WO2020031958A1 - Composition de résine photosensible, feuille photosensible, films durcis de ces produits et procédés de production desdits films durcis, et composant électronique - Google Patents

Composition de résine photosensible, feuille photosensible, films durcis de ces produits et procédés de production desdits films durcis, et composant électronique Download PDF

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WO2020031958A1
WO2020031958A1 PCT/JP2019/030727 JP2019030727W WO2020031958A1 WO 2020031958 A1 WO2020031958 A1 WO 2020031958A1 JP 2019030727 W JP2019030727 W JP 2019030727W WO 2020031958 A1 WO2020031958 A1 WO 2020031958A1
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group
carbon atoms
photosensitive resin
acid
resin composition
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PCT/JP2019/030727
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English (en)
Japanese (ja)
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荒木斉
富川真佐夫
諏訪充史
小林秀行
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東レ株式会社
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Priority to KR1020217000458A priority Critical patent/KR20210040936A/ko
Priority to JP2019543402A priority patent/JP7409087B2/ja
Priority to CN201980044700.1A priority patent/CN112368641A/zh
Publication of WO2020031958A1 publication Critical patent/WO2020031958A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0387—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
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • 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

  • amide polycondensation reaction examples thereof include a method of reacting a tetracarboxylic acid diester with an diamine and then reacting with a diamine, a method of using a carbodiimide-based dehydrating condensing agent, and a method of reacting with a diamine after activated esterification.
  • alcohols When reacting the acid anhydride with the alcohol having an ethylenically unsaturated bond, other alcohols may be used at the same time. Other alcohols can be appropriately selected according to various purposes such as adjustment of exposure sensitivity and adjustment of solubility in an organic solvent.
  • the resin (A) may have a main chain terminal sealed with a terminal sealing agent.
  • the terminal blocking agent include a monoamine, an acid anhydride, a monocarboxylic acid, a monoacid chloride compound, and a monoactive ester compound.
  • a monoalcohol can also be used as a terminal blocking agent.
  • the terminal blocking agent introduced into the resin (A) used in the present invention can be easily detected by the following method.
  • a resin having a terminal blocking agent introduced therein is dissolved in an acidic solution and decomposed into an amine component and an acid anhydride component, which are structural units, and then subjected to gas chromatography (GC) or NMR measurement, whereby The terminal blocking agent used in the present invention can be easily detected.
  • the GC measurement is performed simultaneously with the external standard substance whose peak does not overlap with each component, and the integrated value of each peak of the chromatogram is compared with the external standard substance, whereby the mole of each monomer including the terminal blocking agent is measured. The ratio can be estimated.
  • the polyimide of the resin (A) can be obtained by partially dehydrating and cyclizing the polyimide precursor by heat treatment or chemical treatment with an acid or a base. More specifically, heat treatment may be performed by adding a solvent azeotropic with water such as m-xylene, or heat treatment may be performed at a low temperature of 100 ° C. or less by adding a weakly acidic carboxylic acid compound. .
  • the ring closing catalyst used in the above chemical treatment include a dehydrating condensing agent such as carboxylic anhydride or dicyclohexylcarbodiimide, and a base such as triethylamine. Further, it can be obtained by polymerizing an amine compound or a carboxylic acid compound containing an imide group as a residue as a monomer.
  • polybenzoxazole precursor of the resin (A) examples include polyhydroxyamide, polyaminoamide, a copolymer with polyamide or polyamideimide, and polyhydroxyamide is preferred.
  • the polyhydroxyamide having a dicarboxylic acid residue and a bisaminophenol residue can be obtained by reacting a bisaminophenol with a dicarboxylic acid or a corresponding dicarboxylic acid chloride or dicarboxylic acid active ester.
  • hydrophilic group examples include a carboxyl group, a carboxylic anhydride group, a sulfonic acid group, a phenolic hydroxyl group, and a hydroxyimide group. You may have these two or more types. Among these, a carboxyl group and a carboxylic anhydride group are preferable, and a carboxylic anhydride group is more preferable, from the viewpoint of further suppressing the development residue and further improving the storage stability.
  • organosilane compound other than the organosilane compound having a hydrophilic group and a styryl group examples include, for example, methyltrimethoxysilane, methyltriethoxysilane, methyltri (methoxyethoxy) silane, methyltripropoxysilane, methyltriisopropoxysilane , Methyltributoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, hexyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N- ( 2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, 3- (N
  • an acid catalyst such as hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polycarboxylic acid or anhydride thereof, or ion exchange resin can be used.
  • an acidic aqueous solution containing formic acid, acetic acid and / or phosphoric acid is preferable.
