CN113168102A - Photosensitive resin composition, method for producing patterned cured product, interlayer insulating film, covercoat, surface protective film, and electronic component - Google Patents
Photosensitive resin composition, method for producing patterned cured product, interlayer insulating film, covercoat, surface protective film, and electronic component Download PDFInfo
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- CN113168102A CN113168102A CN201980065325.9A CN201980065325A CN113168102A CN 113168102 A CN113168102 A CN 113168102A CN 201980065325 A CN201980065325 A CN 201980065325A CN 113168102 A CN113168102 A CN 113168102A
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- Prior art keywords
- photosensitive resin
- group
- resin composition
- component
- formula
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- 239000011342 resin composition Substances 0.000 title claims abstract description 66
- 239000011229 interlayer Substances 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 230000001681 protective effect Effects 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 239000004642 Polyimide Substances 0.000 claims abstract description 14
- 229920001721 polyimide Polymers 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000002243 precursor Substances 0.000 claims abstract description 12
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 125000005577 anthracene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 229920005989 resin Polymers 0.000 claims description 54
- 239000011347 resin Substances 0.000 claims description 54
- 125000001931 aliphatic group Chemical group 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- GJNKQJAJXSUJBO-UHFFFAOYSA-N 9,10-diethoxyanthracene Chemical compound C1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 GJNKQJAJXSUJBO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 238000004806 packaging method and process Methods 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- 238000012719 thermal polymerization Methods 0.000 claims description 4
- BWSIKJKXQWLTLS-UHFFFAOYSA-N 1,2-dimethoxyanthracene Chemical compound C1=CC=CC2=CC3=C(OC)C(OC)=CC=C3C=C21 BWSIKJKXQWLTLS-UHFFFAOYSA-N 0.000 claims description 3
- KLQVBEXCUCUXDP-UHFFFAOYSA-N 1-(2,2-diethoxyethyl)anthracene Chemical compound C(C)OC(CC1=CC=CC2=CC3=CC=CC=C3C=C12)OCC KLQVBEXCUCUXDP-UHFFFAOYSA-N 0.000 claims description 3
- 239000010408 film Substances 0.000 description 115
- 239000000047 product Substances 0.000 description 49
- 238000011161 development Methods 0.000 description 27
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- 239000003112 inhibitor Substances 0.000 description 21
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- -1 methylene, bis (trifluoromethyl) methylene Chemical group 0.000 description 14
- 239000006087 Silane Coupling Agent Substances 0.000 description 13
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- 239000010410 layer Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- 238000001723 curing Methods 0.000 description 10
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 150000002923 oximes Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000004020 conductor Substances 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 4
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 3
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920005575 poly(amic acid) Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
- JTSXFTWPBWFCPA-UHFFFAOYSA-N 2,2,5-trimethyl-4-oxido-4-aza-3-azoniabicyclo[3.2.2]nonane 3-oxide Chemical compound C1CC2CCC1(C)N([O-])[N+](=O)C2(C)C JTSXFTWPBWFCPA-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- BMVJLODMRABQES-UHFFFAOYSA-N 2-(aminomethyl)-3-trimethoxysilylpropan-1-ol Chemical compound OCC(C[Si](OC)(OC)OC)CN BMVJLODMRABQES-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/145—Polyamides; Polyesteramides; Polyimides
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- 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
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- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- 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
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- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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Abstract
A photosensitive resin composition contains (A) a polyimide precursor having a polymerizable unsaturated bond, (B) a polymerizable monomer having an aliphatic cyclic skeleton, (C) a photopolymerization initiator, (D) a compound having an anthracene structure, and (E) a solvent.
Description
Technical Field
The invention relates to a photosensitive resin composition, a method for producing a pattern cured product, a cured product, an interlayer insulating film, a cover coat, a surface protective film and an electronic component.
Background
Conventionally, polyimide or polybenzazole having excellent heat resistance, electrical properties, mechanical properties and the like has been used as a surface protective film and an interlayer insulating film of a semiconductor deviceAnd (3) azole. In recent years, a photosensitive resin composition having photosensitive characteristics imparted to these resins itself has been used, and if this photosensitive resin composition is used, the production process of a pattern cured product can be simplified, and a complicated production process can be shortened. (see, for example, patent document 1)
In recent years, however, miniaturization of transistors supporting high performance of computers has approached the limit of the rule of proportionality, and a stacked device structure in which semiconductor elements are three-dimensionally stacked has attracted attention for further improvement in performance and high speed.
Among the stacked device structures, a Multi-die Fanout Wafer Level package (Multi-die Fanout Wafer Level Packaging) is a package manufactured by collectively sealing a plurality of chips in one package, and is drawing attention because it can be expected to reduce the cost and improve the performance as compared with a fan-out Wafer Level package (manufactured by sealing one chip in one package) proposed in the related art.
In the fabrication of a multi-chip fan-out type wafer level package, low temperature curability is strongly required from the viewpoint of protecting a high performance chip, protecting a sealing material having low heat resistance, and improving yield (for example, see patent document 2).
Further, as the resin composition, a resin composition containing a polyimide precursor is disclosed (for example, see patent document 3).
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 2009-265520
Patent document 2: international publication No. 2008/111470
Patent document 3: japanese patent laid-open publication No. 2016-199662
Disclosure of Invention
The purpose of the present invention is to provide a photosensitive resin composition which can form a good cured product even when cured at a low temperature of 200 ℃ or less and which is excellent in resolution and pattern formability after development, a method for producing a pattern cured product, a cured product, an interlayer insulating film, a covercoat, a surface protective film, and an electronic component.
According to the present invention, the following photosensitive resin composition and the like can be provided.
1. A photosensitive resin composition comprising:
(A) a polyimide precursor having a polymerizable unsaturated bond,
(B) A polymerizable monomer having an aliphatic cyclic skeleton,
(C) A photopolymerization initiator,
(D) A compound containing an anthracene structure, and
(E) a solvent.
2. The photosensitive resin composition according to claim 1, wherein the component (A) is a polyimide precursor having a structural unit represented by the following formula (1).
[ solution 1]
(in the formula (1), X1Is a 4-valent radical having more than 1 aromatic group, -COOR1The radicals and the-CONH-radicals being in ortho-position to one another, -COOR2The radicals and the-CO-radicals are in the ortho position relative to one another. Y is1Is a 2-valent aromatic group. R1And R2Each independently represents a hydrogen atom, a group represented by the following formula (2) or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, R1And R2At least one of them is a group represented by the above formula (2). )
[ solution 2]
(in the formula (2), R3~R5Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and m is an integer of 1 to 10. )
3. The photosensitive resin composition according to 1 or 2, wherein the component (B) comprises: a polymerizable monomer having a group containing a polymerizable unsaturated double bond and having an aliphatic cyclic skeleton.
4. The photosensitive resin composition according to claim 3, wherein the component (B) is: a polymerizable monomer having 2 or more groups containing a polymerizable unsaturated double bond and having an aliphatic cyclic skeleton.
5. The photosensitive resin composition according to any one of 1 to 3, wherein the component (B) contains a polymerizable monomer represented by the following formula (3).
[ solution 3]
(in the formula (3), R6And R7Each independently is an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the following formula (4). n1 is 0 or 1, n2 is an integer of 0 to 2, and n1+ n2 is greater than or equal to 1. n 1R6And n 2R7At least one of them is a group represented by the following formula (4). )
[ solution 4]
(in the formula (4), R9~R11Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and l is an integer of 0 to 10. )
6. The photosensitive resin composition according to claim 5, wherein n1+ n2 is 2 or 3.
7. The photosensitive resin composition according to any one of 1 to 6, wherein the component (B) contains a polymerizable monomer represented by the following formula (5).
[ solution 5]
8. The photosensitive resin composition according to any one of 1 to 7, wherein the component (D) comprises a compound represented by the following formula (31).
[ solution 6]
(in the formula (31), R61Each independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms or a halogen atom, and n10 is an integer of 0 to 8. )
9. The photosensitive resin composition according to any one of claims 1 to 7, wherein the component (D) is at least one selected from the group consisting of dibutoxyanthracene, dimethoxyanthracene, diethoxyanthracene, and diethoxyethylanthracene.
10. The photosensitive resin composition according to any one of claims 1 to 9, further comprising (F) a thermal polymerization initiator.
