexyl group, 4-methylhexyl group, 5-methyl Hexyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl group, 4-ethylhexyl group, 2-ethylpentyl group, heptan-3-yl group, heptan-4-yl group, 4-methylhexane-2- Yl group, 3-methylhexane-3-yl group, 2,3-dimethylpentan-2-yl group, 2,4-dimethyl Tan-2-yl group, 4,4-dimethylpentan-2-yl group, 6-methylheptyl group, 2-ethy
  • alkoxy, alkylsulfanyl group, and alkoxycarbonyl group include groups in which -O-, -S-, and -COO- are respectively bonded to the above alkyl group.
  • alkenyl group examples include ethenyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group and 3- Examples include a pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 1-heptenyl group, 2-heptenyl group, 5-heptenyl group, 1-octenyl group, 3-octenyl group, and 5-octenyl group. .
  • alkynyl group examples include an acetylenyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentethyl group, a 2-pentethyl group, and a 3-pentynyl group.
  • Pentethyl group 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 1-heptynyl group, 2-heptynyl group, 5-heptynyl group, 1-octynyl group, 3-octynyl group, 5-octynyl group and the like can be mentioned. .
  • ring in which Z 1 and Z 2 are bonded to each other to form a ring which may contain a hetero atom may have a substituent, and may be condensed, and R 33
  • R 34 , R 34 and R 35 , or R 35 and R 36 are bonded to each other to form a ring which may contain a hetero atom, may have a substituent, or may be condensed.
  • substituents examples include a halogen atom, hydroxy group, mercapto group, carboxy group, cyano group, formyl group, haloformyl group, sulfo group, amino group, nitro group, nitroso group, oxo group, thioxy group, and 1 carbon atom. And an alkyl or haloalkyl group having 1 to 10 carbon atoms and an alkoxy or haloalkoxy group having 1 to 10 carbon atoms.
  • Z 1 and Z 2 in the general formula (2) are a hydrogen atom or an optionally substituted alkyl group having 1 to 10 carbon atoms.
  • the carboxylic acid compounds exemplified above may be acid anhydrides.
  • the amount of the carboxylic acid compound or its anhydride (C) in the photosensitive resin composition according to the present invention is usually 0.1 parts by mass to 10 parts by mass with respect to 100 parts by mass of the polyimide precursor (A). .
  • the photosensitive resin composition may further contain components other than the above-mentioned components (A) to (C).
  • other components include a photopolymerization initiator, a crosslinkable compound, a solvent, a resin component other than the (A) polyimide precursor, a sensitizer, an adhesion aid, a thermal polymerization inhibitor, an azole compound, and a hindered phenol. Examples thereof include compounds and fillers.
  • the photosensitive resin composition of the present invention may contain a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited as long as it is a compound having absorption in the light source used during photocuring, and examples thereof include tert-butylperoxy-iso-butyrate and 2,5-dimethyl-2,5-bis (benzoyl).
  • the photopolymerization initiator is available as a commercially available product, for example, IRGACURE [registered trademark] 651, 184, 2959, 127, 907, 369, 379EG, 819, 819DW, and 1800, 1870, 784, OXE01, OXE02, 250, 1173, MBF, TPO, 4265, TPO (manufactured by BASF), KAYACURE [registered trademark] DETX, MBP, and the like.
  • DMBI EPA, OA (all manufactured by Nippon Kayaku Co., Ltd.), VICURE-10, all 55 (all manufactured by STAUFFER Co.
  • the blending amount of the photopolymerization initiator is usually 0.1 parts by mass to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor, and preferably 0.5 parts by mass to 15 parts by mass from the viewpoint of photosensitivity. It is a department.
  • the photopolymerization initiator is blended in an amount of 0.1 part by mass or more with respect to 100 parts by mass of the (A) polyimide precursor, the photosensitivity of the photosensitive resin composition is likely to be improved, while in the case of blending 20 parts by mass or less. In particular, the thick film curability of the photosensitive resin composition is easily improved.