  • the resin (A) in the present invention preferably has a weight average molecular weight of 5,000 to 100,000.
  • a weight average molecular weight By setting the weight average molecular weight to 5,000 or more in terms of polystyrene by GPC (gel permeation chromatography), mechanical properties such as elongation after curing, strength at break, and elastic modulus can be improved.
  • the weight average molecular weight is 100,000 or less, developability can be improved. In order to obtain mechanical properties, 20,000 or more is more preferable.
  • the weight average molecular weight of at least one of the resins may be in the above range.
  • R 1 to R 7 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms or a carbon atom having 7 or more carbon atoms. Represents up to 50 arylalkyl groups, and Z - represents a carboxylate or borate anion.
  • the aryl group having 6 to 50 carbon atoms may be monocyclic or condensed polycyclic, and specific examples include a phenyl group, a naphthyl group, an anthracenyl group, and a phenanthrenyl group.
  • the organic groups represented by R 1 to R 7 when they are other than a hydrogen atom, they may be substituted.
  • substituent of the alkyl group having 1 to 50 carbon atoms include an amino group, a nitro group, an epoxy group, an alkoxycarbonyl group, a vinyl group, a (meth) acryl group, an ethynyl group, a coumarinylcarbonyl group, an anthraquinonyl group, a xanthonyl group and And thioxanthonyl groups.
  • the epoxy group include a glycidyl group and a 2,3-cyclohexyl epoxyethyl group.
  • Z ⁇ represents a carboxylate or borate anion.
  • the carboxylate to give Z ⁇ include formic acid, acetic acid, propionic acid, butanoic acid, valeric acid, pivalic acid, caproic acid, aliphatic carboxylic acid compounds such as enanthic acid, caprylic acid, pelargonic acid, capric acid, and benzoic acid.
  • Carboxylates derived from aromatic carboxylic acid compounds such as 4-benzoylbenzoic acid, salicylic acid, cinnamic acid and 4-biphenylcarboxylic acid are mentioned.
  • carboxylate represented by the general formula (2) and the general formula (3) are exemplified, and are preferable from the viewpoint of storage stability of the photosensitive resin composition of the present invention.
  • R 8 to R 16 each independently represent a hydrogen atom, a halogen atom, a nitro group or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It represents an aryl group, an arylalkyl group having 7 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms.
  • alkyl group having 1 to 50 carbon atoms represented by R 8 to R 16 in the general formula (2) and R 17 to R 25 in the general formula (3) a linear, branched or cyclic alkyl group may be used. Specific examples thereof include those exemplified for the alkyl group having 1 to 50 carbon atoms represented by R 1 to R 7 in the general formula (1) described above. The same applies to the substituent when substituted. Examples of the aryl group having 6 to 50 carbon atoms and the arylalkyl group having 7 to 15 carbon atoms include those exemplified in the description of R 1 to R 7 in the general formula (1). The same applies to.
  • the alkoxy group having 1 to 50 carbon atoms includes, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, cyclobutoxy group, n -Pentyloxy, isopentyloxy, sec-pentyloxy, tert-pentyloxy, neopentyloxy, 2-methylbutoxy, 1,2-dimethylpropoxy, 1-ethylpropoxy, cyclopentyloxy , N-hexyloxy group, isohexyloxy group, sec-hexyloxy group, tert-hexyloxy group, neohexyloxy group, 2-methylpentyloxy group, 1,2-dimethylbutoxy group, 2,3-dimethylbutoxy Group, 1-ethylbutoxy group, cyclohexyloxy group, etc. And the like. Examples of
  • R 26 to R 29 each represent a hydrogen atom, a halogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an alkoxy group having 1 to 50 carbon atoms, 50 alkenyl group, C 2-50 alkynyl group, C 6-50 aryl group, C 7-50 arylalkyl group, C 7-50 arylalkynyl group, furanyl group, thienyl group or pyrrolyl Represents a group.
  • Examples of the arylalkynyl group having 7 to 50 carbon atoms include a phenylethynyl group, a 3-phenylpropynyl group, a 4-phenylbutynyl group, a 5-phenylpentynyl group, and a 6-phenylhexynyl group.