11. The photosensitive resin composition according to any one of claims 1 to 10, which is for panel-level packaging.
12. A method for producing a pattern cured product, comprising the steps of:
a step of forming a photosensitive resin film by coating the photosensitive resin composition of any one of 1 to 11 on a substrate and drying the coating;
pattern-exposing the photosensitive resin film to obtain a resin film;
a step of obtaining a pattern resin film by developing the pattern-exposed resin film with an organic solvent; and
and a step of heat-treating the patterned resin film.
13. The method for producing a patterned cured product according to claim 12, wherein the temperature of the heat treatment is 200 ℃ or lower.
14. A cured product obtained by curing the photosensitive resin composition according to any one of 1 to 11.
15. The cured product according to claim 14, which is a pattern cured product.
16. An interlayer insulating film, a cap coat or a surface protective film, which is produced using the cured product of 14 or 15.
17. An electronic part comprising the interlayer insulating film, covercoat or surface protective film of 16.
According to the present invention, a photosensitive resin composition, a method for producing a pattern cured product, a cured product, an interlayer insulating film, a coverlay, a surface protective film, and an electronic component, which can form a good cured product even when cured at a low temperature of 200 ℃ or lower and are excellent in resolution and pattern formability after development, can be provided.
Drawings
Fig. 1 is a process diagram for manufacturing an electronic component according to an embodiment of the present invention.
Detailed Description
The embodiments of the photosensitive resin composition, the method for producing a pattern cured product using the photosensitive resin composition, the cured product, the interlayer insulating film, the coverlay, the surface protective film, and the electronic component of the present invention will be described in detail below. The present invention is not limited to the following embodiments.
In the present specification, "a or" B "may include either one of a and B, or both of them. The term "step" in the present specification includes not only an independent step but also a step that can achieve a desired action of the step even when the step is not clearly distinguished from other steps.
The numerical range represented by the term "to" represents a range including the numerical values recited before and after the term "to" as the minimum value and the maximum value, respectively. In the present specification, the content of each component in the composition refers to the total amount of a plurality of substances present in the composition unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition. Further, the exemplified materials may be used alone or in combination of two or more unless otherwise specified.
The "(meth) acryloyl group" in the present specification means an "acryloyl group" and a "methacryloyl group".
The photosensitive resin composition of the present invention contains (a) a polyimide precursor having a polymerizable unsaturated bond (hereinafter also referred to as "component (a)"), (B) a polymerizable monomer having an aliphatic cyclic skeleton (hereinafter also referred to as "crosslinker"), (C) a photopolymerization initiator (hereinafter also referred to as "component (C)"), (D) a compound having an anthracene structure (hereinafter also referred to as "component (D)"), and (E) a solvent (hereinafter also referred to as "component (E)").
Thus, even when cured at a low temperature of 200 ℃ or lower, a good cured product can be formed, and the resolution and pattern formability after development are excellent.
As an optional effect, a good cured product can be formed even by curing at a low temperature of 200 ℃ or lower, and a cured product having excellent resolution after curing can be formed.
The photosensitive resin composition of the present invention is preferably a negative photosensitive resin composition.
In addition, the photosensitive resin composition of the present invention is preferably used for a panel-level package (for example, a package having no package substrate but having a structure in which a rewiring layer for drawing wires from terminals of a chip (chip) is connected to external terminals instead) from the viewpoint of the photosensitive characteristics at the time of h-line exposure. The photosensitive resin composition of the present invention is preferably a material for panel level packaging or a material for electronic parts.
The component (a) is not particularly limited, but is preferably a polyimide precursor which has a high transmittance when i-line is used as a light source in patterning and exhibits high curing properties even when cured at a low temperature of 200 ℃.
Examples of the polymerizable unsaturated bond include a carbon-carbon double bond.
(A) The component (b) is preferably a polyimide precursor having a structural unit represented by the following formula (1). Thus, i-line has a high transmittance, and a good cured product can be formed even when cured at a low temperature of 200 ℃ or lower.
The content of the structural unit represented by formula (1) is preferably 50 mol% or more, more preferably 80 mol% or more, and still more preferably 90 mol% or more, based on the total constituent units of component (a). The upper limit is not particularly limited, and may be 100 mol%.
[ solution 7]
(in the formula (1), X1Is a 4-valent radical having more than 1 aromatic group, -COOR1The radicals and the-CONH-radicals being in ortho-position to one another, -COOR2The radicals and the-CO-radicals are in the ortho position relative to one another. Y is1Is a 2-valent aromatic group. R1And R2Each independently represents a hydrogen atom, a group represented by the following formula (2) or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, R1And R2At least one of them is a group represented by the above formula (2). )
[ solution 8]
(in the formula (2), R3~R5Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and m is an integer of 1 to 10 (preferably 2 to 5)Integer, more preferably 2 or 3). )
X in the formula (1)1In the 4-valent group having 1 or more (preferably 1 to 3, more preferably 1 or 2) aromatic groups in the (a) aromatic group, the aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group. Aromatic hydrocarbon groups are preferred.
X as formula (1)1The aromatic hydrocarbon group of (2) to (4) is a 2 to (2, 3 or 4) valent group formed from a benzene ring, a 2 to 4 valent group formed from naphthalene, a 2 to 4 valent group formed from perylene, or the like.
X as formula (1)1Examples of the 4-valent group having 1 or more aromatic groups in (b) include, but are not limited to, the 4-valent group of the following formula (6).
[ solution 9]
(in the formula (6), X and Y each independently represent a 2-valent group which is not conjugated to the benzene ring to which each is bonded or a single bond; Z is an ether group (-O-) or a thioether group (-S-) (preferably-O-)
In formula (6), the 2-valent group of X and Y that is not conjugated to the benzene ring to which each is bonded is preferably-O-, -S-, methylene, bis (trifluoromethyl) methylene, or difluoromethylene, more preferably-O-.
Y of formula (1)1The 2-valent aromatic group in (b) may be a 2-valent aromatic hydrocarbon group, and may be a 2-valent aromatic heterocyclic group. Preferably a 2-valent aromatic hydrocarbon group.
Y as formula (1)1Examples of the 2-valent aromatic hydrocarbon group include, but are not limited to, the group represented by the following formula (7).
[ solution 10]
(in the formula (7), R12~R19Each independently a hydrogen atom, a 1-valent aliphatic hydrocarbon group or a 1-valent organic group having a halogen atomAnd (4) clustering. )
R as formula (7)12~R19The 1-valent aliphatic hydrocarbon group (preferably having 1 to 10 carbon atoms, more preferably having 1 to 6 carbon atoms) may include a methyl group and the like. For example, it may be R12And R15~R19Is a hydrogen atom, R13And R14Is a 1-valent aliphatic hydrocarbon group.
R of formula (7)12~R19The 1-valent organic group having a halogen atom (preferably a fluorine atom) of (a) is preferably a 1-valent aliphatic hydrocarbon group having a halogen atom (preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms), and examples thereof include a trifluoromethyl group and the like.
R as formula (1)1And R2Examples of the aliphatic hydrocarbon group having 1 to 4 (preferably 1 or 2) carbon atoms include methyl, ethyl, n-propyl, 2-propyl, n-butyl and the like.
R of formula (1)1And R2At least one of the groups (2) is a group represented by the formula (2), and preferably all of the groups are represented by the formula (2).
R as formula (2)3~R5Examples of the aliphatic hydrocarbon group having 1 to 3 (preferably 1 or 2) carbon atoms include a methyl group, an ethyl group, an n-propyl group, and a 2-propyl group. Preferably methyl.
The polyimide precursor having the structural unit represented by formula (1) can be obtained, for example, as follows: a tetracarboxylic dianhydride represented by the following formula (8) is reacted with a diamino compound represented by the following formula (9) in an organic solvent such as N-methyl-2-pyrrolidone to obtain a polyamic acid, and a compound represented by the following formula (10) is added and reacted in the organic solvent to partially introduce an ester group.
The tetracarboxylic dianhydride represented by the formula (8) and the diamino compound represented by the formula (9) may be used alone or in combination of two or more.
[ solution 11]
(in the formula (8), X1Is X of formula (1)1The corresponding groups. )
[ solution 12]
H2N-Y1-NH2…(9)
(in the formula (9), Y1As defined in formula (1). )
[ solution 13]
R-OH…(10)
(in the formula (10), R is a group represented by the formula (2).)