  • a monomer (crosslinking compound) other than the (B) isocyanate compound having a photopolymerizable unsaturated bond is optionally mixed with the photosensitive resin composition.
  • a crosslinkable compound a (meth) acrylic compound that undergoes a radical polymerization reaction with a photopolymerization initiator is preferable, and is not particularly limited to, but includes, for example, diethylene glycol dimethacrylate and tetraethylene glycol dimethacrylate.
  • the amount of the cross-linking compound (B) other than the isocyanate compound to be blended is preferably 1 part by mass to 100 parts by mass, more preferably 1 part by mass to 50 parts by mass, relative to 100 parts by mass of the (A) polyimide precursor. is there.
  • thermal crosslinking agent examples include hexamethoxymethylmelamine, tetramethoxymethylglycoluril, tetramethoxymethylbenzoguanamine, 1,3,4,6-tetrakis (methoxymethyl) glycoluril, 1,3,4,6-tetrakis (butoxymethyl).
  • examples thereof include 3,3-tetrakis (methoxymethyl) urea.
  • the filler include inorganic fillers, and specific examples include sol such as silica, aluminum nitride, boron nitride, zirconia, and alumina.
  • an organic solvent from the viewpoint of solubility in the (A) polyimide precursor.
  • the solvent is, for example, in the range of 30 parts by mass to 1500 parts by mass, preferably 100 parts by mass, based on 100 parts by mass of the (A) polyimide precursor, depending on the desired coating film thickness and viscosity of the photosensitive resin composition. It can be used in the range of up to 1000 parts by mass.
  • the photosensitive resin composition may further contain a resin component other than the (A) polyimide precursor.
  • a resin component other than the (A) polyimide precursor examples include polyimide, polyoxazole, polyoxazole precursor, phenol resin, polyamide, epoxy resin, siloxane resin, acrylic resin and the like.
  • the blending amount of these resin components is preferably in the range of 0.01 to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
  • the photosensitive resin composition may optionally contain a sensitizer in order to improve photosensitivity.
  • a sensitizer examples include Michler's ketone, 4,4′-bis (diethylamino) benzophenone, 2,5-bis (4′-diethylaminobenzal) cyclopentane, 2,6-bis (4′-diethylaminobenzal ) Cyclohexanone, 2,6-bis (4'-diethylaminobenzal) -4-methylcyclohexanone, 4,4'-bis (dimethylamino) chalcone, 4,4'-bis (diethylamino) chalcone, p-dimethylaminocinna Millidene indanone, p-dimethylaminobenzylidene indanone, 2- (p-dimethylaminophenylbiphenylene) -benzothiazole, 2- (p-dimethylaminophenylvinylene) benzothiazole,
  • the compounding amount of the sensitizer is preferably 0.1 part by mass to 25 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
  • an adhesion aid in order to improve the adhesiveness between the film formed using the photosensitive resin composition and the substrate, an adhesion aid can be optionally added to the photosensitive resin composition.
  • the adhesion aid include ⁇ -aminopropyldimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, 3-methacryloxypropyldimethoxymethylsilane, 3-methacryloxypropyltrimethoxysilane, dimethoxymethyl-3-piperidinopropylsilane, diethoxy-3-glycidoxypropylmethylsilane, N- (3-diethoxymethylsilylpropyl ) Succinimide, N- [3- (triethoxysilyl) propyl] phthalamic acid, benzophen
  • adhesion aids it is more preferable to use a silane coupling agent from the viewpoint of adhesive strength.
  • the amount of the adhesion aid compounded is preferably in the range of 0.5 to 25 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
  • a thermal polymerization inhibitor may be optionally added in order to improve the stability of the viscosity and photosensitivity of the photosensitive resin composition during storage, particularly in the state of a solution containing a solvent.