  • the pyrrolyl group may be N-substituted, for example, N-methylpyrrolyl group, N-ethylpyrrolyl group, Nn-propylpyrrolyl group, N-isopropylpyrrolyl group, Nn-butylpyrrolyl group, N-isobutylpyrrolyl group , N-sec-butylpyrrolyl, N-tert-butylpyrrolyl, N-cyclobutylpyrrolyl, Nn-pentylpyrrolyl, N-isopentylpyrrolyl, N-sec-pentylpyrrolyl, N -Tert-pentylpyrrolyl group, N-neopentylpyrrolyl group, N-cyclopentylpyrrolyl group, Nn-hexylpyrrolyl group, N-isohexylpyrrolyl group, N-sec-hexylpyrrolyl group, N -
  • R 30 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms
  • R 31 to R 33 represent an alkynyl group having 50, an aryl group having 6 to 50 carbon atoms, an arylalkyl group having 7 to 50 carbon atoms, an arylalkynyl group having 7 to 15 carbon atoms, a furanyl group, a thienyl group or a pyrrolyl group; Represents an aryl group having 6 to 50 carbon atoms.
  • Specific examples of the component (B) include any combination of the above specific examples of the biguanide cation and the specific examples of the carboxylate anion or the borate anion.
  • Other specific examples include 1,5,7-triazabicyclo [4.4.0] dec-5-ene acetate and 1,5,7-triazabicyclo [4.4.0] decaphosphate.
  • Examples of the quinonediazide compound include a polyhydroxy compound in which sulfonic acid of quinonediazide is ester-bonded, a polyamino compound in which sulfonic acid of quinonediazide is sulfonamide-bonded, and a polyhydroxypolyamino compound in which sulfonic acid of quinonediazide is ester-bonded and / or sulfonamide. And the like. All the functional groups of the polyhydroxy compound, polyamino compound and polyhydroxypolyamino compound may not be substituted with quinonediazide, but it is preferable that 40 mol% or more of the entire functional groups are substituted with quinonediazide on average.
  • Polyhydroxy compounds include Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, TrisP-SA, TrisOCR-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, BisOCP -IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, Methylenetris-FR-CR, BisRS-26X, DML-MBPC, DML-MBOC, DML-OCHP, DML-PCHP, DML-PC DML-PTBP, DML-34X, DML-EP, DML-POP, Dimethylol-BisOC-P, DML-PFP, DML-PSBP, DML-MTrisPC, TriML-P, TriML-35XL, TML-BP, TML-H , TML-pp-BPF, TML-BPA, TMOM-BP, HML-TPPHBA, HML-TPHAP (all
  • the onium salt can function as a photocuring agent for an epoxy resin.
  • an onium salt for the epoxy resin a negative pattern can be obtained.
  • the onium salt include an aromatic iodonium complex salt and an aromatic sulfonium complex salt.
  • Trifluorophosphate (manufactured by San Apro Co., Ltd., trade name: CPI-210S), 4- ⁇ 4- (2-chlorobenzoyl) phenylthio ⁇ phenylbis (4-fluorophenyl) sulfonium hexafluoroantimonate (manufactured by Asahi Denka Kogyo Co., Ltd.) (Trade name: SP-172), a mixture of aromatic sulfonium hexafluoroantimonate containing 4- (phenylthio) phenyldiphenylsulfonium hexafluoroantimonate (manufactured by Dow Chemical Company) (Trade name: UVI-6976) and triphenylsulfonium tris (trifluoromethanesulfonyl) methanide (manufactured by BASF Japan, trade name: CGI TPS C1), tris [4- (4-acetylpheny
  • the photo-radical polymerization initiator (c-2) is not particularly limited as long as it is a compound capable of generating a radical upon exposure to light. And benzoate compounds are preferred because of their excellent sensitivity, stability and ease of synthesis. Among them, alkylphenone compounds and oxime ester compounds are preferable from the viewpoint of sensitivity, and oxime ester compounds are particularly preferable. When the processed film has a thickness of 5 ⁇ m or more, a phosphine oxide compound is preferable from the viewpoint of resolution. (C-2) By containing the photo-radical polymerization initiator, a negative pattern can be obtained.
  • aminobenzophenone compound examples include 4,4-bis (dimethylamino) benzophenone and 4,4-bis (diethylamino) benzophenone.
  • Benzyl is mentioned as a diketone compound.
  • ketoester compound examples include methyl benzoylformate and ethyl benzoylformate.
  • photo-radical polymerization initiator (c-2) include benzophenone, 4-benzoyl-4′-methyldiphenylketone, dibenzylketone, fluorenone, 4-phenylbenzophenone, 4,4-dichlorobenzophenone, Hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenylsulfide, alkylated benzophenone, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 4-benzoyl-N, N-dimethyl- N- [2- (1-oxo-2-propenyloxy) ethyl] benzenemethanaminium bromide, (4-benzoylbenzyl) trimethylammonium chloride, 2-hydroxy-3- (4-benzoylphenoxy) -N, N, N-trimethyl-1-propenami Um chloride monohydrate, thioxanthone, 2-chlorothioxan
  • Examples of the (D) component include diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, and trimethylolpropane di (meth) acrylate.
