JP6254197B2 - ポリイミド前駆体及びそれを含有する樹脂組成物 - Google Patents
ポリイミド前駆体及びそれを含有する樹脂組成物 Download PDFInfo
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- JP6254197B2 JP6254197B2 JP2015562686A JP2015562686A JP6254197B2 JP 6254197 B2 JP6254197 B2 JP 6254197B2 JP 2015562686 A JP2015562686 A JP 2015562686A JP 2015562686 A JP2015562686 A JP 2015562686A JP 6254197 B2 JP6254197 B2 JP 6254197B2
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- Japan
- Prior art keywords
- dianhydride
- tetracarboxylic dianhydride
- pmda
- mmol
- tetracarboxylic
- 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.)
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- 239000004642 Polyimide Substances 0.000 title claims description 107
- 239000002243 precursor Substances 0.000 title claims description 88
- 239000011342 resin composition Substances 0.000 title claims description 57
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 claims description 211
- 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 202
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 145
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 105
- 239000002904 solvent Substances 0.000 claims description 78
- 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 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 63
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- 125000002723 alicyclic group Chemical group 0.000 claims description 49
- 150000004985 diamines Chemical class 0.000 claims description 45
- 239000011248 coating agent Substances 0.000 claims description 30
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- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 claims description 26
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- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 claims description 23
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 claims description 21
- QEZSZSGCZNXZKI-UHFFFAOYSA-N C1(C(CC(C(C1)C(=O)O)C(=O)O)C(=O)O)(C1CCCCC1)C(=O)O Chemical compound C1(C(CC(C(C1)C(=O)O)C(=O)O)C(=O)O)(C1CCCCC1)C(=O)O QEZSZSGCZNXZKI-UHFFFAOYSA-N 0.000 claims description 20
- CJYIPJMCGHGFNN-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic acid Chemical compound C1C2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O CJYIPJMCGHGFNN-UHFFFAOYSA-N 0.000 claims description 20
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 claims description 20
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 20
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 claims description 19
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- 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 claims description 15