(A) The component (C) may have a structural unit other than the structural unit represented by the formula (1).
As the structural unit other than the structural unit represented by formula (1), a structural unit represented by formula (11) and the like can be mentioned.
[ solution 14]
(in the formula (11), X2Is a 4-valent radical having more than 1 aromatic group, -COOR51The radicals and the-CONH-radicals being in ortho-position to one another, -COOR52The radicals and the-CO-radicals are in the ortho position relative to one another. Y is2Is a 2-valent aromatic group. R51And R52Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. )
X of formula (11)2The 4-valent group having 1 or more aromatic groups in (A) may be represented by X of the formula (1)1The same group as the 4-valent group having 1 or more aromatic groups in (a).
Y of formula (11)2The 2-valent aromatic group in (2) may be represented by Y in the formula (1)1The 2-valent aromatic group of (1) is the same group.
R of formula (11)51And R52The aliphatic hydrocarbon group having 1 to 4 carbon atoms includes1And R2The same as the aliphatic hydrocarbon group having 1 to 4 carbon atoms.
One kind of the constitutional unit other than the constitutional unit represented by formula (1) may be used alone, or two or more kinds may be combined.
The content of the structural unit other than the structural unit represented by formula (1) is preferably less than 50 mol% with respect to the entire structural unit of component (a).
In the component (a), the ratio of the esterified carboxyl groups in the group represented by the formula (2) to all the carboxyl groups and all the carboxylic acid esters is preferably 50 mol% or more, more preferably 60 to 100 mol%, and still more preferably 70 to 90 mol%.
(A) The molecular weight of the component (A) is not particularly limited, but is preferably 10,000 to 200,000 in terms of number average molecular weight.
The number average molecular weight can be measured by gel permeation chromatography, for example, and can be determined by conversion using a standard polystyrene calibration curve.
The photosensitive resin composition of the present invention comprises (B) a polymerizable monomer having an aliphatic cyclic skeleton (preferably 4 to 15 carbon atoms, more preferably 5 to 12 carbon atoms). This can impart hydrophobicity to the curable material that can be formed, and can suppress a decrease in adhesion between the curable material and the substrate under high-temperature and high-humidity conditions.
(B) The ingredients preferably comprise: the polymerizable monomer having an aliphatic cyclic skeleton and having (preferably 2 or more) groups containing a polymerizable unsaturated double bond (preferably a (meth) acryloyl group in view of being polymerizable by a photopolymerization initiator) preferably has 2 to 3 groups containing a polymerizable unsaturated double bond in order to improve the crosslinking density and sensitivity and suppress swelling of a pattern after development.
(B) The component (C) preferably contains a polymerizable monomer represented by the following formula (3).
[ solution 15]
(in the formula (3), R6And R7Each independently is an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the following formula (4). n1 is 0 or 1, n2 is an integer of 0 to 2, and n1+ n2 is greater than or equal to 1 (preferably 2 or 3). n 1R6And n 2R7At least one (preferably 2 or 3) of the above groups is a group represented by the following formula (4). )
At R7Is 2In the case of (2), R7May be the same or different.
[ solution 16]
(in the formula (4), R9~R11Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and l is an integer of 0 to 10 (preferably 0, 1 or 2). )
(B) The component (C) more preferably contains a polymerizable monomer represented by the following formula (5).
[ solution 17]
Further, as the component (B), for example, the following polymerizable monomers can be used.
[ solution 18]
In the formula (12), R21~R24Each independently is an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the formula (4). n3 is an integer of 1 to 3 (preferably 2 or 3). n4 is an integer of 1 to 3 (preferably 2 or 3). n5 is 0 or 1, and n6 is 0 or 1. n5+ n6 is greater than or equal to 1 (preferably 2).
At R21When there are 2 or more, 2 or more R21May be the same or different.
At R22When there are 2 or more, 2 or more R22May be the same or different.
n 3R21At least one (preferably 2 or 3) of (a) and (b) is a group represented by the above formula (4).
n 4R22At least one (preferably 2 or 3) of (a) and (b) is a group represented by the above formula (4).
n 5R23And n 6R24At least one (preferably 2) of (a) and (b) is a group represented by the above formula (4).
R as formula (3)6And R7And R of formula (12)21~R24The aliphatic hydrocarbon group having 1 to 4 carbon atoms of (A) includes R of the formula (1)1And R2The same as the aliphatic hydrocarbon group having 1 to 4 carbon atoms.
R as formula (4)9~R11The aliphatic hydrocarbon group having 1 to 3 carbon atoms of (A) includes a group represented by formula (2) R3~R5The same as the aliphatic hydrocarbon group having 1 to 3 carbon atoms.
(B) The component (b) may be used alone or in combination of two or more.
The content of the component (B) is preferably 1 to 50 parts by mass relative to 100 parts by mass of the component (A). From the viewpoint of improving the hydrophobicity of the cured product, the amount is more preferably 3 to 50 parts by mass, and still more preferably 5 to 35 parts by mass.
In the case of within the above range, a practical concave-convex pattern can be easily obtained, and the residue after development of the unexposed portion can be easily suppressed.
Preferred examples of the component (C) include: benzophenone derivatives such as benzophenone, methyl o-benzoylbenzoate, 4-benzoyl-4' -methyldiphenylketone, dibenzylketone, and fluorenone;
acetophenone derivatives such as 2, 2' -diethoxyacetophenone, 2-hydroxy-2-methylpropiophenone, and 1-hydroxycyclohexyl phenyl ketone;
thioxanthone derivatives such as thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone and diethylthioxanthone;
benzil derivatives such as benzil, benzil dimethyl ketal, and benzil- β -methoxyethyl acetal;
benzoin derivatives such as benzoin and benzoin methyl ether; and
1-phenyl-1, 2-butanedione-2- (O-methoxycarbonyl) oxime, 1-phenyl-1, 2-propanedione-2- (O-ethoxycarbonyl) oxime, 1-phenyl-1, 2-propanedione-2- (O-benzoyl) oxime, 1, 3-diphenylpropanetrione-2- (O-ethoxycarbonyl) oxime, 1-phenyl-3-ethoxypropanetrione-2- (O-benzoyl) oxime, ethanone, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -, and oxime esters such as 1- (O-acetyloxime) and compounds represented by the following formula, but the oxime esters are not limited thereto.
[ solution 19]
In particular, oxime esters are preferable from the viewpoint of sensitivity.
(C) Component (C1) preferably contains a compound represented by the following formula (15) (hereinafter, also referred to as "component (C1)").
(C1) The component (C) is preferably a photosensitizer having higher sensitivity to active light than the component (C2) described later, and is preferably high sensitivity.
[ solution 20]
In the formula (15), R11AIs an alkyl group having 1 to 12 carbon atoms, and a1 is an integer of 0 to 5. R12AIs a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R13AAnd R14AEach independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), a phenyl group or a tolyl group. In the case where a1 is an integer of 2 or more, R11AEach may be the same or different.
R11APreferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group. a1 is preferably 1. R12APreferably an alkyl group having 1 to 4 carbon atoms, and more preferably an ethyl group. R13AAnd R14AEach of the alkyl groups is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
The compound represented by the formula (15) includes, for example, a compound represented by the following formula (15A), which is available as "IRGACURE OXE 02" manufactured by BASF japan.
[ solution 21]
The component (C) preferably contains (C2) a compound represented by the following formula (16) (hereinafter, also referred to as a component (C2)).
(C2) The component (C) is preferably a photosensitizer having a sensitivity to active light lower than that of the (C1) component, preferably a standard sensitivity.
[ solution 22]
In the formula (16), R21AIs an alkyl group having 1 to 12 carbon atoms, R22AAnd R23AEach independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), an alkoxy group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group or a tolyl group, and c1 is an integer of 0 to 5. In the case where c1 is an integer of 2 or more, R21AEach may be the same or different.
c1 is preferably 0. R22APreferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group. R23APreferably an alkoxy group having 1 to 12 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, and still more preferably a methoxy group or an ethoxy group.
Examples of the compound represented by the formula (16) include a compound represented by the following formula (16A), which is available as "G-1820 (PDO)" manufactured by Lambson.
