TWI743196B - 正型感光性樹脂組成物、乾膜、硬化物、印刷配線板及半導體元件 - Google Patents
正型感光性樹脂組成物、乾膜、硬化物、印刷配線板及半導體元件 Download PDFInfo
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- TWI743196B TWI743196B TW106131345A TW106131345A TWI743196B TW I743196 B TWI743196 B TW I743196B TW 106131345 A TW106131345 A TW 106131345A TW 106131345 A TW106131345 A TW 106131345A TW I743196 B TWI743196 B TW I743196B
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- Prior art keywords
- resin composition
- photosensitive resin
- silane coupling
- positive photosensitive
- coupling agent
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 50
- 239000004065 semiconductor Substances 0.000 title claims abstract description 11
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 43
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 40
- 229920002577 polybenzoxazole Polymers 0.000 claims abstract description 34
- 239000002243 precursor Substances 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 18
- 239000011347 resin Substances 0.000 claims abstract description 18
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 16
- 125000005264 aryl amine group Chemical group 0.000 claims abstract description 9
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims description 27
- 239000011248 coating agent Substances 0.000 claims description 25
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 abstract description 15
- 239000010408 film Substances 0.000 description 85
- -1 naphthoquinonediazide compound Chemical class 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- 239000010410 layer Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- 239000002253 acid Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical class [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 6
- 125000000962 organic group Chemical group 0.000 description 6
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- 239000010703 silicon Substances 0.000 description 5
- CSLFOBYNSUXTRU-UHFFFAOYSA-N 1,4-dioxonaphthalene-2-diazonium Chemical compound C1=CC=C2C(=O)C=C([N+]#N)C(=O)C2=C1 CSLFOBYNSUXTRU-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
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- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical compound [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
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- 239000011261 inert gas Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
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- ZGDMDBHLKNQPSD-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)phenol Chemical group C1=C(O)C(N)=CC=C1C1=CC=C(N)C(O)=C1 ZGDMDBHLKNQPSD-UHFFFAOYSA-N 0.000 description 1
- ZDRNVPNSQJRIRN-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C(O)=C1 ZDRNVPNSQJRIRN-UHFFFAOYSA-N 0.000 description 1
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- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 1
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- BJLUCDZIWWSFIB-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(O)=O)=C1 BJLUCDZIWWSFIB-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
Images
Classifications
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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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016-182791 | 2016-09-20 | ||
| JP2016182791 | 2016-09-20 |
Publications (2)
| Publication Number | Publication Date |
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| TW201827488A TW201827488A (zh) | 2018-08-01 |
| TWI743196B true TWI743196B (zh) | 2021-10-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| TW106131345A TWI743196B (zh) | 2016-09-20 | 2017-09-13 | 正型感光性樹脂組成物、乾膜、硬化物、印刷配線板及半導體元件 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP7011591B2 (ja) |
| KR (1) | KR102385641B1 (ja) |
| CN (1) | CN109716235B (ja) |
| TW (1) | TWI743196B (ja) |
| WO (1) | WO2018056013A1 (ja) |
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| JP2018097210A (ja) * | 2016-12-14 | 2018-06-21 | 日立化成デュポンマイクロシステムズ株式会社 | ポジ型感光性樹脂組成物、硬化パターンの製造方法、硬化物、層間絶縁膜、カバーコート層、表面保護膜及び電子部品 |
| JP7440224B2 (ja) * | 2019-08-21 | 2024-02-28 | 太陽ホールディングス株式会社 | ポジ型感光性樹脂組成物 |
Citations (2)
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|---|---|---|---|---|
| TW201533524A (zh) * | 2014-02-28 | 2015-09-01 | Jsr Corp | 絕緣膜的形成方法及使用絕緣膜的裝置 |
| TW201600564A (zh) * | 2014-06-27 | 2016-01-01 | Fujifilm Corp | 熱硬化性樹脂組成物、硬化膜、硬化膜的製造方法及半導體元件 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW594287B (en) * | 2002-12-17 | 2004-06-21 | Ind Tech Res Inst | Transflective display with different pre-tilt angle structures and its manufacturing method |
| JP2008538011A (ja) * | 2005-03-25 | 2008-10-02 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッド | 前処理組成物 |
| WO2007122929A1 (ja) * | 2006-03-30 | 2007-11-01 | Jsr Corporation | 感放射線性絶縁樹脂組成物 |
| JP5498170B2 (ja) * | 2007-12-26 | 2014-05-21 | 旭化成イーマテリアルズ株式会社 | 耐熱性樹脂前駆体及びそれを用いた感光性樹脂組成物 |
| KR100914064B1 (ko) * | 2008-03-19 | 2009-08-28 | 제일모직주식회사 | 포지티브형 감광성 수지 조성물 |
| JP5169446B2 (ja) | 2008-04-28 | 2013-03-27 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性樹脂組成物、該樹脂組成物を用いたポリベンゾオキサゾール膜、パターン硬化膜の製造方法及び電子部品 |
| WO2009136647A1 (ja) * | 2008-05-07 | 2009-11-12 | 住友ベークライト株式会社 | ポジ型感光性樹脂組成物、硬化膜、保護膜及び絶縁膜、並びにそれを用いた半導体装置及び表示体装置 |
| KR101249568B1 (ko) * | 2008-07-03 | 2013-04-01 | 아사히 가세이 이-매터리얼즈 가부시키가이샤 | 내열성 수지 전구체 및 그것을 사용한 감광성 수지 조성물 |
| CN102365341B (zh) * | 2009-03-31 | 2014-12-31 | 大日本印刷株式会社 | 碱产生剂、感光性树脂组合物、含有该感光性树脂组合物的图案形成用材料、使用该感光性树脂组合物的图案形成方法以及物品 |
| JP2011053458A (ja) | 2009-09-02 | 2011-03-17 | Hitachi Chemical Dupont Microsystems Ltd | 感光性樹脂組成物、該樹脂組成物を用いたパターン硬化膜の製造方法及び電子部品 |
| WO2011135887A1 (ja) * | 2010-04-28 | 2011-11-03 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物 |
| TWI430024B (zh) * | 2010-08-05 | 2014-03-11 | 旭化成電子材料股份有限公司 | A photosensitive resin composition, a method for manufacturing a hardened bump pattern, and a semiconductor device |
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2017
- 2017-08-30 JP JP2018540942A patent/JP7011591B2/ja active Active
- 2017-08-30 WO PCT/JP2017/031248 patent/WO2018056013A1/ja not_active Ceased
- 2017-08-30 KR KR1020197011002A patent/KR102385641B1/ko active Active
- 2017-08-30 CN CN201780057125.XA patent/CN109716235B/zh active Active
- 2017-09-13 TW TW106131345A patent/TWI743196B/zh active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201533524A (zh) * | 2014-02-28 | 2015-09-01 | Jsr Corp | 絕緣膜的形成方法及使用絕緣膜的裝置 |
| TW201600564A (zh) * | 2014-06-27 | 2016-01-01 | Fujifilm Corp | 熱硬化性樹脂組成物、硬化膜、硬化膜的製造方法及半導體元件 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2018056013A1 (ja) | 2019-07-04 |
| TW201827488A (zh) | 2018-08-01 |
| WO2018056013A1 (ja) | 2018-03-29 |
| CN109716235B (zh) | 2022-11-18 |
| JP7011591B2 (ja) | 2022-01-26 |
| KR102385641B1 (ko) | 2022-04-12 |
| KR20190054128A (ko) | 2019-05-21 |
| CN109716235A (zh) | 2019-05-03 |
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