DE102016210870A1 - Polyimidvorstufenzusammensetzung und ihre Verwendung und daraus hergestelltes Polyimid - Google Patents
Polyimidvorstufenzusammensetzung und ihre Verwendung und daraus hergestelltes Polyimid Download PDFInfo
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- DE102016210870A1 DE102016210870A1 DE102016210870.0A DE102016210870A DE102016210870A1 DE 102016210870 A1 DE102016210870 A1 DE 102016210870A1 DE 102016210870 A DE102016210870 A DE 102016210870A DE 102016210870 A1 DE102016210870 A1 DE 102016210870A1
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- precursor composition
- polyimide precursor
- polyimide
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- metal
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 313
- 239000004642 Polyimide Substances 0.000 title claims abstract description 305
- 239000000203 mixture Substances 0.000 title claims abstract description 146
- 239000002243 precursor Substances 0.000 title claims abstract description 145
- 239000002253 acid Substances 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 28
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000962 organic group Chemical group 0.000 claims description 24
- 238000007363 ring formation reaction Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002318 adhesion promoter Substances 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 6
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
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- 125000000129 anionic group Chemical group 0.000 claims description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 3
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 claims description 3
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000007731 hot pressing Methods 0.000 abstract description 7
- 239000010410 layer Substances 0.000 description 239
- 238000003475 lamination Methods 0.000 description 126
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- 229910052751 metal Inorganic materials 0.000 description 81
- 239000002184 metal Substances 0.000 description 81
- 239000011888 foil Substances 0.000 description 66
- 238000004519 manufacturing process Methods 0.000 description 59
- -1 methylpropenyl Chemical group 0.000 description 56
- 238000003756 stirring Methods 0.000 description 55
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 48
- 238000001816 cooling Methods 0.000 description 42
- 239000011889 copper foil Substances 0.000 description 34
- 239000000178 monomer Substances 0.000 description 32
- 229920006259 thermoplastic polyimide Polymers 0.000 description 26
- 239000007787 solid Substances 0.000 description 23
- 230000008569 process Effects 0.000 description 21
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 19
- 150000004985 diamines Chemical class 0.000 description 19
- 238000004090 dissolution Methods 0.000 description 18
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- 230000000052 comparative effect Effects 0.000 description 14
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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 11
- 239000011347 resin Substances 0.000 description 11
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- 238000012360 testing method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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- 0 *C(*)NC(*(C(*)=O)(C(NPC(*)(*)NC(*(C(O)=O)(C(O)=O)C(O*)=O)=O)=O)C(O)=O)=O Chemical compound *C(*)NC(*(C(*)=O)(C(NPC(*)(*)NC(*(C(O)=O)(C(O)=O)C(O*)=O)=O)=O)C(O)=O)=O 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
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- 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
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/022—Processes for manufacturing precursors of printed circuits, i.e. copper-clad substrates
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Laminated Bodies (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW104119714A TWI564145B (zh) | 2015-06-17 | 2015-06-17 | 金屬被覆積層板及其製造方法 |
| TW104119714 | 2015-06-17 | ||
| TW104140909 | 2015-12-04 | ||