  • pentaerythritol tetraacrylate dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, tripentaerythritol heptaacrylate or tripentaerythritol octaacrylate is preferable, and the adhesion at the time of development due to improved hydrophobicity is preferred.
  • Examples of the compound of the other component (D) include an epoxy (meth) acrylate obtained by reacting a polyfunctional epoxy compound with (meth) acrylic acid. Epoxy (meth) acrylate adds hydrophilicity and can be used for the purpose of improving alkali developability.
  • Examples of the polyfunctional epoxy compound include the following compounds. These polyfunctional epoxy compounds are preferable because of their excellent heat resistance and chemical resistance.
  • the content of the component (D) is preferably from 5 to 100 parts by mass, more preferably from 10 to 50 parts by mass, per 100 parts by mass of the resin (A). When the content is in such a range, the effect of improving the exposure sensitivity and the chemical resistance of the cured film is easily obtained.
  • the photosensitive resin composition of the present invention may contain an antioxidant.
  • an antioxidant By containing an antioxidant, it is possible to suppress a decrease in mechanical properties such as yellowing and elongation of the cured film in a heat treatment in a later step.
  • oxidation of the metal material can be suppressed by a rust-preventing action on the metal material, which is preferable.
  • hindered phenolic antioxidants include the following, but are not limited to the following structures.
  • Hindered phenolic antioxidants also have the effect of improving resolution in order to suppress radical diffusion. Furthermore, when it can be developed with an aqueous alkali solution, it acts as a dissolution accelerator and also has a residue suppressing effect.
  • hindered amine antioxidants include, for example, bis (1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl Butylmalonate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, methyl-1,2,2,6,6-pentamethyl-4-piperidyl sebacate, 1,2,2 , 6,6-pentamethyl-4-piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, bis (2,2,6,6-tetramethyl-1- (octyloxy) decanoate) Reaction product of -4-piperidinyl) ester, 1,1-dimethylethyl hydroperoxide and octane, tetrakis (1,2,2,6,6-pentamethyl- -Pyridyl) butane-1,2,3,4
  • the heterocyclic compound containing a nitrogen atom includes 1H-imidazole, 1H-benzimidazole, 1H-pyrazole, indazole, 9H-carbazole, 1-pyrazoline, 2-pyrazoline, 3-pyrazoline, pyrazolidine, and 1H-triazole.
  • the content of the solvent is preferably 100 parts by mass or more for dissolving the composition with respect to 100 parts by mass of the resin (A), and 1,500 parts by mass for forming a coating film having a film thickness of 1 ⁇ m or more. It is preferable that the content is not more than 1 part by weight.
  • the photosensitive resin composition of the present invention may contain surfactants, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, alcohols such as ethanol, cyclohexanone, methyl It may contain ketones such as isobutyl ketone and ethers such as tetrahydrofuran and dioxane.
  • surfactants esters such as ethyl lactate and propylene glycol monomethyl ether acetate
  • alcohols such as ethanol, cyclohexanone, methyl
  • ketones such as isobutyl ketone and ethers such as tetrahydrofuran and dioxane.
  • the photosensitive resin composition of the present invention may contain a silane coupling agent as a silicon component as long as storage stability is not impaired.
  • a silane coupling agent include trimethoxyaminopropylsilane, trimethoxycyclohexylepoxyethylsilane, trimethoxyvinylsilane, trimethoxythiolpropylsilane, trimethoxyglycidyloxypropylsilane, tris (trimethoxysilylpropyl) isocyanurate, and triethoxyamino.
  • the shape of the photosensitive resin composition of the present invention is not limited as long as it contains the resin (A), the photopolymerization initiator (B), and the component (C). It may be.
  • the support is not particularly limited, but various commercially available films such as a polyethylene terephthalate (PET) film, a polyphenylene sulfide film, and a polyimide film can be used.
  • the bonding surface between the support and the photosensitive resin composition may be subjected to a surface treatment such as silicone, a silane coupling agent, an aluminum chelating agent, or polyurea in order to improve the adhesion and the releasability.
  • the thickness of the support is not particularly limited, but is preferably in the range of 10 to 100 ⁇ m from the viewpoint of workability.
  • a protective film may be provided on the film surface. Thereby, the surface of the photosensitive resin composition can be protected from contaminants such as dust and dust in the atmosphere.