  • the thermal polymerization inhibitor include hydroquinone, N-nitrosodiphenylamine, p-tert-butylcatechol, phenothiazine, N-phenylnaphthylamine, ethylenediaminetetraacetic acid, 1,2-cyclohexanediaminetetraacetic acid, glycol etherdiaminetetraacetic acid, 2 , 6-di-tert-butyl-p-methylphenol, 5-nitroso-8-hydroxyquinoline, 1-nitroso-2-naphthol, 2-nitroso-1-naphthol, 2-nitroso-5- (N-ethyl-) N-sulfopropylamino) phenol, N-nitroso-N-phenylhydroxylamine am
  • the blending amount of the thermal polymerization inhibitor is preferably in the range of 0.005 parts by mass to 12 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor.
  • an azole compound can be optionally added to the photosensitive resin composition in order to suppress discoloration of the substrate.
  • the azole compound include 1H-triazole, 5-methyl-1H-triazole, 5-ethyl-1H-triazole, 4,5-dimethyl-1H-triazole, 5-phenyl-1H-triazole and 4-t-butyl.
  • the compounding amount of the azole compound is preferably 0.1 part by mass to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor, and is 0.5 part by mass to 5 parts by mass from the viewpoint of photosensitivity. More preferably.
  • the compounding amount of the azole compound with respect to 100 parts by mass of the (A) polyimide precursor is 0.1 parts by mass or more, when the photosensitive resin composition is formed on copper or a copper alloy, copper or the copper alloy is formed. Discoloration of the surface is suppressed, while when it is 20 parts by mass or less, the photosensitivity is excellent, which is preferable.
  • a hindered phenol compound can be optionally added to the photosensitive resin composition in order to suppress discoloration on copper.
  • the hindered phenol compound include 2,6-di-t-butyl-4-methylphenol, 2,5-di-t-butyl-hydroquinone, octadecyl-3- (3,5-di-t-butyl).
  • 1,3,5-tris (4-t-butyl-3-hydroxy-2,6-dimethylbenzyl) -1,3,5-triazine-2,4,6- (1H, 3H, 5H ) -Trione is particularly preferred.
  • the content of the hindered phenol compound is preferably 0.1 part by mass to 20 parts by mass with respect to 100 parts by mass of the (A) polyimide precursor, and 0.5 part by mass to 10 parts by mass from the viewpoint of photosensitivity. It is more preferably part.
  • the blending amount of the hindered phenol compound with respect to 100 parts by mass of the (A) polyimide precursor is 0.1 parts by mass or more, for example, when the photosensitive resin composition is formed on copper or a copper alloy, copper or copper is used. Discoloration / corrosion of the alloy is prevented, while when it is 20 parts by mass or less, the photosensitivity is excellent, which is preferable.
  • Method for producing cured relief pattern In the embodiment, the following steps are performed: (1) a step of applying a photosensitive resin composition according to the present invention onto a substrate to form a photosensitive resin layer on the substrate; (2) exposing the photosensitive resin layer to light, (3) a step of developing the photosensitive resin layer after the exposure to form a relief pattern, (4) It is possible to provide a method for producing a substrate with a cured relief pattern, including the step of forming a cured relief pattern by heating the relief pattern.
  • Step of applying the photosensitive resin composition according to the present invention onto a substrate to form a photosensitive resin layer on the substrate the photosensitive resin composition according to the present invention is applied onto a substrate.
  • the photosensitive resin layer is formed by applying and then drying it if necessary.
  • a coating method a method which has been conventionally used for coating a photosensitive resin composition, for example, a spin coater, a bar coater, a blade coater, a curtain coater, a screen printing machine, or a spray coater is used. The method etc. can be used.
  • the coating film made of the photosensitive resin composition can be dried, and as the drying method, for example, methods such as air drying, heat drying using an oven or a hot plate, and vacuum drying are used. Further, it is desirable that the coating film is dried under the condition that the (A) polyimide precursor in the photosensitive resin composition is not imidized. Specifically, when air drying or heat drying is performed, the drying can be performed at 20 ° C. to 200 ° C. for 1 minute to 1 hour. As described above, the photosensitive resin layer can be formed on the substrate.
  • Step of exposing the photosensitive resin layer the photosensitive resin layer formed in the step (1) is exposed to a photomask having a pattern by using an exposure device such as a contact aligner, a mirror projection, and a stepper.