[ solution 23]
(C) The component (b) may be used alone or in combination of two or more.
(C) The component (C) preferably contains one or more selected from the group consisting of the component (C1) and the component (C2).
Further, the component (C) preferably contains the component (C1) and the component (C2).
The content of the component (C) is preferably 0.1 to 20 parts by mass, more preferably 0.1 to 15 parts by mass, and still more preferably 0.2 to 10 parts by mass, relative to 100 parts by mass of the component (A).
In the case where the amount is within the above range, photocrosslinking tends to be uniform in the film thickness direction, and a practical uneven pattern tends to be obtained.
When the component (C1) is contained, the content of the component (C1) is usually 0.05 to 5.0 parts by mass, preferably 0.07 to 2.5 parts by mass, and more preferably 0.09 to 1.0 part by mass, based on 100 parts by mass of the component (A).
When the component (C2) is contained, the content of the component (C2) is usually 0.5 to 15.0 parts by mass, preferably 1.0 to 13.0 parts by mass, based on 100 parts by mass of the component (A).
When the component (C1) and the component (C2) are contained, the content of the component (C1) is preferably 0.05 to 5.0 parts by mass per 100 parts by mass of the component (a), and the content of the component (C2) is preferably 0.5 to 15.0 parts by mass per 100 parts by mass of the component (a).
When the component (C1) and the component (C2) are contained, the mass ratio of the content of the component (C1) to the content of the component (C2) is preferably 1:30 to 1:70, and more preferably 1:35 to 1: 65.
From the viewpoint of achieving both sensitivity and resolution, the component (D) preferably contains a compound represented by the following formula (31).
[ solution 24]
(in the formula (31), R61Each independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, or a halogen atom (preferably a fluorine atom), and n10 is an integer of 0 to 8 (preferably an integer of 1 to 4, more preferably 2,3, or 4). )
Examples of the alkyl group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 2 to 5 carbon atoms) include a methyl group, an ethyl group, a tert-butyl group, and an n-butyl group.
Examples of the alkoxy group having 1 to 10 (preferably 1 to 6, more preferably 2 to 5) carbon atoms include a butoxy group (e.g., n-butoxy group), a methoxy group, and an ethoxy group.
Examples of the aryl group having 6 to 18 carbon atoms (preferably 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms) include a phenyl group and a naphthyl group.
Examples of the heteroaryl group having 5 to 18 (preferably 5 to 12, more preferably 5 to 10) atoms include a pyridyl group, a quinolyl group, a carbazolyl group and the like.
From the viewpoint of satisfying both solubility in the photosensitive resin composition and photosensitive properties, the component (D) is preferably dialkoxyanthracene (e.g., 9, 10-dialkoxyanthracene) which may have a substituent, and is preferably at least one selected from the group consisting of dibutoxyanthracene (e.g., 9, 10-dibutoxyanthracene), dimethoxyanthracene (e.g., 9, 10-dimethoxyanthracene), diethoxyanthracene (e.g., 9, 10-diethoxyanthracene), and diethoxyethylanthracene (e.g., 9, 10-dimethoxy-2-ethylanthracene).
Examples of the substituent include methyl, ethyl, tert-butyl, n-butyl and the like.
(D) The component (b) may be used alone or in combination of two or more.
The content of the component (D) is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, and still more preferably 0.3 to 5 parts by mass, relative to 100 parts by mass of the component (A).
When the amount is within the above range, the solubility of the photosensitive resin composition and the photosensitive property can be improved at the same time.
The photosensitive resin composition of the present invention contains (E) a solvent.
Examples of the component (E) include N-methyl-2-pyrrolidone, γ -butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, benzyl acetate, N-butyl acetate, ethyl ethoxypropionate, methyl 3-methoxypropionate, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, hexamethylphosphoramide, sulfolane, cyclohexanone, cyclopentanone, diethyl ketone, diisobutyl ketone, methyl amyl ketone, and N-dimethylmorpholine, and the component (E) is not particularly limited as long as the other components can be dissolved sufficiently.
Among them, N-methyl-2-pyrrolidone, γ -butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, N-dimethylformamide, and N, N-dimethylacetamide are preferably used from the viewpoint of excellent solubility of each component and coatability when forming a photosensitive resin film.
Further, as the component (E), a compound represented by the following formula (21) can be used.
[ solution 25]
(in the formula, R41~R43Each independently is an alkyl group having 1 to 10 carbon atoms. )
As R in formula (21)41~R43Examples of the alkyl group having 1 to 10 carbon atoms (preferably 1 to 3 carbon atoms, more preferably 1 or 3 carbon atoms) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.
The compound represented by the formula (21) is preferably 3-methoxy-N, N-dimethylpropionamide (for example, trade name "KJCMPA-100" (manufactured by KJ chemical Co., Ltd.)).
(E) The component (b) may be used alone or in combination of two or more.
(E) The content of the component (A) is not particularly limited, but is generally 50 to 1000 parts by mass per 100 parts by mass of the component (A).
The photosensitive resin composition of the present invention may further contain (F) a thermal polymerization initiator (hereinafter, also referred to as "component (F)") from the viewpoint of promoting the polymerization reaction.
As the component (F), the following compounds are preferable: the components (B) are not decomposed by heating (drying) for removing the solvent during film formation, but are decomposed by heating during curing to generate radicals, thereby promoting polymerization of the components (B) or the components (a) and (B).
(F) The component (B) is preferably a compound having a decomposition point of 110 ℃ or higher and 200 ℃ or lower, and more preferably a compound having a decomposition point of 110 ℃ or higher and 175 ℃ or lower, from the viewpoint of promoting the polymerization reaction at a lower temperature.
Specific examples thereof include ketone peroxides such as methyl ethyl ketone peroxide; peroxyketals such as 1, 1-bis (t-hexylperoxy) -3,3, 5-trimethylcyclohexane, 1-bis (t-hexylperoxy) cyclohexane, and 1, 1-bis (t-butylperoxy) cyclohexane; hydrogen peroxide such as 1,1,3, 3-tetramethylbutylhydroperoxide, cumene hydroperoxide, p-menthane hydroperoxide, etc.; dialkyl peroxides such as dicumyl peroxide and di-t-butyl peroxide; diacyl peroxides such as dilauroyl peroxide and dibenzoyl peroxide; peroxydicarbonates such as bis (4-t-butylcyclohexyl) peroxydicarbonate and bis (2-ethylhexyl) peroxydicarbonate; peroxy esters such as t-butylperoxy-2-ethylhexanoate, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy benzoate, and 1,1,3, 3-tetramethylbutylperoxy-2-ethylhexanoate; bis (1-phenyl-1-methylethyl) peroxide, and the like. Commercially available products include trade names "Percumyl D", "Percumyl P" and "Percumyl H" (manufactured by Nikkiso Co., Ltd.).
When the component (F) is contained, the content of the component (F) is preferably 0.1 to 20 parts by mass per 100 parts by mass of the component (a), more preferably 0.2 to 20 parts by mass in order to ensure good flux resistance, and still more preferably 0.3 to 10 parts by mass in view of suppressing a decrease in solubility due to decomposition during drying.
The photosensitive resin composition of the present invention may further contain a coupling agent (bonding aid), a surfactant or leveling agent, a rust inhibitor, a crosslinking agent other than the component (B), a sensitizer, a polymerization inhibitor, and the like.
In general, the coupling agent reacts with the component (a) to crosslink in the heat treatment after development, or the coupling agent itself polymerizes in the step of heat treatment. This can further improve the adhesion between the obtained cured product and the substrate.
As a preferable silane coupling agent, a compound having a urea bond (-NH-CO-NH-) can be mentioned. Thereby, even when curing is performed at a low temperature of 200 ℃ or lower, the adhesiveness to the substrate can be further improved.
The compound represented by the following formula (13) is more preferable because it exhibits excellent adhesiveness when cured at a low temperature.
[ solution 26]
(in the formula (13), R31And R32Each independently an alkyl group having 1 to 5 carbon atoms. a is an integer of 1 to 10, and b is an integer of 1 to 3. )
Specific examples of the compound represented by formula (13) include ureidomethyltrimethoxysilane, ureidomethyltriethoxysilane, 2-ureidoethyltrimethoxysilane, 2-ureidoethyltriethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 4-ureidobutyltrimethoxysilane, and 4-ureidobutyltriethoxysilane, and 3-ureidopropyltriethoxysilane is preferable.