- LOCTYHIHNCOYJZ-UHFFFAOYSA-N (4-aminophenyl) 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1OC(=O)C1=CC=C(N)C=C1 LOCTYHIHNCOYJZ-UHFFFAOYSA-N 0.000 claims description 13
- JYCTWJFSRDBYJX-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3a,4,5,9b-tetrahydrobenzo[e][2]benzofuran-1,3-dione Chemical compound O=C1OC(=O)CC1C1C2=CC=CC=C2C(C(=O)OC2=O)C2C1 JYCTWJFSRDBYJX-UHFFFAOYSA-N 0.000 claims description 13
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- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 claims description 11
- 150000008064 anhydrides Chemical class 0.000 claims description 11
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- 239000004094 surface-active agent Substances 0.000 claims description 11
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- RHRNYXVSZLSRRP-UHFFFAOYSA-N 3-(carboxymethyl)cyclopentane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CC1C(C(O)=O)CC(C(O)=O)C1C(O)=O RHRNYXVSZLSRRP-UHFFFAOYSA-N 0.000 claims description 6
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- UEYGDIASMOPQFG-UHFFFAOYSA-N octane-1,3,5,7-tetracarboxylic acid Chemical compound OC(=O)C(C)CC(C(O)=O)CC(C(O)=O)CCC(O)=O UEYGDIASMOPQFG-UHFFFAOYSA-N 0.000 claims description 6
- 238000005229 chemical vapour deposition Methods 0.000 claims description 4
- JDGFELYPUWNNGR-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene-1,3,4,6-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C2C(C(=O)O)CC(C(O)=O)C21 JDGFELYPUWNNGR-UHFFFAOYSA-N 0.000 claims description 3
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- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 2
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- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate Chemical compound OC1=C(C([O-])=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-M 0.000 claims 15
- ABMKWMASVFVTMD-UHFFFAOYSA-N 1-methyl-2-(2-methylphenyl)benzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1C ABMKWMASVFVTMD-UHFFFAOYSA-N 0.000 claims 4
- 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 claims 2
- 150000003949 imides Chemical class 0.000 claims 1
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- 230000000996 additive effect Effects 0.000 description 1
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- 239000003513 alkali Substances 0.000 description 1
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- XPNHTKZQLZVYHZ-UHFFFAOYSA-N hydroxy-diphenyl-propan-2-ylsilane Chemical compound C=1C=CC=CC=1[Si](O)(C(C)C)C1=CC=CC=C1 XPNHTKZQLZVYHZ-UHFFFAOYSA-N 0.000 description 1
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- FQQOMIXCGMRXEH-UHFFFAOYSA-N hydroxy-methyl-phenyl-propylsilane Chemical compound CCC[Si](C)(O)C1=CC=CC=C1 FQQOMIXCGMRXEH-UHFFFAOYSA-N 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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- HAQMPJFWQWLQDO-UHFFFAOYSA-N tert-butyl-ethyl-hydroxy-phenylsilane Chemical compound CC[Si](O)(C(C)(C)C)C1=CC=CC=C1 HAQMPJFWQWLQDO-UHFFFAOYSA-N 0.000 description 1