| TW104140909A TWI568774B (zh) | 2015-12-04 | 2015-12-04 | 聚醯亞胺前驅物組合物、其用途及由其製備之聚醯亞胺 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102016210870A1 true DE102016210870A1 (de) | 2016-12-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102016210870.0A Ceased DE102016210870A1 (de) | 2015-06-17 | 2016-06-17 | Polyimidvorstufenzusammensetzung und ihre Verwendung und daraus hergestelltes Polyimid |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20160369056A1 (https=) |
| JP (1) | JP6317399B2 (https=) |
| KR (1) | KR101844925B1 (https=) |
| CN (1) | CN106256846B (https=) |
| DE (1) | DE102016210870A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI650346B (zh) * | 2016-11-30 | 2019-02-11 | 長興材料工業股份有限公司 | 聚醯亞胺前驅物組合物及其應用 |
| TWI621642B (zh) * | 2016-11-30 | 2018-04-21 | 長興材料工業股份有限公司 | 聚醯亞胺前驅物及其應用 |
| TWI627203B (zh) | 2017-03-31 | 2018-06-21 | 長興材料工業股份有限公司 | 聚醯亞胺前驅物組合物、其用途及由其製備之聚醯亞胺 |
| TWI617441B (zh) * | 2017-03-31 | 2018-03-11 | 長興材料工業股份有限公司 | 於基板上製備圖案化覆蓋膜之方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200709751A (en) | 2005-08-31 | 2007-03-01 | Thinflex Corp | Polyimide copper foil laminate and method of producing the same |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62227978A (ja) * | 1986-03-28 | 1987-10-06 | Hitachi Chem Co Ltd | 樹脂ペ−スト |
| KR930004777B1 (ko) * | 1987-01-31 | 1993-06-08 | 가부시키가이샤 도시바 | 내열성 절연피복재 및 이것을 이용한 써말 헤드 |
| DE69128187T2 (de) * | 1990-09-28 | 1998-03-26 | Toshiba Kawasaki Kk | Fotoempfindliche Harzzusammensetzung zum Herstellen eines Polyimidfilmmusters und Verfahren zum Herstellen eines Polyimidfilmmusters |
| US5310862A (en) * | 1991-08-20 | 1994-05-10 | Toray Industries, Inc. | Photosensitive polyimide precursor compositions and process for preparing same |
| JPH073018A (ja) * | 1993-06-14 | 1995-01-06 | Toshiba Chem Corp | ポリイミド樹脂 |
| JP3518080B2 (ja) * | 1995-08-17 | 2004-04-12 | 東レ株式会社 | ポリイミド前駆体組成物の製造方法 |
| JPH0990632A (ja) * | 1995-09-28 | 1997-04-04 | Sumitomo Bakelite Co Ltd | 感光性樹脂組成物及びそのパターン形成方法 |
| JPH09302225A (ja) * | 1996-03-14 | 1997-11-25 | Toshiba Corp | ポリイミド前駆体組成物、ポリイミド膜の形成方法、電子部品および液晶素子 |
| JP2002182378A (ja) * | 2000-12-18 | 2002-06-26 | Hitachi Chemical Dupont Microsystems Ltd | アルカリネガ現像型感光性樹脂組成物、パターンの製造法及び電子部品 |
| TW200300772A (en) * | 2001-12-11 | 2003-06-16 | Kaneka Corp | Polyimide precursor, manufacturing method thereof, and resin composition using polyimide precursor |
| JP2003248309A (ja) * | 2001-12-19 | 2003-09-05 | Hitachi Chemical Dupont Microsystems Ltd | 感光性樹脂組成物、これを用いたパターン製造法及び電子部品 |
| US7026436B2 (en) * | 2002-11-26 | 2006-04-11 | E.I. Du Pont De Nemours And Company | Low temperature polyimide adhesive compositions and methods relating thereto |
| JP4870173B2 (ja) * | 2003-04-07 | 2012-02-08 | 三井化学株式会社 | ポリイミド金属積層板 |
| KR100839760B1 (ko) * | 2006-02-06 | 2008-06-19 | 주식회사 엘지화학 | 칩 온 필름용 동장 적층판 |
| TWI311142B (en) * | 2006-10-18 | 2009-06-21 | Eternal Chemical Co Ltd | Amic acid ester oligomer, precursor composition for polyimide resin containing the same, and uses |
| TWI435893B (zh) * | 2007-08-03 | 2014-05-01 | Eternal Chemical Co Ltd | 聚醯亞胺之前驅物及其應用 |
| JP2009091413A (ja) * | 2007-10-05 | 2009-04-30 | Ist Corp | ポリイミド前駆体組成物、感光性ポリイミド前駆体組成物及びこれを用いた電子部品並びに被膜形成方法 |
| JP2010151946A (ja) * | 2008-12-24 | 2010-07-08 | Hitachi Chem Co Ltd | 感光性樹脂組成物及び感光性エレメント |
| JP2012255107A (ja) * | 2011-06-09 | 2012-12-27 | Mitsui Chemicals Inc | 熱可塑性ポリイミド組成物、それを含む接着剤、積層体、及びデバイス |
| TWI486335B (zh) * | 2011-12-29 | 2015-06-01 | Eternal Materials Co Ltd | 鹼產生劑 |
| JP2015078254A (ja) * | 2013-10-15 | 2015-04-23 | 東レ株式会社 | 樹脂組成物、それを用いたポリイミド樹脂膜、それを含むカラーフィルタ、ｔｆｔ基板、表示デバイスおよびそれらの製造方法 |
-
2016
- 2016-02-26 CN CN201610107149.9A patent/CN106256846B/zh active Active
- 2016-06-17 JP JP2016121232A patent/JP6317399B2/ja active Active
- 2016-06-17 DE DE102016210870.0A patent/DE102016210870A1/de not_active Ceased
- 2016-06-17 KR KR1020160076097A patent/KR101844925B1/ko active Active
- 2016-06-17 US US15/185,928 patent/US20160369056A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200709751A (en) | 2005-08-31 | 2007-03-01 | Thinflex Corp | Polyimide copper foil laminate and method of producing the same |
Non-Patent Citations (1)
| Title |
|---|
| UL94-Standard |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017061671A (ja) | 2017-03-30 |
| CN106256846B (zh) | 2019-04-16 |
| KR101844925B1 (ko) | 2018-04-04 |
| CN106256846A (zh) | 2016-12-28 |
| US20160369056A1 (en) | 2016-12-22 |
| KR20160149171A (ko) | 2016-12-27 |
| JP6317399B2 (ja) | 2018-04-25 |
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