JP2011514266A5 - - Google Patents
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- Publication number
- JP2011514266A5 JP2011514266A5 JP2010545937A JP2010545937A JP2011514266A5 JP 2011514266 A5 JP2011514266 A5 JP 2011514266A5 JP 2010545937 A JP2010545937 A JP 2010545937A JP 2010545937 A JP2010545937 A JP 2010545937A JP 2011514266 A5 JP2011514266 A5 JP 2011514266A5
- Authority
- JP
- Japan
- Prior art keywords
- polyimide
- polyimide precursor
- clad laminate
- coupling agent
- silane coupling
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004642 Polyimide Substances 0.000 claims description 44
- 229920001721 polyimide Polymers 0.000 claims description 44
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 23
- 239000002243 precursor Substances 0.000 claims description 18
- 229910052802 copper Inorganic materials 0.000 claims description 17
- 239000010949 copper Substances 0.000 claims description 17
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 10
- -1 glycidoxy Chemical group 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 6
- 239000011889 copper foil Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000003475 lamination Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical group NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- XROLBZOMVNMIFN-UHFFFAOYSA-N 1-(1-benzofuran-4-yl)propan-2-amine Chemical compound CC(N)CC1=CC=CC2=C1C=CO2 XROLBZOMVNMIFN-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- DDOQBQRIEWHWBT-UHFFFAOYSA-N 2-azaniumyl-4-phosphonobutanoate Chemical compound OC(=O)C(N)CCP(O)(O)=O DDOQBQRIEWHWBT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
- LVACOMKKELLCHJ-UHFFFAOYSA-N 3-trimethoxysilylpropylurea Chemical group CO[Si](OC)(OC)CCCNC(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 description 1
- KHYXYOGWAIYVBD-UHFFFAOYSA-N 4-(4-propylphenoxy)aniline Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N)C=C1 KHYXYOGWAIYVBD-UHFFFAOYSA-N 0.000 description 1
- RYYUUQPLFHRZOY-UHFFFAOYSA-N 4-[2-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1OC1=CC=C(N)C=C1 RYYUUQPLFHRZOY-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- YGQZOUHXUGYNPH-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)-3-methylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(C)=CC=1OC1=CC=C(N)C=C1 YGQZOUHXUGYNPH-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 1
- BBTGUNMUUYNPLH-UHFFFAOYSA-N 5-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 BBTGUNMUUYNPLH-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW97104940A TWI398350B (zh) | 2008-02-05 | 2008-02-05 | 高黏著性聚醯亞胺銅箔積層板及其製造方法 |
| US12/117,026 US20090197104A1 (en) | 2008-02-05 | 2008-05-08 | Highly adhesive polyimide copper clad laminate and method of making the same |
| PCT/US2009/032550 WO2009099918A1 (en) | 2008-02-05 | 2009-01-30 | Highly adhesive polyimide copper clad laminate and method of making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011514266A JP2011514266A (ja) | 2011-05-06 |
| JP2011514266A5 true JP2011514266A5 (enExample) | 2012-01-26 |
Family
ID=40931988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010545937A Pending JP2011514266A (ja) | 2008-02-05 | 2009-01-30 | 高接着性ポリイミド銅張積層板およびその製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20090197104A1 (enExample) |
| JP (1) | JP2011514266A (enExample) |
| CN (1) | CN101932629B (enExample) |
| TW (1) | TWI398350B (enExample) |
| WO (1) | WO2009099918A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011063204A1 (en) * | 2009-11-20 | 2011-05-26 | E. I. Du Pont De Nemours And Company | Thermally and dimensionally stable polyimide films and methods relating thereto |
| JP5347980B2 (ja) * | 2010-01-14 | 2013-11-20 | 住友金属鉱山株式会社 | 金属化ポリイミドフィルム、及びそれを用いたフレキシブル配線板 |
| CN102855975B (zh) * | 2011-06-30 | 2017-06-06 | 日立金属株式会社 | 绝缘电线及使用该绝缘电线的线圈 |
| CN103050616B (zh) * | 2011-10-13 | 2015-10-28 | 昆山雅森电子材料科技有限公司 | 复合式导热铜箔基板 |
| CN102532543B (zh) * | 2011-12-20 | 2014-01-29 | 中国科学院化学研究所 | 共聚型可热封接聚酰亚胺及其制备方法与应用 |