- UNAYGNMKNYRIHL-UHFFFAOYSA-N tert-butyl-hydroxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](O)(C(C)(C)C)C1=CC=CC=C1 UNAYGNMKNYRIHL-UHFFFAOYSA-N 0.000 description 1
- VLKDZHUARIPFFA-UHFFFAOYSA-N tert-butyl-hydroxy-methyl-phenylsilane Chemical compound CC(C)(C)[Si](C)(O)C1=CC=CC=C1 VLKDZHUARIPFFA-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- YFNYCSJNUJQGNF-UHFFFAOYSA-N triethoxy(1-triethoxysilylethenyl)silane Chemical group CCO[Si](OCC)(OCC)C(=C)[Si](OCC)(OCC)OCC YFNYCSJNUJQGNF-UHFFFAOYSA-N 0.000 description 1
- FOQJQXVUMYLJSU-UHFFFAOYSA-N triethoxy(1-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)[Si](OCC)(OCC)OCC FOQJQXVUMYLJSU-UHFFFAOYSA-N 0.000 description 1
- VJDYPOQWHRJALO-UHFFFAOYSA-N triethoxy(1-triethoxysilylocta-1,3-dienyl)silane Chemical compound CCCCC=CC=C([Si](OCC)(OCC)OCC)[Si](OCC)(OCC)OCC VJDYPOQWHRJALO-UHFFFAOYSA-N 0.000 description 1
- KMLVDTJUQJXRRH-UHFFFAOYSA-N triethoxy(2-pyridin-2-ylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=N1 KMLVDTJUQJXRRH-UHFFFAOYSA-N 0.000 description 1
- OSAJVUUALHWJEM-UHFFFAOYSA-N triethoxy(8-triethoxysilyloctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCCC[Si](OCC)(OCC)OCC OSAJVUUALHWJEM-UHFFFAOYSA-N 0.000 description 1
- NIINUVYELHEORX-UHFFFAOYSA-N triethoxy(triethoxysilylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)C[Si](OCC)(OCC)OCC NIINUVYELHEORX-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- JBYXACURRYATNJ-UHFFFAOYSA-N trimethoxy(1-trimethoxysilylhexyl)silane Chemical compound CCCCCC([Si](OC)(OC)OC)[Si](OC)(OC)OC JBYXACURRYATNJ-UHFFFAOYSA-N 0.000 description 1
- XVZMLSWFBPLMEA-UHFFFAOYSA-N trimethoxy(2-pyridin-2-ylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=N1 XVZMLSWFBPLMEA-UHFFFAOYSA-N 0.000 description 1
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- XQEGZYAXBCFSBS-UHFFFAOYSA-N trimethoxy-(4-methylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=C(C)C=C1 XQEGZYAXBCFSBS-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
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Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6254197B2 (ja) * | 2014-02-14 | 2017-12-27 | 旭化成株式会社 | ポリイミド前駆体及びそれを含有する樹脂組成物 |
| WO2016060213A1 (ja) * | 2014-10-17 | 2016-04-21 | 三菱瓦斯化学株式会社 | ポリイミド樹脂組成物、ポリイミドフィルム及び積層体 |
| KR20210080594A (ko) * | 2015-03-13 | 2021-06-30 | 아사히 가세이 가부시키가이샤 | 폴리이미드 전구체 수지 조성물 |
| WO2016167296A1 (ja) * | 2015-04-17 | 2016-10-20 | 旭化成株式会社 | 樹脂組成物、ポリイミド樹脂膜、及びその製造方法 |
| CN112940253A (zh) * | 2015-09-24 | 2021-06-11 | 旭化成株式会社 | 聚酰亚胺前体、树脂组合物和树脂薄膜的制造方法 |
