JP4174248B2 - ポリイミド樹脂、これを含有する樹脂組成物、電子部品用被覆材料及び電子部品用接着剤 - Google Patents
ポリイミド樹脂、これを含有する樹脂組成物、電子部品用被覆材料及び電子部品用接着剤 Download PDFInfo
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- JP4174248B2 JP4174248B2 JP2002192279A JP2002192279A JP4174248B2 JP 4174248 B2 JP4174248 B2 JP 4174248B2 JP 2002192279 A JP2002192279 A JP 2002192279A JP 2002192279 A JP2002192279 A JP 2002192279A JP 4174248 B2 JP4174248 B2 JP 4174248B2
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- 239000009719 polyimide resin Substances 0.000 title claims description 60
- 239000011342 resin composition Substances 0.000 title claims description 38
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- 230000001070 adhesive effect Effects 0.000 title claims description 28
- 239000011248 coating agent Substances 0.000 title claims description 18
- 238000000576 coating method Methods 0.000 title claims description 18
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- -1 phenolic aromatic diamine Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 9
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- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
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- 230000015572 biosynthetic process Effects 0.000 description 21
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- 238000002329 infrared spectrum Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- 238000009835 boiling Methods 0.000 description 7
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 4
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- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 4
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 3
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- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- WMTKEXLFSLRHQJ-UHFFFAOYSA-N 2-[(4-amino-3,5-dimethylphenyl)methyl]-6-[[3-[(4-amino-3,5-dimethylphenyl)methyl]-2-hydroxy-5-methylphenyl]methyl]-4-methylphenol Chemical compound OC=1C(CC=2C(=C(CC=3C=C(C)C(N)=C(C)C=3)C=C(C)C=2)O)=CC(C)=CC=1CC1=CC(C)=C(N)C(C)=C1 WMTKEXLFSLRHQJ-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000004427 diamine group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
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- 239000002243 precursor Substances 0.000 description 2
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- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
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- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical class NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 description 1
- QHDSBTKCTUXBEG-UHFFFAOYSA-N 2-[2-(2-aminophenoxy)phenoxy]aniline Chemical class NC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1N QHDSBTKCTUXBEG-UHFFFAOYSA-N 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 1
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- ULPWATNJVBJKGM-UHFFFAOYSA-N 3-[2-(3-amino-2-phenoxyphenyl)propan-2-yl]-2-phenoxyaniline Chemical class C=1C=CC(N)=C(OC=2C=CC=CC=2)C=1C(C)(C)C1=CC=CC(N)=C1OC1=CC=CC=C1 ULPWATNJVBJKGM-UHFFFAOYSA-N 0.000 description 1
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- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 1
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- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- PXNKTSGCFZNXGX-UHFFFAOYSA-N 5-methyl-2-oxaspiro[3.5]nonane-1,3-dione Chemical compound CC1CCCCC11C(=O)OC1=O PXNKTSGCFZNXGX-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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Images
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
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| JP2002192279A JP4174248B2 (ja) | 2002-07-01 | 2002-07-01 | ポリイミド樹脂、これを含有する樹脂組成物、電子部品用被覆材料及び電子部品用接着剤 |
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| JP2002192279A JP4174248B2 (ja) | 2002-07-01 | 2002-07-01 | ポリイミド樹脂、これを含有する樹脂組成物、電子部品用被覆材料及び電子部品用接着剤 |
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| JP2004035650A JP2004035650A (ja) | 2004-02-05 |
| JP2004035650A5 JP2004035650A5 (enExample) | 2006-08-31 |
| JP4174248B2 true JP4174248B2 (ja) | 2008-10-29 |
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| JP4084597B2 (ja) * | 2002-05-07 | 2008-04-30 | 群栄化学工業株式会社 | アミノ基含有フェノール誘導体 |
| JP4120780B2 (ja) * | 2002-07-19 | 2008-07-16 | 信越化学工業株式会社 | フェノール性水酸基を有するポリイミド樹脂の製造方法 |
| JP4204435B2 (ja) * | 2002-10-10 | 2009-01-07 | 信越化学工業株式会社 | 熱硬化性基を含有する透明ポリイミドシリコーン樹脂 |
| JP4871500B2 (ja) * | 2004-11-02 | 2012-02-08 | 株式会社カネカ | 樹脂組成物の流動性を向上させる樹脂改質材 |
| WO2007046405A1 (ja) * | 2005-10-21 | 2007-04-26 | Nippon Kayaku Kabushiki Kaisha | 熱硬化性樹脂組成物並びにその用途 |
| JP4737447B2 (ja) * | 2007-06-01 | 2011-08-03 | 信越化学工業株式会社 | フェノール性水酸基を有するポリイミド樹脂及びポリイミド樹脂組成物 |
| US8410620B2 (en) | 2007-09-20 | 2013-04-02 | Nippon Kayaku Kabushiki Kaisha | Primer resin for semiconductor device and semiconductor device |
| JP5045924B2 (ja) * | 2007-11-19 | 2012-10-10 | 信越化学工業株式会社 | フェノール性水酸基を有するポリイミド樹脂の製造方法 |
| KR101720819B1 (ko) * | 2009-08-18 | 2017-03-28 | 우베 고산 가부시키가이샤 | 폴리이미드 실록산 용액 조성물의 제조 방법, 및 폴리이미드 실록산 용액 조성물 |
| JP5811172B2 (ja) * | 2011-03-16 | 2015-11-11 | 東レ株式会社 | エポキシ樹脂組成物およびその製造方法ならびにそれを用いた半導体装置 |
| JP5707216B2 (ja) | 2011-04-26 | 2015-04-22 | 藤森工業株式会社 | Ｆｐｃ用電磁波シールド材 |
| CN102321244B (zh) * | 2011-07-22 | 2013-05-01 | 中山大学 | 含刚性非平面共轭结构的可溶性功能聚酰亚胺及其制备方法和应用 |
| JP5726048B2 (ja) * | 2011-11-14 | 2015-05-27 | 藤森工業株式会社 | Ｆｐｃ用電磁波シールド材 |
| JP6960404B2 (ja) | 2016-07-29 | 2021-11-05 | 株式会社カネカ | ポリイミド樹脂、および樹脂組成物 |
| JP6532518B2 (ja) * | 2017-12-08 | 2019-06-19 | 信越化学工業株式会社 | 高効率太陽電池の製造方法 |
| JP7271461B2 (ja) * | 2020-02-19 | 2023-05-11 | 信越化学工業株式会社 | 有機膜形成用材料およびパターン形成方法 |
| JP7527823B2 (ja) * | 2020-03-30 | 2024-08-05 | リンテック株式会社 | フィルム状接着剤 |
| JP7446887B2 (ja) * | 2020-03-30 | 2024-03-11 | リンテック株式会社 | フィルム状接着剤 |
| CN118027405B (zh) * | 2023-03-07 | 2025-02-11 | 江汉大学 | 一种光引发产酸固化型聚酰亚胺及其制备方法和光引发产酸固化型光刻胶 |
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