  • exposure is performed by an ultraviolet light source or the like via a reticle or directly.
  • the light source used for the exposure include g-line, h-line, i-line, ghi-line broadband, and KrF excimer laser.
  • the exposure dose is preferably 25 mJ / cm 2 to 1000 mJ / cm 2 .
  • a post-exposure bake (PEB) and / or a pre-development bake may be performed at an arbitrary combination of temperature and time, if necessary.
  • the baking conditions are preferably such that the temperature is from 50 ° C. to 200 ° C. and the time is preferably from 10 seconds to 600 seconds, as long as the characteristics of the photosensitive resin composition are not impaired. Not limited to
  • Step of developing the exposed photosensitive resin layer to form a relief pattern the unexposed portion of the exposed photosensitive resin layer is removed by development.
  • a developing method for developing the photosensitive resin layer after exposure any of conventionally known photoresist developing methods, for example, a rotary spray method, a paddle method, a dipping method involving ultrasonic treatment, etc. can be selected. The method can be selected and used.
  • post-development baking may be performed at an arbitrary combination of temperature and time, if necessary.
  • Examples of the developer used in the development include N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N, N-dimethylacetamide, cyclopentanone, cyclohexanone, ⁇ -butyrolactone, ⁇ -acetyl- ⁇ -Butyrolactone and the like are preferred. Further, each solvent may be used in combination of two or more kinds, for example, several kinds.
  • Step of heating the relief pattern to form a substrate with a cured relief pattern the relief pattern obtained by the development is heated to volatilize the photosensitive component, and (A) the polyimide precursor. Is converted into a cured relief pattern made of polyimide.
  • the method for heat curing various methods such as a method using a hot plate, a method using an oven, and a method using a temperature rising oven capable of setting a temperature program can be selected.
  • the heating can be performed, for example, at 130 ° C. to 250 ° C. for 30 minutes to 5 hours.
  • Air may be used as the atmospheric gas at the time of heat curing, and an inert gas such as nitrogen or argon may be used.
  • semiconductor device having a cured relief pattern obtained by the method for producing a cured relief pattern described above. Therefore, it is possible to provide a semiconductor device having a base material that is a semiconductor element and a cured relief pattern of polyimide formed on the base material by the above-described cured relief pattern manufacturing method.
  • the present invention can also be applied to a method of manufacturing a semiconductor device that uses a semiconductor element as a base material and includes the method of manufacturing a cured relief pattern described above as part of the process.
  • a semiconductor device is a semiconductor device having a cured relief pattern formed by the above-described method for producing a cured relief pattern, having a surface protective film, an interlayer insulating film, an insulating film for rewiring, a protective film for a flip chip device, or a bump structure. Can be manufactured by combining it with a known semiconductor device manufacturing method.
  • a display device including a display element and a cured film provided on the display element, wherein the cured film has the above-mentioned cured relief pattern.
  • the cured relief pattern may be laminated in direct contact with the display element, or may be laminated with another layer interposed therebetween.
  • examples of the cured film include a surface protective film for a TFT liquid crystal display element and a color filter element, an insulating film, and a flattening film, a projection for an MVA type liquid crystal display device, and a partition for an organic EL element cathode.
  • the photosensitive resin composition of the present invention is useful not only for application to the semiconductor device as described above but also for applications such as interlayer insulation of multilayer circuits, cover coat of flexible copper clad board, solder resist film, and liquid crystal alignment film. Is.
  • the weight average molecular weights shown in the following synthesis examples of the present specification are results of measurement by gel permeation chromatography (hereinafter abbreviated as GPC in the present specification).
  • GPC gel permeation chromatography
  • the 1 H-NMR spectrum was measured by JNM-ECX500 (500 MHz, manufactured by JEOL Ltd.).
  • the obtained reaction mixture was added to 1500 g of methanol (Kanto Chemical Co., Inc., special grade) to form a precipitate composed of a crude polymer.
  • the supernatant was decanted to separate the crude polymer, which was dissolved in 150.0 g of N-methyl-2-pyrrolidinone to obtain a crude polymer solution.