| EP3354676B1 (en) | 2015-09-25 | 2024-05-15 | Mitsubishi Gas Chemical Company, Inc. | Polyimide resin and polyimide film |
| JP6634801B2 (ja) * | 2015-12-03 | 2020-01-22 | Jsr株式会社 | 液晶配向剤 |
| KR102417428B1 (ko) * | 2015-12-21 | 2022-07-06 | 주식회사 두산 | 지환족 모노머가 적용된 폴리아믹산 조성물 및 이를 이용한 투명 폴리이미드 필름 |
| KR102460588B1 (ko) * | 2016-03-09 | 2022-10-28 | 주식회사 두산 | 금속 적층체 및 이를 포함하는 인쇄회로기판 |
| EP3453733B1 (en) * | 2016-05-02 | 2023-01-18 | Mitsubishi Gas Chemical Company, Inc. | Polyimide resin, polyimide resin composition, and polyimide film |
| JP6954276B2 (ja) * | 2016-05-09 | 2021-10-27 | 三菱瓦斯化学株式会社 | ポリイミド樹脂及びポリイミド樹脂組成物 |
| JP6693676B2 (ja) * | 2016-05-09 | 2020-05-13 | 三菱瓦斯化学株式会社 | ポリイミド及びポリイミドフィルム |
| KR102339091B1 (ko) * | 2016-05-20 | 2021-12-15 | 에스케이이노베이션 주식회사 | 폴리아믹산 조성물, 이로부터 제조된 폴리아미드이미드 필름 및 이의 제조방법 |
| TWI723166B (zh) * | 2016-05-23 | 2021-04-01 | 日商日產化學工業股份有限公司 | 剝離層形成用組成物及剝離層 |
| JP6705583B2 (ja) * | 2016-08-08 | 2020-06-03 | Ｊｘｔｇエネルギー株式会社 | ポリイミド、ポリアミド酸、ポリアミド酸溶液、及び、ポリイミドフィルム |
| JP7079076B2 (ja) * | 2016-08-10 | 2022-06-01 | 日鉄ケミカル＆マテリアル株式会社 | ポリイミド前駆体及びそれから生じるポリイミド |
| JP6890999B2 (ja) * | 2016-08-10 | 2021-06-18 | 日鉄ケミカル＆マテリアル株式会社 | ポリイミド前駆体及びポリイミド |
| KR101899902B1 (ko) * | 2016-08-23 | 2018-09-18 | 주식회사 대림코퍼레이션 | 수지안정성, 내열성이 향상되고 투명성을 갖는 폴리이미드 전구체 수지 조성물, 이를 이용한 폴리이미드 필름 제조방법, 및 이에 의해 제조된 폴리이미드 필름 |
| JP7186617B2 (ja) * | 2016-09-30 | 2022-12-09 | 住友化学株式会社 | ポリイミド系高分子ワニスの製造方法、ポリイミド系高分子フィルムの製造方法、及び、透明ポリイミド系高分子フィルム |
| JP7011231B2 (ja) * | 2016-11-24 | 2022-01-26 | 日産化学株式会社 | フレキシブルデバイス基板形成用組成物 |
| JP7011230B2 (ja) * | 2016-11-24 | 2022-01-26 | 日産化学株式会社 | フレキシブルデバイス基板形成用組成物 |
| JP6944784B2 (ja) * | 2017-02-03 | 2021-10-06 | 東京応化工業株式会社 | 積層体、フレキシブルデバイスおよび積層体の製造方法 |
| JP2020528086A (ja) * | 2017-05-10 | 2020-09-17 | デュポン エレクトロニクス インコーポレイテッド | 電子デバイスにおけるフレキシブル基板のためのロ−カラーポリマー |
| TW201920364A (zh) * | 2017-08-11 | 2019-06-01 | 美商杜邦股份有限公司 | 用於電子裝置中之可撓性基板之低色度聚合物 |
| US11970579B2 (en) | 2017-09-12 | 2024-04-30 | Sk Innovation Co., Ltd. | Polyamic acid resin and polyamideimide film |
| CN111212867A (zh) * | 2017-10-11 | 2020-05-29 | 株式会社钟化 | 聚酰亚胺树脂及其制造方法、聚酰亚胺溶液、以及聚酰亚胺薄膜及其制造方法 |
| WO2019116940A1 (ja) * | 2017-12-15 | 2019-06-20 | 三菱瓦斯化学株式会社 | ポリイミド樹脂、ポリイミドワニス及びポリイミドフィルム |
| US20200369830A1 (en) * | 2017-12-26 | 2020-11-26 | Kaneka Corporation | Polyamide acid composition and method for producing same, polyimide film, laminate and method for producing same, and flexible device |
| KR102271028B1 (ko) * | 2017-12-29 | 2021-06-29 | 코오롱인더스트리 주식회사 | 폴리아믹산의 제조방법, 이로부터 제조된 폴리아믹산, 폴리이미드 수지 및 폴리이미드 필름 |
| KR102015769B1 (ko) | 2018-01-12 | 2019-08-29 | 경희대학교 산학협력단 | 폴리아믹산 공중합체, 이를 이용하여 제조된 고내열성 투명 폴리이미드 필름 및 이의 제조방법 |
| CN111936554B (zh) * | 2018-04-10 | 2023-04-28 | 三菱瓦斯化学株式会社 | 聚酰亚胺树脂、聚酰亚胺清漆及聚酰亚胺薄膜 |