  • the method of applying the photosensitive resin composition to the support includes spin coating using a spinner, spray coating, roll coating, screen printing, blade coater, die coater, calendar coater, meniscus coater, bar coater, roll coater, comma roll.
  • Examples of the method include a coater, a gravure coater, a screen coater, and a slit die coater.
  • the coating thickness varies depending on the coating method, the solid content concentration of the composition, the viscosity, and the like. preferable.
  • ⁇ ⁇ ⁇ ⁇ Oven, hot plate, infrared ray, etc. can be used for drying.
  • the drying temperature and the drying time may be within a range where the solvent can be volatilized, and it is preferable to appropriately set a range where the photosensitive resin composition is in an uncured or semi-cured state.
  • the temperature may be increased stepwise by combining these temperatures.
  • the heat treatment may be performed at 80 ° C. and 90 ° C. for 2 minutes each.
  • the photosensitive resin composition of the present invention is applied to a substrate, or the photosensitive sheet is laminated on the substrate.
  • a substrate a metal copper plating substrate, a silicon wafer, and a material such as ceramics and gallium arsenide are used, but the material is not limited to these.
  • the coating method include spin coating using a spinner, spray coating, and roll coating. The coating 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 thickness after drying is 0.1 to 150 ⁇ m.
  • the photosensitive resin composition is applied, or the substrate on which the photosensitive sheet of the present invention is laminated is dried to obtain a photosensitive resin film. Drying is preferably performed using an oven, a hot plate, infrared rays or the like at a temperature of 50 ° C. to 150 ° C. for 1 minute to several hours. In the case of a photosensitive sheet, the drying step does not always have to be performed.
  • the photosensitive resin film is exposed to actinic radiation through a mask having a desired pattern to expose the photosensitive resin film.
  • Actinic rays used for exposure include ultraviolet rays, visible rays, electron beams, and X-rays.
  • the exposed photosensitive resin film may be subjected to a post-exposure bake (PEB) step as necessary.
  • the PEB step is preferably performed at 50 ° C. to 150 ° C. for 1 minute to several hours using an oven, a hot plate, infrared rays or the like.
  • the poor solvent examples include toluene, xylene, methanol, ethanol, isopropyl alcohol, ethyl lactate, propylene glycol methyl ether acetate, and water.
  • a good solvent and a poor solvent are used as a mixture, it is preferable to adjust the ratio of the poor solvent to the good solvent depending on the solubility of the polymer in the photosensitive resin composition.
  • each solvent may be used in combination of two or more kinds, for example, several kinds.
  • the developer used for development is one that dissolves and removes a polymer soluble in an aqueous alkali solution, and is typically an aqueous alkaline solution in which an alkali compound is dissolved.
  • the alkaline compound include tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, and dimethylamine.
  • Examples include aminoethyl methacrylate, cyclohexylamine, ethylenediamine, and hexamethylenediamine.
  • a polar solvent such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Alcohols such as isopropanol, ethyl lactate, esters such as propylene glycol monomethyl ether acetate, ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, and methyl isobutyl ketone may be used alone or in combination.
  • an organic solvent ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and the like can be used in addition to the above-mentioned developer.
  • an alcohol such as ethanol and isopropyl alcohol, an ester such as ethyl lactate and propylene glycol monomethyl ether acetate, and the like may be added to the water for rinsing.
  • the cured film formed from the photosensitive resin composition or the photosensitive sheet of the present invention can be used for electronic components such as semiconductor devices and multilayer wiring boards. Specifically, it is suitable for use as a passivation film of a semiconductor, a surface protection film of a semiconductor device, an interlayer insulating film, an interlayer insulating film in a multilayer wiring for high-density mounting of 2 to 10 layers, and an insulating layer of an organic electroluminescent device. Although it is used, it is not limited to this and can take various structures.
  • the surface of the substrate on which the cured film is to be formed can be appropriately selected depending on the application and process. Examples thereof include silicon, ceramics, metals, and epoxy resins. Even when the substrate surface is a substrate composed of two or more of these materials, Good.
  • FIG. 1 is an enlarged sectional view of a pad portion of a semiconductor device having a bump according to the present invention.
  • a passivation film 3 is formed on an input / output aluminum (hereinafter abbreviated as Al) pad 2 on a silicon wafer 1, and a via hole is formed in the passivation film 3.
  • An insulating film 4 is formed thereon as a pattern of a cured film obtained by curing the photosensitive resin composition of the present invention, and a metal (Cr, Ti, etc.) film 5 is formed so as to be connected to the Al pad 2.
  • Metal wiring (Al, Cu, etc.) 6 is formed by electrolytic plating or the like.