| JP2013131424A (ja) * | 2011-12-22 | 2013-07-04 | Hitachi Cable Ltd | 絶縁電線及びそれを用いたコイル |
| JP6172139B2 (ja) * | 2012-02-23 | 2017-08-02 | 日立化成デュポンマイクロシステムズ株式会社 | 樹脂組成物、及びこれを用いたポリイミド樹脂膜、ディスプレイ基板とその製造方法 |
| JP5362921B1 (ja) * | 2012-11-09 | 2013-12-11 | Ｊｘ日鉱日石金属株式会社 | 表面処理銅箔及びそれを用いた積層板 |
| KR101441344B1 (ko) * | 2013-01-15 | 2014-09-18 | 애경유화주식회사 | 고투과 고선택성 공중합체 폴리이미드 소재 및 그의 합성 방법 |
| CN104968709B (zh) * | 2013-02-07 | 2017-08-11 | 株式会社钟化 | 烷氧基硅烷改性聚酰胺酸溶液、使用其的层叠体及柔性器件、以及层叠体的制造方法 |
| CN103680700B (zh) * | 2013-12-18 | 2019-05-24 | 南昌大学 | 含聚酰亚胺改性的硅烷偶联剂涂层的漆包线 |
| CN106574051A (zh) * | 2014-08-12 | 2017-04-19 | 株式会社钟化 | 烷氧基硅烷改性聚酰胺酸溶液、使用了其的层叠体及柔性器件、以及层叠体的制造方法 |
| CN105238338A (zh) * | 2015-11-12 | 2016-01-13 | 烟台德邦科技有限公司 | 一种晶圆减薄高温临时粘结剂及其制备方法 |
| CN106085338B (zh) * | 2016-06-20 | 2019-07-12 | 新黎明科技股份有限公司 | 一种玻璃灯罩修补液 |
| WO2018032051A1 (en) * | 2016-08-16 | 2018-02-22 | Commonwealth Scientific And Industrial Research Organisation | Chemistry for fines fixing and water control |
| CN107134542A (zh) * | 2017-04-10 | 2017-09-05 | 珠海亚泰电子科技有限公司 | 透明单面覆铜板制作工艺 |
| KR101959807B1 (ko) * | 2018-08-22 | 2019-03-20 | 에스케이씨코오롱피아이 주식회사 | 방향족 카르복실산을 포함하는 도체 피복용 폴리이미드 바니쉬 및 이의 제조방법 |
| CN109852330B (zh) * | 2018-12-21 | 2022-01-11 | 东华大学 | 一种3,5-二氨基苯甲酸型含硅胶粘剂及其制备方法 |
| CN110572933A (zh) * | 2019-08-23 | 2019-12-13 | 李龙凯 | 一种高频线路板新型材料层结构的制备方法及其制品 |
| CN110868799A (zh) * | 2019-11-15 | 2020-03-06 | 江苏上达电子有限公司 | 一种透明cof设计方法 |
| CN111040156B (zh) * | 2019-11-28 | 2022-05-31 | 李南文 | 一种耐溶剂且高尺寸稳定性的交联型聚酰亚胺薄膜 |
| US12031013B2 (en) | 2021-07-19 | 2024-07-09 | Momentive Performance Materials Inc. | Silane coupling agents to improve resin adhesion |
| KR102564595B1 (ko) * | 2021-07-20 | 2023-08-09 | 피아이첨단소재 주식회사 | 폴리아믹산 조성물 및 이를 포함하는 폴리이미드 피복물 |
| CN113619224B (zh) * | 2021-07-23 | 2024-02-02 | 中山新高电子材料股份有限公司 | 一种低吸水率氟材柔性覆铜板及其制备方法 |
| CN116332526A (zh) * | 2023-01-16 | 2023-06-27 | 江西沃格光电股份有限公司 | 柔性盖板及其制备方法与应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6368641A (ja) * | 1986-09-09 | 1988-03-28 | Hitachi Chem Co Ltd | ポリイミド成形品の表面処理方法 |
| KR930004777B1 (ko) * | 1987-01-31 | 1993-06-08 | 가부시키가이샤 도시바 | 내열성 절연피복재 및 이것을 이용한 써말 헤드 |
| EP0304022A3 (en) * | 1987-08-21 | 1990-12-19 | E.I. Du Pont De Nemours And Company | Polyimide coating composition |
| JP2776056B2 (ja) * | 1991-06-04 | 1998-07-16 | 日立化成工業株式会社 | ポリアミノビスマレイミド樹脂組成物及びそれを用いた銅張積層板の製造方法 |
| JPH0794834A (ja) * | 1993-09-20 | 1995-04-07 | Toshiba Chem Corp | フレキシブル印刷回路基板 |
| JP3534151B2 (ja) * | 1996-10-29 | 2004-06-07 | 宇部興産株式会社 | ポリイミド前駆体組成物及びポリイミド膜 |
| TWI272183B (en) * | 2001-11-01 | 2007-02-01 | Arakawa Chem Ind | Polyimide-metal layered products and polyamideimide-metal layered product |
| CN1301046C (zh) * | 2002-05-13 | 2007-02-14 | 三井金属鉱业株式会社 | 膜上芯片用软性印刷线路板 |
| TWI298988B (en) * | 2002-07-19 | 2008-07-11 | Ube Industries | Copper-clad laminate |
| JP3977790B2 (ja) * | 2003-09-01 | 2007-09-19 | 古河サーキットフォイル株式会社 | キャリア付き極薄銅箔の製造方法、及び該製造方法で製造された極薄銅箔、該極薄銅箔を使用したプリント配線板、多層プリント配線板、チップオンフィルム用配線基板 |
| JP4174677B2 (ja) * | 2004-06-28 | 2008-11-05 | 信越化学工業株式会社 | フレキシブル金属箔ポリイミド積層板及びその製造方法 |
| JP4957059B2 (ja) * | 2005-04-19 | 2012-06-20 | 宇部興産株式会社 | ポリイミドフィルム積層体 |
| CN101017285A (zh) * | 2006-02-07 | 2007-08-15 | Jsr株式会社 | 垂直取向型液晶取向剂和垂直取向型液晶显示元件 |
| TWI306882B (en) * | 2006-05-25 | 2009-03-01 | Ind Tech Res Inst | Thermoplastic polyimide composition and method of making double-sided flexible copper clad laminate using the same |
-
2008
- 2008-02-05 TW TW97104940A patent/TWI398350B/zh not_active IP Right Cessation
- 2008-05-08 US US12/117,026 patent/US20090197104A1/en not_active Abandoned
-
2009
- 2009-01-30 JP JP2010545937A patent/JP2011514266A/ja active Pending
- 2009-01-30 CN CN2009801039862A patent/CN101932629B/zh not_active Expired - Fee Related
- 2009-01-30 WO PCT/US2009/032550 patent/WO2009099918A1/en not_active Ceased
- 2009-01-30 US US12/865,746 patent/US20100323161A1/en not_active Abandoned
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