| JP2019215394A (ja) * | 2018-06-11 | 2019-12-19 | 株式会社ジャパンディスプレイ | 表示装置 |
| JP7120819B2 (ja) * | 2018-06-12 | 2022-08-17 | 旭化成株式会社 | ポリイミドフィルムとフレキシブルガラスとの積層体 |
| JP7158914B2 (ja) * | 2018-06-26 | 2022-10-24 | 株式会社ジャパンディスプレイ | 表示装置 |
| CN112334511B (zh) * | 2018-06-28 | 2023-06-20 | 株式会社钟化 | 聚酰亚胺树脂及其制造方法、以及聚酰亚胺薄膜及其制造方法 |
| WO2020016954A1 (ja) * | 2018-07-18 | 2020-01-23 | 住友電気工業株式会社 | 樹脂ワニス、絶縁電線及び絶縁電線の製造方法 |
| CN113166412B (zh) * | 2018-11-28 | 2024-03-08 | 三菱瓦斯化学株式会社 | 聚酰亚胺树脂、聚酰亚胺清漆及聚酰亚胺薄膜 |
| JP7298141B2 (ja) * | 2018-11-30 | 2023-06-27 | 株式会社リコー | 硬化型組成物、組成物収容容器、２次元又は３次元の像の形成方法及び形成装置、硬化物、構造体、並びに成形加工品 |
| CN109824894B (zh) * | 2019-01-29 | 2021-08-10 | 西北工业大学 | 一种分子主链由两种酸酐交替组成的聚酰亚胺薄膜制备方法 |
| CN110183851B (zh) * | 2019-04-13 | 2024-09-06 | 复旦大学 | 一种含氟脂环族共聚聚酰亚胺薄膜材料及其制备方法 |
| TWI764046B (zh) * | 2019-09-19 | 2022-05-11 | 臻鼎科技股份有限公司 | 聚醯胺酸嵌段共聚物及其製備方法、聚醯亞胺覆銅板及電路板 |
| CN112521603B (zh) | 2019-09-19 | 2023-06-02 | 臻鼎科技股份有限公司 | 聚酰胺酸嵌段共聚物及其制备方法、聚酰亚胺覆铜板及电路板 |
| CN111187414B (zh) * | 2020-02-14 | 2022-09-06 | 吉林奥来德光电材料股份有限公司 | 高性能透明聚酰亚胺薄膜及其制备方法 |
| CN111363354A (zh) * | 2020-03-27 | 2020-07-03 | 中天电子材料有限公司 | 聚酰亚胺无色透明薄膜及其制备方法、光学pi膜 |
| JP7107451B2 (ja) * | 2020-05-29 | 2022-07-27 | 東洋紡株式会社 | ポリイミドフィルムおよびその製造方法 |
| JP7103534B2 (ja) * | 2020-05-29 | 2022-07-20 | 東洋紡株式会社 | ポリイミドフィルムおよびその製造方法 |
| JPWO2021261177A1 (zh) * | 2020-06-23 | 2021-12-30 | ||
| KR20230030640A (ko) * | 2020-09-29 | 2023-03-06 | 도요보 가부시키가이샤 | 무기 기판과 폴리아믹산 경화물의 적층체 |
| CN112375241B (zh) * | 2020-11-03 | 2021-05-11 | 深圳瑞华泰薄膜科技股份有限公司 | 一种无色透明聚酰亚胺薄膜及其制备方法 |
| CN112480672B (zh) * | 2020-11-27 | 2022-11-04 | 桂林电器科学研究院有限公司 | 一种无色透明聚酰亚胺薄膜及其制备方法 |
| JP7174199B1 (ja) * | 2021-04-02 | 2022-11-17 | 旭化成株式会社 | ポリイミド、樹脂組成物、ポリイミドフィルム、及び、その製造方法 |
| CN117120514A (zh) * | 2021-04-16 | 2023-11-24 | 三菱瓦斯化学株式会社 | 酰亚胺-酰胺酸共聚物和其制造方法、清漆以及聚酰亚胺薄膜 |
| CN113621234B (zh) * | 2021-08-04 | 2022-08-30 | 深圳瑞华泰薄膜科技股份有限公司 | 一种超高模量高透光率聚酰亚胺薄膜及制备方法和用途 |
| CN118139913A (zh) * | 2022-07-29 | 2024-06-04 | Ｕｂｅ株式会社 | 聚酰亚胺前体组合物、聚酰亚胺膜和聚酰亚胺膜/基材层积体 |
| CN115141372B (zh) * | 2022-08-08 | 2024-01-26 | 波米科技有限公司 | 一种聚酰亚胺类物质及其应用 |
| WO2024185763A1 (ja) * | 2023-03-08 | 2024-09-12 | 株式会社カネカ | ポリイミド前駆体組成物、ポリイミド膜、積層体、電子デバイス、積層体の製造方法、ポリイミド膜の製造方法及び電子デバイスの製造方法 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU599517B2 (en) * | 1987-10-23 | 1990-07-19 | Mitsui Toatsu Chemicals Inc. | Method for preparing polyimide and composite material thereof |
| JP3978754B2 (ja) * | 1997-12-29 | 2007-09-19 | チッソ株式会社 | ポリアミド酸組成物、液晶配向膜、及び液晶表示素子 |
| JP3486358B2 (ja) | 1998-12-28 | 2004-01-13 | 日本電信電話株式会社 | 光学用ポリイミド基板 |
| JP2003155342A (ja) | 2001-11-19 | 2003-05-27 | Nippon Steel Chem Co Ltd | 脂環構造を有するポリイミド共重合体 |
| JP2004252373A (ja) * | 2003-02-21 | 2004-09-09 | Kanegafuchi Chem Ind Co Ltd | 液晶配向膜用ポリイミド樹脂 |