  • the metal film 5 etches the periphery of the solder bump 10 to insulate between the pads.
  • a barrier metal 8 and a solder bump 10 are formed on the insulated pad.
  • the cured film obtained by curing the photosensitive resin composition of the insulating film 7 can be processed into a thick film at the scribe line 9.
  • the cured film of the present invention is excellent in elongation at break and strength at break when a polyimide resin is used, so that the stress from the sealing resin can be reduced even at the time of mounting. And a highly reliable semiconductor device can be provided.
  • FIG. 2A an input / output Al pad 2 and a passivation film 3 are formed on a silicon wafer 1, and an insulating film 4 is formed as a pattern of a cured film obtained by curing the photosensitive resin composition of the present invention. .
  • a metal (Cr, Ti, etc.) film 5 is formed so as to be connected to the Al pad 2, and as shown in FIG. 2c, the metal wiring 6 is formed by plating. Form a film.
  • a barrier metal 8 and a solder bump 10 are formed. Then, the wafer is diced along the last scribe line 9 and cut into chips. If the insulating film 7 has no pattern formed on the scribe line 9 or if a residue remains, cracks and the like occur during dicing, which affects the reliability evaluation 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 a semiconductor device.
  • varnish a photosensitive resin composition before curing
  • varnish a photosensitive resin composition before curing
  • a polytetrafluoroethylene filter manufactured by Sumitomo Electric Industries, Ltd.
  • PLA parallel light mask aligner
  • a sensitivity was used.
  • Gray scale mask for measurement having a 2 to 50 ⁇ m 1: 1 line & space pattern. 1%, 5%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 25%, 30%, 35%, 40%, 50% and 60%).
  • the varnish was a negative type, it was baked after exposure at 120 ° C. for 1 minute, and developed using a coating and developing apparatus MARK-7.
  • TMAH tetramethylammonium hydroxide
  • the film thickness was measured after development, and the minimum exposure amount at which the residual film ratio of the exposed portion exceeded 90% was defined as the sensitivity.
  • the exposure was measured with an I-line illuminometer.
  • the film thickness was measured at a refractive index of 1.629 using Lamda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd. The same applies to the film thickness described below.
  • the prepared pre-baked film is made of PLA-501F, an ultra-high pressure mercury lamp is used as a light source (mixed line of g-line, h-line and i-line), and a gray scale mask (2 to 50 ⁇ m, 1: 1 line) for sensitivity measurement & 1%, 5%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 25%, 30%, 35%, 40%, 50% And an area having a transmittance of 60%).
  • AD-2000 automatic developing device manufactured by Takizawa Sangyo Co., Ltd.
  • a shower was performed for 100 seconds using a 0.045% by mass aqueous solution of potassium hydroxide or 2.38% by mass of TMAH.
  • the film thickness was measured after development, and the minimum exposure amount at which the residual film ratio of the exposed portion exceeded 90% was defined as the sensitivity. The exposure was measured with an I-line illuminometer. The film thickness was measured at a refractive index of 1.550 using Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd. The same applies to the film thickness described below.
  • the cured film was immersed in a resist stripping solution, N300 at 50 ° C. for 3 minutes, and pattern peeling and change in film thickness (indicating swelling or elution amount) were observed.
  • the evaluation of the results was performed in the same manner as in (3) -1 ⁇ Chemical Resistance Evaluation A ⁇ .
  • Copper substrate adhesion evaluation (5) Copper substrate adhesion evaluation A The adhesion to metal copper was evaluated by the following method.
  • the substrate was taken out, the substrate was divided into two parts, and the cured film was cut into 10 rows and 10 columns at 2 mm intervals using a single blade on the cured film.
  • the adhesive property between the metal material and the cured resin film was evaluated based on how many of the 100 squares were peeled off by peeling with "Cellotape" (registered trademark).
  • the other sample substrate was subjected to a PCT treatment for 400 hours under a saturation condition of 121 ° C.
  • peeling test was performed in any of the substrates. In any of the substrates, the peeling test was performed such that the number of peeled samples was 0, 5, 1 or more but less than 10, 4, 10 or more but less than 30, 3, 30 or more and less than 50, and 2 or more.
  • Copper substrate adhesion evaluation B A cured film having a thickness of 2.0 ⁇ m was formed on the copper substrate in the same manner as in the method described in (3) -2. The obtained substrate was divided into two, and the cured film was cut into 10 rows and 10 columns at 2 mm intervals using a single blade in each cured substrate. Using one of the sample substrates, the adhesive property between the metal material and the cured resin film was evaluated based on how many of the 100 squares were peeled off by peeling with "Cellotape" (registered trademark). The other sample substrate was subjected to a PCT treatment at 85 ° C.