As the silane coupling agent, a silane coupling agent having a hydroxyl group or a glycidyl group can be used. When a silane coupling agent having a hydroxyl group or a glycidyl group and a silane coupling agent having a urea bond in the molecule are used in combination, the adhesion of a cured product to a substrate during low-temperature curing can be further improved.
Examples of the silane coupling agent having a hydroxyl group or a glycidyl group include methylphenylsilane diol, ethylphenylsilane diol, n-propylphenylsilane diol, isopropylphenylsilane diol, n-butylphenyl silane diol, isobutylphenylsilane diol, tert-butylphenyl silane diol, diphenylsilane diol, ethylmethylphenylsilanol, n-propylmethylphenylsilanol, isopropylmethylphenylsilanol, n-butylmethylphenylsilanol, isobutylmethylphenylsilanol, tert-butylmethylphenylsilanol, ethyl-n-propylphenylsilanol, ethylisopropylphenylsilanol, n-butyleethylphenylsilanol, isobutylethylphenylsilanol, tert-butyleethylphenylsilanol, methyldiphenylsilanol, ethyldiphenylsilanol, n-propyldiphenylsilanol, isopropyldiphenylsilanol, n-butyldiphenylsilanol, isobutyl diphenylsilanol, tert-butyl diphenylsilanol, phenylsilane triol, 1, 4-bis (trihydroxysilyl) benzene, 1, 4-bis (methyldihydroxysilyl) benzene, 1, 4-bis (ethyldihydroxysilyl) benzene, 1, 4-bis (propyldihydroxysilyl) benzene, 1, 4-bis (butyldihydroxysilyl) benzene, 1, 4-bis (dimethylhydroxysilyl) benzene, 1, 4-bis (diethylhydroxysilyl) benzene, 1, 4-bis (dipropylhydroxysilyl) benzene, 1, 4-bis (dibutylhydroxysilyl) benzene, and a compound represented by the following formula (14). Among them, the compound represented by the formula (14) is particularly preferable in order to further improve the adhesiveness to the substrate.
[ solution 27]
(in the formula (14), R33Is a 1-valent organic radical having a hydroxyl group or a glycidyl group, R34And R35Each independently an alkyl group having 1 to 5 carbon atoms. c is an integer of 1 to 10, and d is an integer of 1 to 3. )
Examples of the compound represented by the formula (14) include hydroxymethyltrimethoxysilane, hydroxymethyltriethoxysilane, 2-hydroxyethyltrimethoxysilane, 2-hydroxyethyltriethoxysilane, 3-hydroxypropyltrimethoxysilane, 3-hydroxypropyltriethoxysilane, 4-hydroxybutyltrimethoxysilane and 4-hydroxybutyltriethoxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, 2-glycidoxyethyltrimethoxysilane, 2-glycidoxyethyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 4-glycidoxybutyltrimethoxysilane, 4-glycidoxybutyltriethoxysilane and the like.
The silane coupling agent having a hydroxyl group or a glycidyl group further preferably contains a group having a nitrogen atom, and is preferably a silane coupling agent further having an amino group or an amide bond.
Examples of the silane coupling agent having a further amino group include bis (2-hydroxymethyl) -3-aminopropyltriethoxysilane, bis (2-hydroxymethyl) -3-aminopropyltrimethoxysilane, bis (2-glycidoxymethyl) -3-aminopropyltriethoxysilane, bis (2-hydroxymethyl) -3-aminopropyltrimethoxysilane and the like.
Examples of the silane coupling agent further having an amide bond include R36-(CH2)e-CO-NH-(CH2)f-Si(OR37)3(R36Is a hydroxyl group or a glycidyl group, e and f are each independently an integer of 1 to 3, R37Methyl, ethyl or propyl) and the like.
The silane coupling agent may be used alone or in combination of two or more.
When a silane coupling agent is used, the content of the silane coupling agent is preferably 0.1 to 20 parts by mass, more preferably 0.3 to 10 parts by mass, and still more preferably 1 to 10 parts by mass, per 100 parts by mass of the component (a).
By including a surfactant or a leveling agent, coating properties (for example, suppression of streaks (uneven film thickness)) and developing properties can be improved.
Examples of the surfactant and the leveling agent include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, and polyoxyethylene octylphenol ether, and examples of commercially available products include trade names "MEGAFAX F171", "F173", and "R-08" (manufactured by DIC corporation); trade names "FLUORAD FC 430" and "FC 431" (manufactured by Sumitomo 3M Co., Ltd.); the trade names "Organosiloxane Polymer (Organosiloxane Polymer) KP 341", "KBM 303", "KBM 403" and "KBM 803" (manufactured by shin-Etsu chemical Co., Ltd.).
The surfactant and the leveling agent may be used alone or in combination of two or more.
When the surfactant or the leveling agent is contained, the content of the surfactant or the leveling agent is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, and further preferably 0.05 to 3 parts by mass, relative to 100 parts by mass of the component (a).
By including the rust inhibitor, corrosion of copper and copper alloy can be suppressed, and discoloration can be prevented.
Examples of the rust inhibitor include triazole derivatives and tetrazole derivatives.
Examples of the rust inhibitor include 5-aminotetrazole (e.g., 5-amino-1H-tetrazole), benzotriazole, 1-hydroxybenzotriazole, 1H-benzotriazole-1-acetonitrile, benzotriazole-5-carboxylic acid, 1H-benzotriazole-1-methanol, carboxybenzotriazole, mercaptobenzotriazoleOxazoles, and the like. Among them, 5-aminotetrazole, benzotriazole or 1-hydroxybenzotriazole is preferable.
One kind of rust inhibitor may be used alone, or two or more kinds may be used in combination.
When a rust inhibitor is used, the content of the rust inhibitor is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and still more preferably 0.5 to 3 parts by mass, per 100 parts by mass of the component (a).
By including a crosslinking agent other than the component (B), the photosensitive characteristics, the characteristics of the cured product, and the like can be flexibly adjusted, and particularly, the characteristics of the cured product can be greatly changed.
Examples of the crosslinking agent other than the component (B) include: diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 1, 4-butanediol diacrylate, 1, 6-hexanediol diacrylate, 1, 4-butanediol dimethacrylate, 1, 6-hexanediol dimethacrylate, trimethylolpropane diacrylate, trimethylolpropane triacrylate, trimethylolpropane dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate,
tetramethylolmethane tetraacrylate, tetramethylolmethane tetramethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated isocyanuric acid triacrylate, ethoxylated isocyanuric acid trimethacrylate, acryloxyethyl isocyanurate, methacryloxyethyl isocyanurate, and the like.
(B) The crosslinking agent other than the component (a) may be used alone or in combination of two or more.
When the crosslinking agent other than the component (B) is contained, the content of the crosslinking agent other than the component (B) is preferably 0.01 to 20 parts by mass, more preferably 0.05 to 15 parts by mass, and still more preferably 1 to 12 parts by mass, based on 100 parts by mass of the component (A).
Examples of sensitizers include: melilone, benzoin, 2-methylbenzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether, 2-t-butylanthraquinone, 1, 2-benzo-9, 10-anthraquinone, methylanthraquinone, 4' -bis- (diethylamino) benzophenone, acetophenone, benzophenone, thioxanthone, 1, 5-acenaphthene, 2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl- [4- (methylthio) phenyl ] -2-morpholino-1-propanone, diacetyl benzil, benzil dimethyl ketal, benzil diethyl ketal, diphenyl disulfide, anthracene, phenanthrenequinone, riboflavin tetrabutyrate, acridine orange, erythrosine, Phenanthrenequinone, 2-isopropylthioxanthone, 2, 6-bis (p-diethylaminobenzylidene) -4-methyl-4-azacyclohexanone, 6-bis (p-dimethylaminobenzylidene) -cyclopentanone, 2, 6-bis (p-diethylaminobenzylidene) -4-phenylcyclohexanone, aminostyryl ketone, 3-ketocoumarin compound, bishydrocoumarin compound, N-phenylglycine, N-phenyldiethanolamine and 3,3 ', 4, 4' -tetrakis (t-butylperoxycarbonyl) benzophenone, a compound represented by the following formula, and the like.