| JP2004307857A (ja) | 2003-03-26 | 2004-11-04 | Rikogaku Shinkokai | 蛍光性ポリイミド |
| JP4678142B2 (ja) | 2004-05-25 | 2011-04-27 | 日産化学工業株式会社 | 高透明性を有するポリ（アミド酸−イミド）共重合体の感光性樹脂組成物およびその硬化膜 |
| US7550194B2 (en) * | 2005-08-03 | 2009-06-23 | E. I. Du Pont De Nemours And Company | Low color polyimide compositions useful in optical type applications and methods and compositions relating thereto |
| JP2007063417A (ja) * | 2005-08-31 | 2007-03-15 | Fujifilm Corp | フィルムおよびフィルムの製造方法、ガスバリア層付フィルム、透明導電層付フィルム、並びに、画像表示装置 |
| KR20090038911A (ko) * | 2006-07-21 | 2009-04-21 | 도레이 카부시키가이샤 | 위상차 박막용 수지 조성물, 액정 표시 장치용 컬러 필터 기판, 및 액정 표시 장치, 및 위상차 박막 부착 액정 표시 장치용 컬러 필터 기판의 제조 방법 |
| KR101505899B1 (ko) * | 2007-10-23 | 2015-03-25 | 제이엔씨 주식회사 | 잉크젯용 잉크 |
| US8796411B2 (en) * | 2008-02-25 | 2014-08-05 | Hitachi Chemical Dupont Microsystems, Ltd. | Polyimide precursor composition, polyimide film, and transparent flexible film |
| WO2009116500A1 (ja) * | 2008-03-19 | 2009-09-24 | Jsr株式会社 | ポリイミド系材料、ポリイミドフィルム及びそれらの製造方法 |
| CN101580637B (zh) * | 2009-06-12 | 2011-08-31 | 东华大学 | 含脂环聚酰亚胺薄膜及其制备方法 |
| KR101898048B1 (ko) * | 2009-08-28 | 2018-09-12 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 액정 표시 소자 및 상기 소자에 사용되는 기판 |
| JPWO2011033690A1 (ja) * | 2009-09-16 | 2013-02-07 | ソルピー工業株式会社 | Ｐｍｄａ、ｄａｄｅ、ｂｐｄａ及びｂｃｄを含有する有機溶媒に可溶のポリイミド |
| CN102093558A (zh) * | 2009-12-14 | 2011-06-15 | 辽宁科技大学 | 一种可用作柔性透明导电膜衬底的聚酰亚胺膜材料及其制备方法 |
| JP5569441B2 (ja) * | 2010-08-27 | 2014-08-13 | Ｊｓｒ株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| CN102382303B (zh) * | 2011-08-16 | 2013-07-17 | 中国科学院宁波材料技术与工程研究所 | 无色透明的聚酰亚胺树脂材料及其制备方法 |
| JP2013082774A (ja) * | 2011-10-06 | 2013-05-09 | Kaneka Corp | 透明ポリイミドフィルムおよびその製造方法 |
| KR101339663B1 (ko) | 2011-12-30 | 2013-12-10 | 웅진케미칼 주식회사 | 저열팽창성 투명 폴리이미드 |
| KR101339664B1 (ko) * | 2011-12-30 | 2013-12-10 | 웅진케미칼 주식회사 | 저열팽창성 투명 폴리이미드 |
| JP6257302B2 (ja) * | 2012-12-20 | 2018-01-10 | 旭化成株式会社 | ポリイミド前駆体及びそれを含有する樹脂組成物、ポリイミドフィルム及びその製造方法、並びに、積層体及びその製造方法 |
| TWI488887B (zh) * | 2013-02-08 | 2015-06-21 | 長興材料工業股份有限公司 | 聚醯亞胺，由此形成之塗料組合物及其用途 |
| EP3018164B1 (en) * | 2013-07-05 | 2019-03-06 | Mitsubishi Gas Chemical Company, Inc. | Polyimide resin |
| JP6254197B2 (ja) * | 2014-02-14 | 2017-12-27 | 旭化成株式会社 | ポリイミド前駆体及びそれを含有する樹脂組成物 |
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| CN105916910A (zh) | 2016-08-31 |
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| KR20180069927A (ko) | 2018-06-25 |
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| CN110028666A (zh) | 2019-07-19 |
| TWI567135B (zh) | 2017-01-21 |
| JP2018031018A (ja) | 2018-03-01 |
| KR101869173B1 (ko) | 2018-06-19 |
| KR20160079836A (ko) | 2016-07-06 |
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