  • polyimide precursor resin (P-2) powder The molecular weight of the polyimide precursor (P-1) was measured by gel permeation chromatography (in terms of standard polystyrene). As a result, the weight average molecular weight (Mw) was 25,000, and the PDI was 2.3.
  • the polyimide precursor (P-2) is soluble in an aqueous alkali solution, and a photosensitive resin composition using this is developed with a 2.38% by mass aqueous TMAH solution.
  • Example 1 Under a yellow lamp, 10.00 g of a polyimide precursor (P-1), 1,2-octanedione, 1- [4- (phenylthio) -2- (O-benzoyloxime)] (“Irgacure OXE-01 ( (Trade name) "BASF) 0.50 g, BI 0.30 g, NK ester 4G (trade name) (manufactured by Shin-Nakamura Chemical Co., Ltd., chemical name: tetraethylene glycol dimethacrylate) 2.00 g, N-phenyl 0.2 g of diethanolamine and 0.30 g of 3-trimethoxysilylphthalamic acid were dissolved in 15.15 g of N-methylpyrrolidone (NMP) and 3.81 g of ethyl lactate (EL), and “Polyflow”, an acrylic surfactant, was used.
  • NMP N-methylpyrrolidone
  • EL ethyl lactate
  • Example 2 The same operation was performed as in Example 1 except that BI was changed to B-II.
  • Example 3 The same operation as in Example 1 was carried out except that BI was changed to B-III.
  • Example 4 The procedure was performed in the same manner as in Example 1 except that BI was changed to B-IV.
  • Example 5 The same operation as in Example 1 was performed except that BI was changed to BV.
  • Example 6 The operation was performed in the same manner as in Example 1 except that BI was changed to B-VI.
  • Example 7 The same operation was performed as in Example 1 except that BI was changed to B-VII.
  • Example 8 The same operation as in Example 1 was performed except that BI was changed to B-VIII.
  • Example 9 The same operation as in Example 1 was performed, except that BI was changed to B-IX.
  • Example 10 The same operation was performed as in Example 3, except that P-1 was changed to P-3.
  • Example 11 The same operation was performed as in Example 3, except that P-1 was changed to P-4.
  • the properties of the obtained varnish were evaluated by the above-mentioned evaluation methods according to the pattern processability (sensitivity A, developability A), chemical resistance A, elongation at break, strength at break, coefficient of linear thermal expansion, copper substrate adhesion evaluation A, imide The conversion and storage stability were measured.
  • Example 17 was carried out in the same manner as in Example 17, except that Irgacure 379 was changed to bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (“Irgacure 819 (trade name)”, manufactured by BASF).
  • Irgacure 379 was treated with 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl ⁇ -2-methyl-propan-1-one ("Irgacure 127 (trade name)"). (Manufactured by BASF) was carried out in the same manner as in Example 17.
  • Example 17 was carried out in the same manner as in Example 17, except that Irgacure 379 was changed to ethyl p-dimethylaminobenzoate.
  • Example 17 was carried out in the same manner as in Example 17, except that Irgacure 379 was replaced with 4-phenylbenzophenone.
  • a solid polyfunctional aromatic epoxy resin (YDCN-700-10 (trade name), manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), which is a cresol novolac type polyfunctional epoxy resin, is used.
  • the procedure was performed in the same manner as in Example 1 except that 2 g of pentaerythritol hexaacrylate (DPHA (trade name), manufactured by Nippon Kayaku) was added. However, only the imidation ratio was not measured.
  • Example 23 Under a yellow light, 10.00 g of a polyimide precursor (P-2), 2.0 g of TP5-280M (manufactured by Toyo Gosei; 5-naphthoquinonediazidesulfonic acid ester compound of TrisP-PA (manufactured by Honshu Chemical)), B- 0.2 g of IMP was dissolved in 14.5 g of NMP, and 0.10 g of a 1 wt% NMP solution of Polyflow 77 was added and stirred to obtain a varnish. The characteristics of the obtained varnish were measured by the above evaluation method. [Example 24] Example 23 was carried out in the same manner as in Example 23 except that BI was changed to B-II.
  • Example 23 was carried out in the same manner as in Example 23 except that BI was changed to B-III.
  • Example 23 was carried out in the same manner as in Example 23 except that BI was changed to B-IV.
  • Example 23 was carried out in the same manner as in Example 23 except that BI was changed to BV.
  • Example 28 Example 23 was carried out in the same manner as in Example 23 except that BI was changed to B-VI.