  • the obtained crude polymer solution was dropped into 2250 g of water to precipitate a polymer, and the obtained precipitate was separated by filtration, washed twice with 600 g of methanol, and vacuum dried to obtain a powdery polymer (2). Obtained.
  • the molecular weight of the polymer (2) was measured by GPC (standard polystyrene conversion), the weight average molecular weight (Mw) was 8,016. The yield was 73.6%.
  • This reaction product has a repeating unit structure represented by the following formula (2).
  • Example 1 28.5714 g of the polymer obtained in Preparation Example 2, IRGACURE [registered trademark] OXE01 (manufactured by BASF, photopolymerization initiator) 1.71 g, AOI-BM (manufactured by Showa Denko KK, 2- (O- [1 ' -Methylpropylideneamino] carboxyamino) ethyl acrylate) 8.57 g, KBM-5103 (manufactured by Shin-Etsu Chemical Co., Ltd., 3-acryloxypropyltrimethoxysilane) 0.43 g, IRGANOX [registered trademark] 3114 (manufactured by BASF) , Hindered phenol-based antioxidant) 0.43 g and phthalic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 0.28 g were dissolved in cyclohexanone 48.00 g and ethyl
  • the relative permittivity and dielectric loss tangent at 1 GHz were calculated by the perturbation type cavity resonator method (apparatus: TMR-1A, manufactured by Keycom Co., Ltd.).
  • the details of the measuring method are as follows.
  • Example 1 using the isocyanate compound according to the present invention has a dielectric constant substantially equal to that of Comparative Example 1 using dimethacrylate and Comparative Example 2 using diacrylate, but the dielectric loss tangent is significantly reduced. ing.
  • the photosensitive resin composition according to the present invention provides a cured product having high transparency, high Young's modulus after heat curing, and reduced dielectric constant and dielectric loss tangent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne : une composition de résine photosensible qui permet d'obtenir un corps durci dont la constante diélectrique et la tangente de perte diélectrique sont basses ; un procédé qui emploie cette composition de résine photosensible pour produire un substrat doté d'un motif en relief durci ; et un dispositif à semi-conducteur qui est pourvu de ce motif en relief durci. L'invention concerne une composition de résine photosensible qui contient : (A) un précurseur de polyimide qui possède une structure unitaire représentée par la formule générale (1) (dans laquelle X1 représente un groupe organique tétravalent ; Y1 représente un groupe organique divalent ; et R1 et R2 représentent chacun indépendamment un groupe organique monovalent) ; et (B) un composé isocyanate représenté par la formule générale (20) (dans laquelle R23 représente un atome d'hydrogène ou un groupe méthyle ; R24 représente un groupe alkylène ; et R25 représente un groupe isocyanate ou un groupe isocyanate bloqué).
PCT/JP2019/039734 2018-10-15 2019-10-09 Composition de film isolant photosensible Ceased WO2020080207A1 (fr)

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JPWO2022162895A1 (fr) * 2021-01-29 2022-08-04
JP2022154159A (ja) * 2021-03-30 2022-10-13 味の素株式会社 感光性樹脂組成物
WO2023106101A1 (fr) * 2021-12-09 2023-06-15 日産化学株式会社 Composition de résine
KR20230123893A (ko) * 2022-02-17 2023-08-24 아사히 가세이 가부시키가이샤 감광성 수지 조성물, 폴리이미드 경화막, 및 이들의 제조 방법

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JPWO2021020463A1 (fr) * 2019-07-29 2021-02-04
JP7431241B2 (ja) 2019-07-29 2024-02-14 旭化成株式会社 ネガ型感光性樹脂組成物、ポリイミドの製造方法、硬化レリーフパターンの製造方法、及び半導体装置
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JPWO2022162895A1 (fr) * 2021-01-29 2022-08-04
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KR102803377B1 (ko) 2022-02-17 2025-05-02 아사히 가세이 가부시키가이샤 감광성 수지 조성물, 폴리이미드 경화막, 및 이들의 제조 방법

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