[ solution 28]
One sensitizer may be used alone, or two or more sensitizers may be used in combination.
When the sensitizer is contained, the amount of the sensitizer is preferably 0.1 to 1.5 parts by mass, and more preferably 0.2 to 1.2 parts by mass, per 100 parts by mass of the component (a).
By containing a polymerization inhibitor, good storage stability can be ensured.
Examples of the polymerization inhibitor include a radical polymerization inhibitor and a radical polymerization inhibitor.
Examples of the polymerization inhibitor include 1,4, 4-trimethyl-2, 3-diazabicyclo [3.2.2] -non-2-ene-2, 3-dioxide, p-methoxyphenol, diphenyl-p-benzoquinone, hydroquinone, pyrogallol, phenothiazine, resorcinol, o-dinitrobenzene, p-dinitrobenzene, m-dinitrobenzene, phenanthrenequinone, N-phenyl-2-naphthylamine, Cupferron (Cupferron), 2, 5-toluenequinone, tannic acid, p-benzylaminophenol, and nitrosamines.
The polymerization inhibitor may be used alone or in combination of two or more.
When the polymerization inhibitor is contained, the content of the polymerization inhibitor is preferably 0.01 to 30 parts by mass, more preferably 0.01 to 10 parts by mass, and still more preferably 0.05 to 5 parts by mass, relative to 100 parts by mass of the component (a), from the viewpoints of storage stability of the photosensitive resin composition and heat resistance of the resulting cured product.
The photosensitive resin composition of the present invention is essentially composed of components (a) to (E) and optionally component (F), a coupling agent, a surfactant, a leveling agent, a rust inhibitor, a crosslinking agent other than component (B), a sensitizer and a polymerization inhibitor, and may further contain unavoidable impurities within a range not to impair the effects of the present invention.
The photosensitive resin composition of the present invention may contain, for example, not less than 80 mass%, not less than 90 mass%, not less than 95 mass%, not less than 98 mass%, or 100 mass% of the total amount of the photosensitive resin composition
(A) Components (A) to (E),
(A) Component (1) to (F), or
(A) Components (A) to (E), and optionally component (F), a coupling agent, a surfactant, a leveling agent, a rust preventive, a crosslinking agent other than component (B), a sensitizer and a polymerization inhibitor.
The cured product of the present invention can be obtained by curing the photosensitive resin composition.
The cured product of the present invention can be used as a patterned cured product and also as an unpatterned cured product.
The thickness of the cured product of the present invention is preferably 5 to 20 μm.
The method for producing a patterned cured product of the present invention comprises the steps of: a step of forming a photosensitive resin film by coating the photosensitive resin composition on a substrate and drying the composition; a step of obtaining a resin film by pattern-exposing a photosensitive resin film; a step of developing the resin film after pattern exposure with an organic solvent to obtain a pattern resin film; and a step of performing heat treatment on the pattern resin film.
Thereby, a pattern cured product can be obtained.
The method for producing a non-patterned cured product includes, for example, a step of forming the photosensitive resin film and a step of performing a heat treatment. The method may further comprise a step of performing exposure.
Examples of the substrate include a semiconductor substrate such as a glass substrate or an Si substrate (silicon wafer); TiO 22Substrate and SiO2Metal oxide insulator substrates such as substrates; silicon nitride substrates, copper alloy substrates, and the like.
The coating method is not particularly limited, and can be performed using a spin coater or the like.
Drying can be performed using a hot plate, an oven, or the like.
The drying temperature is preferably 90 to 150 ℃, and more preferably 90 to 120 ℃ from the viewpoint of ensuring the solubility contrast.
The drying time is preferably 30 seconds to 5 minutes.
The drying may be carried out 2 or more times.
Thus, a photosensitive resin film formed by forming the photosensitive resin composition into a film shape can be obtained.
The thickness of the photosensitive resin film is preferably 5 to 100 μm, more preferably 6 to 50 μm, and still more preferably 7 to 30 μm.
The pattern exposure is, for example, exposure to a predetermined pattern through a photomask.
The active light to be irradiated includes ultraviolet rays such as i-rays and h-rays, visible rays, and radiation rays, and i-rays are preferable.
As the exposure apparatus, a parallel exposure machine, a projection exposure machine, a stepper exposure machine, a scanner exposure machine, or the like can be used.
By performing development, a patterned resin film (pattern resin film) can be obtained. In general, when a negative photosensitive resin composition is used, unexposed portions are removed with a developer.
The organic solvent used as the developing solution may be a good solvent for the photosensitive resin film alone or a good solvent and a poor solvent mixed appropriately as the developing solution.
Examples of the good solvent include N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N-dimethylacetamide, N-dimethylformamide, dimethyl sulfoxide, γ -butyrolactone, α -acetyl- γ -butyrolactone, cyclopentanone, and cyclohexanone.
Examples of the poor solvent include toluene, xylene, methanol, ethanol, isopropanol, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and water.
A surfactant may be added to the developer. The amount of the additive is preferably 0.01 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass, based on 100 parts by mass of the developer.
The developing time can be, for example, 2 times the time taken for the photosensitive resin film to be immersed and completely dissolved.
The developing time is preferably 10 seconds to 15 minutes, more preferably 10 seconds to 5 minutes, and still more preferably 20 seconds to 5 minutes from the viewpoint of productivity, depending on the component (a) used.
After development, washing may be performed by a washing solution.
The rinse solution may be used alone or in a suitable mixture of distilled water, methanol, ethanol, isopropanol, toluene, xylene, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and the like, or may be used in combination in stages.
By heat-treating the pattern resin film, a pattern cured product can be obtained.
(A) The polyimide precursor of the component (a) undergoes a dehydration ring-closure reaction in the heat treatment step, and usually forms a corresponding polyimide.
The temperature of the heat treatment is preferably not more than 250 ℃, more preferably 120 to 250 ℃, and further preferably not more than 200 ℃ or 160 to 200 ℃.
By setting the range to the above range, damage to the substrate and the device can be suppressed to a small extent, the device can be produced with a high yield, and energy saving of the process can be achieved.
The time of the heat treatment is preferably 5 hours or less, and more preferably 30 minutes to 3 hours.
When the amount is within the above range, the crosslinking reaction or the dehydration ring-closing reaction can be sufficiently performed.
The atmosphere for the heat treatment may be in the air or in an inert atmosphere such as nitrogen, and is preferably a nitrogen atmosphere from the viewpoint of preventing the pattern resin film from being oxidized.
Examples of the apparatus used for the heat treatment include a quartz tube furnace, a hot plate, a rapid annealing furnace, a vertical diffusion furnace, an infrared curing furnace, an electron beam curing furnace, and a microwave curing furnace.
The cured product of the present invention can be used as a passivation film, a buffer coating film, an interlayer insulating film, a cover coat, a surface protective film, or the like.
By using one or more selected from the group consisting of the above-described passivation film, buffer coating film, interlayer insulating film, coverlay film, surface protective film, and the like, it is possible to manufacture highly reliable electronic components such as semiconductor devices, multilayer wiring boards, various electronic devices, and stacked devices (multi-chip fan-out type wafer level packages and the like).
An example of a manufacturing process of a semiconductor device as an electronic component of the present invention will be described with reference to the drawings.
Fig. 1 is a process diagram for manufacturing a semiconductor device having a multilayer wiring structure as an electronic component according to an embodiment of the present invention.
In fig. 1, a semiconductor substrate 1 such as an Si substrate having circuit elements is covered with a protective film 2 such as a silicon oxide film except for predetermined portions of the circuit elements, and a first conductor layer 3 is formed on the exposed circuit elements. Then, an interlayer insulating film 4 is formed on the semiconductor substrate 1.
Next, a photosensitive resin layer 5 of a chlorinated rubber type, a phenol novolac type, or the like is formed on the interlayer insulating film 4, and a window 6A is provided by a known photolithography technique so as to expose a predetermined portion of the interlayer insulating film 4.
The interlayer insulating film 4 exposed by the window 6A is selectively etched to provide a window 6B.
Next, the photosensitive resin layer 5 is completely removed by using an etching solution that does not etch the first conductor layer 3 exposed through the window 6B but etches only the photosensitive resin layer 5.