  • Example 29 was carried out in the same manner as in Example 23 except that BI was changed to B-VII.
  • Example 30 Example 23 was carried out in the same manner as in Example 23 except that BI was changed to B-VIII.
  • Example 37 was carried out in the same manner as in Example 37 except that BI was changed to B-IV.
  • Example 37 was carried out in the same manner as in Example 37 except that BI was changed to BV.
  • Example 37 was carried out in the same manner as in Example 37 except that BI was changed to B-VI.
  • Example 37 was carried out in the same manner as in Example 37 except that BI was changed to B-VII.
  • Example 37 was carried out in the same manner as in Example 37 except that BI was changed to B-VIII.
  • Example 45 Example 37 was carried out in the same manner as in Example 37 except that BI was changed to B-IX.
  • Example 46 Under yellow light, 0.240 g of TP5-280M (manufactured by Toyo Gosei; 5-Naphthoquinonediazidesulfonic acid ester compound of TrisP-PA (manufactured by Honshu Chemical)), 0.160 g of BI, and 3-methacryloxypropyltrimethoxysilane (KBM-503 (trade name), manufactured by Shin-Etsu Chemical Co., Ltd.) in 0.120 g and a mixed solvent of 7.565 g of PGME and 3.200 g of PGMEA were dissolved in a silicone-based surfactant (trade name “BYK” (registered trademark)).
  • a silicone-based surfactant trade name “BYK” (registered trademark)
  • Example 46 was carried out in the same manner as in Example 46 except that BI was changed to B-II.
  • Example 1 Example 1 was carried out in the same manner as in Example 1 except that BI was changed to BX.
  • Example 2 The operation was performed in the same manner as in Example 3 except that OXE-01 was not added.
  • Example 3 The same operation was performed as in Example 1 except that BI was not added.
  • Example 4 Example 23 was carried out in the same manner as in Example 23 except that BI was changed to BX.
  • Example 5 The same operation as in Example 25 was performed except that TP5-280M was not added.
  • Comparative Example 6 The same operation was performed as in Example 23 except that BI was not added.
  • Comparative Example 7 The same operation as in Example 22 was carried out except that B-III was not added.
  • Example 37 was carried out in the same manner as in Example 37 except that BI was changed to BX.
  • Example 9 The same operation as in Example 39 was carried out except that IC-819 and OXE-02 were not added.
  • Example 10 The same operation as in Example 37 was performed except that BI was not added.
  • Example 46 was carried out in the same manner as in Example 46, except that BI was changed to BX.
  • Example 12 The same operation as in Example 48 was performed except that TP5-280M was not added.
  • Comparative Example 13 The same operation as in Example 46 was performed except that BI was not added. The results of the examples and comparative examples are shown in the following table.

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  • Spectroscopy & Molecular Physics (AREA)
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  • Inorganic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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  • Photosensitive Polymer And Photoresist Processing (AREA)
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Abstract

La présente invention aborde le problème de la fourniture d'une composition de résine photosensible dotée d'une bonne aptitude au traitement de motif et qui peut être durcie à basse température pour devenir un film durci ayant une résistance chimique élevée, une élasticité élevée, un allongement élevé et une adhésivité élevée à un métal, en particulier au cuivre. La présente invention concerne une composition de résine photosensible comprenant (A) au moins une résine choisie parmi le groupe constitué par une résine époxy, un polyimide, un précurseur de polyimide, un polybenzoxazole, un précurseur de polybenzoxazole et un polysiloxane, (B) un générateur de base thermique, et (C) un photosensibilisateur, le générateur de base thermique (B) comprenant au moins un composant choisi parmi un dérivé de guanidine et un dérivé de biguanide, et le photosensibilisateur (C) comprenant (c-1) un générateur de photo-acide et/ou (c-2) un initiateur de polymérisation photoradicalaire.
PCT/JP2019/030727 2018-08-09 2019-08-05 Composition de résine photosensible, feuille photosensible, films durcis de ces produits et procédés de production desdits films durcis, et composant électronique WO2020031958A1 (fr)

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JP2019543402A JP7409087B2 (ja) 2018-08-09 2019-08-05 感光性樹脂組成物、感光性シート、ならびにそれらの硬化膜およびその製造方法、電子部品
CN201980044700.1A CN112368641A (zh) 2018-08-09 2019-08-05 感光性树脂组合物、感光性片材、以及它们的固化膜及其制造方法、电子部件

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CN116552074A (zh) * 2023-05-05 2023-08-08 江门建滔电子发展有限公司 一种高散热低介电覆铜板及其制备方法
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