Further, a second conductor layer 7 is formed to be electrically connected to the first conductor layer 3 using a known photolithography technique.
In the case of forming a multilayer wiring structure having 3 or more layers, the above-described steps can be repeated to form each layer.
Next, the photosensitive resin composition is used to form the surface protection film 8 by opening the window 6C by pattern exposure. The surface protective film 8 protects the second conductor layer 7 from external stress, α -rays, and the like, and the resulting semiconductor device is excellent in reliability.
In the above examples, the photosensitive resin composition of the present invention can be used to form an interlayer insulating film.
Examples
The present invention will be described in more detail below based on examples and comparative examples. The present invention is not limited to the following examples.
Synthesis example 1 (Synthesis of A1)
7.07g of 3,3 ', 4, 4' -diphenylethertetracarboxylic dianhydride (ODPA) and 4.12g of 2,2 '-dimethylbiphenyl-4, 4' -Diamine (DMAP) were dissolved in 30g of N-methyl-2-pyrrolidone (NMP), and stirred at 30 ℃ for 4 hours and then stirred at room temperature overnight to obtain a polyamic acid. 9.45g of trifluoroacetic anhydride was added thereto under water cooling, and stirred at 45 ℃ for 3 hours, to which 7.08g of 2-hydroxyethyl methacrylate (HEMA) was added. The reaction solution was added dropwise to distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain a polyimide precursor a 1.
The number average molecular weight was determined by Gel Permeation Chromatography (GPC) method in terms of standard polystyrene under the following conditions. The number average molecular weight of A1 was 40,000.
The measurement was performed using 1mL of a solution of the solvent [ Tetrahydrofuran (THF)/Dimethylformamide (DMF) ═ 1/1 (volume ratio) ] relative to 0.5mg of a 1.
A measuring device: l4000UV manufactured by Hitachi, Inc. of Detector
A pump: l6000 manufactured by Hitachi Kabushiki Kaisha
C-R4A Chromatopac, manufactured by Shimadzu corporation
The measurement conditions were as follows: column Gelpack GL-S300 MDT-5X 2
Eluent: THF/DMF 1/1 (volumetric ratio)
LiBr(0.03mol/L),H3PO4(0.06mol/L)
Flow rate: 1.0mL/min, detector: UV270nm
Further, the esterification ratio of a1 (the reaction ratio between carboxyl groups of ODPA and HEMA) was calculated by NMR measurement under the following conditions. The esterification rate was 80 mol% relative to all carboxyl groups of the polyamic acid (the remaining 20 mol% were carboxyl groups).
Measurement equipment: AV400M manufactured by Bruker BioSpin
Magnetic field strength: 400MHz
Reference substance: tetramethylsilane (TMS)
Solvent: dimethyl sulfoxide (DMSO)
Examples 1 to 9 and comparative examples 1 to 3
(preparation of photosensitive resin composition)
Photosensitive resin compositions of examples 1 to 9 and comparative examples 1 to 3 were prepared by using the components and blending amounts shown in tables 1 and 2. The blending amounts in tables 1 and 2 are parts by mass of the respective components with respect to 100 parts by mass of a 1.
The components used are as follows. As the component (a), a1 obtained in synthesis example 1 was used.
(B) The components: polymerizable monomer having aliphatic cyclic skeleton
B1: A-DCP (Dicidodecane dimethanol diacrylate, produced by Mitsumura chemical Co., Ltd., described below as a compound represented by formula B1)
[ solution 29]
(C) The components: photopolymerization initiator
C1: IRUGCURE OXE 02 (ethanone, manufactured by BASF Japan K.K., 1- [ 9-Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (O-acetyloxime))
C2: g-1820(PDO) (1-phenyl-1, 2-propanedione-2- (O-ethoxycarbonyl) oxime, manufactured by Lambson K.K.)
(D) Composition (I)
D1: 9, 10-dibutoxyanthracene (Kawasaki chemical industry Co., Ltd.)
(E) The components: solvent(s)
E1: n-methyl-2-pyrrolidone
E2: KJCMPA-100 (a compound represented by the following formula E2, manufactured by KJ Chemicals Co., Ltd.)
[ solution 30]
(F) The components: thermal polymerization initiator
F1: percumyl D (bis (1-phenyl-1-methylethyl) peroxide, manufactured by Nichikoku corporation, Compound represented by the following formula)
[ solution 31]
(B) Crosslinking agents other than the component (A)
ATM-4E: ethoxylated pentaerythritol tetraacrylate (Compound represented by the following formula (n11+ n12+ n13+ n 14: 4, manufactured by shin-Komura chemical Co., Ltd.))
[ solution 32]
Sensitizers
BCIM: 2,2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole (a compound represented by the following formula, manufactured by Hampford Research Co., Ltd.)
[ solution 33]
Leuco dye LCV: colorless crystal violet (a compound represented by the following formula, manufactured by Shantian chemical industries, Ltd.)
[ chemical 34]
EMK: 4, 4' -bis (diethylamino) benzophenone
Polymerization inhibitor
Taobn: 1,4, 4-trimethyl-2, 3-diazabicyclo [3.2.2] -non-2-ene-2, 3-dioxide (product of Hampford Research Co., Ltd.)
Rust inhibitor
5 Atz: 5-amino-1H-tetrazole (manufactured by Tokyo Kasei Kaisha)
Adhesion promoter
UCT-801: 3-ureidopropyltriethoxysilane (manufactured by United Chemical Technologies Co., Ltd.)
(measurement of residual film ratio after development 1)
The obtained photosensitive resin composition was spin-coated on a silicon wafer using a coating apparatus Act8 (manufactured by Tokyo Electron Co., Ltd.), dried at 100 ℃ for 2 minutes and then dried at 110 ℃ for 2 minutes to form a photosensitive resin film having a dry film thickness of 7 to 15 μm.
The developing time was set to 2 times the time until the obtained photosensitive resin film was immersed in cyclopentanone and completely dissolved.
Further, a photosensitive resin film was produced in the same manner as described above, and the obtained photosensitive resin film was irradiated with 200mJ/cm using an i-line stepper FPA-3000iW (manufactured by Canon corporation)2And (4) performing exposure on the i line.
After the exposed resin film was subjected to spincoating immersion development in cyclopentanone for the above-described development time using Act8, washing was performed with Propylene Glycol Monomethyl Ether Acetate (PGMEA), and the resin film was obtained.
The film thickness after heating on a hot plate at 110 ℃ for 2 minutes and the film thickness after development were measured by scraping a part of the film to expose the silicon wafer, and measuring the height from the exposed silicon wafer surface to the film surface using a probe profilometer Dektak150 (manufactured by Bruker Co., Ltd.) (the same applies to the measurement of the film thickness).
The film thickness after development was divided by the film thickness after heating on a hot plate at 110 ℃ for 2 minutes to obtain the residual film ratio after development as a percentage. A represents a residual film ratio after development of 55 to 100%, B represents a residual film ratio of 40% or more and less than 55%, and C represents a residual film ratio of 0% or more and less than 40%. The results are shown in tables 1 and 2.
(preparation of cured product 1)
In examples 1 to 9, the resin film obtained in measurement 1 of the residual film rate after development was heated at 175 ℃ for 1 hour under a nitrogen atmosphere using a vertical diffusion furnace μ -TF (manufactured by Thermo System Co., Ltd.) to obtain cured products (film thickness after curing: 7 to 10 μm).
In examples 1 to 9, good cured products were obtained.
(measurement of residual film ratio after development 2)
The photosensitive resin composition is spin-coated on a silicon wafer using a coating apparatus Act8, dried at 100 ℃ for 2 minutes, and then dried at 110 ℃ for 2 minutes to form a photosensitive resin film having a dry film thickness of 7 to 15 μm.
The developing time was set to 2 times the time until the obtained photosensitive resin film was immersed in cyclopentanone and completely dissolved.
A photosensitive resin film was prepared in the same manner as described above, and the obtained photosensitive resin film was irradiated with 200mJ/cm light from a mask aligner MA-8(SUSS MicroTec) using an h-line bandpass filter2And (4) exposing the substrate.
After the exposed resin film was subjected to spin immersion development in cyclopentanone for the above-described development time using Act8, rinsing washing was performed with PGMEA to obtain a resin film.
The film thickness after heating on a hot plate at 110 ℃ for 2 minutes and the film thickness after development were measured in the same manner as in measurement 1 of the residual film rate after development.
The film thickness after development was divided by the film thickness after heating on a hot plate at 110 ℃ for 2 minutes to obtain the residual film ratio after development as a percentage. A represents a residual film ratio after development of 55 to 100%, B represents a residual film ratio of 40% or more and less than 55%, and C represents a residual film ratio of 0% or more and less than 40%. The results are shown in tables 1 and 2.
(preparation of cured product 2)
In examples 1 to 9, the resin film obtained in measurement 2 of the residual film rate after development was heated at 175 ℃ for 1 hour in a nitrogen atmosphere using a vertical diffusion furnace μ -TF to obtain cured products (film thickness after curing: 7 to 10 μm).
In examples 1 to 9, good cured products were obtained.
(evaluation of Pattern formation)
The photosensitive resin composition is spin-coated on a silicon wafer using a coating apparatus Act8, dried at 100 ℃ for 2 minutes, and then dried at 110 ℃ for 2 minutes to form a photosensitive resin film having a dry film thickness of 7 to 15 μm.
The developing time was set to 2 times the time taken for the obtained photosensitive resin film to be immersed in cyclopentanone until completely dissolved.
A photosensitive resin film was prepared in the same manner as described above, and the obtained photosensitive resin film was irradiated with 500mJ/cm light in a predetermined pattern (line and space patterns of 10 μm) using an h-line bandpass filter by a mask aligner MA-8(SUSS MicroTec Co., Ltd.)2And (4) exposing the substrate.
After the exposed resin film was subjected to spincoating immersion development in cyclopentanone for the above-described development time using Act8, washing was performed with PGMEA to obtain a patterned resin film.
The obtained pattern resin film was observed with an optical microscope, and a case where the line patterns were not peeled off was defined as a, a case where 1 line pattern was peeled off was defined as B, and a case where the pattern could not be formed was defined as C. The results are shown in tables 1 and 2.
(production of cured Pattern)
The obtained pattern resin film was heated at 175 ℃ for 1 hour in a nitrogen atmosphere using a vertical diffusion furnace μ -TF to obtain a pattern cured product (film thickness after curing: 10 μm).
In examples 1 to 9, good cured products were obtained.
[ Table 1]
[ Table 2]
Industrial applicability
The photosensitive resin composition of the present invention can be used for an interlayer insulating film, a cover coat, a surface protective film, and the like, and the interlayer insulating film, the cover coat, or the surface protective film of the present invention can be used for an electronic component, and the like.
Although several embodiments and/or examples of the present invention have been described in detail, those skilled in the art will readily appreciate that many modifications are possible in the embodiments and/or examples without materially departing from the novel teachings and advantages of this invention. Accordingly, such many variations are intended to be included within the scope of the present invention.
The documents described in the present specification and the applications underlying the paris convention-based priority of the present application are incorporated herein in their entirety.
Claims (17)
1. A photosensitive resin composition comprising:
(A) a polyimide precursor having a polymerizable unsaturated bond,
(B) A polymerizable monomer having an aliphatic cyclic skeleton,
(C) A photopolymerization initiator,
(D) A compound containing an anthracene structure, and
(E) a solvent.
2. The photosensitive resin composition according to claim 1, wherein the component (A) is a polyimide precursor having a structural unit represented by the following formula (1),
[ solution 35]
In the formula (1), X1Is a 4-valent radical having more than 1 aromatic group, -COOR1The radicals and the-CONH-radicals being in ortho-position to one another, -COOR2The radical and the-CO-radical being in the ortho position relative to one another, Y1Is a 2-valent aromatic radical, R1And R2Each independently represents a hydrogen atom, a group represented by the following formula (2) or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, R1And R2At least one of which is a group represented by the formula (2),
[ solution 36]
In the formula (2), R3~R5Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and m is an integer of 1 to 10.
3. The photosensitive resin composition according to claim 1 or 2, the component (B) comprising: a polymerizable monomer having a group containing a polymerizable unsaturated double bond and having an aliphatic cyclic skeleton.
4. The photosensitive resin composition according to claim 3, wherein the component (B) is: a polymerizable monomer having 2 or more groups containing a polymerizable unsaturated double bond and having an aliphatic cyclic skeleton.
5. The photosensitive resin composition according to any one of claims 1 to 3, wherein the component (B) comprises a polymerizable monomer represented by the following formula (3),
[ solution 37]
In the formula (3), R6And R7Each independently an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the following formula (4), n1 is 0 or 1, n2 is an integer of 0 to 2, n1+ n2 is 1 or more, and n 1R are present6And n 2R7At least one of which is a group represented by the following formula (4),
[ solution 38]
In the formula (4), R9~R11Each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, l is 0 to 10An integer number.
6. The photosensitive resin composition according to claim 5, wherein n1+ n2 is 2 or 3.
8. The photosensitive resin composition according to any one of claims 1 to 7, wherein the component (D) comprises a compound represented by the following formula (31),
[ solution 40]
In the formula (31), R61Each independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms or a halogen atom, and n10 is an integer of 0 to 8.
9. The photosensitive resin composition according to any one of claims 1 to 7, wherein the component (D) is one or more selected from the group consisting of dibutoxyanthracene, dimethoxyanthracene, diethoxyanthracene, and diethoxyethylanthracene.
10. The photosensitive resin composition according to any one of claims 1 to 9, further comprising (F) a thermal polymerization initiator.
11. The photosensitive resin composition according to any one of claims 1 to 10, which is for panel-level packaging.
12. A method for producing a pattern cured product, comprising the steps of:
a step of forming a photosensitive resin film by applying the photosensitive resin composition according to any one of claims 1 to 11 onto a substrate and drying the composition;
a step of obtaining a resin film by pattern-exposing the photosensitive resin film;
a step of obtaining a pattern resin film by developing the pattern-exposed resin film with an organic solvent; and
and a step of heat-treating the pattern resin film.
13. The method for producing a patterned cured product according to claim 12, wherein the temperature of the heat treatment is 200 ℃ or lower.
14. A cured product obtained by curing the photosensitive resin composition according to any one of claims 1 to 11.
15. The cured product according to claim 14, which is a pattern cured product.
16. An interlayer insulating film, a cap coat or a surface protective film produced by using the cured product according to claim 14 or 15.
17. An electronic component comprising the interlayer insulating film, the covercoat, or the surface protective film of claim 16.
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JP2014214186A (en) * | 2013-04-23 | 2014-11-17 | 三洋化成工業株式会社 | Active energy ray-curable resin composition |
JP2018084626A (en) * | 2016-11-22 | 2018-05-31 | 日立化成デュポンマイクロシステムズ株式会社 | Photosensitive resin composition, method for producing patterned cured film, cured film, interlayer insulation film, cover coat layer, surface protective film and electronic component |
WO2018100640A1 (en) * | 2016-11-29 | 2018-06-07 | 日立化成株式会社 | Photosensitive resin composition, photosensitive element, method for producing substrate with resist pattern, and method for producing printed wiring board |
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JP2008111470A (en) | 2006-10-30 | 2008-05-15 | Nissan Motor Co Ltd | Mode change-over shift control device for continuously variable transmission |
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JP5504735B2 (en) * | 2009-07-31 | 2014-05-28 | 日立化成デュポンマイクロシステムズ株式会社 | Positive photosensitive resin composition, pattern cured film manufacturing method, and electronic component |
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JP2016199662A (en) | 2015-04-09 | 2016-12-01 | 日立化成デュポンマイクロシステムズ株式会社 | Resin composition comprising polyimide precursor, method for producing cured film and patterned cured film using the same, and electronic component |
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CN102636957A (en) * | 2011-02-14 | 2012-08-15 | 住友化学株式会社 | Colored photosensitive resin composition and compound |
JP2014214186A (en) * | 2013-04-23 | 2014-11-17 | 三洋化成工業株式会社 | Active energy ray-curable resin composition |
JP2018084626A (en) * | 2016-11-22 | 2018-05-31 | 日立化成デュポンマイクロシステムズ株式会社 | Photosensitive resin composition, method for producing patterned cured film, cured film, interlayer insulation film, cover coat layer, surface protective film and electronic component |
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